I Make a Living - SoundSage

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Alli Webb was always interested in beauty, starting from her roots as a curly-haired kid growing up in South Florida. She says that going to beauty school was “one of the best decisions I ever made,” and Drybar, her ultra-popular chain of hairstyling studios, definitely proves her point. While she says she spent her childhood as a people-pleaser—”a wallflower, if I’m honest”—she’s grown into herself as a business owner and service expert.

Alli spent her 20s in New York City, doing PR and styling hair until she met her ex-husband and pivoted to the stay-at-home-mom gig. “I thought it was the coolest thing ever: I get not to work? I thought I had hit the jackpot!” But after a half-decade of staying home with her two sons, she was bored. So she launched a mobile business called Straight At Home, pitching her blowouts on parental message boards and bringing a luxury that had been previously reserved for the glitterati to moms all over L.A.

She quickly learned that her business model—which included paying for a babysitter and a lot of gas money—was barely breaking even. But when she tried to pull back, she found that her service wasn’t really available anywhere else; her clients would either skip the little luxury, or they would make do at an all-purpose salon that got the job done but lacked that special touch. She envisioned a hair salon that got straight to where the magic happens: those final moments of a haircut that really put the oomph in the style. From that vision came Drybar.

Instinctively, she knew that she wanted the Drybar experience to be predictable for clients, replicating the same style and services across the country. She even provided the salon tools, bucking the industry norm that stylists provide their own. “Aesthetically, I had this idea of what I wanted, which led to knowing that, whenever you go to a Drybar, you have the same experience.” This meant that clients could trust whoever was doing their styling, no matter what shop they were visiting.

In the early days, clients pushed for Alli to expand her services. They asked for manicures and makeup services, and while Alli considered it, she ultimately decided against it. “We do one thing, and we do it really, really well.” Then, investors looked at her client volume and said they were crazy not to offer them more products, more services, more everything. Alli’s response? “I don’t want to.” To this day, Drybar offers a limited range of services that focus on great hairstyles, and they’ve grown to 150 shops nationwide.

That doesn’t mean she never expanded her business. From the beginning, Alli wanted to develop a line of harmonized hair products that would all work together. So when she raised her first round of funding, she ensured that, while the stores remained the focus, some of the money was earmarked for hair products. Her first partnership, with Sephora, helped launch Drybar from a place women went to something they could use in their daily life.

Alli’s gone on to launch other exciting brands, including Okay Humans, focusing on a “modernized talk therapy experience,” and Squeeze, a massage studio that is her brother’s passion project. Alli says that her own divorce and a chance meeting with a newly licensed family therapist inspired her to “create an experience around talk therapy.” She’s gone on to take an advisor-investor role with The Feel-Good Company, a collection of businesses aimed at making clients feel, you know, good. (She also helped launch the jewelry line Becket + Quill, proving that self-care comes in many forms.) While each business focuses on a single element of personal care, the Feel-Good umbrella takes care of HR, marketing, and other needs.

This is our final episode of season four of I Make A Living, but don’t worry—we’ll be back soon with more stories of successful entrepreneurs and amazing business advice. We love to hear from you, so keep in touch on Instagram and Facebook and, and don’t forget to check out FreshBooks, the accounting software that’s perfect for small business owners like you!

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If your memories of ice cream are mostly from childhood, Natasha Case would like a word. Her company, Coolhaus, is bringing sweet icy desserts into the millennial mindset: she launched at Coachella back in 2009, and Coolhaus’s 2021 lineup includes mouth-watering flavours like cereal milk, cannoli, and churros, all delivered in cute illustrated packaging.

Before she even got started, Natasha wanted to “change the game” when it came to ice cream and who it was for. Freya, Natasha’s wife and co-founder, is a woman of colour, and they were both tapping their identities as queer women and millennials. “We saw this opportunity to be pioneering,” she says. Without much food experience—Natasha was fired from her one and only catering gig—they launched into the ice cream business headfirst, convinced that if they didn’t shoot their shot, someone else would. “The recession had just hit, it was just way too risky.” Their first “ice cream truck” was a “barely driveable” former postal vehicle they had towed (!!) to 2009 Coachella. Since the truck was more set dressing than operable business location, they gamely set up a tent beside it, and started serving.

Natasha knew that Coachella’s crowd was who they wanted to focus on as their core audience: millennial, highly influenced by the desert heat and music fest vibe, armed with expendable income, and in a heightened state where “you might be buying a lot of ice cream and eating all of it.” For Natasha, she wanted to connect her product with people’s memories of their Coachella experience.

Natasha and Freya started with a minimum-viable-product mentality, and knew that if Coolhaus flopped, it would be a fun experiment, not a financial catastrophe. They planned for a little bit of success—a website with some pictures, a Twitter handle, a logo, and they filed the business through LegalZoom (which turned around and named a conference room after them a few years later). Their low profile during the early days gave Natasha permission not to strive for perfection, but switch it up when something wasn’t working. “We are the audience, so we asked if this was something that we wanted.”

After Coachella, they an exposure boost from CurbedLA, which highlighted their “weird flavours and “strange puns,” and helped get them to the next level: they gained more than ten thousand Twitter followers in the span of hours, and got requests from media outlets like Eater and Dwell. “You can’t plan for that,” Natasha says. “You can’t plan to go viral.” She and Freya had to make a decision: were they going to do this thing for real?

They were. “We immediately got the truck fixed so it could drive,” she laughs. They focused on both street sales and catering, and their first catering customer was MySpace. Initially, they had forecast for more sales through the truck, but within a few months, the catering business was the primary component. “That was the problem we ended up solving.” Now, 95% of their truck business is through private catering, and they have two brick-and-mortar stores in Los Angeles.

Natasha has been both a Disney Imagineer and an architect; add in ice cream, and she’s created “farchitecture.” She says it’s “food plus architecture,” a riff on her college professor’s criticism of a project that he said looked like a layer cake; her response was to bake her next model. Food and spaces are her “two passions,” and bringing them together to build special, memorable moments was not a business at first but a “passionate hobby.” Her experience at Disney helped her see how this outlook could be transformed into something more entrepreneurial: “I learned a lot from that experience.” But her “farchitecture” idea did get off the ground during her Disney days: while 2008’s recession was unfolding, she started making ice cream sandwiches to “lighten the mood” for her colleagues.

Her future wife and business partner thought the sandwiches were an amazing, quirky idea, and they’ve been together since the earliest days of the company. Navigating both business and romance in the early days was romantic—they were travelling to weddings in Ojai!—but being together all the time also supercharged Coolhaus’s operations. While things haven’t always been smooth (“Freya and I have very different management styles”), things have generally been great. “I mean, yeah, spoiler alert: we’re married and have two kids. Things worked out.”

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Chances are that your entrepreneurial idols were born after the turn of the millennium, but Ben Towers is here to change that. He’s been working since before his twelfth birthday, getting his start on web design projects for friends and family before launching into the stratosphere: we’re talking British Royal Family, angel investment, and consultancies with companies like GSK and IHG. In 2015, he was named to The Time’s Superteens list, and since then, he’s only gotten more polished in his business practices. He’s 22, and he’s been in business for half his life.

Ben has a passion for tech – he was the kid in primary school who would “be taking apart the printers,” and at a young age, he was tapped by a family friend to build her website. He brought some previous experience to the job, and filled in the gaps by watching YouTube tutorials on things like how to add contact forms. He netted himself $50 and was super jazzed. Like many youthful entrepreneurs, his first expenditure was candy. But he’d caught the bug. He freelanced for most of his teens, ultimately selling his digital agency Towers Design to Zest The Agency in 2017: a buyout before legal drinking age.

Growing the company meant growing out of his “craft,” which was coding, and into management and leadership. He stayed engaged in the work by allowing himself to sit in on client creative sessions, giving him a bird’s eye view and input in the creative ideation, without getting caught up in the nitty-gritty of the day-to-day. Ben managed 26 people by the age of 18, working with brands like Virgin Racing, and he credits his mentors with helping him get an array of skills. “For me, mentoring is not about having one person who is your mentor; it’s about having multiple mentors.” Ben started collecting his mentors when he was in his teens, calling on people to share their expertise in sales, marketing, finance, and other areas. Never having had a boss before, Ben knew he couldn’t rely on his own experience in the workforce to guide his management style, so he had to use his mentors’ inputs and opinions to help him lead his team.

Before COVID, Ben maintained a robust speaking schedule, which he credits with helping him grow his client base. Clients included the inaugural Young Enterprise with the UK government, aimed at unlocking a Silicon Valley mindset in England, and working with the British Royal Family on their initiatives. He used COVID as a chance to reset a bit—”leave the laptop at home”—and travelled through India and Thailand, falling in love with the local focus on community.

This focus influenced his work on Tahora, his community and culture app that he started in 2020. Tahora is designed for employees and their psychosocial needs, aiming to enrich their work community through better connections. He says that 47% of people don’t have a close friend in the workplace, leaving many folks without a sense of camaraderie and connection for long hours of the day. He shares the story of two employees who had trained for the same half-marathon without ever talking to each other about their hobby; his POV is that people’s well-being at work can be supported through friendships. Tahora comes from the Maori concepts of health and togetherness. “So often, we see community as just a group of people. In the Maori community, everyone has a part to play. Everyone belongs.”

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Trigger Warning: this episode discusses postpartum depression and briefly mentions suicidal thoughts.

When Erin Bagwell decided to turn to Kickstarter to get her movie off the ground, she didn’t expect to raise over $100K in 30 days, but that’s exactly what happened. Erin’s movie, Dream, Girl, is about the real-life experiences of ten New York City-based female entrepreneurs, and it turns out audiences were hungry for this type of story. Erin watched as women who were longtime experts in their field would have to prove themselves to boardrooms full of men in order to secure funding. “Wanting to be seen as an expert, wanting to be taken seriously, that’s still a big one,” she says. She needed to tell their stories.

So she pitched it on Kickstarter, and supporters were here for it. Erin credits her “really fabulous video” as the prompt that got people on board. “I spent a lot of money and I had a gorgeous video because I wanted people to look at it as a trailer. A glimpse of what the film would look like.” Erin invested in audio mixing, color correcting, and all the standard-issue Hollywood things to ensure that it looked amazing. “If you’re investing in a documentary, you want it to look, you know, like a film.”

Dream, Girl went on to premiere at the Obama White House in 2016. Erin was able to design a successful afterlife for her film. In her first full year of filmmaking, she made over $100K in sales and employed a team of two. She worked directly with her Kickstarter backers to bring the film in front of audiences and supplemented the screening income with a robust speaker’s schedule on top of that.

Erin’s twin inspirations for her first documentary had been her own experience being sexually harassed at work, and the collection of anonymous stories she collected into a storytelling blog called Feminist Wednesday. She was seen as a member of the entrepreneurial community, “because I had started this little WordPress blog,” and she had contact with women who were raising capital and launching start-ups. A lot of Erin’s audience was female founders and entrepreneurs who “really wanted to create spaces for connection.” She also linked up with influencers who promoted the film—and themselves—for their audiences. “People want to know your why. Why are you passionate about something, what is it that excites you? People are really attracted to that.”

For her next project, Erin’s own pregnancy was the catalyst and inspiration. “I was really interested in how people mother,” she explains. Her own experience with postpartum depression changed her expected filmmaking trajectory. “We don’t get to see a lot of great authentic stories about what it means to become a parent;” in making this film, she set out to change that. She felt “called” to share the truths and vulnerabilities of her first year of motherhood, and it became a way of healing her experience with PPD. Reviewing the footage gave her a sense of grace and compassion for her own story. Her goal is to let other mothers see themselves in the messy, ill-fitting parts of the early days of motherhood, and our own Damona Hoffman shares her insights into balancing motherhood and entrepreneurial momentum. Year One is now available to stream on YouTube.

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Most contractors get their big break with a high-profile job or a great referral. For Josh Temple, his breakthrough moment was going national on Mazda’s first-ever “Zoom-Zoom” commercial. Josh was a contractor by day, but when a receptionist at his first construction company told him he should try out sketch comedy, he fell in love with improv. His path then became a bit wilder than your average home renovator. “If you get a national commercial, you’re at least buying a car,” he laughs. Josh did double-duty as a construction company project manager and an actor in San Francisco before taking the leap and moving to Hollywood in 1999.

When he arrived in LA, he didn’t do the usual waiting tables gig: instead, he kept on with construction work. “As I hustled for work, I also learned more and more about construction.” He worked across many trades—HVAC, plumbing, tiling—and while he “was cheap,” he taught himself new skills by reading up on the subject. When home-improvement shows started to gain traction, Josh suddenly found himself uniquely positioned: he was an actor who knew about contracting. “I was literally, like, I don’t know which zebra I am: black stripes or white stripes?”

Since then, Josh has acted on sitcoms like Curb Your Enthusiasm, hosted competition shows, and been the resident contractor on HGTV and DIY Network home-renovation programs. He’s also been the head of his own contracting firm, so he knows all about what the camera doesn’t show.

Josh is very aware that, like many other industries, contracting has its fair share of what he calls “scam artists:” people who fail to deliver or deliver bad products. While shady operators hurt in every industry, when it’s a home renovation, “the scars run really deep.” Building trust between a contractor doing the work and the client employing them is a major step. As contractors, he says, “we have to look at the other side: it’s their house, their lives, their security.” While the drama might be played up for TV viewing audiences, Josh knows that there’s an inherent imbalance in the relationship. “You might have one chance every twenty years to remodel your kitchen, and you’re talking to someone who remodels them daily.” It’s a lesson in trust-building that entrepreneurs across industries can learn from: how do you prove to your clients on day one that you can be trusted?

2020 was a whirlwind of competing priorities that “smacked me in the face.” Josh isn’t immune from second-guessing his directions and decisions, and his experiments aren’t always successful. From trying to renovate a house by himself instead of with his usual eight-person crew (“brutal”) to the decision to pause his own contracting firm, it’s been a season of change.

