21 Hats Podcast: Recent Episodes
21 Hats
The 21 Hats Podcast is a weekly conversation with entrepreneurs who share their challenges and compare notes on how they’re coping with the pandemic, whether their businesses are as profitable as they should be, how big a price they are willing to pay for growth, and why they hired their brother-in-law. Every week, host Loren Feldman has a conversation with three of the show’s six regulars: Karen Clark Cole, CEO of Blink UX; Paul Downs, CEO of Paul Downs Cabinetmakers; Jay Goltz, CEO of The Goltz Group; William Vanderbloemen, CEO of Vanderbloemen Search Group; Dana White, CEO of Paralee Boyd; and Laura Zander, CEO of Jimmy Beans Wool. Every week, the owners talk about news stories that matter to business owners, and track what’s working and what’s not working on their own entrepreneurial journeys. Visit 21hats.com to read episode transcripts and learn more. The show is produced by Jess Thoubboron of Blank Word Productions.
Jaci Russo has had quite a summer. First, her husband and business partner, Michael, underwent an unexpected quadruple bypass. Fortunately, Michael's recovering well, and their branding agency passed an important test: With both founders largely out of commission, the team kept the business running and the clients happy. But that wasn't the only surprise Jaci had to deal with. For the past several years, she and Michael thought they knew exactly how they would eventually leave the business. They had a succession plan. They had a timetable. And they had already begun putting the pieces in place. Now, they're back to figuring it out.
This week, Jaci tells Jay Goltz what happened and how she's thinking about her options now. It's a reminder that succession planning isn't just about choosing among selling to family, employees, investors, or some other buyer. It's also about recognizing that circumstances change, people change, and even a plan that once seemed settled can suddenly become anything but.
Plus: We check in with Jay to see whether he's received the hundreds of thousands of dollars he's expecting in tariff refunds. And with Wayfair reporting improved sales, I ask Jay whether that's a sign the furniture business is finally recovering—or whether Wayfair's gains might actually be bad news for independent home stores like his. This episode is brought to you by Grasshopper Bank.
If you've built a successful business, you've likely been told the path to more success is obvious: hire employees, land bigger clients, lock in recurring revenue with retainers. But what if those aren't signs of progress? What if they're traps?This week, I talk with Pia Silva, author of Scale Solo, who argues that many of the traditional rules of entrepreneurship simply don't apply to solopreneurs. She explains why hiring too soon can derail a business, why retainers often aren't nearly as profitable as they appear, and why she'd rather do 10 $3,000 projects than one $30,000 engagement. Along the way, Pia also tells us why she and her husband named their branding agency Worstofalldesign, why she isn't afraid to tell clients, "You don't get a say," and how she's learned to sell clients on paying higher prices. This episode is brought to you by Grasshopper Bank.
This week, we begin with the story of Paloma Corona, the owner of a thriving preschool in Los Angeles who needed money to expand to a second location. She thought she was borrowing at an annual percentage rate of 13 percent. In reality, the effective APR was 170 percent. She also thought she was taking out a loan. Instead, she was placed in a merchant cash advance—an increasingly common form of financing that can sidestep many of the laws governing traditional loans. The daily payments quickly began draining not only the profits from her business, but also her personal savings. Her business survived, but only because a nonprofit lender stepped in to refinance the debt. Paloma’s story is especially troubling because she wasn’t reckless, uninformed, or running a failing business. She was trying to build a good business. But she was up against a financing industry that has become remarkably skilled at making extraordinarily expensive money look fast, easy, and affordable.
My guests today have all been fighting this problem from different vantage points. Jay Goltz owns a picture framing business and a home furnishings store in Chicago. Ami Kassar helps business owners secure SBA and other responsible financing. And Louis Caditz-Peck, who helped build LendingClub’s small business operation, is now executive director of the Responsible Business Lending Coalition.
In our conversation, we talk about why good businesses get steered into bad financing, how brokers can earn more by recommending the most expensive products, why offers embedded in platforms such as QuickBooks, PayPal, and DoorDash can be especially tempting, and what business owners should do before accepting fast money. We also ask what seems like a remarkably simple question: What could possibly be the argument against requiring every small business financing company to disclose, clearly and prominently, the true annual percentage rate it is charging? This episode is brought to you by Grasshopper Bank.
ESOPs are often presented as one of the best ways for a business owner to exit. You preserve your company's independence, reward the employees who helped build it, and create a retirement benefit that can be life-changing for the people who stay with the business. What gets less attention is that ESOPs are still businesses. They can lose customers. They can hit hard times. And because employees' retirement savings are often tied to the company, the stakes can be even higher than they are at a conventionally owned business.This week, Roland Burdett tells the story of Miklos Systems, a Virginia defense contractor that became an ESOP in 2006 and spent nearly two decades building an ownership culture in which employees truly thought and acted like owners. Then came the pandemic, the Great Resignation, and, most recently, the uncertainty created by DOGE and deep cuts to federal contracting. Suddenly, Roland found himself worrying not only about his employees' jobs, but about their retirement savings as well.Rather than continue rolling the dice, Miklos made the difficult decision to sell itself to a larger defense contractor. Roland takes us inside that process—from explaining the decision to employee-owners, to working with an outside trustee who ultimately had the authority to approve the deal, to the surprising complexity of unwinding an ESOP after 20 years. Along the way, he offers a refreshingly candid look at both the strengths and the limitations of employee ownership, and why, in the end, protecting the people who had helped build the company meant giving up the independence they had worked so hard to preserve. This episode is brought to you by Grasshopper Bank.
Side hustles have gone mainstream. More employees than ever are starting businesses of their own—sometimes to earn extra income, sometimes as insurance against layoffs, and sometimes because they dream of becoming entrepreneurs themselves. But what does that mean for the businesses they already work for? If you invest months in training an employee, isn’t it fair to expect that person to devote their best energy to helping your company grow? That's not an immediate concern for Lena McGuire, who's still a solopreneur. But as she prepares to hire and train her first employees, she worries about investing in people who ultimately may see her business as a stepping stone. Sarah Segal isn’t as concerned, but she does want her employees to view their jobs as careers, not placeholders. And then there's Channon Kennedy. While working full time at Silicon Valley Bank, Channon invented a woodworking tool, got it manufactured, landed national distribution, and traveled the country to trade shows—all, she says, without letting her day job suffer. And that’s what she expects from her employees with side hustles.
Meanwhile, both Lena and Sarah are wrestling with another challenge: finding the right home for their growing businesses. Lena needs a showroom but doesn't want to sink money into leased space—and she can't find a building to buy. "I'm missing out on growth," she says. "I feel like I'm stalled." Sarah has opened a second office in Silicon Valley, but she's wondering whether it's time to leave her quirky “starter” office in San Francisco for something that better reflects where her business is headed. Buying would be ideal, but that's easier said than done in San Francisco these days.
Plus: Sarah recently did something she hadn't done in almost a decade as a business owner—she turned on an out-of-office message and actually unplugged for a vacation. Spoiler alert: there was only one real crisis.
One thing I've noticed over the years is that business owners love talking about employees who think like owners, who take initiative, solve problems, and don't wait to be told what to do. The harder question, of course, is: How do you actually build a company that encourages people to behave that way? My guest this week thinks most businesses actually encourage people to do the opposite.Dean Meyer is an executive coach who specializes in organizational transformation, and he believes that employee engagement has a lot less to do with perks, personalities, or motivational speeches than it does with the way a business is designed. His core idea is deceptively simple: Every manager should run a business within the business—with customers, responsibilities, and the freedom to figure out how to deliver results. It's a different way of thinking about organizational structure, and as you'll hear, it challenges some widely accepted ideas, including what employee ownership and open-book management can—and can't—accomplish on their own.Along the way, Dean explains why he says he can predict where conflict exists just by looking at an organization chart, why he believes founders become the biggest obstacle to growth once a company reaches a certain size, and how one entrepreneur used these ideas to build a company that became better at innovating, integrating acquisitions, and attracting talent. Whether you agree with Dean or not, I think you'll find that he offers a fresh perspective on a question every growing business eventually confronts: How do you build an organization that doesn't depend on the founder to make everything happen? This episode is brought to you by Grasshopper Bank.
Nearly 10 years ago, Simon Bedding, who owns a manufacturing company in England, picked up a copy of Boss Life, Paul Downs' memoir about running (and almost losing) a manufacturing company in Pennsylvania. Simon liked the book enough to email Paul. Paul wrote back. And over the years, they've kind of stayed in touch. This year, as we mark the 250th anniversary of the United States spinning off from the United Kingdom, we thought it would be illuminating to get these two business owners together to compare notes. After all, their countries started with the same language and much of the same legal tradition, but two and a half centuries later, running a business on opposite sides of the Atlantic can feel very different.
In this conversation, Paul and Simon compare taxes, regulation, hiring, health care, government support, and what it's like to build a manufacturing business in their respective countries. Along the way, there are plenty of moments when one of them can't quite believe how the other has to operate. Wait—you can't fire an employee without going before a tribunal? Wait—you have to spend a week every year figuring out health insurance? Wait—your employees don’t have employment contracts?
And yet, for all of their differences, Paul and Simon also discover something else: Whether your factory is in Pennsylvania or southeast England, some challenges are universal. It's hard to find great people. It’s hard to fight city hall. In short, it's hard to build a successful business. And, as Paul puts it, "You're always going to learn something by talking to other business owners." This episode is brought to you by Grasshopper Bank.
Small business owners have plenty to worry about these days. According to John Arensmeyer, founder and CEO of Small Business Majority, his organization's surveys show optimism is slipping as owners grapple with soaring health insurance premiums, rising energy costs, and the higher price of imported goods. And yet, the wave of entrepreneurship that began during the pandemic hasn't faded. In fact, it's still growing. So what's going on? Why are so many people choosing this moment to start businesses? What do they think they're seeing? And perhaps the more important question: What can we do to improve their odds of success? Along the way, John also makes the case that one of today's politicians understands the needs of small businesses better than most. You may be surprised by who he names. This episode is brought to you by Grasshopper Bank.
If you’ve owned a business for any length of time, you’ve probably told yourself some version of this: I'll deal with succession as soon as I solve whatever crisis my business is confronting right now. The problem, of course, is that there's always another crisis to solve or opportunity to pursue, and time has a way of passing.
Jay Goltz has spent decades building a collection of successful businesses in Chicago. He knows he needs a succession plan. He knows that if something happened to him tomorrow, there’d be chaos. And he'd very much like to leave the business in the hands of the employees who helped build it. Over the years, he's considered the usual options—selling to a bigger company, to a few key employees, to an ESOP, even to an Employee Ownership Trust. But every option comes with compromises. And so, year after year, it’s been easier to focus on challenges that seem more urgent—until this past April, when Jay turned 70. "I realized," he says, "I can't kick this down the road much further."
This week, Jay sits down with David C. Barnett and Mel Gravely for an unusually candid conversation about what makes succession planning so difficult—even when you understand how important it is. Jay explains why he has no interest in selling, why money isn't really the issue, and why he still loves going to work every day. Mel, meanwhile, offers some tough love, suggesting that if protecting Jay's family and employees really are his priorities, then something else must be holding him back.
Mel also shares an unexpected twist in his own succession journey. After stepping away from the CEO role two and a half years ago to become executive chairman, Mel found himself pulled back into operations this spring—a reminder that even well-designed succession plans don't always unfold as expected. And along the way, David offers a blunt explanation for why many aging business owners overestimate what their companies are actually worth. The episode is brought to you by Grasshopper Bank.
There have been a lot of stories lately about companies getting hit with surprisingly large AI bills. They start using platforms like ChatGPT or Claude, usage grows faster than expected, and suddenly they're spending far more than they ever imagined. Should small businesses be worried? I invited AI consultant and longtime business owner Alan Pentz back on the podcast to find out. His answer may surprise you: for most small businesses, he says, runaway AI costs aren't the problem. If anything, he thinks they're spending too little.That led us into a wide-ranging conversation about why Alan has changed his thinking on how owners should approach AI, why today's pricing is effectively subsidized for smaller businesses, when it does—and doesn't—matter which model you're using, why mastering prompt writing is becoming less valuable than many people assume, and what happens when the companies behind the large language models finally have to start making real money.
Most business owners hope to reach the day when someone offers to buy their business. If that day comes, the payoff isn't just financial. It's validation for years of risk-taking, sleepless nights, personal guarantees, and sacrifices that most employees never see. But that success can raise an uncomfortable question: What exactly do owners owe the people who helped them get there? Should employees share in the proceeds when a business is sold? Does an owner have an obligation to find a buyer who will protect the culture and the jobs that have been built over the years? Or is the owner's responsibility fulfilled by paying people well, treating them fairly, and creating a great place to work so long as the business is theirs to run?
This week, Jay Goltz, Liz Picarazzi, and Ted Wolf wrestle with those questions—and not always from the same perspective. They agree that employees deserve respect and appreciation. But they also point out that employees weren't the ones who pledged their homes as collateral, absorbed the losses, or spent years wondering whether the business would survive. In other words, where should owners draw the line between gratitude and obligation?
Plus: As Liz expands Citibin beyond New York City, should her marketing reflect that shift? Or should she lean into her hometown roots and emphasize that if her trash bins can make it there, they can make it anywhere? Liz also explains her plan to capture some recurring revenue.
Business owners spend a lot of time preparing for things that could threaten their companies. They buy insurance, build cash reserves, create succession plans, and they worry about recessions, lawsuits, and key employees leaving. But there's one potentially devastating risk that many owners would rather not think about: What happens if the owner's marriage falls apart? This week, David Barnett explains how careful planning—including a prenuptial agreement—helped him avoid the worst-case scenarios when he got divorced. Jaci Russo offers almost the opposite perspective. She says building a business with her husband hasn't strained their marriage—in fact, it may actually have strengthened it by making the cost of walking away so high. Paul Downs, meanwhile, says the subject has barely crossed his mind, and has never come up in decades of discussing business issues with fellow entrepreneurs.
Along the way, we explore how divorce can leave a business frozen in place, unable to make important decisions or investments; whether owners should plan for the possibility just in case; and the remarkable challenge of couples who divorce but continue running a business together. Plus: Jaci reports back on what she learned at a Claude Cowork seminar.
Jared Bell never planned to own a fencing business. He took a summer job at Butte Fence in 1994, liked the work, and decided to skip college and stay. Thirteen years later, he bought out a partner and took over day-to-day operations—just in time for the Great Recession. The company survived that challenge and has gone on to thrive, but not by following a conventional growth playbook. Bell has expanded the business by repeatedly asking a simple question: Why buy from a supplier when we can do it better ourselves? Over the years, Butte Fence has developed new products, configured more efficient processes, and steadily moved upstream, turning vendors into competitors and creating entirely new businesses along the way. In our conversation, Bell explains how that strategy evolved, what it takes to pull it off, and how a small business can identify opportunities hiding in its own supply chain.
The new pay transparency laws were designed to help job applicants and narrow pay disparities. But they've also had an unintended consequence: Employees now have far more information about what other people are making—and that can raise some uncomfortable questions for business owners. How do you decide what a job is worth? How much should you pay compared to the market? How much should employees know about what their co-workers earn? This week, Jay Goltz, Jennifer Kerhin, and Ted Wolf compare notes on compensation.
Jennifer explains how her philosophy has evolved from offering below-market pay and maximum flexibility to providing competitive salaries, benefits, and career paths. Jay discusses the challenges of determining what employees are truly worth—and why a bad bonus plan can be worse than no bonus plan at all. Ted makes the case for paying above market—not because he wants superstars, but because he believes well-paid employees become more committed, more flexible, and ultimately, more productive.
Along the way, they discuss paying for health insurance, contractors versus employees, hiring mistakes, and the sometimes overlooked reality that while employees crave stability, business owners are the ones taking the financial risks. The result is a candid conversation about one of the hardest questions business owners face: What is the right way to compensate the people who help build your company? Plus: How concerned would you be if your employees found out how much money you, as the owner, are taking out of the business?
A health scare in 2015 prompted Julia Beardwood to confront a question many business owners prefer to postpone: What happens when it's time to leave the business? Over the next several years, the founder of the New York City branding agency Beardwood explored a range of possibilities, including selling to an ESOP and pursuing a strategic acquisition. But when the time came, the solution turned out to be much closer to home. Years earlier, Julia had implemented a compensation strategy that gave key employees a meaningful stake in the company's success. What began as a way to motivate and retain talent ultimately created a pathway for ownership transition.
The promise is seductive: Implement the right operating system and your frustrations disappear. Your employees become more accountable. Communication improves. Growth follows. Your business finally runs the way you always hoped it would. That's the promise behind EOS, the Entrepreneurial Operating System popularized by Gino Wickman's book Traction. Plenty of business owners swear by it. Plenty have spent tens of thousands of dollars hiring EOS implementers to help put it in place. But does it work?
This week, we’re republishing one of our favorite conversations, one in which Shawn Busse, Paul Downs, and Laura Zander compare notes on their own experiences with EOS. Laura hired an implementer and spent years trying to make the system work. Paul took a more selective, do-it-yourself approach. Shawn has watched EOS play out inside numerous client companies. What emerges is a much more nuanced picture than the one promised in the book. The three owners discuss when EOS can be genuinely valuable, when it's the wrong tool for the job, and why no operating system can compensate for having the wrong people in key roles. As Laura puts it, EOS can be incredibly helpful "for people like me 10 years ago, who just don't know what they're doing." The question is whether that's enough to justify the investment.
For years, Kim Robinson worked on the brand side, helping major companies connect with artists and creatives. Eventually, he decided he’d rather be working for the artists themselves. So he launched 3pts, a company that helps creatives handle the business side of their careers—everything from pricing and marketing to partnerships and strategy—so they can spend more time focused on the work they love.The first challenge, Kim says, is convincing artists that thinking about money and business doesn’t somehow compromise their creativity. The second is helping them understand that even the most gifted creatives still need a framework for pricing, positioning, and building sustainable careers. In our conversation, Kim explains why so many artists struggle with the entrepreneurial side of their work, what brands often misunderstand about creative talent, and why he eventually realized he had more in common with his clients than he expected.
This week, Sarah Segal, Jaci Russo, and Lena McGuire tackle a question many service business owners face: Which is the bigger risk—an employee who feels overburdened or a client who feels neglected? The discussion begins with Sarah explaining why she's had to reestablish boundaries with some clients who were texting and calling her employees after hours and bypassing the systems her agency has put in place. Sarah wants her team to be able to disconnect at the end of the day, and she wants clients communicating with the entire team assigned to their account—not developing overly close relationships with individual employees. In her view, protecting employees from burnout ultimately leads to better service for clients.
Jaci approaches the challenge very differently. Her creative staff rarely communicate directly with clients. Instead, account managers serve as the sole point of contact, much like restaurant servers relaying orders between diners and the kitchen. The goal is to protect specialists from interruptions, keep them focused on their work, and ensure that client communication remains clear and consistent. The result is a lively conversation about competing priorities, client expectations, employee well-being, and the hidden risks that can emerge when clients become too dependent on individual employees. Plus: Have you ever had an employee leave and take clients with them?
Sean Joy is head of M&A at Chenmark, a Portland, Maine-based holding company that acquires a handful of small businesses each year. At first glance, Chenmark may sound like a traditional private equity firm, but it isn't. The company is family- and employee-owned, and when it buys a business, the goal isn't to improve it and sell it a few years later. The goal is to own it indefinitely.In our conversation, Sean explains what Chenmark looks for in an acquisition, how it finds businesses to buy, what it's willing to pay, and how it approaches management after a deal closes. For owners thinking about succession, Chenmark offers a different path—one that sits somewhere between selling to private equity, selling to employees, or passing the business on to the next generation.
This week, we explore some contrasting opinions about artificial intelligence. Paul Downs has serious doubts that AI will ever have a significant impact on his business. Paul, who builds custom conference tables, says his business depends on something AI still lacks: real world experience. While AI can generate impressive images and concepts, he argues that it has no understanding of manufacturing constraints, material properties, production processes, or the capabilities of the people and machines that have to bring an idea to life. “An image of a thing that looks cool is not a design,” Paul says. “A design is a set of information that's informed by intelligence and experience.”
Ted Wolf, who helps companies implement AI, agrees that AI can't replace the collective creativity and judgment of skilled people. But he believes Paul may be looking at the problem too broadly. Instead of asking whether AI can design and build custom furniture, Ted suggests breaking the workflow into smaller pieces and experimenting with targeted applications. “You know your business better than anybody else,” Ted tells Paul. “But don't look at the big picture and think that's the entire thing. There are many small pieces that people can start doing today.”
* The result is a thoughtful debate about one of the biggest questions facing small business owners: Is AI going to change everything, or are there businesses where human expertise will remain irreplaceable?
* Plus: Channon Kennedy shares* what she learned from participating in a Goldman Sachs program for Black women entrepreneurs. And the owners discuss what debt can—and cannot—do for a business: “Funding does not fix a broken business model. It makes it die faster.”
When Bryan Clayton graduated from college, he discovered he had two options: take an entry-level job and a pay cut—or go back to mowing lawns, which was already making him more money. He chose the lawns. Over time, he built a commercial landscaping business that grew to $10 million in annual revenue before eventually selling it. But even while running that business, Clayton had been thinking about another problem: why was it still so hard for homeowners to hire a reliable lawn service?Despite having no background in technology, Clayton bootstrapped a platform called GreenPal, which connects homeowners with lawn-care specialists—essentially an Uber for landscapers. Today, still entirely self-funded by Clayton and his partners, GreenPal serves more than 300,000 users nationwide. In our conversation, Clayton talks about the operational mistakes that trip up many small businesses, how GreenPal uses both incentives and penalties to improve landscaper performance, and how the company is using AI to identify contractors whose businesses may be headed for trouble.
Twenty years ago, Bo Burlingham gave a name to a feeling a lot of business owners had struggled to articulate. In his book Small Giants, Bo profiled companies that had chosen not to chase growth at all costs. Most were bootstrapped, owner-operated businesses that cared less about getting big than about building something enduring, meaningful, and excellent. They weren’t anti-growth. They just wanted growth to be intentional. And for many owners who read the book, the reaction was immediate: “I thought I was the only one who felt this way.” Out of that recognition grew a community—and eventually an organization—led in large part by Paul Spiegelman, whose own company embodied the Small Giants philosophy. With Bo’s encouragement, Paul launched the Small Giants organization 15 years ago to connect owners trying to build great companies without sacrificing culture, independence, or quality of life.
At our recent 21 Hats Live gathering in Cincinnati, we explored where that movement goes next in a Brainstorm session with Jean Moncrieff, who took over leadership of the Small Giants organization last year. Jean—who’s from South Africa, lives in Zurich, but is moving to the U.S.—brings both momentum and candor to the role. He recently led his first Small Giants Summit in Detroit, which attendees—including me—praised for its renewed energy and sense of purpose. He’s also the author of a terrific new book, Finding Freedom: The Business Owner’s Guide to Building a Valuable Company and a Meaningful Life. But as you’ll hear, Jean recognizes there are challenges ahead.
What exactly is Small Giants today? Who is it for? What makes it different from the many other organizations competing for the attention of business owners? Does it need a more formal set of principles—or even an operating system—to help companies put its philosophy into practice? Can it stay true to its founding mission while also attracting businesses large enough to support its events and programs? Ultimately, the conversation arrives at a tension at the heart of the enterprise: Can the Small Giants organization itself become a sustainable, profitable business without losing the values it was created to protect? In other words, can Small Giants become a true small giant?
Show Notes:The organizations discussed in this episode include: The Great Game of Business, the Tugboat Institute, and EOS Worldwide.
The books discussed in this episode include: Finding Freedom by Jean Moncrieff, Small Giants by Bo Burlingham, Another Way by Dave Whorton with Bo Burlingham, The Great Game of Business by Jack Stack and Bo Burlingham, The Power of Mattering by Zach Mercurio, and Profit First by Mike Michalowicz.
The businesses discussed in this episode include: Smiley Technologies, ITR Economics, Zingerman’s Community of Businesses, Text-Em-All, Tasty Catering, Venturity, ImageOne, and Atomic Object.
When Eugene Khayman first got involved with Million Dollar Sellers, it was essentially a support group for entrepreneurs building businesses on Amazon. Back then, the opportunity seemed almost limitless. Today, ecommerce feels a lot more complicated. Competition is tougher. Customer acquisition is more expensive. And sellers have many options beyond Amazon. At the same time, Khayman believes Amazon itself has changed—and not for the better. In a recent post on X, he argued that Amazon’s growing fees are “destroying the marketplace it created.” He’s now leading a campaign called Save Our Sellers, aimed at pushing back on policies that many third-party sellers believe are squeezing the businesses that helped make Amazon dominant in the first place.In this conversation, Khayman explains what sophisticated ecommerce operators understand that many traditional small businesses still don’t, how AI is beginning to reshape online selling, and why building a business on someone else’s platform can feel both irresistible and dangerous. We also talk about the tradeoffs between selling through your own website versus chasing visibility on giant platforms—and whether Amazon is still worth it.
Michelle Wyatt has replayed the events in her mind countless times, looking for warning signs she might have missed. But even now, she can’t find any. Both employees had passed background checks and drug tests. Both were considered trusted, valued members of the team. And yet, within a span of months, two violent incidents involving employees left Michelle and her company reeling. In this week’s conversation, Michelle joins Jay Goltz, who has dealt with employee violence in his own business, and special guest Sandy Kapell, who’s made a career leading human resources, to wrestle with a question that haunts a lot of business owners: How much responsibility can you reasonably bear for the actions of your employees?
The discussion goes beyond hiring practices and background checks. Michelle talks candidly about the grief her team experienced, the guilt of wondering whether she should have seen something sooner, the relief that the violence didn’t occur aboard her riverboat cruise ship, and the unsettling realization that no amount of experience truly prepares you for something like this. “Please stop torturing yourself,” Jay tells Michelle. “From what you've said, there's just nothing you could have done about this. It's part of business, unfortunately.”
Hannah Sandmeyer spent years acquiring ecommerce businesses for an Amazon aggregator, giving her a front-row seat to how deals get done—and what often gets lost in the process. Too many owners, she came to believe, are forced to choose between shutting down their businesses or selling to buyers whose priorities may have little to do with preserving the company, the culture, or the people who built it. So she decided to build an alternative. Hannah is now founder and CEO of Steward Market, which she describes as “the first marketplace for ethical exits.”In this week’s Dashboard, she explains what makes an exit “ethical,” why some owners are actively looking for alternatives to private equity, and how Steward Market hopes to connect values-driven sellers with buyers who want to continue what those owners have built—not simply maximize short-term returns. She also explains why the company chose a business model that doesn’t rely on taking commissions from deals.
When Kate Morgan started thinking seriously about selling her business, she assumed the big payoff would come at closing. But as she tells David C. Barnett and Paul Downs this week, she’s come to understand that the smarter move might be not selling—at least not yet. Why? Because if the business keeps performing and she can gradually remove herself from the day-to-day operations, she may ultimately make more money by continuing to own it. That’s partly because, as David explains, small businesses often sell for lower multiples than owners expect. Which means the real value may not be in a clean exit, but in continuing to collect profits while slowly transitioning ownership to key employees. “So you'll be selling the business,” says David, “and you'll be collecting dividends or distributions on top of that. This is one of the most lucrative exits there can be.”
Of course, delaying a sale comes with its own risks. Markets change. Businesses cool off. Buyers get nervous. “You have to make the decision and make the sale happen while you've got a full head of steam,” David warns. Wait too long, and the numbers can start sliding in ways that dramatically reduce what buyers are willing to pay.
Plus: A Reddit post raises a brutal management challenge: What’s the best way to lay off a relative? “It really can't affect your decision,” says Paul. “Because if it needs to be done, it needs to be done.” That doesn’t make it easier. It just means you may have to live with both the business consequences and the family consequences at the same time.
Most business owners know they need marketing. What many don’t know is what they should be paying for it—or what they should expect in return. So when an SEO agency proposes a $3,500-a-month plan, how do you assess whether it’s a smart investment or an expensive gamble? Do you know how many new customers it would take to make that spend worthwhile? Do you even have the data to answer that question? This week, Shawn Busse says too many owners are making those decisions in the dark. He offers a practical framework to help you do the math to evaluate marketing proposals, set realistic expectations, and decide what’s worth spending—and what isn’t.
Every business owner looks forward to that big break—the moment that you land a big client or a major retailer, or do something that puts you on a national stage. But those opportunities don’t just reward you. They can also expose you—especially if you have to take on debt or ramp up production or do things you haven’t done before. Four years ago, when Liz Picarazzi won a high-profile installation for her trash enclosures in Times Square, it was exactly that kind of opportunity. Her enclosures were put to the test in as public and as challenging an environment as she could imagine. And, by any reasonable measure, they failed. In pursuing that opportunity, Liz took a risk that led to what she calls the worst day of her professional life. It also turned out to be, as she tells Lena McGuire, the best thing that could have happened to her business. That moment forced changes she might never have made otherwise, pushing her to innovate faster and sending her business on a very different trajectory.
Meanwhile, Lena is dealing with a quieter version of the same problem: what it really takes to move your business forward. She knows her systems need an upgrade. She’s bought the software. But like a lot of owners, she’s stuck in the messy middle—paying for the future while still trapped in the past, with no time to bridge the gap. How do you choose between tasks that generate revenue immediately and those that will improve operations over time?
For years, the Wine School of Philadelphia and PhillyWine LLC coexisted in the genteel world of wine education. Then a trademark dispute turned that quiet coexistence into a legal battle—complete with accusations, lawsuits, and mounting costs.This week, Keith Wallace, founder of the Wine School of Philadelphia, joins me to talk about what happens when a business owner who’s tried to avoid litigation at all costs suddenly finds himself in the thick of it. He shares what the fight has actually required—financially, emotionally, and strategically—and what he wishes he had done differently before things escalated. Because one of the hardest lessons for any owner is this: you don’t have to want a legal fight to end up in one.
For Lena McGuire, scope creep really can show up around every corner. She’s in the home remodeling business. But for most owners, including Jaci Russo and Ted Wolf, projects that expand out of control can be less visible but just as hard to contain. It’s baked into the job, because every assignment comes with a built-in tradeoff: Protect your margins or protect the relationship. And especially in the early days of a business, when reputation feels like everything, that’s not much of a choice. “I was afraid to have tough conversations with people,” Ted says. “I just wanted everybody to like us.”
Over time, systems help and boundaries get clearer. But the pressure never fully disappears. There’s always one more request, one more detail to tweak—especially when you’re thinking about the reviews and testimonials. “You want to get those nice photos at the end,” says remodeler Lena. “You want to get a referral.” This week, Lena, Jaci, and Ted talk about how their thinking on scope creep has evolved—and why it never stops being an issue.
Plus: On the small business subreddit, an owner recently posted that he finds chasing accounts receivable so distasteful—it feels like begging—that he often puts it off and hopes for the best. “Is this just me?” he wants to know. “Or is this a common thing for small business owners?” We discuss. And Jaci explains why, even if she could get it, she wouldn’t even consider accepting a $500 million account promoting a big deal consumer brand.
Despite what we’ve been reading about tariffs and immigration and inflation and health insurance, the macro economy has actually held up better than many economists expected over the past year. Unemployment is low, corporate profits are high, and the stock markets have been setting records. So, this week, I put the question to John Arensmeyer, CEO and founder of Small Business Majority: Are things really that tough for small businesses? Well, yes, says John. It’s not necessarily any one issue, he says. It’s the constant drip, drip, drip of many issues. In this week’s conversation, we tackle several of the big ones.
Early on, William Vanderbloemen’s search firm was exactly the kind of business HubSpot, the marketing platform, was built to help. William had a highly specialized audience, his team produced content that his audience needed, and HubSpot helped make sure the right people found it. Back then, he tells Kate Morgan and Jaci Russo, HubSpot’s promise was that it could help a David compete with a Goliath, and that’s what it did for Vanderbloemen Search.
But that was almost 20 years ago, long before AI began reshaping how people discover information. Now, William contends, the rules are changing. If you create strong content for a specific audience, large language models can do more and more of the work of connecting that content to the people looking for it. Which raises a question: If that’s where marketing is headed, do small businesses still need a sophisticated platform like HubSpot? In this week’s episode, William shares his doubts.
Along the way, the three owners also discuss why Kate changed her mind about selling her business, whether companies really need to pay attention to their Glassdoor reviews, and what a plumber should tell an SEO agency that wants a monthly retainer of $12,500.
Hiring a full-time marketing team isn’t realistic for a lot of small businesses—but doing nothing may not be an option either. This week, Johnathan Grzybowski explains how Penji, the platform he co-founded, offers a different path: subscription-based access to vetted creatives matched to your specific needs.We talk about how that model actually works in practice, where it fits (and doesn’t) for small businesses, and how Penji manages the tension between competing with—and supporting—traditional agencies. Plus: we talk about what happens to a business like Penji as AI reshapes creative work and why Johnathan believes there’s ultimately only one marketing metric that matters: revenue.
Sandy Kapell knows HR—just not the version most business owners live with. After years leading human resources for corporations, Sandy launched her own business, Trakehner Leadership, to bring that expertise to companies that need help. And she’s quickly found a big opportunity: Most small businesses don’t have HR departments, but they still have all the same HR challenges.
The catch? Sandy has also realized that knowing HR isn’t the same as knowing how owners think about HR. Or how they talk about it. Or what they’re actually willing to pay for it. So for our latest 21 Hats Brainstorm, we brought in a panel of owners to help Sandy pressure test her assumptions, refine her pitch, and figure out what HR looks like in companies where, as one owner puts it, I tell everyone what the plan is, and then I say, “‘If you don't like it, talk to HR.’ And the joke is, I am HR. I am the owner.”
Along the way, Sandy and the panelists dig into questions like: When does a business really need HR? What does good HR even look like at 10 or 20 employees? And how do you offer structure and support without sounding like the police or, even worse, like an HR person? Because what Sandy is really trying to do is to take a function most owners resist and make it something they actually want.
In her thirties, Lisa Woodruff hit a breaking point—overwhelmed, overweight, and depressed, as she puts it. So she made a radical decision: she quit her job as a school teacher and set out to get her own life in order. What started as a personal reset became a business—Organize 365—built around a simple but powerful idea: running a household isn’t all that different from running a company.In her new book, Escaping Quicksand, Lisa argues that households, like businesses, need systems, delegation, and intentional leadership. But she also makes a point that may resonate with a lot of listeners: for women especially, the stakes—and the expectations—are different. This week, Lisa explains what she’s learned about escaping overwhelm and why treating your home like a business might be the key to getting your life back.
Pricing a service business sounds straightforward—until you actually have to do it. How much should you charge? What’s reasonable? And what happens when “reasonable” isn’t enough to keep the business healthy? This week, Sarah Segal walks David C. Barnett and Liz Picarazzi through how she thinks about pricing her PR services—why she aims for consistency across clients and why she resists charging based on what the market will bear but insists on building in enough margin to stay profitable. It’s a balancing act between values and reality, and not always a comfortable one.
The conversation gets into practical questions every business eventually faces: Do you raise prices a little every year, or wait until you’re forced to raise them more than just a little? Do you price based on your costs—or your customer’s perceived value? And how do you handle those conversations without damaging relationships you genuinely care about?
Plus: Liz expects a tariff refund—but isn’t counting on it to help very much. She also explains why she’s stopped flying employees around the country for installations.
Shawn Busse has never been an AI evangelist. If anything, he’s been wary of the hype. But lately, his thinking has started to shift. While it’s still early, Shawn sees AI pushing marketing away from the soul-deadening world of SEO hacks and keyword stuffing—and toward something far more human: real storytelling and authentic brand building. In this week’s Dashboard, he explains what he’s seeing in his own business and with clients, and what it may mean for owners trying to figure out where to focus next.
It’s easy to condemn the horror stories coming out of Noma, the celebrated restaurant in Copenhagen. But this week, Jay Goltz, Jennifer Kerhin, and Ted Wolf confront a harder question: How far are the rest of us—business owners in every industry—from crossing the line? Because it’s not just restaurants. Most owners don’t set out to be abusive. They set out to build something great. And somewhere along the way, high standards can start to blur into something else. ‘I was out of control when I was in my 20s,’ Jay admits.
So, what changed? And where did the owners land? How much command and control is actually necessary? When does pushing someone cross the line—and when does not pushing them enough become its own failure? Have you ever held onto the wrong employee too long? Or pushed the right one too hard? Jay doesn’t sugarcoat his opinion about yellers: “You’re going to tell me you’re passionate. I’m going to tell you, ‘You’re an asshole.’”
The group digs into the trade-offs every owner faces: hiring versus managing, systems versus stars, culture versus performance. What do you do with the high performer who damages the team? Can you really coach anyone to excellence—or are there limits? And then there’s the quiet warning sign many owners ignore: Something goes wrong, and someone says, “Oh, well, everybody knows how Bob is.” That, says Jay, is when you know you’ve got a problem. This is a conversation about judgment calls—messy, human, unavoidable. Because as Jennifer puts it, “It’s really hard to manage people.”
Chris Campbell started his first business at 18 and has since built and sold companies in landscaping, construction, furniture, and marketing. After his most recent exit, he spent years searching for a business to buy—and found nothing. That dead end turned out to be an opening.Instead, Chris and a group of partners—including his wife, Emily—decided to start something from scratch. The result: a plan for Banana Daddy, a high-concept soft-serve shop built around banana ice cream that would take $2 million to open. Every experienced restaurant operator they consulted had the same reaction: Don’t do it. They did it anyway.It's less than a month in, but so far, Banana Daddy is exceeding expectations. Fueled in part by playful, slightly suggestive, but still kid-friendly marketing—”Please Lick Responsibly!”—it draws lines around the block and has even required a bouncer to manage the crowds. Along the way, the team has discovered something they didn’t expect: a surprising number of people want ice cream first thing in the morning. “It’s bananas,” says Chris. And this is only the first step in a much bigger plan.
Given everything going on in the world, you might expect a rough start to the year. But for Paul Downs, Jennifer Kerhin, and Jaci Russo, 2026 has actually begun quite well. In fact, Jennifer and Jaci say they’re finally climbing out of what many owners call the Valley of Death—that long stretch when the business depends on you for everything and when it starts to outgrow your people and your systems. Exiting the valley can take a lot longer than people expect. Jennifer is seeing daylight in year 17. Paul says it took him 25 years, a quarter of a century. “Most of that time,” he admits, “I was just wallowing in ignorance.” One lesson they’ve learned the hard way: growing too fast can do real damage. “You burn out your employees,” Jennifer says. “You provide poor quality control to your clients. You make everybody upset and angry.”
Along the way, the three owners cover a lot of ground: what actually makes trade shows worth the investment (hint: it’s what you do before and after), why you may not be able to copyright that graphic design, why your logo needs a trademark, why Paul’s Google traffic is holding up but his Middle East expansion is on hold, what Jaci has uncovered about the shocking cost gap in health insurance for her female employees, and why it’s insane that business owners have to manage their employees’ health insurance in the first place. It’s a wide-ranging conversation—but underneath it all is a theme most owners will recognize: Progress doesn’t always come from big breakthroughs. Sometimes it comes from surviving long enough to figure things out.
For most business owners, rewarding employees for doing their jobs well is just common sense. Hit your numbers, get a bonus. Sell more, earn more. Perform better, get paid more. That’s how motivation works…right?This week, management consultant Kelly Allan asks owners to reconsider that assumption. Allan is steeped in the teachings of W. Edwards Deming, the management thinker widely credited with inspiring Japan’s post–World War II industrial revival. Deming argued that pay-for-performance systems don’t actually improve performance. Instead, they create unintended consequences—encouraging people to chase metrics, compete with colleagues, and optimize the wrong things.In Deming’s view—and in Allan’s—performance isn’t primarily about individuals at all. It’s about the system they work in. In our conversation, Kelly explains why incentives often backfire and how owners who are curious can begin experimenting with a different approach.
It’s already been quite a decade for owners: a pandemic, inflation, tariffs, and now, suddenly, war with Iran—bringing with it the biggest spike in oil prices ever. And looming over everything is the still-uncertain impact of artificial intelligence. This week, David C. Barnett, Jay Goltz, and Ted Wolf talk about how all that uncertainty is shaping the decisions owners are making right now—from whether it’s wise to invest in new equipment to how some lenders are demanding that would-be borrowers articulate their AI strategy before obtaining a loan.
The implications of all of this vary by industry, but Dave says some sectors suddenly look a lot riskier than they did a year ago. “I don't know if I'd want to get a 90-percent loan to buy a marketing agency today,” he says. At the same time, the economics of AI could push owners to move faster than they might otherwise. As Dave notes, if a $10,000 or $20,000 investment in AI can quickly replace two positions, that’s the kind of return many owners will find hard to ignore when expenses are rising.
Along the way, the three discuss why periods like this can also create unexpected opportunities. Keep your eyes open, Dave advises. “A lot of those opportunities may come from a competitor stumbling.”Plus: what happens when business owners suddenly realize they should have been collecting sales tax all along. Do you pay the back taxes yourself? Start collecting now and hope for the best? Or is there a smarter way to fix the problem?
It does in this sense, says Victor Hwang, founder of Right to Start, an advocacy group that works to expand entrepreneurial opportunity: While starting a business can be daunting, many Americans assume it’s even more daunting than it actually is. For six years, Victor and his organization have tried to address that concern by removing barriers to entry and spreading awareness of entrepreneurial opportunities. In this episode, Victor discusses the progress Right to Start has made, including significant recent steps in Oklahoma. He also has big plans for the 250th celebration of what he likes to call America’s startup.
Despite the waves of uncertainty crashing across the economy, this week we hear from three owners who feel cautiously good about how their year has started. David C. Barnett budgeted for slightly less revenue in 2026, but he’s operating more efficiently and expects to turn a bigger profit. Jaci Russo is hitting her revenue projections—and after implementing a profit-first accounting system, she says the results have been “eye-opening.” And while Lena McGuire isn’t quite on track to meet her aggressive goal of doubling her business this year, she’s doing far better than she did a year ago.
