The day I sold my first company, I didn’t pop champagne.
I signed the documents, took the congratulatory calls, and went home to make dinner for four kids. Sometime after putting the kids to bed, I took a peak at my checking account. It had a lot more zero’s than the night before. Other than that, I truly had no idea what I had just done.
Not the transaction. I understood the transaction. I mean everything around it. What the sale would actually pay once the fine print did its work. What my life would look like inside the acquirer’s walls. Who I was going to be on Monday morning.
Ashton Partners was my first company. An investor relations firm I co-founded and built into a multi-million-dollar business while raising four kids, back when nobody used the word mompreneur and the few women in my industry kept their family photos in a drawer. I had a great business partner in that firm who has gone on to have individual success on his own. It wasn’t Victoria. She was on my team at Ashton then, still a few years away from becoming my co-founder at Clermont. When my partner and I sold Ashton to a much larger consulting firm, the multiple was roughly 1x revenue.
At the time, that felt like a win. A serious acquirer wanted what I had built. The deal closed. Everyone shook hands.
It took me years, and a second exit at 5x revenue, to understand that my first sale wasn’t a win. It was a tuition payment. That tuition bought three lessons nobody offered me beforehand. I’m offering them to you now.
Why we only got 1x
Ashton was a good business. Real clients, real revenue, a real reputation, even recurring revenue. But I never built it to be sold. I built it to run.
And recurring revenue alone doesn’t get you a premium. It gets you a look. What we didn’t have was a reason to pick us over the firm down the street. Our model looked like everyone else’s. No growth engine a buyer could point to and say, this is what it becomes under our ownership. No niche we owned so completely that a competitor couldn’t muscle in.
So the buyer paid for exactly what existed on the day of the sale. Not a penny for what it could become. That is what 1x revenue means. It means you sold the past.
And that’s the part nobody says out loud. Buyers don’t pay for your late nights, your near-death pivots, or the payroll you covered while praying a client check would clear. They pay for the future. If you haven’t built a future they can see and believe, they won’t price one in. They’ll price the past, and the past always sells at a discount.
Lesson one: you’re probably getting the timing wrong
First-time sellers get timing wrong in one of two directions.
Some wait too long. They run the business until they’re exhausted, growth flattens, and a buyer can smell the fatigue in the numbers. Then they sell from weakness. Nothing scares off a buyer, or shrinks an offer, like a growth chart that flatlines right when they start looking at it.
Others sell too early, before the business has the story that commands a premium. That was me. When a credible buyer showed up, I treated the offer as the timeline. Wrong. The offer is not the timeline. The story is the timeline. If the story isn’t finished, neither is your valuation.
At my second company, Clermont Partners, we launched an ESG communications practice years before we thought seriously about selling. We were early. Honestly, about eighteen months too early. Our target buyers were still googling what ESG stood for. But by the time we went to market, that practice was a high-margin growth engine with regulatory tailwinds and almost no competitors. Buyers weren’t paying for what Clermont was. They were paying for what it would become under their ownership. That’s the entire difference between 1x and 5x.
The concrete lesson: your exit gets priced three to five years before it happens. If there’s any chance you’ll sell within a decade, the decisions you make this quarter are already setting the multiple. Recurring contracts. A niche you can defend. Margins that prove the business is built to last. A team that runs without you in the room. Start building those now, not when the banker calls.
Lesson two: the structure is the deal, not the number
Nobody told me this before my first sale, so I’ll say it plainly: the headline number is marketing. The payment schedule is the deal.
My first sale came with an earn-out. A meaningful chunk of the price depended on how the business performed after close, under an owner whose decisions I no longer controlled. I signed it without fully understanding what I had agreed to carry. The buyer had transferred their risk to me, and I had said thank you.
We hit the earn-out. In the first year. And I want to be honest about what that was: luck. SRS Acquiom’s deal research shows earn-outs pay out about 21 cents on the dollar, with disputes in at least 28% of cases. Roughly one in five private deals includes one. Most sellers who sign an earn-out never collect most of that money. We were the exception, and I didn’t know it at the time. I thought hitting it meant the structure was fine. It meant the dice came up right.
The second sale had no earn-out. That was not an accident. Our first acquisition offer for Clermont came in with too much of the payout deferred and contingent, and this time we knew exactly what we were looking at. With 24 hours left before the offer expired, we made two calls. I phoned my private equity contact. Victoria sat down with her attorney. Both said the same thing, independently: too much risk in the final payment structure, hold out for better. So we did. We walked away from the deal on the table, rebuilt the story, and ultimately got 35% more. Paid on day one. No earn-out. Nothing contingent on anyone else’s ownership of my work.
The concrete lesson: long before a sale is on the horizon, put someone in your corner who can read a term sheet without flinching. Not your banker, who gets paid when the deal closes whether or not it’s the right deal. Someone with no financial stake in whether you sign. Then scrutinize three things in every offer: the number and what it’s actually based on, how much of the payout is at risk after close, and whether you can walk away if you need to. If the answer to the second question is an earn-out, price it like the data says, not like the term sheet says.
Lesson three: nobody tells you who you’ll be on Monday
This is the one that blindsided me.
I had spent years being the founder. The one who commanded the room, made the final calls, signed the fronts of the checks. Then the deal closed, and I went to work inside the acquirer as one of its few female senior executives.
The culture was kill or be killed. Nearly all of senior leadership was male. Nobody talked about their kids. In all my time there, I remember seeing photos of children in exactly one office: the CEO’s.
I had sold my company. What I hadn’t planned for was how much of myself was bundled into the deal. My calendar, my decisions, my standards for how people get treated, all of it now lived inside someone else’s culture. It took a toxic stretch of years and a garden leave clause to get it back. The business I started next, with Victoria, exists because of what that period taught us both about what we would never sell again.
The concrete lesson: decide before you sign what you’re selling and what you’re keeping. The name, the client list, the P&L are for sale. The way you operate is not. During diligence, ask hard questions about the acquirer’s culture. They’re certainly asking hard questions about yours. And have a real answer to what you’ll do the day after close, because “I’ll figure it out” is not a plan. If the answer is a multi-year employment agreement inside the buyer, understand exactly what you’re agreeing to live inside before you initial that page.
The gap between 1x and 5x
People ask what changed between my first exit and my second. The market didn’t change. I didn’t get luckier. The difference was that the second time, I walked in knowing these three lessons.
We built Clermont with a buyer’s eyes on it, years out. We treated the first offer as a data point, not a deadline. And we knew exactly who we were with or without the company, which is what made it possible to walk away from a bad structure and hold out for a good one.
That thinking runs through the whole book. An exit isn’t something you bolt on at the end. It’s baked into how you pick the idea, build the team, set the margins, and choose your moment. Sell well and you buy your freedom. Sell badly and you buy a job with worse terms and a boss you didn’t pick.
I’d rather you learn these lessons from a newsletter than from a 1x multiple.
Entrepreneur Like a MOTHER comes out September 22. The full story of both sales, including the parts that still make me wince, is in the book.
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