Selling your business is a lot like selling your house… except instead of old carpet and questionable plumbing, you’re dealing with P&Ls, buyer egos, and the emotional baggage of letting go of your life’s work.
I’ve been through it. And if you’re reading this, there’s a decent chance you’re staring at a possible sale—or even deep in the weeds already—wondering: How the heck do I not screw this up?
Pull up a chair. Let’s talk shop.
Know Your Numbers Like You Know Your Favorite Takeout Order
Alright, here’s the cold truth: buyers don’t care about how “hard you’ve worked.” They care about how much money your business makes for them once they take over. Harsh? Sure. But fair.
I remember prepping for a meeting with a potential buyer—this was a guy who, I swear, wore a Bluetooth headset like it was a permanent body part. Mid-sentence, he’d say things like, “Run me through the EBITDA again?” as if he wasn’t just texting under the table two seconds ago.
Luckily, I had my financials dialed in. Clean books, updated profit and loss statements, cash flow projections—all wrapped up tighter than my Aunt Linda’s meatloaf.
Pro tip: If you have to explain what a number “probably” means, you’re not ready to negotiate.
Play Poker, Not Go Fish: Timing Matters
When you’re negotiating, don’t show your hand too early. I made that mistake once—got a little too excited, maybe even let the words “we’re really hoping to close this quarter” slip out. Instant leverage shift.
Suddenly the buyer knew I was feeling pressure, and guess what? That first offer came in way below what we discussed. Rookie move.
You want to walk into that room cool, calm, and collected. Even if your inner monologue is screaming, “What if this is the only buyer? What if they walk?”—don’t let it show.
Instead: Ask questions. Gather info. See what kind of buyer you’re dealing with before you start dropping hints about your bottom line.
Don’t Negotiate Alone (Unless You Enjoy Ulcers)
Hiring a business broker or M&A advisor might feel like you’re giving up a cut of your sale price—and technically, you are. But I can’t stress this enough: a great advisor pays for themselves.
I tried to handle one negotiation solo, thinking, “How hard could it be? I’ve been running this place for ten years.” Spoiler alert: it was hard. I got emotionally wrapped up in every back-and-forth, started second-guessing myself, and spent more time trying to interpret emails than actually running my business.
Once I brought in a broker, everything changed. They handled the gritty details, buffered the awkward conversations, and knew exactly when to push and when to pull back. It felt like upgrading from a rusty bike to a Tesla.
Emotions Are Real. Don’t Let Them Drive the Car.
Selling your business is personal. Even if you’re ready to move on, there’s still this little voice that says, “But what if they don’t take care of it? What if they change everything?”
I felt it. Every time a buyer hinted at rebranding or “streamlining” staff, I had to bite my tongue. But here’s the thing: once you sell, it’s not your business anymore. And if you let emotion run the negotiation, you’ll lose sight of the real goal—getting the right deal, not the perfect one.
Let yourself feel it. Talk it out with your spouse, your dog, your mirror—whatever works. But when it comes time to negotiate? Put your CEO hat on.
Price Isn’t Everything (Seriously)
There’s a moment in every negotiation when someone throws out a big number and your heart skips. They want to pay WHAT?!
But pause. Because terms matter more than you think.
Is it an all-cash offer or are they stringing it out over five years? Are there performance-based earnouts? Is there a non-compete that could handcuff your next venture?
I once had a buyer offer 15% more than another group, but the deal included a two-year earnout tied to metrics that made NASA algorithms look simple. No thanks.
The lower offer? It was clean. Cash-heavy. I could walk away with my dignity (and retirement) intact. And I did.
Control the Pace, Not Just the Price
Negotiations can drag. Or worse, they can rush.
Neither extreme is good.
If things are stalling, politely push for timelines. If they’re speeding toward the finish line, don’t let FOMO pressure you into skipping steps. You get one shot to sell this business—make sure you’re doing it right.
I kept a sticky note on my desk that read: “Is this on my timeline?” It helped keep me grounded. Because every buyer has their own agenda. That doesn’t mean you need to play along.
Key Takeaways
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Know your financials backward and forward—vagueness kills credibility.
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Control your emotions, or they’ll control your decisions.
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Never negotiate alone if you don’t have to—brokers are lifesavers.
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Dig into the terms, not just the headline price.
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Buyers will push the pace—don’t be afraid to slow it down.
Final Thoughts: The Exit Isn’t the End
Look, selling your business can feel like breaking up with someone you still care about. It’s weird. Emotional. Sometimes even anticlimactic. But it’s also a transition—a beginning.
I thought I’d miss the daily chaos, the customer emails at 10 PM, the mild panic when payroll hit. Turns out? I like sleeping. I like walking my dog without thinking about vendor contracts. I like freedom.
If you’re gearing up to sell, or already halfway through the process, just remember: negotiating the sale isn’t about winning—it’s about closing the right deal.
And if you ever find yourself staring at a buyer across the table, wondering if you’re saying the right thing, just think of me… nodding silently, mouthing the words:
“You got this.”