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The Holiday Test: How to Build a Business That Runs Itself (A 30-Year Masterclass with Stephen McHenry)

Nov 5, 20251 min read
The Holiday Test: How to Build a Business That Runs Itself (A 30-Year Masterclass with Stephen McHenry)

Could your business keep growing if you took a month off? Or would everything grind to a halt without you?

In this episode, we unpack The Holiday Test, the ultimate measure of business freedom, with Stephen McHenry, founder of McHenry Partners. Drawing on three decades of experience helping small and medium-sized businesses thrive, Stephen shares a clear roadmap for building a business that works for you, not the other way around.

You’ll learn:

  • The three stages of business growth: from self-employed to operator to investor.
  • How to design a business that passes the Holiday Test, thriving even when you’re away.
  • Lessons from Jim Collins’ Good to Great, including how to find your “Hedgehog Concept.”
  • Why quarterly planning and accountability are the keys to consistent execution.
  • Five practical levers to grow gross profit without just cutting costs.

If you’ve ever dreamed of stepping back without everything falling apart, this conversation will show you how to make it happen, one deliberate step at a time.

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