Along the way, we talk about getting runaway software subscriptions under control, figuring out how businesses get discovered in an AI world, and why Jaci’s health plan charges almost three times as much to cover female employees as it does comparable male employees. And we consider a question that might have sounded ridiculous not long ago: Has it become harder to get a job than it is to start a business?
In this sponsored conversation, Mike Butler, CEO of Grasshopper Bank, argues that business owners shouldn’t have to choose between speed and stability when it comes to their bank. Grasshopper has no branches, but it does offer full-service lending — with the quick decisions you might expect from an alternative lender and the rates you’d expect from a traditional one.Butler also explains how the bank is using AI to simplify everyday tasks — like finding a specific transaction in seconds instead of digging through statements — and we talk about a question many owners still wonder about: Do you lose something when you give up the local banker relationship? Along the way, we discuss which businesses are the best fit for Grasshopper, what customers actually value most, and why Butler decided to merge the bank with a larger company, Enova.
For the past six years, we’ve done our best to avoid talking politics on this podcast. By focusing on the business realities owners confront every day, we’ve tried to create a space where people with very different perspectives—from different industries and different parts of the country—can still learn from one another. That’s something we take seriously. But we also live in the real world. And lately, the real world has been making that separation harder.
On this episode, Paul Downs, Kate Morgan, and Liz Picarazzi talk about those moments when business and personal beliefs collide—and when staying silent may not feel like an option. They’ve each faced uncomfortable questions: What do you do when an employee says something you find objectionable? Are there customers you simply won’t work with? How do you stay true to your values without putting your company at risk? There are no easy answers here. And not everyone will agree on where the line should be drawn. But as always, there’s real value in seeing how other owners handle tricky situations.
A lot of business owners are taking a wait-and-see approach with artificial intelligence. They’ve heard the hype—but they’ve also heard about the slop, the hallucinations, and the research suggesting many AI projects fail to deliver. For plenty of owners, that’s reason enough to assume this might be another passing obsession—like Y2K, Clubhouse, or the metaverse—and to sit back until the dust settles.
But not these three owners: David C. Barnett, Jaci Russo, and William Vanderbloemen have decided that waiting is the bigger risk. They’re taking courses, they’re teaching courses, they’re building agents, and they’re rethinking processes and workflows—all in search of an edge that may not be available forever. And they’re already seeing results.
In this episode, they share what’s actually working so far, including some early experiments that could reduce their reliance on Google AdWords. They also talk candidly about what they won’t do with AI, how they sidestep the slop, and why each of them believes this is one of those rare moments when experimentation isn’t optional.
Yes, says Gene Marks in this week’s Dashboard, the Supreme Court’s tariff decision, while correct, has created a mess. No, you shouldn’t make any plans to spend your tariff refund money. And no, there’s no telling where the Trump administration might be heading. But he does offer this one shred of certainty: For many businesses that have been paying the so-called reciprocal tariffs, if they plan for a 15-percent tariff rate going forward, they’ll probably be in reasonably safe territory.
Sooner or later, most business owners run into the same unsettling question: How do I actually get out of this thing? Pass it to family? Sell to a competitor? To key employees? To private equity? To an ESOP or an Employee Ownership Trust? Or maybe just shut it down?There’s no shortage of advice—but almost all of it comes with strings attached. Most advisors know one path best, and not coincidentally, it’s the path they’re paid to promote. Sorting through the options on your own can feel overwhelming, expensive, and risky. What if there were a place to get an honest, apples-to-apples comparison—one that looks at your specific business and lays out what really fits?That’s the problem Sonali Kothari is trying to solve with Zolidar, a startup she co-founded. In this episode, she explains how the company is building a tool to help owners think clearly about their exit—and why that process shouldn’t start five years too late. You can even test-drive it yourself with Zolidar’s free 10-minute Day Zero Guide for a preliminary assessment.
Sometimes the best conversations start with a simple question—and then another, and another. This week, we put Kate Morgan, Jaci Russo, and Ted Wolf in the hot seat and fire away: Are you hiring? Are you finding impressive job candidates? What was the worst job you ever had—and did you learn anything from it? Have you bought crypto? If you had $10,000 a month to spend on marketing, where would it go? Should a marketing agency ever turn its marketing over to another marketing agency? What’s holding you back? What’s the simplest thing you’ve never quite figured out how to do?
None of these are trick questions, but they don’t necessarily have easy answers. Kate admits she’s never opened her accounting software. Jaci says one of the best things that ever happened to her was getting fired. Ted recounts losing 40 percent of his company’s revenue in a single weekend. Running a business means living with trade-offs, uncertainty, and the occasional punch to the gut. As Jaci reminds us, it usually works out—one way or another. But that doesn’t mean the answers are simple when you’re in the middle of it.
Kelly Berry’s introduction to small-business ownership came at a moment when most new parents are focused on something else entirely. She had just come home from the hospital after giving birth when her husband handed her a personal guarantee to sign. He had quit his job to start a business.“So if this fails,” she said, “you’ll be unemployed and we’ll be homeless?”“Yep,” he replied.That moment made the risks of entrepreneurship very real—and it helped set Kelly on the path she’s been on ever since. She went on to earn her MBA, work with economic-development organizations, and eventually launch her own business running peer groups for business owners. Her focus has always been the same: helping owners navigate the challenges they face—together.In this week’s Dashboard, Kelly shares what she’s seeing on the front lines of small business, why peer groups can be so powerful, and how she’s working to bring that support to owners in rural communities who may not have access to in-person groups. She also talks about what it takes to build her own business along the way. And if you’d like to explore whether a peer group might be right for you, you can start with a short quiz she’s created.
Almost every growing business experiences a moment when success starts creating as many problems as it solves. Sales are up. The team is bigger. The product line is broader. And suddenly, the systems that got you here start to break. That’s where Liz Picarazzi finds herself right now. “We’re in the valley of death,” she says. “And we really need help.” Liz’s company, Citibin, made the most recent Inc. 5000 list, but Citibin has also hit that dangerous in-between stage—too big to run on improvisation, too small to have put in place all of the processes it needs.
So Liz is trying to grow her way out of the valley. She’s hired a marketing agency. A growth consultant. And two AI advisors. She’s testing new domestic fabricators. And she’s rebuilding her website from the ground up—because right now, it’s generating no more than 10 percent of sales, and she knows it can do better. The site hasn’t kept up with her expanding product line, and it isn’t even optimized for search engine discovery, let alone for generative AI discovery.
Talking it through with Paul Downs and Jaci Russo, Liz confronts some uncomfortable questions: How much copy is “enough” for AI? How transparent should pricing be—especially for a premium product whose prices could scare away some customers? And who has a better feel for the company’s story—the owner who’s lived it or the agency that has more experience helping businesses connect with customers? Not surprisingly, Liz and Jaci have different instincts on that one. What follows is a candid look at what it takes to rebuild a growing business at the dawn of a new era.
For most business owners, growth is the goal. More customers. More revenue. Bigger numbers. Bigger opportunities. And often, more pressure. But what if the way most of us think about growth is actually setting us up for trouble? Economist Gary Kunkle has spent years studying what really drives business performance. Not in headlines or case studies—but in large sets of real-world data. And what he’s found is that fast, aggressive growth often creates risks that owners don’t see until it’s too late.One reason is this: His research indicates that in most companies, about 20 percent of customers generate almost all of the profit. Most of the rest barely break even. And a surprising number quietly lose money. So when you chase growth, you’re often just adding more of the wrong customers—more complexity, more strain, more work, and less margin. In this conversation, Gary explains why steady, disciplined growth tends to outperform flashy expansion—and how understanding your own numbers can help you avoid the traps that derail so many otherwise strong businesses. Want to learn more? You can go to Gary’s website or email him directly: gmkunkle@yahoo.com.
Alan Pentz is convinced a wave of disruption is about to crash into small businesses—and he’s doing everything he can to warn owners before it hits. He’s writing, teaching, consulting, waving the red flag. He’s just not sure anyone is ready to listen. “I don’t know if you’ve seen Don’t Look Up,” he says, “but it’s kind of like that. The asteroid’s coming—and everyone’s still walking around like it’s normal.” In our latest 21 Hats Brainstorm, Alan put his own future on the table. He asked a panel of owners to help him answer a hard question: Do business owners actually want help adopting AI? And if they do, what kind of help will they pay for? Is there a real, scalable business here—or just a lot of interest and polite nodding? And there’s one more twist: Alan already owns a successful consulting firm. So he also has to decide whether this opportunity is worth jumping back into the startup grind to build another service-heavy business from scratch. This 21 Hats Brainstorm is brought to you by New Bridge Studios, which helps companies, creators, and causes connect their stories to the bottom line.
Ryan Markewich knows the landscaping business from the inside. He built and sold a successful landscaping company in British Columbia, then spent years coaching owners of all kinds of businesses through the Great Game of Business—helping them understand their numbers, their people, and their decisions. Now he’s a certified advisor with an AI-powered platform called LeanScaper It’s only been around for about a year, and it’s designed specifically for landscaping businesses but it’s growing quickly because it offers a practical, step-by-step playbook that helps owners think through pricing, staffing, cash flow, and growth decisions, using AI to guide—not replace—their judgment. This week on Dashboard, Ryan walks us through what happens when one industry gets an AI playbook for running a business—and why landscaping may be an early glimpse of what’s coming for a lot of small business owners.
Things are suddenly moving fast at Sarah Segal’s San Francisco PR firm. Several new clients look likely to sign on, and for the first time in a while, growth feels real. Which leaves Sarah with a familiar, nerve-racking question: Do you hire before the work arrives—or wait until the revenue is actually in the door? If she hires now, she may have to cut her own pay until the new business materializes. And there’s no guarantee it will. She still remembers the last downturn, when she had to lay off people she cared about—and she’s determined not to repeat that experience. But if she waits and the clients do sign, she risks something else: overloading her existing team, burning people out, and falling behind before she can recruit and train new hires. The pressure is even higher because Sarah has already set an aggressive revenue goal for 2026.
Plus: Jaci Russo explains why she’s adopted a different approach to planning and budgeting. Instead of guessing how much she can afford to spend, Jaci is changing the order of the math. After revisiting Mike Michalowicz’s Profit First—prompted by a story highlighted in the 21 Hats Morning Report—she’s begun setting profit targets first and forcing every other decision, including hiring, to fit around them. It’s only been a few weeks, but Jaci says the shift is already changing how she thinks about risk, growth, and what she can actually afford.
Over the past six years, Teamshares has quietly been running an ambitious experiment in small-business ownership. The company has bought some 90 businesses—promising never to sell them—and then converted those companies to employee ownership. Even amid the uncertainty of 2025, those businesses generated more than $400 million in revenue and about $60 million in profit, with a surprisingly low failure rate and unusually high employee retention. This week, Michael Brown, co-founder and CEO of Teamshares, returns to the podcast at a pivotal moment. Teamshares is preparing to go public—a move that raises obvious questions for a company built around long-term ownership and patient capital. We talk about what Teamshares has learned about buying businesses from aging owners, what employee ownership really changes inside a company, and what is likely to happen when an experiment like this collides with the public markets.
Six years ago, Kate Morgan walked away from the sale of her business just days before closing. Since then, she’s endured some rough stretches, fighting through the pandemic and a slump in the software sector where many of her clients live. She’s managed to stay profitable, and she sees lots of opportunity ahead, but the grind has worn her down. After years of pushing, adapting, and holding on, she says she’s had enough. She believes a strategic sale makes the most sense, and she’s working her network to find the right buyer. This week, she talks through her plan with David C. Barnett and Ted Wolf, two owners who—unlike most—have actually sold businesses and lived with the consequences. They push Kate to think carefully about her options and the pitfalls that trip up so many owners.
Plus: One reason Kate is ready to sell is that she’s recently published a book, and she’d like to devote more time and energy to accepting speaking opportunities. As it happens, Ted has written two books that he’s trying to figure out how to get published. Kate and David compare notes on the very different paths they’ve taken—David self-publishing through Amazon, Kate paying a big fee to work with Forbes Books. Both are quite happy with the choices they made.
This week, Gene Marks makes the case for optimism. There are all sorts of obvious issues to be concerned about but Gene cites a series of reasons his clients are expecting good things. Chief among them are a series of tax cuts that are coming on line and that are likely to provide more stimulus than many people are expecting. He also expects inflation to moderate and interest rates to fall enough to help out the housing and construction industries. Plus: What business owners need to know about the new tax rules governing over-time and tips.
Most business owners say they do. They tell themselves they just need to get through this one crisis, this one launch, this one quarter—and then life will settle down. But what if that’s not actually the goal? This week, Mel Gravely, Lena McGuire, and Ted Wolf talk candidly about what it really takes to build a business—and about whether balance is something owners are truly striving for or simply something they feel they’re supposed to want. “I gotta tell you,” says Mel, “I just don't know if people were really honest that they'd say that they'd be one to spend their time at their kid’s parent-teacher conference.” Lena stresses that it’s not about right or wrong. It’s about owners making the choice that’s right for them. “You have to make yourself happy first,” she says. “It’s kind of—we always use that, ‘Put your oxygen mask on yourself first, and then you can help others.’” The owners agree that there’s a seasonality to entrepreneurship. There are periods when the business demands more, and owners have few real options. That pressure can intensify when a company is struggling—but, intriguingly, it can be just as intense when the business is growing fast. Of course, all businesses endure periods of crisis. But what if the crises never end?
Show Notes: Here's the Josh Patrick column we discuss. It's well worth the read.
This week, Karla Trotman, owner of Electro Soft, a contract manufacturing business outside of Philadelphia, talks about the series of contradictions and tough calls she confronted in 2025. It started with the chaos of the tariffs, which you might think would have helped a domestic manufacturer but which led to suppliers charging more and to customers pulling back and to Karla feeling beaten up by her advisory board, which wanted her to reduce expenses and headcount.But Karla chose a different path.
For years, business owners have been told to follow a familiar playbook when it comes to hiring: Take your time. Be selective. Hire slow, fire fast. But more and more owners are discovering that those rules don’t fit the reality they’re facing right now. This week, William Vanderbloemen says employers can no longer indulge the luxury of hiring slow. “The shortest sermon I’ve got,” says the former pastor, “is candidates are more fickle than ever, and owners need to realize that.” Paul Downs says he’s trying to figure out what’s gone wrong with his hiring process: Is it the way he uses Indeed? The way he approaches candidates? Or the differences between hiring white-collar and blue-collar employees? Jaci Russo believes companies should always be marketing their brand as an employer and always be on the lookout for good people—even when they’re not actively hiring. Plus, in a wide-ranging, end-of-year discussion recorded in December, the three owners talk about whether they hit their numbers in 2025, whether they use a formal budgeting process, what they expect in the year ahead, and how far out they can realistically see when they try to plan for the future.
This week, Adam Russo, co-founder and owner of The Phia Group, explains how his company helps employers reduce their healthcare expenses. The key, he says, is to educate and incentivize employees to be smarter about how they purchase health care—without compromising on the quality of the care. That, he says, is how he’s able to offer employees who’ve been with Phia for five years care that is entirely free: no deductibles, no co-pays. Many of his clients are big companies that self-fund their health insurance, but he says even businesses with as few as two employees can find tremendous savings this way.
This week, we take another look back at the conversations we’ve had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges, including Laura Zander on how she got the price she wanted to sell Jimmy Beans Wool, Liz Picarazzi on her confrontation with a grizzly bear, Jay Goltz on why he just might be a good candidate to turn his business into a worker cooperative, Mel Gravely on why he sold his facilities-management business as soon as it became profitable, and Jaci Russo on how she figured out how to train a series of AI agents to deliver 10 client leads first thing every morning.
This week, Gene Marks tells us it’s late, but it’s not too late to reduce this year’s tax bill. There are still steps you can take, including writing off receivables and inventory and kicking money into a retirement plan. You might even be able to save money on your taxes from previous years if you used the research-and-development tax depreciation. The GOP tax law allows you to go back and retroactively take the full R&D deduction in the first year rather than amortizing it over five years—but check with your accountant. Gene also says that it’s no longer a slam dunk that a pass-through structure is best for smaller businesses—but again, check with your accountant!
This week—and next week—we take a look back at the conversations we’ve had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges, including Paul Downs on how he diced which employees to lay off, Jennifer Kerhin on asking ChatGPT to review her performance as CEO, Kate Morgan on why she’s been reluctant to raise her prices, Liz Picarazzi on her search for a domestic manufacturer for her trash enclosures, Ari Weinzweig on why Zingerman’s charges so much for a hamburger, and David C. Barnett on why your business is probably worth more to you owning it than selling it.
As the year comes to a close, I often reach out to John Arensmeyer, who is founder and CEO of Small Business Majority, to get his take on the state of small businesses in America. The picture John paints this year, based on his own observations as well as a recent survey, is not pretty. He points to a host of issues -- health insurance, tariffs, immigration, cuts to federal programs -- every one of which can represent an existential threat to a business. John does note, however, that through it all, owners appear to remain surprisingly optimistic heading into 2026—even if that optimism speaks more to the resilience of business owners than it does to the economic outlook.
This week, special guest Rich Jordan takes us inside a marketing challenge presented by his successful acquisition of home services businesses. Do you keep the legacy names of those businesses to preserve local trust—at the cost of running a fragmented, inefficient marketing operation? Do you take the strongest brand you own and roll it out everywhere, even if it may not translate from one community to the next? Or do you wipe the slate clean and create an entirely new brand to unify the whole operation—knowing that it means walking away from money you’ve already sunk into branding your biggest location? In a conversation with Shawn Busse and Jay Goltz, Rich walks through how he wrestled with those choices, why he ultimately made the call he did, and what he learned along the way. His takeaways included that there are still people who listen to radio, that an authentic story can compete with private equity, and that it is possible to find a marketing agency that will align its interests with yours.
Most business owners know they should build a forecast for 2026. But many won’t—because it feels intimidating and time-consuming, and let’s be honest, it’s almost guaranteed to be inaccurate. This week, Tracy Bech, founder of The 60 Minute CFO, makes the case for why you should do it anyway. Tracy breaks the process down into three simple steps, shows how even a rough forecast can change the way you run your business, and explains how her free 60 Minute CFO Custom GPT can speed things up and expand your financial analysis. Her point isn’t that you can predict the future. It’s that you need a clear, flexible model to see whether your business is on track—or drifting somewhere you never intended to go.
This week, in Episode 273, David C. Barnett, Paul Downs, and Sarah Segal tackle health insurance, one of the least enjoyable issues business owners confront. It’s renewal season, and the three owners are seeing different systems, different pressures, but similar frustrations. Paul tells us he’s facing the largest premium increases he’s seen since the Affordable Care Act—double-digit hikes that will cost him an extra $15,000 to $25,000 next year. Sarah hasn’t received her numbers yet, but she’s preparing for the worst. And David gives us a cross-border view from Canada, where universal coverage eliminates the pricing drama but introduces its own set of complications. It’s a candid conversation about what’s responsible, what’s sustainable, and what business owners are supposed to do when the numbers don’t leave good options. Plus: We also talk about what it takes to get a business ready to be sold. While BizBuySell recently reported that more owners are looking to get out—even if it means dropping their asking price—that’s not exactly what David is seeing in the marketplace. “The truth is that small businesses sell for relatively low multiples of cash flow,” he says. “And so, the real benefit is not actually in the exit. It's in the owning.”
This week, Brandon Gray, a partner with CRI Simple Numbers, talks about how his firm tracks the performance of what he calls the entrepreneurial economy. As we all know, what’s happening on Wall Street doesn’t always reflect what’s happening on Main Street, which is why Simple Numbers tracks the performance of 100 smaller businesses. Right now, Brandon says, the performance of those businesses isn’t looking great, which doesn’t necessarily bode well for 2026. How should an individual owner make use of that information? Brandon has some suggestions.
This week, we’re replaying one of my favorite conversations of the year, a Q&A session we recorded in May at our 21 Hats Live event in Ann Arbor, Michigan, with Ari Weinzweig, co-founder of Zingerman’s Community of Businesses. If you’ve already listened to our conversation with Ari, I encourage you to listen again. It’s worth it.
And if you haven’t heard it, well, you’re in for a treat. Much of the discussion focused on a topic that haunts just about every business owner, and that’s pricing. Specifically, Ari talked about how he learned to charge enough to run a healthy business and why he’d rather go out of business charging what Zingerman’s needs to charge than go out of business never knowing whether customers would have paid the true cost of great food and great service. (Spoiler alert: They have not gone out of business.)
Not surprisingly, the 21 Hats Live participants had lots of questions for Ari, including how he and his partners decide whether to launch a new business, how he and co-founder Paul Saginaw have maintained their partnership for more than 40 years, how he and Paul are approaching succession, and whether he thinks of himself as successful, which prompted Ari to share that his mother never stopped pleading with him to take the LSAT. You know, just in case.
We’re re-playing the episode in part because we took Thanksgiving week off from recording but also because it offers a little taste of what it’s like to attend a 21 Hats Live event. As you may have seen in the Morning Report, I’ve just announced that our fourth annual in-person event will take place in Cincinnati in May. Once again, it will be a terrific opportunity to connect with others who understand what it takes to build a business. If you’ve ever wished you could spend more time with people who really get what you’re going through, this is your chance. We will have peer group conversations on topics you help pick. We’ll get VIP tours of iconic local businesses. We’ll eat good food. We’ll build relationships. And we’ll leave inspired.
But spots are limited. For more information and to register, please check the newsletter I sent out on Sunday. Or shoot me an email, and I’ll make sure you get the invite. You can reach me at loren@21hats.com.
This week, Rob Levin, who is co-founder of WorkBetterNow and who has just published a new book, the “New Talent Playbook,” talks about what he considers to be a talent crisis for small businesses. As Rob points out, you might think hiring would be easy these days given all of the recent corporate layoffs—but the people leaving big businesses are probably not the right hires for smaller businesses. Instead, Rob offers a step-by-step approach that emphasizes building a healthy culture where people want to work.
This week, in Episode 272, Liz Picarazzi and Jaci Russo compare notes with Ted Wolf on their very different journeys to integrate generative AI into their businesses. For Liz, it’s been frustrating. She resisted AI at first—but while she’s ready to go now, her COO, who also happens to be her husband, still isn’t there. That’s one reason Liz says she feels as though she’s been spinning her wheels. Jaci’s path couldn’t have been more different. She jumped in more than two years ago, took every course she could find, and now has custom GPTs talking to custom GPTs talking to custom GPTs. The AI tool she built delivers 10 fresh, fully vetted prospects to her inbox every morning. “It will find the person in charge of marketing,” she says. “It will find their LinkedIn profile. It will find the company website. It will find their competitors.” And it has already produced two new clients. Plus: As this especially challenging year winds down, Liz, Jaci, and Ted reflect on where their businesses hit expectations and where they fell short. Jaci notes a sales hire that failed. “I would have liked to have not spent the money on that person and had this epiphany without the pain,” she says, “but I think those two things just go hand in hand.” Liz cites her $400,000 tariff bill: “It really hurts, and it makes me angry,” she tells us. “But in terms of revenue, we’re doing well, I gotta admit. Thank God for New York City rats and trash.”
That’s the conclusion of Ilana Preuss, who is founder and CEO of Recast City and who believes that the way to bring back America’s Main Streets, downtowns, and local economies is through small-scale manufacturing. While traditional economic development focuses on what Preuss calls big-game hunting--recruiting big, established companies--she favors looking for ways to support even the smallest of businesses. How can a community do that? Step one, she says, is to find local manufacturers, talk to them, and find out what they need. Go figure!
This week, in Episode 271, we welcome another new voice to the podcast: Channon Kennedy, who takes us inside the side hustle that’s become her second full-time job. Channon is the inventor and patent holder of the Morgan Square, a clever measuring tool—here’s a demonstration—that’s racking up awards, expanding its distribution, and carving out space for a woman founder in a traditionally male-dominated industry. This is a true bootstrap story. Channon’s numbers are modest enough that she still does most of her own fulfillment at night after her day job as a banker—and she loves it. “Every time I get an order,” she says, “I feel like I'm wrapping a Christmas present. I'm just so excited that somebody wants something that I've created.” Plus: Paul Downs checks in with an update. After posting his best year ever in 2024, he was blindsided when sales suddenly stalled earlier this year, forcing him to lay off a third of his employees. Sales have since rebounded, but now he’s staring at a backlog and a different dilemma: Does he hire aggressively to meet the higher demand—or play it safe until he sees how 2026 begins?
Yes, says Gene Marks, it’s easy to make fun of all of the ways in which AI chatbots can fail (don’t even think about asking them to create an image of a Yorkshire Terrier hitting a homerun), but that’s no excuse to sit on the sidelines. Get the paid version. Get some training. Get your employees some training. And get to work. On what? Gene gives some examples of his favorite use cases.
This week, in Episode 270, we dig into employee ownership with two people who’ve lived it: Kris Maynard and Justin Jordan of Cathedral Holdings, a 100-percent employee-owned ESOP since 2011. Kris and Justin are enthusiastic proponents of ESOPs, but they’re also candid about what can go wrong. Yes, ESOPs come with big tax advantages. But the transaction can be complex. The debt can fundamentally change the risk profile of a business. And perhaps the most under-discussed challenge of all: not all employees embrace employee ownership. Some see it as little more than a glorified retirement plan. And here’s the thing: an ESOP can be a far riskier retirement plan than many understand. They differ from 401(k)s in that there's no regulation requiring an ESOP to sequester its employees’ retirement funds. If the company fails—and like all businesses, ESOPs do fail—those nest eggs can vanish. Kris and Justin explain how they’ve addressed these issues and what they might do differently if they were starting over. They also emphasize an important point: Not all ESOPs are created equal. “If you’ve seen one ESOP,” Justin likes to say, “you’ve seen one ESOP.”
This week, Julian Scadden explains how the organization he runs, Nexstar Network, helps the owners of plumbing, HVAC, and electrical firms become better business owners. Along the way, he discusses the challenges home-service businesses are confronting, why Nexstar is member-owned (and what that means), and an intriguing decision he made recently to part ways with the 30 percent of his members who are private-equity backed. Those members represented half the organization’s revenue at the time of the decision. I also ask Julian which is the better path: learning a trade and building a business or buying a business and figuring out the trade.
This week, in Episode 269, we welcome Ted Wolf, co-founder of Guidewise, as the newest regular member of the 21 Hats Podcast crew—and Ted arrives with a pretty good story. Back when he was building his IT staffing business with his brother, a senior employee walked out. But he didn’t walk out alone—he took key employees, key accounts, and 40 percent of the company’s revenue. At the time, Ted thought it was the worst day of his business life. Turns out, he says, it was his best. Because that disaster forced him to rethink everything—how decisions get made, how profits get shared, how responsibility gets distributed. And that shift led not only to healthy growth but eventually to the kind of exit business owners dream about. That experience continues to inform the work Ted does today, helping companies integrate AI into their operations. The hard part, he tells Jennifer Kerhin, isn’t the technology—it’s the people. It’s managing the change, the fear, the implications. The technology matters, too. Ted and Jennifer also discuss whether small businesses should try to retrofit AI into their current tech stacks—or whether the smarter move, painful as it may be, is to start fresh.
Josh Patrick’s first act was building and eventually selling a successful vending-machine business. His second act was building a thriving consulting practice in which he helped other business owners learn the lessons he’d learned the hard way. In our latest Dashboard episode, Josh, a cancer survivor whose cancer has returned, is exploring two experiences—retirement and death—that he believes most owners are ill-prepared to confront. He’s planning to address that in his writing. As for himself, Josh tells us that he’s not afraid of death, but he is afraid of retirement.
This week, in episode 268, Jay Goltz, Lena McGuire, and Liz Picarazzi discuss a common concern: When does it make sense to buy a building for your business? Under the right circumstances—say, with an SBA loan, a good location, and a little luck—the real estate could end up being worth more than the business itself. But what if the business is just getting started? Or what if the owner is nearing retirement age and may not be around to reap decades of appreciation? Is buying the business still a good idea? Meanwhile, Liz and Lena also compare notes on their ever-evolving tariff challenges. One thing Lena has observed is that some owners in her industry have just had it. They don’t want to deal with the uncertainty, and they’re just packing it in: “We're going to see who survives all this,” she says, “and I want to be a survivor.” Plus: Liz has her first “aha” moment with an AI tool her team built, one that’s already helping convert sales.
This week, Greg Shugar, owner of Beau Ties, a men’s accessories business, explains how the tariffs have the potential to destroy the very businesses they are supposed to protect. As Shugar points out, President Trump has said all along that if you make it here, you won’t have to pay the tariffs. Well, Beau Ties makes it here -- but it has to import fabric from overseas because the silk fabric it needs is simply not produced here. And those imports are being taxed at a very high rate. At the moment, Shugar is waiting to hear whether Trump will indeed, as he has threatened, slap an additional 100-percent tariff on imports from China, which Shugar says could force him to shut down. The threat alone means that he can’t make plans two weeks out -- let alone start thinking about next year.
This week, in episode 267, David C. Barnett, Kate Morgan, and Sarah Segal tackle a challenge every owner who sells services eventually faces: Clients want to hire you, but you want them to understand they’ll mostly be working with your team. How do you make that clear without scaring them off? For some, it’s a delicate balancing act. For Kate, it’s simple: if a client insists on her personal time, she charges, in her words, “a boatload of cash.” Plus: we dive into another tricky owner decision: how to structure bonus plans that truly drive retention. David is weighing a deferred bonus approach, where payouts happen over several years. It’s a proven way to keep people around, but he wonders: Do you really want employees who’d otherwise leave to stay just for the money? Also, when valued employees get an offer, do you counter-offer? And if they leave, do you tell them they can always come back?
This week, in episode 266, David C. Barnett, Jay Goltz, and Kate Morgan wrestle with one of the trickiest challenges for business owners: how to give employees room to grow without losing sight of the company’s mission. David points out that every business is on its way to obsolescence unless it deliberately evolves—and one way to do that, he says, is by letting employees experiment and try new things. That approach, Jay says, is exactly what led to his building a furniture business. Plus: Kate and Jay agree that while many aspects of running a business can be stressful, nothing has been more stressful for them than the period when their businesses were growing the fastest. And the owners react to a Reddit post from someone who has found that hiring employees has created more problems than it has solved. “Is this just what having employees is like?” the owner writes. “Please tell me I'm not the only one losing my mind.”
This week, Ted Wolf, who co-founded Guidewise, which helps businesses manage change, offers a slew of valuable AI suggestions for business owners, regardless of how big or small their businesses are and regardless of whether they’re just getting started or they’ve already taken the leap. Those suggestions range from how much to pay for an AI tool to how to protect your data to how to ease employee resistance to how to figure out where to begin. Here’s one step you can take right now: Ted explains how to use ChatGPT to do an instant SWOT analysis comparing your business’s performance with your competitor’s.
This week, in episode 264, David C. Barnett and Jennifer Kerhin say they’re already making plans for next year: adjusting pricing, conducting employee reviews, and setting budgets. In the past, Jennifer has chosen to restrain growth to give her employees and her processes a chance to catch up. But this coming year? She says she’s ready to “unleash the hounds.” And for the first time, she’s planning to budget for profit first and then force her expenses to fit her margins. Unlike Jennifer, who conducts employee reviews throughout the year, David saves his evaluations for the end of the year. As he looks forward, he’s trying to figure out what the economy means for his business. He’s seeing more companies in distress, but also more opportunities to help people with severance packages who decide to buy businesses. Plus: David and Jennifer share how they’ve each been experimenting with ChatGPT of late.
This week, Kurt Wilkin discusses what he’s learned about selling businesses and how he’s thinking about what he might do next. An entrepreneur, an investor, a mentor, and a former business owner who recently sold a recruiting firm, Wilkin tells us why his acquisition of the firm didn't work out the way he hoped and how he managed to turn it around and sell it. Part of the problem, Kurt says, was that he jumped back into the game too quickly after selling his previous business. It’s a mistake he’s not going to repeat this time.
This week, in episode 264, Mel Gravely brings closure to a story he’s been sharing in pieces over the past year. You may recall that he bought a facilities maintenance company a couple years ago that he was convinced he could scale—only to discover that it was hemorrhaging money. Mel dug in, diagnosed the problem, fixed it, bought out his partners, turned the company profitable—and then decided to shut it down. Why close a business that’s making money? Mel explains the surprising answer, along with three lessons he says he learned. He also joins Jay Goltz in a candid discussion of the painful flipside of hiring: When, and how, does it make sense to lay off employees? As Jay points out, it’s far easier to find advice about adding people than about letting them go, even though it’s a calculation many owners are facing today. Plus: A would-be entrepreneur preparing to launch a business with two friends admits he’s feeling scared. He wants to know whether that fear ever goes away. Mel and Jay think he’s asking the wrong question.
This week, Cameron Madill, an entrepreneur who’s married to an entrepreneur, talks about the challenges of building a business while maintaining a relationship. Along with his own experience, Cameron has done lots of research, including interviewing more than 100 couples, and has also started a business to help couples balance marriage and entrepreneurship. Among other things, we discuss the difference between healthy passion for work and unhealthy passion, how to handle the most common issues that come up between entrepreneurial spouses, and the most important lessons Cameron has learned on this journey.
This week, in episode 263, we bring you another 21 Hats Brainstorm. Elan Daniel, who started a small-batch hummus business inspired by a memorable experience in Israel, is trying to figure out his best path to long-term viability. So far, he’s been selling at farmers markets and direct to consumers, making all of the hummus and all of the deliveries himself. Since February, his sales have been growing between 5 and 10 percent a week, but his growth is constrained by his refusal to use preservatives, which adds flavor but limits the product’s shelf life. So how should he proceed: Should he sell to speciality markets and restaurants? Should he try to sell to Whole Foods? Should he open his own hummus restaurant, or hummusiya? Should he try to introduce his hummus to the uninitiated or should he focus on connoisseurs? To help Elan think through his options, we convened a panel of 21 Hats Brainstormers and recorded this podcast episode. It’s brought to you by New Bridge Studios, which helps companies, creators, and causes connect their story to the bottom line. And by the way, if you have a challenge you’d like to put before a panel of business owners in our next Brainstorm, shoot me an email: loren@21hats.com.
This week, Eric Stites, founder and CEO of Franchise Business Review, talks about the state of the franchising world. How much money do you need to buy a franchise? How much can you make? What are the hot categories? What are the most common mistakes? We also talk about life on the other side: What makes a business a good candidate to become a franchisor? And is it possible to avoid the tension -- and litigation -- that so often arises between franchisees and franchisors? Plus: If you buy a franchise, are you an entrepreneur? Or are you just buying a job?
This week, Jaci Russo and Sarah Segal wrestle with a question that haunts many entrepreneurs: How do you bring your kids into the business—whether for a summer or for good—without messing up the business (or the kids)? For years, Jaci and her husband Michael quietly hoped their son Jackson might one day take over their marketing agency. Their unusual strategy? Never mention it to him—at least not until he’d demonstrated interest and not until he’d proven himself somewhere else. The approach seems to have worked: Jackson has joined BrandRusso, and Jaci has told him he’ll take over in four years. Which prompted Sarah to ask Jaci an obvious question, “What happens if he takes over, and he does a bad job?” As it happens, Jaci and Michael have thought about that, too. Plus: Jaci and Sarah discuss the merits of the new tech trend, especially hot in San Francisco, where more and more people are wearing AI-powered devices that can stealthily transcribe every conversation they have.
This week, Shawn Busse, founder of Kinesis, talks about finding ways to market authentically when so many of the standard tools of marketing are in flux. In Shawn’s case, that means holding an annual event where business owners -- and potential clients -- have the opportunity to come together to learn and interact in person. Of course, throwing such an event costs money. It’s a lot of work. And it’s not always easy to strike the right balance between education and promotion, but Shawn believes more businesses should try it.
A few months ago, John Abrams—author of From Founder to Future—joined us to talk about succession strategies and the different ways business owners can share ownership with employees. For his own business, John chose one of the more radical options: he turned his construction firm into a worker cooperative. Perhaps surprisingly, the more he described the co-op model, the more intrigued Jay Goltz became—although, predictably, Jay did retain a degree of skepticism. So we asked John to come back on the podcast to help Jay dig a little deeper: Are co-ops really all about democracy? Does someone on the loading dock get the same vote as the CEO? How do profits get split in the co-op model? How do losses get absorbed? How are loans secured without burdening frontline workers with personal guarantees? And perhaps most important: What can go wrong? In the end, I think surprising even himself, Jay failed to identify any real dealbreakers.
Show Notes:
Get a free trial of the Morning Report.
Learn more about the Cooperative Fund of the Northeast.
This is the podcast episode where Jay Goltz talks about how to do a We-SOP.
This week, Gene Marks makes a surprising claim: his business is “unsellable.” Never mind that it’s profitable. Never mind that it gave him the freedom to live the life he wanted and that it has left him and his wife financially secure for retirement. According to Gene, the business can’t be sold because it’s too dependent on him and because it has no IP, no exclusivity, and no moat. But is he right? Aren’t those the same challenges faced, for example, by countless HVAC and plumbing companies that private equity firms buy every day? Couldn’t Gene make his business sellable if he wanted to? What do you think? Is Gene leaving money on the table? Or has he just chosen the path that’s right for him and for his family?
In a few weeks, I’ll be in Portland, Oregon, for Shawn Busse’s always terrific Catalyst event. That trip has had me thinking about the city’s keep-it-weird ethos, the spirit that’s made Portland a hotbed for creative business building. My upcoming trip has also inspired me to revisit a podcast conversation Shawn and I recorded in early 2024 with Jenelle Etzel, who is founder of Living Room Realty. The boutique real estate agency has more than a hundred brokers and a reputation for doing things differently, but Jenelle didn’t set out to be a business owner. In fact, she majored in weaving (Shawn, for the record, majored in ceramics). She fronted a punk rock band. She lived out of a van. And yet, those experiences—especially learning how to manage people who didn’t technically have to listen to her and how to serve customers who’d been ignored by the mainstream—turned out to be perfect preparation for building a thriving business in a quirky city. It’s a story that says something about Portland, but even more about the unconventional paths that can lead to successful entrepreneurship.
It was around Memorial Day in 2022 when Coca Cola stunned the beverage world by announcing it was shutting down production of Honest Tea. No one was more surprised than Seth Goldman, who had co-founded the brand and sold it to Coke. But within two weeks, he’d decided to do it all again, and by that Labor Day, bottles of his new venture, Just Ice Tea, were already landing on store shelves. And now, three years later, Just Ice Tea has exploded from $1 million in annual revenue to nearly $24 million to rank 88th on the latest Inc. 5000—more than two decades after Honest Tea first appeared on the list. Which makes this the perfect moment to revisit the conversation I recorded with Seth right before Just Ice Tea launched. In it, he shares how he processed Coke’s decision, why he sold to Coke in the first place, what compelled him to get back into the business, and what he learned working inside the world’s largest beverage company. And yes, I asked whether he could imagine selling this brand to Coke, too.
This week, Jimmy Kalb tells us how he built his electrical component business and, perhaps even more impressively, how he put a plan in place that has allowed him to walk away from his CEO role at the relatively young age of 63. One key: Jimmy has long been a process guy. For years, he’s been creating processes and handing them over to someone else to manage -- until he left himself with not all that much to do. Another factor: He only hires people right out of school, which is why his successor is in his early 30s and has never worked anywhere else.
This week, in episode 260, Liz Picarazzi tells Jay Goltz and William Vanderbloemen that she’s had a couple of big breakthroughs. For Liz, it’s been a challenging few years dealing with the tariffs while also trying to break into a promising new market. Despite the advice of some very smart people who encouraged her to conquer her first market —urban areas plagued by rats—before expanding into additional markets, Liz has spent several years trying to position Citibin to serve towns, parks, and resorts that need trash bins strong enough to withstand bears. For that investment to pay off, however, Liz would have to outsmart her nemesis, an especially ferocious competitor that goes by the name of Seeley. Plus: Jay talks about the plight of small retailers trying to survive while their industry collapses around them. And William tells us how he’s trying to keep up in the AI arms race between employers and employees.
This week, Gene Marks explains why he -- like many other business owners -- long ago gave up on trying to promote his business through Google AdWords and why he’s hopeful that AI will break Google’s monopoly on search. That’s nowhere close to happening, but you can see the changes coming with the arrival of Google Overviews and with businesses trying to figure out what it takes to get discovered on ChatGPT. In the meantime, Gene’s placing his promotional bets on YouTube.
This week, in episode 259, Jaci Russo tells David C. Barnett and Kate Morgan how the hiring of her agency’s first top-level sales person went wrong. About four months ago, when Jaci first told us about this big step, she sounded thrilled. She said her new sales chief was a delight to be around, had hit the ground running, and had already lined up at least one impressive client. Unfortunately, none of that panned out. But Jaci, who is hardly the first business owner to have an important placement go off the rails, offered to walk us through her process to see what lessons we can all learn: Were the interviews flawed? Was the onboarding effort insufficient? Was it the executive recruiting firm she used? Was it the compensation structure? Or was it the remote-work arrangement? Plus: We also discuss the mounting evidence that companies have stopped filling entry-level positions. And should that trend continue, where will owners find the next generation of leaders?
This week, Tracy Bech explains how and why she spent six months building, training, and testing her brand new 60 Minute Custom GPT, which is essentially an AI CFO that can perform all kinds of financial analysis on your business. You can interact with it as easily and conversationally as you do with ChatGPT, and it can help you figure out why your margins are off, or how you should expect to perform next quarter, or whether that new service you plan to offer will be profitable. And it’s free.
This week, in Episode 258, Laura Zander tells Mel Gravely and Jennifer Kerhin how she and her husband, Doug, managed to sell their business for precisely the price they wanted. As you may recall, Laura and Doug started Jimmy Beans Wool more than two decades ago as a tiny corner store and turned it into one of the biggest brands in the yarn industry. Years ago, the couple decided they’d be open to selling—but only if the offer was right. With that goal in mind, they made a deliberate effort to get the business sale-ready and to keep it that way. And, as Laura ran the company, she started cultivating relationships with anyone she thought might one day be a buyer. In fact, she tells us, she was never shy about saying, “Oh, hey, Bob, it's really nice to meet you. Do you want to buy my business?” Eventually, someone said yes—although getting to a signed contract, Laura says, nearly broke her. Plus: Jennifer thought she had her hands full running her business—and then her own home went up in flames.
