In The Trenches: Recent Episodes
Steve Divitkos
The only podcast dedicated exclusively to Entrepreneurs and CEOs running Small to Medium Sized Businesses (SMB).
Nobody knows what it’s like to be an Entrepreneur or CEO unless you’ve been one. Though many understand the rewards of company leadership, very few understand the arduous journey that’s required to get (and stay) there.
I share my own lessons as an Entrepreneur and CEO, and interview experts spanning Sales, Leadership, Mental Health, M&A, and Operations (among others) all with a single goal: To improve the personal and professional lives of Entrepreneurs and CEOs running SMBs.
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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Rob Markey is the creator of the Net Promoter Score ("NPS"), which has grown to become the de facto metric for measuring the health, loyalty and satisfaction of a customer base. He is also a longtime Partner at Bain & Company, where he founded and leads their Global Customer Strategy practice.
Rob is the co-author of The Ultimate Question 2.0: How Net Promoter Companies Thrive in a Customer-Driven World, a New York Times and Wall Street Journal bestseller.
Rob also teaches at Harvard Business School, and serves on several nonprofit and corporate boards, where he helps leaders build customer‑centric businesses.
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
Today I'm joined by Sherman Black, a CEO coach who focuses primarily on leaders running small and mid-sized enterprises.
In our discussion today we cover a wide range of topics, including some of the following:
- Misconceptions around what CEO coaches do (and don’t do)
- When & how to hire a coach
- How to think about cost and ROI in making that hiring decision
- Whether a coach needs direct experience as a CEO themselves
- Whether your coach should have a direct line of communication with your Board and/or senior leadership team
- How to quickly evaluate the health of the relationship between the CEO and her direct reports
- How coaches think about popular small business operating systems like EOS
- …and many others
Please enjoy!
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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Over four years ago, in February of 2021, I decided to publicly share the emotional and psychological realities of my journey as an Entrepreneur and CEO between 2012 - 2020. In publishing my first ever blog post, I suppose I had four primary objectives:
- First, to make a small contribution to the collective understanding, awareness and discussion surrounding issues of mental health, particularly that of Entrepreneurs and CEOs.
- Second, to simply discuss my challenges publicly. After all, if I didn’t do my own part to contribute to the discussion around the worries, thoughts, and fears that Entrepreneurs and CEOs face, what right did I have to lament the fact that they weren't being discussed enough more broadly?
- Third, to speak to any leaders who might have been experiencing feelings similar to those which I had felt
- And, finally, to share some of the lessons that I had learned as a result of dealing with these challenges, some of which only became clear to me with the benefit of time and hindsight
In re-publishing that post today, my goals remain the very same.
Though I had no plans or expectations after publishing the article in 2021, that single post was the first of 119 others that have followed over the past 4.5 years. I hope that at least one of these episodes has informed - perhaps even helped - some aspect of either your personal or professional life.
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
Today we take a deep dive into the concepts of customer retention and revenue quality in recurring revenue businesses. To help me unpack these ideas, I'm joined by Craig Zingerline, a serial entrepreneur who is now an advisor and mentor to a wide array of startups and technology companies. Among other things, we cover:
- A deep dive into the most common retention metrics, including which are most and least informative
- Situations in which high retention metrics might actually tell you that something is wrong within the business
- Things that he looks for that tend to be predictive of future customer retention
- Whether he cares about the difference between voluntary and involuntary churn
- How he thinks about software companies with high levels of service revenue
- Whether transactional revenue ought to be valued the same as per-user revenue
- And what else he looks at to evaluate the revenue quality of any given recurring revenue business
Please enjoy!
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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Although the vast majority of Search Funds seek to acquire businesses that are both “asset-light” and “capital-light” (that is, companies that don’t have a large base of tangible assets that need to be added to, refurbished, or replaced to either maintain operations or pursue growth), I don’t believe that the mere presence of capex should necessarily disqualify a company from consideration.
In this episode, we begin by exploring the circumstances within which capex can be a tolerable part of any given deal, and we’ll conclude by discussing how buyers should adjust their approach to valuation based on the asset intensity of the target company in question.
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
Today’s episode explores the intersection of healthcare and private investing, and specifically explores the merits and risks of acquiring the actual healthcare providers themselves.
To help me explore this thesis, I could think of no better guest than Scott Becker. Scott is a Partner in the healthcare groupat McGuireWoods, a full-service U.S. law firm that serves clients ranging from startups to Fortune 500 companies. He previously served on the Board of Partners of the firm and chaired the Healthcare group for nearly 13 years.
He provides counsel to hospitals, Ambulatory Surgery Centers, surgical hospitals, pharmaceutical companies, single- and multi-specialty medical practices, and a variety of healthcare industry entrepreneurs.
Please enjoy!
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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Today's episode is all about the Finance & Accounting function: My guest is Nicholas Andrews, who is the Founder of Aspen Consulting Group, a company that performs finance, accounting, and operations consulting for a wide range of small and medium sized businesses.
Our conversation begins with several questions about how to manage cash and other sources of liquidity amid all of the macroeconomic volatility & uncertainty we’re currently witnessing. We then discuss the topic of employee financial literacy, including the question of how transparent CEOs should be with company financials, and then move to questions of capital allocation and how CEOs should think about spending the cash that they generate, and finally we conclude with several considerations related to hiring, specifically focusing on the question of how CEOs should think about hiring a senior finance & accounting leader.
Please enjoy!
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
My guest today is Collin Hathaway, the Founder of Skylight Capital, a micro-cap private equity firm that invests primarily within the home services ecosystem.
Collin got his start as an entrepreneur after acquiring a small plumbing company at the outset of the great financial crisis in 2008. Since then, he has acquired and operated several other home services companies operating within the plumbing, HVAC, and roofing verticals, to name just a few.
In our conversation today, we cover how the home services market has evolved since he first entered it in 2008, his views on organic versus inorganic growth theses within home services, whether the market is too competitive today, what he’s learned about the art (and science) of raising money, how he communicates bad news to investors, and what he learned from experiencing a heart attack at only 36 years old.
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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When evaluating a small business to acquire, to suggest that some form of concentration is common is likely an understatement. Indeed, in most cases, concentration of some variety is a borderline inevitability. Though this often takes the form of customer concentration (the focus of this blog post), it can take other forms as well, including key person concentration, supplier concentration, reseller concentration, and technology/platform concentration, among other forms.
The aim of this blog post is to discuss when customer concentration is acceptable (and when it is not), how to incorporate its associated risks into the transaction’s price and structure, how to diligence the likelihood of those risks manifesting, and the types of business models where the defection of large customers should be viewed as an expectation, and not as an improbable risk.
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
Today's guest, John Ratliff, is a lifelong entrepreneur who founded a call center company called Apple Tree Answers, which he scaled through 24 separate bolt-on acquisitions, growing it over 3,000% prior to selling to a strategic buyer in 2012. He then went on to become a partner at an investment bank, where he has advised on countless small business transactions. All told, he has sat in nearly every seat at the M&A table — as a founder, buyer, seller, and now advisor. In our conversation today, we cover:
- How he reduced frontline turnover from 115% annually to 18% annually
- Lessons from acquiring 24 companies, including what he did differently in deals 23 & 24 relative to deals 1 & 2
- How John stayed intimately connected to 650 employees across 24 locations
- How he designed himself out of the day-to-day operations, spending just 15–25 hours per week inside of his business
- How to spot real sellers, how to navigate the notoriously tricky transition between incoming & outgoing CEOs, and how to identify red flags in due diligence
Please enjoy!
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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If you have ever had to decide how to price a product or a service, or if you foresee yourself having to make such a decision one day, I implore you to listen to today’s episode, in no small part because of how many practical takeaways you’re likely to leave with.
I’m joined today by Casey Brown, the founder of Boost Pricing, a consulting company that helps their clients with all things pricing, including not just setting prices, but also the often overlooked tactical details of how to actually go about executing on pricing changes.
In addition to being the Founder of Boost pricing, Casey is also a prominent keynote speaker, having delivered a TEDx talk in 2015 with over 5 million views to-date. She has degrees in both Chemical Engineering and Business, and if you listen to our conversation today, you won’t be surprised to hear that Casey cares about three primary things when it comes to her clients: Being fearless about price increases, getting paid what they’re worth, and increasing profitability fast.
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
This week, I'm joined by Dr. Sherry Walling, a clinical psychologist, speaker, podcaster, and best-selling author. She is also the Founder of ZenFounder, which aims to help entrepreneurs and CEOs navigate issues of transition, rapid growth, loss, and any manner of complex human experience. She is also the host of the ZenFounder podcast, which has been called a “must listen” by both Forbes and Entrepreneur Magazine and has been downloaded more than 1M+ times.
Sherry first came onto my radar when she published her first book, the aptly named The Entrepreneur’s Guide to Keeping Your Sht Together*, which discusses many of the topics that we’ve explored over the years in this podcast related to managing your psychology as an entrepreneur and CEO.
Her most recent book is titled Exit Strategy: The Entrepreneur’s Guide to Selling Your Business without Regret, which goes beyond purely commercial considerations, and explores the largely unexplored personal considerations specific to the largest transaction of most entrepreneurs’ lives.
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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One of the most common investment theses among acquisition entrepreneurs revolves around building an internal sales function where no such function has existed in the past. While this makes intuitive sense on the surface, just how easy is it to build a sales team from scratch? Do you hire the leader first, or do you hire an individual contributor first? Does it matter if your sales reps have experience in your particular industry? How do you evaluate the success of new hires if you have a long sales cycle? How do you change an incentive compensation plan in the middle of a fiscal year? Should lead generation be outsourced or brought in-house? How involved should a SMB CEO be in sales?
These are just some of the many questions that we explore with my guest this week, Dave Prusinksi. Dave is the Chief Revenue Officer at SafeAI, a hyper-growth silicon valley company in the autonomous vehicle space.
Prior to his current role, Dave spent 10 years as the Executive Vice President of Sales and Marketing at FleetComplete, a technology provider to fleet-owning businesses around the world. Under Dave's leadership, FleetComplete grew from $6M ARR to $150M in total revenue, achieving an average 50% revenue CAGR for 9 of his 10 years.
Dave played an integral role in the acquisition of 6 companies, leading the sales and marketing due diligence processes, and ultimately integrating the operations of the acquired businesses into that of FleetComplete. Dave was also a central member of the deal team helping to lead FleetComplete through multiple investment and acquisition rounds themselves, managing the sales & marketing due diligence processes in each instance.
Dave has served as a Revenue Coach to several SMBs, working directly with their CEOs and Heads of Sales to optimize their sales and revenue generation processes. All of the companies with whom Dave has worked thus far have now exited with great success.
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
This week, I attempt to educate listeners on several non-obvious considerations - highly specific to the enterprise software business model - that must form a core part of any diligence and deal structuring process.
Today’s episode will be broken into 3 segments:
In part 1, I will discuss several financial considerations that differentiate a software acquisition & diligence process from a more "traditional" one
In part 2, I discuss several product-specific considerations that prospective acquirors ought to pay particular attention to, especially those who are non-technical, with no prior software experience
Finally, in part 3, I outline 5 very different ways in which prospective acquirors can go about structuring the acquisition of a software company, because – as you’ll hear – not all software investment theses are created equally.
Please enjoy!
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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Today’s episode is all about Hiring, and we’ve managed to secure one of the world’s foremost experts on the subject.
Randy Street is the Vice Chairman of ghSMART, a global consulting firm that helps CEOs, boards, and investors build valuable companies specifically through hiring and developing world class leadership teams. Alonside ghSMART’s chairman and founder, Geoff Smart, Randy also co-authored Who: The A Method for Hiring, a book that I view as being required reading for all entrepreneurs and CEOs running SMBs. The very specific hiring method that they detail within this book ("Topgrading") changed the way that I made all of my hires across my entire company.
In our discussion today, we discuss how to evaluate people & teams that you haven’t personally hired, post-hire considerations, lessons from 30+ years of working with CEOs and management teams, compensation, and how to identify and address conflicts within leadership teams.
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
Across all known search funds since the inception of the model in the 1980s, ~63% of funds have gone on to acquire a company. However, since 2014, the acquisition rate has decreased, hovering around ~57% over the past 10 years.
