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The Question Every Business Should Ask Itself

It’s worth asking what could go wrong because the goal is to address issues before they become a crisis.

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Introducing A Small-Group Workshop for Owners Who Want to Leave Their Business on Their Own Terms

About 21 Hats: What We Do. What People Say. How We Got Here

Have you read our testimonials? At 21 Hats, don't tell you how to run your business. But we do publish news articles, Q&As, webinars, podcasts about what it takes to build a business.

For the Simple Numbers 100, Profits Are Improving

Revenue is still hard-earned, but entrepreneurs are controlling what they can control.

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Latest PODCAST EPISODE
Best of Episode: Selling My Business Nearly Broke Me
Best of: Selling My Business Nearly Broke Me

This week, we revisit a conversation with Laura Zander that we first published last year, shortly after she and her husband Doug sold Jimmy Beans Wool, the business they had spent more than two decades building. Laura had been preparing to sell for years. She had kept the company’s books clean, built systems that could survive without her, and cultivated relationships with potential buyers. In other words, she had done many of the things owners are told they should do to prepare for an eventual exit. And still, when the right buyer finally came along, Laura says the process nearly broke her.

There were 155 due diligence requests, endless rounds of legal negotiations, mountains of paperwork, and months when Laura and Doug were so consumed by the transaction that the business itself suffered. Meanwhile, life kept happening: a major website migration, tariffs, industry turmoil, family issues, and the constant fear that some unexpected development would cause the buyer to walk away. Even after the papers were signed, the work—and the stress—continued. Laura did ultimately get a deal she was happy with. But the more useful lesson may be what it took just to get there.

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You’re Pre-Qualified for a 13% Loan! (That Really Costs 170%)
TIME TO LISTEN: 50:28

This week, we begin with the story of Paloma Corona, the owner of a thriving preschool in Los Angeles who needed money to expand to a second location. She thought she was borrowing at an annual percentage rate of 13 percent. In reality, the effective APR was 170 percent. She also thought she was taking out a loan. Instead, she was placed in a merchant cash advance—an increasingly common form of financing that can sidestep many of the laws governing traditional loans. The daily payments quickly began draining not only the profits from her business, but also her personal savings. Her business survived, but only because a nonprofit lender stepped in to refinance the debt. Paloma’s story is especially troubling because she wasn’t reckless, uninformed, or running a failing business. She was trying to build a good business. But she was up against a financing industry that has become remarkably skilled at making extraordinarily expensive money look fast, easy, and affordable.

My guests today have all been fighting this problem from different vantage points. Jay Goltz owns a picture framing business and a home furnishings store in Chicago. Ami Kassar helps business owners secure SBA and other responsible financing. And Louis Caditz-Peck, who helped build LendingClub’s small business operation, is now executive director of the Responsible Business Lending Coalition.

In our conversation, we talk about why good businesses get steered into bad financing, how brokers can earn more by recommending the most expensive products, why offers embedded in platforms such as QuickBooks, PayPal, and DoorDash can be especially tempting, and what business owners should do before accepting fast money. We also ask what seems like a remarkably simple question: What could possibly be the argument against requiring every small-business financing company to disclose, clearly and prominently, the true annual percentage rate it is charging? This episode is brought to you by Grasshopper Bank.

I’ll Deal with Succession Next Year
TIME TO LISTEN: 51:38

If you’ve owned a business for any length of time, you’ve probably told yourself some version of this: I'll deal with succession as soon as I solve whatever crisis my business is confronting right now. The problem, of course, is that there's always another crisis to solve or opportunity to pursue, and time has a way of passing.

Jay Goltz has spent decades building a collection of successful businesses in Chicago. He knows he needs a succession plan. He knows that if something happened to him tomorrow, there’d be chaos. And he'd very much like to leave the business in the hands of the employees who helped build it. Over the years, he's considered the usual options—selling to a bigger company, to a few key employees, to an ESOP, even to an Employee Ownership Trust. But every option comes with compromises. And so, year after year, it’s been easier to focus on challenges that seem more urgent—until this past April, when Jay turned 70. "I realized," he says, "I can't kick this down the road much further."

