Matthew R. Meehan is a leading finance expert and CEO of Shield Advisory Group. He specializes in helping SMEs access credit and capital.
Over the years, I’ve talked to hundreds of sharp, successful and driven business owners who know their stuff inside and out.
But when I bring up exit planning? They look at me like I’ve got two heads.
I hear a lot of:
“I’m not ready to sell.”
“I’ve still got a lot left in the tank.”
“I’ll think about that when I’m closer to retirement.”
But here’s the thing: Waiting until you have to exit is the worst time to plan for it.
Whether it’s burnout, bad timing or one of the dreaded five D’s (we’ll get into that), too many business owners end up walking away from their business with a fraction of what it’s worth.
Today, I want to talk about why your exit strategy shouldn’t be a dusty document sitting at the bottom of a drawer; it should be an integral part of your business strategy.
Here are the top reasons why planning your exit now will be one of the smartest moves you can make in 2025.
Sell when you want, not when you’re forced to.
Here’s the truth: Most owners won’t get the luxury of choosing their exit timeline. They’ll get pushed out by a sudden divorce, a health scare or a falling-out with a partner, or (worst of all) they get T-boned in the middle of an intersection. Morbid? Yes. But that’s reality.
Having a plan means you’re not scrambling when life throws a curveball. A plan means your team knows what to do, your family is protected and you’re not forced to sell before you’re ready.
Your business is (probably) your biggest asset.
In my experience, for most entrepreneurs, 80% to 90% of their net worth is tied up in their business. Unfortunately, very few know what it’s actually worth or, more importantly, what it could be worth with the right moves.
That’s why getting a proper business valuation is step one. It will help you identify your wealth gap, profit gap and value gap … and then build a plan to close them.
Translation? You’ll know how far you are from walking away rich (or at least very comfortable).
And let’s be real: Some business owners have an overinflated idea of what their company’s worth is because “a buddy” supposedly sold a similar business for some insane number. But without knowing the full story (terms, conditions, earnouts, debt, etc.), that kind of comparison is nothing more than a barstool myth. A valuation clears the fog.
Maximize your value while you still can.
Building value takes time. You don’t wake up one day, decide to sell and magically get a seven-figure offer.
The best deals? Those go to businesses that are attractive and transferable. That means you need strong financials, systems that don’t rely on you, loyal customers and a team that can run things without you in the room.
It’s about making your business better today so that it’s worth more tomorrow.
Avoid the exit regret trap.
Do you know why 75% of business owners regret selling their business within a year? In part, it’s because they only planned the transaction—not the transition.
Exit planning isn’t just about the money. It’s about building a business that’s both significant and successful. It’s about knowing what you’re going to do with your life when the phone stops ringing and the business cards stop printing.
Purpose matters. Make sure you have one before selling.
Protect yourself from the five D’s.
The Exit Planning Institute highlights five D’s in exit planning. Let’s break ’em down:
1. Death: I know no one wants to think about it, but what happens if you’re suddenly gone? Who gets what? Who runs the business? Do they even know how? Don’t burden your family, colleagues or employees with questions they don’t have answers to.
2. Divorce: As much as we may try, our personal lives affect our business more than we think. Without a plan, your business could end up on the negotiating table. Protect it like the asset it is.
3. Disability: Accidents happen. People get sick. Expect the unexpected. If you can’t work, can your business still run? Will income keep coming in? Can you continue paying your bills? What happens to your employees?
4. Distress: Remember 2020? Enough said.
5. Disagreement: Business partners don’t always see eye to eye forever. Better to have a plan than a lawsuit.
Exit planning helps you bulletproof your business from all five.
Attract buyers, even if you’re not looking.
A best-in-class business is always being watched. Maybe it’s a competitor. Maybe it’s a private equity firm. Maybe it’s your own employees.
If your business is valuable, profitable and well-positioned, you don’t have to chase buyers. They come to you. That’s real leverage.
Build a legacy, not just a business.
Imagine spending your whole life building a business—the time, the money, the energy—only to watch it fizzle out when you walk away. Nobody wants that. You want it to mean something. You want it to impact your employees, your community, your family.
Having a solid exit plan in place ensures that what you build keeps going strong, with or without you. Legacy isn’t about ego. It’s about impact. Don’t let all those years of hard work go to waste.
Final thoughts: Start now, even if you’re not ready.
Think about it: You don’t wait until the rain starts to buy an umbrella, so why wait until it’s time to sell to put a plan in place?
An exit plan isn’t about selling tomorrow … or even next week or next year. It’s about taking action to build a better business today. Play the long game, and when it comes time to sell, buyers will be banging down your door to buy it—and you’ll be ready to transition into your new phase in life.
At my company, we help business owners unlock their value, align their business and personal goals and design a future they’re actually excited about. Whether you’re selling in 10 months or 10 years, the best time to start planning was yesterday. The second-best time is right now.
The information provided here is not investment, tax or financial advice. You should consult with a licensed professional for advice concerning your specific situation.
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