Most contractors don’t realize that the best time to sell is before they feel ready to sell.

In this episode, I sit down with Claudio Vilas, founder of The Roofing Biz Broker, to unpack the uncomfortable truth behind selling a roofing or home service business—and why fewer than 10% of companies are actually sellable, despite constant acquisition outreach.

Claudio works exclusively with roofing companies and sees what happens after the emails, the LOIs, and the headline numbers. What he shares in this conversation challenges many of the assumptions contractors make about value, timing, and private equity.

This is not an episode about hype or “selling out.”

It’s about building a transferable business, protecting your future, and avoiding mistakes that quietly cost owners millions.

1. Why acquisition emails don’t equal real demand
2. The two biggest reasons buyers walk away immediately
3. Why “making good money” doesn’t mean you have a sellable business
4. The critical difference between a profitable business and a transferable one
5. Cash vs accrual accounting—and why buyers care so much
6. What real profitability looks like in roofing
7. Why many owners regret selling, even after a big number on paper
8. The heartbreaking story of an owner who waited too long—and lost everything
9. How private equity roll-ups and the “second bite of the apple” actually work
10. The role of technology and marketing in increasing valuation (and when tools don’t help)

Claudio also explains why selling early can actually reduce risk, how reinvesting a portion of the sale can create generational wealth, and why working with the right advisors matters more than timing the “perfect” exit.

If you’re a contractor doing $2–10M, planning to grow, or simply want to build a business that’s valuable, resilient, and future-proof—this episode will completely change how you think about selling.

🎧 Listen now—and start building your business like an asset, not just a job.