The Costanza Principle and how to sell at your highest multiple

By Exit Stage Left Advisors.

The best time to sell your roofing company is when revenue and profits are rising year over year.

Between politics, tax law uncertainty and AI disrupting everything from estimating to marketing, there’s a lot happening right now. So much so that roofers everywhere are asking themselves, “When is the right time to sell my business?”

Before we get to the George Costanza Principle and how it can impact your bank account, let’s quickly walk through the meaningful changes we just saw in 2025 and how they factor into timing.

Under the current administration, the One Big Beautiful Bill Act, OBBBA, made sweeping tax changes, including restoring 100% bonus depreciation, making the QBI deduction permanent, raising the estate tax exemption to $15 million in 2026 and adjusting QSBS rules. Those are huge changes.

But as we know, what’s passed today can absolutely be revised with the next administration.

If capital gains rates were to rise anywhere near the previously proposed 40%, or estate exemptions reverted to previous levels, the difference could be millions of dollars in net proceeds. Real money, even generational money.

But the real question to ask yourself isn’t “what’s going to change,” it’s “how can I command the biggest multiple for my business?”

Enter Art Vandelay, importer exporter, aka George Costanza.

In one episode of Seinfeld, George decides to leave every interaction “on a high note.” And funny as that is, it’s great advice for exit timing.

The best time to sell your roofing company is when revenue and profits are rising year over year, and you can credibly show that trend is going to continue. Selling when your pipeline is full, your sales team is crushing and your operations are dialed in makes buyers compete. And competition drives multiples.

That’s the George Costanza Principle, always leave on a high note. Because selling when your business is thriving changes the multiple game.

If you want to know more about how to position your roofing business to command the highest multiple, you can reach us directly at alex@esladvisors.com or ben@esladvisors.com. You can also visit www.wesellroofers.com for a free business valuation.