Building to Leave
Why most owners call when they're ready to sell, not when they have time to prepare.
Most of the time, people call an M&A advisor when they want to sell their business. However, there is a pattern to these calls, and once I noticed it, it was really hard to “unsee.”
A client said it to me plainly the other way around. He figured people must call me all the time to talk through this stuff, to think it out loud before they're anywhere near a decision. I told him the truth, which is that they don't. The vast majority of people call when they believe they're ready to sell. Almost nobody calls when they have time to properly prepare to sell.
I didn't plan to say it that way and it wasn't a "prepared" thought, but it stuck with me afterward, because those are two completely different moments, and the differnece between them is the thing I want to talk about.
The Feeling
Ready is a feeling. It arrives. Something triggers it. Maybe you're tired in a way that sleep doesn't fix anymore. Maybe a kid you assumed would take over made it clear, gently or otherwise, that they won't. Maybe a number finally landed in your head that feels like enough or maybe someone made an offer out of nowhere and now you can't stop thinking about it. Whatever the trigger, “ready” shows up on its own schedule and announces itself. You wake up one day on the other side of a line you didn't know you were walking toward and now it takes up all your mental and emotional energy.
Prepared is not a feeling. Prepared is work, the kind of work you have to start long before you feel anything, at the exact moment when leaving is the furthest thing from your mind. That's the problem in one sentence. The emotional clock and the practical watch are in different time zones and they almost never sync up. By the time you feel ready, the runway you needed to prepare well has mostly ticked behind you.
So why doesn't the work get done earlier? Owners aren't stupid. Every one of them has heard the line about how the business should be able to run without you. They know it and nod along.
But preparing to sell means building toward your own absence. It means slowly, deliberately, making yourself unnecessary to the thing you built around yourself. That is a strange and unpleasant project to take on while business is good and you're still the person everyone (internally and externally) calls. Nobody wants to spend two or three years quietly rehearsing their own irrelevance. So it gets put off year after year. The owner understands what's required, that was never the problem. The problem is that doing it feels like a small daily betrayal of the role that's given their life its shape, and that role isn’t President of the Company, its owner of the Company, there is a big difference.
For some owners it's control, they don't want to give up control of any kind of daily operations. For some it's money, putting the leadership team in place to run a business without you is almost always going to cost more than you pay yourself. Whatever the reason, the decision gets made that they will handle this "soon, but not yet." None of this makes you a bad owner, it makes you a pretty normal one.
A huge problem is also that the triggers that finally make you feel ready are very often the same things that weaken the position you're now trying to sell from. Exhaustion. A health scare. A soft year. A market that turned. The reason the feeling of "now" arrives is typically concurrent with an event or timing situation that makes this exactly the wrong time to pursue selling. You're suddenly motivated to sell at precisely the moment the business looks its least sellable, and you've got the least (potentially no) time to fix it.
Holding Companies, family trusts and the like are often the ways that owners say to themselves "I have a trust set up, I have a holding company, I'm ready." Sure, from a tax perspective, but buyers don't really care about your tax situation.
The Fiction
Which brings me to the story owners tell themselves to make all of this feel fine.
It goes something like this: When I'm ready, I'll just make a few calls. I know people, folks who've bought businesses in my industrym maybe competitors, a supplier or two, maybe someone who sniffed around years ago. My business is spectacular. I'll call them, they'll see what I see, they'll buy it, I'll get my money, and I'll move on.
This story is very comforting, and I completely understand why. It lets you wait and turns preparation into something you can skip until the last moment, because the exit is already handled in your imagination. The trouble is that almost none of those assumptions survives contact with reality.
Start with the calls. The assumption is that the buyers are just sitting there, warm, waiting for your number to come up. They're not. Interest from years ago is not interest today and a friendly relationship is not a transaction. The person who once said they'd love to own something like yours was talking about a feeling, not signing anything.
Then "my business is spectacular" and as an owner, it probably is. But spectacular to operate and spectacular to buy are not the same thing, and the difference is almost always you. A buyer isn't purchasing your pride or your history or the relationships that live in your head and walk out the door when you do. They're purchasing cash flow that survives your departure. If the business is spectacular because you are spectacular at running it, you haven't built an asset. You've built a job that only you can do, and nobody pays a premium for that. We've written extensively about Key Man Risk, and I won't go into more detail on it here.
"They'll buy it" assumes interest equals a deal, that nothing surfaces in diligence to cool the room or carve down the price. Something always surfaces. The pattern is almost boring once you've watched it a few times. The call gets returned. There's real enthusiasm, a lunch, some talk of how well the two operations would fit together. And then it slows. The customer concentration nobody had thought about. A key supplier relationship that turns out to live on a handshake. Add-backs that don't hold up under a second look. The deal doesn't blow up so much as quietly cool, and months later the owner still isn't quite sure what happened. "I'll get my money" assumes the number in your head is the number on the table, that earnouts and holdbacks and the year they want you to stay on don't quietly reshape it into something smaller and slower than you pictured. And "I'll move on" assumes a clean break, which, if you've read anything else I've written, you know is rarely how it goes.
None of this means the calls never get made or the deals never happen. They do. But the version where you wait until you feel ready and then dial your way to a clean, rich exit is mostly a fiction. It's the story that justifies not preparing, and the not preparing is what makes the story so hard to deliver on.
The Acceptance
So here's the reframe, and it's the only useful thing I have to offer, because it isn't a checklist and it isn't a deadline.
The time to prepare is the moment you accept that you'll leave eventually. Not next year, not in two years, not at some specific exit you've circled on a calendar. The timeline genuinely doesn't matter. What matters is the shift from building without a plan to building to leave.
Those are two different businesses, even if they look identical from the outside. Building without a plan means building around yourself, because that's the natural thing to do and it feels good to be indispensable. Every decision routes through you, and you get a little hit of importance every time it does, and the whole structure quietly becomes worth less and harder to hand off with every year that passes. Building to leave means making decisions with someone else in mind, the person who eventually has to run this thing, value it, want it. It means the business gets a little more able to stand on its own each year instead of a little more dependent on you.
The gift in that reframe is that building to leave is worth doing whether you sell next year or never. A business that runs without you is just a better business. More valuable, more durable, easier to step back from when you want a month off or a health issue forces your hand. I used to joke that building a team around you was vital so you could actually have a summer holiday and have a profitable business to come back to. You don't have to be selling to want that. You just have to admit, once, that someday you won't be the one holding it.
Most owners can't quite bring themselves to admit that until the day they desperately want out. And by then they're making calls from the worst possible position, telling themselves the comfortable story, hoping it holds.
It's a better thing to know early, not because you're going soon (you might not be going for years) but because the leaving is coming either way. And the only real choice is whether you build like you know it.
Ready to Talk?
You don't need a timeline, or a reason, or a decision already made. If this is rattling around in your head, that's reason enough to start a conversation. No pressure, and no assumption that you're selling anything soon. Reach out whenever you want to think it through.