Betting on Yourself for a Better Valuation (Why It’s Risky)
Roofing owners are competitive by nature. It’s what drives you to outwork competitors, win over homeowners, and grow your company year after year. So when the idea of selling comes up, it’s common to hear:
“I’m going to hold off. If I double revenue or end the year strong, I’ll get a much better valuation.”
That instinct makes sense. You’ve always bet on yourself. But when it comes to selling your business, that bet can turn into a gamble. Here’s why waiting for “one more big year” rarely works out the way owners hope.
The Market Doesn’t Reward One Hot Season
Buyers don’t value your company based on your best year. They value it based on consistency.
One monster season might make you feel like you’ve turned a corner, but if the three years before that were flat or inconsistent, buyers see it as a spike, not a trend. Multiples are based on durable, repeatable earnings, not one-time lightning-in-a-bottle results.
Timing Can Work Against You
Here’s the hard truth: you can’t control the market.
A strong storm may or may not hit.
Homeowner demand may cool.
Labor or material costs could rise.
What you thought would be your “valuation year” could end up being the year things slow down. And when that happens, you’ve not only lost the big payday you were counting on, you’ve also lost time.
The Owner Burnout Factor
Another risk of waiting is burnout.
Owners who push hard for “a banger year” often do it by taking on even more responsibility themselves. That may bump revenue in the short term, but it raises a red flag for buyers:
“What happens when/if the owner steps back? Will the business hold up?”
Sustainability matters more than raw numbers.
The Better Bet: Play for Two Outcomes
Here’s the piece most owners don’t realize. You don’t need to wait for that “banger year” to maximize value. In fact, by partnering now, you give yourself two shots at winning:
1. The First Bite
You take real chips off the table today, securing financial freedom for the business you’ve built. No more betting it all on next season’s performance.
2. The Second Bite
You roll a portion of your equity and stay in the game. With the backing, resources, and scale of a larger platform, your business can grow faster and stronger than it ever could on its own. That growth creates the “second bite of the apple”, and in many cases, that second payday ends up larger than the first.
This is how real wealth is built in the roofing industry. Not by waiting, hoping, and grinding for one more big year, but by aligning with the right partner and letting your business scale beyond what’s possible on its own.
Betting on yourself has gotten you this far. But when it comes to selling your roofing company, the smarter bet isn’t on one more season, it’s on creating a future that pays you many times over.
If you’re even considering your next chapter, the time to start the conversation is now. I’ve created a simple roofing business valuation page to help you get an idea of what your business may be worth.