This week, Jay sits down with David C. Barnett and Mel Gravely for an unusually candid conversation about what makes succession planning so difficult—even when you understand how important it is. Jay explains why he has no interest in selling, why money isn't really the issue, and why he still loves going to work every day. Mel, meanwhile, offers some tough love, suggesting that if protecting Jay's family and employees really are his priorities, then something else must be holding him back.

Mel also shares an unexpected twist in his own succession journey. After stepping away from the CEO role two and a half years ago to become executive chairman, Mel found himself pulled back into operations this spring—a reminder that even well-designed succession plans don't always unfold as expected. And along the way, David offers a blunt explanation for why many aging business owners overestimate what their companies are actually worth. The episode is brought to you by Grasshopper Bank.

I Can Help with AI. Do Owners Want Help?
TIME TO LISTEN: 50:40

Alan Pentz is convinced a wave of disruption is about to crash into small businesses—and he’s doing everything he can to warn owners before it hits. He’s writing, teaching, consulting, waving the red flag. He’s just not sure anyone is ready to listen. “I don’t know if you’ve seen 'Don’t Look Up,'” he says, “but it’s kind of like that. The asteroid’s coming—and everyone’s still walking around like it’s normal.” In our latest 21 Hats Brainstorm, Alan put his own future on the table. He asked a panel of owners to help him answer a hard question: Do business owners actually want help adopting AI? And if they do, what kind of help will they pay for? Is there a real, scalable business here—or just a lot of interest and polite nodding? And there’s one more twist: Alan already owns a successful consulting firm. So he also has to decide whether this opportunity is worth jumping back into the startup grind to build another service-heavy business from scratch. The Brainstorm is brought to you by New Bridge Studios, which helps companies, creators, and causes connect their stories to the bottom line.

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Latest CONVERSATION
The Changing Face of the Yarn Industry

For many, knitting may still conjure an image of a grandmother in a rocking chair, her cats sleeping and her doilies taking shape. In recent years, however, the quiet industry of tiny neighborhood yarn shops scattered across the U.S. has become an unlikely cultural battleground. It’s been divided by charges of racism and cultural appropriation that have erupted in a series of social media firestorms, prompting some owners to close, sell, or rebrand their businesses. It may seem surprising that such a quiet pursuit could produce so much conflict, but it’s really not all that different from the fissures afflicting the country as a whole. In this conversation, we meet three women who were not content to stick to their knitting: Adella Colvin, whose business, LolaBean Yarn Co., is a prominent independent dyer based in Grovetown, Ga.; Gaye “GG” Glasspie, a leading yarn industry influencer whose signature color is orange and who is based in Clifton, N.J.; and Felicia Eve, who owns String Thing Studio in Brooklyn, N.Y., one of the few Black-owned yarn shops in the country. The video offers our entire conversation. You can also listen to a slightly edited 21 Hats Podcast version of the conversation wherever you get podcasts.

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What’s in It for the Owner? A Skeptical Conversation about ESOPs

Both Jeff Taylor and Jim Kalb run companies with employee stock ownership plans. Jay Goltz is thinking about implementing one — but he’s got questions, such as: Where does the money to buy the company come from?

What’s Wrong With Small Business Marketing?

It’s not always about marketing. Sometimes, the real issues go deeper. Sometimes, before you can figure out how to sell, you have to figure out who you are.

The Changing Face of the Yarn Industry
TIME TO WATCH: 1:34:43

For many, knitting may still conjure an image of a grandmother in a rocking chair, her cats sleeping and her doilies taking shape. In recent years, however, the quiet industry of tiny neighborhood yarn shops scattered across the U.S. has become an unlikely cultural battleground. It’s been divided by charges of racism and cultural appropriation that have erupted in a series of social media firestorms, prompting some owners to close, sell, or rebrand their businesses. It may seem surprising that such a quiet pursuit could produce so much conflict, but it’s really not all that different from the fissures afflicting the country as a whole. In this conversation, we meet three women who were not content to stick to their knitting: Adella Colvin, whose business, LolaBean Yarn Co., is a prominent independent dyer based in Grovetown, Ga.; Gaye “GG” Glasspie, a leading yarn industry influencer whose signature color is orange and who is based in Clifton, N.J.; and Felicia Eve, who owns String Thing Studio in Brooklyn, N.Y., one of the few Black-owned yarn shops in the country. The video offers our entire conversation. You can also listen to a slightly edited 21 Hats Podcast version of the conversation wherever you get podcasts.

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