Where a Good Exit Starts
April 21, 2026 •
By Jason:
I spend a lot of time talking to business owners and the eventual exit from the business comes up a lot.
Most business owners have thought about it, but many don’t really know how, or even if, they’ll ever get there.
And that’s often because they haven’t brought it up with their advisory team, and their current set of advisors haven’t asked them about it, either.
So it stays in the back of the business owner’s head, late at night, in between everything else. It’s never been made real. Nobody on their team has ever sat down and asked the right questions.
So here are the three questions, one for each stage of where you might be. If your advisors aren’t asking these, you can bring them up. And if they aren’t answering these, it’s time to ask why.
STAGE 1 — JUST STARTING TO THINK ABOUT IT
A direct question you can ask your advisors: “Which of you can help me figure out how much I need to sell this thing for to live the life I want afterward?”
Not a nice round number you anchored to because it sounded right. The real number, rooted in what your life actually costs, what you want to do next, and what your family needs.
I hear “ten million” a lot. Why ten million? Most people can’t tell me. If you’re working toward a number that isn’t tied to your actual life, you might be working toward the wrong target entirely.
STAGE 2 — EXIT IS ON THE HORIZON, MAYBE 2 TO 3 YEARS OUT
You may want to ask: “What do I need to do in the next two years to close the gap between what the business is worth today and what I need it to be worth?”
Once you know your number, the gap becomes your filter for every decision you make. Should we buy more trucks? Take on that new initiative? Run it through that filter. The things that actually close the gap might become the priority. The things that don’t might just have to wait.
And here’s what I find interesting: the things that make your business more valuable to a buyer also just make it a better business. More profitable, less dependent on you, better team. Some owners even get there and go, maybe I want to keep this, or pass it on to family.
STAGE 3 — OFFERS ARE ON THE TABLE
A question to consider: “Does this deal structure actually get me to my number, and have we done the tax planning around how this money is coming in?”
You might think you got ten million dollars. But if three of it is rolled into stock in the acquiring company and four more is tied to hitting earn-out markers over three years, what did you really get?
These buyers have done this a hundred times. You’re going to do it once. The number is one piece. The terms are where the devil lives. So make sure somebody on your team has been around that table before.
Those are the questions for your team. One’s we’d be asking and answering if we were quarterbacking this with you.
But here are a few questions just for you.
At the end of the day, when you’re looking at that big check, you want to be able to answer these confidently:
1) Did the exit hit my number?
2) Did I keep what I earned?
3) And do I know what comes next for my time, my money, and the people I care about?
Because that’s really the whole point, right?
Interested in how this works? Let’s talk.
Book a JobWalk with me and we can start the conversation.
Interested in other Rungs? Check out:
- The full Ladder here or the audio edition here
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HFM Investment Advisors, LLC is a registered investment adviser. All statements and opinions expressed are based upon information considered reliable although it should not be relied upon as such. Any statements or opinions are subject to change without notice. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. All investments involve risk and are not guaranteed. Information expressed does not take into account your specific situation or objectives and is not intended as a recommendation appropriate for any individual. Listeners are encouraged to seek advice from a qualified tax, legal, or investment advisor to determine whether any information presented may be suitable for their specific situation. Past performance is not indicative of future performance.
