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Four Degrees of Communication

Something different happened two weeks ago when about 60 of us gathered at a remote location with spotty Wi-Fi, very little structure, and plenty of unhurried time together.

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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.

The Simple Numbers 100 Shows a Divided Economy

The model, which tracks a diverse set of entrepreneurial businesses, indicates companies with less than $10 million in revenue are growing at less than 1 percent a year.

What Was I Thinking When I Signed the Lease?

Right in the middle of Covid, I took the space for five years. It’s worked out—but not in the way I expected.

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Latest PODCAST EPISODE
Episode 296: ‘I’m Skeptical AI Is Going to Help Us’
‘I’m Skeptical AI Is Going to Help Us’

This week we explore some contrasting opinions about artificial intelligence. Paul Downs has serious doubts that AI will ever have a significant impact on his business. Paul, who builds custom conference tables, says his business depends on something AI still lacks: real world experience. While AI can generate impressive images and concepts, he argues that it has no understanding of manufacturing constraints, material properties, production processes, or the capabilities of the people and machines that have to bring an idea to life. “An image of a thing that looks cool is not a design,” Paul says. “A design is a set of information that's informed by intelligence and experience.”

Ted Wolf, who helps companies implement AI, agrees that AI can't replace the collective creativity and judgment of skilled people. But he believes Paul may be looking at the problem too broadly. Instead of asking whether AI can design and build custom furniture, Ted suggests breaking the workflow into smaller pieces and experimenting with targeted applications. “You know your business better than anybody else,” Ted tells Paul. “But don't look at the big picture and think that's the entire thing. There are many small pieces that people can start doing today.”

The result is a thoughtful debate about one of the biggest questions facing small business owners: Is AI going to change everything, or are there businesses where human expertise will remain irreplaceable?

Plus: Channon Kennedy shares what she learned from participating in a Goldman Sachs program for Black women entrepreneurs. And the owners discuss what debt can—and cannot—do for a business: “Funding does not fix a broken business model. It makes it die faster.”

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In Search of Companies More Interested in Being Great Than Big
TIME TO LISTEN: 50:15

20 years ago, Bo Burlingham gave a name to a feeling a lot of business owners had struggled to articulate. In his book Small Giants, Bo profiled companies that had chosen not to chase growth at all costs. Most were bootstrapped, owner-operated businesses that cared less about getting big than about building something enduring, meaningful, and excellent. They weren’t anti-growth. They just wanted growth to be intentional. And for many owners who read the book, the reaction was immediate: “I thought I was the only one who felt this way.” Out of that recognition grew a community—and eventually an organization—led in large part by Paul Spiegelman, whose own company embodied the Small Giants philosophy. With Bo’s encouragement, Paul launched the Small Giants organization 15 years ago to connect owners trying to build great companies without sacrificing culture, independence, or quality of life.

At our recent 21 Hats Live gathering in Cincinnati, we explored where that movement goes next in a Brainstorm session with Jean Moncrieff, who took over leadership of the Small Giants organization last year. Jean—who’s from South Africa, lives in Zurich, but is moving to the U.S.—brings both momentum and candor to the role. He recently led his first Small Giants Summit in Detroit, which attendees—including me—praised for its renewed energy and sense of purpose. He’s also the author of a terrific new book, Finding Freedom: The Business Owner’s Guide to Building a Valuable Company and a Meaningful Life. But as you’ll hear, Jean recognizes there are challenges ahead.

What exactly is Small Giants today? Who is it for? What makes it different from the many other organizations competing for the attention of business owners? Does it need a more formal set of principles—or even an operating system—to help companies put its philosophy into practice? Can it stay true to its founding mission while also attracting businesses large enough to support its events and programs? Ultimately, the conversation arrives at a tension at the heart of the enterprise: Can the Small Giants organization itself become a sustainable, profitable business without losing the values it was created to protect? In other words, can Small Giants become a true small giant?

When Employee Violence Walks Through Your Door

Michelle Wyatt has replayed the events in her mind countless times, looking for warning signs she might have missed. But even now, she can’t find any. Both employees had passed background checks and drug tests. Both were considered trusted, valued members of the team. And yet, within a span of months, two violent incidents involving employees left Michelle and her company reeling. In this week’s conversation, Michelle joins Jay Goltz, who has dealt with employee violence in his own business, and special guest Sandy Kapell, who’s made a career leading human resources, to wrestle with a question that haunts a lot of business owners: How much responsibility can you reasonably bear for the actions of your employees?

The discussion goes beyond hiring practices and background checks. Michelle talks candidly about the grief her team experienced, the guilt of wondering whether she should have seen something sooner, the relief that the violence didn’t occur aboard her riverboat cruise ship, and the unsettling realization that no amount of experience truly prepares you for something like this. “Please stop torturing yourself,” Jay tells Michelle. “From what you've said, there's just nothing you could have done about this. It's part of business, unfortunately.”

Managing People Is Hard: When Does Demanding Become Toxic?
TIME TO LISTEN: 49:54

It’s easy to condemn the horror stories coming out of Noma, the celebrated restaurant in Copenhagen. But this week, Jay Goltz, Jennifer Kerhin, and Ted Wolf confront a harder question: How far are the rest of us—business owners in every industry—from crossing the line? Because it’s not just restaurants. Most owners don’t set out to be abusive. They set out to build something great. And somewhere along the way, high standards can start to blur into something else. ‘I was out of control when I was in my 20s,’ Jay admits.

So, what changed? And where did the owners land? How much command and control is actually necessary? When does pushing someone cross the line—and when does not pushing them enough become its own failure? Have you ever held onto the wrong employee too long? Or pushed the right one too hard? Jay doesn’t sugarcoat his opinion about yellers: “You’re going to tell me you’re passionate. I’m going to tell you, ‘You’re an asshole.’”

The group digs into the trade-offs every owner faces: hiring versus managing, systems versus stars, culture versus performance. What do you do with the high performer who damages the team? Can you really coach anyone to excellence—or are there limits? And then there’s the quiet warning sign many owners ignore: Something goes wrong, and someone says, “Oh, well, everybody knows how Bob is.” That, says Jay, is when you know you’ve got a problem. This is a conversation about judgment calls—messy, human, unavoidable. Because as Jennifer puts it, “It’s really hard to manage people.”

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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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