But it’s not all tough news: Josh has leaned into his passion for Boys Town, a residential organization serving at-risk youth. He works with their Trade Life program to help connect young graduates of the Boys Town facility with careers in the trades. (Josh explains that for at-risk kids who can keep clean records between the ages of 18 to 22, “their chance in life skyrockets. So this was a real easy one for me.”) He’s been involved with the organization since 2012 when he did a PSA for the Boys Town, and he fell in love with the mission. Josh helped them re-launch the Trade Life program and expand it to new industries, including car mechanics, welding, and culinary training. Starting as young as thirteen, kids can try different programs and figure out what works for them. Josh himself donates tools, helps connect the program to tool manufacturers, and raises money.

Josh’s overarching philosophy isn’t a new one, but it’s a reminder of what can be accomplished through good communication. “Good, fast, and cheap: you can have two, but you can’t have three.” Josh is willing to work with clients on the parameters they set—budget, timeline, scope—but he brings decades of expertise and is able to gently guide them when they want all three. We love this philosophy, and we know we can use it in our own business relationships!

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Make Rejection Fun- Turn the icky feelings into a game and change your mindset about the negative approach to them.
Get Comfortable with Yourself - Define what confidence means to you, identify your personal values and live them daily!
Check Your Vibes- What relationships are you surrounding yourself with, what decisions are you making about work, life and the space that surrounds you. All of these elements directly impact your mood and your confidence when dealing with negative feelings.
Raise Your Frequency- Snap out of your negative cycles by doing something creative!
Identify Your 'Little Wins'- Do not overlook your small achievements, they are an important part of the journey, so CELEBRATE them!

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Emily Thompson’s experience starting the Being Boss podcast in 2015 is a strong argument for why you should always plan for success. She and her “business bestie” Kathleen Shannon started the podcast as a way of taking the conversations they were having about their businesses and being entrepreneurs into the public realm—and if they happened to promote their respective branding agency and web design shop in the meantime, well then, hey: that’s a bonus!

But a few months in and they were already getting ads. A little while later, they casually launched getaway events like the Being Boss Vacation and signed a book deal. The podcast was taking on a life of its own.

Emily was already a successful web designer: she had gotten her start with her Etsy store, having fallen in love with the idea of selling handmade things online. It was during this time that she became “enamored with branding,” and diving deep into who she was serving and why they should care about her business. Eventually, she took her expertise and passion to other business people. She graduated from offering pointers on online banners to running Indie Shopography, her web design agency for more than a decade.

So when it came time to launch Being Boss, it was a bit of a lark. “We had no business plan. We were just starting a podcast.” Emily and Kathleen went through the usual steps they’d take with any client—from the name, branding, website, and content buckets—but initially, they didn’t plan to monetize their passion project.

Their sudden success may sound amazing, but Emily cautions that it was “actually overwhelming.” The two of them experimented with a lot of different business tactics when they were building up the podcast, looking to see “what would stick.” Things weren’t always easy-breezy: their foray into Facebook Ads was a colossal failure, so bad they didn’t even do their customary postmortem. (Emily files aspects of their experiments under “what worked, what kind of worked, what didn’t work,” taking lessons from each. “It’s how we iterate and do the work we need to do to make the next time we do it even better.”)

And then: burnout struck. Emily says that the rush of opportunities on the podcast side, plus some setbacks in her personal life and other business, led to a feeling of burnout. For Emily, burnout felt like “Ew.” She found herself getting angry and listless when it came to work topics. “I was very much not myself.”

“For a while, we thought we were going to shut Being Boss down. We were both so tired.” She set a date, and promised herself that if her homebrew remedies didn’t work by then, she’d get a therapist (and she did); she learned to recognize the way she felt leading up to a depressive episode (“a very deep tiredness”), and she shifted her priorities, giving herself more time. But the major solution for Emily wasn’t to walk away—it was to invest more deeply. While her co-host and partner Kathleen wasn’t ready to leave her day job, Emily wanted to go all-in. “Our solution for mutual burnout wasn’t the same solution.”

Almanac Supply Co. started in 2018 because she found her podcast convos were starting to verge on the meta. “It didn’t sit well for me to show up as someone who knows business, but the only business I’m running is this podcast.” She thought back to her time as a web designer; she always “really envied” the folks who were working on product businesses. Pivoting to something nature-focused, hands-on and family-oriented—she even makes the candles with her partner—gives her a sense of purpose, and offering beautiful handmade items brings her back to her Etsy days, albeit with a major glow-up. “I get to show up and be the CEO.”

Resources

To learn more about our guest, go to https://beingboss.club/about

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast

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If your business ideas have ever been more of an airball than a total slam dunk, take heart: you are not alone. Sanjay Parekh is known for being ahead of the game as an entrepreneur, but even he’s had off-days. Take Pizza Impulse, his idea for pizza delivery that relied on random demand, random supply, and push messaging. His sales total on that project was a whopping two pizza pies. “There have been stinkers like that over time, but with the stinkers, you learn a lot,” he laughs.

Of course, you don’t know Sanjay because he’s a failed pizza emperor: you know him as the head of Mirage Data, a start-up that protects your data without sacrificing usability, as well as a founder of TogetherLetters. In his past, he co-founded Digital Envoy and Prototype Prime, and ran events like 2015’s Startup Riot. He’s also a host of Tech Talk Y’All, a biweekly comedy tech podcast. Is there anything this guy can’t do? (Besides running a pizza company...but we’ll forgive him for that.)

Like many entrepreneurs, Sanjay got his start in middle school. He was a candy-bar broker: buying piles of the sweet stuff and then selling to his peers. “If you ask a room of 100 entrepreneurs, more than 50 of them will say they did something like that.” He turned his early earnings into comic books, some of which he still has today.

In 1999, after graduating from Georgia Tech, Sanjay had an idea that would “make the internet better.” He noticed that the FedEx and IKEA websites were still relying on customers to select their countries before they could begin shopping, but suspected there was a tech workout-around that would smooth out that step. At work the next day, his colleague told him, “It’s either impossible to do, or somebody’s already done it,” but nope: Sanjay found that it was possible and he was first. Digital Envoy was born of this idea, and Sanjay left that colleague behind in 2000. Digital Envoy raised 1.5M in 2000, and 10.5M the following year; selling that first company in 2007 has let Sanjay “continue on this crazy entrepreneurial journey ever since then.”

A lot has changed since those heady early-internet days, and Sanjay isn’t nostalgic. For one, “You didn’t have the infrastructure stuff that we have now. You don’t need to buy servers. You don’t need to buy storage space.” While Sanjay’s early tech needs often gobbled up his large investments, “A lot of companies are able to start now without having to raise much money or any money at all.” Folks can now get in without huge initial investments, relying on quick, cheap, and global solutions like the cloud.

Being a tech-minded entrepreneur hasn’t always been champagne and gala events. Holding patents means that Sanjay has had to sit through “excruciating” sessions in order to explain the nitty-gritty of his products, but doing so “builds a moat to protect the company.” He doesn’t go for the NDA mindset—Sanjay figures that, with seven billion people on the planet, someone else probably has the same idea as him, somewhere—and he says that talking about his ideas is one way of finding out who else is solving that problem, or even why the problem can’t be solved in the first place.

He extends that philosophy to the way he approaches all his projects. “You’ve gotta become an extrovert when you’re an entrepreneur, at least in terms of business.” He credits his relationships with strengthening his business: from loyal connections to getting the support staff on board, and from funding events, to board service, relationships are where “good things happen” as an entrepreneur. Where are your best connections?

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For Jewish girls, the bat mitzvah is a pivotal moment of becoming a young adult and joining the adult community. For Rebecca Minkoff, who had been designing and sewing clothes since she was eight years old, the celebration was also a chance to showcase her fashion skills—and her “newly budding rack.” Pulling inspiration from the 1700s (think Bridgerton), Rebecca designed a square-necked, Empire-waist number that checked her boxes (and her parents made sure it stayed PG-13). For Rebecca, this was a foundational step in the lifelong process of becoming a fashion mogul. Now, in 2021, Rebecca Minkoff has flagship stores in LA, Hong Kong and New York City, among others; she’s also distributed by more than 900 companies worldwide.

While Rebecca has enjoyed early boosts to her brand—Jenna Elfman wore her “I Love New York” shirt on The Jay Leno Show in 2001—Rebecca has also worked hard to cultivate her business’s profile. For example, when she launched the Morning After Bag (also known as the M.A.B.) in 2005, she leveraged her industry connections, working relationships with Hollywood agents and stylists to ensure that the highly photographed celebrities of the early aughts all had a Rebecca Minkoff bag on their arm.

But getting there wasn’t easy: she’s navigated debts, doubts, and setbacks along the way. For example, Rebecca tells us she was once fired from a job after the CEO pulled her aside and told her that if she didn’t start channelling the passion she was putting into her own side hustle into the CEO’s fashion business, she’d be let go. Rebecca countered with, “I don’t honestly think I can do that.” At the time, Rebecca had small collections in only a handful of New York City stores, but her dedication to her own vision meant letting go of her main gig. “There was no safety net,” she recalls. Rebecca has since been in the CEO’s position, and she’s made the same tough call. “When you’re half-assing two things, you’ll never be able to fully focus on either.”

When the M.A.B. took off, Rebecca sensed her company’s reputation was starting to hinge on a single product. So she quickly escalated production on a range of offerings, from jewelry to clothing. “We knew we wanted to be a lifestyle brand, and the only way to do that was to go full-force and launch these other categories.” Her company president at the time was from the apparel world, and Rebecca herself had experience with women’s clothing design. She also brought on a shoe expert who could take them from design to manufacture. “We kept finding best-of-breed partners.” Unwilling to do a licensing agreement, she entered into manufacturing agreements—very normal in fashion—and she encourages people to explore different types of partnerships for themselves in their own businesses.

One of her most important partnerships is with her brother, who joined the company full-time in 2011. He had loaned her seed money for M.A.B. launch years earlier, and their partnership over the years has had ups and downs. Rebecca tells us that when things get really intense, she and Uri “hired a business mediator to help us when we get those critical impasses:” someone to “unsnarl the tangles” when the business and personal relationships become complicated.

Since 2018, Rebecca has also been channelling her creative leadership energy into the Female Founder Collective, a network for female business owners that offers education and resources. She’s also recently published a book, Fearless, that walks readers through her 21 steps for bravery in the face of business uncertainty. “My goal with the book is to throw out the rules: know you’re going to be scared, but do those things anyway.” She knows, from long personal experience, that taking risks is not a fearless endeavor, but moving through fear is a key step for success.

Resources

To learn more about our guest, go to https://www.rebeccaminkoff.com/

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast

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Most people go to Las Vegas hoping to shrug off the demands of work, but for Paddy Moogan, a trip with mates turned into a life-changing business opportunity. On a trip to Sin City, his friend approached him with a proposal: why not take Paddy’s expertise in digital marketing and launch their own agency, a shop where they could call the shots on everything from work culture to clients. “It felt like a good idea at the time to talk about starting a business together,” he says, and after taking thirty minutes to come up with a plan, they decided to go for it. Aira was launched in 2015.

The early days took some adjustments. In the first six months, Paddy and his partners tried to divide up their roles and responsibilities, with Paddy taking on the marketing, sales, and raw strategy, while his co-founder focused on delivery and operations. But they soon discovered that divvying up the job didn’t mean better work. “Because we split our roles, we didn’t actually work together all that much, the way we had for the first nine months. We did our best work when we were working together.” Bucking convention, they got the band back together and decided to keep their business roles much looser.

It’s this not-quite-conventional approach that helps keep Aira at the top of its game. While other shops might do SEO because a client asks for it, Paddy and his team slow the process down and dig deeper into how the client wants to grow. He makes a point of pinpointing their client’s actual needs—ranging from content marketing to paid media—and how they interact with the business’s pain points (including tricky spots like investor pressure and pitch meetings). Aira takes a collage approach, offering a buffet of short- and long-term solutions that will both quiet a nervous investor and actually, you know, grow the business.

Paddy reminds us that SEO is not instant gratification: it actually takes six to twelve months to pay off. “As a company, the thinking has to be in years, not months.” For faster results, he suggests investing elsewhere, like in paid media or paid search in advertising. But he also reminds us to look at what we’ve already got: do you have a big email list that’s just sitting there? One-time customers who could be convinced to return? “What have you already got that you can leverage?”

Paddy’s ultimate goal is to create a work culture that lets people and businesses be themselves. He encourages his team members to watch their personal triggers—anything from skipping meals to not getting enough exercise—that can lead to crummy decisions or bad moods. He also recognizes that for some, Aira will be a stepping stone along a long career; he does his best to be a springboard, not a gate. Ultimately, he says, “We wanted to build somewhere where, if we were employees there, we would be happy to work.”

Resources

To learn more about our guest, go to https://www.aira.net/

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast

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If you’ve ever started your exercise time by standing there for 20 minutes choosing a podcast, know that you are not alone. You are in the company of JJ Ramberg, who launched GoodPods to help curb that endless search for great podcasts by tapping into what your friends and favourite influencers are already listening to. “It’s like Goodreads for podcasts,” she explains, channelling the energy of the popular book recommendation site.

Before launching GoodPods, JJ—who was already a podcaster herself, with Been There, Built That—talked to more than 700 people about their experiences with podcasts. Those folks ranged from established producers and hosts to the casual listeners who tuned in a few times a month. At the end of those conversations, she had a wealth of knowledge and used it to release something special. “We launched a product that people liked. These were people who really enjoyed the app and realized that there was nothing else out there like it.”

JJ’s focus has long been on products that improve your life, but also give back. GoodShop, another project of hers, combines coupon codes for more than 7000 popular retailers with a chance to donate the difference to national and international charities (they’ve raised over $70K for the ASPCA alone). And SearchKibble’s mission is to feed pets living in shelters—each search on the site is worth two bites of kibble. JJ startedSearchKibble in large part because of the COVID-19 pandemic, when shelters saw a serious dip in donations. “It’s a way for people to do good while they’re doing what they’re already doing, which is search the internet.”