This week, Ben Knepler returns to the podcast to explain why he and his co-founder at True Places concluded they had no choice but to suspend production of their portable, outdoor chairs and go into survival mode. Initially, they manufactured the chairs in China, where they’ve been paying tariffs since the first Trump administration. Last year, at considerable expense, they moved production to Cambodia, which at the time was subject to no tariffs. But since April 2nd, the company has been subjected to a tariff rate that has gyrated from zero to 49 percent to 10 percent to 36 percent to 19 percent as of last week. In our conversation, Ben explains why they stopped production and how they hope to survive.
This week, in Episode 257, David C. Barnett, Jay Goltz, and Lena McGuire talk about their experiences hiring consultants, advisors, and especially coaches. There are, of course, lots of great business coaches out there, but as the owners explain, it’s easy to be led astray by coaches who don’t really know your industry or who address your specific challenges with their cookie-cutter solutions. And here’s a question: Does it matter whether the coaches were successful in their own entrepreneurial endeavors? “I've seen some of these people in the picture framing industry,” Jay tells us, “these people who were coaching and were giving advice to people. And every last one of them failed in their own business.” But when coaching works, it can be transformative, says Lena, who is “absolutely thrilled” with the coach she hired. So how do you tell the difference between a coach who can actually help and one who just talks a good game? Plus: Jay explains why he’s thinking about opening a pizza shop. Seriously. Well, sort of seriously.
This week, Peter Koehler, who helps businesses with their operations, finances, and succession planning, points out that small businesses are not just mini-versions of big businesses. In fact, he says, they’re an entirely different species, and he believes the federal tax code should treat them as such. In our conversation, he suggests a few changes -- tiered payroll tax rates, a startup tax credit to cover professional services, an expanded qualified business income deduction -- that he thinks might restrain our slide toward ever greater consolidation.
This week in Episode 256, David C. Barnett, Kate Morgan, and Sarah Segal compare notes on how they market themselves—and their businesses—online. All three are active on LinkedIn, but their strategies, investments, and even their goals are quite different. Are they seeking likes? Credibility? Clients? All three? “Sales and revenue are ultimately the metric we have to look at,” says David. “Likes and shares don't pay any bills.” Plus: Kate just spent what she calls “a boatload of cash” to publish a book. David self-publishes on Amazon—for free. And Sarah? She’s not writing a book at all. She hired a VP instead. It’s a lively conversation about what works, what doesn’t, and how small business owners decide where to invest their time and money.
This week, Sheela Murthy, who founded and built one of the most prominent immigration law firms in the country, talks about the issues business owners may be confronting during the Trump administration’s immigration crackdown. Among the questions Ms. Murthy addresses: What should owners do if they suspect an employee may be undocumented? If the owner decides to keep the employee, what’s the worst that can happen? How reliable is E-Verify? If you employ people who you suspect may be undocumented, are you helping them or exploiting them?
Last September, we hosted a 21 Hats Brainstorm podcast episode in which BaLeigh Waldrop told us that she was considering buying the family business from her parents. BaLeigh, who has been serving as chief financial officer of the Miller Waldrop furniture business that her great grandfather started, recognized that she was being offered a remarkable opportunity, but she had some concerns. Sales have been off of late, the business is predominantly brick-and-mortar, and most importantly, she would have to work out an ownership structure with her younger brother. The 21 Hats crew of owners and entrepreneurs who joined the brainstorm asked a lot of good questions and offered smart suggestions. “I think what's actually incredibly hard about this whole thing is that I love it,” says BaLeigh. “I love wearing the different hats. I love owning a business in a small community.” We left it that BaLeigh would get back to us once she’d figured things out. In this week’s episode, she returns to tell Jay Goltz and the rest of us what she’s decided.
This week, Frank Rimalovski, who is head of both the NYU Entrepreneurial Institute and the NYU Innovation Venture Fund discusses how his programs help young entrepreneurs build businesses — and why sometimes the most valuable lesson he can offer is to NOT start a business. He also talks about whether you can teach resilience, how he views the strengths and weaknesses of venture capital, and what the growing impact of artificial intelligence will be on programs like his.
This week, in Episode 254, Jay Goltz, Mel Gravely, and special guest John Abrams have a frank conversation about what business owners can do to avoid what John calls the “fat-wallets-and-broken-hearts syndrome.” That’s his term for what can happen when an owner sells to private equity and the company ends up getting stripped. Jay, Mel, and John all agree they want no part of that. They all would like to see their businesses continue on without them. And yet, in thinking about succession, they’ve chosen different paths. In a conversation sparked by the recent publication of John’s book, From Founder to Future, we discuss those choices along with such issues as: why there are so few employee-owned businesses, whether they outperform other businesses, how you can finance the sale of a business to employees, whether the employee owners of an ESOP are truly owners, and whether a worker co-op model just might work for a hard-bitten, old-school owner like Jay Goltz.
That’s what Gene Marks thinks. In this week’s conversation, Gene lists the tax changes in President Trump’s big beautiful bill that he’s happiest about, while emphasizing that what he’s really happiest about is the tax certainty that passage of the bill creates for business owners. Gene also explains why he thinks owners who complain about Trump’s tariffs have no one to blame but themselves and why he’s not all that concerned about the uncertainty the tariffs are generating, including what will happen this week when Trump’s Liberation Day pause expires.
This week, in Episode 253, Paul Downs tells Kate Morgan and Liz PIcarazzi that he recently posted a job on Indeed and got 153 resumes—more than he’s ever gotten before, which prompted some interesting questions: What does this mean for business owners? Should a job posting be more about what the company expects from a candidate or more about what the company has to offer? Do the owners ask candidates to take personality tests? If the owners get 150 resumes, do they ask ChatGPT to review them? And doesn’t it seem as if more people are looking to switch careers? “When I look at someone who's working as a graphic designer in an ad agency,” Paul tells us, “I'm thinking: This person realizes AI is coming for their job.” Plus: Liz gives us a surprisingly upbeat update on her tariff situation. And the owners respond to a Reddit post asking whether it would be crazy to start a business in the current economic environment. Paul’s response: “Don’t do it.”
This week, Tracy Bech, co-author of “The 60-Minute CFO,” tells us that she normally recommends that business owners check 14 performance measures on a regular basis. But during uncertain times like these, Tracy says, there are three in particular to keep an eye on: gross profit margin, operating cash flow, and current ratio. In our conversation, she explains how they work, what they mean, and what to do if they’re flashing red. She also says you can download a free tool to track your cash flow at 60minutecfo.com.
This week, in Episode 252, David Barnett, Mel Gravely, and Kate Morgan discuss a somewhat unusual approach to succession, which is to not sell the business. Basically, it’s about taking a step back from leadership while maintaining ownership, and both Kate and especially Mel are moving in this direction. The approach can pay off financially in part because businesses often are worth more to the owner than they would be to a buyer. Why is that? As David explains, the business that the buyer buys isn’t really the same business that the owner sells: “If you've owned the business for a long time,” he says, “the balance sheet is probably pretty strong. You've had time to earn money, pay down debts. You’ve got a good equity position. This makes the business strong, and it makes it better able to weather storms. If I were to come along and buy Mel's business, I would come together on a price, and I would pay Mel. But a good chunk of that money would probably be borrowed. Now, I would have a much weaker balance sheet than what Mel enjoys today. And a big chunk of the cash flow that he currently enjoys, I would end up giving to my bank.” Of course, this approach to succession does have some challenging elements, including finding someone to run the business. Plus: We also discuss whether it’s possible to sell a solopreneur business.
This week, Gene Marks tells us why he’s skeptical of corporate CEOs like Amazon’s Andy Jassy who have started telling employees that they are likely to lose their jobs as the company continues to adopt tools that use artificial intelligence. Gene thinks CEOs who blame AI for corporate layoffs are really covering for bad management. In fact, he thinks anyone who is already replacing employees with AI is a fool. On the other hand, Gene tells us he’s incorporating AI tools into almost every aspect of his business, and he gives us some examples.
This week, in episode 251, we meet Dan Carmody, who has gained an unusual perspective on what it takes to build a business in the United States. Dan has started and built his own businesses. He’s run community development organizations that have worked to support the growth of other local businesses. And until January, he was CEO of the Eastern Market in Detroit, which is one of the last great public markets in the country and has seen a remarkable number of businesses start, thrive, and even go national. On top of that, he’s also traveled to other countries to see how they support small enterprises. His conclusion? We’re doing it wrong. This may seem jarring given the story we like to tell ourselves about the American Dream, but as Dan explains, there are some things we could learn from other countries.
This week, Victor Hwang tells us that his organization, Right to Start, has big plans for America’s upcoming 250th birthday. Spurred largely by the widespread sense that the American Dream has lost some of its luster, Victor and Right to Start are launching a campaign to turn our semiquincentennial into a celebration of America’s entrepreneurial roots and a push to remove the barriers that make it harder than it should be to start and build a business. One key focus: finding ways to make it easier for businesses to raise capital. You can learn more here.
This week, in episode 250, we’re joined by special guest Alan Pentz, who recently stepped back from his government-contracting business to start the Owner Institute, which draws on lessons he learned the hard way to help business owners scale their businesses. In his new role, Alan has immersed himself in the world of generative AI, and he’s come to some intriguing conclusions, one of which is that AI will eliminate most B-to-B agencies—marketing agencies, public relations agencies, professional services firms. Why is that? Because, Alan says, businesses will no longer be willing to pay agencies retainers of $5,000 or $10,000 a month once they realize they can get similar or even superior work from an AI chatbot. “In general,” Alan says, “most technology waves end up with a few big winners, and most people are just roadkill.” To explore the theory that agencies are likely to be roadkill, we invited Jaci Russo, owner of a marketing agency, and Sarah Segal, owner of a public relations agency, to have a conversation with Alan. Spoiler alert: There were no tears, no threats, and no insults.
On the one hand, Gene Marks tells us this week that the GOP tax bill that has passed the House and is being debated in the Senate contains a lot of elements that should cheer business owners. Specifically, the pass-through deduction would get extended and increased, the capital-equipment deduction would go back to being 100-percent deductible in the first year, and the research-and-development deduction would also go back to being fully deductible in the first year. On the other hand, Gene believes the Big Beautiful Bill is going to be a big ugly problem for business owners. But I’ll let him explain.
This week, in Episode 249, we bring you a conversation recorded at our recent 21 Hats Live event in Ann Arbor, Michigan, with Ari Weinzweig, co-founder of one of America’s most influential small businesses. Starting 43 years ago with a highly successful college town delicatessen that they could have replicated all over the country (including for Disney), Ari and co-founder Paul Saginaw have instead built Zingerman’s Community of Businesses, a collection of 12 Ann Arbor-based, collaboratively run businesses each with its own leadership and ownership structure. Together, these businesses produce $80 million a year in revenue. They include a bakery; a coffee company; two event spaces; a roadhouse; a Korean restaurant; a mail-order operation; an international food-tour business; a publishing house that publishes, among others, Ari Weinzweig; and a training center—ZingTrain—that has shared the Zingerman’s approach to business building with more than 10,000 businesses.
In 2003, Bo Burlingham pronounced Zingerman’s “The Coolest Small Company in America.” Bo’s article became the foundation of Small Giants, his book about companies that are more intent on being great than being big. The last thing we did at 21 Hats Live was to sit down with Ari to talk about that philosophy. In his passionate responses to our many questions—responses, I should note, that include a few F-bombs—Ari explains how the Zingerman’s team decides whether to start a new business, how he and Paul made (and re-made) an especially difficult decision about expanding, how he and Paul have managed to sustain their partnership for more than four decades, how they chose a succession plan, how they know if they’re charging enough, why for many years Ari’s mother continued to believe he was a failure, and a whole lot more.
This week, Sahra Halpern, who is CEO of the Business Consortium Fund, talks about a type of lender that is not particularly well known or well understood even among business owners. The Business Consortium Fund is a CDFI, or community development financial institution. Traditionally, many CDFIs, including Halpern’s, have sought to serve underrepresented business owners who have struggled to get a traditional bank loan. In the current political climate, however, CDFIs are looking to reach a broader audience. In our conversation, Halpern talks about how CDFI lending differs from bank lending and what types of business should consider approaching a CDFI.
This week, in Episode 248, we bring you a taste of what we experienced at the recent 21 Hats Live event in Ann Arbor, where we did a deep dive into a challenge confronting Mars Chapman, owner of Casey’s New Orleans Snowballs, a snowcone business in Austin, Texas. Mars, who is 36, bought the business from his parents and also inherited from them a somewhat laidback approach to ownership. The business has been operating for 29 years, but it has generally run only eight months of the year, which has been enough, thus far, to support a comfortable lifestyle for its owners. But Mars, whose wife, Page, works for a nonprofit and who is pregnant with their first child, has begun to question whether his current approach will be enough to support a family. This is another in our series of 21 Hats Brainstorms—we used to call them Fish Bowls—in which we pair an owner facing a challenge with a group of entrepreneurs eager to help. We ask questions, break into small groups to exchange ideas, and then report back. Sometimes—as I personally experienced at last year’s 21 Hats Live event—the comments and suggestions can be challenging, even a little painful to hear. But they’re always constructive.
This week, Lance Tyson, founder of the Tyson Group sales consultancy, talks about how he’s using generative AI in his own business along with his suggestions for owners who are just getting started with AI. Among his suggestions: ask ChatGPT how best to use ChatGpt. Lance also talks about how salespeople can best navigate a business environment struggling with tariffs, uncertainty, rising prices, and talk of recession. One tip: don’t just accept an email rejection. Try to get them on the phone.
This week, in Episode 247, we welcome a new regular, Kate Morgan, who joins the podcast along with Paul Downs and Jay Goltz. Kate is the CEO and founder of Boston Human Capital Partners, which provides recruiting and HR services, mostly to other small businesses. After a very difficult stretch caused by the pandemic, Kate’s business has been growing again – but Paul and Jay think she’s leaving money on the table. They think she needs to raise her prices. “I mean,” responds Kate, “we're growing in an industry that we're seeing shrinking right now, and so it's one of these things: Do I want to scare the squirrels and jump up our prices? That's where I've been struggling.” Plus: Are HR people supposed to protect the employees or the business? And after having to lay off a third of his workforce, Paul gives us an encouraging update on how his business is doing.
This week, John Arensmeyer, our man in Washington, reports on what small business owners need and what they are likely to get from Republicans and Democrats. The issues -- tariffs, access to capital, taxes, health care -- are tricky, but John says there have been some recent examples of legislators coming together to support small businesses.
This week, in Episode 246, we meet Ben Knepler, who, along with his True Places co-founder Nelson Warley, came up with an idea for an outdoor chair that they believe could be a game-changer. They liked the idea so much that they quit their corporate jobs, they raised money, they borrowed money—putting their own homes at risk—they fought through the pandemic, they found a manufacturer in China, they launched on Kickstarter, they found another manufacturer in Cambodia, and then they ran smack into the brick wall of President Trump’s second-term tariffs. Or, as George Harrison almost put it, “If you try to sit, I’ll tax your … sturdy, portable, folding chair that could create a whole new category of high-end outdoor products except you’ll probably have to try to sell them in some other country … ‘cause I’m the tariff man.”
This week, Gene Marks -- normally a fan of automating anything that can be automated — says it’s too soon to think about turning important tasks over to artificial intelligence bots, mostly because they’re still making too many mistakes. In fact, Gene cites a survey of business leaders who said they came to regret offloading employees in favor of AI. In many cases, those leaders wound up trying to re-hire their employees. Plus: Gene also talks about how businesses using AI can get into regulatory trouble if they’re not careful.
This week, in Episode 245, a new regular, David Barnett, joins the podcast along with Jaci Russo and William Vanderbloemen. David, who has been a guest on the podcast before, helps people buy and sell businesses—but, as he explains, he’s not a business broker. He’s found a different business model. David, Jaci, and William discuss why it’s so hard to sell a business, what owners can do to make their businesses more attractive to buyers, and why it can be in everyone’s interest for sellers to accept an earnout. Plus: Jaci talks about why she used a recruiter to help her hire a business development person and why she ended up choosing someone who checked none of the boxes she initially thought most important. “I thought I needed some hotshot East Coast, West Coast, big city dude who came in with all the slick talk,” she tells us. Instead, she found her winner in rural Alabama.
This week, Rob Levin, co-founder and chairman of WorkBetterNow, talks about why he sees business owners—despite the uncertain economy—still struggling to fill key roles. He also discusses the importance of creating a culture by design, how owners can manage their profiles on Glassdoor, and what he thinks of Gen Z employees. Plus: Rob explains how he’s been infusing AI into all aspects of running his business.
This week, in Episode 244, Jennifer Kerhin, Jaci Russo, and Sarah Segal talk about how they’ve been using ChatGPT. Jennifer has deputized the AI chatbot as a key advisor, feeding it all kinds of performance data and soliciting its analysis before making hiring, financial, and strategic decisions. Recently, she asked it to identify her biggest blind spots as a CEO. Five seconds later, it spat out five answers with detailed explanations and suggestions. And what did Jennifer think of the feedback? “It was right on,” she tells us. “I mean, it was totally, absolutely true.” We even brought ChatGPT into our conversation in real time, asking it whether Jaci had hired the right business development person, whether Sarah had been fully prepared two years ago to buy back her PR firm, and what’s the best podcast for small business owners. Plus: while we were talking, Jaci asked ChatGPT to evaluate the performance of her co-founder and spouse, MIchael. Let’s just say, it does have some concerns.
This week, Gene Marks highlights some recent tech developments, including: Quickbooks is selling a lifetime version of its software for just $250. Microsoft has reintroduced its somewhat controversial Recall AI tool, which captures and indexes screenshots of user activity every three seconds—a function that is intended to improve cybersecurity but that has raised some interesting questions. Plus: Gene explains how—if you have the time and money—you can now connect the various software platforms you use and turn them into a smart AI assistant.
This week, in Episode 243, Liz Picarazzi tells Sarah Segal that she’s taking another pass at finding a domestic fabricator. Maybe it’s wishful thinking, Liz says, but she’s hoping that now that her business is more established, she just might find an American factory that wants to partner with a growing business and would be eager to help her re-shore her manufacturing. She’s also decided she’s going to keep speaking out about the tariffs despite the hate mail she’s been getting: “I'm not going to be ashamed of manufacturing in Asia,” she tells us. “I had my reasons, and they were very good reasons.” Plus: Sarah talks about how she’s been using AI, including to create her own GPTs, which help her promote her clients. She’s also found a software platform she loves that makes it easier to find and file requests for proposals.
But not every business knows how and where to tell it? This week, Sarah Segal talks through what business owners should know about public relations: How can they get better at explaining what they do? How can they figure out what others will find interesting about their business? Should they share their story themselves or reach out to a journalist? If they decide to reach out to a journalist, should they do it themselves or hire a PR person to do it? If they decide to hire a PR person, how much should it cost?
This week, in Episode 242, Jay Goltz and Lena McGuire talk about an expense a lot of business owners may not even realize they’re paying. When former employees collect unemployment, they get a check from the government, but then their former employer gets docked. It can add up to real money, and that’s likely to become a bigger issue if the economy deteriorates. Of course, as Jay and Lena discuss, one way to keep your unemployment insurance as low as possible is to do a better job hiring. Jay and Lena also talk about whether it ever makes sense to rehire someone you’ve had to fire. Plus: With Lena’s clients and potential clients putting on the brakes, she’s using this slow period as an opportunity to improve her systems. She’s hoping to avoid a mistake she made last time when she built a business that she was unable to sell.
This week, Gene Marks offers some suggestions for how businesses can survive President Trump’s trade war. Those suggestions include exploring free-trade zones, raising prices strategically, scouring the world for alternative suppliers, and getting out of China. Despite all of the disruption and upheaval, Gene continues to believe that the long-term gain will be worth the short-term pain.
This week, in a conversation recorded on March 27—shortly before Liberation Day, the day Donald Trump announced his so-called reciprocal tariffs—Liz Picarazzi told Shawn Busse and Jaci Russo what it was like to get her most recent tariff bill for a shipment of trash enclosures from China. “I knew what it was going to be, because I had calculated it,” she says, “but to actually see it on paper was terrifying.” And of course it’s only going to get worse now. In our conversation, we discuss a couple of points that bear emphasis: One, Liz tried everything she could think of to find a way to manufacture her products in the U.S. It hasn’t been economically viable in the past, and it’s unlikely to become viable any time soon. And two, Liz wonders—if these tariffs really are intended to bring manufacturing back to the U.S.—why isn’t some of the tariff money being directed toward supporting that transition? Plus: it’s been widely reported that only a tiny percentage of women business owners surpass a million dollars in annual revenue. As it happens, Jaci and Liz have both done it, but why is it so rare?
This week, John Arensmeyer, founder and CEO of Small Business Majority, talks about the unprecedented crisis confronting small businesses. At the same time their business models are being upended by President Trump’s tariffs, business owners are also watching their support infrastructure get decimated by budget cuts. John talks about what owners can do to hunker down, to survive, and to make sure their voices are heard.
This week, in episode 240, Paul Downs tells Jaci Russo and Sarah Segal about laying off a third of his workforce. “Here's the problem in a nutshell,” he says. “Last year, January to March, we sold $1.356 million. This year, January to March: $680,000. March is on track to be the worst month I've had since I started taking records.” Paul also tells the owners that he used to have a rainy-day fund for such occasions, but he used it to renovate his house. He does think the layoffs and other cash savings have put him in a strong enough position to hang in there until business picks up. “We’re getting calls,” he says, “we’re just not getting orders.” He’s also trying out a digital marketing service that can identify and contact anyone who spends even just a few seconds on his website. Plus: Paul tells us that sometimes, when forced to lay off people, you learn things about your operation that you might not otherwise have known—like that you’ve been overpaying your sales tax by at least $30,000 a year for quite some time.
The problem, says David Barnett, who helps people buy and sell businesses, is that if we all hang on to our cash, we will definitely have a recession. David, who’s based in Canada, also talks about how the current disruption looks from north of the border, what advice he’s giving to people trying to buy or sell businesses, and where there might be opportunities lurking within the uncertainty.
In this week’s bonus episode, Dylan Jones shares his entrepreneurial journey, which includes serving in the Air Force, a Master’s degree in business analytics, a failed software business, and a brand new consumer packaged goods business that draws on his knowledge of military working dogs—most importantly that it can be a challenge to keep military dogs (and pets) hydrated. Jones came up with a solution and started selling it at farmers markets where he would simply announce, “Hey, I have Gatorade for dogs.” That drove interest and sales, but not enough to make money. And when his wife delivered their second child, Jones started thinking about maybe selling out his inventory and looking for a job. But then, at one of the last farmers markets he planned to attend, he ran into an investor. That led to a conversation, an investment, a reformulation, a rebrand as Lyx, and a product that is now rolling out with big aspirations, especially for a solopreneur. As Jones puts it, “We want to be the Kleenex or the Google or the Apple of dog hydration.”
This week, five years after Covid arrived and as we find ourselves in another period of dramatic uncertainty, Jennifer Kerhin, Lena McGuire, and Sarah Segal talk about the advances their businesses might never have made had it not been for the pandemic, from the technology they use, to the people they employ, to the systems they’ve created. “It was very scary early on,” says Jennifer, “but it was transformational.” Plus: Do you hire full-time employees in anticipation of more business or when the new business is in hand? And Sarah asks what she should do when a new client signs a contract and her agency goes through all of the preliminary onboarding work only to have the client walk away. Lena’s suggestion? Review your cancellation policy, but she also tells us: “My business is 100 percent up-front. I get paid, and then I do the work.”
This week, Tracy Bech, co-author of the 60 Minute CFO, tells us that for a surprising number of business owners, the answer is no, their financial statements for last year have not yet been prepared. And that’s a problem, especially in a year with so much change and so much uncertainty, because it means those businesses have been flying blind for much or all of the first quarter. Many of these owners, Tracy tells us, think that so long as they have cash in their checking account, they’re okay, but that can be a dangerous way to run a business.
This week, in Episode 238, Mel Gravely tells Shawn Busse and Jay Goltz that he believes we will eventually find out that the U.S. economy has already slipped into a recession. The funny thing about recessions is that they can start and even end before the GDP numbers make it official, which leads us into a conversation about what businesses can do to prepare for a possible recession. Mel, for example, says his team is checking in on everyone and everything: suppliers, customers, and employees. We also discuss why a lot of pricing models no longer work, why some businesses have never fully recovered from the pandemic, and how Mel turned around a facilities-management business that was losing $1 million a year. Plus: the owners discuss the relative merits of planning to fund your retirement by investing in a 401(k) vs. by selling your business.
This week, Gene Marks explains why he thinks business owners should be patient. Gene says that whatever economic pain they may be experiencing right now will be worth it in the long run, and that’s because he believes President Trump is taking necessary steps to fix the economy and level the international-trade playing field, which will greatly benefit small businesses over time. (Podcast host’s note: I do have a few questions for Gene about that.)
This week, in episode 237, Jaci Russo tells William Vanderbloemen that she’s a little surprised, given all of the uncertainty in the air, how well her marketing business is holding up. Marketing, as we all know, is often the first thing businesses pull back on. Jaci says her strong results may have something to do with the changes she’s made in the way her agency closes sales. We also get Jaci’s and William’s takes on the conversation we’ve been having about whether owners should consider their employees’ personal circumstances when making HR decisions. But our main topic today is weightier than usual: William’s wife and co-founder Adrienne recently received a cancer diagnosis and has begun treatment. Long-time listeners may recall that William has spoken in past episodes about his efforts to make sure the business can run without him. “And oh my goodness,” he tells us, “how thankful I am that we started that process so long ago.”
This week, Ami Kassar talks about why his company, MultiFunding—despite all of the talk about chaos and uncertainty—has been overwhelmed by businesses looking for help getting funding to grow. We also talk about what the Biden SBA got wrong about small business lending, what the Trump administration is likely to do with the SBA, and the important distinction between loan fraud and bad lending policy.
This week, in episode 236, Shawn Busse, Jay Goltz, and Liz Picarazzi talk about the uncertainty coming out of Washington and the stress it's putting on their businesses. Liz, for example, has had to rethink her supply chain and her pricing on an almost daily basis as the tariff situation continues to evolve. Both she and Shawn believe they’ve lost potential clients who’ve been spooked by the uncertainty. The three owners are figuring out ways to cope, but what they find most galling is that none of this had to happen. “It’s like a manufactured recession,” says Jay. Plus: We also talk about Paul Downs’ recent comments that when he had to decide which employees to lay off, he took into consideration personal circumstances such as who just had a kid and who put a down payment on a house. That’s a natural reaction, but is it a good idea? Or is it trying to play God?
This week, John Arensmeyer, CEO of Small Business Majority, assesses what he sees happening in Washington. Arensmeyer, who recently took a group of business owners to Capitol Hill where they shared their concerns with Democrats and Republicans alike, says the chaos and uncertainty President Trump has unleashed are a disaster. Along with the tariffs and indications that the economy is slowing, Arensmeyer notes that the proposed cuts to the ACA and Medicaid -- while not generally seen as a business issue -- will have a bigger impact on small businesses than many realize. Plus: with the conversation about renewing the 2017 Trump tax cuts gaining steam, Arensmeyer makes an appeal that will surprise some to scrap the 20-percent deduction for pass-through organizations. He notes that 73 percent of the deduction’s benefits go to just 4.5 percent of pass-through businesses. Instead, he proposes creating a standard deduction that would help far more small businesses.
This week, in episode 235, Jay Goltz, Lena McGuire, and William Vanderbloemen talk about their best days as business owners and their worst days. Not surprisingly, it’s the worst days that often remain the most vivid—both for the pain they inflict and the lessons they bestow. For Lena, it was the day she felt so exhausted and overwhelmed that she knew she had reached her breaking point and had to do something different. For William, it was when the pandemic hit and he had to lay off almost half of his staff in one day, over Zoom. And for Jay, it was realizing that several young employees he’d tried to lift up were just not going to make it. Of course, the most inspiring part of these stories is what the owners did to learn from them and to rise above them. And then there’s the day Lena returned from spending most of this past January unplugged to find that a whole bunch of things had fallen into place during her absence: “My business,” she tells us, “was running without me for the first time in my life. It felt so good.”
This week, Gene Marks suggests it’s time to take a look at whether there’s still a need for the Small Business Administration. Gene, who thinks the SBA has ignored its core market, would shift the agency’s disaster loans to FEMA and its smallbiz lending to the Commerce Department and get rid of most of the other programs -- programs he says most of the business owners he knows are only vaguely aware of and rarely if ever use.
This week, in episode 234, Paul Downs tells Lena McGuire that, because his business has not picked up, he has had to lay off two employees. Paul explains how he chose which employees to let go, including to what extent he considered who has just had a kid and who just put a down payment on a house. We also talk about whether Paul should start experimenting with different ways to attract business or whether he should continue to do what’s worked in the past and try to ride it out. And then there’s this: Paul has managed to do what so many owners strive to do, which is to take himself out of the day-to-day operation of his business. But what does that mean when there’s very little business coming in? How should he be spending his time now? Plus: Lena and Paul respond to a small business subreddit post from a business owner who quit a comfortable job to pursue the idea he just couldn’t get out of his head. Now, he vacillates between thinking his business is going to be huge and thinking he’s made the dumbest mistake of his life, and he wants to know if anyone else has experienced that kind of doubt. I think we know the answer to that one.
This week, at a moment when a lot of businesses are confronting chaos and uncertainty, Shawn Busse talks about how he and Kinesis survived the Great Recession, which was primarily by talking to business owners to better understand their needs and pain points. Shawn’s advice? Create a process to talk to both your existing customers and your dream customers on a regular basis. Ask them open-ended questions, including Shawn’s favorite: What would you do if you could wave a magic wand and make anything happen?
This week, in episode 233, we brought in a tax expert, Juliann Rowe of CRI Simple Numbers, to explain everything Liz Picarazzi, Jaci Russo, and Sarah Segal ever wanted to know about tax (but weren’t sure whom to ask). For example, should owners run their own compensation through payroll? Well, maybe, maybe not. We quickly learned that the answer for Sarah is different from the answer for Liz, which is why a lot of owners get this one wrong. Among the other issues we cover: Isn’t it easier for owners to pay themselves through payroll so they don’t have to worry about paying quarterly estimates? Can the owner take a draw to cover her income tax payment? If the owner isn’t running her own compensation through payroll, how much can she contribute to her 401(k)? Is it even a good idea for owners to tie up their money in a retirement account? What’s the best way for an internal bookkeeper and an external CPA to work together? And also, why did Liz, Jaci, and Sarah ask me to bring in a tax expert who is a woman? I kind of knew the answer to that one, but I decided to ask anyway.
This week, Gene tells us that he’s been spending too much time doing and not enough time thinking. So he’s made a plan to free up some time to focus on the more important, big picture issues that sometimes get lost in the day-to-day. How will he free up the time? By getting out of the office more, by leaning more into tech, and by being more deliberate about how much time he spends with customers. Plus: Gene also shares a few highlights (and lowlights) from a Microsoft AI trade show -- including the Microsoft employees who don’t trust their own AI.
This week, in episode 232, Paul Downs tells Shawn Busse and Jay Goltz why he isn’t sleeping and why he has stopped paying himself. After having his best year ever in 2024, Paul has seen his inquiries fall precipitously. His backlog of work is dwindling, and he’s concluded he needs to take some painful steps. “I'm coming to the realization,” he tells us, “that I need to do something that involves reducing staff.” Paul’s not sure why his business is off, but he suspects it may have something to do with the chaos in Washington. He also tells us that the big marketing initiative he undertook a couple of years ago, when he decided to try to reach a slightly different target market, has yet to pay off the way he’d hoped. But he hasn’t given up on it. Plus: We also address an increasingly common issue for business owners: What do you do when employees come to work high?
This week, having long encouraged small business owners to support President Trump’s pro-business agenda, Gene Marks says those policies are likely to produce a tough year for owners. In a conversation recorded shortly after the president announced that tariffs on Canada, Mexico, and China are about to take effect, Gene tells us that he thinks business owners are too optimistic about the immediate impact of the Trump policies. In the year ahead, Gene expects those policies to produce change, uncertainty, and pain. That said, he still supports the policies.
This week, in episode 231, special guest David Barnett, who started helping owners buy and sell businesses in 2008, offers some guidance on an often-misunderstood sales process. Early on, David was a business broker. “I sold over three dozen companies for other people,” he tells us, “and it was very interesting and exciting. It was also a terrible business.” So he changed business models but has continued to do pretty much the same work. As a result, he’s amassed a lot of first-hand knowledge, much of which he shares in our conversation, including: why many owners fail to think of their business as an asset, why sellers shouldn’t be too quick to reject earnouts, why buyers should consider making multiple offers for the same business, how buyers can protect against the post-purchase loss of important customers, why businesses are selling for less than they were a couple of years ago, why there may be a smarter way to buy a business than by scouring business-for-sale websites, and why there really isn’t a true market for buying and selling small businesses.
This week, John Arensmeyer—CEO of Small Business Majority and our man in Washington—stops by to talk about the Trump administration's first week and what it means for business owners. It’s very early of course, but the administration is moving quickly on many fronts and some issues, John tells us, have businesses in his network concerned. Not surprisingly, those issues include tariffs and immigration. We also talk about the fate of TikTok and this week’s confirmation hearing for SBA nominee Kelly Loeffler.
This week, in episode 230, Liz Picarazzi tells Paul Downs and Sarah Segal that after a year of anxiety, she’s eager to find out what Donald Trump is really going to do about tariffs. Whatever it is, she thinks she’s prepared enough options to survive. “If your tax rate went from 11 percent to 60 percent,” she says, “I think most of us would be pretty freaked out, and I am, but I'm a little bit less so because of this work that we've done to be ready.” Paul, meanwhile, thinks there’s some chance his business could benefit from the tariffs—although he’s far more focused on his business’ very slow start to 2025. “It’s a little bit scary, frankly,” he tells us. And Sarah has been dealing with the pain of having to let one staffer go and the disappointment of having one of her senior people choose to go.
Last week on Dashboard, Shawn Busse said he thinks that trying to make your business discoverable on AI bots is “a fool’s errand.” So, this week, I invited Sean Campbell, CEO of Cascade Insights, a market research firm, to offer an opposing view. In our conversation, Sean talks about what businesses should be thinking about and doing to prepare for the not-too-distant day when most people turn to a generative AI tool like ChatGPT to find products and services.
This week, in episode 229, Jay Goltz, Jaci Russo, and William Vanderbloemen discuss their experiences bringing in outside consultants to review their business operations. Before the holidays, Lou Mosca, who runs American Management Services, offered to have his team take a look at any of the businesses owned by the regulars on this podcast. Jaci took Lou up on the offer, and she shares here what she learned. Jay declined the offer, and he explains why he declined it. William, meanwhile, has had two experiences with consultants that went well—and one he won’t talk about. Plus: The three owners assess what they think the coming mix of regulatory changes, tax cuts, increased tariffs, and mass deportations might mean for their businesses. They also offer their views of the state laws that forbid businesses to ask job candidates about their salary histories. “I'm sorry,” William says, “but if you believe what people tell you when you say, ‘Tell me how much you're making,’ you need to stop.”
For business owners, the challenges of digital marketing seem to just get bigger. PIck a platform, any platform: the odds of success have gotten smaller and smaller. Even TikTok, where many small businesses have built followings, may not survive the month. So what’s a business owner to do? This week, Shawn Busse offers an alternative. First of all, Shawn does not believe that figuring out how to be discovered on AI bots is the answer. “I think that’s a fool’s errand,” he says. Instead of focusing on channels and tactics, he encourages owners to tell their story and build a brand. That’s not a simple task, but Shawn shares an impressive case study of an organization that, in his words, is “making its own weather.”
In this week’s bonus episode, David Billstrom and Matt Raker, two business leaders who have played important roles in Western North Carolina’s attempt to recover from Hurricane Helene, talk about what we’re still figuring out about disaster recovery. The world tends to move on pretty quickly after an event, but the economic recovery can drag on for years. And it can be especially devastating for smaller businesses. The data from other catastrophic storms, David tells us, suggest that more than half of the small businesses in the area could be gone within a year. And of course those odds are not improved when insurance companies find ways not to pay claims and when government takes too long to respond. As you’ll hear, at the time we recorded the conversation in mid-December, the U.S. Congress still had not appropriated funds to help. That did finally happen at the end of December, but it’s still tempting to ask: Shouldn’t we be getting better at this?
This week, in episode 228, Lena McGuire—in her first appearance as a regular on this podcast—tells Paul Downs and Jaci Russo about her plans to turn her hobby, remodeling homes, into a real business. In just her third full-time year of building Spóca Kitchen & Bath, Lena says she has already experienced both a quick rise in revenue and then a surprising decline, a decline she attributes mostly to marketing issues. One of those issues, she says, is that she refreshed her website and it started producing more prospects—but fewer qualified prospects. That said, Lena is off to an impressive start, having targeted a well-defined niche, having created a clear process to connect homeowners and contractors, and having demonstrated both a real need for her services and an ability to learn from her mistakes. “I don’t look at failure as failing,” she says in a conversation we recorded in December. Plus: Paul tries to explain why his revenue surged 50 percent in 2024. Now there’s a problem we’d all like to have.
This week, in our first Dashboard conversation of 2025, Gene Marks talks about why he and other owners are excited about what they think will be a more business-friendly environment this year. But Gene also warns that tariffs and deportations are likely to drive inflation higher and discourage the Federal Reserve from cutting rates, which may not produce the economic growth owners are expecting. Plus: There are big changes coming to retirement-plan rules that owners should know about.
This week, we take another look back at the conversations we had over the past year, highlighting some of our happiest, smartest, and most insightful exchanges. We discuss whose advice is worth taking, whether any business can be remarkable, which businesses should try EOS, why family businesses can be so vexing, what to do when big businesses refuse to pay small businesses, the challenges of pricing services, the backlash against diversity, and finally the remarkably moving story of the moment that propelled one entrepreneur first to get fired and then to launch a remanufacturing business that would hit $60 million in revenue in less than five years.
There aren’t many places where you can hear entrepreneurs talk about the real-life problems they are confronting right now, today, as they happen—with no guarantee of a happy ending. But those are the conversations I have every week with Shawn Busse of Kinesis, Paul Downs of Paul Downs Cabinetmakers, Jay Goltz of Artists Frame Service, Mel Gravely of Triversity Construction, Jennifer Kerhin of SB Expos & Events, Liz Picarazzi of Citibin, Jaci Russo of BrandRusso, Sarah Segal of Segal Communications, William Vanderbloemen of Vanderbloemen Search Group, and Laura Zander of Jimmy Beans Wool. They come from a wide range of industries and geographies and experiences, but they all share a willingness to talk about not just what they get right but what they’ve learned from getting stuff wrong.
This week, and next week, we take a look back at the conversations we had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges. We discuss topics such as whether the Great Resignation prompted business owners to overreact and overpay employees, whether the anxiety of owning a business ever subsides, what young couples should ask themselves before one of them starts a business, why owners find marketing so difficult, how owners can sell a business that just won’t sell, and what keeps entrepreneurs going when the going gets really tough.
There aren’t many places where you can hear entrepreneurs talk about the real-life problems they are confronting right now, today, as they happen—with no guarantee of a happy ending. But those are the conversations I have every week with Paul Downs of Paul Downs Cabinetmakers, Shawn Busse of Kinesis, Jay Goltz of Artists Frame Service, Mel Gravely of Triversity Construction, Jennifer Kerhin of SB Expos & Events, Liz Picarazzi of Citibin, Jaci Russo of BrandRusso, Sarah Segal of Segal Communications, William Vanderbloemen of Vanderbloemen Search Group, and Laura Zander of Jimmy Beans Wool. They come from a wide range of industries and geographies and experiences, but they all share a willingness to talk about not just what they get right, but what they’ve learned from getting stuff wrong. If listening to one of these highlights makes you want to hear the full episode, that can be accomplished most easily by going to 21hats.com. There you’ll find a transcript of this episode with links to all of the episodes we sample.
This week, in episode 225, Shawn Busse, Jennifer Kerhin, and Jaci Russo talk about how their businesses did this year and what they’re planning for 2025. Jaci and Shawn have been surprised by a surge of new clients in December, which they say never happens. And Jennifer is excited because she’s confident that in the first quarter she will finally exit the Valley of Death—that transitional period growing companies experience when the people and processes that made them successful stop working (AKA No Man’s Land). Along the way, the owners discuss the relative merits of promoting from within vs. hiring from without, how long it should take to onboard senior-level hires, whether it’s better to err on the side of budgeting for too little growth or too much, how they’re training employees to use artificial intelligence, and what Jennifer can do to stop spending so much time writing and pricing proposals.
This week, Tracy Bech, co-author of the “60 Minute CFO,” talks about how business owners can get more comfortable with their financials. Very few people go into business because they’re good at accounting, but that doesn’t mean it’s acceptable to throw up your hands and say, “I’m not a numbers person.” To drive a car, Tracy says, you don’t have to understand how the engine works—but you do have to know how to read a few gauges. Well, the same is true of driving a business, and she’s got a few suggestions.
This week, in episode 224, special guest Karla Trotman explains, step by step, how she has managed to navigate the challenges and opportunities that only a family business can offer. Karla grew up around a manufacturing business, Electro Soft, that her father started, but she never intended to make a career of it. Instead, she found success in corporate America, but over time, she also came to realize the true wealth-building power of owning a business, any business. “It's not a beauty salon,” she says. “It's an asset. It's not a shoe-shine store. It’s an asset.” That realization sent her back to Electro Soft, which thrilled her father. They agreed to work together for three years after which he would retire and she would buy the business. And that’s pretty much what happened—although, as Karla tells us, thanks to some family dynamics that had to be negotiated, the transition didn’t take three years. It took 11 years.
