Why Working In Your Business Is Killing Your Exit Value

A client of William’s is likely heading to market later this year or early next to sell his business. The M&A team is in place, the quality of earnings conversation has started, and the groundwork is being laid for a strong exit. But a conversation from a couple of months ago kept coming back to William during a recent check-in call with the M&A team.

The business owner had been deep in the weeds renegotiating an insurance policy. Frustrated about an exclusion the insurance company had added that shouldn’t have been there. A completely understandable frustration. But William’s reaction was telling. Here is a business owner who is months away from a sale, spending his time and energy on an insurance policy that the new buyer will almost certainly redo entirely the moment they take over.

It is not a criticism. It is one of the most common patterns William sees in business owners approaching an exit. And it points directly to a problem that working in your business exit value makes unavoidable.

What Buyers Are Actually Looking For

When a buyer comes in for due diligence, they are not just working through your financials and reviewing your operations manual. They are asking a more fundamental question. Can this business thrive and survive without its current owner in the room?

If the answer is unclear, or worse, if the answer is obviously no, that uncertainty gets priced into the deal. A business that depends entirely on its founder to function is worth less than a business that runs efficiently without them. That gap in valuation is real and it is significant.

The CEO vs COO Problem

William connects this to a conversation from a recent Charting Opportunities episode where guest Mark Brinson talked about his own leadership journey. Mark’s honest admission was that he is working toward the CEO role but is still largely operating as a COO. Still in the day to day. Still the person the team turns to for operational decisions.

That tension is one of the most important things to resolve before going to market. The difference between a CEO and a COO isn’t just a title. It is the difference between working on the business and working in it. Between setting direction and executing tasks. Between building something that runs without you and being the thing that makes it run.

How to Start Elevating Yourself

The path out of the weeds is not complicated but it does require intentional effort. It starts with identifying the things you are currently doing that someone else on your team could do, or could learn to do with the right guidance. Then it requires doing something that does not come naturally to most business owners. Teaching those things and letting go of them.

The result is a business where the owner’s fingerprints are on the vision and the culture rather than the insurance renewals and the day to day blocking and tackling. That is the business a buyer wants to step into. That is the business that commands a premium.

Elevate yourself to the CEO role. Give the people around you the space to grow into the responsibilities you leave behind. And watch what that does to the value of what you have built.

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We have a client that is going to likely go to market sometime later this year, early part of next year to sell his business. We had a conversation with M&A team earlier this week and started talking about quality of earnings, M&A advisor, just making sure that the team is in place. And it’s funny, I, I went back and I started thinking about a conversation that I had with the founder earlier this year, or the owner earlier this year, and it was probably two or three months ago, and it was around the frustration he had in renegotiating his insurance policy and how the insurance company was excluding something that they shouldn’t have excluded.

[00:01:00] And I started thinking about it. I said, “Man, he’s classic business owner, which is still down in the weeds on the underlying aspects of the insurance policy.” And I wondered how much, if any, of that will be visible to the buyer as they come in and start looking at how the business will thrive and survive without him.

I mean, the reality is, is the business owner was negotiating an insurance policy that he’ll really never use as a result of, you know, potentially selling the business. The new folks will come in and, and redo everything underneath it. He didn’t know that at that time, so it’s fine that he– you know, that the policy needed to be renewed, obviously.

But it just goes back to, you know, the simple aspect, and at our charting opportunities last month, Mark Brinson did a really good job of talking about how [00:02:00] he’s trying to elevate himself to a CEO, and he’s trying to teach his team how to elevate themselves beyond their existing positions. But he’s not a CEO yet.

He’s still mainly operating as a COO. And I think that’s… You know, we hear so much about stop working in the business and start working on the business, um, processes, systems, uh, people in the right seats and all those things. But it really is just the day-to-day blocking and tackling, right? Like getting out of that aspect, allowing other people on the team the opportunity to grow and thrive into that so that, A, you’re less stressed out, B, you give those around you an opportunity to develop skills that they wouldn’t otherwise have, and C, when the opportunity comes for you to go about selling the business, as in this case very soon, the buyer can step in and see that the business functions extremely efficiently without you being there.

So just remember, [00:03:00] elevate yourself to CEO and allow those around you to thr- to thrive in the process. If you liked today’s video, hit the subscribe button down below, or better yet, just leave us a comment

ORIGINAL MEDIA SOURCE(S):

William Bissett: Are You a CEO or Are You Still Acting Like a COO? | Portus Perspectives

Originally Recorded on July 1, 2026

Portus Perspectives: Episode 28

By /Published On: July 11, 2026/