Her early days hosting Your Business made her a trailblazer in the small-business world. “Back then, there was nothing else like it. There was no Shark Tank.” She helped bring stories of entrepreneurship into people’s living rooms and shared the good, the bad, and the ugly with viewers. “I was hosting the show at the same time that I was building my other company, and I was as much the audience as I was the host.” Over the years, she saw patterns of successes and missteps.

Which leads us to failure, an entrepreneur’s biggest worry. “The number-one thing that successful people can do is deal with failure.” She tells us the story of a soapmaker who saw half his business disappear overnight, and how he dealt with it. We know that failure, by itself, is not fun; it’s the moving-forward process that brings in the learning.

Speaking of learning, JJ’s entrepreneurial education has taken some unexpected swerves. Sure, she’s a Stanford MBA graduate, but she’s also learned a lot from her family, many of whom started and grew businesses of their own. Her mother was a special inspiration: she capped a long stint of staying home by launching her own successful business with JJ’s brother in her 40s. “I watched, firsthand, how incredibly fun it could be.” JJ has since taken up the mantle, and partnered with her brother on both of her companies. “It seemed natural, when we had this idea, to try it.” Their previous experience dovetailed and diverged in interesting ways: she knows the media and marketing side, and he brings the tech expertise.. She says the fact that they care deeply about each other’s lives—outside and inside the business—”makes it all work for us.”

JJ is now passing on her entrepreneurial spirit to the next generation with her children’s book The Start-Up Club. She likes the idea of familiarizing her kids with the language and ups and downs of the business world. “They can see sometimes things work brilliantly, and sometimes things do not work as you’d planned them to be.” She wants to see them experiment, try new things, and yes, fail, with her same fearless approach.

Resources

To learn more about our guest, go to https://www.goodpods.com/

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast

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Everyone’s story matters! Lisa wants to know everything about the people pitching to her, from their business background to how many pets they have. And if you’re not the one running the day-to-day business, make sure to bring that person into your pitch strategy: she wants to meet them too.
Where do you want to end up? From passing on the business to your kids to selling in five years, make sure every co-founder is working towards the same long-term goals.
Stability is attractive. If your work history doesn’t show a lot of commitment to a role, company, or profession, investors might be less interested in committing to you.
Market research and proof of concept mean you’re coming in with knowledge and fans! Show your investors you’re armed with knowledge and customers.

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Lisa Song Sutton describes herself as a “serial entrepreneur,” and her portfolio is proof. From Sin City Cupcakes—a boozy bakery she co-founded in 2012—to Ship Las Vegas, her mailbox and shipping stores across the city, Lisa’s portfolio is a truly diverse set of business assets. Add in her real estate sales team, not to mention a women’s swimwear and accessories e-commerce store, and we are wowed. Her goal is to build up lifestyle businesses to eventually graduate from running the day-to-day and take on new projects. “I’m big on legacy building,” she says.

You may know Lisa from her 2014 stint as Miss Nevada. Lisa’s mother is a former Miss Korea who encouraged her to go the pageant route. Lisa got a late start in the pageant scene, making her debut at 29 (right before she aged out of the competition altogether). As part of her training, she worked with established pageant coach Bill Alverson, who focused less on what she looked like in a bathing suit and more on what she had to say. “By the time I competed, I was done with grad school. I was a business owner by then. I had a different lens and perspective on the title.” Lisa saw her time as Miss Nevada as a way to step up her involvement in the local community. “Why not get further ingratiated?”

After the crown comes the community service: Sutton made nearly 500 appearances as Miss Las Vegas and Miss Nevada. She volunteered in schools, read in hospitals, and made personal connections with people in her community. “It was an incredible experience.”

Her knack for connecting to others has made her a natural at business partnerships. She took on her first founding role in 2012 with Sin City Cupcakes, a business she launched with a friend while still working as a lawyer. Lisa is a fan of teaming up with her friends. “There’s value in partnering with someone you really know. You know what they’re like when they’re angry when they’ve had a bad day when they’re stressed out. You know what happens.” (And Sutton’s partners know her personality as well!) Her advice for a successful partnership is to “make sure everything is papered up.” But treating business agreements like a living document is also key because as the company grows, your roles will change.

Lisa is currently on the board of StartUp Nevada, an incubator supporting entrepreneurs in that state. As an angel investor, her advice to female entrepreneurs is simple: ask for the money! “It’s never perfect, but you have to take action.” She suggests female entrepreneurs give themselves a boost by following successful business leaders like Sarah Blakely (the founder of Spanx), who share resources and encouragement with their followers. “Who are you following? What kind of data and messaging are you consuming as a woman, a female founder and an entrepreneur?” Unfollow the accounts that don’t add value, and chase the ones that give info and encouragement. She also encourages female entrepreneurs to familiarize themselves with their local networks of female angel investors, who are often eager to work with women. But, she says, think carefully about where your business is going: do you have an exit strategy to ensure your investors get paid?

In the nitty-gritty, she encourages women to focus on metrics when pitching—storytelling is a bonus, but focusing on OKRs gives investors a peek at your gameplan. Taking a business’s goals quarter by quarter communicates a long-term vision in a way that is concrete and accessible to the folks considering a pitch. She says that, compared to male entrepreneurs, women wait longer and are further down the pipeline before they start pitching for investments. “We talk ourselves out of being ready. We have to get out of our own way.” As she puts it: closed mouths don’t get fed. Especially not cupcakes!

Resources

To learn more about our guest, go to https://www.lisasongsutton.com/

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast

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On this week’s Nerdisode, Nayamka Roberts Smith, aka Nai, the labeautyologist, gives us her tried-and-true methods for building an authentic and engaged social media audience.

Choose a social media avenue that plays to your strengths, and make sure you enjoy it. Want to blow up on Twitter? “You have to like tweeting! You have to talk a lot.”
When the creative juices are flowing, do a brain dump; stash your great ideas for a day when you’re not in the mood to create.
Repurpose your content to help your audience absorb it in different ways!
'Mine' other data sources for content ideas: when you search your topic ideas online, make sure you answer those Google auto-fill questions in your video or on the blog.

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Nai Roberts-Smith might be the mega-popular skincare expert labeautyologist these days, but like many entrepreneurs, she started in a dorm room. She was an amateur nail technician, complete with a wall of polish colours, and she would do nails for less than the price of lunch. “I had a group of friends who all did beauty services,” she says a barber, a few pals who did hair, and a league of friends acting as low-key brand ambassadors across campus.

When she left college, she joined a salon as a nail tech but has aspirations of becoming an esthetician—a licensed professional who does facials and other skin-care treatments, usually at a spa. “I was good at nails, I liked doing it, and I felt kind of stifled by that.” But her hometown shop was full of estheticians, and they were unwilling to add Nai to their roster. She debated bringing her skills onboard cruise ships before realizing she would likely find work anywhere that was beautiful—Jamaica, Hawaii, Miami, or her new hometown, Los Angeles.

In LA, Nai was “broke,” but she knew the demand was there: she could stand on a busy street corner and see three spas on a single block. As she launched her business, she made a strategic decision to grow her social media presence as well. “I knew I had to reach people who weren’t just right in front of me.” She launched her YouTube channel as soon as she moved to LA. “Being on social media has completely advanced and changed my career trajectory;” she now has almost a half-million subscribers.

Sometimes entrepreneurs get tripped up on how to translate online impressions to actual sales, but Nai has a knack for it. When she started, Nai would demo her treatments on Twitter and YouTube and encouraged LA locals to book in with her; at the time, 45% of her clients came from that sales funnel. She examined her analytics for out-of-town interest—like the viewers watching from Atlanta and New York—and headed to those cities for pop-up skincare treatments. “Fifteen people made it worth the trip,” especially after she factored in word-of-mouth promotion and local hype.

It might seem counterintuitive to give away knowledge that she could be charging for, but Nai says it’s actually a sales driver when she does. Maya Elious taught Nai that if she wasn’t able to give away her knowledge for free, “you’re not even knowledgeable enough to be an expert in what it is you’re doing.” Nai estimates that, though she’s shared plenty across various platforms over the last five years, it only represents about 10% of her body of expertise, and her interactions with fans and clients make the trade-off worth it.

She’s also a master of the thoughtful pivot. When COVID forced her to shutter her spa last summer, her collaborations with brands like Fenty and Target became much more important. She also launched her own line of merch, a spa-inspired line of garments including robes, turbans, and scrunchies. “I’m still talking to the same people.” Her third line of defence against COVID losses was launching a virtual consulting stream.

Nai sees herself as filling an important gap in esthetics: as a darker-skinned Black woman, she brings knowledge about melanated skin and its unique needs to an industry that doesn’t always cater to them. “When I went to esthetics school, there were very few women of colour who went to the school.” Working with different skin tones and types is a key factor in successful treatments, and Nai says, “I felt like my presence made the other estheticians better.” Through some of her content and partnerships, she’s started filling the gaps in esthetic’s typical service and knowledge. “I’m here to talk to people who weren’t spoken to before.”

Resources

To learn more about our guest, go to http://labeautyologist.com

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast

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Earlier this week, mega-event planner and reality TV host David Tutera talked to us about his path to success; in our Nerdisode, he gives us the nitty-gritty on keeping his clients and team happy.

Which questions do you need to ask to get your client’s real budget? David uses his knowledge about wedding dress designers and DJs to strategically (and diplomatically) figure out how much his clients are willing to spend.
Keep your clients in the loop on expenditures! Going over budget isn’t a surprise for David’s clients.
Compartmentalize your projects. A messy desk can lead to client mix-ups!
Stay on top of your staff and vendors—since delays can be hard to overcome, David keeps an eye on deadlines and deliverables, and steps in where he needs to: “I know when someone’s not about to meet the goal.”
When mistakes happen, don’t punish your staff: look for productive, positive solutions that fast-track success.

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We know that certain industries thrived during COVID—home renovations and online shopping, anyone?—but there’s no denying that some sectors took a major hit. We got a call from Eve, an event planner wondering how she can move forward post-pandemic. Well, we brought in the capital-E expert to answer Eve’s question.

David Tutera is best known as an event planner for the stars and reality TV show host. His full business is much more diverse, including industry training events, a partnership with Macy’s, a bridal boutique, and more. David’s work focuses on “the art of celebrations. Any celebration should be about joy, and that’s how I make a living.”

David is the grandchild of an Italian immigrant, an entrepreneurial flower shop owner who taught David some of the basics of running a business. At the age of thirteen, David worked the phones at the shop, listening in as his grandfather ran the show. “He was giving me these nuggets of information” about the importance of respecting staff, profitability, and paying attention to details. His grandfather also invited David to watch the floral designers at work, sparking his interest in creative industries.

After a brief foray into law school, David took an unexpected detour into singing telegrams (!!), where he decided, “If I was going to leave school, I knew I needed to make money.” Dressed in anything from a gorilla suit to a barbershop quartet, he wrote and performed ditties for clients. When the telegram business owner decided to sell, David was first in line with an investment from his grandfather.

His first event-planning client was a woman who had passed his office window display—very silver lame and ostrich feathers—and asked him to “do” her son’s bar mitzvah. Despite not being 100% sure what a bar mitzvah was, he said sure, a moment he credits as teaching him “the power of yes.” He slowly transitioned from telegrams to “little parties,” and ultimately found his footing in events.

While he initially passed when reality TV came calling in the early 2000s, David has now been a media personality for more than 17 years. One twist to the early days of his fame was that his biggest and most lucrative clients didn’t want to deal with David’s busy TV schedule, leading to an unexpected business drought. “I literally thought, did someone cut my phone line?” He eventually started to attract new clients interested in both his fame and his skills. The experience made him very aware that all projects have their own life cycle, and will have the best moment to launch; anticipating those ups and downs will help smooth out turbulence in cash and client flow

It wasn’t always easy and luxurious: he danced with the IRS, couldn’t meet payroll, and grappled with some pretty serious business setbacks. He made a point of protecting the people he worked with, and fixing his mistakes. While it was fifteen years ago, he says “when you go through those large problems, significant amounts of them, you learn quickly what to do.” After those hurdles, he put his support network in place—the folks who can do his taxes while he takes care of the creative side. “You build this puzzle around you. Those people allow anyone in this business to elevate themselves.” By freeing up his administrative tasks, he can focus on keeping his creativity juicy.

During COVID shutdowns, he started rethinking events and his business. He did a COVID-safe live event in March where the aim was to figure out a future for the events industry, which he sees reviving in full in 2022. “We have to figure out a way to continue our livelihoods.” He also recently discovered that his grandmother was a seamstress, and great-aunt owned a bridal boutique, adding a sense of destiny to his own bridal atelier inspiration. “Sometimes, the things that you do are really laid into the roots of your family.”

Resources

To learn more about our guest, go to https://davidtutera.com/

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast

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If you think television journalism is glamorous, Erica Mandy is here to set you straight. She started as a “one-woman band” in a small TV news market, where reporting on location often meant that she was the photographer, camera operator, writer, editor...all while also being the on-air journalist. “That weeds out the people who are in it just to be on TV,” she laughs, comparing her small-town news experience to “grad school” for TV journalists. Over the next seven years, she worked in successively larger markets, finally landing at CBS News in Los Angeles. She was there for three years, working on-air in the second-largest TV news market in the country.

But Erica’s passion wasn’t just the news—it was the news in a whole new way. In 2017, she left CBS to launch The NewsWorthy, a daily news podcast that offered a “fair, fast and fun” look at the day’s top stories, all delivered in fifteen minutes or less. When she started, audiences were tuning out the news altogether, saying it was too biased, time-consuming, depressing, and overwhelming. “Those were the four words everyone kept saying,” she says. She decided to solve the problem for people who didn’t want to be left out of the current-events loop altogether, but who needed a different avenue to consume it.

