In this episode of Owned and Operated, John and Jack unpack what leadership looks like inside a $20–40 million home service business—and why that size still feels small. They explore how companies in this range often remain personality-driven, even with impressive revenue, and what it really takes to level up. From forming HR and marketing departments to structuring a true senior leadership team, they dig into the growing pains and leadership gaps most businesses face on the way to maturity.

The conversation dives deep into leadership development, internal promotions, and when to hire key external roles like controllers. John and Jack share why the sophistication of a business doesn’t always match the revenue—and how building the right team early creates long-term stability and growth. If you're scaling past $10 million and thinking about what’s next, this episode lays out a real-world playbook for building a well-rounded, leadership-driven operation.

🔹 In This Episode, We Cover:

What leadership looks like at $20–40M in revenue
Why revenue doesn’t always equal business sophistication
The challenges of building a senior leadership team
Promoting internally vs. hiring externally
When to build HR, marketing, and finance departments
How leadership development programs drive retention and growth
Creating a stable, mature business beyond personality-driven leadership

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👤 Hosted by:

John Wilson

Jack Carr

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

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