Today I'm joined by three of the most experienced and respected investors within the search fund ecosystem to discuss A) Why the acquisition rate among search funds has fallen over the past 10 years; and B) Whether the rate of acquisition is likely to fall further in the years to come.
Joining me today are Jim Edmunds (Search Fund Partners), Badge Stone (WSC), and Kent Weaver (Granite Point Partners).
Today's episode revolves around the testing of 8 hypotheses, submitted to us via a survey of 1,000+ searchers & CEOs. Those hypotheses include:
Encroachment: PE moving further down market?
Capacity: Investors with too many searchers in their portfolios?
Competition: Too many search funds in the market?
Dilution of Talent/Commitment: Too many part-time searchers?
Valuation Expectations: Sellers no longer willing to transact at palatable multiples?
Cost of Capital: Search funds have a higher cost of capital relative to other buyers?
Searcher Fatigue: Sellers and intermediaries becoming disillusioned with the value proposition of search funds?
Email: Deliverability challenges too much to overcome?
Please enjoy!
This episode is brought to you byOberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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This episode is brought to you byBoulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
*Raam Jani is one of the most experienced lawyers in the Search Fund ecosystem, and within the small business M&A ecosystem more broadly. In our discussion today, we cover some mechanics (including when one should begin the legal diligence process, how to avoid overwhelming sellers with too many information requests, and how he deals with situations where his legal counterpart is less experienced in matters of M&A). We cover frequent stumbling blocks within the M&A process (including how to evaluate the true extent of the key person risk that resides within any given seller, what areas of the purchase agreement tend to be most contentious, and why he advocates for rep & warranty insurance). And finally we conclude with some general market observations, including whether he thinks the lower middle market is as inefficient as it was 5-10 years ago.
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
As an American searcher, are you aware that you might be able to receive $10M+ of your exit proceeds completely free of federal tax? As a Canadian searcher, are you aware that you might be able to receive $1M+ of your exit proceeds completely free of federal tax? If you’re not, then you might want to give this episode a listen.
We split today’s episode into two parts: The first half will focus on US searchers and investors, and will explore the QSBS program (aka Section 1202) offered by the US federal government.
The second half (starting at the 47 minute mark) will focus on Canadian searchers and investors, and will focus on the CCPC program and the lifetime capital gains exemption offered by the Canadian federal government.
Both programs have the potential to be incredibly lucrative for searchers and investors alike, though both remain unfamiliar to many. I hope this episode plays a small role in changing that.
Timestamps
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USA: 0:00 - 47:00
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Canada: 47:00 - 1:11:00
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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Dr. Daniel Crosby is a behavioral finance expert, the Chief Behavioral Officer at Orion Advisor Solutions, a ClinicalPsychologist, and a New York Times best-selling author. In our wide-ranging discussion today, we discuss meaning, purpose, fear of the unknown, when to continue vs. when to persist, why we tend to ignore simple solutions to complex problems, why pessimism sounds more intelligent than optimism, how to use our money to buy back time, and how to spend our money in ways that will maximize happiness and contentment.
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
The "long term hold” strategy is one that has received an increasing amount of attention within the acquisition entrepreneurship ecosystem of late. To further explore this thesis, I was joined by Zac Carman, CEO of ConsumerAffairs.com for 14+ years. In our discussion, we unpack Zac’s long-term-hold strategy and discuss the extent to which it was deliberate or emergent, how he has managed liquidity requirements for both himself and his investors, the commercial and personal reasons why a LTH strategy makes sense for him, and if he thinks it makes sense for an entrepreneur to target a LTH strategy before acquiring their first company.
This episode is brought to you by Oberle Risk Strategies:Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
Archimedes said “Give me a lever long enough, and a place to stand, and I will move the earth.” Though the concept of leverage is most commonly associated with the use of debt to finance the acquisition or operations of a company, there are countless other forms of leverage that we ought to be aware of, given that all of us have to contend with the reality of finite time and resources. Instead of asking what else they should be doing to achieve their goals, entrepreneurs and investors might instead consider asking: “How can I magnify the impact of what I’m doing, without doing more of it?”. Today we explore 10 different forms of leverage, and provide a few ideas around practical application.
This episode is brought to you by Oberle Risk Strategies:Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
Want to know what it's like to work with me as an investor? Check out our testimonials page here.
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Those who have never run a rapidly growing company are unlikely to appreciate the operational challenges associated with doing so. Indeed, while running my own company, I found our highest growth year to be the most difficult, both operationally and personally. We outgrew our systems, had to change our people, had to add entirely new departments, and I found that my own role as the CEO had to evolve both quickly and significantly.
To help us better understand the day-to-day realities associated with running a high-growth company, we're joined today by Anth Georgiades, co-Founder and CEO of Zumper, North America's largest apartment rental platform. Since it's founding in 2012, Zumper has grown revenue at triple-digit annual growth rates, and has raised over $150M in Venture Capital funding. Today, Zumper boasts over 250 employees, and 75 million active users.
This episode is brought to you by Oberle Risk Strategies:Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
Want to know what it's like to work with me as an investor? Check out our testimonials page here.
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Franchise ownership is an entrepreneurial path that remains under-discussed and under-explored within the small business community. Yet, for the right person, it can represent a highly lucrative opportunity with several built-in risk mitigation mechanisms. My guest today, Michael Horowitz, acquired 7 Wingstop locations in 2018 and continued to grow his footprint over the next 5 years until a successful exit to a strategic acquirer in 2023. As we discuss in our conversation, the entrepreneurial gods don’t deduct any points for leveraging a business model that is proven to work.
This episode is brought to you by Oberle Risk Strategies:Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
Want to know what it's like to work with me as an investor? Check out our testimonials page here.
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Back by popular demand today, for his second tour of duty on the podcast, is Brent Beshore. Brent is the Founder and CEO of Permanent Equity, a private investment firm that invests in Founder-owned small to medium sized businesses. Beyond his commercial acumen, one of the things that I most admire about Brent is how he takes a deeply personal approach to his work, utilizing tools and frameworks from disciplines like philosophy, psychology, and religion to inform how he thinks about conducting himself both personally and professionally. This is one of the reasons why a seemingly black and white conversation about investing went into domains like fear of failure, the source of our identities, and why young professionals ought to demonstrate more vulnerability, among other topics. My first conversation with Brent, published in November of 2022, was one of our most highly rated episodes, and something tells me that this one might even top it.
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
*This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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Want to know what it's actually like to work with me as an investor? Check out our testimonials page here.
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Today's episode features five unrelated thoughts on how to lead and grow a healthy and vibrant company. None of them are long enough to justify a stand-alone blog post, but all of them are important enough to highlight for current and aspiring CEOs.
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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Properly managing the relationship with the outgoing seller is likely to be among your mostimportant tasks within your first 6 months as the new CEO. I say this because a non-functional (or worse, a toxic) relationship between the incoming and outgoing owners has the potential to damage a company more than customers leaving, employees quitting, or competitors fear-mongering ever could. To help us better understand the perspective of a selling Founder, I was joined this week by three founders, all of whom chose to sell their companies to a Search Fund within the past few years. Joining me today is Alicia Browner (Founder of Prelude), David Marshall (Founder of Performio), and Robert Day (Founder of Integrity Advocate).
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
*This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
Rich Manders has done almost everything that an entrepreneur and CEO can conceivably do: He co-Founded a Massachusetts-based automation company and grew it to $90M in revenue. He sold that business to a Private Equity firm, then stayed on with the business to help them acquire 7 tuck-ins, growing the company by 6x and producing a 50% IRR. He has since started a coaching practice, and now works with SMB CEOs across North America. His story is the subject of a Harvard Business School case study, where he has also taught several courses and seminars.
Our discussion today covers how PE buyers are likely to evaluate your business, including internal systems, capital allocation, management team quality, pricing, and countless other variables.
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
Today I am thrilled to welcome Carl Richards to the podcast. Carl has spent decades as a Certified Financial Planner, is the creator of the Sketch Guy column (which appeared weekly for a decade in The New York Times), is a best selling author (most notably of The Behavior Gap: Simple Ways to Stop Doing Dumb Things with Money), is a podcaster (most recently, the host of 50 Fires: A Podcast About Money and Meaning), and is a frequent contributor to countless financial and other publications, including Morningstar Advisor, Marketplace Money, Oprah.com, and Forbes.com, among others. In our conversation today, we cover: How in some instances money can indeed buy happiness; Why money is like alcohol; Why you should aim to “die with zero”; How to run small experiments to see what types of spending are likely to produce happiness for you*; Why you may want to think about money as you would gathering firewood in a remote cabin in the wilderness; And much, much more.
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
*This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
- As an entrepreneur myself, it’s clear to me that in some ways the realities of my chosen career path have magnified and heightened the challenges that are common to all relationships, and in other ways have added completely new dynamics that most other couples can’t directly relate to. Today, I attempt to shine a light on the role that spouses play in the entrepreneurial journey from the perspective of both the spouse and the entrepreneur. To help me do this, I’m joined by Dr. Jennifer Musselman, a globally-recognized Marriage and Family Therapist and Executive Coach for high-performing executives and entrepreneurs. Dr. Musselman’s clinical work focuses on the interplay of work, life, self-identity and marriage, including the common stressors that impact performance and relationship satisfaction for entrepreneurs and other business leaders.
Link to The Entrepreneur and the Spousal Relationship: Part 1
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
- This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
*Today I'm joined by Dr. Bill Hudenko, an Assistant Professor of Clinical Psychology at the Dartmouth School of Medicine. In addition to his experience as a professor and clinician, Dr. Hudenko is also a 4x CEO & Entrepreneur, having founded and sold several companies that have utilized technology to improve mental health outcomes for customers. Because of his incredibly unique career that spans coding, entrepreneurship, psychology, medicine, leadership, and technology, we had a very wide ranging conversation that I think you’re really going to enjoy.
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
*This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
- My guest today is Jim Vesterman, currently a lecturer at the Wharton School at the University of Pennsylvania. Prior to joining the faculty at Wharton, Jim was the CEO of Raptor Technologies, a company that he purchased through his own search fund in 2012, and ran through to a successful exit in 2020. Under Jim’s tenure, Raptor technologies grew from serving 7,000 schools in the United States to serving over 40,000 schools with an integrated suite of K-12 school safety software.
Jim ultimately sold the company to JMI Equity, and returned an astounding 13.5x MOIC and 53% IRR to his search fund investors.
Jim also served in the United States Marine Corps in the Special Operations forces and was awarded the Combat Action Ribbon and the Navy and Marine Corps Achievement medal for his service in Iraq in 2004.
Jim graduated from Amherst College with his bachelor’s degree in Economics and Spanish and earned his M.B.A. from the Wharton School in 2006.
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
- This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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During my ~10 years as a searcher and CEO, I had an endless number of commercial problems and opportunities that required my attention at any given time. However, it was often the personal considerations that kept me up at night: I rarely lost sleep over whether to raise prices by 5% or 15%, but instead was kept awake by the idea that even asking the question suggested that I didn’t truly know what I was doing. I wasn’t anxious about what mix of equity and debt to include in a letter of intent, but was instead anxious about the prospect of not finding a company to acquire at all after spending two years in pursuit of one.
For this reason, I thought it might be helpful to compile some of the lessons that I’ve learned over the years that cover the “human side” of acquisition entrepreneurship. I hope at least one of them provides you with a reason to reflect on your own situation, and perhaps make a change for the better in the process.
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
*This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
- Based on my own experience as a software CEO, I think that Product Management is one of the most important - and one of the lest well understood - ingredients to building a successful software company. Many software businesses (particularly mature ones still led by their original Founders) don't have any product management function at all. While this may be tenable under the Founder's leadership, it is almost never tenable when the company is acquired and led by a CEO with minimal industry experience.
It is also my experience that many problems that seem to be attributable to the engineering group (technical debt, high levels of customization, regularly missing deadlines, etc.) are actually product management problems masquerading as development problems. This episode, originally published in 2021, is as applicable today as it was then.