She knew she was on the right track when the heavy hitters started launching their own podcasts. From the time she conceived the idea to the day she finished her contract with CBS New, Erica watched a number of big players enter the arena with their own news podcasts. After a brief crisis of confidence, she decided to forge ahead. “I realized that the whole point of me starting this was that I brought something new to the table. I offered something unique, which was the vibe of the show.” Her credibility as a journalist allowed her to cultivate a more independent viewpoint on current affairs, allowing folks to trust her unbiased POV and her approachable voice.

Instead of competition, Erica now sees the bigger producers like NPR as allies. The big shops are an entry point for listeners, who might start with the biggest news shows, but then look around for what else is out there. That’s where The NewsWorthy lives.

After her first year, she looked back and asked two questions: “Did I start to make money? And am I moving in the right direction?” She had made her first dollar, and listeners were reaching out to say they felt more informed and more able to participate in civil life— she even inspired some new voters!

She’s also expanded her team so she can focus on growing the podcast “as a business,” taking a data-driven approach to advertising, as well as partnering with investors who bring not just money, but also visibility, credibility, and the ability to hire additional staffers. “Some of those resources that I got from the investment, were more important than the funding.” Her focus has switched from delivering daily content to the long-term, broad-scope vision for the show, and it was “so nice” to have time freed up for other parts of her business.

Lately, Erica’s pregnancy has underscored the need to ensure her business can run without her day-to-day involvement, including hiring a temporary host for the podcast. “It doesn’t have to be me all the time,” she says; it just proves that being a smaller player just means there’s always room to grow.

Resources

To learn more about our guest, go to https://www.ericamandy.com/

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast

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Mine your own life for inspiration! We bet you have at least a few photos on your phone that can prompt you to dig deeper into your own experiences.
What’s in your notes? Check your written records on WordCounter to reveal which ideas you keep coming back to. (Morgan checks her phone’s notes app monthly!)
Write your to-do list by hand. It’s an authentic record of what you’re thinking about, and sharing that with your community helps folks recognize themselves in you (and your four loads of laundry).
Listen to yourself! Literally, that is: Morgan uses Otter to verbalize her ideas and to keyword her ideas for easy tracking.
Write about what makes you angry! That will help you get to the heart of what you care about. Start making a change there.

Resources

To learn more about our guest, go to https://morganharpernichols.com/

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast

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Morgan Harper Nichols might be the rarest bird in the entrepreneurial aviary: she was actually looking for a nine-to-five job when she started as an internet sensation. After a half-decade on the contemporary Christian music scene, she was tired of hustling. “It’s a hard industry to be in,” she says. She was looking for something more stable, but, she laughs, with an English degree, “there aren’t a ton of Indeed posts out there.”

In 2016, she put her frustration into words, shared her personal poem on Pinterest, and then forgot about it. But in a few short weeks, that poem had been repinned over 100,000 times. She had gone viral without really trying to.

From there, she’s launched herself as a visual artist and poet, been picked up by publishing company Zondervan, amassed more than 1.7 million Instagram followers, done collaborations with Coach, Adobe, Vogue and Aerie, and launched The Storyteller App, where, for $2.99 a month, subscribers receive a daily infusion of her poetry and art.

She credits her followers for the push that got her where she is today. Back in 2017, a DM in her inbox requesting an illustrated poem netted her fifty dollars—her first commission—and the sense that this was something she should pursue.

Coming from the music world, a “gig” often meant shelling out her own money to perform: a flight here, a venue rental there. Of course, Morgan would get paid eventually, but she discovered that poetry doesn’t have that same cash-flow issue. She continued to share online, and her audience grew. That first commission had given her the confidence to believe, “There’s gotta be at least a few other people out there who are willing to support me in this way.”

She was also, for the first time in a long time, able to experiment. She is delicate in saying so, but the Christian music world doesn’t always reward innovation. Channelling her creativity into these new outlets was something she could do from home, and that didn’t cost her money to produce. “I was investing time, but I wasn’t losing thousands of dollars by sharing something on Instagram. If it didn’t work, try something else the next day.” It gave her permission to craft her own voice and the freedom to explore.

Morgan was also diagnosed with autism in her early 30s. Understanding neurodivergence as a creative working with other brands has been tough but necessary. “I’ve had to ask for a lot of help in areas where I was pushing myself.” (She admits to getting bogged down in admin tasks because she believed that she had to do it on her own.) Her diagnosis forced her to grapple with the parts of her day where she struggled (that inbox, for instance), and pass those over to her business partner and husband so he could support her more effectively.

While the traditional work world might reward the most neurotypical, entrepreneurs get to create their own work settings and figure out what makes them really thrive. For example, Morgan’s hypersensitivity to colour and stimulation might make grocery shopping a problem, but it makes her artwork richer and more resonant. She then shares that with her collaborative partners and followers. She’s created a work-life that supports her entire life—a way of operating that makes the world more beautiful indeed.

Resources

To learn more about our guest, go to https://morganharpernichols.com/

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast

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In this week’s episode, we talked to Carl Smith from Bureau of Digital. In our I Make a Living Nerdisode, he gives us his top tips for building organic and authentic communities.

Building community isn’t something you check off a list: it requires a commitment and a purpose to keep it going.
Communities evolve to reflect their members’ needs: what you start with might not be what you end up with.
When you’re scaling an intimate group into thousands of members, insist on a strong code of conduct.
Don’t be scared of your communities taking off without you: you wanted a group of people to get together and do something, so let ‘em!
Meet your community where they live: for Bureau of Digital, it was Slack. Where is yours?

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When Carl Smith’s eleven-year-old daughter started getting into classic rock like Joan Jett, she asked her dad how he wanted to be remembered. Carl had run his own digital agency nGen Works for twelve years, but his daughter’s questions about legacy made him realize his true passion was boosting other leaders into the stratosphere. “If you’re a leader, you probably didn’t go to school for that,” he says and gave himself the goal of figuring out how to help people in leadership roles unlock their potential.

The first Bureau of Digital event was a couple of dozen digital shop owners talking about what worked and what didn’t. And, as Carl says, “We fell in love with each other.” Their mission was to provide community to the digital space.

But from the beginning, it was clear that some folks weren’t in the room. In 2012, there were only a handful of women and BIPOC people at the table, and gender diversity became a bigger issue as the Bureau took off. Carl shares that women often didn’t sign up for owner-focused events, sticking with ones designed for operators. After another gender-unbalanced event, Margaret Lee, who ran Google Maps for nearly a decade, pulled him aside for a chat. She suggested they offer a women’s leadership camp. His response? “Yes, ma’am.”

It turned out to be a half-solution. At one event, he was approached by a participant who said, “White women’s leadership camp is going great.” When he flinched, she reminded him, “It’s going to be work, Carl.” He knew he had to figure out where to go from there, but he couldn’t do it on his own.

Enter Project Inkblot. Co-founders Boyuan Gao and Jahan Mantin work with organizations as coaches to build diversity—the real stuff, not trendy hashtags—into their operations. For Carl, it meant taking a step back and asking them to lead the Bureau of Digital through a process of designing Beyond Diversity: an event, a fund, and a mindset that is honest about why BIPOC people and women often feel sidelined in digital communities and is working to change that. “When there are people who can do it correctly because they’ve lived it, I need to get the hell out of the way.”

Bureau of Digital has experienced an explosion of growth since January 202—membership is up a mind-boggling 750%—and while membership hadn’t been a priority before the pandemic, the Bureau’s 500+ members have changed that. They have a robust and active Slack channel full of people sharing frustrations and solutions on topics as diverse as navigating the Paycheck Protection Program to how to hire remotely. Carl regularly mines the Slack channel for topics to write about in the Bureau’s newsletter.

And while the Bureau may have started in a single room, Carl recognizes that online communities are here to stay. They’re not planning anything in-person until 2022, and “We’re going to have an online equivalent to the in-person events as well.” Score one for accessibility.

Most of all, Carl wants leaders (especially those without formal leadership training) to rid themselves of the mindset that being in charge means they need to know everything. He says there’s “this fear that someone will find us out,” speaking to the imposter syndrome often found at high levels. But not knowing is part of building the right team and the right culture. “Your job is not to contain a team behind a fence; it’s to create a place that is a magnet,” he says. Creating a diverse, authentic, safe place for leaders to actually get the skills they need to lead the way—now there’s a legacy.

Resources

To learn more about our guest, go toBureau of Digital

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast

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Bryan Clayton, CEO and Founder of GreenPal and small-business mentor, gives his five best ideas for entrepreneurs and small-business owners:

Bake in your marketing strategies from the earliest days of your business and plan on getting your solution out to your customers.
Spend time experimenting with marketing techniques, from organic SEO to social media channels, and figure out what works best for you.
Be honest: are people willing to pay for what you’re doing? Are they coming back for more?
Be impressive to potential mentors: show them your hustle and how far you’ve come!
Tune into passive mentorships like YouTube channels and (ahem) podcasts for key insights from your favourite thought leaders. Only take advice from folks who have been where you’re going!

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In 1998, Bryan Clayton was one more 18 year old with a lawnmower, keeping his neighbour’s outdoor spaces nice and tidy. His marketing strategy wasn’t much more than a photocopied flyer. But over the next 15 years, his landscaping business—by then called Peach Tree—took on major corporate clients and grew to employ over 150 people and bring in more than $10M annually.

But going big meant that they were leaving behind the little guys. Peach Tree was past the point of taking on $30 homeowner jobs, but frequent calls from potential clients proved the demand still existed. Taking inspiration from Uber, Lyft, and Airbnb, his app GreenPal was designed to connect customers with lawn care companies who operate on a smaller scale.

GreenPal’s business has doubled every year in the last eight years. His initial value proposition has stayed mostly the same—referring customers to companies—but 300,00 people use the app, and he’s bringing in $20M in revenue each year. By cutting out the legwork of researching company names and reviews, organizing payment, and setting up a lawn care schedule, the app goes way beyond the typical “neighbour kid with a lawnmower” set-up and ties up loose ends for both customers and the companies they work with.

That’s not to say the early days weren’t tough, but never underestimate how far a little naivete can take you. “If I had known how hard it was going to be, I would have gotten scared and never started,” Clayton laughs about the app’s early days. With two co-founders and no one knowing how to code, they put $150K into the first version of GreenPal, and it was...a failure! The next three years were spent supercharging their tech skills and developing a robust customer service feedback loop that continues to this day. When they relaunched, the grass was indeed greener on the other side.

It also helped that Clayton’s partners were well-chosen thick-and-thin types, a relationship that he compares to a marriage. One of our listeners, Gabby from Austin, asks about the value of a co-founder, and Clayton recommends careful consideration. “Don’t just go get a co-founder because you think you have to,” he says. Though there is start-up wisdom behind having both the hustler and the hacker on your team, Clayton reminds us that a co-founder partnership may last longer than some marriages (and be messier to dissolve if the day ever comes).

They keep themselves default alive, so their profits don't outweigh business expenses, and they keep their burn rate low. Taking a practical, sustainable, slow-and-low approach—which he recommends for nearly all small businesses—meant that they could keep going when things get tough. GreenPal also inadvertently tapped into our society's “contactless” needs during a pandemic, a consumer mode that people now use for everything from clothing to groceries.

Clayton credits his personal and business growth with a surprising Super Mario mindset. “Look at your business like a video game,” he says. “You only have to beat level one, throw up the flag, and get through a level at a time.” By focusing on just one or two key things at a time, Clayton says, entrepreneurs can be heroic about setting goals and moving their businesses forward. “I really wanted to make something of myself, and I felt like business was the vehicle for me to do that.”

Resources

To learn more about our guest, go to: https://www.yourgreenpal.com/

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast

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For anyone who’s ever Googled a symptom, this episode goes out to you. Crystal Evuleocha, founder and CEO of Kiira, is a kindred spirit, but her self-diagnoses landed her in surgery after she didn’t know when to get help. Her experience led her to develop an app that connects college-age women with doctors they can trust. In a year where telemedicine took another leap forward, Kiira and Crystal were on the cutting edge.

In this week’s episode, we talk to Crystal about her experiences as a woman of color in the funding world—Kiira has counts Bumble Fund and Serena Ventures as investors—and her journey through pitch competitions, client acquisition, and how COVID changed (and supercharged) her business: “Our entire corporate strategy is to increase access for underrepresented people.” We also hear from Bumble's Strategy and Social Impact Associate Director Cybil Zhang of Bumble Fund's work funding Black and Latinx female entrepreneurs.

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

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Get free BTA resources here: https://trybta.com/imal

We know you’re awesome—what entrepreneur isn’t?—but do you know how to transform your awesome skills into a viable business? Danny Kerr is the co-founder of Breakthrough Academy, where he teaches tradespeople to scale up their business. They offer lessons on financial management, setting goals, recruiting and managing staff—all the beautiful administrative work you don’t see during a construction project.

A former “lost university child,” Danny got started as a College Pro franchisee, where he learned the basics of small business ownership, and then worked for the company directly. He eventually oversaw a corps of over 400 painters while still in his 20s. He co-founded Breakthrough Academy in 2015 to help contractors bridge the gap between “grassroots” level entrepreneurship and more enterprise-level business management. We talk to Danny about what makes a business partnership like a marriage, how to balance active and passive marketing strategies, why we shouldn’t be afraid to delegate, and the one skill every entrepreneur should be developing in 2021. Check out Breakthrough Academy’s Business in a Box webinars for ideas for growth and sustainability in the new year.

Get free BTA resources here: https://trybta.com/imal

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

Join us next week for our Season Finale in a special collaboration with Bumble Bizz.

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Guest- Julie Nolke

“There’s no one path to success, and that’s what's really exciting.” If you’ve ever watched a YouTube video from a dedicated content creator and wondered exactly how they got there, you’re not alone. Julie Nolke is one such creator—a theatre school graduate who hustled at her day job and originally used her YouTube channel as a workshop space. She’s committed six years to her channel, doing everything from the acting and writing to the editing and ad selection. Her journey to viral stardom includes a variety of partnerships, plenty of diverse income streams, and a lot of scrappiness.

