Thinking About Selling Your Business? Here’s What I Wish I Knew About Brokers
I’ll shoot straight with you—when I first thought about selling my business, I assumed I could do it solo. I mean, how hard could it be? Slap a price tag on it, talk to a few folks, maybe shake some hands, and boom—retirement on a beach somewhere.
Yeah… no. That fantasy lasted about as long as a New Year’s resolution.
After two months of tire-kickers, one guy who wanted to “trade equity for a boat” (seriously), and a few meetings that felt more like therapy sessions than business pitches, I realized I needed help. The kind of help that knows what EBITDA actually means and doesn’t get weird when you say the word “multiples.”
Enter: the business broker.
But not just any broker—the right one. And finding that person? It took some serious trial and error (and a little humble pie). So here’s how I navigated the broker jungle without ending up on a “Don’t Be This Seller” warning list.
What Exactly Is a Business Broker?
If you’re picturing someone in a cheap suit waving a clipboard, pause. A legit business broker is more like a seasoned translator, part-therapist, part-dealmaker, and full-on strategist. They sit in that weird Venn diagram where spreadsheets, psychology, and salesmanship all overlap.
Their job? Help you value your business, find qualified buyers, keep things discreet, and guide the entire sale process without it falling off the rails. Think of them like the Sherpa who gets you to the summit and reminds you to breathe on the way up.
Red Flags, Gut Checks, and Why Google Reviews Don’t Tell the Whole Story
I made the rookie mistake of starting with the first broker that popped up on Google. “Top-rated,” five stars, all smiles on their website… But something felt off. First meeting, the guy talked at me, not to me. I asked how he’d value my business, and he gave me a range that felt like he just pulled it out of a hat.
Lesson #1: Go with your gut. If someone talks over you, rushes your questions, or makes promises that sound like infomercial pitches (“We’ll sell it in 30 days, guaranteed!”), run—don’t walk.
The best brokers ask thoughtful questions. They listen. They don’t sell you a dream; they walk you through reality, even when it’s not pretty. And they know the market better than your bar trivia champion buddy knows 90s sitcoms.
Credentials Matter, But Chemistry Matters More
Don’t get me wrong—experience, certifications, and deal volume are all important. You want someone who’s closed sales in your industry, understands local or national trends, and knows how to deal with legal, tax, and negotiation hurdles.
But what surprised me the most? The broker I ended up working with wasn’t the flashiest or the one with the biggest firm. He just got me. He understood what I built, why I cared about who I sold to, and what kind of legacy I wanted to leave.
He even asked about my dog, Leo. (Solid move.)
Ask These Questions (Before You Sign Anything)
Here’s the short list I wish someone gave me sooner:
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How many businesses like mine have you sold?
Industry-specific experience is gold. -
What’s your process for valuing a business?
If it involves buzzwords and not hard data, beware. -
How do you find and screen buyers?
The answer should not be “Craigslist.” -
What are your fees and when are they paid?
Commission-only is standard. Upfront fees? Tread carefully. -
How do you keep the sale confidential?
You don’t want your employees finding out from Facebook.
And the kicker: Can I talk to a few of your past clients? If they squirm or dodge, something’s fishy.
The Right Broker Won’t Just Close the Deal—They’ll Protect It
The broker I ended up working with did more than just match me with a buyer. He managed egos, soothed nerves (mine included), and caught things my lawyer almost missed in the LOI.
He also knew when to push, when to pause, and when to pop open a bottle of something strong because “this deal’s going sideways fast.”
Selling a business isn’t just numbers and signatures—it’s emotion, legacy, timing, and trust. And the right broker understands that balance.
Finding the Best Broker Is a Lot Like Dating (But Less Swiping)
It’s weirdly personal. You want someone who’s professional but human, driven but not pushy, smart but humble. Someone who respects what you’ve built and isn’t just chasing a commission.
I interviewed five brokers before landing on “the one.” Every hour spent doing that homework saved me weeks of headaches later.
Would I go through the process again? Not anytime soon. But if I did, I’d start the same way: with patience, curiosity, and a big ol’ list of questions.
Final Thoughts (aka Let’s Land This Plane)
If you’re serious about selling your business, don’t wing it. The best broker isn’t necessarily the biggest name or the one with the slickest pitch. It’s the one who listens, understands your goals, and knows how to get you there without wrecking the thing you worked so hard to build.
So take your time. Ask the hard questions. Trust your instincts.
And when in doubt, remember: boats for equity is not a solid deal structure.
Key Takeaways
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Not all brokers are created equal. Vet thoroughly.
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Industry experience beats general deal volume.
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Chemistry matters—don’t ignore your gut.
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Ask detailed questions before signing a listing agreement.
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A good broker does more than sell—they guide, protect, and advocate.
That’s my story, friend. Hope it helps you avoid a few landmines and find the kind of broker who helps you walk away proud—with a deal worth smiling about and maybe, just maybe, a beach in your future.