It was a good deal, on paper. The multiple was right where the broker projected, there were no surprises in diligence, the wire hit on a Friday. Six months later, the man who signed it told me he felt like he’d lost something instead of winning it. He wasn’t my client. I met him after, over coffee, through a mutual contact. Nobody on his side of the table had asked him the one question that would have told him the truth about what he actually needed.
He ran a commercial cleaning and facilities services business, a little over $4.5M in revenue, built over eighteen years. He’d found his own broker. No advisor doing double duty on anything but the math. Get the multiple right, get the deal done.
By month four he was calling old vendors just to have something to manage. By month six he asked me the question straight out: “I hit my number. Why does it feel like I lost something instead of winning it?”
I told him what he was feeling was common. I also told him it didn’t have to happen to him.
The Math Is Half the Job
Every owner I talk to has a number in their head. Some figure they’ve decided means “I can leave.” Advisors spend most of their energy getting that number right: EBITDA adjustments, multiple comps, deal structure. All of it matters.
The math tells you what the business is worth to a buyer. It doesn’t tell you what the sale is supposed to do for you personally. Most deal teams stop at the first question and never touch the second.
The Question Nobody Asks
Before I do any valuation work with an owner, I ask one question: what do you believe will actually change in your life once you hit this number?
Most owners haven’t thought about it directly. The honest answer is usually “I’ll finally feel like I did something with my life,” or “my spouse will stop worrying.” Sometimes it’s simpler than that: proof he’s not just his job.
Those are real needs. A wire transfer doesn’t solve any of them. I’ve watched this play out enough times to trust the pattern: an owner who believes the check will fix an identity problem, a marriage problem, or a self-worth problem cashes the check and finds the problem still sitting there, waiting for them on the other side.
What Skipping This Costs You
This isn’t just a soft, feel-good issue. It shows up at the negotiating table, before it ever shows up six months after close.
An owner who’s quietly hoping the deal will resolve something personal negotiates from need, not strength. He accepts the first credible offer. He caves on terms he shouldn’t. A sophisticated buyer doesn’t need to understand your psychology to exploit it. They just need to sense you want this done more than they do. That gap alone can cost a seller real money in the final price, structure, or earnout language.
Owners who negotiate well and still skip this work aren’t off the hook either. It doesn’t disappear. It waits. It showed up for the guy I had coffee with, a full six months after a deal that went exactly to plan.
Do This Before You Go to Market
If you’re planning an exit in the next one to three years, don’t wait for a broker or banker to ask you this. Ask yourself now.
- Write down your number.
- Next to it, write down what you believe will be different in your life once you have it.
- Be honest about which of those beliefs are actually about money, and which ones aren’t.
- For anything that isn’t about money, ask what would solve it whether you sell or not.
This takes an hour. Most owners never spend it. The ones who do go into a process clear about what the deal is actually for, and they negotiate like it.
I still think about that coffee. A good deal, on paper, that left him worse off than he expected going in. Nobody on his side of the table had asked him the one question that would have told him the truth about what he actually needed.
If you’re two or three years out from a decision, reach out. I’ll give you an hour, no pitch attached, to talk through what you’re actually solving for, and whether your number gets you there.