On this week’s episode, we talk to Julie about why content creators should focus less on fancy gear set-ups and more on emotional resonance, how she partners with outside brands, and why creator-driven platforms like YouTube can help skirt the traditional gatekeepers in creative industries. Nolke, who was named one of YouTube’s Top Breakout Canadian Creators in 2020, has maintained her distinct POV as the view count ticks up.

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs

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“Is your space feeding you? Or is it getting in the way?” These are the kinds of questions Inessa Freya asks her clients. As both a psychotherapist and a feng shui expert, Inessa taps into her knowledge of how our spaces affect our mood and vice versa. In a year when we’re all spending more time than ever in our house, creating nourishing and fulfilling work-from-home environments are an investment in business success and good mental health.

We talk to Inessa about the surprising ways our values influence our clutter, why home-edit shows are so huge, and how an open window can change the energy of your space. She also walks us through a quick ritual for dual-use spaces—if you’re working in your bedroom or living room, this one’s for you.

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

Guest- Inessa Freya- Website

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Rafael Espinal knows freelancing. His parents both moonlighted—as a photographer and a baker—and as part of the New York City Council, he helped pass the “Freelance Isn’t Free Act,” which allows NYC-based freelancers to tap into city support in resolving delinquent client payments. He’s also the youngest person to be elected to the New York State Assembly, and a former teacher. Now, as Executive Director of the Freelancers Union, he spends his days helping freelancers get organized, big picture-style.

“I knew that at some point in my life, I wanted to be part of an organization that advocated for creatives and freelance workers,” says Rafael, and the Freelancers Union does exactly that: they got started by offering insurance to workers outside traditional employment set-ups. They’ve since grown to include a networking hub, a popular blog, a directory of Black Freelancers, and service discounts for members. This week, we talk to Rafael about why COVID-19 hits them especially hard, why freelancing is an unexpected youth movement, and why freelancers definitely have power in numbers.

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

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Join #IMakeALiving alum Elaine Pofeldt for our next webinar “Building A High-Revenue One-Person Business In Challenging Times” on November 19! Elaine and her four expert guests will walk us through fail-proofing your business and scaling revenue. The first 100 attendees will receive a free copy of Elaine’s book “The Million-Dollar, One-Person Business.” Sign up today!

Ruth Elnekave knows what stress is. After all, she’s got five different degrees and diplomas, ranging from an MBA to her chef’s papers. Her business Joya combines her far-ranging professional experience (including business and marketing) with her life-long passions (cooking and holistic nutrition); the end result is wellness-oriented products that bridge the gap between soothing stressed-out customers (hello, paging 2020!) and being totally delicious.

In this episode, we talk to Ruth about connecting with her grandmother through childhood family feasts, how her personal experience with stress led her to create Joya, and the silver linings of launching a business during a pandemic—turns out it’s pretty good for connecting with customers on social media. We also dive deep into the effects of stress on the body and why food is a “beautiful way to experience other cultures.”

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

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FreshBooks is proud to be a Baeumler Approved partner. Check out their website to learn more about joining the program or finding your next contractor through them!

Bryan doesn't believe he's put in an honest day's work unless he gets his hands dirty! A natural-born teacher, the Gemini-award winning host has been educating and entertaining viewers across Canada and the US for over seven years on the hit shows House of Bryan, Disaster DIY, and Leave it to Bryan.

Learning valuable tricks of the trade from his father, a meticulous aircraft engineer, Bryan spent his childhood summers building his family's cottage from the ground up. His entrepreneurial spirit emerged at the age of 14 when he opened his own handyman business doing odd jobs for neighbors.

After earning a dual degree in Political Science and Business, Bryan was headed towards a career of practicing law. Realizing he'd rather be renovating than be chained to a desk, his innate passion for building took over and he traded in his tie for a tool belt and founded his contracting company Baeumler Quality Construction. Bryan has now built the 'Baeumler Brand' to include Baeumler Construction, Baeumler Approved, Baeumler Productions, Baeumler Media, and the newly launched Baeumler Family Foundation for Kids. Each and every one of his companies prides itself on professionalism, respect, and quality workmanship. A few years and several hit TV seasons later, Bryan's tackling even more projects than ever - and loving every moment of it!

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

Our Guest- Bryan Baeumler

Oh and remember, if you are planning your next getaway, consider visiting Bryan's newest project, Caerula Mar in the Bahamas. In a world of endless stimulation, Caerula Mar Club is a hideaway; grounded by the island’s rhythm. Visit www.caerulamar.com to make your escape!

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When times get tough (like, say, most of 2020), it can be easy to dismiss an accountant or a bookkeeper as a business frill. Let Twyla Verhelst change your mind. She’s the Head of FreshBooks’s Accountant Channel, and while she’s got a numbers background, her greatest strength is bridging the gap between small business owners and the accounting professionals who work with them. She’s a former start-up founder and one of Practice Ignition’s 2018 Top 50 Women in Accounting, and she’s “an entrepreneur at heart.”

Only half of all small businesses use accounting professionals, but they’re now more efficient and affordable than ever before. Today, Twyla talks to us about some of their lesser-known benefits, like helping you craft a powerful 90-day forecast, and finding efficiencies when you feel squeezed. We also talk about why your relationship with your accountant should be great (not just good): you should feel like your business would flop without your accounting professionals.

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

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Join us on October 27th for 'From Firm to Fintech: A Candid Conversation with Twyla Verhelst, FreshBooks & Will Lopez, Gusto' a webinar brought to you by FreshBooks! click HERE to Register!

“We’re better together, and we go further together.” This is Kalani Hubbard talking about one of the perks of working with his wife Stefanie at their video production company Galaxy Visuals. Together, Kalani and Stefanie have worked on projects ranging from commercials to training videos; their most recent win was developing View and Chew, their own series with Amazon Prime.

On this week's episode, we talk to the Hubbards about how they merge their work-life with their marriage, how Stefanie's former role as a hairstylist still serves her when she's making media and the power of Google Hangouts. We also go high-level: why a big vision doesn't always need a big budget, and how optimism can sometimes mean asking yourself the right questions: how can I make that happen?

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

Guest- Stefanie and Kalani Hubbard

Galaxy Visuals

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“Your job is to make good decisions. Hopefully great decisions!” Rand Fishkin is one of the best SEO resources currently working: from his early days at Moz to the market research and audience intelligence firm SparkToro, to his popular Whiteboard Friday series, Fishkin knows how to max out marketing. These days, he's putting his considerable energy into helping small businesses thrive, and helping founders avoid the endless IPO chase.

Fishkin started as a college dropout who went into business with his mom. From these unconventional roots, he's grown into an SEO expert who has kept on top of the shifting trends and best practices. He shares with us how thoughtful market research helps boost small businesses, how un-creepy audience tracking really is, and how a bowl of bolognese helped him bounce back from losing a $13M deal.

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

GUEST-

Rand Fishkin- Website

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We’re celebrating Hispanic Heritage Month with Farah Sosa and Fred Villanueva, a pair of artists and entrepreneurs who combine their creative passions with a social mission and culturally-driven values. As Sosa, a concert photographer in the midst of a COVID pivot, explains: “I like humans from all over the planet.” Sosa's recent project, portraits of music venues that have been shuttered during COVID, explores the vital energy of live performance spaces.

Villaneuva takes a complementary approach to Ash Studio in Dallas, where his work has gradually shifted from corporate gigs to community-based projects. “I look at being an artist in this world as an area that’s full of opportunities.” He's also working towards improved equity and representation in the art world. We talk to Sosa and Villanueva about why their communities are one of their biggest business assets, why cultural representation matters, and how to take a practical approach to admin work and self-care.

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

Guests-

Farah Sosa- Farah Stop Website

Fred Villanueva - Ash Studios Website

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Mimi G doesn't have a typical success story, but you'd never know it from her four million social media followers or her million-dollar businesses (she has two of them!). Mimi is a former teen runaway and homeless single mom who turned her childhood interest in sewing into a thriving website, consulting business, and online learning hub. With Mimi G Style and Sew It! Academy, Mimi supports sewists of all levels in following their own design dreams.

In this week's episode, Mimi tells us about how an unshakeable sadness helped her realize her days in film and TV were behind her, and why she still schedules time for her hobbies—including sewing—despite being immersed in the business of it all day. We also talk about her Puerto Rican family's influence on her entrepreneurship, how she keeps tight relationships in business and life, and how offering a free service helped boost her income. Though her path to success might be full of unexpected loops, Mimi says, “it gave me a view of what I needed to do.”

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

Guest-
Mimi G.- Website

DIY Mask Video-LINK

Sew It Academy- Link

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“At the root of our work is education, civic engagement, youth leadership, and wrapping it up with a bow of creative problem-solving.” This is how Antionette D. Carroll explains her work on the Creative Reaction Lab, a nonprofit that trains Black and Latinx youth to redesign their own communities for better health and racial equity. We sit down with her to talk about Black Lives Matter, Diversity, Equity and Inclusion (DEI) initiatives, and white supremacy, and how it all relates to entrepreneurship in 2020.

Carroll gives us the background on what white supremacy actually is (and why you don't have to be white to perpetuate it), and why companies need to start paying for DEI work in their organizations. We also talk about code-switching, the importance of lived experience, and what makes a good ally. This episode is for all our listeners: we want to unpack the assumptions we make in business and in daily life to help create a more equitable society. As Carroll says, "I am continuing to learn and unlearn, and my discomfort is a good thing."

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

Guest- Antionette D. Carroll- https://www.antionettecarroll.design/

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Nicole Gibbons wants to change how we make our homes beautiful. “My aspiration was to be the next Martha Stewart,” she says, and she's on her way. The former PR rep has leveraged years of networking, blogging, media experience, and PR savvy to launch Clare, a direct-to-consumer business selling interior paint.

In this week's episode, Gibbons gives us behind-the-scenes access to how she landed an on-air hosting gig soon after leaving her day job (hint: it involves a lot of networking!), and how she used that opportunity to get VC funding and launch Clare as a brand. We also talk about the unexpected visibility of being a Black entrepreneur in 2020, how the pandemic enabled online shopping for unexpected products, and why networking and creating relationships really is that important. Clare is now taking aim on an industry dominated by legacy brands with nine-digit valuations, and Gibbons feels prepared. “A lot of time was put in before it was actually successful,” and she's now ready to go global.

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

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Welcome back to season three of I Make A Living! We're so excited to bring you another round of inspiring entrepreneurs and kick-butt creatives to help you figure out your path in this new normal. We're starting off with Jack Phan: investor, founder, advisor, and unexpected K-Pop influencer.

Phan got his start in medical school, but a detour into telemarketing (that was supposed just for beer money) ended launching a whole new way of marketing home improvements. Phan now mentors entrepreneurs to "find the why" behind what they're working towards. "Look for new ways of doing old things," he advises. For Phan, that includes using his million-follower Twitter account to facilitate meaningful one-on-one connections, and jumping into conversations about tech, AI, and yes, K-Pop. Phan also gives us insight into how the start-up community can—and should—be giving back. His newest project is Dollar For, a foundation that aims to relieve medical debt in the United States. We also talk about the connection between Gen X and Gen Z, what the "former introvert" misses about conferences, and who in his family is a former spy.

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

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In season 3, we are moving past survival mode and onto the future; a better and stronger business on the other side of a global pandemic. Each week you can listen to some of the world’s most successful entrepreneurs guide you through the small business solutions of today.

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From this episode, here are 3 ACTIONS to make your business more inclusive of sexual orientation and gender identity. If we’re looking to make lasting change, we need to continue the conversation around workplace intersectionality all the time - not just in reaction to current events.

Encourage use of pronouns - not just for queer employees but for everyone
Revise company policies - act in accordance with the law and your values on everything from workplace dress codes to hiring and firing practices
Rethink how you categorize your customers. Should you be making gender binary products or would your customers and business benefit from being more fluid.

This isn’t a one and done kind of thing - we’re all learning and growing together and so should our company policies. So keep thinking about diversity and inclusion and how you can be a leader and not a follower in business.

GUEST

Mina Gerges - Website

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Guest- Eric Williams The Silver Room

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Some of us want to be Lay's Chips—national! popular! instant recognition!—but Terry O'Reilly thinks we could learn a few things from Utz, Baltimore's hometown favorite chip brand that outperforms Lay's by a huge margin. In other words: small can be excellent. Terry O'Reilly is the host of the marketing podcast Under the Influence, and has 30 years of experience directing marketing for brands big and small.

In this week's episode, O'Reilly reminds us to put on our marketing hats at least once a week (hey, if it worked for Steve Jobs...) and experiment with boldness. “Does your idea make your hands start to sweat a little bit?” he asks; it's a clue that you're on the right track. He outlines his "Shish Kebab" theory of brand unity that you can start using today, and tells us why small businesses shouldn't get too wrapped up in what their competitors are doing.

He also takes questions from our #imakealiving audience about scaling businesses on a shoestring budget, how to use social media for market research, and how protect your business from toxic clients.

Guest

Terry O'Reilly- Website

The Apostrophe Podcast Company- Website

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While today's bonus episode focuses on the government programs set in the U.S., we believe that the experiences and tips shared by our financial expert guests are relatable to everyone, regardless of where you are located.

Thank you to our guests Phylecia an Oona and the 3 entrepreneurs who shared their experiences with us. Find them all below.

GUESTS-

Phylecia Jones - https://www.keepupwithmrsjones.com
Oona Rokyta, CEO and Co-Founder, Lance - https://www.justlance.co/covid19

ENTREPRENEURS

Julia Kline, Host of Solving Me Too Podcast - https://solvingmetoo.com
Meegan Czop, Owner of Great Lakes Yard - https://www.greatlakesyard.com
Ben Yee, Co-Owner of The Camera Department - https://www.thecameradept.com

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“Artists starving? There’s absolutely no reason for that.” Sonja Rasula is the founder of Unique Markets, a Los Angeles-based pop-up market showcase for artisans and makers. In this week's episode, she talks to us about her hands-on approach to training small business owners in the art of selling their art, why she launched Unique Markets during a recession, and why hitting the pause button now can help businesses recover down the road.

