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

Your Employees Wants a Career Path. Can You Keep Them?

October 14, 2025 • 45 mins
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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Dashboard: You Probably Should Be Doing More with AI

October 13, 2025 • 43 mins
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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It’s Not Too Early to Be Thinking About 2026

October 7, 2025 • 44 mins
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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Dashboard: A Business Owner Takes a Sabbatical

October 6, 2025 • 26 mins
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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You’re Shutting Down a Profitable Business?

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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Dashboard: Married with a Business

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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The Product Is Great. Is It a Business?

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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Dashboard: How Much Money Can You Make Franchising?

September 22, 2025 • 44 mins
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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In Four Years, This Will Be Your Business to Run

September 16, 2025 • 52 mins
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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Dashboard: Lessons from a Marketer Who Hates Marketing

September 15, 2025 • 26 mins
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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Would a True Capitalist Consider a Worker Co-op?

September 9, 2025 • 45 mins
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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Dashboard: Are You Sure Your Business Can’t Be Sold?

September 8, 2025 • 29 mins
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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Best of: A Punk Rocker’s Guide to Building a Business

September 2, 2025 • 56 mins
In a few weeks, I’ll be in Portland, Oregon, for Shawn Busse’s always terrific Catalyst event. That trip has had me thinking about the city’s keep-it-weird ethos, the spirit that’s made Portland a hotbed for creative business building. My upcoming trip has also inspired me to revisit a podcast conversation Shawn and I recorded in early 2024 with Jenelle Etzel, who is founder of Living Room Realty. The boutique real estate agency ha...
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Best of: Seth Goldman Brews Another Success

August 26, 2025 • 36 mins
It was around Memorial Day in 2022 when Coca Cola stunned the beverage world by announcing it was shutting down production of Honest Tea. No one was more surprised than Seth Goldman, who had co-founded the brand and sold it to Coke. But within two weeks, he’d decided to do it all again, and by that Labor Day, bottles of his new venture, Just Ice Tea, were already landing on store shelves. And now, three years later, Just Ice Tea ha...
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Dashboard: A Business Owner Exits on His Own Terms

August 25, 2025 • 40 mins
This week, Jimmy Kalb tells us how he built his electrical component business and, perhaps even more impressively, how he put a plan in place that has allowed him to walk away from his CEO role at the relatively young age of 63. One key: Jimmy has long been a process guy. For years, he’s been creating processes and handing them over to someone else to manage -- until he left himself with not all that much to do. Another factor: He ...
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It’s a Bear Market for Citibin

August 19, 2025 • 46 mins
This week, in episode 260, Liz Picarazzi tells Jay Goltz and William Vanderbloemen that she’s had a couple of big breakthroughs. For Liz, it’s been a challenging few years dealing with the tariffs while also trying to break into a promising new market. Despite the advice of some very smart people who encouraged her to conquer her first market —urban areas plagued by rats—before expanding into additional markets, Liz has spent sever...
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Dashboard: Can AI Save Small Businesses from Google?

August 18, 2025 • 24 mins
This week, Gene Marks explains why he -- like many other business owners -- long ago gave up on trying to promote his business through Google AdWords and why he’s hopeful that AI will break Google’s monopoly on search. That’s nowhere close to happening, but you can see the changes coming with the arrival of Google Overviews and with businesses trying to figure out what it takes to get discovered on ChatGPT. In the meantime, Gene’s ...
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When Your Biggest Hire Ever Is a Bust

August 12, 2025 • 44 mins
This week, in episode 259, Jaci Russo tells David C. Barnett and Kate Morgan how the hiring of her agency’s first top-level sales person went wrong. About four months ago, when Jaci first told us about this big step, she sounded thrilled. She said her new sales chief was a delight to be around, had hit the ground running, and had already lined up at least one impressive client. Unfortunately, none of that panned out. But Jaci, who ...
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Dashboard: Any Business Can Afford This CFO

August 11, 2025 • 27 mins
This week, Tracy Bech explains how and why she spent six months building, training, and testing her brand new 60 Minute Custom GPT, which is essentially an AI CFO that can perform all kinds of financial analysis on your business. You can interact with it as easily and conversationally as you do with ChatGPT, and it can help you figure out why your margins are off, or how you should expect to perform next quarter, or whether that ne...
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Laura Zander Named Her Exit Price

August 5, 2025 • 49 mins
This week, in Episode 258, Laura Zander tells Mel Gravely and Jennifer Kerhin how she and her husband, Doug, managed to sell their business for precisely the price they wanted. As you may recall, Laura and Doug started Jimmy Beans Wool more than two decades ago as a tiny corner store and turned it into one of the biggest brands in the yarn industry. Years ago, the couple decided they’d be open to selling—but only if the offer was r...
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