The 21 Hats Morning Report

The 21 Hats Morning Report

Under New Management

The Small Giants Community has attracted thousands of followers but has yet to prove it can operate sustainably and profitably. A new owner, Jean Moncrieff, is rethinking its approach.

Loren Feldman's avatar
Loren Feldman
May 26, 2026
∙ Paid

Good morning!

Here are today’s highlights:

  • A small bakery shows the impact AI is already having on Main Street.

  • And an on-demand consultant shows the impact AI is having on solopreneurs.

  • President Trump encouraged businesses not to seek tariff refunds. They’re seeking them anyway.

  • It’s being called one of the biggest victories for unionization in a century.

THE 21 HATS PODCAST

In Search of Companies More Interested in Being Great Than Big: Twenty 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 Owners 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?

  • You can subscribe to the 21 Hats Podcast—brought to you by Grasshopper Bank—wherever you get podcasts. This Brainstorm is also brought to you by New Bridge Studios.

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