The build
I started Legacy Roofing out of my garage in 2012. By 2019, we were one of the Top 100 largest roofing contractors in the country: 130-plus employees, three locations in Ohio and one in Florida. I owned 100 percent of the business, and it was debt-free. Then private equity started calling. Real interest, serious numbers. If I was going to sell, I had one shot to get it right. I couldn't afford to make a mistake.
So I did what most owners do: I brought the offer to my CPA, just to talk it through.
That's when the language started. EBITDA. Net working capital. Reps and warranties. Indemnity escrows. Term after term that had nothing to do with actually owning and running a great business — and I was the only person in the room who didn't speak it. Everyone else at the table had done this before. I hadn't.
What I got right, and what I wish I'd had help with
Here's the part I want other owners to hear clearly: I didn't get it all wrong. Some of it, I figured out and nailed on my own. And I wasn't flying blind — with my attorney and my CPA, I negotiated and structured terms I'm still proud of.
But here's what I've come to believe cost me the most. It wasn't necessarily any single aspect of the deal or its terms. It was that I never truly prepared the company to be sold, and I never drove a competitive process. I negotiated hard with the buyer in front of me. What I didn't do was make buyers compete for me. Knowing what I know now, that alone would have been the game changer.
I sold Legacy Roofing in July of 2019. It was a good outcome. But I've spent every year since asking myself what it would have looked like with someone in my corner who'd actually sat in my chair before — someone who knew how to position my business to buyers and maximize its value, not just help me get to closing.
The gap I didn't expect
After I sold, the calls didn't stop. They just changed. Private equity firms started reaching out — not to buy anything this time, but to pay me to teach them how to evaluate and buy companies like the one I'd just sold. I got a full education in how PE actually thinks about a deal, from the other side of the table.
Then other construction and home services owners started calling too. Guys hitting the exact same walls I'd hit. Same confusion. Same jargon. Same feeling of sitting in a room where everyone else already knew the rules. I started helping a few of them through their own deals. Then a few more. The demand continued, and this eventually evolved into Options2Exit.
The framework
If you're a founder-led home services or construction business thinking about an exit — this year, in three years, or you're just not sure yet — here's what I'd tell you, operator to operator:
Drive a competitive process. A single offer isn't a negotiation. It's a formality. When you bring multiple qualified buyers to the table, you don't just see one number — you see different prices, different terms, and different buyers with different plans and strategies for your business. That's where the leverage lives. You don't find out what your company is actually worth until more than one buyer is fighting to own it.
Know who's actually on your side of the table. Your CPA and your attorney are critical to getting a deal done, and mine were. But an M&A advisor working for you plays a different role: identifying the best buyers and making sure they bring the best offers to the table for your CPA and attorney to execute on. It's a different skill set, it's a strategic process, and adding that person to your team will add real value.
Find someone who understands you, not just the transaction. The right advisor becomes your advocate. They know your business and your industry. They identify the strengths and market differentiators of your business and express them to buyers in a way that builds real interest. They've sat in your chair, made payroll through a slow season, and had the hard conversation of telling a key employee the company is selling. That's not something you learn from a finance book.
Why I built Options2Exit the way I did
Today, our team advises on more than $100M in transactions a year, pacing toward $200M — all sell-side, all in home services, business services, and construction. We're operators, not bankers. Our job is to help you net 30%+ more than you would going it alone — same company, same market, same financials, just better preparation and a real process behind you.
$0 until close. No retainer. No discovery fee. No upfront cost of any kind. If we don't get the results you want, you pay nothing. That's not a marketing line. It's the whole structure of how we get paid — and it's the guardrail I wish I'd had in that room with my CPA in 2019.
If you're thinking about it
You don't have to be ready to sell to start this conversation. Whether it's next year or five years from now, the earlier you understand the language, the players, and what a real process looks like, the better your outcome will be when the time comes.
I learned all of this the hard way, at the table, with an offer already in my hand. You don't have to.
Let's start a conversation.
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