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

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.
ADVICE

Prefer Seller Financing To Reduce Covenants

  • Kris recommends seller financing more of the sale to avoid bank covenants and pressure.
  • He says keeping debt lower would have prevented the worst stress after the transaction.
ADVICE

Open The Books With The ESOP

  • Do roll out open‑book management (the Great Game of Business) alongside the ESOP.
  • Teach employees to read financials so they can act like owners instead of guessing.
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