I get this question a lot. And honestly, most people ask it before they’re ready to admit they’re asking it.

They’ll call it “just curious.” They’ll say they’re asking for a friend. But what they really mean is I’ve been thinking about this. I just don’t know how to start the conversation.

So let me try to make it easier.

There’s no perfect time to sell a business. I’ve never met an owner who woke up one morning and said “yep, today’s the day” with complete certainty. But I have noticed that the owners who exit well — who leave with the number they wanted and sleep soundly afterward — tend to have a few things in common before they ever pick up the phone.

The first one is this: they stopped being the most excited person in the room about their own business.

That might sound like a bad thing. It’s not. It means they’ve built something real, something that runs, something they’re proud of and they’re starting to think about what comes next. That shift isn’t disengagement. It’s readiness. And it’s usually the first honest signal.

The second thing I notice is that their financials are telling a good story. Three solid years. Clean books. A number that holds up when someone looks closely at it. Owners who try to sell in a down year, or right after a messy stretch, almost always regret the timing. The business is worth more when it looks like what it actually is — something worth buying.

Third, and this one surprises people, is that the best time to sell is usually before you feel like you have to. I’ve sat across from owners who waited too long. Health issues. A partner who wanted out. A market that shifted. When you’re selling from urgency, you’re negotiating from weakness. When you’re selling because you’re choosing to, you have leverage. There’s a real difference in the final number.

I also think about market conditions, because they matter more than most business owners realize. Right now, private equity firms have more capital allocated to acquisitions than at almost any point in the last decade. Businesses in the $5 million to $25 million EBITDA range are exactly what they’re chasing. That window won’t stay open forever. Owners who are even two or three years away from a sale should be thinking about this today, because preparation takes time.

Here’s what I’d tell you if you called me right now: you don’t have to be ready to sell to have this conversation. Most of the owners I work with start talking to me a year or two before they actually go to market. We figure out where they are, what the business is worth, what’s standing in the way of a better number — and then we have time to actually fix it.

That’s what the Snapshot Valuation is. It’s not a listing. It’s not a commitment. It’s just clarity. And most people find that after they have it, the decision gets a lot easier.

If you’ve been thinking about it, even just quietly, reach out. The conversation costs nothing. The information is free.

That’s kind of my whole thing.

Jake Taylor, Exit With Jake
Veteran. Business exit advisor. Working with owners doing $5M–$25M in EBITDA, anywhere in the country.

→ Start with a free Snapshot Valuation at ExitWithJake.com