Inside the Deal: What It’s Really Like to Sell Your Tree Company

What if the business you built from the ground up could become your family’s greatest wealth engine?

In this debut episode of The Deal Factory, host Jeff Harkness sits down with Kevin Caldwell, founder of Caldwell Tree Care and now VP of Sales for Tree Guardians, to unpack his journey from startup grit to private equity success.

They dive into the lessons of scaling a business the right way: with compliance, culture, and profitability at the core, and why selling doesn’t mean losing your purpose. From his years as TCIA Chairman to leading in a PE-backed company, Kevin shares candid insights on leadership, family, technology, and redefining success in the trades.

Key Discussion Points:

• From technician to entrepreneur: how Kevin built one of the industry’s most profitable tree care companies

• The turning point that forced a mindset shift toward running a compliant, audit-ready business

• Inside the deal: navigating emotions, due diligence, and choosing the right private equity partner

• Transitioning from owner-operator to VP of Sales, and rediscovering purpose

• The power of servant leadership and communication in scaling culture across 12+ acquisitions

• Technology, AI, and the future of the green industry workforce

• Advice for young tradespeople: why you don’t need a degree to build wealth and purpose