My guest today is Rich Mironov, who is North America's preeminent Product Management thought leader. He has spent 40 years in the software industry in numerous capacities, and currently acts as a Coach, Consultant, and Interim Executive for CEOs and Heads of Product across Canada and the United States, advising them on a diverse range of issues spanning product, marketing, engineering, and sales. Rich has led Product Management at six software companies, and has now consulted for more than 170 technology businesses of all sizes. He is the author of "Product Bytes", a hugely popular and long-running blog on software, start-ups, product strategies, Silicon Valley, and the inner life of product managers. Our conversation covers hiring a Product leader and Product team, how to think about prioritizing products/features/functions, how Product should interface with Sales and other internal departments, how involved CEOs should be in Product, and what fatal mistakes he’s seen Product Managers make.
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
- This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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Though it is correct to suggest that all acquisitions are funded through some combination of cash-on-hand, debt, or equity, it’s also a bit of an oversimplification. Indeed, the financing options available to prospective acquirors are numerous, and in today’s blog post, I focus specifically on debt, and evaluate the four most common sources of leverage used to finance the purchase of small and medium-sized businesses. These include bank debt, mezzanine debt, seller financing, and SBA loans.
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
*This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
I recently published a blog post, Why You May Want to Reconsider Your Industry Roll-up Strategy, within which I detailed many of the ways in which consolidation strategies can go wrong. In today’s episode, I want to look at the opposite side of that coin and dig deeply into an instance where a consolidation strategy went very right.
I'm joined today by Jay Davis & Jason Pananos, who, after graduating from business school in 2008, acquired Vector Disease Control, a company that they grew from ~$7M to ~$50M in revenue in ~7 years through successfully executing on 14 bolt-on acquisitions.
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
- This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
*Today’s episode is all about participating in brokered transactions, and working with brokers more broadly (by "brokers", I am referring to investment banks, accounting firms, business brokers, or any other sell-side advisor whose job it is to help clients sell their companies). To inform our discussion today, I’m joined by Ryan Farkas, a Partner, Managing Director and the Practice Leader in M&A and Capital Markets at BDO, who has successfully closed countless sell-side advisory transactions spanning dozens of industries.
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
*This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
- Though pursuing the consolidation of an industry is not necessarily a new thesis within the search fund ecosystem, I have observed that it has become increasingly popular over the past few years among prospective searchers. Though there have been, and will continue to be, many consolidation success stories within the search fund ecosystem, I suspect there will be an equal number of failures, though this latter outcome will surely be much less publicized. Though I’m not against consolidation theses in and of themselves, I do find myself more skeptical than most when presented with one. In today’s blog post, I’ll attempt to explain why
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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In a previous post (75 Things That I Think Are True), I compiled quotes from countless books, mentors, podcasts and blogs to present 75 ideas that I believed to be fundamentally true, spanning both business and personal considerations. Since publishing that post last year, I have come across 45 additional quotes that I thought were also worthy of presentation. I hope that some of these new submissions also distill a lifetime of wisdom into only a few words.
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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Constellation Software is one of the world's most widely followed and admired software companies, having acquired upwards of 500 lower-middle-market software companies since its founding in 1995. Our guest today, Mike Dufton, is the CEO of the Volaris group, one of the six major operating units within Constellation, that itself owns upwards of 200 portfolio companies.
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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After many years of using company stock options as attraction, retention, and incentive alignment tools, I’ve come to appreciate their merits, risks, and possible alternatives. I intend to share these lessons with you today. More specifically though, I will argue that while options do have their time and place, there are often much simpler and less expensive alternatives that arguably have a greater impact on attraction, retention, and incentive alignment.
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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Today I'm joined by entrepreneur, CEO, and best-selling author, Rob Dube. In 1991, Rob co-founded imageOne,a managed print services business based in Oak Park, Michigan, that has won countless awards across countless publications for it’s growth, culture, and employee engagement, among many other accolades.
Today we discuss Rob's newest book, Shine: How Looking Inward Is the Key to Unlocking True Entrepreneurial Freedom. This book is all about how CEOs can manage their inner worlds, which stands in stark contrast to most business books, that focus almost exclusively on how CEOs can manage their outer-worlds. Rob co-authored the book alongside Gino Wickman, who is the author of the widely-read Traction, the book that introduced the world to the Entrepreneurial Operating System ("EOS").
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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Many searchers understandably tend to have very similar questions and areas of uncertainty. Indeed, in most instances, I had these very same questions and areas of uncertainty myself prior to raising my own search fund in 2012. As a result of the frequency with which I'm asked these questions, I've presented each of them in today's episode, and have also included my opinion on what the answers may be. Some of the questions include:
- Constructing a cap table
- Differences between the Canadian and US search ecosystems
- Is the search fund market too crowded/saturated
- The trade-off between price and business quality
- What the best searchers do in their first 3-6 months
- Proprietary vs. brokered deal flow generation
- When to visit a prospective seller
- Success rates of industry agnostic searches
- Having an industry & geographic focus
- Homogeneity among search investors re: industry preferences
- How to spend your first week as a new CEO
- Should I create a 100-day plan?
- How to communicate the ownership change to customers
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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Today I'm joined by Entrepreneur, Investor, and Author Mike Michalowicz. In addition to being the author of 9 books, Mike is himself a serial entrepreneur, having founded, operated, and successfully exited several companies across his multi-decade career. He now spends much of his professional time writing, speaking, and coaching CEOs and entrepreneurs on the various systems that helped make him successful, including (and especially) his "Profit First" system, a highly tactical guide to organizing your entire company around achieving endurable profitability.
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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Today I am thrilled to be joined by two guests that, without the risk of hyperbole, have changed my life in more ways than I can count. Royce Yudkoff & Rick Ruback are both professors at the Harvard business school, and co-teach two wildly popular courses called “The Financial Management of Smaller Firms” and “Entrepreneurship through Acquisition”, both of which focus on how to acquire, finance and operate your own smaller firm. They also co-published the widely read book, The HBR Guide to Buying a Small Business, published by Harvard Business Review Press, which acts as the definitive source of wisdom and guidance for a countless number of acquisition entrepreneurs
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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Today I'm joined by two of the most thoughtful, distinguished, and respected investors in the ETA ecosystem, Jeff Stevens and A.J. Wasserstein, to discuss the future of acquisition entrepreneurship. The paper that inspired this episode, written by both Jeff & A.J., can be accessed here:
Jeff Stevens is the Founder of Anacapa Partners, a firm with over 20 years of experience structuring, operating and investing in search fund-owned companies. Jeff was an acquisition entrepreneur himself, having managed 3 funded searches during the period from 1990-2005, each one culminating in the acquisition of a SMB.
A.J. Wasserstein is the Eugene F. Williams, Jr. Lecturer in the Practice of Management at the Yale School of Management. His research, writing, and teaching concentrates on search funds, entrepreneurship, programmatic acquisitions, and small businesses. In addition to his role as an educator, A.J. is also a private investor in lower middle-market businesses.
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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Today I'm joined by Michael Girdley, an entrepreneur and investor who has spent the past 30 years building a personal holding company boasting over $100M in annual revenue, comprised of 12 businesses across software, technology, consumer retail, and education, among others. Outside of managing his holding company, Michael is deeply involved in the North American SMB ecosystem: He co-hosts Acquisitions Anonymous, a podcast that reaches over 10,000 listeners weekly, where he and his co-hosts dissect real businesses currently up for sale. He also offers two online courses, educating prospective entrepreneurs on the Holding Company model, as well as best practices on how to find and acquire a great small business. He is also an active investor in small- and medium-sized software companies through another holding company, Dura Software, that invests in mission-critical B2B software companies spanning multiple niches.
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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Over many years of evaluating acquisition targets alongside searchers, I’ve found that certain questions tend to apply more often than not. I’ve presented each of these FAQs in today's episode, in hopes that they play a small role in how you structure your own due diligence process, and in turn how you think about the relative merits and risks of the opportunity in question. If you're a buyer, the list that follows can be thought of as a starting point for “Commercial Due Diligence 101”. If you're a seller, you should be prepared to address each of these questions and information requests if you're ever planning to sell your small to medium sized business. Please enjoy!
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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In today's episode, I will be speaking with 3 searchers, each of whom are at different stages of their respective search journeys. As I have done in the past, I will again be asking these guests only a single question: Knowing what you know now, if you could go back and re-do the first 90 days of your search, what might you do differently? This question is an important one because every searcher that I’ve ever met (including myself) learns so much along the way, and as a result we often reflect back on our first few months and wish we knew then what we know now. My hope is that this episode will help you learn from those who have come before you in this regard.
This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community
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Today I'm joined by Dr. Victoria Medvec, a Professor of Management and Organizations at the Kellogg School of Management at Northwestern University. In addition to her professorship, Dr. Medvec is the CEO of Medvec and Associates, a consulting firm focused on high stakes negotiations and strategic decisions. She is also the author of the best-selling book, Negotiate Without Fear, which was published in 2021. Dr. Medvec is a renowned global expert in the areas of negotiations, often advising senior executives and Boards of Directors from companies around the world. Her clients include IBM, Cisco, McKesson, General Electric, Merck, McKinsey, BlackRock, Goldman Sachs, McDonalds, Bristol Myers Squibb, and J.P. Morgan Chase, to name just a few.
This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community
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This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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Today I'm joined by Peter Lehrman, the Founder and CEO of Axial Market. For those of you who don’t know, Axial is the North America’s #1 online platform that connects buyers and sellers of small and medium sized businesses. Axial is used by over 20,000 investors, M&A advisors and CEOs, allowing them to connect on a confidential basis to explore M&A, debt, buyout, and growth equity transactions, to name just a few. Over 10,000 transactions are posted each year on Axial, covering companies that generate anywhere between $2.5M – $250M in revenue. Prior to Axial, Peter worked in private equity at SFW Capital Partners and was part of the founding team at Gerson Lehrman Group (or “GLG”, for short), a platform where investors and other users are able to connect on-demand with experts spanning a countless number of industries and disciplines.
This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community
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Kaley Klemp is a highly sought after CEO coach, YPO forum facilitator, and best-selling author. In 2015, Kaley co-authored The 15 Commitments of Conscious Leadership, a book that was met with instant critical and commercial success, and followed that up in 2021 with The 80/80 Marriage, a book about how to strengthen and build relationships between spouses using some of the tools, techniques and ideas that she had previously employed with her executive coaching clients. Within the Young Presidents Organization (“YPO”), Kaley has facilitated retreats for more than 200 member and spouse forums throughout the world, and is a highly sought after speaker, recently having presented at Google alongside her husband, and with her TED Talk, “Stop Trying to Change”, racking up over 20 thousand views on YouTube. Prior to her coaching, speaking, and facilitator roles, Kaley was a management consultant with Deloitte, and prior to that she was a student at Stanford University, where she earned a B.A. in International Relations and an M.A. in Sociology, with a focus on Organizational Behaviour.
This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community
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This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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My guest today is Brent Belzberg, Founder and Senior Managing Partner of TorQuest, a middle market private equity firm that he founded in 2002 that has since grown to ~$5.5B in assets under management. In 2018, Brent was appointed as a Member of the Order of Canada, Canada’s highest civilian honor, for his work as a business leader and philanthropist. He also received Queen Elizabeth II’s Platinum Jubilee Medal in 2023 for his significant contribution to Canada and the province of Alberta.
This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community
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I have debated whether to write this blog post for quite some time now. Because topics related to mental health tend to generate more engagement than other more commercially-oriented content, I didn’t want this post to be interpreted as being hollow or self-promotional in any way, to the extent that it generates higher-than-normal clicks or page views for me. In spite of this, two things compelled me to finally publish this: (1) I wanted to simply discuss the topic of anxiety publicly, in hopes that my doing so will play some small role in helping others feel comfortable doing the same. (2) My hope is that some subset ofreaders will respond to some subset of the points below with a nod of their heads, and a sentiment of “Yes, I’ve felt something similar myself”.
This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community.
