#242 What Every Contractor Needs to Know to Make the Jump to CEO

In this episode of Owned and Operated, John Wilson is joined by Jack Carr from Jackquisitions to break down the four steps every business owner must take to truly become a CEO. From leaving the tools behind to managing senior leaders, John and Jack share the exact progression operators go through—and the pitfalls at each stage.

They dive into the messy middle stages (what Jack calls “owner’s hell”), where infrastructure costs skyrocket and leaders struggle to let go. John opens up about his own journey scaling a $30M home service company and when he finally felt like a real CEO. Together, they unpack:

• Why “founder” and “CEO” aren’t the same thing
• The hardest stage to escape and how to move past it
• Why adding managers can both unlock growth and squeeze cash flow
• What it takes to lead through layers of leadership without losing speed
• The looming leap from single-location to multi-location leadership
  
  
  

This is a must-listen for any contractor or entrepreneur who wants to move beyond being “just the owner” and step fully into the CEO role.

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🎙️ Host
 John Wilson 

🎙️ Guest
 Jack Carr

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John Wilson, CEO of Wilson Companies
Jack Carr, CEO of Rapid HVAC

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