21 Hats Podcast

21 Hats Podcast

The 21 Hats Podcast presents an authentic weekly conversation with small business owners who are remarkably willing to share what’s working for them and what isn’t. Unlike many business podcasts, which tend to talk to highly successful entrepreneurs whose struggles are in the past, the 21 Hats Podcast features a rotating cast of business owners who are still very much in the trenches fighting the good fight. Every week, our regulars gather to talk about the kinds of important issues many owners won’t even discuss behind closed doors: whether their businesses are as profitable as they should be, whether they are willing to give up some control to an investor in order to grow faster, why they had to lay off employees, how they wound up with way too much inventory, why they don’t have a succession plan, and even why they are concerned about their own mental health. Visit 21hats.com to hear all of our podcast episodes, read episode transcripts, and learn more. The show is produced by Jess Thoubboron, founder of Blank Word.

Episodes

November 14, 2025 30 mins
Yes, says Gene Marks, it’s easy to make fun of all of the ways in which AI chatbots can fail (don’t even think about asking them to create an image of a Yorkshire Terrier hitting a homerun), but that’s no excuse to sit on the sidelines. Get the paid version. Get some training. Get your employees some training. And get to work. On what? Gene gives some examples of his favorite use cases.
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This week, in Episode 270, we dig into employee ownership with two people who’ve lived it: Kris Maynard and Justin Jordan of Cathedral Holdings, a 100-percent employee-owned ESOP since 2011. Kris and Justin are enthusiastic proponents of ESOPs, but they’re also candid about what can go wrong. Yes, ESOPs come with big tax advantages. But the transaction can be complex. The debt can fundamentally change the risk profile of a business...
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This week, Julian Scadden explains how the organization he runs, Nexstar Network, helps the owners of plumbing, HVAC, and electrical firms become better business owners. Along the way, he discusses the challenges home-service businesses are confronting, why Nexstar is member-owned (and what that means), and an intriguing decision he made recently to part ways with the 30 percent of his members who are private-equity backed. Those m...
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November 4, 2025 43 mins
This week, in Episode 269, we welcome Ted Wolf, co-founder of Guidewise, as the newest regular member of the 21 Hats Podcast crew—and Ted arrives with a pretty good story. Back when he was building his IT staffing business with his brother, a senior employee walked out. But he didn’t walk out alone—he took key employees, key accounts, and 40 percent of the company’s revenue. At the time, Ted thought it was the worst day of his busi...
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Josh Patrick’s first act was building and eventually selling a successful vending-machine business. His second act was building a thriving consulting practice in which he helped other business owners learn the lessons he’d learned the hard way. In our latest Dashboard episode, Josh, a cancer survivor whose cancer has returned, is exploring two experiences—retirement and death—that he believes most owners are ill-prepared to confron...
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This week, in episode 268, Jay Goltz, Lena McGuire, and Liz Picarazzi discuss a common concern: When does it make sense to buy a building for your business? Under the right circumstances—say, with an SBA loan, a good location, and a little luck—the real estate could end up being worth more than the business itself. But what if the business is just getting started? Or what if the owner is nearing retirement age and may not be around...
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This week, Greg Shugar, owner of Beau Ties, a men’s accessories business, explains how the tariffs have the potential to destroy the very businesses they are supposed to protect. As Shugar points out, President Trump has said all along that if you make it here, you won’t have to pay the tariffs. Well, Beau Ties makes it here -- but it has to import fabric from overseas because the silk fabric it needs is simply not produced here. A...
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This week, in episode 267, David C. Barnett, Kate Morgan, and Sarah Segal tackle a challenge every owner who sells services eventually faces: Clients want to hire you, but you want them to understand they’ll mostly be working with your team. How do you make that clear without scaring them off? For some, it’s a delicate balancing act. For Kate, it’s simple: if a client insists on her personal time, she charges, in her words, “a boat...
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This week, in episode 266, David C. Barnett, Jay Goltz, and Kate Morgan wrestle with one of the trickiest challenges for business owners: how to give employees room to grow without losing sight of the company’s mission. David points out that every business is on its way to obsolescence unless it deliberately evolves—and one way to do that, he says, is by letting employees experiment and try new things. That approach, Jay says, is e...
