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
January 30, 2026 • 42 mins
Ryan Markewich knows the landscaping business from the inside. He built and sold a successful landscaping company in British Columbia, then spent years coaching owners of all kinds of businesses through the Great Game of Business—helping them understand their numbers, their people, and their decisions. Now he’s a certified advisor with an AI-powered platform called LeanScaper It’s only been around for about a year, and it’s designe...
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January 27, 2026 • 46 mins
Things are suddenly moving fast at Sarah Segal’s San Francisco PR firm. Several new clients look likely to sign on, and for the first time in a while, growth feels real. Which leaves Sarah with a familiar, nerve-racking question: Do you hire before the work arrives—or wait until the revenue is actually in the door? If she hires now, she may have to cut her own pay until the new business materializes. And there’s no guarantee it wil...
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January 23, 2026 • 48 mins
Over the past six years, Teamshares has quietly been running an ambitious experiment in small-business ownership. The company has bought some 90 businesses—promising never to sell them—and then converted those companies to employee ownership. Even amid the uncertainty of 2025, those businesses generated more than $400 million in revenue and about $60 million in profit, with a surprisingly low failure rate and unusually high employe...
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January 20, 2026 • 46 mins
Six years ago, Kate Morgan walked away from the sale of her business just days before closing. Since then, she’s endured some rough stretches, fighting through the pandemic and a slump in the software sector where many of her clients live. She’s managed to stay profitable, and she sees lots of opportunity ahead, but the grind has worn her down. After years of pushing, adapting, and holding on, she says she’s had enough. She believe...
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January 16, 2026 • 31 mins
This week, Gene Marks makes the case for optimism. There are all sorts of obvious issues to be concerned about but Gene cites a series of reasons his clients are expecting good things. Chief among them are a series of tax cuts that are coming on line and that are likely to provide more stimulus than many people are expecting. He also expects inflation to moderate and interest rates to fall enough to help out the housing and constru...
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January 13, 2026 • 48 mins
Most business owners say they do. They tell themselves they just need to get through this one crisis, this one launch, this one quarter—and then life will settle down. But what if that’s not actually the goal? This week, Mel Gravely, Lena McGuire, and Ted Wolf talk candidly about what it really takes to build a business—and about whether balance is something owners are truly striving for or simply something they feel they’re suppos...
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January 9, 2026 • 28 mins
This week, Karla Trotman, owner of Electro Soft, a contract manufacturing business outside of Philadelphia, talks about the series of contradictions and tough calls she confronted in 2025. It started with the chaos of the tariffs, which you might think would have helped a domestic manufacturer but which led to suppliers charging more and to customers pulling back and to Karla feeling beaten up by her advisory board, which wanted he...
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January 6, 2026 • 51 mins
For years, business owners have been told to follow a familiar playbook when it comes to hiring: Take your time. Be selective. Hire slow, fire fast. But more and more owners are discovering that those rules don’t fit the reality they’re facing right now. This week, William Vanderbloemen says employers can no longer indulge the luxury of hiring slow. “The shortest sermon I’ve got,” says the former pastor, “is candidates are more fic...
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January 2, 2026 • 36 mins
This week, Adam Russo, co-founder and owner of The Phia Group, explains how his company helps employers reduce their healthcare expenses. The key, he says, is to educate and incentivize employees to be smarter about how they purchase health care—without compromising on the quality of the care. That, he says, is how he’s able to offer employees who’ve been with Phia for five years care that is entirely free: no deductibles, no co-pa...
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December 30, 2025 • 62 mins
This week, we take another look back at the conversations we’ve had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges, including Laura Zander on how she got the price she wanted to sell Jimmy Beans Wool, Liz Picarazzi on her confrontation with a grizzly bear, Jay Goltz on why he just might be a good candidate to turn his business into a worker cooperative, Mel Gravely on why he ...
