Ep. 450 — Jean Moncrieff: Letting Go, Leading with Values, and Building a Company That Lasts

7 min read

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Episode Summary

You built the business by being at the center of every decision, and the same instinct that got you to where you are now is the lid keeping you from going further. You hear “people first” and your brain translates it to “fluffy.” But the math doesn’t lie: Beryl Health sold for a 22x multiple because Paul Spiegelman put a circle of growth around his people for years. Consuela broke through a $3M ceiling and hit $46M when Connie took the armor off and brought in a COO. Smiley Technologies went from stuck at $5M to $20M when Elizabeth stepped in and led with people first. Jean Moncrieff just took the torch from Paul as the new leader of the Small Giants Community, and I wanted to get him on to talk about what he’s seen across 15 years inside that room. We got into why most owners chase growth as a way to avoid the thing they actually want (independence), why the highest-multiple businesses tend to be the ones that put people before the spreadsheet, and why letting go of control is the single hardest move in the owner-operator arc. Real stories from Tom Walter, Eric Rieger, Matt Hoying at Choice One, and Zingerman’s. Plus where Jean is taking Small Giants next.

Top 10 Takeaways

  1. The thing that built your business (your need for control) is the exact thing keeping it from growing past you.
  2. Growth chased as revenue and headcount is the riskiest path to the independence you actually want.
  3. People-first isn’t fluffy. It’s the most reliable cash flow strategy you’ll ever run.
  4. Run every big decision through a filter of your core purpose and values, then deal with the legal stuff.
  5. Your business is shaped by your community as much as you give back to it. Pull it out and you leave a void.
  6. Above operating cash flow is the operator’s job. Below it is every ownership decision you’ve been avoiding.
  7. Employee ownership works because the underlying business actually has to be good enough to transact internally.
  8. You don’t hire a great salesperson who’s misaligned with your values. You bleed for 18 months pretending it’ll work.
  9. For every four boomers retiring, there’s one emerging leader. The talent war is already here.
  10. You never lose your purpose as an owner. You lose your why when you sell without one.

Sound Bites

“100% of the companies on the planet that I’ve ever met are underpriced… I think fundamentally it’s putting people before everything else.” (@TBD) — Jean Moncrieff

“If you’re the most greedy SOB, you should be a conscious capitalism small giant. It works.” (@TBD) — Ryan Tansom

“We sold more shit at lower margins… I did things to avoid a set of circumstances, and the shit I was doing would get me what I didn’t want.” (@TBD) — Ryan Tansom

“When I just started to focus on the values and the culture in the business, all the outputs came. The revenue came, the profit came.” (@TBD) — Jean Moncrieff (relaying Tom Walter)

“Every single time, it’s the owner. It’s the business owner who’s got to change. When they let go, things prosper.” (@TBD) — Jean Moncrieff

About This Episode

Jean Moncrieff is the new leader of the Small Giants Community, taking the torch from founder Paul Spiegelman. A former business owner who exited his own company, Jean has spent the last decade coaching owners through tools like Metronomics to build leadership teams, find traction, and create real options for stepping back. He’s been part of the Small Giants Community since 2011, going back to the first conference, where he met Jack Stack at the bar. His core purpose is helping entrepreneurs find freedom. In this conversation, he and Ryan get into what makes the Small Giants ethos distinct, why people-first companies tend to produce the highest multiples, and where Jean is taking the community next.

Resources Mentioned

  • Small Giants Community — The community Jean now leads. — smallgiants.org
  • Small Giants by Bo Burlingham — The book that started it all. First chapter available on the Small Giants website.
  • Small Giants Leadership Academy — Flagship program for emerging leaders, kicks off in January each year with cohorts of two-to-three leaders per company.
  • Small Giants Circles — Ongoing program for Leadership Academy graduates.
  • Passport Events — Behind-the-scenes visits inside Small Giants businesses, returning in Chicago with Cherry’s Industrial.
  • Mentoring Sounding Board Program — Pairs young leaders and owners with seasoned Small Giants mentors.
  • 2026 Small Giants Summit — Detroit, June 2026.
  • Beryl Health / Paul Spiegelman — Sold at a 22x multiple after years of people-first reinvestment (“circle of growth”).
  • Zingerman’s Community of Businesses — Ann Arbor-only family of businesses model instead of franchising.
  • Tasty Catering / Tom Walter — Featured throughout; Entangled by Tom Walter referenced.
  • Choice One Engineering / Matt Hoying — Filter-based decision-making and hybrid employee ownership model.
  • Textamall — Moved from ESOP to EOT, headed toward 100% employee-owned.
  • Atomic Object / Carl Erickson — DIY-sop model with 80 of ~120 employees owning the LLC.
  • Consuela / Connie Cook — From $3M to $46M after taking the armor off and bringing in a COO.
  • Smiley Technologies / Elizabeth Glasbrenner — From stuck at $5M to $20M after leading with people first.
  • Great Game of Business / Jack Stack — Open book management.
  • Metronomics / Shannon Susko — Operating system Jean used in coaching.
  • Naval Ravikant on Modern Wisdom (Chris Williamson) — Win the game so you don’t have to play the game.
  • Purpose Summit / Daven Sarvango — Referenced as part of the broader ecosystem.

Connections

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