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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

business entrepreneurship

All Episodes

44:13

Dashboard: How Much Money Can You Make Franchising?

21 Hats Podcast ·

2025/09/22

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 arises between franchisees and franchisors? Plus: If you buy a

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52:26

In Four Years, This Will Be Your Business to Run

21 Hats Podcast ·

2025/09/16

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 and not until he’d proven himself somewhere else. The approach seems to

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26:33

Dashboard: Lessons from a Marketer Who Hates Marketing

21 Hats Podcast ·

2025/09/15

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 right balance between education and promotion, but Shawn believes more

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45:18

Would a True Capitalist Consider a Worker Co-op?

21 Hats Podcast ·

2025/09/09

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 did retain a degree of skepticism. So we asked John to come back on the

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29:59

Dashboard: Are You Sure Your Business Can’t Be Sold?

21 Hats Podcast ·

2025/09/08

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 faced, for example, by countless HVAC and plumbing companies that

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56:34

Best of: A Punk Rocker’s Guide to Building a Business

21 Hats Podcast ·

2025/09/02

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 has more than a hundred brokers and a reputation for doing things

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36:15

Best of: Seth Goldman Brews Another Success

21 Hats Podcast ·

2025/08/26

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 has exploded from $1 million in annual revenue to nearly $24 million to

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40:07

Dashboard: A Business Owner Exits on His Own Terms

21 Hats Podcast ·

2025/08/25

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 only hires people right out of school, which is why his successor is

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46:34

It’s a Bear Market for Citibin

21 Hats Podcast ·

2025/08/19

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 several years trying to position Citibin to serve towns, parks, and

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24:58

Dashboard: Can AI Save Small Businesses from Google?

21 Hats Podcast ·

2025/08/18

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 placing his promotional bets on YouTube.

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44:28

When Your Biggest Hire Ever Is a Bust

21 Hats Podcast ·

2025/08/12

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 is hardly the first business owner to have an important placement go

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27:22

Dashboard: Any Business Can Afford This CFO

21 Hats Podcast ·

2025/08/11

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 new service you plan to offer will be profitable. And it’s free.

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49:05

Laura Zander Named Her Exit Price

21 Hats Podcast ·

2025/08/05

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 right. With that goal in mind, they made a deliberate effort to get

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22:08

Dashboard: ‘We’re Not Giving Up’

21 Hats Podcast ·

2025/08/04

This week, Ben Knepler returns to the podcast to explain why he and his co-founder at True Places concluded they had no choice but to suspend production of their portable, outdoor chairs and go into survival mode. Initially, they manufactured the chairs in China, where they’ve been paying tariffs since the first Trump administration. Last year, at considerable expense, they moved production to Cambodia, which at the time was subject to no tariffs. But since April 2nd, the company has been subjected

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44:49

Those Who Can, Do. Those Who Can’t, Uh, Coach?

21 Hats Podcast ·

2025/07/29

This week, in Episode 257, David C. Barnett, Jay Goltz, and Lena McGuire talk about their experiences hiring consultants, advisors, and especially coaches. There are, of course, lots of great business coaches out there, but as the owners explain, it’s easy to be led astray by coaches who don’t really know your industry or who address your specific challenges with their cookie-cutter solutions. And here’s a question: Does it matter whether the coaches were successful in their own entrepreneurial

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25:08

Dashboard: A Few Ideas to Really Help Small Businesses

21 Hats Podcast ·

2025/07/28

This week, Peter Koehler, who helps businesses with their operations, finances, and succession planning, points out that small businesses are not just mini-versions of big businesses. In fact, he says, they’re an entirely different species, and he believes the federal tax code should treat them as such. In our conversation, he suggests a few changes -- tiered payroll tax rates, a startup tax credit to cover professional services, an expanded qualified business income deduction -- that he thinks

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46:10

How Many Clients Did That Post Bring You?

21 Hats Podcast ·

2025/07/22

This week in Episode 256, David C. Barnett, Kate Morgan, and Sarah Segal compare notes on how they market themselves—and their businesses—online. All three are active on LinkedIn, but their strategies, investments, and even their goals are quite different. Are they seeking likes? Credibility? Clients? All three? “Sales and revenue are ultimately the metric we have to look at,” says David. “Likes and shares don't pay any bills.” Plus: Kate just spent what she calls “a boatload of cash” to publish a

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33:43

Dashboard: Are You Risking Everything You’ve Built?

21 Hats Podcast ·

2025/07/21

This week, Sheela Murthy, who founded and built one of the most prominent immigration law firms in the country, talks about the issues business owners may be confronting during the Trump administration’s immigration crackdown. Among the questions Ms. Murthy addresses: What should owners do if they suspect an employee may be undocumented? If the owner decides to keep the employee, what’s the worst that can happen? How reliable is E-Verify? If you employ people who you suspect may be undocumented, are

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46:32

Do I Want to Work with My Family?

21 Hats Podcast ·

2025/07/15

Last September, we hosted a 21 Hats Brainstorm podcast episode in which BaLeigh Waldrop told us that she was considering buying the family business from her parents. BaLeigh, who has been serving as chief financial officer of the Miller Waldrop furniture business that her great grandfather started, recognized that she was being offered a remarkable opportunity, but she had some concerns. Sales have been off of late, the business is predominantly brick-and-mortar, and most importantly, she would have

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38:12

Dashboard: Are We Getting Better at Teaching...

21 Hats Podcast ·

2025/07/14

This week, Frank Rimalovski, who is head of both the NYU Entrepreneurial Institute and the NYU Innovation Venture Fund discusses how his programs help young entrepreneurs build businesses — and why sometimes the most valuable lesson he can offer is to NOT start a business. He also talks about whether you can teach resilience, how he views the strengths and weaknesses of venture capital, and what the growing impact of artificial intelligence will be on programs like his.

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526 results

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