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This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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I have spent the past several weeks going through almost 3 years of In The Trenches archives to tease out all of the best insights that we’ve been able to collect from each of our guests specific to Compensation. I won’t need to convince any CEO of how important compensation is, and how fraught with peril it can be when it isn’t done right. Below is a list of our guests and topics, which include timestamps, so you can skip between the segments that are most interesting to you:
- (3:06) Verne Harnish: Crafting Company-Wide Compensation Plans
- (20:55) Dave Prusinski: Sales Compensation
- (37:48) Rich Manders & Brent Beshore: Equity or Options as a Form of Compensation
- (51:00) Jim Sharpe: Managing Wage Inflation & Salary Expectations
- (55:05) Randy Street: Surprising Lessons Specific to Compensation
- (1:03:05) Bob Pritchett: Compensation Mistakes
This episode is brought to you by Symphony. On September 8th, 2023, Symphony will be live-streaming a webinar on searchfunder.com all about the technical due diligence process when acquiring a software company. Use this link to sign up: https://www.searchfunder.com/event/view/1200. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community
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I have spent the past several weeks going through almost 3 years of In The Trenches archives to tease out all of the best insights that we’ve been able to collect from each of our guests specific to Hiring. I won’t need to convince any CEO of how important the hiring process is, and how fraught with peril it can be when it isn’t done right. Below is a list of our guests and topics, which include timestamps, so you can skip between the segments that are most interesting to you:
- (3:30) Randy Street: Co-author of Who: The A Method for Hiring, which introduced the Topgrading hiring method to the world
- (22:39) Verne Harnish: Founder of the Entrepreneurs’ Organization (“EO”), & author of Mastering the Rockefeller Habits and Scaling Up
- (37:43) AJ Wasserstein: Professor at the Yale School of Management. Prior 2x CEO and active SMB investor
- (43:40) Mike Zani: CEO of The Predictive Index, and author of The Science of Dream Teams
- (52:27) Steve Divitkos: Hiring Your Senior Management Team: Founder of Mineola Search Partners
- (1:12:50) Anthemos Georgiades: Hiring in High Growth Environments: Founder and CEO of Zumper, an apartment rental platform that boasts 250 employees, 75 million active users, and 17 million app visits per month
- (1:27:09) Nicholas Andrews: Hiring for the Finance & Accounting Function: Founder of The Aspen Consulting Group
- (1:42:40) Rich Mironov: Hiring in Product Management: One of North America’s preeminent Product Management thought leaders, having spent 40 years in the software industry in numerous capacities
- (1:55:20) Dave Prusinski: Hiring in Sales: Former EVP of FleetComplete. Grew annual revenue by ~25x, achieving a ~50% revenue CAGR for 9 of his 10 years
This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community
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This episode is brought to you by Symphony. On September 8th, 2023, Symphony will be live-streaming a webinar on searchfunder.com all about the technical due diligence process when acquiring a software company. Use this link to sign up: https://www.searchfunder.com/event/view/1200. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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My guest today is Dr. William Irvine, author of the best-selling book A Guide to the Good Life: The Ancient Art of Stoic Joy, and one of the world's most influential writers on, and practitioners of, stoic philosophy. Dr. Irvine spent 38 years teaching at Wright State University in Dayton, Ohio, having recently earned Professor Emeritus status there. Dr. Irvine earned his BA in Mathematics and Philosophy from the University of Michigan and an MA and PhD in Philosophy at UCLA.
This episode is brought to you by Symphony. On September 8th, 2023, Symphony will be live-streaming a webinar on searchfunder.com all about the technical due diligence process when acquiring a software company. Use this link to sign up: https://www.searchfunder.com/event/view/1200. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community
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Recently, searchers have voiced an increasing level of interest in targeting “VC orphan” companies as acquisition targets: These tend to be healthy and modestly growing companies that have raised at least one round of institutional venture capital, have achieved product/market fit, but have failed to produce the triple-digit growth rates that are all but required for them to continue to command the time, attention, and capital of their VC-backers. Might searchers also consider this very different company profile, in addition to that which has served as the foundation of the Search Fund investment vehicle over the past three decades? Today's episode attempts to explore this question, presenting observations that both support and refute the thesis.
This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community.
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This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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My guest today is John Warrillow, author of the bestselling book Built to Sell: Creating a Business That Can Thrive Without You, and Founder & CEO of The Value Builder System, a sales and marketing software tool for business advisors to find, win and keep their best clients. Built to Sell was recognized by both Fortune and Inc magazines as one of the best business books of 2011, and has been translated into 12 languages since its initial publication. John is also the author of The Automatic Customer: Creating a Subscription Business in Any Industry and The Art of Selling Your Business: Winning Strategies & Secret Hacks for Exiting on Top. John is also the host of Built to Sell Radio, a hugely popular podcast where he has interviewed over 400 SMB founders about their exits. Forbes ranked Built to Sell Radio as one of the ten best podcasts for business owners. Before founding The Value Builder System, John started and successfully exited four companies.
This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community.
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Today’s episode is the second in a two-part series on when search funds don’t go as originally planned. On last week’s episode, we spoke with four entrepreneurs to get a first-hand account of how and why their paths deviated from their original plans. In today’s episode, we look to compliment those first-hand accounts with reflections from Jim Sharpe, a highly respected search fund investor of almost 20 years, and himself a former Searcher and CEO. Today we ask Jim to discusses the trends, commonalities, and themes that he has observed among searchers who failed to consummate an acquisition, and also those who did consummate an acquisition, but failed to "thrive" thereafter, either commercially or personally. Please enjoy!
This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community.
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This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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If one were to attend a randomly selected group of Search Fund conferences, they'd be forgiven for thinking that every search fund is a smashing success. When I was both a searcher and a CEO, I often left these types of events with a certain sense of insecurity and self-doubt, as everybody seemed to be more successful, more confident in their abilities, and more decisive in their actions. Yet, the data does not at all support the idea that everybody seems to be doing better than you are: One-third of search funds reliably fail to acquire a business, and of those that do, roughly one-third of them fail to return more than 1.0x the original capital. In today's episode, we speak with four entrepreneurs whose ETA paths deviated from their original plans, not only to learn from their hard-earned wisdom, but also to celebrate their courage and the wonderful professional successes that they've all gone on to achieve since.
This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community.
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Like many of you, I’m a sucker for a good quote. The best quotes often distill a lifetime of wisdom into only a few words, which is likely why some of them continue to resonate for decades (and in some instances, even centuries) after first being articulated. Over the years, I’ve compiled quotes from countless books, mentors, podcasts, and blogs, and in today's episode, I present this collection of quotes to you, in hopes that some of them impact you as much as they’ve impacted me. Most importantly though, I’m proud to finally be able to tell my wife that all of those years of highlighting books in bed have finally led to a tangible piece of output. I recognize that this is an typical format for our podcast, but my hope is that this episode will be more dense with wisdom and tactical advice than anything that I've published before (because the wisdom contained within is largely attributable to other people!). Please enjoy!
This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community.
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This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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To say that it's been an active 6-12 months in the banking sector would be an understatement: Beginning as recently as January, 2022, we've seen the US Federal Funds rate increase from .08% to 4.83%, the rapid collapse of Silicon Valley Bank, and the rescue of First Republic Bank by JPMorgan, representing the second largest bank failure in the history of the United States. Against this backdrop, CEOs and prospective acquirors of small businesses understandably have a lot of questions about their banking partners, their ability to secure loans, and the terms under which they might be able to do so. To get us up to speed on the state of lower-middle-market credit in North America, I'm joined by Anthony Rodriguez and Conor Tidgewell of Avidbank, who walk us through what has changed, the "new normal", and what it all means for entrepreneurs and CEOs running (or seeking to acquire) a small business. Please Enjoy!
This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community.
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When acquiring small to medium sized businesses, buyers often utilize a tool called an “earn-out”, which is a form of contingent consideration that sellers may receive at some point in the future in addition to the cash that they stand to receive at closing. Though earn-outs can be useful and mutually beneficial tools for both buyers and sellers under the right circumstances, without careful structuring and consideration they can fraught with risk and unintended consequences.
Before you propose an earn-out as part of your own acquisition, I’d encourage you to think through some of the risks and considerations that we discuss in today's episode. Please enjoy!
This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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This episode is brought to you by Avidbank. Avidbank is one of the most experienced search fund lenders in North America, having funded over 40 separate transactions since 2014, for a total of over $300M. They are deeply familiar with the search fund model, and understand the nuances of the fundraising process, dealing with sellers, communicating with your equity investors, LOI reviews, and everything else in between. Reach out to Anthony Rodriguez (arodriguez@avidbank.com) or Conor Tidgwell (ctidgwell@avidbank.com) to learn more.
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My guest this week is Andy Johns, whose memoirs could be titled "a tale of two careers". In his "first" career, Andy was an executive within the start-up and technology ecosystems, with growth and product oriented leadership roles at Facebook, Twitter, and Quora, among others. Following his time at these three companies, Andy became VP of Growth, VP of Product, and eventually President at Wealthfront, an automated investment platform that currently boasts $27 billion AUM across 470,000 accounts.
Now, in his second act, Andy spends his time helping others heal from emotional pain, transform themselves, and discover their life purpose. He is the Founder of clues.life, an online collection of wisdom, information, stories, and research on mental health, personal transformation, and the pursuit of meaning and purpose. He is also the author of a very popular substack, where he writes about the mental health struggles often faced by high achievers like himself.
This episode is brought to you by Avidbank. Avidbank is one of the most experienced search fund lenders in North America, having funded over 40 separate transactions since 2014, for a total of over $300M. They are deeply familiar with the search fund model, and understand the nuances of the fundraising process, dealing with sellers, communicating with your equity investors, LOI reviews, and everything else in between. Reach out to Anthony Rodriguez (arodriguez@avidbank.com) or Conor Tidgwell (ctidgwell@avidbank.com) to learn more.
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This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount!
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Though search funds have historically acquired companies within countless different industries, software has been among the most popular and sought-after industries among searchers for many years now. Because of this, I chose to conduct a survey of SaaS CEOs (who became owners/CEOs by way of the search fund model) for two reasons: (1) To better understand the complexion of the "typical" software acquisition within the search fund ecosystem; & (2) To see whether or not the the complexion of the "typical" software acquisition has changed over time.
As you will see from the data presented in today's episode, I feel safe in concluding that, yes, the profile of the typical SaaS acquisition has indeed changed over the past few years, in some cases quite materially. Today's episode will walk you through how and why I arrived at this conclusion.
Special Note for today's episode: Because this post is necessarily heavily on stats and graphs, I would strongly suggest viewing the blog post (as I can only verbally describe graphs so well!), which you can find here: https://mineolasearchpartners.com/2023/04/11/the-2023-saas-ceo-survey/
This episode is brought to you by The Profit Line. The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running my own company, and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit their LinkedIn page to learn how they might be able to help you exactly as they helped me.
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This episode is brought to you by Avidbank. Avidbank is one of the most experienced search fund lenders in North America, having funded over 40 separate transactions since 2014, for a total of over $300M. They are deeply familiar with the search fund model, and understand the nuances of the fundraising process, dealing with sellers, communicating with your equity investors, LOI reviews, and everything else in between. Reach out to Anthony Rodriguez (arodriguez@avidbank.com) or Conor Tidgwell (ctidgwell@avidbank.com) to learn more.
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Today, I'm joined by Kent Weaver, somebody who has decades of experience serving on the Boards of SMBs. Kent is an acquisition entrepreneur himself, having acquired a Sacramento-based health care business after a ~2 year search. After running the company for close to 9 years, he exited successfully, and has been investing in SMBs ever since. He has invested in over 150 search funds and 80 operating businesses, and has served on over 25 boards spanning health care, software, business services and consolidation strategies. Given Kent’s depth of governance experience, I thought he’d make a great resource for current or prospective CEOs who might be wrestling with questions related to how to construct, communicate with, and learn from their own Boards. Please enjoy!
This episode is brought to you by Avidbank.Avidbank is one of the most experienced search fund lenders in North America, having funded over 40 separate transactions since 2014, for a total of over $300M. They are deeply familiar with the search fund model, and understand the nuances of the fundraising process, dealing with sellers, communicating with your equity investors, LOI reviews, and everything else in between. Reach out to Anthony Rodriguez (arodriguez@avidbank.com) or Conor Tidgwell (ctidgwell@avidbank.com) to learn more.
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This episode is brought to you by The Profit Line. The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running my own company, and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit their LinkedIn page to learn how they might be able to help you exactly as they helped me.
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Among the countless strategic decisions that software CEOs must make, the decision of which end markets to serve doesn’t seem to command the time, attention, and level of thoughtfulness that it probably should. More specifically, substantially every small or medium-sized software company must answer the following two questions:
- Should I sell to SMBs or to larger enterprises?