Rasula, who got her start in retail and later launched websites like NatGeo and FoodTV, understands the path between creating beautiful products and actually selling them. She ensures that her carefully selected vendors are trained on how to talk to shoppers and use tools like social media and branding to grow. Our conversation with her also includes the power of a drive-time epiphany, why she she's as busy during a shutdown as she was in her launch phase, and how she chose conscious consumerism in the first place.

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Allis Markham describes herself as “An artist with a really strong stomach.” She's the founder of Prey Taxidermy, a Los Angeles studio that serves clients ranging from luxury brands like Gucci to natural history museums all over America. We chat about her transition from Director of Social Media Strategy for the Walt Disney Company to running her own shop that's for the birds...and foxes...and armadillos.

Markham walked away from a six-figure job "explaining social media to boardrooms full of old white men” to follow her passion: creating beautiful taxidermy. Volunteering at the Natural History Museum of Los Angeles netted her both a mentor and a deeper understanding of her craft. She decided to take the plunge into full-time when she realized she could become the go-to taxidermist for the Los Angeles set: people who loved art tinged with luxury. We talk to her about the importance of a business motto, how teaching classes helps her fine-tune her practice, and why YouTube and outsourcing help her say yes to more.

Guest-

Allis Markham- https://www.preytaxidermy.com/pages/about-prey

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"Always have a hustle that’s paying the bills," says Steve Barnes, who knows plenty about hustle. Barnes, who got his start as a radio host and actor, combined his love of travel with a passion for content production to launch Barnes Creative Studios. Now, he travels the world shooting promo videos and VR for brands and destinations that make us want to book that vacation time.

In this week's episode, he talks to us about getting ahead of the pack with technology (and how working with camera drones ten years ago has led to an interest in VR), how to talk budget with a potential client without scaring them off, and why honing your listening skills and taking the time to build trust can help answer questions your clients aren't even asking yet. He also shares why driving for Uber (in a Tesla, no less!) isn't off-brand for him.

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Feeling a little...unmotivated? You’re not alone. With most of us working from home, we've lost some of our best productivity tools, and we might not even know it. In this week's minisode, Dr. Sahar Yousef of UC Berkeley chats with us about why setting clear cognitive boundaries between "work" and "everything else" makes a difference when all our days feel kind of the same.

She shares insights on how we can recreate and reinvent go-mode triggers for the home: setting up rituals that prime our brains to focus, using calendars to hype ourselves up subconsciously, and why we should never work from the couch. She walks us through "focus sprints," her recipe for conquering your to-do list and producing results. She's even got something for the kids: she talks about how homeschoolers need triggers and transitions into schoolwork just as much as their high-achieving parents. It's time to put your phone in a drawer, close all those tabs, and get down to business.

Guest- Dr. Sahar Yousef - Website

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In our special Masterclass episodes, we collect questions from real-life entrepreneurs at our live #IMakeALiving shows around the world, and ask our favourite experts to weigh in. From social media to scaling, from advertising to work-life balance, we get insights and guidance from folks who have been there.

When Pat Flynn was laid off from his architecture job in 2008, he wasn't sure what to do next. On a hunch, he developed a test-prep course for architects in training; over the next year, his course brought him over $200,000 in revenue. Flynn had seen the power of passive income. Instead of developing more courses, though, Flynn started training others on how to do the same.

"Truly passive income pretty much doesn’t exist," says Flynn, but he knows from experience that designing products that reward you for investing in and building them—and pay out time and time again—comes pretty close. In this week's conversation, we talk to Flynn about his three P's of mapping the market, why entrepreneurs should cultivate their superfans, and how bringing your human side into your business can improve everything from work-life balance to audience relationships. He also takes questions from past #IMakeALiving live-event audiences about interviewing guests on podcasts (and why you should ask “why?”), making the most of your passion-project time in a day-job world, and how to maintain our learning mindset even as we grow into our roles as thought leaders.

Guest- Pat Flynn

Website- http://smartpassiveincome.com/toolkit

Podcasts

SPI- https://www.smartpassiveincome.com/shows/spi/

Ask Pat- https://www.smartpassiveincome.com/shows/askpat/

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Notes: How does a mother of eight balance a thriving design career with a family the size of a baseball team? Well, for starters, she doesn't sweat the mess. Lisa Canning is an author, coach, and design expert, and this week, she joins us to talk about how entrepreneurs can get family life and work goals to align, even during a pandemic. She counsels us to let go of perfectionism, schedule deep-focus time, and to delegate household chores to the kids. Most importantly, she says this unique time can give us a chance to figure out what really matters—for both business activities and parenting—and to to loosen our grip on the other stuff. “The main goal for us, during this period, is forming greater connections with our families.”

Guest- Lisa Canning

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Do you find your brain buzzing when you look at your to-do list? Rich Jones knows that feeling. As host of the personal finance podcast Paychecks and Balances, creator of the podcast consulting business Showstarter, and as internal communications manager at Google, Jones has a lot on his plate. On this week's episode, we do a deep-dive on the tools he uses to make sure that everything gets done.

Jones suggests doing a bit soul-searching to figure out what's important to your business, and which tools might help—they might not be the ones everyone else is using. He uses tools like Slack, Evernote and Trello, along with automation software Zapier, in order to streamline communication and tasks. He's also thinking creatively about his networks: by introducing affiliates to his business model, Jones creates value for his ability to connect people with the products and services they need. Overall, he takes an experimental approach, and doesn't focus too much on mastering the programs he uses. As long as they're doing what he needs them to, it's good for his business.

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When you're trying to manage stress levels, tapping into simple strategies can make a big difference. In this week's minisode, John Kim of The Angry Therapist talks to us about why we're feeling worried, and what we can do about it. He touches on why getting some exercise can help structure your day, why a flow state can be the best kind of distraction, and how we can use this time to connect with audiences online. It's self-care for the shelter-in-place entrepreneur.

Resources:

Stages of Grief- https://psychcentral.com/lib/the-5-stages-of-loss-and-grief/

Guest:

John Kim's Website- Texts from the Angry Therapist

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Can you get your business to one million dollars in revenue without any employees? Not only is it possible, but Elaine Pofeldt has written the blueprint. As the author of The Million-Dollar, One-Person Business, Pofeldt tapped into years of experience writing about business, and running her own successful business, to give a guide to scaling up.

Pofeldt started as a staff writer, and launched her writing business in 2007 in order to balance the needs of her growing family against her bottom line. She spent the first two years of her independent business learning the ropes: being open to retainer arrangements, asking for deposits, and diversifying her services to include ghostwriting, coaching, and editing. “If you think of how you can be of service to people,” she says, “people will come to you.” We dive deeper on why saying yes to everything can sometimes backfire, why you should outsource work, and how to consider investing your profits back into professional development.

Guest

Elaine Pofeldt- Website

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Everyone knows something: whether it’s mortgage expertise or breastfeeding advice, we all have pockets of knowledge that make us everyday experts. Imagine being able to reach an online audience with that info, and charging them to learn it. Ankur Nagpal has this vision, so he created Teachable to help people earn money from what they can share with others.

Nagpal, whose background includes both real-life teaching and tech development, was a Forbes’s 2019 30 Under 30 Education honoree. This week, we talk to him about how to keep a relatively sane work-life balance (no all-nighters is a personal rule for him), how to hire and retain great employees (including an unorthodox stable of engineers), and how he’s come to recognize what Teachable really offers its clients. “We always say, No one wants your course,” he explains. “What they want is the outcome. They want the transformation. Your course is a way for them to get there.” He shares some of his knowledge with us, free of charge.

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On this week's episode, we chat with Michael Kass, the founder of Story and Spirit. Kass has tapped into his deeply varied background—think theatre, financial management, breath work and vision quests—and now uses the power of storytelling to help people and businesses transform.

The importance of storytelling as a business tool has been highlighted by Harvard Business Review and Google as a key skill for success. It goes past the “why” of the business and into the “who,” as in how who you are drives what you do. We chat about why, while telling those stories might take a big cultural shift, doing so helps democratize how we know and learn about each other and our work. In childhood, Kass was moved by the realization that fairy tales hardly ever included regular people; as an adult, he's working to change that, and making a successful business along the way.

We talk about the power of certification, the 80-20 rule, and defining success when you’re the first one on your path. Kass also walks us through the basics of a breath work exercise designed to help release emotion and get grounded when things seem turbulent.

Guest

Michael Kass- https://www.storyandspirit.org/michaels-story.html

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Gritty Birds Podcasting has been developing podcasts since 2014. Owned by producer and artist Jeni Wren Stottrup, Gritty Birds started as a music podcast interviewing label runners, lawyers, magazine owners, booking agents and more in the PNW community sponsored by Vortex Music Magazine. Wren had been deeply active as a singer, journalist, festival producer and in media sponsorship, with a desire to explore how create a successful career in music and audio production.

Guest- Jeni Wren Stottrup

Join Jeni for a free workshop- http://grittybirds.com/freefridays/

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NOTE: In light of the Covid-19 outbreak and the current landscape for entrepreneurs, and small business owners, we are working hard to bring you more resources and conversations to get you through these difficult times. Stay tuned for some special episodes in the coming days and weeks. Stay strong, you are not alone! Follow our community at facebook.com/groups/imakealiving

We know you like podcasts, but have you ever thought about starting one? On this week's episode, we talk to two women with ample experience in the field. Jeanine Wright is the COO of Simplecast, which helps launch podcasts, and has a special focus on analytics. Fatima Zaidi co-founded Quill, which connects podcasts professionals to folks with a dream in order to get a project off the ground. We get the inside story on what goes into podcasting after the microphone is turned off: podcasts are one of the most powerful marketing tools available to companies, but they also need to find their own path to success. As Zaidi asks, “What kind of brand do you want to be seen as?”

We also talk to Wright and Zaidi about their experiences on opposite ends of the investor spectrum. Zaidi weighs on the value of running a bootstrap operation, while Wright shares her three criteria for considering an investment opportunity. Both also offer insight into their experience as women in a male-dominated sector, where there are opportunities to break new ground and create a work-life balance that works for you.

Guests-

Jeanine Wright- Simplecast

Fatima Zaidi- Quill

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Lisa Carmen Wang has spent a lot of time falling and even more time getting back up. As a rhythmic gymnast, she took home Pan-Am Games gold and was the US National Champion for three years running. In 2015, she founded SheWorx, a platform devoted to launching and scaling female-headed businesses. In this week's episode, she talks to us about her newest project, The GLOW.

“How do you get your foot in the door when you aren’t born in a rich family and you aren’t born into these Silicon Valley circles?” she asks. SheWorx provides part of the answer: networks of mentors, peers and allies who can help guide and amplify women's voices in the entrepreneurial space. But Wang knew that the business side was only part of the answer. The GLOW—which stands for The Global League of Women— takes a holistic approach to female success, training women to love their voice, their bodies, and their spirit. The end result? Boosted confidence and what Wang calls "enoughness." In our chat with Wang, we touch on the importance of resilience, how men can be great allies in business (and in life), and the power of a good self-care ritual.

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James Beard award-winning restaurant, Guelaguetza in Los Angeles’s Koreatown, puts Oaxacan cuisine and culture at the forefront of today’s dynamic culinary scene.

Bricia Lopez - Bricia Lopez is an entrepreneur, cultural ambassador, and a key figure in Los Angeles’ gastronomic scene. The New Yorker called Bricia the “Queen of Mezcal.” This year she opened Vegas’s first ever mezcal bar – ‘Mama Rabbit” inside The Park MGM. Launched the Super Mamas Podcast with Paulina, that has become a lifestyle media company, complete with annual events, and corporate partnerships with major brands. Bricia Lopez was appointed by the Mayor of Los Angeles to the Board of Convention and Tourism Development on March 2019.

Paulina Lopez-Velazquez - CFO and Director of Catering and Special Events. Super Mamas Social, a parenting festival that takes place yearly in Downtown Los Angeles. Paulina currently sits on the Board of Directors of City Charter Schools, a K-12 Los Angeles Based School organization that promotes diversity, culture, and bilingualism. Most recently, Paulina was awarded Women of The Year in the Council District 54, by Assembly Member Ridley-Thomas.

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Something we've heard a lot from the female entrepreneurs at our I Make A Living live events, is that so many of you have trouble with sales. Even though we know what we have to offer we sometimes feel uncomfortable asking for what we’re worth.

Carmelia Ray is an internationally acclaimed matchmaker for high achieving men and the quality women they’re searching for. She’s also a renowned TV personality from Mom Vs. Matchmaker, The Real Housewives Of Toronto, and A User’s Guide to Cheating Death (Fall 2018).

A frequent media contributor, Carmelia’s advice and expertise have been featured in notable outlets including AskMen, Variety, The Hollywood Reporter, OK! Magazine, Global News, Cupid’s Pulse, The Marilyn Denis Show, CHCH News, Elle, Playback, and countless others. Her wealth of wisdom and experience has also attracted in-demand partnerships with major dating companies including Match.com, Lava Life, Instant Chemistry, and more.

Carmelia is a great example of selling confidently and being bold about getting paid for the value she offers others.

Here’s a summary of what Carmelia taught us today:

Focus your sales pitch on the value proposition for your clients rather than minutia of the product or service and try not to sound desperate even if you are
Get organized and plan as much as you can
Always incorporate time with family and loved ones into your schedule, no matter how busy your business gets
Network like you would make friends - the more relationships you build, the more robust your sales network
Collaborate, Collaborate, Collaborate

See what Carmelia is up to at CarmeliaRay.com or on social media @carmeliaray.

