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
More Ways To Connect with O&O
John Wilson, CEO of Wilson Companies
Jack Carr, CEO of Rapid HVAC
📌 Disclaimer: Some links may include UTM parameters or affiliate relationships, meaning we may earn a commission if you make a purchase. Episodes may feature sponsors, but all opinions expressed are our own.
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