- Should I sell my product into a single industry vertical, or multiple industry verticals?
Though these are of course not the only questions that software CEOs must answer with respect to the markets that they serve, they tend to be among the most important and most frequently posed ones. The purpose of this blog is to speak to both of these questions in turn.
This episode is brought to you by The Profit Line. The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running my own company, and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit their LinkedIn page to learn how they might be able to help you exactly as they helped me.
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This episode is brought to you by Avidbank.Avidbank is one of the most experienced search fund lenders in North America, having funded over 40 separate transactions since 2014, for a total of over $300M. They are deeply familiar with the search fund model, and understand the nuances of the fundraising process, dealing with sellers, communicating with your equity investors, LOI reviews, and everything else in between. Reach out to Anthony Rodriguez (arodriguez@avidbank.com) or Conor Tidgwell (ctidgwell@avidbank.com) to learn more.
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My guest today is Dr. Noam Wasserman, recognized as one of the world's foremost experts in how to form and maintain high performing partnerships in entrepreneurial contexts. Dr. Wasserman is currently the Dean of the Sy Syms School of Business at Yeshiva University in New York City, and was previously a professor at Harvard Business School for 13 years. His now famous book, The Founder’s Dilemmas, quickly became an Amazon #1 bestseller, and has since won countless awards. In our conversation today, we discuss what to consider when seeking out a partner, the important conversations that prospective partners ought to have with each other, what role passion and persistence should play in the entrepreneurial journey, and how to apply his various concepts and frameworks to our personal lives.
This episode is brought to you by The Profit Line. The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running my own company, and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit their LinkedIn page to learn how they might be able to help you exactly as they helped me.
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This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more.
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Though there are countless books, blogs, podcasts, and social media accounts that serve as thoughtful and informative resources for current and prospective entrepreneurs, unfortunately there appears to be an equal number of resources that demonstrate seemingly no limit to the fundamentally bad advice that they’re willing to impart upon others. "Hustle Culture" has unfortunately become so prevalent online that I felt it necessary to provide the entrepreneurial community with my own perspective on the matter.
This episode is brought to you by The Profit Line. The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running my own company, and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit their LinkedIn page to learn how they might be able to help you exactly as they helped me.
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This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more.
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This is a very special episode of In The Trenches: In today’s episode, I will be interviewing 4 different CEOs of 4 different SMBs, and asking them just a single question: "What are some of the seemingly small changes you’ve made that have had the largest impacts?"
When taking over a new business, new CEOs often speak of operational “low hanging fruit”, so I wanted to ask this same question to 4 different CEOs to learn more about just what this low hanging fruit is.
Each CEO that I’ll be speaking with today is at a different stage of their journey: Betsy, who I’ll begin the episode with, is still in her first year in the CEO seat. Sheret, our next leader, has been CEO of his company for ~2 years. Robin Kovitz has been leading her company for ~8 years, and finally Adrian, our final CEO, ran his company for ~7 years before a successful exit to a strategic acquiror in 2019.
Does growth and success tend to result from a large number of seemingly small changes, or a small number or larger changes? That’s what we’ll endeavor to answer today, informed by 4 CEOs at very different stages of their respective journeys.
This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more.
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This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.
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CEOs running newly public companies, those who have raised external equity for the first time, and those occupying the CEO seat for the first-time are often intimidated by the idea of reporting into a Board, and are uncertain of how to construct, manage, communicate with, and learn from them. This combination of uncertainty and inexperience often creates undue stress for CEOs, and can create situations in which they are more focused on impressing their Boards than they are on leaning on them for support, guidance, and mentorship.
Over many years as a CEO reporting directly into a Board (and now as an investor who sits on Boards and works directly with CEOs myself), I’ve come to learn a few things about how to construct, manage, communicate with, and learn from this critically important group of people.
This episode is my best attempt at sharing these lessons with you.
This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more.
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This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.
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My guest today is Mike Zani, CEO of The Predictive Index. The Predictive Index serves more than 9,000 clients across 142 countries, helping businesses optimize their hiring and team composition decisions through behavioral science, software, and professional consulting from the world's top workplace behavioral specialists. Mike has been CEO of The Predictive Index for approximately 8 years, after having purchased the business from its original founders. Prior to leading The Predictive Index, Mike successfully purchased, operated, and sold two other companies in the employee wellness and manufacturing industries.
The Predictive Index is one of the most widely-used personality profiling tools utilized by SMB CEOs when making hiring decisions, and in today's discussion we discuss these types of tools at length: When they're most useful (and when they're not), the most frequent sources of hiring mistakes, how transferable they are to blue collar industries, how we might utilize them in our personal relationships, and how he would utilize similar tools if looking to buy another business, to name just a few.
Please enjoy!
This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and to the best extent possible, I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. If that doesn’t say confidence, I don’t know what does. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more.
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This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.
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This episode attempts to directly address many of the questions that I’ve been asked over the past 6 months related to the current state of the debt markets: How pricing has changed, how credit availability has evolved, what risks banks are no longer willing to underwrite, how their diligence processes have changed, how non-price terms have evolved, and so on. To help me better understand the current state of the debt markets, I reached out to Cory Kaiser and Tim Eaton, both of whom work at TD in their commercial lending group: Cory is Vice President of commercial banking and has been with TD for over 21 years, and Tim is an associate vice president, who has been with TD for 23 years. Over the past two decades, their focus has been (and will continue to be) on lending to lower-middle market private companies, not just to finance their acquisitions, but also to finance growth, working capital, and recapitalizations, to name just a few. I hope this episode helps to clarify some of the questions that you might be wrestling with yourself. Please enjoy!
This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and to the best extent possible, I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. If that doesn’t say confidence, I don’t know what does. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more.
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This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.
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Enterprise software is considered to be among the world’s best business models. However, getting access to the world’s best business model doesn’t come cheaply: Software businesses most frequently trade at multiples of recurring revenue, which stands in contrast to most other industries in which businesses tend to trade at multiples of EBITDA or cash flow.
But not all software investment theses are created equally: There are indeed several different approaches to acquiring and building a software company, and each approach presents a different investment thesis, requires different operational and value creation strategies, and is likely to command different asking prices. In today's episode, I present and evaluate 5 very different approaches that buyers might consider in their pursuit of a software business. Though this list of approaches is by no means exhaustive, it does capture those that I tend to see most frequently.
Please enjoy!
This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else.
Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.
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My guest today is Brent Beshore. Brent is Founder and CEO of Permanent Equity, a private investment firm that invests in Founder-owned private companies. Permanent Equity is a (very) long-term investor that typically intends to hold portfolio companies indefinitely, often without the use of any leverage.
In addition to his role as an investor, Brent is also a prolific writer: He is a regular contributor to Forbes, and also publishes and releases materials for free on Permanent Equity's website, spanning topics like operating, selling, and investingin SMBs, among others. Brent is also the author of The Messy Marketplace, a book that aims to demystify the process of selling a company.
I must say that this conversation was a real pleasure for me to have. Brent is a really thoughtful guy who has a lot of really unique and insightful views on buying, running, and selling SMBs. And, of all the many conversations that I’ve had recently, this one might cover the most ground: So strap in for a very wide-ranging discussion, and please enjoy.
This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else.
Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.
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In today’s episode I get unapologetically tactical, and discuss the specific tools, routines, and practices that I have found to be particularly effective in managing my own psychology as an entrepreneur and CEO. I chose to write about this topic based on the following three deeply held beliefs: (1) A CEO’s ability to manage herself is at least as important as, if not more important than, her ability to manage her business; (2) Unless you are deliberate about managing your own psychology, you risk becoming a sort of “victim” to the circumstances that happen to present themselves in your life at any given time; & (3) Over time, the mood of the broader employee base often directly reflects that of the leader.
I hope at least some of these prove to be helpful for you
This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else.
Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.
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My guest today is A.J. Wasserstein, the Eugene F. Williams, Jr. Lecturer in the Practice of Management at the Yale School of Management. His research, writing, and teaching concentrates on search funds, entrepreneurship, programmatic acquisitions, and small businesses.
In addition to his role as an educator, A.J. is also a private investor in lower middle-market businesses. He was the President of Onesource Water, the third-largest bottleless water service business in the U.S., which was sold to Water Logic, a U.K.-based strategic acquirer, in 2016. Previously, A.J. was the founder and CEO of ArchivesOne, the third largest records management company in the U.S. ArchivesOne was sold to Iron Mountain (NYSE: IRM) after 17 years of operation.
A.J.'s incredible collection of writing can be accessed here.
This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else.
Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.
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Episode Description: Relative to its importance, capital allocation seems to be a relatively under-discussed subject among SMB CEOs. The subject is at least as important as more common day-to-day issues like hiring, culture, or compensation, though it rarely seems to occupy the same share-of-mind. Though capital allocation isn't a discipline that CEOs consciously or explicitly deprioritize, it often loses the battle for their time and attention when competing with more common day-to-day issues like those mentioned above.
As a CEO you’d be wise to regularly look at your business through the lens of an investor to ensure that you’re allocating your company’s scarce financial resources towards their highest and best use. In today's episode, I discuss some relevant lessons that I’ve collected over the years related to capital allocation, some of which I hope are helpful to you.
My guests today are Steve Lau and Rameez Ansari, co-CEOs of AutoLeap, a software company that services auto repair shops, that counts Bain Capital Ventures among its investors.
Prior to founding AutoLeap, Steve and Rameez purchased, operated, and sold D'Esco (later renamed FieldEdge), a software company that helps entrepreneurs run their HVAC, Plumbing, and Electrical Contracting businesses. Steve and Rameez purchased the company from its original founder in 2015 at 5X EBITDA, when its product was entirely on-premise and its revenue was generated solely through the sale of perpetual use licenses. After successfully transitioning the company to one that sold a cloud-based product and generated revenue on a subscription basis, they sold the company to a private equity firm for 8X revenue in 2019.
For the past 5-10 years, investors have salivated over the return potential inherent in transitioning a sticky enterprise software product with low customer churn from on-premise to SaaS. Though returns like those generated by Steve and Rameez certainly illustrate that such transitions can be successfully made, the headlines often ignore how brutally difficult this transition tends to be, both operationally and financially.
Though software investors and operators will find this episode relevant for what are probably obvious reasons, I’d also suggest that any CEO, in any industry, ought to pay attention to the lessons that Steve & Rameez learned, especially if they’re considering a transformation of any sort within their own companies. We talk about shifts in organizational culture, changes in salesforce compensation, how to communicate the need for change within a company, how to respect the history and legacy of a business while still keeping an eye towards the future, how non-technical CEOs can run a technically-oriented business, and much much more.
Unfortunate at this reality may be, I would argue that firing (specifically knowing who, when, and how to fire) is a required core competency for any CEO, and is arguably as important as hiring, communication, capital allocation, and other tools within the CEO’s toolkit. The extent to which this is an unpleasant (and perhaps even unpopular) topic to discuss doesn’t negate its critical importance in building and sustaining a healthy and vibrant company.
Some may associate the idea of firing with toxic, authoritarian, or fear-based work cultures. While firing can lead to these types of outcomes if done in an arbitrary, thoughtless, or fear-inducing way, if and when done correctly, it can actually become one of the CEO’s primary tools in building a healthy, inclusive, fair and meritocratic culture.
It’s important for me to note that this isn’t because firing itself is value-creating. It clearly isn’t. Being flippant or cavalier with the professional lives of your employees represents the surest path to destroying your company. Instead, one of the primary reasons why firing is so (unfortunately) important is because of how difficult, error-prone, and subjective most hiring processes are.
Today’s episode is for anybody who ever plans to sell a company.
Most entrepreneurs will sell a business once in their entire careers (if they’re lucky), and as a result many understandably don’t have a lot of context or experience in the finer points of exiting, specifically when it comes to how to select an M&A advisor. Most advice that I’ve come across in this domain is frankly too high level to be useful, so today I wanted to get really detailed on how to select an M&A advisor, how much you should expect to pay them, what’s included & excluded from the fees that they charge, and other critical contractual terms you should be aware of before hiring one of them.
