Call him Gary. He isn’t any one owner we’ve met; he’s four or five of them, blended enough that no one has to see themselves in a blog post, and every detail below has happened to someone. That’s the point of telling it.
Gary ran a good MSP in a mid-sized market for twenty-six years. Not spectacular, good: forty-some clients, eight employees, real recurring revenue, his name known at the chamber and the counter of the diner near the office. He thought about selling the way most owners do, which is to say annually, briefly, in the truck after a hard week, and always with the same conclusion: not yet. The business was still growing a little. The multiple might be better next year. His best tech wasn’t ready to lead. There was no rush, and he was only fifty-nine, and the thinking always dissolved by Monday because thinking about it felt like planning a funeral for something that was obviously still alive.
What Gary had instead of a plan was a feeling that he’d know when it was time. It’s worth pausing on that feeling, because nearly every owner carries it, and it has a flaw that’s invisible until it isn’t: it assumes the timing will be his to choose. Every scenario in Gary’s head began with Gary deciding. None of them began the way these things actually begin, which is with a phone call.
For Gary, the call was a cardiologist’s office, moving up an appointment. For the owner two towns over it was his senior engineer, the one carrying half the tribal knowledge, giving notice because a platform-backed competitor offered him a number Gary couldn’t match. For a third it was the anchor client, 28% of revenue, announcing a “strategic review of vendor relationships” the quarter after their new CFO arrived. The specific call doesn’t matter. What matters is what all three versions share: the moment it comes, the owner is no longer selling a business. He’s selling a situation.
And situations price differently. Watch what happened to Gary’s leverage in the six months after his call, because it’s mechanical. His timeline collapsed, so the two-year runway of fixes (the concentration, the documentation, the contracts still on handshakes) became a disclosure list instead of a work plan. His alternatives collapsed, because a man who must sell within a year can’t credibly walk away, and buyers price walk-away credibility precisely. Even his energy collapsed, and tired sellers concede, one small term at a time. The business hadn’t changed at all. Its earnings were identical to the year before, when Gary had idly valued it in the truck. But the year before, a buyer would have been pricing a company. Now they were pricing a countdown, and every party at the table could hear it ticking except, for a while, Gary, who kept using last year’s number in a situation that had repriced it by a third.
Here’s the part that would have offended him to hear at fifty-five: none of this was bad luck. The call always comes. Health, key people, anchor clients, markets: an owner in his sixties holding an undiversified, illiquid, personally-dependent asset is running a portfolio a first-year finance student could critique, and “I’ll know when it’s time” is not a hedge. The actuarial tables don’t negotiate, and neither do a competitor’s recruiters or a new CFO with a consolidation mandate. The only variable Gary ever controlled was whether the call would find him with a plan or without one.
So what does the plan look like, for the owner reading this in the truck? Not a sale. That’s the misunderstanding that keeps owners from building one. A standing plan is quieter: the business kept diligence-ready as a habit (clean books, documented addbacks, papered contracts), a second-in-command genuinely developing rather than perpetually not-ready, the twelve questions answered and dated in a drawer, a real number for what the business is worth refreshed every year or two, and one or two relationships with credible buyers who know your name before anyone needs anything. Total cost: a few days a year. Total effect: when the call comes, and it comes for everyone, it starts a process instead of a fire sale. The owners who exit well aren’t the ones who timed the market. They’re the ones who were permanently ready, so that any year could be the year, on their terms.
Gary’s story ended okay, which is why he made it into the composite. The health scare resolved into medication and a warning, the sale closed eight months later to a decent buyer, and the discount, while real, wasn’t ruinous. He golfs now, and he’s honest over a beer in a way owners rarely are in blog posts. What he says is this: the money mattered less than he’d thought, and the panic more. He’d spent twenty-six years being the man with a plan for every client’s disaster, and the one contingency he never wrote a runbook for was his own. Then he taps the table and says the sentence we’ve heard, in some form, from every version of Gary we’ve ever sat across from: “I knew for ten years I’d sell someday. I just never let ‘someday’ pick a date, so it picked one for me.”