If you like the 21 Hats Podcast, you’re going to love the 21 Hats Live events. Think of them as three-day peer group conversations where we share wins and challenges, tour local businesses, eat good food, make friends and connections, and leave inspired. Our third annual event will take place in Ann Arbor, Michigan, running from Wednesday, May 14, to Friday, May 16. On Wednesday the 14th, we’ll gather on a private patio at Zingerman’s Roadhouse, where we will introduce ourselves and our businesses and our challenges. Then we’ll eat.
On Thursday, we’ll vote on the topics we’re most eager to discuss—most likely questions like, “Would you take outside capital?” “What are you doing with AI?” “Is your business as profitable as it should be?”—and then we’ll discuss those topics. We’ll also take a tour of Motawi Tileworks. We’ll pick a business for a deep-dive brainstorming session. And we’ll eat at the renowned Zingerman’s Delicatessen that is the original Small Giant.
On Friday, we’ll record a Q&A session with Zingerman’s co-founder Ari Weinzweig to be published later as a podcast. We’ll conclude our peer-group conversation. And we’ll finish with lunch. For those who are able to arrive early and/or stay later, there will also be small-group dinners Tuesday and Friday evenings. And here’s my ironclad guarantee: If the gathering doesn’t feel like a family reunion after about 30 seconds—or if you’re not fully satisfied for any reason—you get your money back.