To help us answer some of these questions, I’m joined today by John Carvalho. John is the President of Stone Oak Capital, an M&A advisory firm that focuses exclusively on middle market businesses, with a specific focus on transactions between $10 and $100 million.
John is also the Founder of Divestopedia. Since its inception in 2012, Divestopedia has become THE place to go for anybody contemplating selling their company: It contains a dictionary of more than 500 M&A related terms, thousands of articles on the exit process, and is now one of the world's leading online resources for selling a mid-sized business.
In addition to his experience advising CEOs, John is also an entrepreneur himself, having co-founded Wolverine Energy Services Inc. in 2012 with an initial acquisition of a $5 million revenue oilfield services company. From the first acquisition to 2020, John and his business partner acquired 16 more businesses, grew revenue to $240 million and took the company public.
It's not hard to understand the importance of persistence to the entrepreneurial journey. Entrepreneurs who overcome substantial hardships on their eventual road to success are (rightly) applauded for the otherworldly persistence that they demonstrated in doing so.
Yet many entrepreneurs are able to finally achieve success only after moving on from several prior ventures whose prospects eventually grew to become much less promising. These entrepreneurs are also (rightly) applauded, though this time it’s for the foresight, objectivity and courage that they demonstrated in making what must have been an incredibly difficult decision to “quit”.
So, which is it? Should entrepreneurs persist at substantially any cost, or should they be wise enough to know when they’d be better off doing something else entirely? How does one know when to perceive persistence as an asset, and when to perceive it as a liability?
In late-2020, I decided to step down as the CEO of my own company after approximately 7 years at the helm. Since then, I have spoken to countless entrepreneurs and CEOs wrestling with similar decisions. In each instance, they asked how I made my decision, which is why I’ve decided to write this post.
Though I can’t tell you specifically what you should do, I can at least share with you the questions that I asked of myself in coming to my own decision.
For many business owners, few things are as exciting as receiving a Letter of Intent (“LOI”) from a prospective purchaser. Beyond the sense of validation stemming from the fact that a sophisticated counterparty sees an asset worth paying for, many business owners likely view an LOI as a just reward for decades of hard work, sacrifice, and illiquidity.
Understandable as these reactions may be, I would argue that they are premature at best, and misleading (or even incorrect) at worst.
This audio blog attempts to speak to prospective sellers of small or medium-sized businesses about what LOIs are (and more importantly, what they are not), and to review how experienced buyers may strategically utilize them as tools to further their own objectives, sometimes at the expense of those of the seller.
Today's episode is all about the finance & accounting function: My guest is Nicholas Andrews, who is the Founder of Aspen Consulting Group, a company that performs finance, accounting, and operations consulting for a wide range of small and medium sized businesses. Aspen’s services include technical accounting, corporate finance, valuations, operations planning and M&A due diligence, among others. Our conversation begins with several questions about how to manage cash and other sources of liquidity amid all of the macroeconomic volatility & uncertainty we’re currently witnessing. We then discuss the topic of employee financial literacy, including the question of how transparent CEOs should be with company financials, and then move to questions of capital allocation and how CEOs should think about spending the cash that they generate, and finally we conclude with several considerations related to hiring, specifically focusing on the question of how CEOs should think about hiring a senior finance & accounting leader, which I suspect many listeners are attempting to do for the first time. Please enjoy!
In this episode, I attempt to debunk a common misconception among prospective acquirors, particularly those looking to purchase a business for the first time. This myth states that the smaller the business in question, the easier it is to purchase and operate.
In the material that follows, I will attempt to explain why the exact opposite statement is likely true: That smaller companies are actually much harder to both purchase and operate when compared to their larger peers.
My guest today is a particularly personal and a particularly special one for me: I have been fortunate to call Jim Sharpe a mentor and friend for over 10 years now, and I am thrilled that he agreed to join the podcast. In this week's episode, we discuss the realities of running a business during high inflation environments, including the risks and opportunities that may present themselves during such times. We also discuss how CEOs should think about pricing their products and services in response to inflationary pressures, and finally how they should deal with vendors who attempt to pass through price increases to them. Jim has been at at the Harvard Business School since 2009, holding positions as a Senior Lecturer in the MBA and Executive Education programs, an Entrepreneur in Residence, and now serves as a Visiting Executive. In 1987, Jim purchased Extrusion Technology, an aluminum extrusion fabricator that he ran as CEO for over 20 years. In 2008, Jim sold the company to a private equity firm, having grown the company from $4MM to $32MM in revenue throughout his ownership tenure. Jim is now an active investor in small and medium sized businesses, holding ownership positions in more than 50 entrepreneurial companies.
In his book, The Five Temptations of a CEO, author Patrick Lencioni discusses five areas in which CEOs tend to inadvertently prioritize the wrong things. These “temptations”, as he calls them, can lead to poor decision making at best, and can risk the very survival of the company at worst. My experience leading a software company taught me that there is a sixth temptation, unique to software, that seemed to present itself on a near-daily basis. More specifically:
The biggest temptation of a software CEO is to throw bodies (specifically engineers) at problems.
It is this sixth temptation that I struggled with most frequently. With the benefit of hindsight, I’ve come to a few realizations that I’d like to share with fellow software CEOs in hopes that they’ll do a better job of managing this temptation than I did. Among other lessons, I share how the following realities should shape the decision of whether or not (and by how much) to increase the size of the company's engineering team:
- Communication channels grow non-linearly as team size increases
- Work expands to fill the time allotted for its completion
- The development team will never be big enough
- One unit of additional capacity often doesn’t produce a unit of additional output
- When CEOs add more developers, they’re often attempting to solve the wrong problem
- It’s much easier to add than it is to take away
- Hiring engineers can be a very difficult hire to quantify
Please enjoy!
My guest today is Carin-Isabel Knoop, Executive Director of the Harvard Business School Case Research & Writing Group. Carin has spent decades writing cases on managers and leaders all over the world, across a wide array of functions and industries. In 2019, alongside co-author John Quelch, she published Compassionate Management of Mental Health in the Modern Workplace, a book that dove deeply into the relationship between work life and mental well-being, and suggested in which managers can and should act as the "chief mental health officers" of their respective teams.
In today's episode, we dive deeply into the following questions and issues:
- Link between employee burnout and turnover
- Signs for leaders to look for that may be predictive of turnover
- Prevention strategies, for both the CEO and her employees
- Can CEOs maintain “high performance cultures” while simultaneously managing the risk of employee burnout?
- How to detect emotional depletion within yourself
- Personality traits that are positively correlated with burnout risk
- Separating your own sense of happiness from the success of your business at any given time
- How acquirors of businesses can and should perform due diligence on the employee base that they're acquiring
Please enjoy!
Today's episode is aimed towards those who may be wrestling with the question of whether or not to finally pursue their entrepreneurial dreams. I walk you through how I made this decision myself in 2012, and also attempt to compliment those considerations with some of the lessons and reflections that I’ve garnered in the 10 years since then, which of course benefit from the clarity that only seems to come with hindsight. Whether or not to take the entrepreneurial plunge is a deeply personal question, and as a result no objectively correct answer exists to address it. What I argue in this episode however is that the answer itself will only be as good as the introspection, thought processes, and clarity of insights that led to it in the first place. Entrepreneurship is generally much less risky than most might think, though it is also significantly less glamorous than its depiction in most forms of media today. Though most people understandably focus on the risk of walking the entrepreneurial path, it’s equally important to acknowledge of risks of not doing so. Please enjoy!
In this week's episode, we discuss the importance of having difficult conversations, something that CEOs find themselves doing on a near-daily basis. We discuss three primary types of difficult conversations, including a) Hard conversations around internal company dynamics (eg: terminations); b) Hard conversations about dynamics external to the company (eg: politics); & c) Difficult conversations that CEOs must sometimes have with themselves (eg: how and when to ask for help).
This is a particularly special episode of In The Trenches for a number of reasons, including:
- It is our first ever video podcast! (Video available only through Spotify, however)
- This is our first ever episode featuring a panel discussion, including myself and a panel of four SMB CEOs, investors and Board members
- This episode is a recording of a session that I moderated during the 2022 MIT Sloan Search Fund Summit, hosted by the ETA@MIT club
Please enjoy!
My experience as a CEO taught me that the most important skill for any leader to possess is that of clear and effective communication. Indeed, a CEO’s strategy is only as good as her ability to communicate it. Though some of the basic tenets of effective communication are obvious and intuitive, others are less so. My experience leading a company over many years illustrated that good organizational communication often went well beyond the basics. In this episode, I will share with you some of the most important lessons that I learned about effective communication within my own company, including if, how & when to communicate around terminations, financial results, good news, bad news, and many others. Please enjoy!
My guest today is Chris Hutchinson, a Partner in Ernst & Young's Transaction Advisory Services Group. Chris has over 15 years of experience advising clients on M&A, financings, valuation projects, and due diligence mandates, with a specific focus on private lower-middle-market businesses. Chris and his team have completed an untold number of Quality of Earnings ("QofE") mandates spanning countless industries, including software, technology, business services, distribution, and retail, among others. Chris and I discuss what a QofE is, why it's necessary, and common trends and themes that buyers should look out for. We also discuss the working capital adjustment: What it is, why it's necessary, and common pitfalls for both buyers and sellers to avoid. Please enjoy!
Among the myriad variables that must be carefully considered when acquiring a business is the question of how the acquisition is going to be financed. In today's episode, I will provide you with an overview of the specific lessons that I learned when financing my own acquisition in 2014. I begin by discussing the critical importance of the link between capital structure and strategy, and then discuss more specific lessons learned in raising the debt required to finance the acquisition. Please enjoy!
Though Aaron Ross wears many hats, he is perhaps best known for co-authoring the global best seller Predictable Revenue, often referred to as “The Sales Bible of Silicon Valley,” which details an outbound prospecting system that’s created more than $1 billion across Salesforce.com and other companies. Most recently, Aaron published From Impossible to Inevitable, a book co-written alongside Jason Lemkin (serial tech entrepreneur, venture capitalist, and founder of SaaStr.com, the world’s #1 resource for SaaS entrepreneurs), which is a "hypergrowth playbook" based on the successes of companies like Twilio, HubSpot, Marketo, and Salesforce.com.
In addition to being a sales advisor, board member, and highly sought after public speaker, Aaron also authors his own substack page, Fresh Air, where he focuses on the personal aspects of being a senior executive, including how to best manage anxiety, exhaustion, and stress, all of which are par for the course for substantially all entrepreneurs and CEOs.
The role of spouse to an entrepreneur or CEO is not an easy one, as they are directly impacted by the emotional high and lows that are typical of the journey: They act as a source of consolation during the bad times, keep us grounded during the good times, and in many cases play a large (though often unnoticed and under-appreciated) role in our ultimate successes and failures. In spite of the importance of the role that spouses play however, the role of a spouse or partner in the entrepreneurial journey is a very under-discussed topic, at least within the literature that I'm aware of. In today's episode, I attempt to shine a light on the role that spouses play in the entrepreneurial journey from the perspective of both the spouse and the entrepreneur: I do this by discussing my own experiences, as well as presenting the results of two anonymous surveys, one of which was sent to a group of entrepreneurs and CEOs, and one of which was sent to their spouses. If you're an entrepreneur or CEO, I encourage you to please share this episode with your spouse!
My guest today is Bob Pritchett, and I’m really excited to be sharing this episode with you. Bob first came on my radar when I read his book titled “Fire Someone Today”, which was published in 2006. Right before I purchased my first software company, one of my investors and mentors purchased the book for me as a gift, and promised me that, in spite of the fact that I had likely never heard of the book, it was full of countless gems for entrepreneurs and CEOs running SMBs. And he was right: Fire Someone today remains one of my favorite all-time business books, partially because of how it was written: Usefulness, practicality, and tactical/actionable advice take the place of the theory and anecdotes that unfortunately populate many other business books that often feel like they were written inside of an ivory tower. Bob is not just an author: He’s also a Founder, lifetime entrepreneur and CEO: Bob founded Logos Research Systems (later Logos Bible Software and now Faithlife) in 1992, and acted as its CEO for 30 years, until recently assuming the role of Executive Chairman. During Bob's tenure, Faithlife has grown both organically and inorganically from two employees to over 500, with the company now serving thousands of customers across 170 countries worldwide. Bob was a also recipient of E& Y's Entrepreneur of the Year Award in 2005. In our conversation today, we discuss how one falls into the bible software business, the merits and risks of pursuing an entrepreneurial venture with a partner, why many business partnerships fail, how much you should actually listen to your customers, what functions to inhouse versus outsource, and the practices and routines that he’s implemented to help him sustain 30 years as an entrepreneur. Enjoy!
