How To Negotiate the Best Deal When Selling Your Business

Okay, let me set the stage real quick.

I had just come off a 10-year run building this niche digital marketing agency—nothing fancy, just solid systems, a few kickass employees, and loyal recurring clients. We weren’t Google, but we were profitable. Real money. Good margins. But after a decade of late-night Slack messages and caffeine-fueled pitch decks, I was done. Cooked. Toasted.

So I decided it was time to sell.

Easy, right?

Spoiler alert: nope. But somehow—through a mix of instinct, hard lessons, and negotiating like my mortgage depended on it—I pulled off a deal I was actually happy with. Let me walk you through how I did it, because trust me: there’s a way to win this game without feeling like you just got mugged in broad daylight.

Step One: Know What You’re Really Selling Your Business

I thought I was selling a “digital agency.” But the first buyer I talked to hit me with:

“Okay, but what happens to the revenue if you leave?”

Cue the existential crisis.

That’s when it hit me: I wasn’t selling a business. I was selling certainty. Predictable income. Transferable systems. Client relationships. I had to reframe the narrative from “here’s what we do” to “here’s why it prints cash, even without me.”

So before even thinking about negotiations, I cleaned house:

• Documented every process like I was writing IKEA instructions.

• Systematized onboarding, delivery, reporting, the whole shebang.

• Rejigged client contracts to be transferable and auto-renewing.

It’s not sexy work. But when a buyer sees turnkey, they see value—and you’ve got your first negotiation chip.  This was a huge shift for me and I learned a lot about how to create systems to make my business a more attractive option to sell by reading the blog on True Business Builders.

Step Two: Don’t Just Take the First Offer (Even If It’s Sexy)

The first offer I got came in hot. Like, “wait, that’s more than I expected” hot.

And I almost took it. Almost.

But then I remembered something Gary Vee once said that stuck with me:

“The best deal is the one that plays out well long-term—not the one that looks prettiest on paper today.”

So I sat on it. Let it marinate. I used that first offer to create a sense of demand. Quietly told a couple other buyers, “Hey, I’ve got someone serious at the table. If you’re still interested, now’s the time.”

That’s when things got spicy. ️

A second buyer entered the ring. Then a third. I went from being the one chasing to being the one choosing. That leverage? Priceless.

Step Three: Shut Up and Listen (Like, Really Listen)

Here’s a weird thing about negotiating: people will tell you exactly what they want, if you shut up long enough.

I’m not naturally patient. I tend to talk fast, sell hard, and fill every silence. But during negotiations, I made a conscious decision to be 20% quieter than usual. (Not a scientific formula. Just… quieter.)

One buyer said something like:

“What’s important for us is having a transition plan where you stay on for at least six months.”

Boom. Data point.

Another said:

“We’re looking for businesses with client retention north of 90%.”

Double boom. Another chip.

Every word a buyer says is a breadcrumb. Follow them. Build your pitch around what they want. Then you’re not selling—you’re offering them the exact solution they’re looking for.

Step Four: Counter, But With Tact

Alright, here’s the fun part. Counteroffers.

Let me be clear: you don’t need to be a shark to negotiate well. But you do need to be clear on what matters to you.

Here’s what I countered on:

• Price: I didn’t go crazy. Just nudged it up 10% and attached it to concrete value (e.g., pipeline deals already in motion).

• Payout Structure: One buyer wanted to stretch it out over three years. Nope. I negotiated 70% upfront, 30% over 12 months max. With performance triggers.

• Post-Sale Role: One offer had me working full-time for a year post-sale. No thanks. I said 90-day consult, then peace out. That one stuck.

The key? Be flexible on stuff that doesn’t kill you, and firm on what matters. Think of it like poker—you don’t show all your cards, but you do protect your hand.

Step Five: Use the Lawyer (Even If It Feels Overkill)

At first, I thought I could save money by doing most of the legwork and “just having a lawyer look things over at the end.”

What a dumb idea.

You need a deal-savvy attorney. Not just any lawyer. One who knows acquisitions, asset transfers, earnouts, clauses, reps & warranties, the works.

