Three Days, 30 Owners, Real Conversations

The fourth annual 21 Hats Live will take place in Cincinnati in May. It’s a rare opportunity to connect with other owners who understand what it takes to build a business.

If you’ve ever wished you could spend more time with people who really get what you’re going through, 21 Hats Live: Cincinnati is the gathering for you. We will have peer-group conversations on the issues you want to discuss. We will tour local businesses. We will eat good food. We will build relationships. And we’ll leave inspired.

As always, I promise there will be no speakers talking at you, assuming they know what your real challenges are. There will be no attendees either—only participants. Everyone who comes helps shape the agenda and the experience. And the group will be limited to just 30 owners.

“Loren, I hope it goes without saying that you know how to put on a spectacular event.” — Sarah Segal

Here’s how it works: Over three days in Cincinnati, participants decide the topics. We start by building a list of the questions and challenges you most want to discuss. We take a vote, and then we work through those topics together in order of interest. Think of it as an in-person peer group with 30 smart, candid owners willing to talk openly about what’s working and what’s not.

Along the way, you can expect:

To meet many of the owners who appear on the 21 Hats Podcast.
To get behind-the-scenes, VIP tours of iconic Cincinnati businesses, including Q&A sessions with their owners. First up: Triversity Construction, led by my co-host, Mel Gravely—one of the city’s most respected owner-operators and a regular on the podcast.
To enjoy good meals, quiet walks, and side conversations that often lead to the most valuable insights of all.
To join a deep-dive brainstorming session, recorded for a podcast, where one owner takes the hot seat to share a real challenge and the rest of the room asks questions and offers suggestions.
To come early or stay late for optional Tuesday and/or Friday group dinners. I can’t share details yet about the extra-special Tuesday evening Mel and I are planning, but I’m confident you’ll agree it’s a home run.

“I’m glad you keep it intentionally small, but everyone who owns a business could certainly benefit. It’s one of those things you want to keep a secret but also shout from the rooftops.” — Lena McGuire

If you’ve ever wondered whether other owners wrestle with doubts, dilemmas, and tough calls, these three days are a reminder that we all confront challenges and suffer setbacks. At previous events, we’ve met first-time founders and 30-year veterans, owners building everything from side hustles with a couple hundred thousand dollars in annual revenue to mature companies with more than $200 million in revenue. The common denominator: an eagerness to show up and engage.

“I wondered if I was especially flawed, with a history of poor decisions offsetting the wins. I just spent four days [at 21 Hats Live: Ann Arbor] absorbing inspiration, wisdom, tips, and techniques—and the encouragement that we’re not unique in our journey. Even if we feel alone.” — David Billstrom

If you’re ready to enter a room where the conversations are honest, the experience is shared, and the collective wisdom is real, here are the details:

When: Wednesday afternoon, May 13, through Friday afternoon, May 15, 2026.
Where: Cincinnati, Ohio (hotel recommendation coming soon).
Fee: $2,750 (all group meals and activities included; travel and hotel not included).
Participants: Limited to 30.
Guarantee: If you’re not fully satisfied, you can get a full refund.

“I don’t know how anyone could leave this event without an insight, an idea, an inspiration, a connection that makes a difference. One conversation could have saved me years of grief.” — Jay Goltz

You can register here for 21 Hats Live.

Hope to see you there!

— Loren