The Working Capital Adjustment is part of substantially every M&A transaction, yet it is the calculation (and concept) with which most business owners remain largely unfamiliar. Without a proper understanding of what the working capital adjustment is, why it's necessary, and ways in which it can be manipulated, business owners risk leaving a lot of money on the table when dealing with a more sophisticated and experienced counterpart (even AFTER the sale of their business is already complete).
If you don't like the idea of having to wire money back to your buyer after they've wired you the money to purchase your company, then this episode is for you.
Today’s episode is all about Hiring, and we’ve managed to secure one of the world’s foremost experts on the subject.
My guest is Randy Street. Randy is Vice Chairman of ghSMART, which is a global consulting firm that helps CEOs, boards, and investors build valuable companies specifically through hiring and developing world class leadership teams. During Randy's tenure, ghSMART has grown tenfold, and has been ranked by Forbes as one of America’s Best Consulting Firms from 2017-2020.
Randy first came on my radar when I read the book that he wrote in collaboration with ghSMART’s chairman and founder, Geoff Smart, called Who: The A Method for Hiring. I profile this book on my website as being absolutely required reading for all entrepreneurs and CEOs running SMBs. The very specific hiring method that they detail within this book changed the way that I made all of my hires across my entire company.
The book quickly become a New York Times, Wall Street Journal, BusinessWeek, USA Today, and Publishers Weekly best seller, and has earned acclaim from countless other publications. Randy also co-authored another Wall Street Journal bestseller, called Power Score: Your Formula for Leadership Success.
In our discussion today, we barely touch on Randy’s book because, candidly, I’d encourage you to simply buy it an read it for yourself. In today’s episode, I try to dig one level deeper with Randy and discuss how to evaluate people & teams that you haven’t personally hired, post-hire considerations, lessons from 30+ years of working with CEOs and management teams, compensation, and how to identify and address conflicts within leadership teams.
Please enjoy!
In today's episode, I discuss the signs that prospective acquirors should look out for when attempting to uncover how much “technical debt” any given target company may possess within their code base. Though substantially every software company has some amount of technical debt, those that are weighed down by an asymmetric burden of it tend to ship code less frequently, struggle to keep pace with competitors, regularly miss release targets, and are generally much more expensive and capital intensive to operate and grow. In this way, what start out as technical problems quickly accumulate to become significant business problems. Thus, prospective acquirors would be well served to thoroughly diligence the amount of technical debt possessed by any given target company, and proceed very carefully (or perhaps not proceed at all) with those companies who seem to possess much more than their fair share of it. We break our analysis down into high risk, medium risk, and low risk signs. Enjoy!
Verne Harnish quite literally wrote the book (or, in his case, books), on being an entrepreneur and CEO running a small to medium sized business. Verne is the founder of the world-renowned Entrepreneurs’ Organization ("EO"), a global network of entrepreneurs and CEOs that boasts over 16,000 members worldwide. For the past 15 years, Verne has chaired EO’s premiere CEO program, the “Birthing of Giants” held at MIT, a program in which he still teaches today. Verne is also the Founder and CEO of Scaling Up, a global executive education and coaching company with over 200 partners on six continents. Verne may be best known for being the author of multiple global bestselling books including Mastering the Rockefeller Habits; The Greatest Business Decisions of All Time (for which Jim Collins wrote the foreword); Scaling Up (Rockefeller Habits 2.0) (which has been translated into 23 languages and has won eight major international book awards including the prestigious International Book Award for Best General Business book); and his latest book, Scaling Up Compensation. In our chat today we cover a wide range of topics starting with compensation, and then moving to hiring, managing one’s self, and a bit of a mixed bag at the end. We also conclude with the 3-5 books that Verne would put on his Mount Rushmore of business books, so if you’re a reader, be sure to stay tuned for that one.
Throughout recent history, there has been substantial growth in the number of companies who have decided to implement formal “operating systems” to govern certain strategic and operational decisions within their businesses. Though there are many operating systems in existence today, two of the most widely used systems are EOS (based on the book Traction, by Gino Wickman) and The Rockefeller Habits (based on the books Mastering the Rockefeller Habits and Scaling Up, both by Verne Harnish). I implemented an operating system (EOS) in my own company beginning in 2015, and we continued to operate under its various principles and structures until successfully selling the company in late 2020. Though a formal operating system likely isn’t appropriate for all companies and all circumstances, we benefited tremendously from our own implementation. Based on that first-hand experience, in today's audio blog I share a number of FAQs that I often receive from other CEOs related to the implementation of a formal operating system within a SMB.
Today’s show is all about GROWTH. Specifically, I want to dig into the personal and professional realities of running a high growth company that often aren't terribly visible from the outside looking in. Today, I talk to Anthemos Georgiades (or Anth, for short), who is the founder and CEO of Zumper, an apartment rental platform based out of San Francisco. If anybody knows about running a rapidly growing company, it’s Anth. Consider this: Despite being founded less than 10 years ago in 2012, Zumper now boasts over 250 employees and 75 million active users, making it the biggest residential rental platform in North America. Since founding Zumper, Anth has raised over $150M in Venture Capital funds from a roster of VCs that would likely make many of his Silicon Valley CEO peers envious, including Andreessen Horowitz, Greylock, Kleiner Perkins, and Blackstone, among others. Since its founding, Zumper has regularly grown at triple-digit growth rates, which of course has presented Anth with both problems and opportunities that some CEOs simply haven’t had to deal with. Among other things, in our discussion today we talk about the tradeoff between raising growth capital and dilution of his personal ownership stake, how he thinks about how much money to raise at any given time, his views on organic versus inorganic growth (and his experience managing both), the systems and processes that often break in the face of high growth, how growth has impacted his hiring and retention strategies, and lastly how managing an ultra-high growth company has impacted Anth personally. If you run a company that is growing at any pace, I hope and trust that you’ll leave with at least a few nuggets of wisdom that will help you along your own journey.
Acquiring any business is hard. Acquiring a software company is no exception, and indeed may prove to be even more intimidating to the inexperienced acquiror due to certain non-obvious considerations unique to software companies and the business models under which they operate. In this audio blog, I explore several of these unique and non-obvious considerations for the prospective software acquiror to consider based on my own experience acquiring, running, and selling a small- to medium-sized software company over the course of many years. Specifically, for every topic that I profile, I discuss why it’s important to dig one level deeper than the simple “headline” numbers or conclusions. In this audio blog I will discuss only financial considerations, while in my next episode, I will discuss non-financial considerations. Enjoy!
Today's episode is all about the legal issues and considerations involved in selling a small to medium sized business ("SMB"), many of which tend to be unfamiliar to CEOs and Entrepreneurs.
My guest, Mario Nigro, is one of Canada's preeminent M&A lawyers, and currently serves as a Partner in the Mergers & Acquisitions and Private Equity & Venture Capital Groups at Stikeman Elliot based out of Toronto. From a legal standpoint, Mario has worked with substantially every type of stakeholder within the SMB ecosystem (business owners, CEOs, entrepreneurs, strategic acquirers, private equity firms, banks, non-bank lenders, financial advisors, deal intermediaries, and so on), and regularly acts for both buyers and sellers in both minority and majority SMB sales.
We cover a lot of ground in our discussion, and focus specifically on the most common blind spots that Entrepreneurs and CEOs tend to exhibit when it comes to selling their companies, including:
The most common reason why entrepreneurs over-pay in taxes after receiving their deal proceeds;
How to select legal counsel when looking to sell your business, and how much you should expect it to cost;
Whether LOIs should be detailed or generic, and why;
The circumstances under which buyers and sellers would prefer an asset sale or a share sale;
The most frequent mistakes business owners make when negotiating representations & warranties in the purchase agreement;
Why rep & warranty insurance is growing as a useful tool for both buyers and sellers;
How to deal with unsophisticated legal counsel & advisors in a SMB sale;
The top 3 reasons why deals fall apart after a LOI is signed;
How to negotiate your non-compete;
You can access the show notes by clicking on this link
Please enjoy!
In January, 2014, I became the CEO of a software company (after having acquired it from its original founders), powered by all of the wisdom and experience that one would expect from a 27-year-old who had never managed as much as a fruit stand in his entire life. The pace was intense, the volume of information to be processed was overwhelming, and the lessons learned were numerous. In this audio blog, with the benefit of 10 years' worth of hindsight and perspective, I attempt to share with you some of the major lessons and observations gleaned from my few months as the CEO of a newly acquired small business, in hopes that you can utilize some of them should you ever find yourself in a similar situation.
My guest today is Rich Manders, who has essentially done everything that a CEO and Entrepreneur can do: He has founded companies, operated and grown them substantially, sold them (several times), acquired them (several times), and now acts as a coach for other CEOs and Entrepreneurs looking to do the same.
Rich Co-Founded and led iAutomation, a Massachusetts-based machine control and automation company, and grew the company from $0 to $90M in sales with 180 employees. After selling that business to The Riverside Company (a leading global Private Equity firm), Rich stayed on with the business, and alongside his partners at Riverside, he grew the company by a factor of 6x, resulting in a 50%+ IRR to his original investors after its next sale to Saw Mill Capital.
Alongside Riverside, Rich has played a key role in seven completed acquisitions and has evaluated dozens of others from the perspective of both a buyer and a seller. Rich has Board experience across several different private companies, and alongside his business partner, now runs Freescale Coaching, where he coaches entrepreneurs and CEOs and helps them grow their business beyond their wildest dreams.
Rich’s entrepreneurial success story is the subject of a Harvard Business School case study, which is where I was first introduced to him in my second year of study there. Since then, Rich has taught several courses and seminars at Harvard, among other leading business schools. He relies on his decades of experience as an Entrepreneur and CEO to inform his structured, systematic, repeatable, and process-oriented approach to growing world-class private companies.
Please enjoy!
Early in my tenure as a CEO, I thought core values were tired, hollow, and meaningless platitudes that companies created simply because they felt they had to. Many of you may view them in a similar light. What I came to learn over time however was that my skepticism towards core values wasn’t because the CONCEPT of them was hollow and meaningless, but instead because so many companies had done such a poor job in establishing theirs, and as a result, their core values BECAMEtired platitudes that nobody paid attention to.
We eventually came to view our core values as a small set of vital and timeless guiding principles for our company, that defined our culture and our people, both as individuals and as a team. We used them to add a sense of clarity to everything that we did within our organization, including to attract like-minded people, to reward, recognize and appreciate existing employees, and to make more objective hiring, promotional and other personnel-related decisions.
If your company doesn't currently have any core values established, (or you do, and they're lacking any real world impact), then this episode is for you. I discuss several of the primary lessons that we learned over the years to make our values truly meaningful.
Today’s episode is specific to software companies, and is all about the Product Management operation. As most software executives can attest to, a non-functioning (or worse, a non-existent) product management operation can get companies into all kinds of trouble, and those problems often manifest across Engineering, Sales, Customer Support, and other areas. Some software companies, particularly more mature ones, often start out without a formalized product management discipline, but companies who pursue any degree of scale often quickly realize just how critically important this discipline is.
My guest today is Rich Mironov, who is one of North America's preeminent Product Management thought leaders. He has spent 40 years in the software industry in numerous capacities, and currently acts as a Coach, Consultant, and Interim Executive for CEOs and Heads of Product across Canada and the United States, advising them on a diverse range of issues spanning product, marketing, engineering, and sales. Rich has led Product Management at six start-ups, and has now consulted for more than 170 technology companies of all sizes. He is the author of "Product Bytes", a hugely popular and long-running blog on software, start-ups, product strategies, Silicon Valley, and the inner life of product managers. Rich is also the author of the book, “The Art of Product Management”.
Our conversation covers a lot of ground including hiring a Product leader and Product team, how to think about prioritizing products/features/functions, how Product should interface with Sales and other internal departments, how involved CEOs should be in Product, and what fatal mistakes he’s seen Product Managers make. Please enjoy!