In many cases, Shawn Busse tells us this week, they do, which is why he believes all businesses should be innovating constantly. That’s a lot to ask of small businesses, many of which are just trying to make it to the next payroll, and Shawn acknowledges that there are exceptions. But if, for example, a private equity firm starts buying up your competitors and investing money in them, innovation may be your best hope. How do you get started? Shawn offers some concrete steps to consider if you want to try to think differently about what you do. Step one? Talk to your customers.
This week, in episode 223, Shawn Busse, Jay Goltz, and Sarah Segal talk about why they’re not going to hit their numbers for 2024 and what they’re expecting from 2025, especially regarding tariffs, immigration, and regulation. Shawn says his business has been producing and closing fewer leads. “Clearly,” he says, “we’ve gotta change something.” Jay doesn’t think furniture sales will recover until mortgage rates come down, and he’s bracing for tariffs and deportations that he hopes won’t actually come: “I have to believe,” he tells us, “that somebody in government is going to figure out this isn't a good thing.” Sarah, meanwhile, says her revenues are down, but she’s taking solace from the fact that she is ending the year with a stronger book of business than she ended with last year. Plus: the owners discuss what it means that a judge in Texas has blocked the new overtime law. And they offer guidance to a cafe owner who raised her prices only to get hit with another 25-percent price hike from her main supplier, leaving her to wonder whether she should raise prices again or “eat the loss and pray for a miracle.”
This week, Gene Marks tells us he’s found the next killer app for small business, and it’s not something that’s theoretical and might be ready sometime next year. It’s ready now, and it’s Google’s NotebookLM. Gene had reviewed it previously and found it wanting but took another look at the latest version and found it could do things like streamline a job search and spot anomalies in his financials. But Gene also offers a caveat for rolling out any AI app or even a CRM: if you don’t configure it right, you can run into some very big problems. Plus: he also discusses the latest in password technology.
This week, in episode 222, we bring you another Entrepreneurial Fish Bowl with Chris Hutchinson. These Fish Bowls are our virtual brainstorming sessions where we offer business owners the opportunity to pose a challenge they’re facing to a group of owners and entrepreneurs from the 21 Hats community. This time, our volunteers are Alvin Elbert, founder of A.R.E. Manufacturing, and his daughter Megan Perona, who explain that their company had its best year ever in 2022 but has seen business fall off since then. For 40 years, A.R.E. grew slowly but steadily on word of mouth. More recently, however, the Elbert family has concluded that it’s time to do some real marketing. Like a lot of owners, though, they’re a little overwhelmed by the options, unsure where to begin, and wary of wasting money. They also happen to be going through a family ownership transition. The 21 Hats brainstormers begin by asking a lot of questions, including whether the owners have invested in search engine optimization, whether they’ve gone back to some of the customers they lost to China, and whether they’ve considered hiring a marketing agency.
This week, Victor Hwang shares some surprising reasons to be optimistic about entrepreneurship in America. For one thing, Victor, who is founder of Right To Start, an advocacy group, says that he can’t remember a presidential election where entrepreneurship was as much a part of the conversation as it was in this one. For another, he points to a series of policy changes at the local level that have made it far easier to start businesses and that he believes will serve as a blueprint for other jurisdictions looking to cut red tape. As always, Victor brings news that has yet to reach most of us—including an issue he plans to address in 2025: standard lending rules that actually discriminate against entrepreneurs by making it harder for them to get a home mortgage.
In 2021, Mel Gravely wrote a book, Dear White Friend, that was aimed primarily at fellow business owners. In the book, Mel tried to make it easier for owners to have genuine conversations about race. He suggested strategies for those, perhaps motivated by the murders of Ahmaud Arbery and George Floyd, who might want to engage. He acknowledged that emphasizing diversity can be hard work. He acknowledged that some of his own efforts had failed. But he also pointed out that he himself had been, in his words, “an affirmative action baby” and that that investment had paid off for his college, his previous employers, and the city of Cincinnati. It’s been less than four years since Mel published Dear White Friend, but of course that was a very different time. This week, he talks about the backlash that has ensued and the strategies he still believes can work for those who don’t consider diversity a dirty word.
This week, Gene Marks tells us that the first really meaningful AI applications aimed at smaller businesses will arrive in the coming months. Gene does offer some caveats, including his mantra: “Never buy the first version of anything from Microsoft.” But he also offers some tantalizing examples of things AI agents will do for business owners in the very near future, like qualifying sales leads and then putting a sales rep through a role-playing exercise to prepare for a specific client. What should owners do now to prepare? “Beat up your vendors,” says Gene. “And clean up your data.”
This week, in episode 220, Paul Downs and Jay Goltz talk about the risks they didn’t see coming. While everyone knows there’s a risk that a business can fail because it just doesn’t work, there are lots of other, less obvious risks. These are not the risks you lose sleep over, but they’re real, and if you don’t manage them, you can expose yourself needlessly to a slew of problems. Because most people learn about these risks the hard way, Jay and Paul set out to create a top 10 list of them, but I think—for those of you keeping score at home—we actually hit 11. Which led Jay to caution: “I by no means am telling anybody, ‘Oh my God, I don't sleep at night. I'm worried about all these things.’ I'm not worried about them. I just keep an eye on them.” Wait, says Paul. That’s another one: “The risk is that you let this thing live in your head and that it destroys your ability to focus on what you should focus on.” Okay, so that makes 12. And by all means, please let us know which ones we missed.
This week, Gene Marks offers some timely tips on ways you can reduce your tax burden. As you probably know, it’s a good time to consider buying an electric vehicle or some capital equipment. But Gene also offers some less obvious suggestions. For example, if you’re looking to increase your employee compensation, there can be tax advantages to paying more of their health insurance coverage rather than giving them a raise. Also, if you own the business with a spouse, Gene explains how you might benefit from reallocating how you distribute the earnings. And of course, pay those estimated taxes on time.
This week, in episode 219, special guest Travis LeFever shares the unusual journey he and his co-founder wife, Amanda, have taken to build Mission Mobile Medical, which makes mobile health clinics in Greensboro, NC. That journey started with Travis partnering in a construction business by taking out 39 credit cards to borrow $250,000. The business did well, and he eventually bought out his partner, but when Travis’ father died unexpectedly, he was moved to sell the construction business and look for something more meaningful to do with his life. That extended search led him, somewhat improbably, to overseeing sales for a company that manufactured specialty vehicles, including the Oscar Mayer Wienermobile. It was there that Travis had another life-changing experience when a nurse with a federal grant asked if he could build a mobile clinic to reach patients in underserved communities. That was the spark that led Travis and Amanda to cash in their insurance policies and start Mission Mobile Medical in 2020. The company, whose remanufacturing process allows it to create clinics in less time and for less money than its competitors, expects to hit $60 million in revenue this year.
This week, Shawn Busse talks about something that everyone kind of knows but too few businesses emphasize: remarkable things can happen when businesses improve their workplace culture and let the world know about it. Shawn shares his approach to building a brand as an employer and explains why the payoff can easily be hundreds of thousands of dollars.
This week, in episode 218, special guest Rich Jordan tells Shawn Busse and Jay Goltz what it was like buying a small plumbing business in 2020 despite having very little experience with either plumbing or business—but having spent 10 years in the Marine Corps. “When I reflected on my time in service and what I did well and what I enjoyed,” Rich tells us, “it was when I was on a small team with high stakes, far forward, far from the flagpole, responsible for making decisions and sustaining ourselves and figuring things out. So when I thought about that—small team, high stakes, self-sustained—small business kind of fit that bill.” Not surprisingly, it took Rich some time to figure out what he was doing with the plumbing business, but in just four years, through organic growth and a few acquisitions—while taking no outside capital—he’s gone from three plumbers and $1 million in annual revenue to about 90 employees and $20 million in revenue. Which is why, Rich tells Jay and Shawn, he keeps moving the goalposts, reassessing just how big he wants the business to be.
This week, Shawn Busse walks us through his LinkedIn strategy: how often he writes, what he writes about, what he posts on his own page, what he posts on the company page, and how he promotes his business without promoting his business. Most importantly, Shawn explains why he believes his posting helps Kinesis attract both employees and clients.
This week, in episode 217, Laura Zander tells Shawn Busse and Jay Goltz about her approach to buying businesses. Laura says she simply recognizes that for a period of time, life will be miserable for her and for her team. That’s what happened almost a year ago when she bought two businesses that were a challenge to integrate. And now, just as things have calmed down a bit, she expects it to happen again as she eyes another acquisition. It’s also what she expects to happen as she and her husband Doug proceed with their ongoing migration to Shopify. “Our sales are going to go down,” says Laura. “SEO is going to be rough. My biggest concern, honestly, is Doug's mental health. This whole process has been so stressful for him.” Shawn, Jay, and Laura also discuss how they feel about the possibility that the 20-percent Qualified Business Income deduction could go away next year, when it’s set to expire. You might be surprised by their answers.
With the election only two weeks away, John Arensmeyer, founder and CEO of Small Business Majority, talks through what’s at stake for small businesses, including what the campaigns are saying about taxes, regulation, immigration, tariffs, and manufacturing. Plus: Given the likelihood that, regardless of who wins the White House, a closely divided federal government is likely to be with us for some time, Arensmeyer also explains what small businesses can hope for at the state and local levels.
This week, in episode 216, Shawn Busse and Jay Goltz talk about the trendy job interview strategy of trying to get beyond canned responses by asking candidates unexpected questions along the lines of, “If you were a superhero, what powers would you have and why?” Or, “What animal best represents you as a person?” Not surprisingly, Jay isn’t a big fan of those questions, and he offers an alternative strategy that features four questions of his own design. Shawn does like to ask unexpected questions, but specifically those that help him figure out whether a candidate is likely to work well with others. Plus: Shawn talks about what it was like attending the recent going-out-of-business sale of a company he had declined to take on as a client three separate times. Also, Shawn and Jay respond to a Reddit post, where a business owner asks what he can do about a large commercial client who simply refuses to pay a $40,000 bill. “Did I just learn a $40,000 lesson?” the devastated owner asks. “What now?”
This week, Gene Marks talks about the lessons business owners should take from the devastating hurricanes of recent weeks. Gene is confident that the communities will build back better than ever, but of course, not all of the businesses will make it. We’ve been reminded that disaster can strike anywhere. What should business owners do to prepare?
This week, in episode 215, Mel Gravely, Jennifer Kehrin, and Liz Picarazzi start out talking about the pain of being fired by a long-time client. “It still stings,” says Jennifer, who nonetheless surprised her team by writing a note of congratulations to the CEO of the company that took the business. The conversation moves on to the tradeoff that comes with deciding between promoting managers from within or hiring them from outside the organization: What if your people aren’t ready? What if the outsiders have more experience but aren’t as good a fit? And that leads to a discussion of how to decide when to press on with a venture that’s struggling—and when to give up on it. Not surprisingly, all three owners have some experience in this area. Of course, they also have experience with deciding when to start a business, but they have very different attitudes about risk. While Mel says he’s pretty much always ready to go, Jennifer tells us she’s been noodling on an idea she really wants to pursue for about five years.
This week, Victor Hwang talks about the remarkable road trip he recently completed in which he got a fresh perspective on the state of entrepreneurship across America. At a time when many of us are consumed with the election and politics and all of the things that divide us, Hwang, who is founder and CEO of Right to Start, a non-partisan advocacy group, met with entrepreneurs in cities and towns from Southern California, across the northern part of the country and down to Washington, D.C., and found a whole bunch of people who are working together to build things. It’s a refreshing perspective.
This week, in episode 214, we bring you another Entrepreneurial Fish Bowl with Chris Hutchinson of Trebuchet Group. As you may remember, this is a virtual exercise where we offer a business owner—or in this case a potential business owner—the opportunity to pose a challenge he or she is facing to a group of owners and entrepreneurs from the 21 Hats community as part of a brainstorming session. In this case, it was BaLeigh Waldrop who explained why she has mixed feelings about buying the Miller Waldrop furniture business that her parents own. As you’ll hear, BaLeigh has some real concerns: the business has been down of late, it’s predominantly brick-and-mortar, and she would have to work out an ownership structure with a younger brother. The 21 Hats brainstormers ask a lot of good questions, including whether the business is profitable, whether it’s been paying family members a market wage, and whether it owns the real estate. They also offer a lot of smart suggestions. Plus: it all ends with a very surprising offer from Jay Goltz.
This week, Ami Kassar, founder and CEO MultiFunding, explains how it’s almost as if these past few years we’ve run a grand experiment to see what would happen if the government gave lots of business owners more money than they knew what to do with. In many cases, the businesses got far bigger Covid loans than they could have hoped to borrow conventionally, and they got them without having to go through the standard application process. In other words, they got the money without having to develop a plan for how they would spend it. “This is not going to end well,” says Ami.
This week, in episode 213, Paul Downs, Jaci Russo, and Sarah Segal talk about how and when they start planning for next year. And here’s one happy challenge they’ve all confronted: What do they do when they don’t have the capacity to handle all of the work that’s coming their way? Do they staff up? If so, what happens if the work subsequently falls off? Do they create a backlog? Do they miss deadlines? Do they raise prices? Plus: Jaci shares an AI tool she’s been using to learn more about the decision makers her agency targets. And the three owners respond to a case study in ADA-compliance litigation taken from a Reddit post: “What are we supposed to do about this?” a business owner who has been sued for having a non-compliant website writes in the post. “I am trying not to overreact, but having my savings and my income taken from me this way is just devastating.” Jaci, whose agency builds websites, says there is a way to protect against those lawsuits.
This week, Rob Levin, says there’s a talent crisis in America, but you wouldn't know it reading most business publications. That’s because the crisis is affecting smaller businesses much more than bigger businesses. Levin, co-founder and chairman of WorkBetterNow, which provides remote workforce and virtual assistant services to small businesses, says he keeps hearing the same thing from owners who come to him looking for help. They just can’t find good people. Levin offers several pieces of advice that start with creating a culture that people want to be part of and then building your brand as an employer. We also talk about how he’s gotten his whole team hooked on using AI, in part through what he calls show-and-tell days.
This week, in episode 212, Shawn Busse, Paul Downs, and Laura Zander call on their own experiences to assess whether the EOS operating system—as explained in Gino Wickman’s book Traction—lives up to its promise of freeing owners from frustration, helping them put the right people in the right seats, and generating all of the scale they want. Laura hired an implementer to install EOS in her business years ago. Paul took more of a do-it-yourself approach, picking and choosing from the book’s suggestions. And while Shawn hasn’t tried EOS in his own business, he has seen how it works in lots of client businesses. As a result, all three have strong opinions about what types of owners and what types of businesses are likely to do best with EOS. Laura, for example, tells us: “I think it's helpful for people like me 10 years ago, who just don't know what they're doing.”
This week, Shawn explains how a plumbing job went awry -- and more importantly, what it says about the “professionalization” of the blue-collar trades. That professionalization—along with the accompanying private equity dollars and the roll-ups and the MBAs—has certainly brought benefits. But it seems there’s been a price to pay as well.
This week, in episode 211, Jay Goltz and special guests Peter Koehler and Jimmy Kalb discuss the hottest new thing in succession planning. You may recall that earlier this year Peter was a guest on an episode in which he explained how he helped Laura Anderson sell her seafood restaurant to what’s known as an employee ownership trust or a perpetual purpose trust. Both Jay and Jimmy listened to that episode and were intrigued. Both had questions for Peter. So we recorded a conversation in which we discuss what makes a business a good candidate for trust ownership. The issues we address include: Is this only for businesses that have a save-the-world type of purpose? How much does it cost to create an ownership trust? Can owners sell to a trust and still run the business as they wish? And perhaps the biggest question of all: What can go wrong?
This week, Gene Marks tries to sort through some confusion. First, he talks about Kamala Harriss’s proposal to 10X a small business tax deduction, which sounds great except that it’s not really going to help small businesses. And then he addresses the comments of a Houston CPA who asserts that small businesses have the best tax deal in America. Gene sees it a little differently.
This week, I’m replaying an oldie but goodie, an episode that Shawn Busse and I recorded with Jeff Braverman, who turned his family’s failing retail business into a thriving ecommerce business. I’m replaying this episode both because Jeff has a great story to share, with lots of takeaways, and because—well, actually, because I took a little time off last week. But listen to this: Jeff walked away from a career as an investment banker and went to work in the family’s nut store, the Newark Nut Company. “My dad and my uncle told me I was nuts,” says Jeff, but he made them an offer they couldn’t refuse. He would put the family’s snacks online—this was way back in the early dotcom days—and they wouldn’t have to pay him unless he actually sold some nuts. As it turned out, Jeff’s little internet play wound up unleashing explosive growth and consumed the business. And despite being a former investment banker, he managed to do that without taking any outside capital. Since we first published this episode Jeff has promoted himself from Chief Nut to Chair Nut.
This week, in episode 210, Jay Goltz, Jaci Russo, and Jennifer Kerhin discuss some of the systems they’ve created that have made their businesses successful. Jay established a process that helps employees diffuse conflicts with angry customers. Jaci has a process that tracks the performance of her agency’s lead-generation efforts and has helped her target clients more precisely. And Jennifer recently created a process to deal with change orders that makes it easier to walk the line between offending customers and forfeiting profits. Plus: We follow up on some issues we’ve discussed in previous episodes. Jay told us recently that he’s cutting back on his advertising spend. Is that the best response to a softening market? Jennifer told us when she first joined the podcast about her long march through what is often called the valley of death. Is she still in the valley of death? And Jaci told us at the beginning of the year that she had two big clients that were ready to sign on. Did they in fact sign on?
This week, Gene Marks notes that the two major presidential candidates happen to agree on something, which is that we should stop taxing tipped income. Unfortunately, Gene explains, it’s a boneheaded idea. Plus: Gene’s been looking into the progress that manufacturing companies are making adopting artificial intelligence applications, and he says—at least when it comes to manufacturing—the promise of AI is starting to get real.
This week, in episode 209, Shawn Busse, Jaci Russo, and Jay Goltz discuss what it takes to stand out these days, especially if your business—like most businesses—isn’t exactly the Next Big Thing. What about trash collection? What if your business is selling scrap metal? What if you happen to be one of 69 picture framers in Chicago? What’s an owner to do to stand out then? Is it enough to execute really well? Can any business make itself remarkable? Shawn, Jay, and Jaci all believe it’s possible, and they offer examples from their own businesses as well as those they’ve observed. Plus: As Google waffles about whether it’s going to kill cookies on Chrome, will business owners still be able to target customers digitally? And Jay’s not happy about a very big bill he got from his accounting firm. Should he just go ahead and pay it?
This week, Gene Marks offers some suggestions as to what it would take for the presumptive Democratic nominee to earn his vote and those of other small business owners. Suggestion No. 1: make clear that in the debate over whether to extend the Trump tax cuts she favors keeping the Qualified Business Income Deduction for owners of pass-through businesses. He’d also like to see her promise fewer regulations and more tax breaks for owners trying to sell their businesses.
This week, in episode 208, Paul Downs, Mel Gravely, and Sarah Segal talk about the tricky calculation all entrepreneurs must make between sticking to their vision and accepting advice. Sarah explains why she is reluctant to take advice from people who don’t really know the inner workings of her business, which is pretty much everyone. Paul, on the other hand, says taking advice from outsiders helped save his business during the Great Recession. And Mel talks about why he thinks every business should have a board of advisors—and why he thinks having a board would have saved him from a big mistake he made recently. But then, Paul asks: If you do have a board, can you not take its advice? Plus: Reacting to a recent post on Reddit, the owners discuss the right way to wind down a failing business, a process with which Mel and Paul have some familiarity.
This week, Gene Marks talks about three very different topics. First, he explains how helping employees find affordable health care can actually generate business growth, and he walks through the ways even very small businesses can help. Next, Gene weighs in on proposed legislation in California that is designed to keep AI models from causing catastrophic harm. And finally, he explains how a new hire just out of college helped a Chevy dealer create a sitcom parody that went viral. But did it sell cars?
This week, in episode 207, special guest Sharon Gillenwater lets us in on some dirty little secrets about Silicon Valley. She’s the founder of two businesses. The first one was backed by venture capital and then destroyed by venture capital. Despite that experience, Sharon tried to raise capital for her second business, Boardroom Insiders, a software-as-a-service marketing tool that helps businesses sell to the top decision-makers at big corporations. But this time, the VCs weren’t interested. So she bootstrapped the business with the help of an angel investor—and proceeded to learn some surprising lessons, many of which she shares in her book, Scaling with Soul. Perhaps the biggest surprise came when she sold her business and learned the happy lesson that the founder of a relatively small bootstrapped business can walk away with more money than the founder of a venture-backed business that sells for far more. In our conversation, Sharon is unusually candid about what it took to build her business, what she learned about B2B marketing, and precisely how much money she made along the way.
This week, Gene Marks reminds us once again that AI tools by and large still aren’t ready for prime time, but he does find a handful of people doing interesting things with AI—like getting a fresh take on the risks and opportunities their business is confronting. Plus: Gene and Loren Feldman discuss whether Gene is right that his business taxes will definitely go up if Kamala Harris is elected president.
This week, in episode 206, Shawn Busse, Jay Goltz, and Jennifer Kerhin talk about what it takes to plan and execute an employee retreat—especially in our post-Covid, more-remote environment. Do you go offsite? Do you take everybody? Do you delegate the planning? Do you try to measure the ROI? Jennifer tells us about the interesting responses she got when she encouraged her employees at her retreat to ask her anything. Shawn explains why he let his leadership team do the planning—and didn’t set a budget. Jay, meanwhile, offers a slightly different perspective: “My company retreat,” he tells us, “is I cut back on my advertising. That's my retreat.” Plus: How well does The E-Myth hold up as a playbook for business owners? Is it still relevant? Or was it written for a type of business that is far less prevalent today? And Jay tells us what he thinks of Wayfair opening a massive brick-and-mortar furniture store right down the expressway from his furniture store.
This week, Gene Marks explains the global tech outage: what actually happened, how seriously we should take it, and what business owners should do (but probably won’t) before the next outage. Those lessons include: 1) Try to keep some paper handy. 2) Stay calm. The internet is going to go down from time to time. 3) Have a disaster-recovery plan. 4) And if you don’t have a disaster-recovery plan, go to ChatGPT. PLUS: Gene discusses the upheaval in the real estate industry and why the CEO of an HR platform, Lattice, wound up on a subreddit called LinkedIn Lunatics.
This week, in episode 205, Paul Downs, Liz Picarazzi, and Jaci Russo discuss how they review employees and how they make the hard calls when someone is right on the cusp. The conversation starts with a couple of tricky situations that Paul is trying to think through and then progresses through several other issues: Do you use personality tests to avoid or resolve personality conflicts? Paul, Liz, and Jaci have very different takes on Myers-Briggs and the like. Do you make sure no one is ever surprised by a negative review? Do you keep mediocre performers even when you find someone who might be better? “I need to go shut the door before I say this,” Paul tells us. “I forgot to do it.” Plus: Jaci finds a use for ChatGPT. Liz may have found an alternative manufacturer in an unexpected country. And a business owner asks whether he should report a competing company that is endangering its customers and employees. Should he report them even though he believes he would face retaliation?
As CEO of MultiFunding, Ami Kassar sees a lot of small business P&Ls, and he sees how banks are responding to loan applications. And in his view, the ground is starting to shift—although he’s not sure where we’re headed. But in times of uncertainty, he emphasizes, there are always opportunities
This week, in episode 204, Jay Goltz and special guest Cathy Caroll talk about family businesses, with Jay asserting that they are even more combustible than most people realize and with Cathy offering some smart coping strategies. We start with Cathy explaining how her own experiences in a family business propelled her to write a book, Hug of War, and to become a family business coach. Why are family businesses so difficult? Well, says Cathy, it’s because you’re trying to combine a family mindset with a business mindset, which she says, is a little like “living in socialism and capitalism simultaneously.” Of course, she says, it also has to do with mixing love and money—“You’re just gonna get sparks”—and with the brutal challenge of transitioning from one generation to the next, when every decision can feel like a repudiation or rejection. Still, it was that stew of anxiety, resentment, and trauma that helped Cathy find her calling, which is to help others do in their family businesses what she could not in hers.
This week, John Arensmeyer, founder and CEO of Small Business Majority, reminds us that the State Small Business Credit Initiative is sending billions of dollars through the states specifically for small businesses. Because every state is handling the money differently and there is no one-stop shop for information, there is some confusion—but the money is real and John explains how to figure out if you’re qualified. Plus: He also explains why he’s surprised some business groups are celebrating the recent Supreme Court decisions on regulation, why his organization favors the ban on non-competes, and why he thinks the small business tax break contained in the soon-to-expire Trump tax cuts can be improved.
This week, in episode 203, special guests Laura Anderson, founder of Local Ocean, and Peter Koehler, her financial consultant, explain why Laura decided to sell her thriving seafood business in a transaction that created a business model that is neither widely known nor widely understood. It’s called an employee-ownership trust, and there are only about 50 of them in the United States. But their numbers are growing here and abroad, and for good reason. The trust model offers owners something of a choose-your-own-adventure option that can allow them to sell for a market rate in a relatively uncomplicated transaction that makes it far more likely the business will remain true to its established mission—especially when compared to selling to private equity or even to an employee stock ownership plan. Of course, there are challenges, including getting a bank to consider financing one of these deals. But in this episode, Laura explains why, with Peter’s help, she decided to trust the trust.
No, says Gene Marks, who — it may surprise you to hear — offers three main reasons he doesn’t believe business owners should panic over the U.S. government’s growing debt. That said, he does believe that we are likely to have to operate in an environment of higher inflation and higher interest rates for some time, and he says that is likely to require some adjustment in the thinking of business owners.
This week, in episode 202, Paul Downs, Jaci Russo, and Sarah Segal talk about how they wound up pitching their products and services not to consumers, but to other businesses. They all agree that selling to business is more profitable, and they all agree that it has other advantages, as well. “In general,” says Paul, “it's easier to sell to businesses because the person you're talking to, it's rarely their money.” But some aspects of selling B2B can be harder. For example, how do you break through and reach the right person at a business, especially if you’re trying to reach the owner directly? And of course, there’s always a learning curve: Selling to a big business requires a level of professionalism that can be challenging, especially early on. Plus: Sarah explains why—even though she had to lay off people last year—she’s doubling her office space this year. Jaci is exploring what policies make hybrid offices most effective. And Paul, who says he’s having his best year ever, spells out the way he calculates when it’s time to add employees, as he had to do earlier this year.
This week, Gene Marks and Loren Feldman discuss the Supreme Court’s decision, released on Friday, that takes authority to interpret laws passed by Congress away from federal agencies and gives it to judges. Whatever you think of the merits of the ruling, Gene points out, it creates tremendous uncertainty for businesses trying to comply with the law. For example, a new overtime rule is supposed to go into effect today. Should businesses start following it, Gene asks? Or wait to see what happens with pending litigation?
This week, in episode 201, we bring you what we’re calling an Entrepreneurial Fish Bowl with Chris Hutchinson. As you may remember, we recorded one of these at our 21 Hats Live event in Fort Worth, where I shared some of my challenges trying to build 21 Hats and got feedback from the group. We recorded that conversation and turned it into a podcast episode. This time, we’re doing the same thing except it will be Jaime Echt, founder and CEO of The Crafters Workshop, who is going to explain her challenges to a virtual group of 21 Hats entrepreneurs. As you’ll hear, Jaime’s challenges are real: Her sales are down. Her customers are aging. Her lease is up. And she’s not sure what she should do next. We’re going to see if a group of 21 Hats Founding Members can offer some support and advice.
Companies don’t like to admit it, says Gene Marks, but that’s kind of the point. So far, it’s mostly big companies with millions to spend that have been able to replace humans with bots, but he believes smaller businesses will soon be doing the same thing. Should we be worried about that? He doesn’t think so. Plus: Why a lot of businesses still don’t offer 401(k) plans. And if job candidates want to bring a parent along to an interview, Gene says he’s fine with that.
This week, in episode 200, Shawn Busse, Liz Picarazzi, and Jaci Russo talk about how the marketing world is turning upside down. For decades, business owners have treated search engine optimization as something of a religion. They may not have been able to explain it, but they had faith that, if they obeyed the rules, Google would discover their sites and rank them. But search engines are getting a lot less generous about sharing links, and Shawn fears there’s an apocalypse coming for businesses that rely too heavily on SEO. Jaci’s a little more optimistic: “There'll be some other places to go get free traffic,” she says. “There always are.” Plus: Liz gives us an update on her recent trip to Vietnam in search of a contract manufacturer. And in a case study ripped right from the subreddit headlines, I ask the three owners: What do you do if a loyal, hard-working employee starts a side hustle selling a product that doesn’t compete with your product but looks a whole lot like it?
This week, Shawn Busse talks about why the business-advice books we’ve all read often fall flat. Shawn says it’s because much of what they suggest is predicated on a traditional model of a business that makes widgets. As a result, that advice may work fine if you are a manufacturer, but it’s far less likely to help if your product or service is more customized. That may seem obvious but the thinking Shawn describes remains deeply embedded in the small business mindset. One example: the implementation of highly regimented processes. It can be great for some businesses, stifling for others. (You can also read “Rethinking Your Value Model,” an article Shawn wrote on this topic.)
This week, in episode 199, Jennifer Kerhin tells Shawn Busse and Jay Goltz that she finally managed to take her first real vacation since starting her business almost 20 years ago. The vacation is part of a decision she made last year to regroup a bit, in part by backing off on her sales and marketing outreach. The goal is to give her team and herself a bit of a respite while they catch their breath and while Jennifer institutes processes that will improve operations. Of course, that raises an obvious question: Will she be able to turn the growth back on when the time comes? Plus: Shawn and Jay explain how they’ve eliminated negotiation from their hiring regimens. And all three debate who’s really responsible when owners pay for a marketing plan that doesn’t work: Is it the salesperson who pitched the plan? Or the owner who fell for the pitch?
This week, Tracy Bech, who is co-author of the “60 Minute CFO” and who has bought and sold businesses herself, offers some guidelines on how to approach an acquisition. Some of it is looking at the numbers, of course. Some of it is understanding the story behind those numbers. And some of it is psychological, controlling your emotions and maintaining a willingness to walk away from the deal if something doesn’t break right. And by the way, Tracy says, it’s never a bad idea to use the same lens to analyze the performance of your own business.
This week, in episode 198, we get updates from Laura Zander, Sarah Segal, and Jay Goltz. Laura wonders whether the time she’s put into integrating her latest acquisition might have been better spent focusing on her core businesses. Sarah, who has shifted to pursuing smaller clients, asks Laura and Jay to articulate the PR pitch that would interest them. But how do you evaluate the effectiveness of a PR campaign? Does it have to generate sales? Plus: Jay explains why he views confronting his current business challenges as a matter of triage. He also says that if he could write a check for $200,000 and solve his technology problems, he would do it in a heartbeat. Any takers out there?
This week, Gene responds to a New York Times article suggesting that CEOs should be among those worrying about whether artificial intelligence will take their jobs. For one thing, companies could save a lot of money replacing their leaders with bots. But Gene’s not buying it—although he does see Microsoft and Google making big progress with their AI offerings, so much so that he’s adjusting the services his own business offers. He says it’s time for owners to start paying more attention to AI.
We’re calling it a We-SOP. The term, coined by Jay Goltz, refers to a business transition that is something of a do-it-yourself ESOP, or employee stock ownership plan, but without the expense and complication and debt of a full ESOP. It’s a transition that lets owners get money out of what has been their life’s work. It’s a transition that lets loyal employees keep their jobs and preserve the company’s culture. And it’s a promising solution for the Silver Tsunami of retiring Baby Boomers because it can provide a sales path even for owners who have never managed to extricate themselves from their day-to-day operations. And in this week’s episode, we take you through an example of how it can work. Jay introduces us to Jill and Paul Choma, co-owners of a business, Gilded Moon Framing, that Jay recently guided through the We-SOP process. As you’ll hear, all three believe that what has worked—at least so far—for Jill and Paul could also work for many other business owners.
It’s easy! Anyone can do it! This week, in episode 196, Shawn Busse, Jaci Russo, and William Vanderbloemen talk about a whole slew of marketing challenges. From strategizing for trade shows, to whether your logo has to tell a story, to understanding what constitutes a brand, to whether that iPad ad Apple pulled was terrible or brilliant, they discuss what makes marketing so difficult. It all starts, Jaci says, with the industry’s refusal to set standards: “I can't find another industry that treats themselves so badly. Electrician, CPA, Realtor, hairdresser, nail salon tech, everybody else has some semblance of something to say, ‘I am a legit entity.’ Except our industry.” Which is part of the reason, Jaci says, that the constant refrain she hears from frustrated business owners who hire agencies is, “We paid them all this money. And we got nothing for it.” Plus: how do owners get past that feeling that they need to be the hardest worker in the office, the first one in and the last one out?
You are. That’s Gene Marks’ story, and he’s sticking to it. This week, Gene talks about all of the people who love to hate on Workday’s HR platform, and he argues that whatever problems exist are really the fault of the companies using the software, not the company that makes it. Plus: Gene tells us what we need to know about the latest ChatGPT upgrade. Spoiler alert: He says we will long remember the spring of 2024 as the moment when the true power of artificial intelligence became clear, but so far it’s mostly big businesses that are reaping the benefits.
This week, in episode 195, Mel Gravely tells Jay Goltz and Liz Picarazzi about his recently executed succession plan, including what’s worked and what could have gone better. The main thing that could have gone better, Mel says, is his purchase of another small business where he says he misdiagnosed the challenges the business is confronting: “I thought they just had a bad model and they weren't managing it well. It was worse.” All of which leads to a discussion of the role that a board of advisors can play in helping an owner build a business. While Mel has said he wouldn’t run a lemonade stand without a board, Liz and Jay—like most business owners—have taken a different approach. The notion of having a board of advisors, Jay tells us, is something he struggles to get his head around. “I’ve been doing this for 45 years,” he says, “and I’ve never had anybody to answer to.” Plus: with the talk of tariffs getting louder, Liz updates us on her search for an alternative to manufacturing her trash enclosures in China. “We really have to have a Plan B,” she says. “We'd be stupid not to have a Plan B.”
This week, Gene talks about an intriguing banking trend that’s come out of Europe and could be headed our way. It sounds a little dicey, but it could take some of the work out of applying for a loan. Plus: business owners say they expect artificial intelligence to increase--not decrease--their headcount. Could they be right? And can we all agree on the definition of a small business?
This week, in episode 194, Shawn Busse, Jay Goltz, and Jaci Russo talk about the new rules that may—or may not—ban non-compete clauses, increase the number of employees who must be paid overtime, and eliminate TikTok in the U.S. How much would those changes matter to each of their businesses? What might the owners do differently? Do the changes make sense? And why does it so often seem as if it’s small businesses that get caught in the cross-fire when the government tries to rein in abusive big businesses? On the question of non-competes, Shawn says he thinks they are often used by lazy businesses that haven’t done the real work of building loyalty with employees and customers. Plus: Do Shawn, Jay, and Jaci ever regret starting a business? Have there been times when they’ve thought about packing it in and trying something else? And also, are the terms “business owner” and “entrepreneur” interchangeable? Or do they carry different connotations? Might there be a better term? Jay thinks there is.
This week, Shawn Busse talks about his belief that, for all kinds of understandable reasons, business owners have been fixated on marketing tactics that amount to a losing battle of digital trench warfare. Over time, he says, those tactics have come to cost more and return less. But there are alternatives, and Shawn takes us through some examples. Plus: Are there lessons for smaller businesses in Walmart’s decision to place a big bet on a premium line of food.
The wrong way to make innovation happen, Ty Hagler says in this week’s special bonus episode, is to have a great idea and then go all-in trying to create it. That, he says, is a really expensive way to find out if your idea works. The right way to pursue innovation, he says, is to take your idea to customers so you can assess the pain points and opportunity spaces before proceeding. Hagler, who is founder and CEO of Trig, an innovation and design firm in North Carolina, also says he’s learned that the problem with focus groups is that the more people you have in the room, the less valuable the conversation tends to be. In fact, he says, one-on-one is best. He also says that brainstorming remotely can actually work better than in-person. Oh, and by the way, if your Mom tells you she loves your idea and will definitely buy your product as soon as it’s available, she’s probably lying.
Okay, maybe not every business, but this week, Gene Marks tells us about a little known program in the Department of Defense that is dedicated to helping small businesses find contracting opportunities at all levels of government and even with prime contractors. The service is free, it includes one-on-one counseling, and the advisors will help you through every step of the often-frustrating application process. You might be surprised by the opportunities out there. Plus: Is inflation still a problem for business owners?
This week, in episode 193, Sarah Segal takes Paul Downs and Jay Goltz through her recent QuickBooks nightmare. Right before tax season, Sarah ran her P&L, and it showed a profit of $250,000—but she knew right away that that couldn’t be right. It then took a bookkeeping SWAT team to figure out what exactly had gone wrong. “I was literally on the verge of tears,” Sarah tells us. “How am I going to do this and not be late on filing my taxes? And credit to this woman, who, I swear to God, was like my therapist and my bookkeeper. She was like, ‘Don't worry, Sarah. We're going to figure it out.’” Which they did—and which brings an important reminder: Not every dollar that comes in the door should be counted as revenue. Plus: What do you do when a new employee isn’t working out? When is the right time to intervene? Do performance improvement plans actually work? Are grace periods a good idea? Also: Jay emphasizes a little understood reason why it can be important to fire fast. And Paul explains what he likes about the AI search engine Perplexity.
This week, Victor Hwang, who is founder and CEO of Right to Start, talks about what he and his organization are doing to bring down the barriers that make it harder than it has to be to start and build a business. Among other things, we discuss the state-by-state progress Right to Start has been making, the drivers behind the recent surge in business starts, and the need for capital sources beyond banks and venture capitalists.
This week, in episode 192, special guest Jenelle Etzel, who majored in weaving, tells Shawn Busse, who majored in ceramics, why she believes attending art school and managing a punk rock band were perfect preparation for building a thriving real estate business. Her agency, Living Room Realty, has 130 brokers, roughly $5 million in revenue, and a market position that stands out among the big boys. While she once considered business a dirty word, she has embraced entrepreneurship and learned lots of important lessons, mostly through trial and error. For one, she figured out that there was a segment of the housing market—or the potential housing market—that more traditional brokers were ignoring. She also figured out, somewhat counterintuitively, that her real customers aren’t the people who buy and sell homes. Her real customers, she says, are her brokers, who happen to be independent contractors: “I can't tell anybody what to do,” Jenelle tells us. “So it's like being a politician, in a way. I've got a lot of responsibility with very little authority, and that's an interesting leadership challenge.”
This week, Shawn Busse talks about how much harder marketing keeps getting, especially for do-it-yourselfers. The cost of everything keeps going up, and the likely returns keep going down. As Shawn points out, it’s even getting expensive to advertise on podcasts. Wait! People pay to advertise on podcasts!!!!????
This week, in episode 191, Liz Picarazzi, Jaci Russo, and Laura Zander talk about what it’s been like building a business in partnership with a spouse, and they all agree on some important things. For one, they all say that, had their husband been just another employee, he probably would have been fired. All three say that in their relationships, they are the gas that drives the business, and their husband is the brake that sometimes keeps them out of trouble and sometimes frustrates their entrepreneurial instincts. And all three agree that some things are best left undiscussed. For example, says Jaci: “Michael doesn’t even know what we make. He also doesn't know what any of the employees make.” But the three CEOs also agree on this: In the final cost-benefit analysis, they wouldn’t want to build a business any other way.
This week, in episode 190, Jay Goltz tells Shawn Busse and Jaci Russo that, while he’s always been good with numbers, he’s never really enjoyed tracking his finances. It’s not what drove him to start a business, and over time, he stopped paying close attention. But now, after seeing his inventory levels and some big expenses get out of control, he’s diving back into the numbers and pretty much serving as his own chief financial officer, something he says he should have been doing all along. Plus: Shawn explains how one book and a specialized accounting firm and a monthly routine have gotten him comfortable with his numbers. And Jaci says it took years for her to learn to ignore the accountants who always gave her the same advice: Cut expenses. Instead, she tells us, “We've spent the past probably eight years really right-sizing what we charge. And now I feel like I can breathe.”
Gene addresses the big legal settlement in which Visa and MasterCard have agreed to cap the fees they charge merchants for five years. He explains both why many merchants are disappointed in the settlement and why he’s perfectly happy to pay those swipe fees when his big-ticket clients pay with a credit card. Plus: Gene discusses the new IRS tax rules you should know about and how the bankruptcy code has made Chapter 11 less of a defeat and more of a strategic tool for small businesses.
This week, in episode 189, Paul Downs, Jennifer Kerhin, and Liz Picarazzi discuss the challenges couples face when one spouse is building a business. Liz says it was important to let her husband know that she spent years working on a business plan before leaving her corporate job to start her first business. Paul explains why, when times have been tough, he hasn’t always shared the bad news with his wife. And Jennifer says too many couples planning for one spouse to start a business focus on best-case scenarios rather than the more likely worst-case scenarios. She also suggests some important questions for couples to ask themselves, including this one: “Will she still have faith in him if the business fails?” Plus: Businesses fail all the time, of course, and Paul explains why he thinks it’s usually for one of three reasons. And four years after the pandemic arrived, we take a look back: What was each owner’s toughest moment? What was their best decision? How have their business models changed?
Obviously, there’s no one-size-fits all answer to that question, but this week Shawn Busse offers up a slew of smart considerations and guidelines to help business owners come up with an answer that makes sense for them. A couple of Shawn’s points: If you haven’t done so already, spend the money getting to know your customers better. Plus: it’s important to understand why digital marketing works for some but not for others.
