21 Hats Podcast

Welcome to Employee Ownership! (Without the Hype)

14 snips
Nov 11, 2025
Kris Maynard, co-founder of Cathedral Holdings, and Justin Jordan, its CEO, explore the intricacies of employee ownership through ESOPs. They candidly discuss the complexities and potential risks, highlighting that not all employees embrace the model. While ESOPs offer tax benefits, they can turn into risky retirement plans if companies falter. Open-book management has greatly engaged employees, shifting perceptions from retirement benefits to ownership mentality. Kris and Justin also share insights on governance measures to protect employee investments.
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INSIGHT

ESOP As Long‑Term Stewardship

  • Kris Maynard says selling to an ESOP was one of his best decisions for him and employees.
  • He frames it as preserving the business for future generations rather than a simple payout.
ANECDOTE

Post‑Transaction 'Death Valley'

  • After the ESOP close they hit a sales drought and failed bank covenants, which Kris calls "Death Valley."
  • Kris and partners injected cash to remove covenants and restore normal operations.
INSIGHT

Debt Changes Company Behavior

  • Justin notes leveraging a previously debt‑free company fundamentally changed behavior and pressure.
  • He links heavy leverage to micromanagement and short‑term decision shifts.
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