As a business owner, if you're thinking about the sale of your company as being the singular event that will finally eliminate all of the risks that you've personally assumed for so many years, then I hate to be the one to tell you this, but: Think again. Indeed, in my experience, the single biggest myth about selling a company is that the seller bears no further risk after the sale of his or her company is completed. In most cases, especially with respect to the sale of SMBs, this is simply not true. In this audio blog, I will share with you some of the more common ways in which sellers may still bear some risk (in some cases, material risk) even after the consummation of the sale transaction. Though this list isn’t an exhaustive one, you should expect to encounter at least some of these sources of risk when the time comes time for you to sell your own business, so it’s worth educating yourself on them from now. As it relates to certain of these risks, I also share certain tools and strategies to eliminate or mitigate these risks as best as possible.
In today's episode, I speak with Dr. Eliana Cohen, a Clinical Psychologist who works with (among others) a wide variety of Entrepreneurs and CEOs. Dr. Cohen's practice integrates performance psychology, strategy, emotional intelligence, and knowledge of neuroplasticity and the brain to serve her various clients. In our discussion, we cover a lot of ground including the psychological similarities that Entrepreneurs and CEOs tend to present, how to differentiate between healthy and unhealthy levels of worry and/or anxiety, how leaders tend to conflate their own happiness with the success of their businesses, signs to watch that may suggest that mental health is suffering, how to find a therapist, books to read, and much more. Please enjoy!
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If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated
Ben Horowitz, the former CEO of Opsware and now world-renowned Venture Capitalist, once said: “By far the most difficult skill for me to learn as CEO was the ability to manage my own psychology . . . very few people talk about it . . . In the end, this is the most personal and important battle that any CEO will face.”
I suspect that almost all entrepreneurs and CEOs know exactly what he meant when he said this. My own experience taught me that unless you are deliberate about managing your own psychology as a leader, you risk becoming a sort of “victim” to the circumstances that happen to present themselves in your life at any given time.
Against this backdrop, in this audio blog I share the five most meaningful lessons that I’ve learned over the years related to better managing my own psychology as a leader. Though many of these lessons are easier said than done, I suspect that any degree of time and effort that you dedicate towards them will likely yield meaningful results. They include 1) The perils of comparing ourselves to others, 2) Focusing only on what you can control, 3) The value of better understanding yourself, 4) The price of untethered levels of ambition, and 5) How to deal with "first world" problems.
Though mastery of these subjects is something that will likely elude all of us, improvement is probably much easier to attain than you may think.
If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
In this episode I interview Warren Coughlin, who has been a Coach to SMB CEOs for upwards of two decades, helping them achieve everything from hugely successful exits, to 7-figure salaries, to significantly reduced day-to-day operational roles, and countless other outcomes.
Warren is the creator of The Business That Matters Playbook, a tool that streamlines and automates the strategic planning process for CEOs and Entrepreneurs. His coaching practice focuses not only on the business itself, but also on the entrepreneur at a personal level, working with them to ensure that they craft meaningful values and live a lifestyle that is meaningful and fulfilling to them.
In this episode we cover a wide array of topics, some of which include: What do CEO coaches actually do? What does a typical coaching engagement look like? When is an appropriate time to hire a coach, if you hire one at all? How much do coaches cost, and how should CEOs think about the ROI on that investment? How does one even go about looking for a coach? How much of the coaching process is focused on the business vs. on the entrepreneur themselves? What are some of the most common areas for improvement that you witness when first engaging with a new CEO client? When should you fire your CEO coach? And countless others.
Please enjoy!
If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
In Part 1 of this Audio Blog, we evaluated some of the more common challenges that companies face when attempting to migrate both their product and revenue models from that of on-premise to SaaS. I guided my own company through this transition over many years. Though we did end up achieving some success, our transition ultimately went too slow, required too much time and capital, and came in below our initial targets. In this Audio Blog (Part 2), I leverage this first-hand experience to walk you through the tactics and strategies that you can put into place to make your own transition faster, cheaper, and ultimately less painful than mine was. These include things that we did (that worked), as well as things that we didn’t do (that I wish we had). Enjoy!
If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
As CEOs, many of you are undoubtedly considering the possibility of selling your business at some point in the future.
In 2018, I attempted to sell my own business, though was unsuccessful in doing so. From start to finish, the sale process took upwards of 12 grueling months. Hundreds of potential suitors were narrowed down to a dozen or so, which in turn were narrowed down to a single acquiror with whom we completed the extensive financial, legal, technical, and commercial due diligence process.
Just as we were beginning to draft the final purchase agreement, the transaction fell apart. At the time, this felt like a big personal failure. I felt as if I had spent a full calendar year pushing myself to the brink of exhaustion with nothing to show for my efforts. With the benefit of time however, I’ve come to realize how enormously valuable this experience was. Indeed, without the knowledge and experience that we had acquired, we almost certainly would not have successfully sold the business in 2020.
In this Audio Blog, I share with you some of the major lessons that I learned during my first (unsuccessful) attempt at selling my company. I hope you’ll find them to be useful.
If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
As CEOs & Entrepreneurs, I suspect many of you have at least considered the possibility of an exit, whether it be in the near or long-term future. In my experience selling my own business, the selection of my M&A Advisor was perhaps one of the most important decisions that I had to make, and in retrospect so many other decisions (and their outcomes) flowed directly from this one critical choice. I once chose a bad advisor, and have since worked with a great one.
Based on these experiences, I have an enhanced appreciation for the specific variables that I think are important to consider when making this critical decision.
Today’s Audio Blog explains each variable that I think you should consider in selecting your own M&A Advisor, in hopes that you will be able to benefit from my lessons without having to experience the heartache that led to them in the first place!
If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
As CEOs & Entrepreneurs, we all know that there are a countless number of levers that one can pull to grow revenue or profitability, all of which will have varying degrees of impact. Increasing prices is one such lever, however it is somewhat unique. In this audio blog, I explain why.
I argue that in certain circumstances, raising the prices that you charge to existing customers is one of the fastest, most effective, and “lowest friction” ways to unlock a nascent revenue and profitability opportunity that may reside within the base of customers that you already possess.
It isn’t the right strategy for all companies, but it almost certainly is for some. If you haven’t revisited your pricing in 1-2+ years, then there’s at least a possibility that incremental revenue and profitability are being left on the table.
Though this Audio Blog does touch specifically on software companies at times, it's important to note that the insights contained within can be applicable to substantially any business that engages in repeat sales with existing customers, be it within a subscription revenue model or not.
If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
My guest today is Jordan Bettman. Jordan is a Partner and Co-founder of Radian Capital, a New York-based Private Equity firm focused on B2B software and technology-enabled services businesses. Radian currently has ~$500 million of assets under management, and is now investing out of their second fund.
Prior to co-founding Radian, Jordan was a Partner at Bain Capital Ventures for nearly a decade, where he focused largely on financial services and back-office technology investments. He currently serves on the Board of Directors of 5 private technology businesses, and through Radian has made direct investments (both majority and minority) in dozens more.
Jordan received his MBA from Harvard Business School and his B.S. from Cornell University.
Jordan & I discuss a wide range of topics (some specific to software, others around M&A more broadly), including how he evaluates software companies, how CEOs should evaluate potential acquirors, the pros and cons to CEOs of selling in a sellers' market, why deals fail, how to best align interests of buyers and sellers, and expectations of CEOs after they sell their company.
Please enjoy!
If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
Today’s audio blog is specific to software, and concerns the migration from i) a business model characterized by on-premise hosting and one-time perpetual-use licensing fees, to ii) a new business model characterized by cloud-based hosting and a subscription licensing. This process is generally referred to as the "On-Premise to SaaS Migration".
Most software companies founded over the past fifteen years or so have never known anything other than the latter model, however, for anybody running a company still selling on-premise software under a perpetual-use pricing model (or is considering investing in one) , I'd humbly suggest that you listen to this episode.
In this post, I lean on my first-hand experience in making this transition to describe some of the factors that make it so difficult. In my next post, I will share with you the tactics and strategies that worked (and didn’t work) for me to overcome some of these challenges, so that you can drastically increase your own odds of success should you decide to make this leap yourself.
Enjoy!
If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
In my experience as a CEO, I came to learn that surrounding myself with A+ people (particularly at the senior leadership team level) was one of the most impactful things that I could do for both myself and my company. Even if you are above average with respect to your ability to hire great people (most people think that they are – yet most people are not), it is a virtual guarantee that you'll make some mistakes as you build out your leadership team.
I certainly did. It took me many years (and many mistakes) to learn about great hiring practices. To prevent you from making some of those same mistakes, in this Audio Blog I’ve compiled a list of the major lessons that I learned while hiring my own executive team over many years.
Enjoy!
If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
Today’s episode is all about execution, and more specifically what you need to do to give yourself the best odds of actually executing on the goals that you set for your organization.
There’s a well-known maxim that you might be familiar with that states “Strategy without execution is hallucination”, and in today’s audio blog I’ll share with you why I think that’s true. I’ll do so by sharing some of the lessons that I’ve learned over the years related to executing on the strategy you set. In my experience (and in the experience of countless others), strategy is actually the easy part: Almost any mediocre CEO can set logical and compelling goals for a company, but it’s the truly skilled CEO who adjusts her tools, systems and processes to regularly and successfully execute on those same goals.
As Jim Collins and Jerry Porras (authors of the seminal business book Built to Last) said: “Building a visionary company requires one percent vision and 99 percent alignment.” Today, I’ll share with you the best tools that I’m aware of to create that alignment.
I hope you enjoy!
If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
In today's post, I share with you the lessons I’ve learned to deal with (or prevent, as much as possible) the mental health toll that entrepreneurship (or leadership, or success) can take: Of course, these lessons are only now clear to me with the benefit of hindsight vision being of the 20/20 variety. When you’re constantly in the trenches, like so many Entrepreneurs and CEOs are, it’s difficult to see the forest from the trees. For this reason, I hope you’ll find this Audio Blog to be highly practical, and full of strategies that you can actually employ in your own day-to-day life.
If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
In this Audio Blog, I provide you with a brief summary of my own mental health journey as a leader. My goal isn’t to provide you with an exhaustive account of my journey, but rather to simply discuss it publicly. After all, if I don’t do my own part to contribute to the discussion around the worries, thoughts, and fears that Entrepreneurs and CEOs face, what right do I have to lament that it isn’t being discussed enough more broadly? This will be my only Audio Blog solely about me. Though it may be less practical for you than other posts, I hope you’ll agree that it’s still worth listening to nonetheless. Perhaps you will see some of yourself in the feelings, worries, and anxieties that I experienced.
If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
In this episode I interview Dave Prusinksi, currently the Chief Revenue Officer at SafeAI, a hyper-growth silicon valley company in the autonomous vehicle space. Here is why I think Dave is a person worth listening to:
Prior to his current role, Dave spent 10 years as the Executive Vice President of Sales and Marketing at FleetComplete, a technology provider to fleet-owning businesses around the world. Under Dave's leadership, FleetComplete grew from $6M ARR to $150M in total revenue, achieving an average 50% revenue CAGR for 9 of his 10 years.
Dave played an integral role in the acquisition of 6 companies, leading the sales and marketing due diligence processes, and ultimately integrating the operations of the acquired businesses into that of FleetComplete.
In addition to acquiring and investing in SMBs for FleetComplete, Dave was also a central member of the deal team helping to lead FleetComplete through multiple investment and acquisition rounds themselves, managing the sales & marketing due diligence processes in each instance.
Dave has served as a Revenue Coach to several SMBs, working directly with their CEOs and Heads of Sales to optimize their sales and revenue generation processes. All of the companies with whom Dave has worked thus far have now exited with great success.
Prior to FleetComplete, Dave was the National Sales Manager at Research in Motion, where he jointly grew and managed one of the largest divisions with over $1B dollars in annual revenue.
Dave and I cover a wide range of topics specific to sales, including: Hiring and onboarding sales leaders and individual reps, how to best craft incentive compensation plans, how to manage team attrition, how and when to build out other internal functions that support the Sales team, how and when to scale a team via additional headcount, and what sales metrics he thinks are most important for CEOs to keep their eyes on.
Please enjoy!