This week, in episode 188, we offer you a taste of the 21 Hats Live event we held in Fort Worth two weeks ago. It’s a different kind of event where there are no speakers, only participants. It’s pretty much a three-day, peer-group session for business owners, where we share challenges and insights and make connections. There were 25 of us, including most of our podcast regulars.
For me, the highlight was an exercise that Chris Hutchinson of the Trebuchet Group facilitates. He calls it a “Fish Bowl” because the idea is to have an owner stand up and expose everything about a specific challenge that he or she is confronting. Fortunately, we had one owner who was gracious enough to agree to reveal all, to answer any question. And that owner was, well, it was me, actually. The truth is, this was a priceless opportunity for me to get some feedback from a focus group of smart entrepreneurs who were already familiar with 21 Hats.
It even got a little emotional, mostly because a couple of the owners were kind enough to say that, had it not been for 21 Hats, their businesses might not have survived the pandemic. That was moving to hear, to say the least, but of course, that alone doesn’t mean 21 Hats has a sustainable business model. We recorded the whole thing, and if you have any thoughts after listening to it, please send them my way.
Sound engineer: Blake Sessions, Content Capital.
This week, Gene Marks tells us it’s time to update your clunky old technology. There was a time when he understood why owners said they were sticking with the old stuff because it wasn’t broken and they didn’t want to endure the pain of transitioning it. But those days are over, says Gene. If you have any hope of selling your business or passing it on to the next generation, it’s time to act. Plus: Why Gene thinks most owners need to get out of their offices more. And why he opposes a ban of TikTok.
This week, in episode 187, Matt Hoying, president of Choice One Engineering, explains to Shawn Busse and Jay Goltz how he created a DIY employee-ownership plan for his firm. Some 10 years ago, Matt’s predecessor as president tasked him with selecting an ownership structure that would engage employees and help Choice One be as successful as possible. That sent Matt on a mission of discovery in which he researched the pluses and minuses of every structure he could find—including employee stock ownership plans—before ultimately creating his own structure. Matt’s plan doesn’t enjoy the tax advantages of an ESOP, but it’s open even to part-timers, and it requires employees who want to be owners to make a financial investment in the business. In other words, they aren’t given ownership; they have to buy into it. Shawn and Jay quiz Matt on the choices he made and how the plan has worked out.
This week, the founder and CEO of Small Business Majority talks about whether he heard what he wanted to hear in Joe Biden’s State of the Union address, what he makes of recent court rulings asserting that the Minority Business Development Agency must support owners of all races, and what he makes of the growing demand from businesses for more immigration.
This week, in episode 186, Shawn Busse and Laura Zander discuss what exactly Laura’s job should be. She’s CEO, of course, and she’s been focused on acquisitions and growing the business, but she’s never really found someone to take over the big role she used to play, which leads to these questions: Should she go back to being her own chief marketing officer? Or does she need to go out and spend real money to hire one? And then, toward the end of the conversation, Laura actually devises a plan on the spot to sell yarn in a surprising and creative way, which perhaps answers the very question we’d been discussing. Plus: Shawn explains how having the right partner can make or break a business as he celebrates having made his final payout to his own former partner.
This week, Gene Marks offers to boldly go where no business owner has gone before. Few of us need to be convinced that artificial intelligence will be transformational, but even fewer of us have the time, energy, and capability to keep checking on which AI apps and platforms are worth using right now. Which is why Gene Marks has given himself precisely that assignment. This week, Gene reports back on what he found when he explored OpenAI’s GPT store for business owners. Did he find lots of useful stuff? Actually, what he saw reminded him of the iPhone app store (circa 2007). Plus: Gene also explains why divorce can be especially nightmarish for business owners and what they can do to prepare for and ease the pain.
This week, in episode 185, Jay Goltz, Jaci Russo, and Sarah Segal talk about whether it’s finally time for Jay to enter the brave new world of task-management software. That’s, in fact, what his two kids in the business are encouraging him to do. As it happens, Jaci and Sarah have tried most of the project-management tools out there—Monday, Basecamp, Asana—and they kind of love them, but with one caveat: They can be a lot of work. Which is all Jay needed to hear. After that, we talk about the challenges of managing credit cards and points, and Jay explains why, after 40 years, American Express is no longer what’s in his wallet. Plus: the owners tackle a question posed by an entrepreneur with a very new startup: “When does the anxiety of a new business subside?” asks the newbie, which prompts some laughter and this answer: The anxiety subsides in the 42nd year, says Jay, who’s been running his business for 42 years.
All businesses have ups and downs. This week, Tracy Bech, CEO of Starboard Collectives and co-author of the “60 Minute CFO,” offers some guidance on when to ride out a slow period and when to take action. Plus, she also talks about how she’s building an AI tool to help with financial analysis and when it makes sense to hire a fractional CFO.
This week, in episode 184, Mel Gravely, Liz Picarazzi, and Jaci Russo talk about how they set prices. Jaci explains why she refuses to respond to requests for proposals. “We have not participated in a single RFP in 15 years,” she says, “and we won’t under my watch.” Mel explains how his construction company manages to get work despite always being among the highest-priced bidders (which is why he never gets government jobs). And Liz tells us what happened when she was forced to raise prices because of the tariffs placed on goods manufactured in China. But first, she tells us what she’s thinking now that there’s a possibility those tariffs could go to 60 percent. Plus: We review how the three owners handle employee reviews.
This week, Gene tells Loren Feldman about a little experiment he ran recently in which he boosted a post on X, formerly known as Twitter, that was designed to send people interested in his book on customer relations software to a landing page on his website. X reported that the post was a big success. But was it? Gene offers a slightly profane rebuttal. Plus: He also talks about three Jeff Bezos quotes that he believes can change how you run your business, and he explains how companies can commit wage theft without even realizing it.
This week, in episode 183, Paul Downs, Jay Goltz, and Sarah Segal talk about sexual harassment and where you draw the line with employees. Is it sexual harassment for one employee to ask another for a date? Is it sexual harassment to ask twice? Does it make sense to have a policy of zero tolerance? Or is it better to leave room for discretion and judgment? The conversation was sparked by a recent situation Jay experienced with an employee who had been with the company for almost three decades, having started at the age of 17. “It was a very sad thing,” Jay tells us.
Plus: Sarah Segal asks whether it’s better to build her business on a bunch of small clients or a smaller number of large clients. And is being CEO a health risk? We begin the episode by talking about an eye-catching story the Wall Street Journal recently published noting that an increasing number of CEOs have been dying on the job, presumably because of the heightened levels of stress. I asked the three CEOs on the episode if they’ve been taking care of themselves—but they weren’t having it. Instead of thanking me for my concern, they chided me for highlighting an article they consider complete BS. Which, of course, is what we love about these guys. They call ‘em the way they see ‘em.
This week, Shawn Busse, who soon will be boarding an Alaska Airlines plane made by the Boeing Company to attend the 21 Hats Live event in Fort Worth, finds lessons for smaller businesses in Boeing’s struggles. For one thing, there’s always danger when combining the cultures of two different companies. Plus: Shawn, whose company, Kinesis, has been a certified B corp since 2016, talks about whether the certification is losing its luster.
This week, in episode 182, Shawn Busse, Jay Goltz, and Jennifer Kerhin respond to a somewhat depressing view of business ownership offered by an investor who buys businesses for a living. That view, essentially, is that for most owners, building a business is a daily knife fight of long hours, unexpected risks, slow growth, and meager returns. In this episode, I read most of the investor’s observations to Shawn, Jay, and Jennifer, and get their reactions, which hit upon a bunch of issues that are not widely understood—including how fast growth can destroy a business, how even a profitable company can go bust, and why a good metric to assess the health of a small business might be how many people have been crying in the bathroom this year. While Shawn, Jay, and Jennifer disagree vehemently with a few of the investor’s assertions—”Kiss my ass!” says Jay in response to one—they do acknowledge that he makes a lot of good points, which leads to an obvious question: Why would anyone do this? Why would anyone subject themselves to this kind of life? As you might expect, Shawn, Jennifer, and Jay have a response to that as well.
That, at least, is what Gene Marks is planning to do. Gene tells Loren Feldman that the new rules, which are scheduled to take effect in March, would have a profound impact on many businesses, including his—if they are actually enforced. But Gene’s not convinced that’s going to happen. Before you relax, though, Gene’s even more worked up about the new guidelines coming from the EEOC regarding harassment in the workplace. Very few businesses, he says, are prepared for what’s coming. One warning: when Gene talks about regulation, his language tends to get a little salty.
This week, in episode 181, Mel Gravely, Jaci Russo, and William Vanderbloemen talk about the possibility that, after several years of the Great Resignation and the labor shortage, some owners may have given away the store. We all know the risks of not offering employees enough. What are the risks of offering too much? How do you even know when you’ve crossed the line? The owners also discuss why this might be a good time to consider acquiring other businesses. “I think this is a time to double-down,” says Mel. And Jaci explains how she and her team are reviewing everything the company does to see if AI can be employed to improve each and every process. Oh, and one last thing: How exactly, in this day and age, are business owners supposed to keep track of all of the subscriptions—and all of the subscription log-ins—that they and their employees have acquired through the years? How much money are they spending on stuff they no longer use? “Thanks a lot,” responds Mel. “I’m starting to sweat.”
This week, Gene Marks tells Loren Feldman that while he’s excited about all of the great stuff we will eventually be able to do with artificial intelligence, business owners should stay away from Copilot for now. As with a lot of Microsoft products, Gene says, you just don’t want to be an early adopter. Plus, Gene explains his not-completely-obvious fraud-prevention strategy: Make your people take vacations.
This week, in episode 180, Jay Goltz, Jennifer Kerhin, and Liz Picarazzi discuss their efforts to get a better grasp of what drives their profits. They ask how much of their finances they should manage themselves. And how much should they rely on an accountant or a fractional CFO? When does delegation become abdication? Jennifer says she’s benefitted from hiring a fractional CFO who has taken an active leadership role, including setting up a database that helps Jennifer see in real time whether the fees she’s charging cover the labor she’s deploying. “Whatever she's charging me,” says Jennifer of her CFO, “it's absolutely worth it.” Liz, meanwhile, thinks she should be doing more herself. And Jay says he was paying big bucks for a full-time CFO until late last year. “And it was a complete waste of money,” he says, which is why he’s decided not to replace her. Plus: Liz reveals her secret strategy for marketing directly to municipal government officials, some of whom have started to use the term “Citibin” generically. And the owners respond to a question from the head of a cost-reduction service who wonders why she’s struggling so much to get business owners to try her risk-free service.
Well, yes, actually, but Gene Marks and Loren Feldman discuss two questions: One, what exactly is driving the boom? And, two, are the startups substantial enough to matter? Or is this just about people losing their jobs and driving for Uber. Plus: what would you do if you owned fast food locations in California where the minimum wage for fast food workers will jump to $20 an hour in April. And what are business owners to make of the case the Supreme Court heard last week about the constitutionality of federal regulation?
In this week’s bonus episode, Cameron Madill takes us on his succession journey, which began years ago when he started having conversations with older business owners, many of whom seemed to feel trapped. They’d had a lot of success, they were proud of the business they’d built, but they weren’t sure what to do with it or how to leave it. None of the usual options seemed terribly appealing. Hoping to write a different ending, Madill, now in his 40s, started looking for better options much earlier than most owners, and the one he landed on was an unusual choice: a worker cooperative. Now, there are aspects of this model that are likely to give some owners pause. For one, a co-op probably isn’t going to produce the biggest payday for a selling owner. And if the owner wants to stick around as CEO, he or she will have to report to a board, and that board can challenge any and all of the owner’s decisions. But Madill, as he explains in a conversation we recorded late last year, before he stepped down from his role as CEO, decided to sell to his employees anyway. Not only is he glad he did, he thinks co-ops are an option far more owners, especially those struggling to find a buyer, should consider.
This week, Shawn Busse and Loren Feldman talk about some big changes coming to the world of small business. At his consulting firm, Kinesis, Shawn is already beginning to experience the impact artificial intelligence is having on his industry. He knows B2B business owners who are spending a lot of time on TikTok—and they’re not just watching dancing videos. And his client base has already shifted dramatically toward women-owned businesses.
This week, in episode 179, Shawn Busse, Paul Downs, and Laura Zander talk about why 2023 was so challenging for them and what they plan to do differently in 2024. “Last year was a year when I knew I was going to be making a bunch of investments and didn't expect to show much or any of a profit,” says Paul. “And I absolutely nailed that goal.” Shawn, meanwhile, thinks his new marketing scheme is working, and Laura is addressing her issues by going shopping — shopping, that is, for businesses. She’s now bought a total of six, and she offers a step-by-step guide to how even a relatively small business can grow through acquisition, including what she’s looking for (mostly companies in distress), how she sets a price (she aims to recoup her cash outlay pretty quickly), how she finances the deals (not with a bank!), and how she integrates her old and new operations (that can be a bear).
This week, John Arensmeyer, founder and CEO of the advocacy group Small Business Majority, tells us that he senses considerable optimism among the many business owners in his network notwithstanding some concern for looming policy and economic issues. Among those issues, John tells Loren Feldman are: access to capital, the cost of health care and health insurance, relations between franchisors and franchisees, price discrimination against smaller businesses, the burden of the new Corporate Transparency Act, and the upcoming battle over the sunsetting of the Trump tax cuts.
Show Notes:
You can find more information about the Corporate Transparency Act requirement here.
This week, we take a look back at the conversations we had last year about the many rewards and responsibilities of business ownership, highlighting some of our happiest, smartest, funniest, and most difficult exchanges from the past year. Along the way, we discuss topics such as escalating salary demands, how much profit a business should make, a new way to sell a business, the problems with ESOPs, how to sell cookies on LinkedIn, breaking a million dollars in annual revenue, escaping the valley of death, and the pain of having to fire a long-time employee.
There aren’t many places where you can hear entrepreneurs talk about the real-life problems they are confronting right now, today, as they happen—with no guarantee of a happy ending. But those are the conversations I have every week with Paul Downs of Paul Downs Cabinetmakers, Shawn Busse of Kinesis, Jay Goltz of Artists Frame Service, Mel Gravely of Triversity Construction, Jennifer Kerhin of SB Expos & Events, Liz Picarazzi of Citibin, Jaci Russo of BrandRusso, Sarah Segal of Segal Communications, William Vanderbloemen of Vanderbloemen Search Group, Dana White of a soon-to-be-named successor to Paralee Boyd, and Laura Zander of Jimmy Beans Wool.
In this episode, we also highlight several appearances by special guests who stopped by in 2023 to discuss their journeys, including Muhammad Abdul-Hadi of Down North Pizza, Jeff Braverman of Nuts.com, Michael Brown of Teamshares, Brad Herrmann of Text-Em-All, Grayson Hogard of Grove Cookie Company, Lance Tyson of the Tyson Group, and Ari Weinzweig of Zingerman’s. If listening to one of these highlights makes you want to go back and listen to the full episode, that can be done most easily by going to 21hats.com. There you’ll find a transcript of this episode with links to all of the episodes we sample.
So here was Muhammad Abdul-Hadi’s idea for a pizza joint: First, buy a building in one of the most troubled neighborhoods in one of the poorest big cities in the country. Open a restaurant despite having no experience in the food industry and do it during the pandemic when many restaurants are failing. And hire only people who, like Abdul-Hadi, are convicted felons. If that business plan sounds a little dicey to you, rest assured you would not be the first to suggest that to Abdul-Hadi. But he did it anyway. He built out the restaurant, and it opened in 2020 to lines that required people to wait as long as three hours for their pizza—thanks in part to a marketing plan that created excitement and scarcity by “dropping” pizzas the way some people “drop” special-edition sneakers. And now, Down North Pizza, which has been featured on best-of lists in national publications like Bon Appetit and The New York Times, is looking to expand. A special, year-end bonus episode.
In our last conversation of the year, Gene Marks tells Loren Feldman about the nine habits that he believes have helped him build a business. Those habits include meeting regularly with his accountant, meeting regularly with his clients, and over-paying his employees. Gene saves what he considers the most important suggestion for last: Make time to enjoy your family.
This week, in episode 177, Shawn Busse, Liz Picarazzi, and Jaci Russo discuss what they learned in 2023 and what they expect from 2024. After a tough year, Shawn is optimistic that his clients, having survived the turbulence of the past few years, are ready to spend money and try something different. Liz explains why she’s been willing to discount her products as much as 40 percent on Cyber Mondays and tells us about some new products she has in the works. Early in the year, Jaci, thinking she was going to have to staff up to handle two big new clients, dove into remodeling her offices—but those big clients have yet to sign on. “I might have jumped the gun a little bit,” says Jaci. Plus: Liz talks about her Midwestern mom, who can’t understand how Liz can charge so much for her trash enclosures. And Shawn raises the issue of how much money business owners should spend on marketing.
This week, Gene Marks shares his suggestions for anyone looking to save a little on taxes. Start with your retirement account. Better yet, start planning ahead for next year. Plus: What’s the best CRM for solopreneurs and microbusinesses? What artificial intelligence apps for business are worth trying right now? And what does Philly native Gene make of the $140 Philly cheesesteak?
This week, in episode 176, Paul Downs tells Jay Goltz and Jaci Russo about the latest developments in his year-long campaign to stop relying so heavily on Google AdWords. At a specially arranged, two-day marketing event, Paul got to sit down with a series of architects and designers who had already been vetted and who he hopes will become repeat customers. So far, Paul says, the results look promising. Plus, we also discuss: Do you write your website copy to please Google or to please people? Is there any way around skyrocketing property insurance rates? Why has Jay decided he no longer needs a chief financial officer? How big a disadvantage to owners are the new laws forbidding employers from asking job candidates about their salary histories? And would you reject a candidate simply for trying to negotiate a starting salary? I know someone who would.
This week, Gene Marks talks through the latest developments in customer relationship management software, which is both his area of expertise and a real pain point for many business owners. Among other things, Gene tells us about the impact artificial intelligence is already having on CRM, including what A.I. makes better as well as what it makes worse. Plus: How do you get salespeople to use your system properly? And what should you do if you’re completely frustrated and ready to dump your system?
It used to be that best practices in sales were pretty standard across the board. But since the pandemic and with the advent of artificial intelligence, says Lance Tyson, founder of the Tyson Group sales consultancy, it’s like the Wild West out there. Suddenly, everyone’s playing by different rules, and the best sales approach can vary, depending on the seller, the target, the industry, the region of the country. The keys, Tyson says in this week’s bonus episode, are to pay attention and stay flexible. Along the way, he also addresses a host of hot topics: How important is it to see a prospect face-to-face? Is cold-calling dead? Will A.I. replace sales trainers? What’s the right balance between base and commission? How do you handle the salesperson who can’t or won’t be a team player? How do you get salespeople to take maintaining their CRM seriously?
This week, in episode 175, Jaci Russo explains how she put an end to her eight-month drought of new clients. Jennifer Kerhin takes us through the bureaucratic nightmare of managing remote workers based out of state (“That is a headache that I don't wish on my worst enemy,” says Jaci, who has found a way to sidestep the problem). And Liz Picarazzi brings us up to date on her ongoing struggle to get her trash enclosures certified as bear-resistant. The common thread to these challenges may lie in these two questions: When is continuing to fight the good fight the definition of entrepreneurship? And when is it the definition of insanity? Plus: Why does it cost so much to exhibit at a trade show? And did you know that as recently as 35 years ago, there were still laws on the books requiring women to have a male relative cosign on a business loan? Those laws are now gone, thankfully, but Jaci, Jennifer, and Liz can all attest that that kind of paternalism is very much alive and well.
This week, Black Friday and Small Business Saturday will represent hugely important shopping days for many retailers. But Gene Marks tells Loren Feldman that the sales those days generate aren’t necessarily as important as the data they generate -- so long as the retailers are smart enough to capture it. Gene also talks about why business owners need to understand that when they sign their tax returns, they—and not their accountants—are responsible for what the returns show. Plus: why Gene loves shrinkflation as a pricing strategy and why it’s not just for those who sell food or products. It can even work for consultants like Gene.
This week, in episode 174, Dana White drops a few surprises. When we began this podcast in 2020, Dana had two promising hair salons in Detroit that she’d named after her grandmother, Paralee Boyd. She had an innovative business model designed specifically for women with thick and curly hair. And she was on her way to winning a prestigious business plan competition. All of which presented her with a wide array of opportunities to consider. Would she continue to bootstrap? Would she franchise? Would she take on an investor? Would she open salons on military bases? But the pandemic hit her hard. Struggling to find both employees and customers, she eventually decided to close her Detroit locations and open a new one in Dallas, Texas, where she hoped the greater population density would help her make a fresh start. But in this episode, Dana tells Jay Goltz and Laura Zander that she’s come to a painful realization: “Paralee Boyd is not working.”
This week, in episode 173, Shawn Busse tells Jay Goltz and Mel Gravely why he doesn’t want his firm, Kinesis, to be known as a marketing agency. Part of it is his sense that people just don’t trust marketers. But Shawn also believes that what Kinesis offers its clients is much more than just marketing. Hearing that prompts Mel to take us through his recent decision to spend a lot of money rebranding his construction business, which he says created alignment throughout the business and would have been worth twice what he paid. Plus: Mel explains how he manages to generate new business without employing salespeople. Jay asks if it’s still possible in this tight labor market to enforce attendance policies. And, for the first time in the almost four-year history of this podcast, Jay goes extremely quiet in this episode. What exactly was that about?
This week, Gene Marks warns business owners that the National Labor Relations Board has taken an action that could make it harder to fire employees who won’t come back to the office. But is that really the case? Gene’s also concerned about a new rule proposed by the Equal Employment Opportunity Commission that makes it even more important that business owners review their policies and training regarding harassment of employees. And then Gene reviews the case of an employee who filed some relatively minor misrepresentations in an expense report and then lied about it. Should the employee be fired?
If you’ve been listening to this podcast, you know we spend a lot of time talking about all of the things that can go wrong for a business owner. And yes, in part because we started recording these conversations just a couple of months before the pandemic hit, we’ve had plenty to talk about. Even this year, with the worst of the pandemic behind us, we’ve been talking about everything from excess inventory to lost clients to layoffs to ineffective marketing to surviving the valley of death. So, with that in mind, this week, I’ve chosen to replay an old episode both because it offers an inspirational message and because, well, we here at the home office need a little break. It’s the episode we recorded two years ago when Karen Clark Cole sold her business. Especially given that Karen had only recently been through a tough period that prompted her to take time away from the business, the conversation is a nice reminder that sometimes things do come together. It’s also full of great advice for anyone who thinks they may want to sell their business one day.
This week, Shawn Busse tells Loren Feldman why he’s long been skeptical of big data, especially the data many businesses collect from their customers. What’s the alternative? Shawn suggests doing something radical and having actual conversations with your customers, especially your best customers. Shawn also talks about why it seems so many businesses are struggling even as the economy is surging, at least according to the latest GDP figures. Plus: What exactly is wrong with the titans of Silicon Valley?
This week, in episode 172, Liz Picarazzi tells Jay Goltz and Sarah Segal that her trip to a bear sanctuary in Montana to get her trash enclosures certified as bear-resistant did not go precisely as planned. Because of a logistical snafu, she has not yet obtained either the certification or her real goal: a marketing video of the grizzlies attempting to crack open her baited enclosure. Fortunately, things went better for Liz in a more traditional marketing venue, a trade show in Chicago where she promoted her rat-resistant enclosures. Meanwhile, Sarah follows up on how things are going since losing two big clients and having to lay off three employees, and Jay explains his new catch phrase, “Let me not sleep on it.” Plus: we discuss the owner of a two-year-old construction business who wonders how long he should keep going if he doesn’t start to make a profit. He also asks why no one ever talks about how hard it is to run a business. While we can’t know for sure what’s happening inside his company, we can be pretty confident that he’s not listening to the right podcast.
For months, Gene has been telling us about all of the cool things we’ll be able to do with Microsoft’s Office 365 and Google’s Workspace when those companies integrate artificial intelligence into their platforms. Gene’s still excited about the possibilities, but he’s also more than a little annoyed, because both Microsoft and Google are planning to charge us quite a bit more for their A.I. enhancements. Gene also talks about automated invoicing, which he believes is going to displace a lot of employees, and why he believes most business owners are doing a poor job managing their insurance needs.
This week, in episode 171, we meet Jaci Russo, the co-founder and CEO of BrandRusso and the latest addition to the 21 Hats Podcast team. Jaci tells Jay Goltz and Laura Zander how she went from working for Barry Diller to starting her marketing agency. Jaci also explains why she recently decided to introduce a four-day workweek and why she thinks her agency has now gone eight months and counting without signing up a new client—the longest such stretch in more than 20 years in business. “I find it interesting,” responds Jay. “You just said this is the first time you've ever had such a long period without new business. And, ‘Oh, we went to a four-day workweek.’ Hmm, how interesting.” Plus: Laura talks about what happened when venture-backed competitors came for the knitting industry and how stressful it is to buy and operate another business in another state.
This week, we learn that Gene Marks and Bernie Sanders agree on something, which is that there are better ways to handle health insurance than making business owners responsible for providing it to their employees. Isn’t running a business hard enough without this financial and bureaucratic burden? Does it really have to be this way? Plus: Why Gene thinks what he calls “the era of the worker” won’t last forever. And what business owners need to know and do before they lay off or fire employees.
It took a series of sad losses to turn banker Channon Kennedy into an entrepreneur. If a friend hadn’t lost his son and if Channon’s mother and sister hadn’t been diagnosed with cancer, she never would have designed, prototyped, manufactured, and started selling the Morgan Square, a tool that can save carpenters time while framing a project. CDhannon is just getting started, but we’ll keep in touch as her journey continues.
In this week’s bonus episode, Bill Fotsch, a business consultant, explains why he thinks much of the effort that he and many others have put into creating employee engagement over the past three decades has been wasted effort—well intentioned, but wasted. The fact is, Fotsch says, employees today are no more engaged than they were some 30 years ago when the concept of employee engagement first gained currency. So what’s the answer? Fotsch has come to the conclusion that it’s something he calls “economic engagement,” which happens to be the name of his consulting business. What exactly is economic engagement? He says it’s getting employees to focus on serving customers, and doing so profitably. He says it’s not so much about sharing financials with employees but about getting employees to understand the strategies and actions that really drive a business’s profitability. Fotsch is so convinced that he’s cracked the code that he’s gone beyond mere consulting and has been buying stakes in businesses so he can implement his ideas and prove his concept. So far, he says, it’s working.
Show Notes:
* See how you score on an economic-engagement benchmark survey.
* Here’s Gallup’s G12 employee-engagement survey.
* Bill Fotsch co-authored an article that argues economic engagement is a logical successor to open book management.
This week, in episode 170, Jay Goltz tells Shawn Busse about the latest stop on his journey to figuring out whether an employee stock ownership plan is right for his business. Jay’s latest adventure includes waking up at 4:30 in the morning in Minneapolis too anxious to sleep—“Oh my God, what am I getting myself into here?”—and deciding to leave the seminar and drive back to Chicago. But on that six-hour return trip, Jay says his anxiety turned into clarity. In fact, he thinks he’s pretty sure he knows now what he wants to do. Of course, he has said that before. And we continue to learn more about ESOPs, this week hitting upon an interesting issue: ESOP enthusiasts love to tout the benefits of turning employees into owners. But are they really owners? And is that the right message to send them? “If you bought 10 shares of General Motors stock,” Jay asks, “would you tell your neighbors that you're an owner of General Motors?” Plus: We also talk about when business owners should ignore their accountants and whether Shawn and Jay expect their employees to come forward and tell them if they see another employee doing something they shouldn’t be doing.
When Gene Marks and I recorded this episode of Dashboard on Friday, we were pretty sure the government was going to shut down. That, of course, didn’t happen so you can fast-forward through our brief remarks early in the show—or perhaps you would enjoy hearing Gene state confidently that he’s known all along that a shutdown was inevitable. We also discuss what Gene’s been hearing from business owners as he criss-crosses the country talking to various groups. And Gene talks about the IRS’s decision to suspend the ERC program and what you should do if you fear you may have been overly aggressive in your application. Plus, he explains why he hates LinkedIn but keeps using it anyway. -- Loren Feldman
This week, in episode 169, Sarah Segal tells Shawn Busse that the other shoe has dropped. A couple of months ago, as she’s shared here previously, Sarah lost two big clients in one week. Now she takes us through her decision to lay off three of her employees, including what it means for the business and what it means for Sarah’s own role in the business. Before the layoffs, she had gotten to the point where she was working on the business—but now that’s changed. “I'm not working on the business,” she says. “I am working for clients. I am getting the job done. I am making sure that we're successful with our clients, and that is my priority right now.” Plus: We also discuss how to choose a CRM, why Sarah and Shawn’s home cities of San Francisco and Portland have been getting such bad PR, and whether former business owners are employable. “I wouldn’t hire me,” says Sarah.
This week, Tracy Bech talks about why it’s important, from time to time, to review your margins, to compare them with those of others in your industry, and to look for ways they might be improved. You might even find ways to adjust your business model. The first step, of course, is to make sure you know what those margins are. Plus: when is it time to start thinking about next year?
This week, in episode 168, Shawn Busse, Paul Downs, and Liz Picarazzi talk about when it makes sense to walk away from a client. Liz, for example, is tired of dealing with bureaucracy and being at the bottom of the food chain. In one instance, she was so turned off that she actually recommended a competitor for a job she no longer wanted. Paul has a simple test: If it’s easy work for a bad client, okay, fine. But if it’s hard work for a bad client, “Just don’t do it.” Of course, there are times in the life cycle of most businesses when that’s easier said than done, when you have to accept almost any work offered. Those are the tough ones. Plus: Is it time for business owners to take artificial intelligence seriously? And should owners care that a well-known economics firm is predicting a depression in 2030?
John Arensmeyer explains what the end of pandemic-era childcare support will mean for businesses. He also talks about the Department of Labor’s proposed overtime rule and what’s at stake for business owners if the government shuts down. Plus: owners say banks are getting harder to deal with.
This week, in episode 167, Shawn Busse, Jennifer Kerhin, and William Vanderbloemen discuss private equity. Both William and Jennifer have been getting emails and calls from representatives of PE firms who come promising all kinds of gifts—connections, expertise, money to invest in the business, and money to take off the table—which is why the temptation can be great. “If anybody even just offered me a three-day vacation, I think I would jump at it,” Jennifer jokes. But of course PE firms do exact a price, possibly including control of what used to be your business, which is why Jennifer says she wonders whether she should even take the phone calls. Entering the conversation, she says, feels a little like entering the Garden of Eden. Do you take a bite of that apple? Plus, Shawn thinks he’s found a better way to manage his company’s credit cards, and Jennifer gives us an update on her new website.
This week, Dr. Randy Spencer talks about the changes that have been roiling the vet business. For one thing, that pandemic puppy boom we all heard about has brought additional stress to veterinary workers who had already had more than their share. For another, there’s been a wave of corporate money and private equity flowing into the industry. That sounds as if it could be a good thing. And in fact, Spencer says he’s been dodging a constant flow of acquisition inquiries for years. But the big money has also engendered considerable turnover and disruption, and in response, Spencer decided to sell 100 percent of his business, 1st Pet Veterinary Centers, to an employee stock ownership plan in 2021. The transition to an ESOP remains something of a work in progress, in part because veterinary people tend to be more focused on pets than they are on profits. “Veterinary medicine,” Spencer says, “is just the best profession in the world. In a way, it's a service industry, but we get to serve pets. That's why veterinarians get into it.”
This week, in episode 166, Mel Gravely—the newest addition to our podcast team—tells Shawn Busse and William Vanderbloemen how he bought a Cincinnati construction business in 2005 even though the company wasn’t doing well, even though he knew nothing about construction, and even though the company had been shopped to everyone who did know construction. As you’ve probably guessed, things worked out just fine for Mel, who is now focused on putting a plan in place that’s designed to keep Triversity Construction in business for 100 years. That goal, Mel explains, can mean taking some counterintuitive steps, including not always maximizing profit and not planning to stay in the CEO job as long as he might have preferred. Plus: we learn why the construction industry is unlikely to be an early adopter when it comes to AI. And William tells us how he did this year on his mission to make himself less essential to his own business.
SHOW NOTES:
Here’s the podcast where William first introduced us to his concept of a “vomit list.” Here’s a profile Bo Burlingham wrote about Dave Whorton, the founder of the Tugboat Institute.Here are the principles behind Tugboat and the evergreen philosophy of business building.
This week, in episode 165, Paul Downs, Jay Goltz, and Laura Zander don’t hold back. Laura and Jay both say their sales are coming in well below expectations. Not surprisingly, Jay has a five-point checklist that he’s using to assess and address his shortfall. Laura’s situation involves a marketing team that she says has been feeling stressed and is coming apart, with lots of crying and arguing. “They’re just collapsing,” she tells us. Paul, meanwhile, says his sales aren’t bad, but he’s got one employee who’s been holding them back. The employee, who’s been with Paul for 10 years, has been spiraling of late, says Paul, who’s dreading what he calls “the toughest conversation,” a conversation he fears will leave the employee devastated. In such situations, Jay says, he’s found it helpful to rank himself from one to 10 on the hardass scale: If Mr. Rogers is a 1 and Jack Welch—the take-no-prisoners former CEO of GE—is a 10, where do you want to be? “If you pick four or five,” Jay says, “you're probably gonna go out of business.”
Gene Marks tells Loren Feldman that by almost any measure the economy continues to perform quite well. And yet, business owners don’t seem to believe it. Why is that? Gene says owners have some cause for concern. In fact, he expects a slight recession or slowdown in the next three to six months—of course he’s been saying that for more than a year now. “One of these days,” he says, “I’m going to be right.” Plus: Gene highlights two significant tax credits that most business owners don’t know about.
This week, in episode 164, Shawn Busse and Jay Goltz discuss a recent Business Journal report that a lot of business owners are feeling burned out. Why is that, and what can owners do to avoid it? And have either Shawn or Jay been there? Plus: Shawn brings us up to date on the leadership transition he’s initiated, and—believe it or not—Jay has had another revelation about ESOPs. Also, do business owners need better regulation or no regulation? And which regulations are annoying Shawn and Jay the most right now? For Shawn, it’s the nightmare of having employees in multiple states and having to figure out and comply with the various rules of each of those states.
Show Notes:You can learn more about Shawn Busse’s September event Catalyst.
Here’s the Business Journal article about business owner burnout.
Here’s the podcast where Phil Hayes offers a fresh perspective on what it takes to do an ESOP.
Here’s the conversation where Jim Kalb talked about his own ESOP.
Here’s the most recent Dashboard conversation where I talk about regulation with Gene Marks.
This week, Gene Marks and Loren Feldman agree that artificial intelligence is becoming the biggest story in small business, with Gene highlighting a slew of AI tools that business owners can put to use right now. Gene also issues a warning that owners who do not start paying attention are taking a much bigger risk than they may realize. Plus: Gene also talks about team-building platforms that can help owners engage their employees, especially those working some or all of the time from home.
This week, in episode 163, Liz Picarazzi, Jennifer Kerhin, and Sarah Segal talk about whether they ever wish they could go back to their corporate lives. For Liz, there was a period during the early days of COVID. For Jennifer, it was when she made the transition from a consulting business to an employee business. These days, none of them can imagine going back—although Sarah did have a rough week recently when she lost two clients. “It's just the way of the world,” she tells us. “When businesses are looking to cut costs, it’s outside agencies that go first. But when it's two of your largest clients in the span of a week, it's like, ‘Really? Can I go dig a hole, put myself in it, and just stay there forever?’” What she’s actually doing, as we discuss, is figuring out some new ways to attract more clients. We also discuss whether everyone needs a business plan and whether the three owners ever wonder if someone else would do a better job running their businesses.
Yes, it’s August, but Tracy Bech — co-author of “60 Minute CFO” — tells Loren Feldman it’s not too late to assess where your business stands and take steps to hit your numbers. Tracy also talks about what prompted her to take her own financials seriously, what owners can do if their revenue isn’t meeting expectations, and why she kind of likes recessions but isn’t disappointed we haven’t had one.
This week, in episode 162, Jay Goltz tells us that, on second thought, he did learn something important watching HBO’s Succession. He still wants to work as long as he can—even if that means dying at his desk—but he now realizes, thanks in part to Logan Roy, that he needs to put a plan in place in case he were to get hit by that proverbial bus. This realization was also furthered by hearing the story of a 51-year-old entrepreneur who died in his sleep recently, leaving his wife to figure out how to keep their bank from calling its loans. As part of his hit-by-a-bus plan, Jay says he’s crossing streets very carefully, but also considering creating a board of advisors that will be able to offer advice to his survivors. But that’s a little tricky because, as you may have noticed, Jay’s not exactly a board-of-advisors kind of guy.
This week, Gene Marks tells Loren Feldman that the Silicon Valley notion that startups are threatened with extinction is ridiculous. In fact, new business openings have been surging. The real problem in Silicon Valley is the venture-backed business model. Plus: Gene also talks about a way for small businesses to help their employees get health insurance without having to actually offer health insurance. And Gene also tells us about a lesson in regulation he learned from an eight-year-old entrepreneur.
This week, in episode 161, Shawn Busse tells Jay Goltz and Jennifer Kerhin that he’s realized that his business, too—like Jennifer’s—is stuck in the valley of death that we first discussed a couple of episodes ago. Shawn’s realization prompts a discussion of what it takes to cross the desert and get out of the valley. We also have a surprisingly entertaining and enlightening conversation about insurance that makes clear why you should occasionally review what policies you have and why you have them. “I have something called directors insurance,” says Jennifer, “and I don't really even know what that is.” Shawn notes that he found a company that helped him reassess several of his insurance lines. “What I like about that,” he told us, “is that while insurance brokers are incentivized to oversell you, because they make commissions,” this company sells its expertise and not policies. Plus: we start the episode with Jay explaining why binge-watching HBO’s Succession brought back all of his worst nightmares about owning a family business.
This week, Gene Marks tells Loren Feldman that it’s hard enough trying to run a small business in 2023, but just try running one in a blue state, where he says businesses have been subjected to a tsunami of regulation mandating things like paid time off and safe working conditions. Gene also talks about what’s going to happen to all of that unused commercial office space and whether there’s any reason for businesses to try out the new Twitter clone, Threads.
If you’ve been listening to this podcast, you know that we’ve been taking periodic dives into the world of employee stock ownership plans. We started down this path because Jay Goltz was thinking about his own succession issues. In a series of podcast episodes and conversations and seminars over the course of more than a year, Jay progressed through the three stages of ESOP discovery: First, he had his eyes opened. (“Wait a second. If you’re an ESOP, you don’t pay taxes?”) Then he got a little euphoric. (“I think I can make more money owning 70 percent of the business than I do now owning 100 percent.”) And then he confronted what I’ve been calling the ESOP industrial complex—the big firm lawyers and consultants who sometimes seem inclined to make ESOPs as complicated and expensive as possible. (“They want to charge me a ‘success fee’ for finding a buyer even though they didn’t find the buyer.”)
That introduction to Big ESOP occurred at a conference that Jay and Shawn Busse attended in Portland and that left Jay convinced that ESOPs are probably right for a lot of people but not for him. And yet, it was also at the conference in Portland that Shawn and Jay met Phillip Hayes, who takes a decidedly different approach than the industrial complex gang. What immediately stood out about Phil, who calls himself The ESOP Guy and who has his own podcast, Journey to an ESOP, is that he doesn’t view his mission as selling owners on ESOPs. His goal is to help owners figure out which solution is best for them, whether that’s an ESOP or something else. Which is why Shawn and I decided to sit down with Phil and have a conversation—brought to you by our sponsor, the Great Game of Business—about his approach.
This week, in episode 160, Shawn Busse, Paul Downs, and Jennifer Kerhin talk about the challenges of communicating with employees, especially in the post-pandemic world. It’s hard enough to get aligned on mission and vision, but how do you connect with an employee you’ve never actually met in person? Is that even possible? We also discuss Jennifer’s realization that she has over-performed on sales but under-performed on marketing, which is part of the reason she’s re-doing her website. “I need a higher level of prestige,” she tells us, “so, better copy, better photographs, an all-around more sophisticated look. What we had was mom and pop. You know, Wix.” Plus: the panel tackles a question posted on the small business subreddit: “How large can my margins become before I'm ripping off my clients?”
This week, Gene Marks gives Loren Feldman a preview of what Microsoft is cooking up with a product called Copilot that Gene expects to be released before the end of year and that he promises will “rock your world.” Like ChatGPT, Copilot will access data on the internet but it will also be incorporated into all of Microsoft’s existing products so that it will also be able to access data in, say, your customer relations management software. That means you’ll be able to do things like ask Copilot to identify which of your customers you’re actually losing money on. For those of you already experimenting with ChatGPT, here’s a pro tip from Gene. To use ChatGPT well, you need to master the art of asking it prompts. Gene suggests consulting a helpful library of prompts for small businesses compiled by GoDaddy.
This week, in episode 159, Shawn Busse, Jay Goltz, and Jennifer Kerhin talk about that difficult transition most growing businesses endure when the owner can no longer handle all of the most important tasks herself but also can’t quite afford to hire the people she needs to lighten her load. It’s part of the reason Jennifer, as she’s told us in previous episodes, has been working 12-hour days, six days a week. It’s a challenging transition, and it has a name: It’s the “valley of death,” says Shawn, who compares it to crossing a desert. We also discuss how big the owners want their businesses to get, why important tools and processes seem to break with every $500,000 of revenue growth, and what constitutes the proper care and feeding of salespeople. Plus: Jay has an idea for owners who are having a hard time selling their businesses. The idea involves selling the business to a key employee in a transaction Jay is calling a WE-SOP. Get it? It’s kind of like an ESOP, but it’s a lease-to-own version of an ESOP. A WE-SOP.
This week, Gene Marks tells Loren Feldman about what he calls the “TWATS,” which is shorthand for hybrid workers who choose to work in the office only on Tuesdays, Wednesdays, and Thursdays. Gene doesn’t think it’s a coincidence that they’ve chosen to work from home on Mondays and Fridays. Plus: Gene also points to what he considers the Achilles heel of artificial intelligence and says that business owners should think twice about listening to the Supreme Court when it comes to discriminating against groups of people.
