The Second Bite of the Apple: How Roofers Can Build Long-Term Wealth Through Private Equity
Most roofing company owners know how to make money by running their business well. What many don’t know is how to turn that success into long-term wealth — wealth that can carry them beyond the day-to-day of climbing roofs, managing crews, and chasing leads. That’s where the idea of the “second bite of the apple” comes in.
What Does “Second Bite of the Apple” Mean?
In private equity deals, the platform typically buys 100% of your business. You receive a large upfront cash payout at closing. But here’s the key: you also have the option to roll a portion of those proceeds — usually 20–30% — back into equity in the larger platform.
That rolled equity grows alongside the platform after your sale. When the platform eventually sells again (often 4–7 years down the road), you cash out that equity at the new, often much higher valuation. That’s the second bite.
A Simple Example
Imagine you own a roofing company worth $10 million. A private equity–backed platform acquires 100% of your business, and you receive $10 million at closing.
Instead of pocketing it all, you choose to roll 30% — $3 million — back into the platform.
Over the next several years, that platform scales quickly by acquiring more roofing companies, strengthening operations, and expanding marketing and buying power. By the time it sells again, the platform could be worth $500 million, $1 billion, or more.
Because you rolled a portion of your proceeds, your $3 million stake may now be worth $6 million, $9 million, or even more.
That’s the second bite of the apple.
Why This Matters for Roofers
You lock in security and upside. You take meaningful cash off the table while keeping skin in the game.
You diversify risk. No longer is your wealth tied to weather, labor shortages, or local markets.
You gain leverage. A larger platform brings stronger systems, technology, marketing muscle, and buying power.
You stay in control locally. Most roofing platforms want owners to keep leading their teams, not disappear.
Common Misconceptions
“I’ll lose all control.”
In reality, most owners continue to run day-to-day operations with support and guardrails, not micromanagement.“I only get paid once.”
The second bite exists to keep you motivated and aligned with the platform’s growth.“This only works for the really big players.”
Many roofing companies in the $10–30M revenue range are excellent candidates for this type of structure.
Selling your roofing business doesn’t have to mean walking away. With rollover equity and the second bite of the apple, you can turn today’s success into tomorrow’s wealth — all while continuing to lead your company into its next chapter.
For many roofing contractors, that second bite ends up being sweeter than the first.
Ready to See What Your Business Could Be Worth?
If you’re curious about how a sale and rollover might work for your roofing company, check out our roofing company valuation page to get started.
