Let me tell you something. I’ve bought a lot of things in my life. Sports cards. Wine. Companies. And the one thing I’ve learned the hard way? Walking up to a competitor and saying “hey, wanna sell?” is a lot like asking someone if they’d consider trading their dog. You might get a polite laugh. You might get a door slammed in your face.
I once watched a guy march into a rival’s office with a term sheet in hand and zero context. Three months later, they were in a bidding war over a customer contract that neither of them actually wanted. Ego is expensive, friends. Way more expensive than a good advisor.
So here’s the playbook I wish I’d had twenty years ago.
Do Your Homework Before You Say a Word
Before you even think about the conversation, you need to know three things cold:
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Their financial reality. Revenue, margins, debt. If you can’t estimate it, you’re not ready.
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Their emotional reality. Is the founder tired? Is there a succession problem? Did they just lose a big client?
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Your actual rationale. “It would be cool to own them” is not a strategy.
Quick story. I spent six weeks once just talking to everyone from my business broker at San Francisco Business Brokers Edge to suppliers and former employees of a company before I made a single call. Turned out the owner had been trying to wind down for two years but couldn’t figure out how. That conversation took eleven minutes. Because I wasn’t selling. I was solving.
The First Call Is Not a Pitch. It’s a Pulse Check.
Here’s where most people blow it. They treat the initial outreach like a sales presentation. Wrong move. The first call should be low stakes and slightly vague. Something like: “Hey, I’ve always respected what you’ve built. Would you be open to a coffee sometime? No agenda, just curious about your thinking on the market.”
You’re checking the temperature. You’re not putting a ring on it.
And whatever you do, don’t bring your whole team. One person. Two max. A crowded table feels like an ambush, and ambushes breed defensiveness.
Lead With Curiosity, Not Your Checkbook
When you finally sit down, ask questions. Real ones.
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What’s the part of the business that keeps you up at night?
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If you could wave a wand and change one thing, what would it be?
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What does the next five years look like in your head?
Then shut up and listen. I mean it. Count to five in your head before you respond to anything. You’ll learn more in that silence than in an hour of talking.
Here’s the counterintuitive part. You have to be genuinely okay with walking away. If your energy screams “I need this deal,” they’ll smell it. Desperation is the world’s worst negotiating coach.
How to Actually Float the Idea
Eventually you have to say the words. Keep it simple and unthreatening.
Something like: “I’ve been thinking about how our two teams could be stronger together. Would you ever entertain a conversation about what that might look like?”
Notice what I didn’t say. No numbers. No timeline. No “we’re acquiring you.” Just an open door. If they say no, you smile and say “totally fair, let’s grab lunch anyway.” And mean it. Half my best deals started with a polite no.
One more thing. Control the room physically. Neutral ground. No lawyers present. A conference room in a hotel lobby works fine. Nothing says “war” like a folder labeled “CONFIDENTIAL” sliding across the table before the coffee arrives.
Protect the Relationship at Every Step
A few rules I live by now:
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Sign an NDA early but keep it mutual. Fairness signals good faith.
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Never leak the conversation. Not to your team, not to your spouse, not to the guy at the gym. Word travels at the speed of gossip.
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Assume the answer is no until it’s a signed yes. Keeps you humble and keeps them comfortable.
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Have a story ready for employees and customers. If word does get out, you want a calm narrative, not a scramble.
The biggest mistake people make is treating an acquisition conversation like a conquest. It’s not. It’s a courtship. You’re asking someone to hand you something they built with their own hands. Respect that, and you’ll be shocked how many doors stay open.
Look, some of these conversations will go nowhere. That’s fine. Plant the seed anyway. Six months, two years, five years. The best deals I’ve ever done started as a casual cup of coffee with zero pressure and a lot of listening.
Go build something. And be nice on the way up. The same people are on the way down.