This week, in episode 158, Paul Downs, Jay Goltz, and Sarah Segal talk about where the dust has settled after years of turmoil in the labor market. As you know all too well, we’ve been through COVID, supply-chain issues, inflation, labor shortages, the Great Resignation, minimum-wage hikes, new pay-transparency regulations, and countless rumors of recessions that have yet to come—all of which has had an impact on wages. And that’s why I decided to ask Paul, Jay, and Sarah where their thinking has landed. The consensus here is that leverage is shifting back to employers, but Paul, for one, remains committed to paying his people more than they can find elsewhere. “It's worth it to me to have the team I want,” he says. “And sure, it affects profitability, but turnover affects profitability, too. And I'd rather not have that.” Plus: We also talk about whether Lululemon was right to fire two retail employees who tried to stop a robbery, and we answer the following listener question: If something’s not working, how do you know when it’s time to walk away?
This week, in episode 157, Liz Picarazzi, Sarah Segal, and Laura Zander wind up talking about artificial intelligence. They conclude that the time has come for business owners to take AI seriously. Laura says she’s already experimented with using ChatGPT to create lists, to write product descriptions, and to write a marketing plan for a new product. She even used ChatGPT to prepare a presentation for her staff about how to use ChatGPT. She did this in part to reassure them that they don’t have to fear losing their jobs. “What I told the team is, ‘It's a nail gun,’” says Laura. “‘Sometimes you need to use a hammer, because it needs to be perfect, and it needs to be exact. Sometimes you just need a damn nail gun, and you just want to pop it through. And that becomes the skill. The skill becomes: When do I use the hammer and when do I use the nail gun?’” On their way to the conversation about ChatGPT, Liz, Sarah, and Laura consider the various ways business owners can tap expertise, including through advisory boards, through business groups, and with strategic weekly lunches. Plus: Laura explains why she likes to hire people even when she doesn’t have an opening.
This week, Lou Mosca, who runs American Management Services, a consulting firm that helps businesses improve their performance, tells Loren Feldman why he doesn’t accept excuses from his clients. Whatever the economy or the labor market throws at them, Lou says, the owners control what happens within their own four walls. We also talk about why he always comes back to encouraging his clients to get in their cars and visit customers, why he thinks your best prospects just may be former customers, what he’s learned recently about digital marketing, and what every business owner should be tracking in these unusual times.
This week, in episode 156, we meet Jennifer Kerhin, the newest addition to the 21 Hats Podcast team. Jennifer’s business, SB Expos and Events, is an event-management business that survived the shut down in 2020 and has grown to more than $3 million a year in revenue. When COVID first hit, Jennifer tells Jay Goltz she really thought it would put her out of business; in the end, she says, it made her stronger. Even so, she is very much stuck working in her business, while looking for ways to extract herself from day-to-day tasks someone else could handle. But how do you free yourself up enough so that you have the time to put the people and systems in place that you know you need? And how long should that take? “I hate to tell you,” says Jay, “it took me 10 years. But I'm going to help you here, so it's going to take you 10 months.”
This week, in episode 155, Hans Schrei and Shawn Busse talk about why they put their businesses through accelerators, and Paul Downs explains why he might have done the same thing if accelerators had existed back when he started his business—”although,” he says, “I was probably too dumb to realize the value of it.” Hans, who just completed a 13-week accelerator program with his partner, Luis, also tells us how Wunderkeks fared while he and Luis were in the program, what they got out of it, and why they felt it was worth giving up the equity that was the price of admission. Plus: why Shawn went to an employee’s college graduation and how Paul managed to take a vacation. Oh, and Paul also talks about what surprised him about the recent 21 Hats event in Chicago.
Gene has a problem with it. He doesn’t think it goes far enough. That’s because he thinks it gives businesses with fewer than 25 employees an unfair advantage. Gene also warns that several “huge tax increases” are looming for small businesses -- but are they really tax increases? Plus: striking the right balance between salary and commission when paying sales people.
This week, for episode 154, we did something different. We recorded this session in Chicago at our very first 21 Hats in-person event. In May, some 20 impressive entrepreneurs from around the country, from different industries, with businesses of different sizes and stages, gathered to talk shop for three days. The last thing we did was to record this episode in which we gave the participants the opportunity to ask the podcast regulars anything they wanted. Those regulars included Jay Goltz, Sarah Segal, and Dana White, and the questions addressed everything from hiring to motivating to delegating to pricing to coping with stress to what they wished they’d figured out sooner and to what still keeps them up at night. And when there were no more questions, I asked those who attended the Chicago event what I could have done to make it better. That I would invite criticism in a conversation being recorded for a podcast audience, took some of the participants by surprise. But, as you’ll hear, it worked out pretty much the way I hoped.
This week, Ami Kassar tells Loren Feldman that in running MultiFunding, which helps businesses figure out their finance needs, he frequently meets business owners who know what they need to do but are reluctant to take that next step. One way to build your confidence, Ami says, is to make sure you really understand what drives your business model, which may require bringing in a fresh set of eyes, perhaps from a fractional CFO. Ami also talks about the current state of lending, his concerns about where the SBA is headed, and why business owner peer groups are so valuable.
So, I decided to give the 21 Hats Podcast crew this week off. Between the Memorial Day holiday and our first 21 Hats in-person event the previous week in Chicago—attended by five of the podcast regulars—it seemed the right thing to do. It also seemed like a great opportunity to reprise one of our favorite all-time episodes. It’s not a used episode; it’s a certified pre-owned episode, or better yet, a greatest hits episode. We first published it in December of 2021, and it features highlights taken from the podcasts we’d published up until that point that cover many of the risks and rewards of business ownership, including what it’s like to sell your business, to fire an employee, to risk your own home in order to get financing, and even to deal with serious mental health issues. If you’re new to the podcast, I think you’ll find that these conversations bring real context to the journeys of the entrepreneurs you’ve been following here. But even if you’ve heard some of these discussions before, I think you’ll find them a refreshing reminder that choosing to build a business can be a noble mission, but it generally doesn’t come with an owner’s manual. We’re all figuring it out as we go.
This week, in episode 153, William Vanderbloemen says good public relations is absolutely worth the time and money. Paul Downs says PR hasn’t worked for him. At this point, he says, there are all kinds of ways he’d rather spend his time and money. Meanwhile, Sarah Segal, who owns a PR firm, offers some tips on how to approach and how to employ a firm effectively. Along the way, we discuss what’s expensive when it comes to PR and whether owners can just do it themselves. Plus: Paul explains how he dug himself out of a sales hole by not doing anything differently. And we find out how the owners feel about all of the new ways they’re being asked to leave tips.
This week, Gene Marks tells Loren Feldman that he thinks the ban signed by Montana's governor is a political stunt that could do real damage to businesses that have come to rely on the app. And yet, there seems to be momentum for similar bans in other states and even at the federal level. Plus: how to avoid ERTC fraud, why bankruptcies are skyrocketing, and should the business community be doing more to warn against risking default?
This week, Shawn Busse and Loren Feldman talk to John Garrett about his contrarian approach to newspapers, marketing, and competition. Garrett has built a Texas-based chain of print newspapers that has managed to outcompete established news organizations and digital platforms for both community engagement and local advertising. Not surprisingly, when he first took out a $39,000 credit card loan in 2005 and started telling people that his business model would feature a monthly print publication that he would mail to everyone in his target communities for free, he didn’t get a lot of congratulations. And not everything he’s tried has worked. An expansion into Arizona, Tennessee, and Georgia, for example, failed early in the pandemic. But almost 20 years after its debut, a period during which most local publications have been in retreat, Community Impact is thriving. And from his seat as a publisher, Garrett offers a perspective on marketing that any business owner would be wise to consider.
This week, Gene Marks tells Loren Feldman that businesses should be making contingency plans in case there’s a default, especially if they rely on government contracts. Be careful how you spend and how you stash your cash. Plus: Gene gloats a bit about the end of the age of the worker (and then has some second thoughts). He also says reports of the death of the metaverse are greatly exaggerated and that it wouldn’t be so terrible if the government loses the ability to regulate.
This week, in episode 152, Jay Goltz, Liz Picarazzi, and Sarah Segal talk about the inherent conflicts between being an entrepreneur and being a CEO—and the different skill-sets each role requires. Does it make sense for the same person to do both jobs? Is being CEO even a full-time job? And when does it make sense to replace yourself as CEO? Liz says she’s thought about it. Jay, not so much: “Could I have found somebody 10, 15, 20 years ago who was a better manager? Sure. But it just wasn't worth it.” Why not? “It's gonna cost you $250,000 a year,” Jay says. “Is it worth paying that?” Plus: Liz and Sarah talk about positioning a company to be acquired. And Sarah proposes a PR campaign for Liz’s package bins right on the spot.
This week, John Arensmeyer, CEO of the Small Business Majority advocacy group, and Loren Feldman talk about some of the most intractable problems confronting business owners. And John offers some reason for hope -- mostly, he says, because there’s a growing, bipartisan effort to level the playing field for smaller businesses. The debt ceiling, of course, is another matter.
This week, two special guests who have built highly successful companies talk about what they ultimately plan to do with those companies. Ari Weinzweig is co-founder of Zingerman’s Community of Businesses, a collection of mostly food-related companies that are an iconic part of Ann Arbor, Michigan. Brad Herrmann is co-founder of Text-Em-All, a software firm based near Dallas that helps organizations deliver personalized, informational, and emergency messages by text and by phone. Both Zingerman’s and Text-Em-All consider themselves purpose-driven. Both practice open-book management. And so, not surprisingly, the founders of both companies took a hard look at selling to an employee stock ownership plan, or ESOP, in the hope that the cultures they’ve created might live on. But both companies, independently, soured on the notion of creating an ESOP, one after spending more than $200,000 and coming within a week of closing the deal. And now, both have settled on a little known alternative, what’s called a perpetual purpose trust. So far, only a handful of companies have tried to create a purpose trust for this purpose, but Zingerman’s and Text-Em-All are taking the leap. As both Ari and Brad acknowledge, they’re kind of figuring it out as they go.
Show Notes:* In our conversation, Brad and Ari mention several places where businesses can learn more about perpetual purpose trusts, including Alternative Ownership Advisors, Common Trust, and an attorney, Christopher Michael. * Ari has written about the Zingerman’s perpetual trust in his own newsletter.
This week, Gene Marks takes Loren Feldman through a case study of how easy it is even for profitable businesses to get caught in a cash crunch. The problem, Gene explains, is that business owners often have to pay taxes on earnings that have yet to reach the owners. Where does the money go? To inventory, to capital expenditures, to accounts receivable among other places. How can owners avoid the crunch? By staying on top of their finances.
This week, in episode 151, our conversation starts with Shawn Busse and Jay Goltz trying to understand why CEOs keep going viral for their misguided attempts to rally the troops. Shawn suspects CEO screeds have always existed—they just haven’t been recorded. He also thinks they tend to come more from public company CEOs who are beholden to shareholders. Jay thinks they’re just morons. “I really don't understand how someone could be smart enough to run a big company like that,” he says, “and be so completely ignorant. It's shocking to me.” Of course, CEOs of both publicly owned companies and privately owned companies do have to do unpleasant things sometimes, but Shawn and Jay say they’ve learned from their own experiences handling layoffs and recessions. “Do we have to go out of our way to be callous about it?” Jay asks. “I don't think so.” Plus: the very different ways Shawn and Jay manage their hiring processes. Oh, and, what would happen if Jay applied for a job at Shawn’s business?
Yes, demand is tapering, and a recession is looming, Gene Marks tells Loren Feldman, but this is a great economy and a great country and people should stop complaining! Plus: Gene explains how some business owners get the state to pay for their employee training, how restaurants are finally adopting technology, and how to make sure your employees aren’t stealing from you. One tip: if you think an employee is stealing from you, send the employee on vacation.
This week, in episode 150, Stephanie Stuckey tells Paul Downs and Liz Picarazzi how she and her partners have taken their business from $2 million in annual revenue to more than $13 million in three years. What’s frustrating, she says, is that she could be selling a lot more pecan snacks and candies. But with production at capacity, she’s not doing much sales outreach until they can fully revamp their manufacturing operation, which will require a significant investment. “I spend my days doing financial paperwork,” Stephanie says. Plus: Liz explains why her business picks up when the weather warms up, and after a slow start, Paul gets a boost from a big manufacturer.
This week, in episode 149, Jay Goltz tells William Vanderbloemen that even with an inventory glut, a cash crunch, and a weakening economy, he’s not going to stop buying goods for his home store: “It's kind of like cutting Samson's hair,” Jay tells us. “I don't want to mess with telling the buyer, ‘Stop buying stuff.’ Because that's the business we’re in.” All of which has Jay feeling some pressure, but he’s very glad he’s been maintaining a credit line equivalent to 10 percent of sales. Plus: William explains how hiring can go wrong even at a staffing company and how he managed to raise his prices without actually raising his prices.
Gene Marks tells Loren Feldman he’s not seeing it yet, but there’s reason to believe it’s coming. Gene also discusses the best password managers for businesses and explains why addressing the mental health of employees is a financial issue as well as an ethical issue and offers some suggestions. Plus: he says he expects unlimited paid time off to remain a much-sought-after benefit for employees even though in many ways it favors employers.
This week, in episode 148, Paul Downs, Sarah Segal, and Laura Zander discuss how they think about the possibility of recession: Do they proceed with planned hires? Do they continue to spend on marketing? Do they look for unexpected opportunities? In addition, Sarah, having recently taken back ownership of her PR firm, asks Paul and Laura how they pay themselves, how much cash they keep on hand, and whether they think she should expand her offerings to include digital marketing. Plus: Laura, who’s acquired several businesses over the years, explains what she looks for, how she decides how much to pay, and why she’s come to see acquisitions as necessary for the survival of Jimmy Beans Wool. As usual, all three owners are remarkably generous about sharing their thinking and even their numbers.
This week, Mel Gravely, CEO of Triversity Construction in Cincinnati, tells Loren Feldman why he still sees a recession looming—even though 2023 has been good so far, and he still has a solid backlog. He also talks about how he’s addressing the industry’s long-term labor issues, how Triversity lands new business, and what he’s doing to prepare for that recession.
This week, in episode 147, Paul Downs tells Shawn Busse and Jay Goltz that his year has not gotten off to a great start. This was supposed to be the year that Paul unleashed a bold, new marketing campaign that would put his business on an entirely new trajectory—and perhaps it still will be. But for the moment, his revenue has fallen considerably short of his expectations, which has presented him with an unwelcome choice: Should he hold-off on the marketing campaign? Or should he cut his own salary? Along with discussing Paul’s decision, we also talk about the process of rethinking a website, how best to make use of LinkedIn—it’s a gold mine for both business development and recruiting, says Shawn—and why Paul and Shawn continue to perform their own HR chores.
This week, Gene tells Loren Feldman why he hates the new Illinois law that requires businesses of any size to offer employees up to 5 days a year of paid time off — time that can be used for any purpose without explanation. Gene also suggests six things all owners should do if they have any thought of one day selling their businesses. And he explains his list of 10 tax-related numbers that he says every owner should know.
This week, in episode 146, Jay Goltz and Laura Zander talk about the limits of their own management. Once a business gets past a certain size, no owner can do everything or even be aware of everything. But where do you draw the line? Does the owner need to be conversant with most aspects of management, marketing, and finance to oversee the business? This came up, in part, because Jay told us recently that his framing shops routinely ask customers how they learned of the business and that a recent review indicated that his social media efforts were not having an impact. But when asked about those efforts, Jay wasn’t entirely sure what they consisted of or if they even existed. Perhaps surprisingly, it also became clear that Jay wasn’t all that interested in learning more. It was working well enough, he’d concluded, and that was all he needed to know. And that’s the starting point for today’s main conversation. Along the way, we also address such questions as: Where’s the line between being a manager and being a therapist? Do owners need to be passionate about their businesses? What does the phrase “people over profits” really mean? And while “the customer is always right” has become a cliche, is it really a good policy?
This week, in the aftermath of the Silicon Valley Bank collapse, Gene Marks says he banks at Wells Fargo — but that’s not what he recommends. His suggestion: Find a good community bank, spread your money around to play it safe, and then relax. He also says you should consider going to a four-day work week. And not because it’s good for your employees, but because it’s good for you.
This week, in episode 145, Hans Schrei explains why he’s pursuing a deal with Costco and why his vision is to get Wunderkeks cookies into every supermarket in the country. When Jay Goltz counters that instead of thinking big, or thinking small, maybe Hans should think medium, Hans says that may no longer be possible with consumer packaged goods: “The little brand that grows and thrives by growing little by little doesn't really exist any more in this space,” he says. Underlying the discussion of how fast Hans wants Wunderkeks to grow and how quickly he wants to exit are the stress-related mental health issues that he’s discussed previously on the podcast and the fact that his partner, Luis, is in the U.S. on an entrepreneurial visa, which means that if the business were to fail, they might have to leave the country.
This week, Gene Marks and Loren Feldman discuss what it means for small businesses that some tax deductions are going away, some new regulations are arriving, and Joe Biden has released a budget proposal. Gene also counters the Bare Minimum Monday meme with a suggestion for what practitioners of Bare Minimum Mondays can do on Tuesday.
This week, Shawn Busse and Loren Feldman talk to Jeff Braverman about how he walked away from a career as an investment banker and went to work in the family’s nut store, the Newark Nut Co. “My dad and my uncle told me I was nuts,” says Jeff. But with an instinct for taking risks—like acquiring the URL Nuts.com—Braverman has turned the family business into an internet juggernaut, unleashing years of explosive growth. And despite being a former investment banker, he’s managed to do that without taking any outside capital. And he’s far from finished. “To this day,” he says, “we're doing deep brand research: What is Nuts.com? What can it be? Can it scale? Can it transcend just the word nuts?”
This week, Gene Marks tells Loren Feldman that too few business owners really know how their business is performing. He suggests three reports that they should be reviewing -- beyond their monthly financials -- if they want to get a better grip on managing their business. Plus: Gene explains how businesses can save money on energy and why everyone should hire a CRM consultant (like Gene, for example).
This week, Liz Picarazzi and Sarah Segal talk about their attitudes toward growth, including how they set goals, the tension between revenue and profit, deciding when growth requires additional bodies, choosing between contractors and employees, and how they would use the money if someone were to give them a million dollars to invest in their business. Plus: What will it take for them to consider themselves successful?
If, like Gene Marks, you think dealing with employees is a pain, Gene has a suggestion for you: professional employer organizations, or PEOs. It’s a way to outsource all of the functions of HR—even including, if you want, health insurance. Gene also talks about why too many businesses ignore the many resources government has to offer business owners, why it’s time to start preparing for a government shutdown, and why Kevin O’Leary--aka Mr. Wonderful--is a buffoon.
This week, Shawn Busse and Loren Feldman are doing something a little different. This is the first in a series of episodes we’re calling Marketing Workshops. In an attempt to confront one of the biggest pain points business owners face, we’re offering a series of conversations with owner-operators about their marketing experiences: what’s worked and what hasn’t. We’re starting with Grayson Hogard, co-founder of Grove Cookie Company. For Grayson and his wife, Marie, the company is a bootstrapped side hustle, but in a very short time they’ve come to some very smart conclusions about their marketing that might seem counterintuitive at first. Most importantly, they’ve figured out that the most effective sales channel for their cookies is, of all places, LinkedIn.
This week, Gene Marks and Loren Feldman talk about why tipping is a terrible system that we probably will never change, why Gene believes giving up a real office for a virtual office didn’t save him money, and what the purchase of mens underwear can tell us about the economy. Plus: Gene says there are 27 things businesses can do with ChatGPT right now—although he does offer a few caveats.
Last week, Jay Goltz continued his exploration of employee ownership, flying to Portland to meet up with Shawn Busse and Jim Kalb, a friend of 21 Hats who has already sold a portion of his business to his employees. The three owners planned to attend a conference promoting employee stock ownership, but things went somewhat awry. Jay and Shawn left the conference early, Jim canceled his flight, and as has happened before in his brushes with ESOP professionals, Jay walked away feeling convinced—convinced, that is, that an ESOP probably isn’t right for him. Two days later, we taped this podcast episode, which quickly turned into one of the more raucohttps://21hats.com/us conversations you are likely to hear about a somewhat technical business topic—although we did manage to find some clarity in the end. In Jay’s words, we agreed to agree.
Along the way, we confronted quite a few relevant questions, such as, do ESOPs have to be so confusing? Are the professionals who pitch ESOPs trying to make them seem complicated? If Jay wants to sell 30 percent of his business to his employees but continue running it, how much control would he have to give up? Will an ESOP make life easier or harder for Jay’s two sons in the business? Instead of an ESOP, could Jay accomplish most of what he wants to accomplish by setting up a profit-sharing bonus plan through his 401(k)? Hanging over the conversation was a larger, more philosophical issue: What exactly do business owners owe their employees? And whatever those obligations are, do they extend beyond the sale of the business? Do they extend beyond the grave?
This week, Gene Marks and Loren Feldman talk about what Gen Z values in a job. The research suggests it’s not the job -- it’s more about people and meaning. And that’s good news for smaller businesses, because those are things they can offer. But you might want to emphasize that in your job descriptions. Plus: Is this recession happening or not? And what will ChatGPT’s upending of search mean for all of the businesses who’ve been investing in SEO? They’re not going to be happy, says Gene.
This week, in episode 142, Sarah Segal tells Shawn Busse and Jay Goltz why she’s decided to take her public relations business back after selling it two years ago to a larger firm so it could handle the back-end stuff and allow her to focus on public relations. For Sarah, the immediate result of the decision to break away has been an exhausting few months starting over, including reincorporating, finding health insurance, and reducing her own pay. Meanwhile, Jay suggests an old-school marketing tactic that involves leveraging an envelope, a stamp, and the post office. And Shawn explains how he created a sales process that has allowed him to remove himself from day-to-day sales. Plus, a listener asks the three owners, “When do you know if you've made it? Or do you never know?” Shawn, Jay, and Sarah—three owners at very different stages of building a business—offer three very different answers.
Well, it is, but after spending a month in London, Gene Marks says inflation, regulation, and entitled employees make it even worse there. In fact, Gene says he’s going to stop complaining about conditions in the U.S. (We’ll see.) Plus: why Gene thinks even small businesses should offer unlimited PTO, how to make sure you don’t fall prey to one of the Employee Retention Tax Credit scams, and Gene’s list of things a small business can do with ChatGPT.
This week, in episode 141, Shawn Busse, Paul Downs, and Jay Goltz go right to the bottom line. Shawn points out how easy it is for businesses to fool themselves into thinking they’re more profitable than they really are. Paul talks about how margins can vary from year to year, especially if an owner decides to invest in improving the business—as Paul’s doing right now. Jay says he’s long sought a 10-percent profit margin, but so far, he hasn’t managed to get there. Plus: Shawn explains how he solved his accounts receivable problem. And have you looked at the 401(k) accounts of your employees lately? If not, there’s a good chance you’re going to find that they’re not saving a whole lot. Is that just the employee’s problem, or is it also the owner’s problem?
This week, 21 Hats columnist and finance expert Ami Kassar assesses the state of small business lending with Loren Feldman. Among other things, they discuss why it’s important to manage your EIDL loan carefully, how much of a line of credit every business should have, how to get a zero-percent-down loan from the SBA, and how much progress Ami has made toward firing himself.
This week, in episode 140, Shawn Busse, Liz Picarazzi, and Sarah Segal talk about how long to keep trying when a product isn’t selling the way you expected. For Liz, the problem product is her package locker, which is designed to defeat porch pirates but hasn’t really taken off—especially considering how widespread the concern is. Could the glitter-bomb guy be the answer to Liz’s marketing challenge? Or is it time for her to back off? Plus: In the age of Zoom and remote workers, what have the owners figured out about running effective meetings? And if you're pricing a range of services in a proposal, do you price your offering a la carte? Do you always charge the same prices? And is there a way to ease a client into a monthly retainer?
This week, Gene Marks and Loren Feldman discuss an “inconvenient truth” about Salesforce CRM, which is that it’s probably not right for most non-corporate businesses. Already using it? Gene explains how to assess whether it’s worth making the switch to a more affordable platform. Plus: Gene thinks the Department of Labor’s new worker-classification law will be a disaster but suggests some fixes. Gene also has some thoughts about ChatGPT: real potential, not there yet.
This week, in a special bonus episode, Michael Brown, co-founder of an innovative company called Teamshares, explains how he and his co-founders are bringing a fresh approach to a big challenge. Teamshares is buying the businesses of Boomer owners who are ready to retire but, in many cases, struggling to sell. Once the business is bought, Teamshares is turning the employees of those businesses into employee-owners, which is intended to strengthen the businesses while also addressing income inequality. So far, starting in 2020 and flying largely under the radar, Teamshares has already bought more than 60 businesses in more than 40 industries, most ranging between $1 million and $5 million in revenue. Along the way they’re learning some intriguing lessons about what it takes to build a business.
This week, in episode 139, Jay Goltz, Dana White, and Laura Zander have a wide-ranging conversation that starts with the challenge of pricing. Do you set prices based on what you think the market will bear? Or do you set prices based on your own rising costs and what you need to charge to make a profit? And how much profit should a business expect to make? Along the way, the owners also discuss why Laura wants to keep buying businesses (don’t tell her husband, Doug), what Dana needs to do to get her new salon open at Fort Bragg, and why both Dana and Laura are going all-in on influencer marketing. Jay, on the other hand, isn’t entirely convinced that social media marketing works for his picture-framing business. Plus: Should a business owner know every employee’s name? What if you have 130 employees?
John Arensmeyer, founder and CEO of Small Business Majority, an advocacy group for entrepreneurs and businesses, talks to Loren Feldman about how businesses are faring, what issues they are most concerned about, and where his organization is focusing its energy. Among other things, they discuss access to capital, the need for immigration reform, who benefits from non-compete agreements, California’s experiment in fast food regulation, and the Labor Department’s approach to independent contractors.
This week, in episode 138, Shawn Busse, Liz Picarazzi, and William Vanderbloemen discuss what it’s been like trying to make sense of employee compensation in a time of COVID, the Great Resignation, inflation, and a looming recession. Shawn’s business model is evolving, and he’s trying to adjust his mix of employees to fit the new model with as little disruption as possible. Liz is expecting a year of big growth and is assessing how that will affect her staffing needs—especially as she introduces new benefits, including health care. And William is trying to create a more sustainable compensation structure while also breaking his employees’ expectation that they will always get a year-end bonus. Plus a listener asks: What tasks are the owners still doing, even though they know it’s not worthy of their time? (Aside from participating in this podcast, of course.)
This week, Gene Marks tells Loren Feldman that the politicians behind Secure 2.0 are smarter than you think. The omnibus spending bill that recently became law includes a slew of changes to the rules that govern retirement benefits. The changes are designed to encourage both employees and owners to sock away more money, and they include a $1,000 tax credit per employee for owners who match employee savings. Plus: are non-compete clauses of any value to small businesses? And the IRS blinks on its requirement that third-party payment platforms issue 1099-K forms.
This week, in episode 137, Jay Goltz explains how he got interested in selling a percentage of his business to his employees and why he quickly lost interest once he started reading books, attending seminars, and talking to accountants and lawyers who specialize in employee stock ownership plans. To Jay’s ear, they all made ESOPs sound expensive, complicated, and risky. This was not something he needed to do. So why go to the trouble? Why take the risk? But he kept asking questions, and over time, he sensed that many of the problems he was being warned about didn’t have to be problems. As of now, he’s pretty much concluded that an ESOP could help him secure retirement for his employees while generating more profit for his business. In fact, he says, “I'm confident I can make more owning 70 percent of the company than I am now owning 100 percent.” But he still has a few lingering questions, which is why we invited Corey Rosen to join the conversation. Corey helped draft the legislation that created ESOPs, he's the founder of the National Center for Employee Ownership, and he literally wrote the book on how the plans work. All of which led to an inevitable question for both Jay and Corey: If ESOPs are so great, why are there so few of them?
Show Notes:
Here’s Corey Rosen’s most recent book, written with John Case: “Ownership: Reinventing Companies, Capitalism, and Who Owns What.”
Here’s a previous book Corey wrote with Scott Rodrick: “Understanding ESOPs.”
And here’s a book written by Jack Stack and Bo Burlingham: “A Stake in the Outcome.”
In our last episode of the year, Gene Marks tells Loren Feldman he actually thinks business owners will like the new law in California that will create councils to regulate the fast food industry. In fact, Gene thinks there’s a chance it will succeed and spread to other regions and other industries. He also explains why he thinks businesses should be on Yelp, why he’s still excited about what Elon Musk is doing with Twitter, and why he thinks interest rates will be the small business story of 2023.
This week, in episode 136, Shawn Busse, Jay Goltz, and Sarah Segal talk about what they hope to accomplish in 2023. Sarah’s moving into new offices, aiming for 20-percent growth, and hoping to land a chocolate company as a client. Shawn’s looking for new space, too, and attempting to reposition his business to shake the corrosive effects of the pandemic. And Jay’s employing a methodical 12-step process to assess how his business is performing: Hiring? Check. Pricing? Needs work. Inventory levels? Way out of line. Office technology? Major problems. And then there are his ongoing efforts to mentor his two sons in the business and prepare for the inevitable. These days, Jay tells us, he’s especially careful when getting in front of buses. If you’ve been listening to this podcast, you know our business owners discuss their journeys with unusual candor. But in some episodes we go especially deep. This is one of those episodes.
This week, Gene Marks and Loren Feldman talk about how charging by the hour actually punishes you for being good at your job—but there’s a good reason Gene does it anyway. Plus: Gene also discusses his one concern about hiring ex-offenders and issues a warning to business owners about their remote employees. Gene thinks they’re probably stealing from you.
This week, in episode 135, Shawn Busse, Paul Downs, and Liz Picarazzi talk about their plans and goals for 2023. Shawn, whose marketing efforts still haven’t recovered from the pandemic, is hoping to build on the success of a recent event. Paul, coming off his best year ever, is investing $150,000 in a marketing campaign, including a new website targeting a different set of customers. And Liz, too, is attempting to shift her customer base, in her case from residential to municipal work. More immediately, however, Liz, who does not relish dealing with legal issues, has to decide how to confront a copycat competitor.
Gene Marks tells Loren Feldman that he’s concerned that not enough business owners are thinking about the future and preparing for succession. Which leads to an obvious question: Does Gene have a succession plan? Hmmm. Plus: Gene has some suggestions for how businesses can better manage their relationships with vendors and suppliers. And what lessons should we take from the rampant fraud being revealed in the PPP program?
This week, in episode 134, Shawn Busse, Jay Goltz, and Laura Zander talk about the buying and selling of businesses. Laura thinks her recent purchase of a small distribution business could change the trajectory of her whole company, helping her finesse the challenge of selling wholesale products to her retail competitors. Jay, meanwhile, has been trying to help an aging business owner sell the kind of business that too often just fades away. Underlying both discussions is an intriguing question: While it’s common practice for owners trying to sell their business to keep the potential sale a secret, fearing employees might otherwise flee, is that really the best approach? Or is it actually a betrayal? Plus: We answer a listener's question about finding the right balance between being a kind boss and being a pushover. And we play a quick game of Who Said It: Elon Musk or Mr. Burns?
This week, in episode 133, Paul Downs and Sarah Segal talk about their experiences negotiating, what they’ve learned and where they’ve struggled. One key factor, of course, is defining what constitutes a successful negotiation. As Paul points out, one definition is squeezing every last penny out of the other side. That is not Paul’s definition, especially when negotiating salary with a new employee. Sarah, meanwhile, discusses the tactics she uses to try to guide potential clients to the price and options she hopes they will accept. Plus: Sarah explains how she picked her new office space, and Paul explains why his experience with a Vistage peer group has been life-changing.
This week, Gene Marks tells Loren Feldman that he’s had it with “quiet quitting,” side hustles, and employees who won’t go the extra mile. It’s time, he says, for them to get to work. And if they don’t? Gene says they’re going to be looking for work, and it could happen much sooner than they realize. On a related note, Gene is also very excited about the “hardcore” changes Elon Musk is bringing to Twitter. We’ll see how that works out!
This week, in episode 132, Liz Picarazzi, Hans Schrei, and Laura Zander talk about something they have in common: They all own and run their business with a partner who also happens to be a spouse. Which suggests some interesting questions: Is someone in charge? How do they divvy up responsibilities? What do they talk about? What do they fight about? Do they fight in front of the employees? How do they make decisions? Who does the dishes? Do they ever wish they were not in business with their spouse? Do they know what would happen to the business if they were to divorce?
You want to negotiate with Blue Cross every year? Go ahead. Gene Marks tells Loren Feldman he's found an alternative that he believes allows him to take care of his employees without the hassle of actually buying health insurance. Plus: Why Gene doesn’t discount his services for nonprofits and what he thinks is the most important takeaway for business owners from last week’s midterm elections.
This week, in episode 131, Shawn Busse tells Jay Goltz and Sarah Segal that he sees all kinds of opportunities for small businesses, including his own, in the coming wave of climate-related government spending and tax credits. Count Jay among the convinced. He’s got four buildings, five vans, a truck, some Sprinters, and a parking lot where he could put a charging station. If there’s government money available for upgrades, he asks, “Why wouldn’t I do that?” Plus, Jay explains how he’s rethinking his search for an HR person. And Sarah tells us she’s ready to meet in the metaverse.
This week, Gene Marks tells Loren Feldman that there are still lots of ways to save on taxes this year, but he also issues a warning: It’s a mistake for owners to just take their financials to the same CPA every year and assume he or she knows everything. Every few years, Gene says, you should take your returns to a different accountant and see if fresh eyes spot alternative tax opportunities for you to consider. Plus: Why Gene thinks you should ignore those third-quarter GDP numbers, and why he says there are times when owners should fight back rather than accept a bad online review.
This week, in episode 130, Sarah Segal, Jay Goltz, and special guest Leo Bottary have a hype-free conversation about why peer-advisory groups like Vistage, YPO, and EO can be life-changing for business owners and why they’re not for everyone. Sarah has been wondering if they’re for her. Jay, who’s been in six different peer groups, says it can be worth the price of admission just to see how other owners run their businesses—but there are reasons he keeps leaving the groups he joins. And Leo is a former Vistage employee who has written multiple books on peer groups and has built a related consulting practice. Surprisingly few business owners belong to a peer group. Are they missing out? All three of my guests suggest questions to consider before deciding for yourself.
Kurt Wilkin, co-founder of HireBetter, tells Loren Feldman he thinks concerns about a recession are largely media-driven, but if your business is slowing, this might be a good time to reevaluate your team: Are you happy with everyone you’ve hired? Plus: What does it mean that wages kept rising in the third quarter? Should job listings include salary ranges? And what would Kurt tell business owners who struggle with compensating themselves?
This week, in episode 129, Hans Schrei tells Shawn Busse why this has been a difficult year at Wunderkeks—despite many outward signs of success. It has to do with buying into the need to raise money and shoot the moon. It has to do with accepting the accolades that come with entrepreneurial achievement and then questioning your own self-worth when those accolades stop coming. It’s what Hans calls, “the miracle worker complex.” Hans and Shawn also discuss what it means to rely upon a sales platform like Amazon. Do you own the customer or does Amazon? And Shawn explains the biggest takeaway from his most recent Vistage meeting.
Before you spend more on technology, he says, you might want to figure out how to make the best possible use of the tech you already have. Crazy, huh? Gene also talks about the key elements of a buy-sell agreement, how to get your employees to actually use your CRM system, and whether all of our ever-expanding array of productivity tools actually help productivity.
This week, in episode 128, Shawn Busse, Paul Downs, and Liz Picarazzi talk about why it’s so easy for tension to break out inside a business. Liz sees tension brewing between her people in the office and her people in the field. Shawn often sees friction at businesses between sales and those who have to deliver what sales sells. Paul says there’s always the potential for tension when a project gets handed from one set of workers to another, and he’s created a very deliberate process to address it. We have, he says, “really tamped down the civil wars and started solving the problems, as opposed to letting them fester.” Plus: Are Shawn and Liz going to hit their numbers this year? And have the owners seen their health insurance rates for next year?
Founder of entrepreneurial advocacy organization Right to Start, Hwang suggests bipartisan policy changes that would help Americans build more businesses. He also talks about what he learned about entrepreneurs on his recent cross-country roadtrip, why funding of U.S. businesses is broken, and what Americans really think of business owners.
This week, in episode 127, Dana White tells Paul Downs and Jay Goltz how her move to Dallas is going, including hiring a manager, firing a publicist, tweaking her business model, and for the first time, confronting competition. Dana also explains the surprising way she managed to get the financing to open her first salon on a military base, Ft. Bragg, which she now thinks could be up and running by the end of the year. Plus: Paul has to make adjustments to handle a sudden influx of business. And Jay is still looking for a head of HR. Should he post the ad on ZipRecruiter or Indeed? Should he offer a salary range in the ad? And is it reasonable for him to expect a follow-up email after an interview?
This week, as many businesses find out what they’ll pay for health insurance next year, Gene Marks and Loren Feldman talk about how businesses can save money. Gene explains why self insurance has become more feasible for smaller businesses and why he thinks it makes sense to offer employees better health coverage instead of a pay increase. Also, it’s probably time to revisit your workplace drug policies. And Gene and Loren discuss why the concerns of small businesses often get overshadowed by those of big businesses.
This week, in a special bonus episode recorded right before Labor Day, Seth Goldman talks about getting the disappointing news that Honest Tea, the brand he built and sold to Coca Cola, was being discontinued—and how it took him about two weeks to decide to create another tea business, Just Ice Tea, to fill the shelf space that Coke was vacating. Along the way, Goldman talks about why it made sense to sell a mission-driven business to a soda company, what he wishes he had done differently in the sale, what it was like being a Coke employee, what he’s been doing since leaving, how the beverage industry has evolved, and whether he’ll end up selling this business to Coke, too.
This week, in episode 126, Karen Clark Cole, Jay Goltz, and Sarah Segal discuss whether their businesses are meeting expectations and how that’s affecting their plans for next year. They also talk about how to handle an employee who doesn’t deliver, whether now is a good time to hire, and—in an answer to a listener question—how to make the transition from using contractors to hiring employees. And Karen explains why employee utilization—that is, what percentage of her people are actually billing clients—is the most important metric she tracks and one she tracks on an hourly basis. Plus: Notebooks or Notion? All three owners tell us how they try to stay organized.
This week, Loren Feldman speaks with Tracy Bech, who is CEO of Starboard Collectives and who specializes in helping business owners who don’t have a financial background (she understands: she was once one herself). Tracy talks about the two most important ratios for business owners to watch if they think we’re heading into a recession. And she also talks about why she actually likes recessions—or at least sees opportunities in them.
This week, in episode 124, Shawn Busse, Liz Picarazzi, and Hans Schrei debate the merits and risks of taking outside capital. Clearly, it makes sense for some businesses. But what are the right circumstances? What are the alternatives? And what do you need to understand before going to the dance? For example, what are the dynamics of the entrepreneur-investor relationship? Are the entrepreneurs hoping the investors will bestow an opportunity upon them? Or is it actually the entrepreneurs who have an opportunity to offer? And who pays for the coffee? Plus: What do you do on those days when no one seems to be following your lead and the entrepreneurial loneliness sets in?
This week, Gene Marks and Loren Feldman talk about what business owners can do to protect themselves in the current environment of rising rents and increased volatility. Plus: What explains the recent boom in startups? And will it last? And what the Fed’s rate hikes mean for businesses. Also: you can’t just set your website and forget it.
This week, in episode 124, Karen Clark Cole, Jay Goltz, and Sarah Segal talk about hiring an HR person. First, how do you handle HR issues before you can afford HR people? Is software the answer? At what size does a business need a full-time person? Do you hire someone who has experience but who might not be used to getting his or her hands dirty? Or do you hire someone you can mold to fit the culture of your business? Jay, who likes to say the entrepreneur is often the worst person to interview candidates, is currently interviewing candidates to be his head of HR, and he’s a little surprised at how few resumes he’s been getting. Plus: Sarah’s looking for office space and not finding much that would be acceptable. And how are Karen and Sarah doing now that, technically, they have been employees in their own businesses for a year?
Signed by Governor Newsom on Labor Day, California’s new fast food law creates committees, among other things, to set an industry-wide minimum wage. The plan sparked lots of outrage, but Gene Marks explains why he thinks it’s worth a try. He also notes that it could well be coming to a state near you. Plus: Gene also makes the business case for paid parental leave while also raising some interesting questions, including this one: If you offer paid leave to new parents, is that fair to employees who don’t have children? Gene also explains why he says buying Salesforce’s new small-business CRM is like ordering a salad at McDonald’s.
This week, in a special bonus episode, Jason Fried talks about why things got crazy at software maker Basecamp and what it has meant for the business. As you may recall, in the spring of 2021, Fried, CEO and co-owner, issued a blog post edict eliminating a slew of benefits, shutting down a committee that had been attempting to address diversity issues, and barring discussion of all social or political issues on work forums. The email produced a backlash that culminated in a third of the company’s 60-some employees choosing to leave. The rupture was especially stunning coming at Basecamp, which has since re-branded by returning to its original name, 37signals, and which has long had a reputation for treating employees well, including offering remote work long before it was commonplace. When the story broke, some business owners applauded Fried for taking a stand. Others wondered how any policy that resulted in the departure of a third of a company’s employees could be worthy of praise.
