
There are a lot of companies out there who make a living giving awards to other businesses. The awards can be fun and can help spread the word about what you’re doing. But we should all think about what we really think is worth celebrating.
This is an unusual opportunity to participate in a collaborative workshop with fellow business owners led by someone with real expertise. Leave with a real strategic plan tailored specifically to their own business.
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.
One of my clients has a tough decision to make: Is he willing to use his home as collateral?

This week, Paul Downs tells Kate Morgan and Liz PIcarazzi that he recently posted a job on Indeed and got 153 resumes—more than he’s ever gotten before, which prompted some interesting questions: What does this mean for business owners? Should a job posting be more about what the company expects from a candidate or more about what the company has to offer? Do the owners ask candidates to take personality tests? If the owners get 150 resumes, do they ask ChatGPT to review them? And doesn’t it seem as if more people are looking to switch careers? “When I look at someone who's working as a graphic designer in an ad agency,” Paul tells us, “I'm thinking: This person realizes AI is coming for their job.” Plus: Liz gives us a surprisingly upbeat update on her tariff situation. And the owners respond to a Reddit post asking whether it would be crazy to start a business in the current economic environment. Paul’s response: “Don’t do it.”
This week, we bring you a conversation recorded at our recent 21 Hats Live event in Ann Arbor, Michigan, with Ari Weinzweig, co-founder of one of America’s most influential small businesses. Starting 43 years ago with a highly successful college-town delicatessen that they could have replicated all over the country (including for Disney), Ari and co-founder Paul Saginaw have instead built Zingerman’s Community of Businesses, a collection of 12 Ann Arbor-based, collaboratively run businesses each with its own leadership and ownership structure. Together, these businesses produce $80 million a year in revenue. They include a bakery; a coffee company; two event spaces; a roadhouse; a Korean restaurant; a mail-order operation; an international food-tour business; a publishing house that publishes, among others, Ari Weinzweig; and a training center—ZingTrain—that has shared the Zingerman’s approach to business building with more than 10,000 other businesses.
In 2003, Bo Burlingham pronounced Zingerman’s “The Coolest Small Company in America.” Bo’s article became the foundation of Small Giants, his book about companies that are more intent on being great than being big. The last thing we did at 21 Hats Live was to sit down with Ari to talk about that philosophy. In his passionate responses to our many questions—reponses, I should note, that include a few F-bombs—Ari explains how the Zingerman’s team decides whether to start a new business, how he and Paul made (and re-made) an especially difficult decision about expanding, how he and Paul have managed to sustain their partnership for more than four decades, how they chose a succession plan, how they know if they’re charging enough, why for many years Ari’s mother continued to believe he was a failure, and a whole lot more.
This week, Jennifer Kerhin, Jaci Russo, and Sarah Segal talk about how they’ve been using ChatGPT. Jennifer has deputized the AI chatbot as a key advisor, feeding it all kinds of performance data and soliciting its analysis before making hiring, financial, and strategic decisions. Recently, she asked it to identify her biggest blind spots as a CEO. Five seconds later, it spat out five answers with detailed explanations and suggestions. And what did Jennifer think of the feedback? “It was right on,” she tells us. “I mean, it was totally, absolutely true.” We even brought ChatGPT into our conversation in real time, asking it whether Jaci had hired the right business development person, whether Sarah had been fully prepared two years ago to buy back her PR firm, and what’s the best podcast for small business owners. Plus: while we were talking, Jaci asked ChatGPT to evaluate the performance of her co-founder and spouse, MIchael. Let’s just say, it does have some concerns.
This week, Paul Downs tells Lena McGuire that, because his business has not picked up, he has had to lay off two employees. Paul explains how he chose which employees to let go, including to what extent he considered who has just had a kid and who just put a down payment on a house. We also talk about whether Paul should start experimenting with different ways to attract business or whether he should continue to do what’s worked in the past and try to ride it out. And then there’s this: Paul has managed to do what so many owners strive to do, which is to take himself out of the day-to-day operation of his business. But what does that mean when there’s very little business coming in? How should he be spending his time now? Plus: Lena and Paul respond to a small business subreddit post from a business owner who quit a comfortable job to pursue the idea he just couldn’t get out of his head. Now, he vacillates between thinking his business is going to be huge and thinking he’s made the dumbest mistake of his life, and he wants to know if anyone else has experienced that kind of doubt. I think we know the answer to that one.
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.
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.
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.
This week, we talk to two people who walked away from promising careers to buy blue collar businesses. Long before search funds and sweaty startups became all the rage, Bob Schwartz left a Wall Street investment banking career to buy a chain of laundromats, SuperSuds, which operates in Delaware, Maryland, Pennsylvania, and Virginia. More recently, Mills Snell left a prominent private equity firm to buy a roofing contractor, Aqua Seal Manufacturing and Roofing, which is based in Columbia, South Carolina. In this conversation, Schwartz and Snell talk about what they were thinking, what they learned about buying a business, what they’ve learned about operating a business, and whether they’re looking for an exit.