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This week, Ted Wolf, who co-founded Guidewise, which helps businesses manage change, offers a slew of valuable AI suggestions for business owners, regardless of how big or small their businesses are and regardless of whether they’re just getting started or they’ve already taken the leap. Those suggestions range from how much to pay for an AI tool to how to protect your data to how to ease employee resistance to how to figure out wh...
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This week, in episode 264, David C. Barnett and Jennifer Kerhin say they’re already making plans for next year: adjusting pricing, conducting employee reviews, and setting budgets. In the past, Jennifer has chosen to restrain growth to give her employees and her processes a chance to catch up. But this coming year? She says she’s ready to “unleash the hounds.” And for the first time, she’s planning to budget for profit first and th...
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This week, Kurt Wilkin discusses what he’s learned about selling businesses and how he’s thinking about what he might do next. An entrepreneur, an investor, a mentor, and a former business owner who recently sold a recruiting firm, Wilkin tells us why his acquisition of the firm didn't work out the way he hoped and how he managed to turn it around and sell it. Part of the problem, Kurt says, was that he jumped back into the game to...
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September 30, 2025 51 mins
This week, in episode 264, Mel Gravely brings closure to a story he’s been sharing in pieces over the past year. You may recall that he bought a facilities maintenance company a couple years ago that he was convinced he could scale—only to discover that it was hemorrhaging money. Mel dug in, diagnosed the problem, fixed it, bought out his partners, turned the company profitable—and then decided to shut it down. Why close a business...
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September 29, 2025 31 mins
This week, Cameron Madill, an entrepreneur who’s married to an entrepreneur, talks about the challenges of building a business while maintaining a relationship. Along with his own experience, Cameron has done lots of research, including interviewing more than 100 couples, and has also started a business to help couples balance marriage and entrepreneurship. Among other things, we discuss the difference between healthy passion for w...
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September 23, 2025 53 mins
This week, in episode 263, we bring you another 21 Hats Brainstorm. Elan Daniel, who started a small-batch hummus business inspired by a memorable experience in Israel, is trying to figure out his best path to long-term viability. So far, he’s been selling at farmers markets and direct to consumers, making all of the hummus and all of the deliveries himself. Since February, his sales have been growing between 5 and 10 percent a wee...
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This week, Eric Stites, founder and CEO of Franchise Business Review, talks about the state of the franchising world. How much money do you need to buy a franchise? How much can you make? What are the hot categories? What are the most common mistakes? We also talk about life on the other side: What makes a business a good candidate to become a franchisor? And is it possible to avoid the tension -- and litigation -- that so often ar...
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This week, Jaci Russo and Sarah Segal wrestle with a question that haunts many entrepreneurs: How do you bring your kids into the business—whether for a summer or for good—without messing up the business (or the kids)? For years, Jaci and her husband Michael quietly hoped their son Jackson might one day take over their marketing agency. Their unusual strategy? Never mention it to him—at least not until he’d demonstrated interest an...
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This week, Shawn Busse, founder of Kinesis, talks about finding ways to market authentically when so many of the standard tools of marketing are in flux. In Shawn’s case, that means holding an annual event where business owners -- and potential clients -- have the opportunity to come together to learn and interact in person. Of course, throwing such an event costs money. It’s a lot of work. And it’s not always easy to strike the ri...
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A few months ago, John Abrams—author of From Founder to Future—joined us to talk about succession strategies and the different ways business owners can share ownership with employees. For his own business, John chose one of the more radical options: he turned his construction firm into a worker cooperative. Perhaps surprisingly, the more he described the co-op model, the more intrigued Jay Goltz became—although, predictably, Jay di...
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This week, Gene Marks makes a surprising claim: his business is “unsellable.” Never mind that it’s profitable. Never mind that it gave him the freedom to live the life he wanted and that it has left him and his wife financially secure for retirement. According to Gene, the business can’t be sold because it’s too dependent on him and because it has no IP, no exclusivity, and no moat. But is he right? Aren’t those the same challenges...
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