Show notes:
Here’s the blog post Jason Fried sent out announcing the policy changes: https://world.hey.com/jason/changes-at-basecamp-7f32afc5
Here’s a story that recounted the backlash as it was happening: https://www.theverge.com/2021/5/3/22418208/basecamp-all-hands-meeting-employee-resignations-buyouts-implosion
Jason Fried is author or co-author of several books, including, “It Doesn’t Have to Be Crazy at Work.” https://basecamp.com/books/calm
This week, in episode 123 and in light of reports that half of the U.S. workforce has “quietly quit” their jobs, Shawn Busse, Paul Downs, and William Vanderbloemen talk about the latest rage: Is quiet quitting something new? Is it just a media creation? Have Shawn, Paul, and William experienced it in their businesses? And who’s to blame? Plus, the three owners explain how they hire for engagement and how they’ve changed their hiring processes in response to the pandemic and the labor shortage. For example, Paul explains why, in this brave new world, he continues to flip conventional wisdom on its head: Instead of hiring slow and firing fast, he’s been hiring fast and firing slow. And he says it’s working.
How much control do you need? How much risk can you handle? This week, Ami Kassar, a small business finance expert, recalls feeling inadequate when he saw other entrepreneurs raising lots of money and going for broke (and sometimes getting there). He began to realize that there are different entrepreneurial personality types, and he’s developed a survey that can help you understand your own entrepreneurial instincts. The founder of MultiFunding also discusses how willing banks are to lend right now, what businesses should do to prepare for a downturn, why it’s important to manage your EIDL loan carefully, and whether it ever makes sense to turn to an alternative lender.
This week, in episode 122, Hans Schrei and Sarah Segal talk about what it takes to break into Costco. How do you get on their shelves? If you do get there, how do you make sure your product will fly off of those shelves? And if you succeed, will you have the financing you’ll need to ramp up production? Along the way, Sarah offers some tips on enlisting Costco influencers, and Hans explains the inner workings of Wunderkeks’ equity crowdfunding campaign, where you can invest as little as $150 and where the company hopes to raise $1 million. Plus: Sarah responds to a smart listener’s suggestion of how to avoid getting ghosted by potential clients after preparing elaborate and expensive proposals.
Show notes:
Here’s Wunderkeks’ investing pitch on Republic: https://republic.com/wunderkeks
Here’s the episode where we introduced Hans and Wunderkeks: https://21hats.com/wunderkeks-has-two-daddies/
And here’s the episode where Sarah talked about being ghosted by potential clients: https://21hats.com/trash-rats-and-garbage-juice-a-case-study-in-pr/
This week, in part because Loren’s on vacation, we’re offering a replay of an episode we recorded more than two years ago. It was one of our early episodes, and it was recorded shortly after George Floyd was murdered. In the episode, Karen Clark Cole, William Vanderbloemen, and Dana White talked about how they viewed their responsibilities as business leaders at such a fraught moment. What, if anything, were they saying to their customers? What were they saying to their employees? It started as a conversation, but Dana took the lead quickly and powerfully. She talked about what it’s been like to so often be the lone Black voice in the room. She talked about what it’s like for African-American employees to come to work and wonder where their company and their colleagues stand. She drew a line in the sand. “Why is it hard,” she asked? “You’re either over here, or you’re over there.” Even if you’ve already heard this episode, we recommend listening again—especially given that business leaders are again being asked where they stand on social and political issues, whether it’s about race or abortion or the climate or democracy. If you haven’t already heard the episode, we doubt you will soon forget it.
This week, in episode 121, Shawn Busse, Jay Goltz, and Liz Picarazzi discuss their succession options and—if they could go back in time—what advice they would give their early-stage selves. Liz would tell herself to get some help with administrative tasks, Shawn would tell himself to find a mentor (although he’s not sure he would have listened to the advice), and Jay would tell himself that there’s an obvious solution to the chaos caused by fast growth. Plus: How Liz changed the narrative after Citibin’s bout with bad publicity. And we have suggestions for a listener who asks: How do you know when it’s time to quit the day job?
This week, Gene Marks and Loren Feldman talk about the rise of “quiet quitting,” the new term for when employees contribute the bare minimum. They also discuss the phenomenon of bosses who come into the office to set a good example even as their employees phone it in from the beach. But most importantly, Gene points out what few others have noted, which is that the Inflation Reduction Act extends a huge tax break for business owners that was nearing expiration. And that’s just one of many aspects of the bill that Gene applauds. So would he have voted for the bill? You might be surprised.
This week, in episode 120, Shawn Busse and Paul Downs talk about what they’ve learned from their worst client experiences. Shawn, for example, tells us that he’s come to think about taking on a client much the way he thinks about hiring an employee. And Paul stresses the importance of watching what he says about difficult clients to his employees, because he doesn’t want to encourage a cynical attitude. From bad clients, our conversation shifts to bad partnerships. Even though their own partnerships ended poorly, both Shawn and Paul emphasize that having a partner can be invaluable in getting a business off the ground. In fact, Paul says he might even consider taking on a partner again. Plus, both Shawn and Paul explain why all the talk of recession is not giving them second thoughts about their ambitious marketing plans.
This week, John Arensmeyer, founder and CEO of Small Business Majority, an advocacy group for entrepreneurs and businesses, talks about what businesses can expect from the legislation coming out of Washington, D.C.—not just the climate, tax, and health care bill, but also the CHIPS and Science Act. In many instances, the benefits to business owners will come indirectly, he says, but they will come nonetheless.
This week, in episode 119, Liz Picarazzi tells Jay Goltz and Sarah Segal about her first brush with bad publicity. Liz’s debacle started with a negative post that appeared in a prominent local blog. It was about a Times Square pilot program for which her business, Citibin, is supplying trash bins. The problem? The bins were not being maintained properly, and there were photos to prove it. At the time we recorded this conversation, Liz was bracing for additional stories in both the New York Post and The New York Times. Both of those stories have since been published—we’ll talk about them in a coming episode—and you can find links to all of the coverage in the show notes. For Liz, perhaps the biggest challenge was defending her company without trashing her client.
Show Notes:
Here’s the Streetsblog post: https://nyc.streetsblog.org/2022/07/20/gross-clean-curbs-bins-show-growing-pains-in-times-square/
Here’s the New York Post story: https://nypost.com/2022/07/30/nyc-citibins-leaking-garbage-left-open-in-times-square/
And here’s The New York Times story: https://www.nytimes.com/2022/08/06/nyregion/new-york-city-garbage-containers.html
This week, Gene talks about how he recently had a mild case of COVID but worked right through it, no problem, which got him to wondering why employees—in his view—do not seem to be similarly dedicated. In fact, Gene believes that employees are using “COVID hysteria” as a pretext to avoid work and catch up on their TV watching. Plus, Gene explains why he thinks Wawa, a chain of convenience stores, is a good model for his own business. And he tries to make sense of a recessionary economy that produced more than half a million jobs in July.
This week, in episode 118, Jay Goltz tells Shawn Busse and Karen Clark Cole about a dream he had recently. It was a dream, of all things, about this very podcast, and on it, someone—it was a guy—was talking about how his business was faring: “I think I’m screwed,” he says in Jay’s dream. But who was it? And why was he screwed? Jay woke up before those answers were revealed. So we did some interpreting on this week’s real podcast. Spoiler alert: It wasn’t that hard to interpret! Plus: Shawn explains why he thinks his website is no longer performing. Karen explains why she thinks it’s actually easier to onboard an employee who will work remotely. And Jay and Karen discuss whether it’s time to give up on things going back to the way they were.
This week, Gene Marks and Loren Feldman try to make sense of where the economy is headed and what it means for business owners. Plus, Gene explains why he thinks some business owners may be fooling themselves about whether their business is growing. He also talks about a CRM tool that Google is giving away for free, as well as what you need to know to start a business.
This week, in episode 117, Paul Downs, Sarah Segal, and Laura Zander discuss their daily routines, how those routines have been affected by the pandemic, whether they think they’re working too much or too little, and whether they would join a peer group where they would be exposed to owners who are working harder and, perhaps, having greater success. Plus: Laura places her bet on influencer marketing, Paul says his new marketing campaign has already paid off, and Sarah explains why none of her employees have ever asked her for a raise.
This week, Gene Marks reports back from a conference of funeral directors and debunks a silly survey that predicts a bleak future for small businesses. Plus: How the rules defining full-time employees and contractors could be changing, why some business owners are giving up on their CRM systems too soon, and how a relatively new law can help businesses save money administering retirement plans.
This week, in episode 116, Jay Goltz, Liz Picarazzi, and William Vanderbloemen discuss how their businesses are holding up and whether they’ve gotten past the labor shortage (short answer: No). The conversation veers into a discussion of how to finance growth and what to do when your bank is unresponsive (find another one!). And then Liz explains her intense distaste for dealing with lawyers, accountants, and insurance agents and how she’s trying to cope with it. “Believe me,” responds Jay, “I haven't paid enough attention to certain things that I should have, and it's cost me. But yeah, we can't every day just do the inspiring, cool, fun, oh-my-God, we-had-a-big-sale, look-at-the-problem-I-solved thing. It’s all part of the package.”
Dashboard: Something Is Going to Happen
This week, Mel Gravely, CEO of Triversity Construction in Cincinnati, joins Dashboard to explain why—even though he has an extremely healthy backlog of work lined up for 2023—he’s more than a little concerned about where the economy is headed. He also talks about how the labor shortage in his industry started well before The Great Resignation and why he doesn’t see it ending any time soon. And then there’s the challenge of bidding for future contracts without knowing what your materials or labor are likely to cost. Plus: He talks about what he’s learned in the year since he published his book, “Dear White Friend,” in which he sought to start an honest conversation with other business owners about race.
This week, in episode 115, Shawn Busse, Hans Schrei, and Sarah Segal explain what they would do if I gave them $10,000 a month to spend on marketing. As we all know, there’s a lot going on right now. No one’s entirely certain where the economy is headed, and no one’s entirely certain where digital marketing is headed. So it seemed like a good time to ask our regulars where they would place their bets if we offered them each an imaginary pot of money to promote their brands. Spoiler alert: Their responses gave us a good sense of what these business owners think is working right now—and it’s definitely not billboards.
This week, Gene Marks and Loren Feldman talk about the continued rise of text message marketing and how it can be integrated with your CRM system. They also discuss why Gene warns businesses off of Twitter—even though he’s a power user. Plus: How do you plan for a recession and a labor shortage at the same time? And is that $10 billion in SSBCI money flowing yet?
This week, in a special bonus episode, Kurt Wilkin talks about how he helped build several businesses, including most recently a recruiting business called HireBetter, and explains why he hates most business books. It has to do with the attention deficit issues he, like many entrepreneurs, tends to experience. So when he decided to write a business book of his own, he kept it short, and he structured it so that you can find the parts that are most relevant to you and skip the rest. It’s called “Who’s Your Mike?” and it features chapters on the kinds of hiring and management challenges all entrepreneurs confront, including situations involving employees like Mike. Who exactly is this guy Mike? Oh, you know. He’s the incredibly loyal and hard-working employee who’s been with you from day one but who isn’t necessarily growing with the business. Says Kurt, “We all have, or have had, or will have a Mike.”
This week, in episode 114, we welcome another new panelist to the podcast, Hans Schrei, who is co-founder of Wunderkeks, an e-commerce bakery in Austin, Texas. Hans tells Jay Goltz and Liz Picarazzi why he and Luis Gramajo, his husband and co-founder, sold a business in Guatemala, immigrated here in 2019, and started a cookie business from scratch, going from selling at farmers’ markets their first year to doing more than $5 million in e-commerce last year. Hans also explains why he doesn’t think it’s enough just to make a delicious cookie, why he’s trying to raise seed capital, and what would happen to his visa if Wunderkeks were to fail.
Gene Marks, our man in London (at least for this week), tells Loren Feldman that small businesses in the UK are doing quite well, thank you! Marks and Feldman also discuss how your CRM system can help you fight inflation, the good news about bankruptcy laws, how to increase profits without raising prices, and whether it’s now okay to swear in the office. Cheers!
This week, in episode 113, Sarah Segal tells Shawn Busse and Paul Downs why she’s never articulated a set of core values for her business and why she’s thinking about doing it now. But she’s wondering whether establishing her values will really make a difference. Do employees care? Do clients care? Both Shawn and Paul say they do. In fact, Paul says his core values have been extremely helpful when it comes to recruiting. And Shawn says he thinks sharing values can be the best competitive advantage smaller businesses have. Plus: We get an update on how Paul’s big marketing initiative is going, and we follow up on why Sarah feels compelled to participate in almost all of her firm’s client calls.
“I don’t have the time to deal with them because my resources are limited,” Gene Marks tells Loren Feldman this week. But he’s just fine hiring Millennials, and he explains why. Plus: The cheap money days may be over, but there’s a silver lining to that: Venture-backed businesses may actually have to operate like real businesses. And Chewy offers lessons in both customer service and social media.
This week, in episode 112, we welcome a new regular to the 21 Hats Podcast crew: Sarah Segal, founder and CEO of Segal Communications, a public relations firm based in San Francisco. First, Sarah tells Jay Goltz and Liz Picarazzi how she built her firm. Then, Jay and Liz ask Sarah all of their questions about public relations: How much outreach should they do themselves? Should they hire a PR specialist or a full-service agency? Should they approach journalists directly or through a publicist? And most important, how much should it all cost? Plus: Why Sarah’s still figuring out how to attract new business.
This week, Gene Marks and Loren Feldman talk about whether it’s time to panic about inflation and recession, how smaller businesses are managing their inventories through these unpredictable times, why businesses that take digital payments through a service like Venmo are going to have to be more careful, and what, if anything, the metaverse is likely to mean for the typical small business.
This week, in a special bonus episode, Greg Wittstock, founder of Aquascape, explains how he invented the backyard pond industry, how he improvised a business model, and how he almost lost it all. After failing at franchising, Wittstock decided to give away his pond building expertise and marketing to landscape contractors in what he calls “a franchise system without a franchise fee.” And it worked. Always candid to a fault, he recounts how the business shot to $59 million in annual sales, why it then stagnated for 10 years, and what he ultimately figured out about social media marketing. Plus: he also explains why his first rule of customer service is: Don't give them what they ask for. Give them what they want.
Show Notes:
Here’s Bo Burlingham’s profile of Greg Wittstock: https://www.inc.com/magazine/20031101/aquascape.html
Here’s Greg’s video of Shaquille O’Neal’s pond installation: https://www.youtube.com/watch?v=Ti-k4LUQBNs
As listeners to this podcast know, Dana White has a remarkable array of opportunities before her, including company-owned hair salons, franchised salons, salons on military bases, hair products, and POS software. But especially since the pandemic, she has struggled to get traction. This week, in episode 111, special guest Ami Kassar, an expert in small business finance, guides Dana through a discussion of how she might prioritize those opportunities and get them financed. Ami and Dana consider such questions as: What should she do first? Should she continue to pursue franchising, where she’s already sunk a lot of money? Or should she focus on opening company-owned salons at Fort Bragg and in Dallas? And should she be looking for an investor? If so, how important is it that she maintains control of the business? Or should she try for a bank loan? And if so, what kind of pitch is likely to impress a bank? As the conversation continues, a plan emerges.
This week, Gene Marks talks us through the State Small Business Credit Initiative, or SSBCI, which is a tad complicated but well worth figuring out. While the actual offerings vary by state, as the name suggests, there is $10 billion on the table in the form of grants, loans, and venture capital that could conceivably help almost any business. Plus: the dangers of hitting customers with fine-print fees and surcharges, an assessment of New York City’s efforts to eliminate onerous regulations, and Gene makes the case for employee ownership—while explaining why he would never, ever consider an ESOP for his own business!
This week, in episode 110, Kelly Allan—a consultant who specializes in sharing the principles espoused by the late management guru W. Edwards Deming—returns to the podcast for a conversation with Paul Downs, Jay Goltz, and Laura Zander. After World War II, you may recall, Deming was sent to Japan, where he was largely credited with resuscitating the devastated economy. He of course went on to become tremendously influential here, too. And if you read his books or scan his “14 points” for management, it’s clear that many of his lessons are now widely accepted. But not all of them. For example, he encouraged business leaders not to set production quotas, not to hold people accountable—at least not without first holding the process accountable—and not to address employee performance and pay in the same conversation. Some of these issues came up in an episode that Paul, Jay, and Laura taped in December, which is why we decided to invite Kelly, who is chairman of the Advisory Council of the W. Edwards Deming Institute and has his own management consulting business, to join us. The goal was to see if we could figure out what Deming would tell Paul, Jay, and Laura, and whether the three owners would be open to his suggestions. Spoiler alert: Paul’s not really buying it.
“I see it, and I feel it,” Liz Picarazzi tells Shawn Busse and Jay Goltz this week, in episode 109, a conversation about the looming recession many are predicting. But Liz is not hunkering down. In fact, she has launched an ambitious marketing campaign that relies not on Google AdWords but on Google Alerts. She’s also taking some advice from Carey Smith, the founder of Big Ass Fans, that she didn’t want to hear when it was first offered. Plus: How some owners trap themselves in miserable businesses. And Shawn, Jay, and Liz suggest regulations that need to die—with Jay going off on the way businesses are compelled to pay for unemployment insurance.
This week, Lou Mosca, COO of American Management Services, which works with small businesses all around the country, talks about why hiring—and not recession or inflation—remains his clients’ biggest concern and what he and his clients are still learning about recruiting. Plus: Lou sees banks overreacting and warns about the dangers of online lending.
This week, in episode 108, Jay Goltz and Dana White talk about their employee handbooks. Do they take them seriously? Or is it just boilerplate? Has anything changed since the pandemic? Is the handbook the place to remind employees that they are hired at will and can be fired at any time with or without a reason? Are there issues that should not be addressed in the handbook? When was the last time they updated it? When was the last time they read it? “Me, personally?” responded Jay. “Actually picked it up and read it?” Yes, Jay, that’s the question. “Years.”
This week, Gene Marks tells Loren Feldman why he thinks investing in small business marketing is a lot like going to Vegas or Atlantic City—especially if you don’t have good data. But, he says, there are things you can do to improve your odds. Gene and Loren also discuss why Gene is rethinking the CRM systems he recommends, why business travel is coming back stronger than many expected, and why we’re experiencing both a labor shortage and a wave of layoffs at the same time.
This week, in episode 107, Shawn Busse, Jay Goltz, and William Vanderbloemen discuss whether the old line about hiring slow and firing fast makes sense during a labor shortage. As William puts it, “What if you do have to hire fast? How do you do that? What if you do want to keep people even if you might have wanted to get rid of them before? How do you do that without ruining your culture?” Plus: How do you know it’s really time for someone to go? And what happens when employees share their salaries with each other? Anything good? And as we all binge watch the real life dramas about WeWork and Theranos, the question inevitably arises: Is it still okay to fake it until you make it? And if so, where do you draw the line?
This week, Loren Feldman and Gene Marks resume their weekly conversations about the most important stories affecting business owners, starting with why Gene was ahead of his time in taking his business remote and why he thinks it’s left his company dysfunctional. Plus: what should owners take from the latest strong jobs report? And how will businesses be affected if the Supreme Court does indeed overturn Roe v. Wade?
This week, in episode 106, we start with an update of how 21 Hats has been doing since its sale brought new resources and new ambitions (Spoiler alert: It’s not going great!). Then, Dana White tells Shawn Busse and Jay Goltz about the progress she’s made on multiple fronts: attempting to sell franchises to revive her struggling Midtown Detroit location, to open new salons at Fort Bragg and in Dallas, and to secure financing. The owners discuss Dana’s financing options—venture capital, private equity, bank loan—assessing, in Shawn’s words, their “degrees of evil.” Plus: Shawn explains how his views on remote work have been evolving, and Jay explains why he’s tired of being called a tyrant (even though no one’s actually called him that).
This week, in episode 105, Shawn Busse, Paul Downs, and Liz Picarazzi talk pricing, specifically how they use an anchor price—the first number they offer prospective customers. Do they anchor low to avoid scaring anyone away? Or do they anchor high to disqualify unlikely buyers and to make the actual sale price feel more comfortable? Plus: Liz explains the remarkable, dream-come-true, my-product-in-Times Square PR gift she just received. Of course, this is entrepreneurship, so even when dreams come true, there tend to be complications. Liz’s business is getting a wave of publicity at a time when her fabricator in Shanghai has been locked down for almost four weeks. She’s talking to domestic fabricators as well, but they, too, will be dependent on raw materials that have to come from China. “It’s a problem,” she tells us.
This week, in a special bonus episode, Marcus Sheridan talks about the revolutionary strategy that he used to save his pool-building business during the Great Recession and that he’s been sharing ever since. That strategy is to volunteer answers to the questions your customers always ask—especially the questions you’ve been taught not to answer, at least not until you absolutely have to, such as those about pricing and potential problems with your product or service and who your best competitors might be. In this conversation, Sheridan also explains how to implement a content marketing strategy, why he isn’t a big proponent of social media, and what most business owners get wrong about marketing.
This week, in episode 104, Laura Zander tells Shawn Busse and Jay Goltz about her eight-month roller coaster ride pursuing an acquisition. The deal would bring a new brand and profitable revenue at a reasonable price. To Laura, the creative challenge and opportunity are exciting—“really, really exciting”—but the financials are a concern. “Do I do this?” she asks. “Is it worth it?” And then there’s the broker, whose numbers don’t add up and who wants to collect his fee—including his piece of the earnout—immediately. Plus: Shawn explains how the rise of inexpensive design contractors forced his company to become a better business.
This week, in episode 103, Shawn Busse, Paul Downs, and Jay Goltz discuss their philosophies about taking money off the table vs. reinvesting it in the business. Of course, you can’t take money off the table unless there’s money on the table. Paul tells us that he once calculated his average earnings for his first 22 years in business and they came to about $11 an hour. But he now expects to make more money in the next five years than he did in the previous 35. We also talk about content marketing, direct mail, and trade shows. Plus: Was the Paycheck Protection Program, despite the billions of dollars in fraud, a success?
This week, in episode 102, Liz Picarazzi tells Jay Goltz that she’s pursuing multiple sales opportunities—and ponders what would happen if those opportunities actually came to fruition. Would her company, Citibin, be able to handle the additional volume? “In my fantasy world, where I am a lot,” Liz says, “I look at where this could go. And just like you, Jay, I go to, ‘How in the world would I produce all of these?’” Liz and Jay also talk about the pros and cons of pricing transparency: Do you volunteer your premium price up front? On your website even? Or do you wait until you’ve made your sales pitch and gotten your customer excited? Plus: we indulge a little further discussion on the merits of the 21 Hats brand.
This week, in episode 101, the tables are turned, as Loren Feldman announces the sale of 21 Hats and takes questions from Shawn Busse, Karen Clark Cole, and Jay Goltz. The buyer is Toby Scammell, founder of Womply, which provides software services to small businesses and helped more than a million of them obtain Paycheck Protection Program loans. Loren will continue as editor-in-chief, but as he explains, much of what this will mean for 21 Hats has yet to be determined—including, for example, whether the new entity will keep the 21 Hats name. Shawn, Karen, and Jay share their thoughts on that and also talk about how Karen solves problems for her big tech clients—and what smaller businesses can learn from her process. And Jay explains a change he’s making to his 401(k) plan that he believes will make it fairer for all of his employees.
This week, in episode 100, two years after the pandemic first hit, Shawn Busse, Jay Goltz, and Liz Picarazzi talk about what they’ve learned, what they’re doing differently, and whether their businesses have gotten weaker or stronger. Leading up to the pandemic, Shawn—still carrying scars from the Great Recession—did a series of workshops on how to prepare for the next recession. “And so in that regard,” he tells us, “we were really well prepared” for the pandemic. Plus: public companies are increasing prices aggressively and then bragging on earnings calls about the extra profits those increases are generating. Is there a lesson in this for privately-owned businesses? Also: why does Jay seem more invested in his picture frame business than in his home furnishings business?
This week, in episode 99, Shawn Busse, Paul Downs, and Jay Goltz talk about the tendency of many businesses to obsess about their logo, their website, and the need to drive more leads. To which Shawn suggests concentrating first on customer experience. And Jay agrees: “It's better business,” he says, “to make your customers happier than to keep trying to find new customers.” But Paul has his doubts: “You can have your internal house in order, as I do,” he says. “And you can have a great website, as I do. But it's not driving new business to us at the moment.” Plus: Shawn, Paul, and Jay react to recently publicized strategies to address the labor shortage, such as giving out raises more than once a year and encouraging new employees to take a vacation before they start work.
This week, in episode 98, Jay Goltz tells Liz Picarazzi and Laura Zander that he’s had a revelation about The Great Resignation. Yes, he’s lost some people, but not necessarily his best people. “It shook the tree out,” he says, which is why he thinks businesses should be careful right now about hiring too quickly. Meanwhile, Liz talks about her latest product, a bear-proof trash enclosure, and why introducing it has been challenging. And Laura tells us what happened with the salesman she tried to send around the country in a souped-up van. Plus: Is this a great time or a terrible time to be in business?
This week, in episode 97, Paul Downs talks about why furniture makers traditionally have not stamped their names prominently on their work—and why he’s rethinking that now. That change of heart is the direct result of Paul’s unlikely experience connecting two very different businesses: One a Mennonite company manned by master craftsmen, and the other a startup manned by tattooed hipsters with a mastery of Kickstarter. Not only has the resulting culture clash changed the way Paul thinks about his own business, it’s also the subject of a book he’s writing. In this conversation, Paul explains what he’s up to and also talks about how close his business came to failing, how he plans to double his revenue, why he’s thinking about trying TikTok, and how he feels about his son’s success in the alternative reality of venture-backed startups.
This week, in episode 96, Shawn Busse, Karen Clark Cole, and Jay Goltz compare notes on some of the many choices they’ve made building their businesses, such as the emphasis they’ve placed on growth, the risks they see in growing through acquisition, and—as Karen has recently experienced—the rewards of being acquired. They also discuss whether The Great Resignation, despite forcing companies to pay higher wages and work harder to find and keep talent, just might be a good thing for business owners. As Shawn says, “This puts more people into the marketplace looking for businesses where culture matters, where the owner has compassion and empathy, where families are valued, just on and on and on. And if you're that employer, you win.”
This week, Loren Feldman and Gene Marks talk about why he thinks inflation is pulling workers back into the workforce. Plus: Is it a big deal that Apple is going to let businesses take payment by iPhone? And Gene explains just how easy it can be to steal money from a company’s bank account—and what you can do to protect your business.
This week, in episode 95, Jay Goltz, Liz Picarazzi, and Dana White talk about the advantages and disadvantages of bringing in outside capital and expertise—something both Liz and Dana have considered. “I have a background in Russian literature and credit card marketing,” says Liz. “I'm now a manufacturer, so if I could have an outside investor who either brought that to the table or could help me with it, that would be really valuable.” But of course, there are trade-offs. We also talk about Dana’s looming franchise sales, why it’s so hard to hire lawyers and accountants, and whether there’s an opportunity for Jay in framing NFT art.
This week, Loren Feldman and Gene Marks talk about whether a four-day work week is a benefit small businesses can use to lure employees. Plus: Is your website ADA compliant? And what do you do if you get a complaint that it’s not? And Gene talks about why he prefers Florida’s response to the pandemic to Philadelphia’s, which he says is killing the city’s restaurants. But are Philadelphia’s restaurants suffering because they can’t seat the unvaccinated? Or is it because they can’t keep their customers and employees healthy?
This week, in episode 94, Shawn Busse, Paul Downs, and Jay Goltz talk about their evolving succession plans. There are lots of options—selling the business, turning it over to a family member, selling it to an employee stock ownership plan, holding a going-out-of-business sale, just walking away—and they all come with advantages and disadvantages. Shawn, Paul, and Jay take us through their current thinking and also tell us whether their businesses are prepared for the possibility that they could be incapacitated. Plus: Would any of them consider instituting a four-day work week? And we can report that this podcast now has its first B Corp. Who knows what a B Corp is?
This week, Loren Feldman talks to Lou Mosca, COO of American Management Services, about the growing trend of making salaries public—either because municipalities require it or because businesses choose it. Plus: if the economy is growing at its fastest pace in decades, why doesn’t it feel like it? And how should businesses plan? And a recent study found that more than half of the 2,000 workers surveyed had resignation letters already written. What does this suggest about The Great Resignation?
This week, in episode 93, Jay Goltz, Liz Picarazzi, and William Vanderbloemen talk about sales, specifically the transition most founders have to make from handling sales themselves to building a sales team. Jay, Liz, and William also discuss the value of going to trade shows, the pros and cons of compensating salespeople based on commission, and the differences between inside sales and outside sales. “The kind of person,” Jay says, “who can go out there and cold call all day long and get the door slammed in their face—it's very hard to find, very hard to keep, very hard to train, very hard to control. And that’s been my biggest challenge in business, without any doubt.”
This week, Loren Feldman talks to John Arensmeyer, founder and CEO of Small Business Majority, about what most concerns the businesses in his group and how they view their prospects. Plus: what are smaller businesses doing now that the Supreme Court has blocked the vax-or-test mandate? Is there a possibility of more funds being allocated to the Restaurant Revitalization Fund? And what are the chances of legislation passing that would curb anti-competitive practices on Big Tech platforms? And is it really the case that these proposals have bipartisan support?
For many, knitting may still conjure an image of a grandmother in a rocking chair, her cats sleeping and her doilies taking shape. In recent years, however, the quiet industry of tiny neighborhood yarn shops scattered across the U.S. has become an unlikely cultural battleground. It’s been divided by charges of racism and cultural appropriation that have erupted in a series of social media firestorms, prompting some owners to close, sell, or rebrand their businesses. It may seem surprising that such a quiet pursuit could produce so much conflict, but it’s really not all that different from the fissures afflicting the country as a whole. In this bonus episode of the 21 Hats Podcast, we meet three women who were not content to stick to their knitting: Adella Colvin, whose business, LolaBean Yarn Co., is a prominent independent dyer based in Grovetown, Ga.; Gaye (a.k.a. GG) Glasspie, a leading yarn industry influencer whose signature color is orange and who is based in Clifton, New Jersey; and Felicia Eve, who owns String Thing Studio in Brooklyn, N.Y., which is one of the few Black-owned yarn shops in the country.
This week, in episode 92, we introduce another new member of the 21 Hats Podcast team, Liz Picarazzi, who talks Shawn Busse and Paul Downs through a series of challenges she’s faced at her business, Citibin. Among those challenges: why she outsourced her manufacturing to China, why she’s trying to bring it back, why she’s struggling to find an American fabricator that wants her business, why she thinks she wasted all of the money she spent last year on digital marketing, how she managed to double sales anyway, and where she found the right person to handle the aspects of running Citibin that she doesn’t think she’s good at.
This week, Loren Feldman and Gene Marks talk about how Hormel is somehow selling more Spam than ever. Plus: What will small businesses do now that there’s no vax-and-test mandate? Why Buy Now Pay Later is a good deal for small retailers (but potentially risky for their customers). And why you shouldn’t use your customer relations platform for email marketing—even though CRM providers say you can.
This week, in episode 91, we introduce a new member of the 21 Hats Podcast team, Shawn Busse, who tells Jay Goltz and Laura Zander about an intriguing challenge he faces. Twenty-two years ago, Shawn co-founded a marketing firm called Kinesis, but now he’s trying to convince clients that it takes more than just marketing. Sometimes, it’s not enough just to drive more leads. Sometimes, you have to step back and take a deeper look at your business, which not every client is ready to do. In fact, it took Shawn 10 years (and the Great Recession) to do it with his own business.
This week, Gene Marks tells Loren Feldman that he expects blockchain technology to spawn an explosion of digital transactions and a whole new economy. Does this mean business owners need to understand what a non-fungible token is? And would you buy an NFT of this podcast episode? Plus: tips for inflation-proofing your business. And is the Qualified Small Business Stock exemption a ridiculous loophole or a boon to small businesses?
This week, in a special bonus episode, we talk to Steve Krull and Dan Golden, co-founders of Be Found Online, a digital marketing agency based in Chicago. In the second quarter of 2020, as COVID hit and their clients stopped advertising, Krull and Golden watched helplessly as their agency lost 40 percent of its revenue. And then things got much worse: By the end of the year, both of their wives would be diagnosed with cancer. This is a conversation about how Krull and Golden have coped with matters big and small, personal and professional, throughout an experience they compare to being in a knife fight in the middle of a forest fire.
This week, in episode 90, we have a special guest, Fred Warmbier, owner of a metal-finishing business he founded in Cincinnati in 1998. About 10 years ago, Warmbier was ready to walk away from that business. “It just never seemed like I could have the type of business that I wanted,” he says, “where things worked properly and our employees were happy and our customers were happy.”
That changed when he discovered the Deming Management Method through a consultant, Kelly Allan, who helped him tame the chaos. Where does one start with Deming? “You start,” says Allan, who is chairman of the Advisory Council of The W. Edwards Deming Institute, “where the pain is.” As it happens, and as he discusses in this conversation, Fred Warmbier has experienced more than his share of pain.
This week, in episode 89, our last episode of 2021, we take a look back at the conversations we’ve had this year about the rewards and responsibilities of business ownership, including what it’s like to sell your business, to fire an employee, to risk your own home in order to get financing, to have to make a bet-the-company decision, and to deal with mental health issues, even thoughts of suicide. In this bonus episode, we highlight some of our happiest, smartest, funniest, and most difficult exchanges from the past year.
This week, Loren Feldman and Gene Marks talk about the arrival of omicron. With holiday parties getting canceled, sporting events getting canceled, offices either closing or postponing plans to reopen, it’s starting to feel a lot like—well, not Christmas, but more like March of 2020. Are businesses in for another rough patch? Or is that just COVID hysteria? Plus: Gene admits he likes ABBA.
This week, in episode 88, Jay Goltz and William Vanderbloemen talk about what it takes—in the throes of an unprecedented labor shortage—to hold on to your best people, the ones whose departures might send you looking for a trash can. They also discuss whether “hire slow” still works, whether it’s a good idea to rehire a former employee, whether it’s still possible to do a meaningful reference check, how to use 360 reviews and personality tests, and finally, whether Jay and William would be ready to sell their business if someone were to come along and offer them twice what they think it’s worth.
This week, Loren Feldman and Gene Marks talk about how some 20 states are giving business owners a special workaround that helps them evade the federal cap on state and local taxes. If you live in one of these states and have a pass-through corporate structure, it could be worth a lot of money. They also talk about reports that businesses are budgeting to give their employees big raises next year and why industrial space in some places is now worth more than office space. Plus: the latest Consumer Price Index inflation report is not looking very transitory.
This week, in episode 87, Paul Downs, Dana White, and Laura Zander talk about the lessons they’ll take from 2021 and what they’re hoping to accomplish in 2022. Paul thinks he’s found an alternative sales channel that will lessen his dependency on Google. Laura, who built Jimmy Beans Wool on ecommerce, is planning a renewed emphasis on brick-and-mortar retail. And Dana White is working on building the team that will help her pursue her remarkable opportunities with franchising and the military. Plus, we talk about how comfortable the owners feel showing up at work in a brand new car.
This week, Loren Feldman and Gene Marks talk about how businesses that engage in digital marketing are adjusting to the new rules that make it harder to track customers. They also discuss how businesses are replacing employees with chatbots and what businesses should do while the vaccine mandate battle plays out in court. Plus: the SBA has $100 billion in disaster relief funds that are about to expire and it’s not too late to apply. What you need to know.
This week, in episode 86, instead of a conversation with our regulars, we talk to two people who walked away from promising careers to buy blue collar businesses. Long before search funds and sweaty startups became all the rage, Bob Schwartz left a Wall Street investment banking career to buy a chain of laundromats, SuperSuds, which operates in Delaware, Maryland, Pennsylvania, and Virginia. More recently, Mills Snell left a prominent private equity firm to buy a roofing contractor, Aqua Seal Manufacturing and Roofing, which is based in Columbia, South Carolina. In this conversation, Schwartz and Snell talk about what they were thinking, what they learned about buying a business, what they’ve learned about operating a business, and whether they’re looking for an exit.
This week, in episode 85, Paul Downs, Jay Goltz, and Laura Zander talk about the bonuses they plan to pay this year—and how their bonus plans and philosophies have evolved over time: Are the payments a reward for company performance? Are they a reward for personal performance? Are they supposed to motivate? Or are they just a thank you? Then the owners talk management, a discussion inspired by last week’s episode with Dana White about navigating the space between being a pushover and being a jerk. Plus: Are 360 reviews good management or are they kind of creepy?
This week, Loren Feldman and Gene Marks talk about why robot sales are setting records and how even small businesses are taking advantage of the opportunity. They also talk about the inflation spike and why electric vehicles will help—at least over the long-term. Plus: the government takes action on ransomware, and a fresh approach to paid time off.
This week, in episode 84, Dana White takes us along for the ride, sharing the remarkable opportunities and the daunting challenges she’s confronting simultaneously. In a one-on-one conversation, we catch Dana at an emotional moment. After a triumphant trip to Germany, where she expects to open salons on multiple military bases, she’s just returned to Detroit—only to learn that the team she’s counting on is showing serious cracks. Even as she’s signing contracts with the military, getting ready to roll out her franchising plan, and courting newfound investor interest in funding the development of her salon management software, those cracks have shaken Dana and left her questioning her approach as a CEO. Ultimately, she talks about those moments many entrepreneurs experience in the cold of night, when things aren’t going well, and they realize this is all on them. In those moments, Dana confesses, “I’m scared. And I feel alone.”
This week, Loren Feldman and Gene Marks talk about an entrepreneur who may have cracked the code on TikTok by simply telling the story of her business the way she would tell it to a friend—although Gene’s not really buying it. They also talk about the Biden administration’s vaccine mandate now that the rules have been released, some options for businesses trying to figure out health insurance, and whether—as the Wall Street Journal reported—entrepreneurs really are happier than other people.
This week, in episode 83, Paul Downs tells Jay Goltz and Laura Zander why he’s come to view Google as the Volcano God. He’s not sure what it will take to keep the Volcano God happy, but he’s obsessed with doing everything he can, because the consequences of failing would be so great. We also talk about Paul’s content marketing strategy, the pricing lessons that emerged from our recent attempt to monetize 21 Hats, and why Laura—even in the midst of the labor shortage—now has a waiting list of people hoping to work at her yarn manufacturer in Texas.
This week, Loren Feldman talks to John Arensmeyer, founder and CEO of Small Business Majority, an advocacy group for entrepreneurs about the seemingly endless negotiations in the senate over what could be the Biden administration’s most important piece of legislation. What’s in the bill that would help business owners? Is there anything that would hurt? Is there anything not in the current version that should be? And will this ever end?
Several weeks ago, we had a great conversation about how Jay Goltz, Diana Lee, and Dana White track their financials. It was so good that, this week, in episode 82, we decided to put similar questions to Paul Downs and Laura Zander. “It's funny, I was listening to that episode,” Laura says, “and Diana said she's a freak about the numbers. I'm like, ‘God, does that make me a superfreak?’” Laura walks us through how her labor costs can affect what types of yarn she carries, Paul suggests a quick-and-easy ratio that can signal when a business is in trouble, and Jay explains how an hourly performance indicator that he began tracking 30 years ago transformed his business. Plus: Laura tells us how she got a bank loan that’s almost three times the size of the one she couldn’t get last year.
Every Monday, Loren Feldman and Gene Marks discuss what they learned the previous week that can prepare us for the coming week. We’ve all heard the expression “Fake it until you make it.” But how much faking can a business get away with before it makes it? Plus, Gene has common sense suggestions that can help business owners cope with both the supply chain mess and the labor shortage. And we also talk about where owners can turn when they feel they need a sounding board, and it doesn’t feel right to talk with employees, friends, or significant others.
This week, in episode 81, we have a celebration. As many of you will recall, when we started this podcast, Karen Clark Cole was coming off months of failed negotiations with a potential investor in Blink, the business she co-founded. Those months she spent focused on the investor took a toll on both Blink and on Karen, who subsequently took a mental health sabbatical. But, as Karen tells Jay Goltz and William Vanderbloemen, she came back, refocused, and has just sold Blink for $94 million in cash. As you might imagine, we had some questions for Karen, including: Will she stay? How many employees knew what was going on? Was there a bidding war? Is there an earnout? What was it like to wake up one morning knowing that she had taken all of her financial risk off the table? And is she ready to report to a boss?
Every Monday, Loren Feldman and Gene Marks discuss issues confronting business owners. This week, Gene makes the case for Facebook being good – at least for small businesses. We also talk about how even now—amidst all of the supply-chain snafus—businesses should be thinking about going global. Plus: is the Great Resignation headed for The Great Boomerang? And is it really time to take TikTok seriously?
This week, in episode 80, we talk about open-book management, which its proponents call the only sensible way to run a company. To test that theory, we bring together three skeptics and three believers to discuss what it really means for owners to open their books: Do employees know what the boss makes? Do they flee when the numbers turn red? Do they expect to have a say in big decisions? What emerges is an intimate look at how six smart business owners run their businesses.
Every Monday, Loren Feldman and Gene Marks discuss the issues business owners should be monitoring. This week, we talk about how car dealers are profiting despite the chip shortage, the dangers of depending on a platform like Facebook, a possible CRM game-changer, and the many questions that remain to be answered about President Biden’s vaccine mandate. For example, are businesses subject to the mandate if they have 100 employees but the employees all work from home?
This week, in episode 79, we go one-on-one with William Vanderbloemen. We start off talking about how he saw The Great Resignation coming and what he thinks are the keys to coping with it. Then we step back, and—with the help of many questions suggested by listeners—we discuss his conversion from pastor to CEO, what happened to his company culture when everyone went remote, and why he still reads every single email he gets—even when he’s off on a seven-week sabbatical. Plus: how he hit upon his unconventional social media strategy and his suggestions if you’re looking for a VP of marketing. (Suggestion No. 1: Try not to lose the one you have.)
Every Monday, Loren Feldman and Gene Marks discuss the issues business owners should be monitoring. This week, Gene explains why he thinks inflation and rising interest rates are going to end the recent surge in startups. Plus: Why raising prices is such a challenge for business owners—even when everyone is doing it. And what are we to make of a third straight month of falling consumer confidence? Are other metrics flashing warning signs as well?
