December does something funny to business owners.

You finally slow down.
The inbox quiets.
The calendar gets lighter.

And suddenly, all the things you’ve been postponing show up uninvited.

Not next quarter.
Not “after this busy season.”
Now.

Here’s the uncomfortable truth most owners never hear until it’s too late:

Very few businesses are sold when the owner wants to exit.
Most exits happen when the owner is forced to.

And forced exits don’t come with leverage, clean deals, or great outcomes.

They come with stress, discounts, and regret.

The Real Reason Most Exits Go Sideways

It’s not market conditions.
It’s not timing.
It’s not even valuation.

It’s that most owners never plan for an exit because they assume they’ll decide when it happens.

Reality has other plans.

In exit planning, we call them the 5 Ds. And they don’t care about your calendar, your goals, or your to-do list.

The 5 Ds That Force Business Owners Into Bad Exits

1. Death

Let’s not sugarcoat it.
If something h...

So, you've built a business from the ground up, shed a little blood, a lot of sweat, and probably some not-so-pretty tears. Now, the thought of an “exit” is on your mind—whether it’s about cashing in, passing it on, or even retiring on a beach. But preparing your business for a smooth and profitable exit? That’s an art, my friend. So, let’s dig into what it takes to sell smart, sell high, and leave with no regrets.

Start with the Big Question: Who’s Buying?

When it comes to selling, you need to know your audience. Turns out, Wall Street is looking for Main Street businesses. As we covered in our recent episode of The Liquid Lunch Project with Jordan Wagner, private equity firms are interested in the “boring” essentials—think HVAC, plumbing, and property management. Why? Because these businesses offer steady, recurring revenue and a reliable customer base. So, if you’re the proud owner of a “boring” business, know that you might be sitting on a goldmine.

Nail Down Your Numbers