Mine caught a clause buried deep in the APA (Asset Purchase Agreement) that would’ve made me personally liable for client churn six months after the deal closed. Uh, no thanks.

Best $4K I ever spent.

Step Six: Be Human

You know what closed the deal, though?

Not price.

Not fancy pitch decks.

Not legal wizardry.

It was this Zoom call with the lead buyer, where I just talked about what I built. My struggles. The years I almost quit. The stuff I learned. Why I cared about my team.

And I could see it landed. Their tone changed. They stopped seeing me as “the seller” and started seeing me as “the founder.”

Negotiation isn’t war. It’s a handshake, just a detailed one. Empathy closes deals.

Step Seven: Walk Away If It’s Not Right

This might be the hardest lesson I learned.

One deal was 90% there. But the buyer kept dragging their feet on payment terms. “We just need another week.” “Our financing is getting finalized.” “We’re adjusting the cap table…”

It was dragging into month three. My gut was screaming: get out.

So I walked.

Felt awful. Like ripping up a winning lottery ticket. But two weeks later, another buyer closed clean, with better terms. Lesson?

Don’t be so hungry to exit that you ignore the red flags.

The best negotiation sometimes is the one where you don’t sign.

Final Thoughts: You Don’t Need to Be a Killer to Win

Look, I’m not a negotiation guru. I didn’t go to Wharton. I didn’t sell for eight figures.

But I got the deal that was right for me. That let me walk away proud, paid, and at peace.

So if you’re about to sell your business and you want to negotiate the best deal?

• Get clear on what matters to you.

• Create leverage where you can.

• Listen more than you talk.

• Push back respectfully.

• Use real pros for the technical stuff.

• Be human. Seriously.

And when the time’s right? Step back. Let the deal land. And breathe.

You built something real. Now make sure you exit just as intentionally.

Key Takeaways: How to Negotiate the Best Deal When Selling Your Business

• Know your value—not just what you do, but why it’s attractive to a buyer.

• Leverage demand by shopping offers and creating a sense of competition.

• Listen closely during early calls—buyers will often tell you exactly what they want.

• ✍️ Counter with confidence, but stay flexible on the less-critical stuff.

• ⚖️ Lawyer up, and make sure they specialize in business deals.

• Be real—authenticity builds trust, and trust closes deals.

• Don’t ignore red flags—if a deal feels sketchy, walk.

Ready for a Successful Exit?

Selling your business is a big freaking deal. Emotionally, financially, existentially—it’s huge. But if I could do it, without selling my soul or losing my mind, so can you.

If this helped, or you’re in the middle of a sale right now and feel stuck—drop a comment. Let’s talk.

Catch you on the other side.

Frequently Asked Questions About Negotiating the Sale of Your Business

How do I figure out what my business is worth before negotiating?
Great question—and super important. Start with your earnings (usually EBITDA or SDE), then apply a multiple based on your industry. But don’t stop there. Things like recurring revenue, solid SOPs, and loyal clients can bump your valuation. Pro tip: Talk to a broker or get a valuation done so you’re not just throwing darts in the dark.

What’s the biggest mistake sellers make when negotiating?
Honestly? Getting emotional. Look, it’s your baby—I get it. But if you get too attached to a number or let ego drive the convo, it’s game over. Be firm, but flexible. And always be ready to walk if it doesn’t feel right.

Should I accept the first offer I get?
Nope. At least, not without shopping it around a bit. Even if it seems like a dream number, you might be able to negotiate better terms or find a buyer who actually gets your business. Leverage is everything.

How do I protect myself legally in the deal?
Get yourself a lawyer who knows M&A deals—not just your cousin who handled your speeding ticket. You’ll need solid contracts that cover liability, earn-outs, non-competes, and what happens post-sale. Trust me, don’t wing this part.

Is it better to sell to someone I know?
It depends. Selling to a friend or employee might make the transition easier—but it can also get awkward real quick if things go sideways. Keep it professional. Even with someone you trust, use contracts, lawyers, the whole nine yards.

Any tips for staying sane during the process?
Deep breaths. Long walks. And don’t check your email every five seconds. You got this.