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December 26, 2025 • 20 mins
This week, Gene Marks tells us it’s late, but it’s not too late to reduce this year’s tax bill. There are still steps you can take, including writing off receivables and inventory and kicking money into a retirement plan. You might even be able to save money on your taxes from previous years if you used the research-and-development tax depreciation. The GOP tax law allows you to go back and retroactively take the full R&D deduc...
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December 23, 2025 • 70 mins
This week—and next week—we take a look back at the conversations we’ve had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges, including Paul Downs on how he diced which employees to lay off, Jennifer Kerhin on asking ChatGPT to review her performance as CEO, Kate Morgan on why she’s been reluctant to raise her prices, Liz Picarazzi on her search for a domestic manufacturer for h...
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December 19, 2025 • 21 mins
As the year comes to a close, I often reach out to John Arensmeyer, who is founder and CEO of Small Business Majority, to get his take on the state of small businesses in America. The picture John paints this year, based on his own observations as well as a recent survey, is not pretty. He points to a host of issues -- health insurance, tariffs, immigration, cuts to federal programs -- every one of which can represent an existentia...
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December 16, 2025 • 44 mins
This week, special guest Rich Jordan takes us inside a marketing challenge presented by his successful acquisition of home services businesses. Do you keep the legacy names of those businesses to preserve local trust—at the cost of running a fragmented, inefficient marketing operation? Do you take the strongest brand you own and roll it out everywhere, even if it may not translate from one community to the next? Or do you wipe the ...
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December 12, 2025 • 22 mins
Most business owners know they should build a forecast for 2026. But many won’t—because it feels intimidating and time-consuming, and let’s be honest, it’s almost guaranteed to be inaccurate. This week, Tracy Bech, founder of The 60 Minute CFO, makes the case for why you should do it anyway. Tracy breaks the process down into three simple steps, shows how even a rough forecast can change the way you run your business, and explains ...
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December 9, 2025 • 50 mins
This week, in Episode 273, David C. Barnett, Paul Downs, and Sarah Segal tackle health insurance, one of the least enjoyable issues business owners confront. It’s renewal season, and the three owners are seeing different systems, different pressures, but similar frustrations. Paul tells us he’s facing the largest premium increases he’s seen since the Affordable Care Act—double-digit hikes that will cost him an extra $15,000 to $25,...
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December 5, 2025 • 33 mins
This week, Brandon Gray, a partner with CRI Simple Numbers, talks about how his firm tracks the performance of what he calls the entrepreneurial economy. As we all know, what’s happening on Wall Street doesn’t always reflect what’s happening on Main Street, which is why Simple Numbers tracks the performance of 100 smaller businesses. Right now, Brandon says, the performance of those businesses isn’t looking great, which doesn’t nec...
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December 2, 2025 • 58 mins
This week, we’re replaying one of my favorite conversations of the year, a Q&A session we recorded in May at our 21 Hats Live event in Ann Arbor, Michigan, with Ari Weinzweig, co-founder of Zingerman’s Community of Businesses. If you’ve already listened to our conversation with Ari, I encourage you to listen again. It’s worth it.
And if you haven’t heard it, well, you’re in for a treat. Much of the discussion focused on a topic ...
And if you haven’t heard it, well, you’re in for a treat. Much of the discussion focused on a topic ...
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November 28, 2025 • 30 mins
This week, Rob Levin, who is co-founder of WorkBetterNow and who has just published a new book, the “New Talent Playbook,” talks about what he considers to be a talent crisis for small businesses. As Rob points out, you might think hiring would be easy these days given all of the recent corporate layoffs—but the people leaving big businesses are probably not the right hires for smaller businesses. Instead, Rob offers a step-by-step...
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November 25, 2025 • 48 mins
This week, in Episode 272, Liz Picarazzi and Jaci Russo compare notes with Ted Wolf on their very different journeys to integrate generative AI into their businesses. For Liz, it’s been frustrating. She resisted AI at first—but while she’s ready to go now, her COO, who also happens to be her husband, still isn’t there. That’s one reason Liz says she feels as though she’s been spinning her wheels. Jaci’s path couldn’t have been more...
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