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What if the thing that looks like a once-in-a-lifetime opportunity… is actually a trap?

When starting Jackson Hewitt, John thought he struck gold: a deal that would double his company’s footprint overnight. Instead, he inherited unpaid employees, sabotage from the inside, and a cashflow disaster so brutal it nearly took the company down.

But here’s the thing, he didn’t quit.

He didn’t even flinch.

He had to shrink to survive, learn the hard lesson, and come back stronger.

This conversation is about:

  • Learning when to pivot without abandoning the mission
  • Why you should never scale without testing small
  • How to lead through chaos without losing your soul
  • And why being too early can be just as dangerous as being wrong

If you’re building something right now, especially if it feels fragile, uncertain, or like it might break, you need to hear this.

Hold the vision. Loosen your grip.

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10 episodes