This week, on episode 78, Jay Goltz, Diana Lee, and Dana White talk about how they manage their financials—what reports they get, what KPIs they track, and how they make sure the sales team isn’t going rogue. We also learn of a new wrinkle in Dana’s growth plan. She’s concluded that—along with rolling out franchises and installing hair salons on military bases from Texas to Germany to Okinawa—she also needs to create her own software platform to manage her salons. “Cha-ching,” responds Jay. Plus: Diana explains how the new digital marketing privacy rules hamstring small businesses—and what they can do about it.
Every Monday, Loren Feldman and Gene Marks discuss the issues business owners should be monitoring. This week, Gene explains why Intuit’s purchase of Mailchimp is going to lead to you stop sending out your boring monthly newsletter. Plus: Are you still screening job candidates for drugs? Couldn’t the public companies that got PPP money have at least paid it back? And how technology is improving performance reviews.
This week, in episode 77, Jay Goltz and Diana Lee discuss the dangers of mixing entrepreneurship and parenting. Years ago, when Chris Rock was asked in an interview about his relationship with his children, he responded, “My kids are rich. I have nothing in common with them.” Obviously, that’s an extreme example, played for laughs by a comedian, but you don’t have to be a celebrity to wonder about the differences between your upbringing and your kids’ upbringing. As it happens, Jay and Diana were both raised in family businesses, but they offer contrasting approaches to the challenges of raising a family and building a business at the same time. Plus: we also talk about what the upheaval in the auto industry means for Diana, how to think about the president’s vaccine mandate, and whether Jay has resolved his crazy double-billing problem with AT&T.
Every Monday, Loren Feldman and Gene Marks discuss the issues business owners should be monitoring. This week, Gene explains why he’s changed his mind about the president’s vaccine mandate. Plus: how smaller businesses can compete with Amazon’s $3,000 signing bonus—and get the government to pay for it. How some restaurants take advantage of their tipped employees. And are we finally done with business cards?
This week, in episode 76, Stephanie Stuckey talks about how she’s been winning her biggest retail accounts for Stuckey’s candies without a sales pitch. She also explains her latest manufacturing snafu, which she calls, “the case of the squishy pecan log rolls.” Laura Zander, meanwhile, tells us about the supply chain challenges she’s faced getting products from China, Vietnam, and South Africa. Plus, she talks us through how her latest price increases have resulted in a doubling of orders.
Every Monday, Loren Feldman and Gene Marks discuss the issues business owners should be monitoring. This week: the president’s vaccine mandate, the expanded EIDL, mitigating inflation, preventing ransomware attacks, and getting creativity from a remote workforce.
This week, Karen Clark Cole, Paul Downs, and William Vanderbloemen start with a discussion of how 21 Hats might finally take the plunge into monetization. We also discuss Karen’s decision to forgo less-profitable revenue, William’s grand experiment of unplugging for seven weeks, and Paul’s attempt to balance personal and company responsibilities. Plus, we consider the impact of The Great Resignation, and we look for lessons to take from last week’s discussion about mental health.
Because our core group of business owners has been talking to each other pretty much every week since before the pandemic, we’ve gotten to know each other. We’ve come to trust each other. And as a result, our conversations sometimes take unexpected turns. This week, our conversation takes an unexpectedly dark turn. We start out talking about Laura Zander’s efforts to manage personnel conflicts and Dana White’s visits to potential salon sites on military bases and Jay Goltz’s bizarre battle with his phone company, and we think we know what we’re talking about. But we keep talking until we realize that some of the issues we are discussing are more complicated and more painful than we’d understood, as is often the case with matters of mental health. You should know this conversation contains frank discussion of depression and suicide. For listeners, this may be surprising—not because anyone would think that entrepreneurs are immune to the afflictions that plague us all, but because there aren’t many public forums where people confront those afflictions openly and genuinely and in real time. For us, this conversation was a strong reminder that we often don’t really know what others are experiencing, whether they be friends, colleagues, or family.
This week, we have a very special episode. It’s the dog days of August, and the only regular available was Jay Goltz. So we reached out to a bunch of loyal listeners who we happen to know have listened to every episode of this podcast, and we asked them if there was more they wanted to know about Jay—or if they’d heard enough. It turned out, they had some great questions, including: What he thought of Dana’s “Jay” iImpression? What exactly he does all day (turns out, he’s not sure either)? How he learned to delegate? How he knows when it’s time to fire someone? And which of the other 21 Hats Podcast businesses he’d be inclined to invest in?
This week, Paul Downs makes two seemingly contradictory points: One is that his business is on track to have its best year ever. The other is that he expects to claim another huge government subsidy, courtesy of the recently enhanced Employee Retention Tax Credit. As Paul says, if you don’t know about the ERTC or if you don’t know that its requirements have been relaxed, you probably should check it out. Meanwhile, Jay Goltz tells us what happened when three employees found out what the others were being paid, and Dana White feels a little deflated after talking to an investment banker. Plus: Paul shares his new strategy for coping with the labor shortage.
This week, we delve into some specific hiring situations, including Jay Goltz telling Diana Lee and Dana White that he thought he had two terrific candidates to replace his retiring chief financial officer. And then, after conversations with each of them, Jay had no candidates, which led us to some interesting questions: Has there been a more challenging time to hire for cultural fit? How risky is it for a smaller business to hire a candidate accustomed to working at larger businesses? And what does hiring intentionally for diversity mean when your staff is almost entirely African American? Plus: Dana gives us an update on her potential deal with the military and Diana explains how she markets her marketing agency.
This week, Laura Zander, Diana Lee, and Dana White all share big news. Laura tells us that she and her husband/co-founder Doug put in a bid to buy a building for their business in Reno—and she’s not sure how she feels about the fact that their offer was accepted. Diana explains why she’s decided to pay a fortune to take over space vacated by glitzy magazine company Conde Nast in Manhattan’s Freedom Tower, a move that required her to put down a $2 million security deposit. And Dana tells us that she’s had preliminary conversations about opening Paralee Boyd salons on U.S. military bases around the world, which prompted Diana to encourage Dana to start vetting investment banking firms: “I'd be like, ‘Here's the contract with the Army. Give me the money so I can scale this out.’”
This week, we introduce a new regular on the 21 Hats Podcast team. Her name is Diana Lee, and she’s the founder of a digital marketing agency. In a conversation with Jay Goltz and Stephanie Stuckey, Diana explains how she got her business off the ground by helping car dealers target diverse communities within their markets, how she bootstrapped her business by convincing those car dealers to prepay 50-percent upfront, and how her first attempt at building a software platform ended with her spending $1 million on a platform that no one wanted to use.
When Dana White chose a name for her business, she decided she wanted a name that had meaning—both for her and for the women she hoped to reach. When Laura Zander picked a name for her business, she thought she was going to be selling coffee. And when Jay Goltz chose a name for his business, he very strategically chose the perfect name to rank well in—wait for it—the Yellow Pages. This week, Dana, Laura, and Jay talk about what they consider the most important decisions they made in building their businesses—including why Dana closed her most profitable location, why it took Laura 15 years to find an operations person, and what Jay figured out about employees who struggle to grow with the business.
This week, we talk about how much of success is making the right decisions. How much is being in the right place at the right time? And how much is just luck? “I think that's the thing nobody wants to talk about,” Paul Downs tells us, “because it implies that there's a lot to success that is out of the control of the entrepreneur, and we're much more attracted as human beings to stories of people who have agency and are like, ‘Oh, there's a problem. I did this, and I won.’ That's what we like to hear.” So yeah, there’s always luck involved. But there are always forks in the road, and someone has to decide which way to go. This week we hear how a few of those key decisions played out.
This week, we take another crack at some questions that don’t have definitive answers: Should business owners outsource their marketing or bring it in house? Either way, how do you know you’re picking the right agency or the right person? Is it possible to get someone great for what smaller businesses can afford to pay? Paul Downs tells us what happened when he hired a firm to audit his website. Dana White tells us why she dumped the agency she’d retained for $50,000. And Jay Goltz sums it up: When it comes to the mechanics of marketing, he says, “We’re all in the dark.” Plus: Dana gives a franchising update and Jay starts his own business group.
Once again this week, our business owners discuss things business owners don’t often talk about in public. Laura Zander says she feels guilty about taking vacations, about making more money than her employees, and about knowing that her husband is closer to their son than she is. Paul Downs says he recently reviewed 29 years of P&Ls and was reminded that he lost money in 18 of those years. He also explains why he routinely tells his employees (and us) precisely how much money he takes out of his business. Jay Goltz, meanwhile, says he’s now embarrassed to be called a CEO and acknowledges that he’s thought maybe he should have worked 20 percent less while building his business, but isn’t sure if that would have resulted in 20 percent less revenue or perhaps 100 percent less revenue.
This week, Stephanie Stuckey tells Jay Goltz and Dana White about moving closer to the candy factory she recently bought to get a better feel for the people, the operation, and the challenges. Right now, those challenges include recruiting enough employees, absorbing increased supplier prices, and figuring out how much she should raise her own prices: “We can only give up so much of our margin, right?” she tells us. To which Jay responds, “Why give up any?” Plus: we talk about competing for labor with Amazon, whether to require employees to get vaccinated, how to manage legal fees, and whether Dana’s feelings of FUD have eased.
This week, Dana White tells Paul Downs and Jay Goltz why she’s experiencing FUD—fear, uncertainty, and doubt—over whether she’s really ready to sell franchises in Paralee Boyd. She’s concerned because her hair salon is having some issues with customer service. On the other hand, her head of operations, Ashley, is telling her, “If you wait to expand your business until every customer is happy and until everything is perfect, you will stay at one location for the next 50 years.” Plus, Paul resolves his cybercrime, and we find out whether Paul, Jay, and Dana have done anything to prepare for a ransomware attack. It turns out one of them has.
This week, Paul Downs, Jay Goltz, and Dana White talk about confronting inflation, raising their prices, what businesses owe their employees, and the venture-backed competitor who’s opening a store in Jay’s backyard. Among the questions we discuss are: Would you take back a rebound employee? Are unemployment payments the main reason owners are struggling to fill jobs? Is there anything wrong with taking business from another business? How many companies are truly disruptive? And do owners take all of the risk? Or are there risks for employees, too?
Is your office open? Is everyone coming back? Or are you going hybrid? Is everyone getting vaccinated? Are you offering them incentives to get vaccinated? When do the masks come off? Are you having a problem filling jobs? Have you had to increase what you pay? Paul Downs tells us, “The people who really seem to want the job and are enthusiastic about it don't have the skill-set. And the people with the skill-set don't seem to actually care about completing the process. So we did hire one guy who started a week ago Monday, and he quit three hours later.” This week, Paul, Stephanie Stuckey, and William Vanderbloemen compare notes on what they’re experiencing as we all search for that new normal.
This week, Jay Goltz, William Vanderbloemen, and Dana White discuss whether Jason Fried, the embattled co-founder and CEO of Basecamp, has displayed courageous leadership or lost his you-know-what. Widely admired for building a tech company that didn’t take venture capital and didn’t pursue growth for growth’s sake, Fried is co-author of a book called It Doesn’t Have to Be Crazy at Work. All of which made it somewhat disorienting last week when things did indeed get crazy at Basecamp. It started when Fried published a blog post decreeing there would be no further discussion of political issues at the company, but it soon became clear that this was not just about coworkers arguing Trump vs. Biden. And by Friday, at least a third of the company’s 57 employees had resigned. In this episode, we go searching for lessons.
This week’s conversation with Paul Downs, Jay Goltz, and William Vanderbloemen was supposed to be about how the pandemic has affected sales strategies—and for a while it was. But it seemed Paul, Jay, and William really wanted to talk public relations. They talked about how to get PR and how to assess the results. They compared the merits of public relations to those of advertising. And they discussed whether you need to hire a firm or whether you can do it yourself. One concern all three shared is the cost of hiring a public relations person. As Jay pointed out, “You hire an accountant, you're going to get some accounting. You hire a lawyer, they’ll do some legal work. PR's one of the few things you can pay money for and get absolutely nothing.”
In this week’s conversation with Karen Clark Cole, Jay Goltz, and Stephanie Stuckey, we once again unearth more questions than answers—mostly because there are rarely one-size-fits-all answers to the questions we discuss. This week, those questions include: Can you be friends with your employees? Can you work with your family? How are you coping with price increases in your supply chain? How do you handle shipping—especially given the example set by Amazon? Are refrigerated trucks really called “reefer” trucks? And what happens when employees question whether you should be doing business with a particular person or company? Plus: Jay turns 65 without a succession plan.
This week, Dana White informs Jay Goltz and Stephanie Stuckey that she has begun the process of franchising her hair salons across the country, and perhaps the world. Why did she choose to franchise? As she explains, she does have concerns about controlling the culture in franchised locations, but she believes this is her best opportunity to grow. Interestingly, when Stephanie took over Stuckey’s in 2019, she bought a franchise business that she says had lost control of its franchisees, which is why she’s now moving in the opposite direction. Plus: Stephanie shares a debate that is raging within her company: Should she price her pecan log rolls for the convenience stores she’s selling them to now or for the more upscale outlets she hopes to attract? And Jay gives us an update on that idea for a new business he told us about just two weeks ago. (Spoiler alert: This is Jay Goltz we’re talking about.)
This week with Paul Downs, William Vanderbloemen, and Laura Zander, the talk leaps from one plague to another—floods, power outages, cyber crime, employee churn, supplier price hikes, and vanished shipping containers—not to mention the actual plague. For Laura, whose wholesale yarn business keeps falling further behind on its orders, these events have necessitated a series of difficult conversations with customers: “They can't get mad about the pandemic,” she tells us. “And they're not going to get mad about the fact that we're moving. And they're not going to get mad about the fact that there's a deep freeze. But at some point, they're going to get tired, whether it's consciously or subconsciously. It's exhausting.” To which she adds, “but if the locusts hit, I don't know how much more of this people can take.” Plus, a friendly discussion about whether raising your prices makes you a jerk. (Spoiler alert: It does not.)
This week, Jay Goltz tells Dana White and Laura Zander why he can’t stop starting businesses. In recent years, for example, he’s considered buying other picture -frame shops, he’s bought a firehouse that he thought he might turn into an event space (or a dog kennel), and he’s fantasized about opening an ice cream shop. “I have a whole list of businesses I'm not starting,” says Jay, who has been down this road so many times he’s developed a five-point test for whether he should proceed. And now he’s got a new idea—an online art gallery—that he believes passes the test. “I think I’m going to do it,” he says. Plus: Dana has a new business, too. And Laura assesses the damage done to the yarn industry by two venture-backed rivals.
This week, Stephanie Stuckey tells Paul Downs and Jay Goltz about seeking the guidance and perspective that a board of directors could bring to Stuckey’s. But does a business have to be a certain size to warrant having a board? How do you recruit board members? How should they be compensated? And is a peer group, like Vistage, a better alternative? Plus: Uncovering a $140,000 cyber crime. Coping with the nightmare of shipping furniture. And Jay tells us why, if you listen to either the artists or the accountants in your business, you’re likely to go broke.
Should Stephanie Stuckey sell pecans on Amazon? Should Laura Zander wholesale yarn to discounters? Should Jay Goltz’s businesses be active on Pinterest? (Assuming Jay knows what Pinterest is.) This week we cover those issues, plus whether the owners are ready for an economic boom and how Laura made the painful decision to fire several employees she inherited when she bought her wholesale yarn business in Texas. “You have to do it,” says Jay. “And it doesn't make you a bad person. It makes you a bad boss if you don't do it.”
This week, we talk about what we were thinking a year ago as the contours of this crisis began to emerge. It was this week that the W.H.O. declared a pandemic, the NBA suspended its season, and toilet paper started to disappear. It has all taken a toll. “This is where it gets tricky,” Jay Goltz tells us. “Just because everybody shows up every day and looks like they're happy-go-lucky, they're not. People have stresses in their life, whether it's their kids, whether it's their aging parents, whether it's their financial situation, whether it's their physical well-being—any of the above. This is just layered on top of whatever was going on in their life before.” Plus: Karen Clark Cole’s company goes to Mars, Dana White gets a smart question about expansion from a retailer in Canada, and Jay discovers that ESOP companies don’t have to pay federal income tax.
A year ago, Dana White was questioning whether her business could survive the pandemic. This week, she says she’s looking seriously at expanding to another city: “I'd like to make a decision by the end of March, and I'd like to be opening or in the process of opening by this fall. I'm waiting to see how the vaccine does.” Dana also talks about her experience with venture capitalists who seem to be telling her, “We’ll be happy to give you money—as soon as you don’t really need it.” Plus: Stephanie Stuckey explains her team’s recent three-hour debate: Should Stuckey’s be selling the road trip or the pecan? And Dana, Stephanie, and Jay Goltz discuss Clubhouse, the new social media platform. Is it just a time suck, or does it offer real value to business owners?
This week, Stephanie Stuckey tells Paul Downs and Jay Goltz, both of whom have manufacturing operations, about her decision to buy a manufacturing plant and bring production of Stuckey’s snacks in-house. We talk about her conflicted concerns about a minimum wage hike, what it takes to build a strong culture in a repetitive-task environment, why she paid above book value for the company she bought, and how she managed to finance the purchase of a business that is four times the size of Stuckey’s. She’s very happy with the SBA loan she got, but it was not an easy process: “I had to take out an additional life insurance policy and list the bank. I was just waiting for them to call me and tell me my firstborn son has to be collateral as well.”
This week, Karen, William, and Laura cover a lot of ground: For one thing, what do you do when the to-do list seems endless, you’re already working 24/7, and you just can’t get ahead? For another, what do you do when employees decide they want to work remotely from random parts of the country? Does that work? Is it a bureaucratic nightmare? Meanwhile, Laura is confronting several big, interrelated issues. Her co-founder and husband, Doug, is ready to step back from the business. That’s a little tricky because the company operates off a 19-year-old platform that Doug built, and only he knows how to make it work. They’ve been trying to hire tech people for Doug to train, but they’ve been through 15 people in 10 years—and they know they’re doing something wrong. Do they need to hire a recruiter? Is it time to junk Doug’s platform and go with Shopify? If they do that, will they forfeit 19 years of SEO value? All of which has left Laura feeling trapped. “That’s this cage that we’re in,” she tells us. “What the hell do you do?”
This week, Paul, Jay, and Dana give quick PPP updates—and then dive into a discussion of what a $15 federal minimum wage would mean for smaller businesses. Will it lift people out of poverty? Will it put businesses out of business? Will it hurt entry-level employees? “I'm listening to you, Jay,” Dana tells us, “and I'm thinking about the coffee shop owners I know who have to close.” To which Jay responds, “They say they have to close, but did they try raising their prices 5 percent first?” We also tackle a listener-submitted question about the best way to avoid unemployment claims, which can require forceful management. “There's no way around it,” Paul tells us. “You gotta be hard at some moments, as a boss. You just have to be.”
This week, William tells Karen and Dana that he’s cautiously optimistic about 2021 because his clients are cautiously optimistic and because he’s expecting lots of turnover as the pandemic recedes. William explains how he uses a “Frankenstein” customer relations system to track what his clients read on his website and to sense when those clients are getting ready to make a hire. The system then prompts the Vanderbloemen team to give the client a call. We also talk about why Karen is tired of being a best-kept secret and how Dana handles customers who have to be fired. Plus: there’s a new tax credit you should know about that William calls “pretty incredible” but that seems to be getting lost in the PPP shuffle.
This week, we introduce Stephanie Stuckey, a new regular on the podcast who tells Dana White and Laura Zander about the iconic road stop business her grandfather founded: when it peaked, what went wrong, why she bought it back, and how she plans to rejuvenate it. Along the way, we discuss whether small businesses should outsource their marketing, how hard it is to find an agency that really listens, and what it should cost to hire a marketing firm. Plus: Stephanie offers a tutorial on how to engage followers—and get free consulting—on LinkedIn.
This week, Paul Downs and Jay Goltz talk about their New Year’s resolutions. Here’s Paul’s: “My New Year's resolution is that we will be open on December 31st, 2021. And I don't know whether I'll have the same number of employees, but we will be open. I will be here.” And here’s Jay’s: “My New Year's resolution is: I'm not gonna do anything stupid this year. So far, so good.” Paul and Jay also talk about Paul’s disappearing backlog, each of their plans for PPP Round II, Jay’s efforts to lure one of his sons into his business, and—responding to a listener question—how they handle business and personal expenses. “I think we have to stop recording right here,” says Paul.
This week, responding to a question from a listener, Jay, Dana, and Laura talk about managing people. Jay offers a four-step plan that starts with making sure you’ve hired the right manager: “Anytime you ever hear anyone complaining about their employees, it's a bad manager.” Laura talks about coming to the realization that her staff is not where she thought it was—and how that’s playing into her recent anxiety attacks: “So now, I’ve got anxiety about my anxiety.” Plus: Dana’s getting married! And Loren wants to know how you know if you have a real business.
This week, in our final podcast taping of the year, Paul Downs, Jay Goltz, and William Vanderbloemen discussed the impact this year has had on their businesses and on themselves. William talked about the positive side of having to get back to a startup mentality: “It's definitely been a silver lining in the middle of a very dark cloud.” Paul talked about hoping he can offer his employees a good place to work for as long as possible: “I can give them probably another 10 years. And then beyond that, I don't know what will happen.” And Jay talked about the cash management mistake he made that could have been fatal: “If I wouldn't have gotten the PPP money, I don't know…”
This week, Paul Downs, William Vanderbloemen, and Laura Zander talk about William’s prediction that 2021 will be a year of employee turnover. His theory, which he says he’s already seeing evidence for, is that pent-up forces that were blocked by the pandemic this year will be unleashed in 2021—especially as vaccines arrive and the economy improves. His advice: Make sure your best people feel appreciated. Or, as he puts it: “Better to keep a good employee—even if it costs you more than you think it should—than to have to call me.” Plus: we establish that no one knows how to manage their PPP loan tax liability, and we discuss whether, when the time comes, businesses should require employees to get vaccinated.
This episode is dedicated to Ivy Garfield. Back in 1996, Jay Goltz had no real hiring process and the results to prove it. “My hiring success rate,” Jay tells us, “was probably, I don't know, 30 or 40 percent, which isn't much better than whoever walks in you hire.” And then he asked Ivy Garfield to take over his hiring. As Jay explains, Ivy brought an instinct, an understanding of how to assess people. “She profoundly changed my business,” he tells us. “She was here six years. Most of my key people she hired. They’re with me 25 years later.” Jay talks about the secret to Ivy’s success and why entrepreneurs like him tend to be terrible at hiring. Plus: Dana White talks about being disappointed by a mentor. And Jay and Loren offer an apology.
This week, starting with a conversation about crucial hires Dana White and Laura Zander have made recently—an operations manager for Dana, a salesperson for Laura—we found ourselves exploring some of the great unresolved debates of entrepreneurship. Which comes first when hiring: filling specific needs or finding places for good people? With sales people, do you motivate by paying commission or build a team by paying salary? And in finance, do you bootstrap to maintain control or raise capital to grow faster? Obviously, there’s no right answer for these questions, but Dana and Laura tell us what’s been working for them.
This week, Paul Downs, Jay Goltz, and William Vanderbloemen assess the damage of a stressful year. We started with the impact the year has had on the value of their businesses. Then we discussed whether they would be ready to sell their businesses if a generous offer were to come along. That prospect, Jay tells us, would likely cause him to do some soul-searching, but he would consider it skeptically. It seems to be a well accepted fact, he says, that most people who sell their business end up regretting it. Plus: as we head into budget season, we find out whether the three owners are planning to give raises. And in this week’s Morning Report News Quiz, we learn what happened to Inspiration, Imagination, and Fantasy.
For Jay Goltz, William Vanderbloemen, and Laura Zander, concerns about the pandemic loomed large this week as one of them had to self-isolate in his basement after being exposed to the virus. That fact helped surface a number of interesting questions: Are the three owners being careful enough? What should they tell employees who choose to travel over the holidays? Should employees who travel get paid if local rules require them to quarantine after they return? And if traveling employees do have to quarantine, will these businesses have enough staffers available in December and January to function? And then there was the question Laura demanded of Jay after Jay explained how exactly he was exposed to the virus: “Wait, no,” she said, “You didn't answer my question. Were you wearing a mask?”
And so, yes, Dana White was in fact the big winner at last week’s Detroit Demo Day, taking home the top prize of $200,000 for her hair salon business, Paralee Boyd, which specializes in serving women with thick and curly hair and which has an unusual walk-in-only business model. Of course, Dana now has some decisions to make: Does she want to take the money in the form of a zero-interest loan? Or does she want to take it in the form of a convertible note, which can convert to an equity stake in her company? And perhaps, more importantly, how exactly is she going to spend the money? As she tells Paul Downs and Jay Goltz in this conversation, she’s thinking about spending it on marketing, on opening another location, or on creating retail products for sale online or in her salons. What do you think Dana should do? Please email your thoughts to lfeldman@21hats.com, and we’ll share them on the podcast and in the Morning Report.
This has not been an easy year for Dana White, who has had to close one of her two hair salons and who has struggled, amid the pandemic, to keep the other one staffed. But this week she reveals to Karen Clark Cole and Paul Downs that she’s a finalist for a potentially game-changing pitch competition. “A $200,000 investment from Quicken Loans is a huge validator when you're looking to grow,” says Dana. “When you have first money in from Dan Gilbert, it bodes well for your company.” Dana also tells Karen and Paul that she’s just made her most important hire ever, an operations manager who had a compelling reason for wanting to join Dana. Plus: the Morning Report News Quiz.
This, to say the least, has been a challenging year. So this week, we’ve decided to bring you two inspirational success stories by revisiting one of our earliest podcast episodes. Way back in November of 2019, Karen Clark Cole and Loren Feldman attended EY’s Strategic Growth Forum in Palm Springs where we conducted a series of interviews with participants in EY’s Winning Women program. Two of those interviews were with women who started companies from scratch and sold them successfully—learning all sorts of lessons along the way.
In this week’s episode, the tables are turned. This week, it’s host Loren Feldman who fields questions and takes advice after he explains why the BusinessAdvantage TV Podcast will once again be The 21 Hats Podcast. “The bottom line is: I am now the proud owner of a pre-revenue startup that has a daily email newsletter that we've been giving away for free, plus this weekly podcast that we've been giving away for free, and the designs for an unbuilt website that we had hoped to one day charge subscription fees for. Any thoughts?”
In this week’s episode, Dana White, Laura Zander, and Jay Goltz talk about their real estate challenges. Dana decided to close one of her locations rather than keep dealing with an overly aggressive landlord. Laura, fearing her landlord was going to throw her out, decided to buy a building. But she hasn’t been able to close on the deal because, while she’s been to six banks, she has yet to find one that will fund the loan—even though she already has SBA approval for a loan. And Jay wants to take out a mortgage on a building he owns outright just to have some extra cash on hand, but he’s on his 10th bank. “You can’t get discouraged,” Jay tells Laura. To which Laura responds: “Come on, what do you mean, ‘You can't get discouraged?’ You see my face? It’s called discouragement.” Plus: the Morning Report News Quiz returns.
This week, six months into the crisis, Paul Downs, Jay Goltz, and William Vanderbloemen take inventory. What does the crisis mean for the future of their businesses? Has it changed them as leaders? Has it affected their relationships with their employees? And they come to some counter-intuitive conclusions. For one, William tells us that he suspects he will one day look back on the crisis and conclude it was the best thing that could have happened to his business. It’s been painful, he says, but, “in some ways, we needed a jolt, and this gave it to us.” Jay understands: “When things get really bad like this, we start paying attention to stuff that we should have been paying attention to before.” Plus: do the three owners have a plan for how their businesses would continue to operate if they were incapacitated by COVID?
This week, Karen Clark Cole, Paul Downs, and Jay Goltz talk about whether their businesses need another round of government support, whether in the age of COVID they monitor their employees’ behavior away from the office, and whether there are aspects of running a business they would like to be better at. One thing they say they are all good at is taking action when an employee has to be shown the door. As Jay tells us, “If we didn't figure out how to fire, we're not on this show, because we're out of business at this point.” Plus: Did Paul keep his promise to see if he could connect with someone at Google to discuss his AdWords campaign?
In this week’s conversation, Karen Clark Cole, Paul Downs, and Laura Zander talk about their approaches to digital marketing. After years of relying on Google AdWords as his only form of marketing, Paul tells us, he stopped his $12,000-a-month spend a few years ago—relying instead on organic traffic. What happened when he stopped? His sales actually went up. But now, with fewer people looking to buy high-end boardroom tables because of the crisis, he’s considering shifting tactics again: “I'm wondering whether I should sort of go on the offensive,” he says, “and try to increase my marketing in the face of these declines in sales, or whether nothing I do would make any difference at this point.” Plus: Is it better to manage your own digital marketing or to hire a specialist? Our panelists disagree.
In this week’s conversation with Paul Downs, William Vanderbloemen, and Laura Zander, Paul explains why he’s not planning to pivot his business—even as his sales collapse. Normally, Paul says, his most reliable customers are other business owners. When they call to ask about a custom boardroom table, he and his sales staff know they are likely to buy. Right now, though, in the midst of a pandemic that has changed the way people look at commercial space, they aren’t even calling. A lot of people have suggested that Paul pivot to manufacturing desks for home offices. So far, he’s resisted the idea. “To walk away from what we know,” he says, “and do something that we don't know and that others know very well, I just feel like it would be a huge mistake.” Paul, William, and Laura also talk about how the crisis has affected their own compensation.
For years, business owners complained about how tight the job market was and how hard it was to find good employees. Well, so much for that. Funny thing, though. In this week’s episode, William and Jay talk about how, in many ways, hiring has gotten even harder during the crisis. Part of it is having to rely more heavily on Zoom. And part of it is having to sift through the many people who are suddenly available to find the right person. “The most expensive hire you will ever make,” William tells us, “is hiring the wrong person. I mean, you can spend all the money you want on a search firm, and it’s still not as expensive as hiring the wrong person.”
In this conversation, Karen, Jay, and Dana discuss diversity in hiring and marketing. Dana talks about the challenge of getting white customers to come to a hair salon that is mostly Black. Karen talks about the challenge of persuading Black candidates to join a company that does not have a lot of Black employees: “So the question is not: are they out there? They're out there. I guarantee they're out there. The question is: do we need to spend more time, more energy, and be willing to be patient until we find a good pool of candidates?”
Paul Downs, Jay Goltz, and Dana White talk about how they would know if it was time to close their business, how long it takes to really grow up as a manager, what they’ve learned about managing—and occasionally firing—employees. “I think my staff hears me but eventually does what they want to do,” says Dana. “And that can be very draining because you wonder, ‘Well, why? I pay you. We’ve had training on it and talked about it.’” And Paul tells us that while he’s normally a pretty nice guy, he does have to put on his “Jay Goltz face” occasionally. “So what does that mean exactly?” asks Jay Goltz. “I’d like to understand.”
This week, we introduced a new member of the podcast team, Paul Downs, whose company, Paul Downs Cabinetmakers, makes custom conference tables. Paul wrote about how close his company came to failing in both The New York Times’ You’re the Boss blog and in his own book, "Boss Life: Surviving My Own Small Business." That was during the Great Recession. Unfortunately, Paul is once again finding it challenging to sell high-end conference tables during a crisis. “My game plan is to stick it out,” he told us in this episode. “I’m not going to shut the doors. And two years from now, I may be a smaller company, but I'm going to be around, and then we're going to ride this back up.”
In last week’s episode, we asked our panel of business owners this question: Would you be doing anything differently with your business if you knew for sure that a second shutdown order was coming? It seemed like a pretty straightforward question, but it triggered one of our guests, Jay Goltz, who called it a “stupid” question and encouraged the other panelists not to answer it. So this week, we decided to try again to see if we could better understand how Jay is processing these stressful times. And to some extent, we succeeded, and we did get a little further beneath the surface—although there’s still a part of Jay that seems to be in denial. But maybe that’s just what it takes to be a successful entrepreneur. As Jay likes to say, “There's a thin line between visionary and delusional, and I've certainly been on both sides of that.”
As the numbers of new coronavirus cases explode across the country, Karen Clark Cole, Jay Goltz, and Laura Zander talk about how they are trying to make plans for their businesses. The conversation heats up a bit as it becomes clear that one of our owners (Hi, Jay!) isn’t quite ready to confront the possibility that he might have to deal with another shutdown. By contrast, Laura tells us, “We're operating as if there is a shutdown. So, yeah, we're operating the same way we were two months ago.”
Jay Goltz, William Vanderbloemen, and Dana White—all of whom took Paycheck Protection Program loans—respond to an opinion piece that says “competent” business owners shouldn’t have had to go begging “shamelessly” for a government bailout, which got a particularly strong response from Jay: “I'm thinking of all of those entrepreneurs who are trying to run a business, trying to make happy customers—restaurants, hair salons trying to survive this whole thing, trying to take care of the emotional, the financial, and the physical needs… They're fighting a good fight, trying to stay in business so they can continue paying taxes, and he comes along and has to call us ‘shameless’ for taking money from the government.... Oh, we’re incompetent, because these people didn't have six months of savings stowed away?"
Karen Clark Cole, Jay Goltz, and Dana White discuss their pricing strategies and why raising prices can be such a challenge: Dana tells us she has often wondered, “If I raise my prices, is this the decision that's going to make me close my doors?” And Jay recalls a customer who came into his picture framing shop and told a sales consultant, “Wow, that's a lot more than the other place I've gone to.” “Really, why don't you go there?” “Well, they're out of business.” And that, Jay tells us, helps explain why there are far fewer frame shops than there used to be.
Karen Clark Cole, William Vanderbloemen, and especially Dana White have a painful, impassioned, uncomfortable conversation about trying to position their businesses and lead people in the aftermath of George Floyd’s murder and the ensuring protests. What do we tell customers? What do we tell employees? What do we tell black employees? Dana challenges us to take a stand—even if it’s uncomfortable—especially if it’s uncomfortable: “This is not about being comfortable. As business owners, you're either over there or you're over here.”
This week we focused on Laura’s struggle to get control of a Texas-based yarn supplier that she acquired late last year. She’s had issues with inventory, personnel, quality control, and then the general manager walked out, which has Laura feeling deflated knowing that some employees are talking about her and some just don’t like her: “I really struggle with that. Am I the only one who struggles with stuff like that?” Plus: Laura and Jay talk about seizing the opportunity when a competitor goes out of business.
Before the crisis hit, Jay, Dana, and William talked about what they thought the next recession might mean for their business and the benefits of starting a business during a recession: “What I've learned is, when things go bad and I lose $300,000 and I take out a second mortgage on my house, no one comes into my office and says, ‘Hey, boss, can I give you some money?’” Plus: Some making tough decisions on employee compensation.
In this week’s report from the front lines of the crisis, we talked about overcoming the fear of raising prices (during a pandemic!), deciding when is the time to tell employees they have to come back if they want their jobs, and finding opportunities amid the crisis disruption. But the focal point of the conversation was Dana White discussing her realization that she’s been more productive during the crisis, even with her hair salons shut down, than at any other time since she started her business seven years ago. “I have been emotionally drained for years,” she told us. “And because I've been emotionally drained, I have not grown my business.”
Karen, Jay, and Laura talk about dealing with questions they’ve never faced before: Is it safe to fly again? What do you do if you run out of inventory and can’t get more? How do you entice employees back into the office who’ve either been happy working from home or happy collecting enhanced unemployment? Do you offer hazard pay? And if so, how and when will you stop? “We're trying to stay in business, for God's sake,” says Jay Goltz. “We will have been shut down for two and a half months. And there's a point where I'm the only one who's gonna be losing money in this deal. At the end of the day, [my employees] are getting extra money from the government for unemployment. They're getting hazard pay. Everybody at the end of the year is going to have a banner year for income. And I'm going to lose hundreds and hundreds of thousands of dollars.”
Jay, Dana, and Laura talk about the process of reopening—the precautions, the risks, the consumers who might not show up, the dilemma of asking employees to accept less in pay than they were getting in unemployment, and the possibility of a second coronavirus wave that could bring a second shutdown: “I don't have the luxury of just saying, ‘Oh, I'll tell you what. Maybe we'll open in six weeks, eight weeks.’ I mean, there's some point where I'll be out of business.” Plus: Dana got her PPP and an EIDL.
Karen, Dana, and Laura share their experiences building businesses as women entrepreneurs: “It's like, ‘Well, you can tell me I can't do this, but it looks like I did.’” Plus: Has the legalization of recreational cannabis had an impact on your business?
Karen, William, and Dana talk about why some businesses got the Paycheck Protection Program loans and why some didn’t: “The independent grocers. The hair salons. The small restaurants. They didn't get the money,” says Dana. “I have a staff who are single mothers, single black mothers, who are hard-working and who didn't have the foundation to go to college and are doing what they can. I'm up every night trying to help them, and I need help helping them. And I'm not getting it.”
Jay, William, and Laura talk about the status of their CARES Act loans, and to everyone’s surprise (including his own), William reveals not only that his Paycheck Protection Program loan has been approved, but he’s already got the cash. Was it divine intervention? Plus: Jay offers up a stress test for businesses in crisis—five ways to assess whether your company is positioned to survive.
Jay, William, and Dana talk about their prospects for landing a Paycheck Protection Program loan, what they think business will be like when shelter-at-home ends, and why they decided to lay off people even though they expect to get forgivable loans: “The bottom line: we cut 40 percent of our payroll yesterday. My decision was, I would rather cut deeper, fewer times. So I'm going to do this once.” Plus: the daily routines of business owners stuck at home.
William, Dana, and Laura and their businesses are having very different coronavirus experiences. While Dana and William are expecting little in the way of revenue, Laura’s online yarn business is thriving. But they’re all facing challenges in managing their employees: “It's been amazing to see just how hard folks are working. Are they concerned about a layoff? I'm sure they are. I would be too.” Plus: finding ways to stay connected to customers even while the business is closed.
Karen, Jay, and Laura talk about painful layoffs, maintaining morale, and hunkering down during COVID-19: “We've been having a meeting for the last two or three days about, ‘Okay, we have X number of dollars in inventory. Can we pull a couple hundred thousand dollars out of inventory in case we end up being cash flow negative for the next two months?’” Plus: finding ways to help other struggling businesses and looking for opportunities to emerge from this stronger.
Karen, Jay, and Dana talk about the contingency plans they’re making as we head into the health and economic crises presented by COVID-19. Can they keep paying hourly workers? Can they keep their locations open? Can they find the resolve to hang on no matter where this goes? “You're gonna get through this. You're gonna do what you need to do. If you need to close the one salon, so be it. And you're going to come out of this whole thing because you're smart, and you're ambitious, and you're responsible, and people like you. You're gonna get through this.” Plus: is now the time to join a business peer group?
Nobody goes into business because they think they're going to be really good at firing people. When you read books or magazine profiles of business leaders, you rarely hear anyone say, “You know, the one thing I've really mastered is knowing when and how to fire people.” And yet it’s something that every entrepreneur has to deal with. Even at the most successful businesses, some employees are not going to make it. In this episode, regulars Karen, Jay, and Dana answer the question: how many people have you had to fire or lay off? Plus: What do you do when you find you have venture-backed competition?
In Part 2 of our special taping in front of a live audience at Blink UX’s headquarters in Seattle, Brian Canlis talks about how he and his brother took over the family restaurant and what happened when they decided to modernize its operation: “We did lose 10,000 guests that year. And we lost money for the first time as a company ever that year. And we got three negative reviews in the paper. And we were averaging about a dozen complaint letters a week about how much they thought Mark and I were destroying a family legacy. That was a low moment.” Regulars Karen Clark Cole, Jay Goltz, Dana White, and Laura Zander join the conversation as well. Plus: how Canlis gets employees to work harder for less money.
In a quick update, Karen, Jay, and Dana talk about how the coronavirus pandemic has already affected their businesses and how they are planning for the future.
In this special taping in front of a live audience at Blink UX’s headquarters in Seattle, Karen, Jay, Dana, and Laura talk about the risks of fast growth and why they haven’t taken investment capital. “I was so focused on growing that I kind of blew it up. I blew the whole business up by hiring people who we weren't ready to hire for. We were probably doing $5, $6, $7 million dollars in sales. I didn't need a $90,000 a year social media person 10 years ago. I just didn't, but I listened to what other people were telling me.” Plus: Dealing with competition.
Karen, William, and Laura discuss taking investment capital, dealing with stress, and why Karen’s going on sabbatical: “I just thought, ‘Okay, okay, I'll go.’ Then of course, I'm worried, like, ‘What if everything goes better without me?’” Plus: how are you managing health insurance costs?
Jay, William, and Laura discuss whether a great culture produces a successful business or whether a successful business produces a great culture. Do you think of your employees as family? Do you have anyone working for you whom, if you had it to do over, you wouldn’t hire? Plus: do you manage your Glassdoor page?
Jay, Dana, and Laura talk about risking it all, figuring out digital marketing, and connecting with your target audience: “Right now, my market is predominantly African American, but we have a lot of redheads. We have a lot of women of Indian and Middle Eastern descent.” Plus: how do you know if franchising makes sense for your business?
Jay, Karen, and Laura talk about competing on the internet, buying a supplier, and whether to take venture capital: “Who needs to answer to somebody if you don't have to?” Plus: after the Domino’s decision, what happens if your website isn’t disability compliant?
Loren and Karen talk with four of EY’s Entrepreneurial Winning Women about opening the books, bootstrapping a tech company, selling a business for more than $100 million, competing with Amazon, hiring hard-to-get talent, and pitching investors: “I've always said, ‘I'd rather be 75 percent of a watermelon than 100 percent of a grape.’” Plus: how much of your life do you have to sacrifice to be successful?
Jay, Karen, and William talk about pricing, custom manufacturing, and content marketing: “There have been people who would have been very good at a job, but they aren't willing to or able to put together content, and that just doesn't work for us.” Plus: the SEO value of an unusual last name.
Karen, William, and Laura talk about being a bad CFO, dealing with a disappointing profit margin, and the true price of growth: “I think our commitment to being cash-based and debt-free has been more important to me than the big number at the end of the year.” Plus: hiring employees vs. hiring contractors.