What They Said Vs. What They Meant: Decoding Owner Responses

Last quarter, we sent thousands of outreach emails to business owners on behalf of searchers looking to acquire companies.

Some got ignored, some got deleted, and some got terse responses telling us to never contact them again.

But then there were the replies that mattered - the ones from owners who were skeptical but curious, burned but willing to engage, or cautiously open to the right conversation with the right person.

And when you read them carefully, they reveal something most people miss: When you read them carefully, patterns emerge. Owners aren't just replying - they're signaling where they are emotionally, what they need to feel comfortable, and what will make them disengage.

An owner's first response isn't about whether they'll sell. It's about whether they trust you enough to keep talking.

Here's what we've heard from owners who replied, and what they were really saying:

The Skeptics

What they said: "I thought you might be a phisher but looked for you on LinkedIn to see that you are indeed a real human."What they meant: Most emails I get are garbage. Yours made me curious enough to verify you exist. Don't waste that.

What they said: "Thanks for reaching out. It's tough to determine who's real and who's not these days."

What they meant: I'm drowning in generic spam. Show me you're different.

These owners replied because something in your message stood out. But they're still skeptical. Your follow-up needs to reinforce that you're not another mass-email searcher. Reference something specific about their business. Show you did homework. Make it clear this isn't a template.

The Burned Ones Who Need Proof

What they said: "We can have one meeting then a nonrefundable deposit will be expected to advance any discussions."

What they meant: I've wasted months with tire-kickers. If you want my time, you need to prove you're serious.

What they said: "We've had conversations with several 'interested' private equity groups and learned that most didn't know or care about our technology, our 20-year reputation, our data, or the value we've created; they only care almost entirely about recurring revenue. That was disappointing, but it clarified our path."

What they meant: I built something I'm proud of, and watching strangers reduce it to an EBITDA multiple broke my heart. Don't be like them.

These responses are defensive because the owner has been through bad processes before. They've spent time with buyers who didn't respect the business, didn't follow through, or were clearly just shopping around. Your job isn't to get offended by the friction - it's to acknowledge it and demonstrate you're different through actions, not assurances.

The Cautiously Open Who Want You To Earn It

What they said: "I've received several similar inquiries and most of the people don't follow up."

What they meant: I responded to you. Now show me you're not like everyone else who disappeared after one email.

What they said: "Thanks for your note and I appreciate your soft approach. I really can't say that the company is for sale, but I think it might be a good idea for us to meet."

What they meant: I'm not ready to sell today, but I'm open to the right opportunity with the right person. Don't rush me.

These owners are the most interesting. They're not actively selling, but they're not opposed to it either. They're in the consideration phase - thinking about succession, exit timing, what comes next. If you push too hard or move too fast, they'll pull back. If you match their pace and build rapport, these often become the cleanest deals because you're working on their timeline instead of competing in a rushed process.

The Green Lights

What they said: "Thanks for reaching out and for your kind words."

What they meant: You noticed something specific about me or my business. That felt good.

What they said: "It is a pleasure meeting you. Your bio is interesting."

What they meant: I looked you up. I see why you're doing this. I want to know more.

What they said: "Most of these types of emails immediately get trashed that come through my inbox, but I LOVE a family of entrepreneurs."

What they meant: You told me something real about yourself, and it resonated. Keep being human.

What they said: "Ha, love your approach, which is why I'm responding..."

What they meant: You made me smile. That's rare in my inbox.

What they said: "I receive unsolicited inquiries on a regular basis, but yours struck me as particularly personal and genuine."

What they meant: You treated me like a person, not a target. 

These are the ones who are closer to ready. They appreciated something human in your outreach and they're signaling openness. But even green lights can turn red if your follow-up is bad. Stay personal, stay specific, and don't suddenly switch into corporate-speak now that you have their attention.

Why Follow-Up Wins Deals (Not Your Initial Email)

Getting replies feels like progress. It is progress. But most searchers treat the reply as validation that their outreach worked, and then they lose focus.

They send a templated "great to hear from you, here's my calendar link" response. Or they wait three days to reply because they're busy. Or they ask generic questions that make it obvious they didn't read the owner's response carefully.

Meanwhile, the owner is:

• Getting distracted by their business

• Receiving more generic acquisition emails

• Questioning whether selling is actually the right move

• Wondering if you're serious or just another browser
  

The window between reply and real conversation is where most deals die. Not because the owner wasn't interested, but because the searcher didn't capitalize on the moment.

What Good Follow-Up Looks Like

Good follow-up isn't about speed, though responsiveness matters. It's about reading the signal the owner sent and responding accordingly.

If they're skeptical, acknowledge the skepticism and give them a reason to trust you - specific knowledge about their business, a clear explanation of your background, proof you're not sending 500 identical emails.

If they're burned, don't get defensive about their friction. Show empathy. "I can imagine you've had frustrating conversations before - I'd feel the same way." Then demonstrate through specificity and respect that you're different.

If they're cautiously open, match their pace. Don't immediately push for a call. Build rapport first. Ask a thoughtful question about their business. Show you're interested in understanding, not just transacting.

If they're giving you a green light, don't waste it by going generic. Stay human. Reference what they said. Keep the tone conversational. Move things forward but don't suddenly shift into "let's talk acquisition structure" mode.

The Bottom Line

Off-market search works because it gives you access to owners before they're in formal processes. But that access is meaningless if you can't convert initial interest into real conversations.

The difference between searchers who close and searchers who waste 12 months isn't their outreach volume or their email copy. It's whether they understand that getting a reply is just the beginning, and everything that happens next determines whether they ever see an LOI.

Read the signals. Respond accordingly. Build trust before asking for anything. That's how deals actually happen.