So, picture this: I’m sitting in my backyard with a half-cold cup of coffee, staring at a legal pad filled with doodles, numbers, and notes that only made sense to me at the time. I’d just told my accountant, “Yeah, I’m thinking about selling the business,” and he looked at me like I’d just declared I was going to live off the grid and raise alpacas.
That’s when I knew—I was really doing this.
Selling a business, especially one you’ve put your blood, sweat, and vacation days into, isn’t a simple Craigslist transaction. It’s more like navigating a jungle with a dull machete and no bug spray. I learned a lot, made a few wrong turns, and hopefully, by the time you finish reading this, you’ll avoid the traps I fell into.
Here are 10 common mistakes to avoid when selling your business, straight from someone who had to learn them the hard way.
1. Waiting Too Long to Prepare
You ever try to clean your whole house because a friend texted, “be there in 10”? Yeah, prepping to sell your business last-minute feels exactly like that—chaotic and slightly sweaty.
I waited until I knew I wanted to sell before getting my books in order, fixing operations, or even documenting my processes. Big mistake. Ideally, you want to start prepping at least 1–2 years before you actually list it. That gives you time to improve margins, clean up your financials, and build value that buyers will actually pay for.
2. Overvaluing Your Business
This one stings. I had a number in my head—let’s call it “The Dream Number.” It was based on emotion, ego, and a vague memory of what my cousin’s buddy got for his car wash chain. I ignored what the market would actually bear.
Don’t do what I did. Work with a valuation expert, like the ones on Business Broker News. A solid, data-backed valuation sets realistic expectations and prevents awkward “That’s adorable, but no thanks” conversations with buyers.
3. Hiding the Messy Stuff
There was a point where I thought I could “tweak” some of the less-attractive parts of the business during due diligence. You know, smooth over that one bad year, gloss over the employee turnover…
Buyers aren’t dumb. They will find everything. And if they feel like you’re hiding things? Trust goes out the window, deal dies on the vine.
Transparency builds credibility. It’s better to say, “Here’s a hiccup and how we’re fixing it,” than to get caught covering it up.
4. Trying to Do Everything Yourself
Look, I get it—your business is your baby. You don’t want anyone else feeding it, let alone selling it.
But unless you’ve sold a dozen businesses before, trust me on this: you need pros. I tried to juggle it all—marketing the sale, negotiating with buyers, running the day-to-day—and almost lost my mind (and a couple deals).
A good business broker, CPA, and attorney are worth their weight in gold. Let them do their thing while you focus on keeping the business healthy.
5. Not Vetting Buyers Properly
Oh man… the time-wasters. The “tire kickers.” The guy who scheduled four meetings and ghosted like he was auditioning for a dating app horror story.
Qualify your buyers early. Ask for proof of funds. Understand their intentions. If someone’s just curious or trying to “learn the ropes” on your dime, politely show them the exit.
6. Failing to Keep the Business Running Smoothly
This one’s easy to overlook. You’re emotionally checked out, you’re dreaming of retirement or launching your next gig—but if your numbers start slipping while you’re trying to sell? Buyers notice.
I had a slow quarter right when I started listing. It hurt the price and gave buyers the upper hand in negotiations. Keep grinding. Pretend you’re not selling and keep your team motivated, even if your head’s halfway on a beach already.
7. Overlooking Tax Implications
Here’s a fun surprise: just because someone hands you a big check doesn’t mean you get to keep all of it. 🤡
I didn’t fully understand how asset sales vs. stock sales would affect my bottom line—or how capital gains taxes would hit me like a truck. A good tax advisor can help you structure the deal to minimize what you owe Uncle Sam. Don’t wait until the ink’s dry to find that out.
8. Letting Emotions Get in the Way
I had to stop myself—more than once—from saying things like, “Well, if you don’t love this company like I do, maybe you’re not the right buyer.” 😅
It’s business. Buyers look at numbers, trends, and upside—not the time you slept in the office during your first product launch. Leave your heart in the background and keep negotiations professional.
9. Neglecting Confidentiality
Selling your business isn’t something you want on the office grapevine.
I let it slip to a vendor, and within a week, I had clients asking, “So… you selling?” That can freak out employees, suppliers, and customers. Use NDAs. Keep it tight. Control the narrative until the deal is solid.
10. Not Thinking About Life After the Sale
This part gets real. After the deal closed, I had a weird emotional crash. I’d spent years waking up with a purpose, and suddenly I was staring at my phone wondering if I should start a hobby or buy a kayak.
What’s next? Whether it’s a new venture, early retirement, or mentoring other entrepreneurs—plan for it. Otherwise, the “What now?” blues hit hard.
Final Thoughts: Learn From My Missteps (So You Don’t Repeat Them)
Selling your business can be one of the most rewarding experiences—financially and personally—but only if you do it right. I didn’t, at first. But the more I slowed down, brought in help, and got honest about the process, the better things turned out.
And hey, if you’re reading this with a cold coffee in your hand and a scribbled-up legal pad like I was, you’re already on the right track.
You got this.
Now go make a clean, smart exit—and maybe, just maybe, treat yourself to that kayak. 🚣♂️
P.S. Got a funny or painful business-selling moment of your own? Shoot me a message. Misery (and spreadsheets) loves company.