Guest

Carmelia Ray- Website

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Jewel Burks Solomon is an Atlanta-based entrepreneur who was recently named Head of Google for Startups in the US. Jewel is no stranger to startups and entrepreneurship; she launched Partpic, a visual recognition technology company in her mid-twenties, and had it sold to Amazon in 2016. She was also named on Forbe’s 30 under 30 list. Jewel is also managing partner at Collab Capital, an investment fund designed to connect black founders to the financial and social capital they need to build profitable businesses.

Jewel’s dream is transforming so many realities for new innovators in entrepreneurship, and we can’t wait to see what Google for Startups does under her leadership.

Here are a few big takeaways from Jewel’s story:

Don’t wait for people to believe in your idea and fund it - if you build it (and it’s good), they will come.
Be smart about networking - put your ideas in front of the right people and nurture relationships with them
Selling your company is not always the fantasy it’s made out to be, map out what your life would be like after you’re acquired and see if that’s what you really want
Surround yourself with other people who are doing the kind of work you want to be doing and who’ll inspire you to keep going
Most of all - don’t let your story, the place you live, or the color of your skin, define what’s possible for you

In honor of Black history month, we thank Jewel and the many black entrepreneurs who have paved the way for other innovators to be brilliant and brave.

Guest

Jewel Burks Solomon- https://www.inc.com/magazine/201904/yasmin-gagne/partpic-amazon-jewel-burks-solomon.html

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Since 2005, A Slice of Brooklyn Bus Tours has been showing people around Brooklyn.

The company was started by Tony Muia, a proud native Brooklynite who always loved showing people around his beloved hometown.

Tony slowly starting doing informal tours for those same folks when they came to visit NYC, driving them around in his car. Soon, their friends and families would visit NYC and ask Tony to do tours for them so he did them as a side hobby while still working his regular job.

In 2004 Tony decided to switch careers after watching NYC tourism increase. However, it mostly focused on Manhattan and Tony felt that Brooklyn had enough amazing foods, neighbourhoods, landmarks and movie locations that it needed its own tour. And that’s when he decided to launch A Slice of Brooklyn Pizza Tour in 2005 with other tours that followed.

What started as a hobby turned into a family business and today he has 3 popular tours that run year round and have proudly introduced over 90,000 people to Brooklyn.

Some people say don’t make your passion your business, but you’re in a business that is inspired by your passion, you have to dive in with both feet.

Tony designed this business around his life, brought in the people who were closest to him and got them invested in his idea, and never looked back.

Here are the key takeaways from Tony’s Story:

Go to where your audience is - If you want to entice people come to Brooklyn, you might need to pick them up in Manhattan. Which figurative borough are your customers hanging out in right now? Get it?
Don’t be afraid to ask questions - your mentors and supporters can help steer you in the right direction.
Delegate, delegate, delegate - you don’t need to do it all!
Leverage press to grow your business
Make friends with your customers

That’s what’s kept Tony in business for 15 years.

Guest

Tony Muia and Ronnie from A Slice of Brooklyn -https://asliceofbrooklyn.com/

Disclaimer: The views and opinions expressed on this podcast are those of the guests and production team and do not necessarily reflect the official policy or position of '2ndSite.INC dba FreshBooks, its employees or affiliates.'

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This month, we're celebrating Valentine's Day by speaking to couples who inspire us by building strong partnerships - partners in life, partners in business, and partners in their community.

We sat down with Angie Myung and Ted Vadakan, a husband-and-wife team who have artfully mastered the feat of finding their tribe through their brand Poketo.

The name Poketo (pronounced "poh-keh-toe") stems from the mispronunciation of "pocket" by Angie's grandmother. It tied in perfectly with the first product ever created under Poketo: a series of artist wallets that fit right in your pocket—and Ted and Angie just loved the way it sounded.

Poketo has worked with brands and companies like Nike, MTV, Disney, Target, Nordstrom and MailChimp, museums like MOCA, the Guggenheim, the de Young, and SFMOMA, and has collaborated with over 200 international artists, creating exclusive products that reflect its philosophy of "Art for Your Every day."

Ted and Angie are a great example of two partners who set the tone for their business. Poketo is all about collaboration, community, and partnership - something that is ingrained in their personal lives and amazing love story.

They gave us a lot to keep in mind:

Find your community and keep them close
Play to the strengths of your partnership
Stop worrying so much about your business’ competition and instead, focus your energy on collaboration and staying ahead of the game

Guests

Ted Vadakan and Angie Myung from Poketo- https://www.poketo.com/

Resources

Maslow's Hierarchy of Needs- https://www.simplypsychology.org/maslow.html

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"I steal my kid's vitamins" isn't something that would normally lead to an a-ha moment, but the Goulds aren't your usual entrepreneurs. A couple for ten years, the Goulds are practiced business leaders who are part of the vanguard of the wellness industry: Gordon Gould crunches the numbers, and Courtney Nichol Gould focuses on the human side. Together, they're the power couple behind SmartyPants, the vitamin gummy brand launched in 2011 that now includes products for children, adults, and even pets.

The Goulds practice holistic wellness in their work and their home life: we talk to them about their exercise regimes, why they used a coach to launch their business (and to get on the same page about parenting), and how the lines of communication stay fresh when, as Gordon says, "there’s no leaving it at the office, because the office comes home with you a lot of the times." They also give us valuable info on the world of venture capital, where big visions can lead to big payoffs.

Guests:

Courtney Nichols and Gordon Gould- Smarty Pants

Resources:

INC Magazine on hiring a business coach- https://www.inc.com/young-entrepreneur-council/8-convincing-reasons-you-should-hire-a-business-coach.html

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In our special Masterclass episodes, we collect questions from real-life entrepreneurs at our live #imakealiving shows around the world, and ask our favourite experts to weigh in. From social media to scaling, from advertising to work-life balance, we get insights and guidance from folks in the know.

In our first Masterclass episode of the season, we are delighted to talk with Peter Shankman. He has been a vocal advocate for neurodiversity in the workplace, he is the founder of the journalism tool HARO, and is a successful writer, speaker, podcast host, and entrepreneur.

In our conversation, we cover a wide ground - not surprising, given that Shankman has leveraged his own ADHD into a better understanding of his complex body chemistry and physical needs. (He tells us how to write a book in 34 hours - it involves booking a flight to Tokyo!) He also answers questions from our #imadealiving live events about why authentic social media is best, why listening to your audience will help grow your business, and why you - yes, you - should charge more in 2020. We take our advice from a man who says that jumping out of a plane gets him into work mode, don't you?

Guest:

Peter Shankman- Website

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A pivot can be a powerful thing. Tina Essmaker started as a social worker with a side project, a Kickstarted magazine she founded with her husband. But when her marriage ended, she had to re-evaluate: stay with the magazine, or start something new? She decided to tap into her skills as a social worker and her connection to the creative community to re-launch as a creative coach. In this week's episode, Damona talks with Essmaker about how she transitioned from publishing into a self-created role where she helps creative workers identify and stick with their goals.

Essmaker offers concrete tips for people considering a shift from one path to another, and encourages listeners to consider the "emotional balance sheet" of their lives. (And Damona gets a gold star for her ability to describe her work concisely - would you get the same?) "It’s just a continual act of faith, that knowing what I’m doing is valuable and it’s needed, and then trusting that clients will come to me," says Essman, who now works as a coach, a speaker, and a writer.

Resources

To learn more about Tina and her services go to:
https://tinaessmaker.com

Word of Mouth Marketing- Article
https://www.bigcommerce.com/blog/word-of-mouth-marketing/

Nielsen Report
https://www.nielsen.com/us/en/insights/article/2012/consumer-trust-in-online-social-and-mobile-advertising-grows/

If you like our show, please let us know by rating and reviewing it on whatever platform you listen to it. 5 reviews help us grow our audience and reach!*

To learn more about FreshBooks and receive an exclusive offer go to
www.freshbooks.com/imal

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Welcome to Season 2 of the I Make a Living Podcast. We are excited to kick off 2020 with a brand new season and incredible conversations with some of the most influential and successful entrepreneurs in North America and the world.

As a television producer, Brant Pinvidic has pitched a lot. Like, a lot. In his 15 years in the entertainment industry, Pinvidic has had the chance to get his pitching practice down to a science. In his new book, The 3-Minute Rule, he lays out the basics of what makes a great pitch, and where folks fail. His challenge to readers is to get their pitches down to a crystal-clear three minutes, and on this week's episode, we get the inside scoop on how to nail that process.

"They don’t want to hear any of the fluff and pageantry. They just want to get to the point," Pinvidic says. He gives us some simple ground rules for pitching, including how to avoid too much promotional energy, how to separate opinions from facts, and how to come back from 99 rejections to nail that 100th pitch. His approach has allowed him to become a pitching guru outside the entertainment industry, and he now provides support to a broad range of businesses. "Simple is the new sexy," he says; sounds like three minutes in heaven to us.

Guest: Brant Pinvidic

Book: 3 Min Rule

References:

FreshBooks exclusive offer: www.freshbooks.com/imal

Damona Hoffman: www.damonahoffman.com

Tony Robbins Cold Plunge- https://www.youtube.com/watch?v=_6YtmPo9pxg

Resources:

Transcript- https://www.freshbooks.com/podcast/pitch-your-business-brant-pinvidic

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Season 2 of the I Make a Living Podcast launches on Monday, January 13th. Follow us as we continue to explore what it takes to be a business owner in today's world. Our host, Damona Hoffman, will take you on her journey as she sits down with some of North America's most interesting and successful entrepreneurs.

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The idea of success has many faces and iterations, most of us relate success to financial freedom or fame, but when you are an entrepreneur, success can mean much more than that. Who knew that waiting in line for hours on end could turn into full fledge operation, that someone could find joy in dressing up as Batman just to bring joy to tourists or that selling finger-painting art on Facebook for $50 could turn into a million dollar business or that anyone would pay for literally garbage picked up from the streets?

The entrepreneurs that we talk to on this episode have all something in common; their business ideas broke the paradigms of conventionalism and defied the odds of 'success'.

Robert Samuel from Same Ol' Line Dudes found inspiration while waiting in line for a new iPhone; Iris Scott had a dream of being a full-time artist, so she dropped everything and moved to Thailand where she could sell her art online while solely focusing on her craft. Justin Gignac felt challenged by a former colleague on the importance of packaging when selling any product. He took that challenge by literally selling 'nicely packed garbage' to people over 140 countries. We also talk to several NYC street performers, from subway musicians like Leonel Lorador to the very popular street troupes that stop pedestrians in Times Square to a journalist by trade but Batman impersonator by passion.

Throughout this season we have learned that being an entrepreneur is not an easy job, it can be an isolating and life-consuming journey for many, but we also met incredible people that have found a way to make it work. To achieve success, whatever success means to you, you must understand the ins and outs of being self-employed and the very particular sets of challenges that will arise when you are your boss.

We hope that throughout these episodes, we have left something valuable and meaningful to you by sharing the stories of real-life entrepreneurs who have figured out how to balance life and work, be a little more productive or dealt with very particular issues that many of you shared with us as we traveled the country with the live event.

Stay tuned as we gear up for a new season. We will be back soon with more stories, more inspiration, and useful tips from real-life entrepreneurs.

Happy Summer!

Guest Speakers (in order of appearance)

Robert Samuel- Same Ol Line Dudes (also Jeff and Jerry who waiting in line for us, thanks!)

Iris Scott- Finger-Paint Artist

Leonel Lorador- Subway Musician

Batman of the People- Instagram

Joshua Reyes- Times Square Acrobat Troupes

Justin Gignac- Working x Working & The Garbage Project

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The statistics aren’t too friendly when it comes to the longevity of small businesses. Nearly 50% fail at the five year mark. But, how does knowing this statistic help you? Most people can talk about failure ethereally—hardships builds character, you can’t succeed without failing, you know, those kinds of phrases. But, when it comes to us, you, specifically failing, you don’t want to and often times we do everything in our power to avoid thinking about the possibility of it. But, accepting that failure, on some level, happens, that can actually be one of the best things you can do as an entrepreneur. If you know that failing is a part of the journey you can prepare yourself for it. It’s the unknown that makes even the consideration of failure unfathomable.

Sometimes our past failures haunt us and the fear of our future failures paralyzes us. These obstacles that get in the way of moving forward are in our head. This is the reason why metal health really is an important topic and is actually the bulk of this conversation. You have to acknowledge these obstacles are real in order to begin dismantling them and face your fears. Doing this requires vulnerability which brings this conversation full circle. And, in the words of Brene Brown “Vulnerability is not weakness, and the uncertainty, risk, and emotional exposure we face every day are not optional. Our only choice is a question of engagement. Our willingness to own and engage with our vulnerability determines the depth of our courage and the clarity of our purpose”

Guest Speakers

Sam Rosen- Founder and Entrepreneur

Michelle Horton- Professional Therapist

Center Stage

Trained by Trell - Instagram

“To be featured on Center Stage, send us a voice message!”

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Coming up with problems without immediately trying to fix them is a lot harder than you’d think. Our minds really are trained to find solutions. But, throughout this episode we focus the most on the beginning two steps—

Defining the problem
Confirming that it actually is a viable problem.

The biggest take away from this whole conversation is to start at the beginning, with the problem—and spend a lot of time there. The last thing you want to do is create a solution that no one wants or is willing to buy into. We also discover that starting a startup is not out of reach.

The steps that Seth gives us are actionable. While it will take a lot of hard work and diligence, you don’t necessarily need a big budget to start. You really just need a group of people who have a problem.

Guests

Seth Radman- Co-Founder at Crescendo | Tech Entrepreneur | Startup Advisor

Center Stage

Charla Ruschelle- CR Clothing Co.

“To be featured on Center Stage, send us a voice message!”

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Episode Guests

Beverley Cheng- Born To Sweat

Zoey Masters- Instagram

Jeremy Bailey- LinkedIn

Center Stage

Christopher Jones- SeeJonesWork

“To be featured on Center Stage, send us a voice message!”

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Every business starts somewhere before it's a well-oiled machine. Sometimes it's at your kitchen counter in-between your part-time jobs. The whole concept of growing your business means it was small at some point.

This season, we've seen that it takes a lot to start a business from the ground up. Not everyone is cut out to be an entrepreneur. It takes a lot of diligence and hard work to get any business off the ground. It's not for the faint of heart. There are a lot of ups, downs, failures, and successes. Sometimes, it's so important to hear what the journey has been like for others, especially, from those who are a little further along on the journey than we are. That's the reason for today's episode. The journey for any entrepreneur can be a complicated one, but, we learn from the growing pains that we encounter. And, hopefully, they make us better business owners.

The growing pains of building your business are real. Determination is one of the main themes that we recognize in Kristen's story. She sacrificed a lot to get the company off the ground— time, money, comfort. But, to her, the business was worth it. And, it's paid off so far. Being your own boss takes determination and grit. Kristen is an excellent example of who will make it in this competitive world of entrepreneurship,someone who is smart and eager to learn. If you're willing to learn, sacrifice, and put in the hard work, then that might be you too. Knowing the road is going to be rough can be discouraging. But, try taking a page from Kristen's book. Let the challenge be what fuels your determination to keep moving forward.

Episode Guests

Kristen Pumphrey- PF Candle CO.

Center Stage

Torin Regier- Keg Shoe

“To be featured on Center Stage, send us a voice message

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For a while now, we have been planning an episode on diversifying your business. We wanted to document the story of an individual who had just started their business and what it looked like to establish diversification in the initial steps of development. But, the story we ended up capturing was much more specific; someone who was forced to diversify due to external issues out of their control. So, we briefly discuss the general idea of diversification and offer a few tips on starting your business but the meat of this episode is really on: pivoting. Having an idea, a set plan for your business and finding out it's not going to work for some reason or another.

So, back to the story of us choosing someone from the IMAL event. We didn’t know how it was going to go but the whole process in finding this one person to feature sounded fascinating and definitely worth recording.

Episode Guests

RM Harrison- our business coach for this episode. RM is a career and business coach based in Austin, TX. She has helped a lot of people "snap out of frustration and burnout and get them fired up again about the work they do." To learn more or get in touch with RM here.

Meesha Farzaneh

Thank you to Meesha for sharing her story with us and being part of this experiment. To find more information about her business go to her website here.

Center Stage

Thanks to Juan Bendana for submitting his story! If you want to learn more about this incredible entrepreneur, visit his website here: https://www.juanbendana.com/. To be featured on center stage, send us a voice message!

Disclaimer: The views and opinions expressed on this podcast are those of the guests and production team and do not necessarily reflect the official policy or position of 2ndSite.INC dba FreshBooks, its employees or affiliates.

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Productivity is important as an entrepreneur but so is the balance between your personal life and your work life. If you’re not careful you can easily burn yourself out, harm personal relationships, and actually become less productive because you’re not giving yourself the space to rejuvenate—which is often times why people are most productive. It’s a balance. The Western world is in a bit of an epidemic these days. Some of the leading organizations in today’s world give their employees unlimited PAID time off. Which sounds absolutely crazy…but, according to the research done by Sage Business Researcher, many people in these businesses are taking even less vacation time. And, those who do have a standard amount of paid time off, aren’t using it all. According to a 2017 report done by the US Travel Association, there are 705 million unused vacation days annually. Taking time off is essential in balancing work and life.

And, if these employees find it difficult taking paid time off how much harder would it be for entrepreneurs who aren’t getting paid for their vacation time?

Our featured guests Lisa Canning and Espree Devora share with us their insights, motivations and tips and tricks to accomplish a more balanced work routine so they can have more time for life.

Our Guests Links

Lisa Canning's website and book page:

https://lisacanning.ca/my-book2/

Espree Devora's podcasts:

http://podcast.womenintechshow.com/

http://podcast.wearelatech.com/

Resources:

Work-Life Balance research studies

https://www.ustravel.org/research/state-american-vacation-2018

https://www.ted.com/topics/work-life+balance

https://www.forbes.com/sites/forbestechcouncil/2018/01/25/entrepreneurs-need-to-pay-more-attention-to-work-life-balance-heres-how/#47780ded46b3

https://www.entrepreneur.com/article/311414

https://www.tci-thaijo.org/index.php/IJBS/article/view/521/pdf

http://businessresearcher.sagepub.com/sbr-1863-102641-2779724/20170508/short-article-more-companies-offering-unlimited-time-off

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Episode 05“It’s all about the money....and taxes.”

Today’s episode is about one of the most dreaded yet necessary pains every entrepreneur has to endure...tax season. No matter how big or small your business is, taxes are always going to be somewhat complicated, confusing and could create a lot of troubles if not dealt with appropriately. We are here to help!

Our featured guest, Paco de Leon is a self-proclaimed ‘money nerd,’ she founded “The Hell Yeah Group” to help small creative entrepreneurs better manage their finances. Paco shares valuable advice and tips on how to organize your finances, so you are always in control of them and not them in control of you.

As we were developing this episode, we realized that Darbi was not exempt from the familiar “wait till the very last minute” attitude that a lot of freelancers or new business owners have when it comes to taxes, so we decided to document her journey into filing taxes as an entrepreneur. For that, we invited Chicago based accountant Yolanda O’Neal, to sit down and help Darbi figure out her tax situation for 2018.

As you will hear from both Paco and Yolanda, taxes are indeed complicated, the tax code is confusing and its always changing but they both agree that it is not your job to keep up with it, that is what your accountant is for. Accountants are a vital role in every small business owner and a solid piece of advice...find a good one!

Your job is to stay on top of your daily transactions, your bookkeeping, your invoices, expenses, and other day-to-day operations. Doing that in an organized and consistent form will alleviate a lot of the pain and paperwork when tax season arrives.

We genuinely hope this episode is helpful and you find some tips on how to better manage your finances so that future tax seasons are as painless as possible.

Happy Tax Season!

Guests Paco de Leon- The Hell Yeah GroupYolanda O’Neal- O’Neal Consulting

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Episode 04 "Being a Female Entrepreneur PT. 2"

Welcome to the second episode of our 2-part series in honor of “Women’s History Month.” On this episode, we explore the role of equity in the female entrepreneurial world. We hear from 2 female business owners who share their experiences and journies to success.

Equality. This is the conversation we’re having during women’s history month. However, to give this topic justice, we need also to consider what part equity plays. Equity is the varying levels of support need to obtain true equality for people from different backgrounds.

Based on how you self-identify, the amount of equity needed to accomplish equality may vary. In our last episode, we covered a pretty broad view of what it’s like to be a woman in the entrepreneurial world. However, what we didn’t include is how the experience can vary from person to person.

Join us as we listen to the stories behind two successful female business founders: Kweighbaye Kotee and Laura Laban. They share their experiences honestly and openly, and the role their particular intersections had on their path to becoming successful entrepreneurs.

To close off this series, we are excited to include award-winning poet, writer, and activist Staceyann Chin’s, "Equality Now"; a spoken word piece she wrote for the National Equality March in 2009.

Episode Guests

Kweighbaye Kotee- Founder and CEO of the Bushwick Film Festivalhttps://www.bushwickfilmfestival.com

Laura Laban- Co-Founder and CEO of Infinite Flight LLChttps://infiniteflight.com/

Citations and Resources

Kimberle Crenshaw’s TED Talk on Intersectionality

https://www.youtube.com/watch?v=akOe5-UsQ2o

Equality and Equity- Context and Differencehttps://www.ywcalgary.ca/news/equity-v-s-equality-whats-difference/

https://www.forbes.com/sites/ellevate/2017/09/14/why-we-need-gender-equity-now/#74eff0577a24

Disclaimer

The views and opinions expressed on this podcast are those of the guests and production team and do not necessarily reflect the official policy or position of '2ndSite.INC dba FreshBooks, its employees or affiliates.'

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Episode 03- "Being a Female Entrepreneur PT1"

Welcome to a special 2-part series in honour of Women's History Month. We take a look at the entrepreneurship world from a female perspective.

Being a woman in the small business world isn’t easy. Even if you don’t self-identify as a woman, because of recent media movements, you can probably gather that it’s not exactly a walk in the park for females. There’s been a shift, on a large scale, in society recently. The #metoo and #timesup movements have brought some incredible awareness to the issues of inequality through mass media. It’s no longer taboo to discuss experiences. There is a power behind the voices that speak up. But, these developments are relatively new when you think about it.

How is the gender gap being addressed and how can women learn to negotiate equal pay in the freelancing world. We also look at the role of men in the fight for a more equalitarian and inclusive society.

Episode Guests

Rubina Shaikh

Thanks to Rubina Shaikh for sharing her experience as a female entrepreneur and freelancer. To learn more about Rubina go to https://www.linkedin.com/in/rubinashaikh/

Kathlyn Hart

Thanks to Kathlyn for a genuinely insightful conversation on how women can build confidence and negotiate equal pay in the freelancing and entrepreneurship world. To hear more about Kathlyn, her coaching services and all the fantastic work she does, check out her Podcast: "The Kathlyn Hart Show."

http://www.kathlynhart.com/podcast/

Rachel Wynn

Thank you to Rachel for her insights on feminism and the role of men in the fight for equality. Rachel is a "self-proclaimed feminist" who leads The Feminist Founder group. To learn more and join the ongoing conversations go to https://www.feministfounder.com/

Rachel is also the CEO of Starlight Social. If you need Social Media management for your site or business, go to https://www.starlightsocial.com/

Episode Citations

Here are the links to some of the citations we had and resources on feminism, gender gap and women's rights.

1) CBS and Refinery 29 poll on feminism amongst Millenials https://www.refinery29.com/en-us/midterm-election-women-dont-identify-as-feminists

2) the #metoo Movement

https://en.wikipedia.org/wiki/Me_Too_movement

3) Time'sUp Movement

https://en.wikipedia.org/wiki/Time%27s_Up_(movement)

4) https://www.telegraph.co.uk/women/life/1918-vs-2018-13-things-women-couldnt-do-100-years-ago/

5) https://www.huffingtonpost.ca/entry/rights-women-have-gained-since-earning-the-right-to-vote_us_57e9ed33e4b0c2407cd93434

6) https://www.freshbooks.com/press/data-research/women-in-the-workforce-2018

Center Stage

Thanks to Martha McCallum for submitting her story! If you want to learn more about this incredible entrepreneur go to https://marthashelihikes.com/

If you want to apply to be featured on Center Stage go to www.freshbooks.com/podcast

Disclaimer

The views and opinions expressed on this podcast are those of the guests and production team and do not necessarily reflect the official policy or position of 2ndSite.INC dba FreshBooks, its employees or affiliates.

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The average entrepreneur works over 60 hours a week. That’s 20 plus hours more than the traditional 9-5er. Are you using your time wisely? Explore how other self-employed folks choose to approach their productivity. Hal Elrod, best-selling author of the Miracle Morning book shares with us why morning routines can boost your productivity throughout the day. Hal is a wealth of knowledge when it comes to morning routines and jumpstarting your day in the best way possible. If you want to read one of his books and/or find out more about Hal go to: https://halelrod.com/".

We also talk to 3 different entrepreneurs who work from different places: home, coffee shops and co-working spaces. What is the difference? What are the pros and cons of each of them? Join us as we take a deep look at how the space surrounding you can help you become a more productive individual.

Center Stage

``` Thank you Michael Der for sharing your center stage story. To find more about Michael go to, https://www.michaelderphotography.com/]( https://www.michaelderphotography.com/) To be featured on center stage go to: www.freshbooks.com/podcast

```

Episode 2—Citations

1. What & What Not to Avoid. #7 Productivity Hacks for Entrepreneurs href="https://www.entrepreneur.com/article/323404">https://www.entrepreneur.com/article/323404

8 Essential Productivity Tips for the Busy Entrepreneur

https://www.inc.com/john-discala/8-essential-productivity-tips-for-busy-entrepreneur.html 3. Is Noise Always Bad? Exploring the Effects of Ambient Noise on Creative Cognition

https://www.jstor.org/stable/10.1086/665048?seq=1#metadata_info_tab_contents 4. It has been my observation that most people get ahead during the time that others waste. -Henry Ford

brainyquote.com 5. Entrepreneurs work over 60+ hours a week (infographic)

https://www.entrepreneur.com/article/285079

Our next episode will be a very special episode in honor of International Women's Day! Make sure to subscribe to get the latest episodes as soon as they become available.

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Episode 01- Present and Future of Entrepreneurship

Why are people turning to self-employment in the current economy?

Alex, a freelancer who thought jumping ship and starting her journey would be a lot simpler than it turned out to be. A whole new set of challenges arise once someone decides to venture into entrepreneurship and a lot of times, those challenges are not-so-common knowledge.

We talk to some FreshBooks folks who share some interesting numbers and data on the present and future of entrepreneurship.

All these experiences, insights and pain points collectively motivated us to create this podcast, and they set the tone to all the incredible conversations we are about to share with you.

Welcome to #imakealiving!

Thanks to Alex Rathbun for sharing her experiences in such an honest and vulnerable form. For more on her go to https://www.brightlyalex.com/

Thanks to Carly Moulton and Dave Crosgrave from FreshBooks for sharing their data and reports insights with us. To find more about the Annual Reports FreshBooks publishes on self-employment go to https://www.freshbooks.com/press/data-research

Center Stage Each episode, we will devout the last few minutes to highlight entrepreneurs and freelancers from our audience who are doing great and/or unique things out there.

For our inaugural Center Stage, meet voice-over actress Debbie Irwin AKA "The voice of the Statue of Liberty" amongst others.

To learn more about Debbie go to: https://www.debbieirwin.com/

I Make a Living: Recent Episodes

FreshBooks, Damona Hoffman, Francisco Arizmendi