• Roland’s Riff
  • Posts
  • Why Your Outreach Is Getting Ghosted (and How to Fix It)

Why Your Outreach Is Getting Ghosted (and How to Fix It)

Stop Sounding Like A Robot. Start Getting Replies.

TLDR: Most buyers blow the deal before it starts by sounding like a spreadsheet in a suit. Sellers aren’t impressed by buzzwords or consolidation jargon, they’re exhausted operators who want to be heard. If you want a real shot at the deal, drop the Wall Street tone and sound like someone who actually gets it.

Why Most Buyers Sound Like Wall Street and How Not To

You’re finally ready to make a move on a business. You’ve identified the opportunity, you’re excited to reach out and then you send an email that sounds like it was written by a private equity robot.

“We’re aggregating vertical market assets to create synergies and expand market share in the X sector.” Cue the delete button.

That kind of language might impress your finance professor. But to the seller? It’s noise. It signals that you don’t get it.

Because here’s the reality most buyers miss: You’re not pitching VCs. You’re talking to business owners, real people, often overwhelmed, often burnt out, often too busy to read past the first sentence unless you give them a reason to care.

They’re not analyzing synergy potential. They’re figuring out how to make payroll next Friday and why half their team is ghosting Slack.

So when you show up talking like a corporate acquisition machine, they instantly assume you’re going to lowball, complicate the process, or just waste their time.

That’s why I do it differently. I don’t lead with numbers. I don’t lead with jargon. I lead with curiosity.

A simple message like: “Hey, I’ve worked with businesses like yours and I’d love to hear your story. No pressure, just curious what you’ve built and where you see it going.”

That opens doors. Because it doesn’t sound like a pitch. It sounds like a peer.

That one shift, peer, not predator, completely changes the tone of the conversation. You get real replies. You build rapport. And when the time comes to talk terms, you’re not negotiating with resistance. You’re talking with someone who feels seen.

Remember: most sellers aren’t out there hunting for suitors. They’re focused on survival. They care about what happens to their team, their customers, their reputation.

So when a buyer comes along who actually listens, who sounds human, that stands out like crazy.

Here’s the truth, the first message isn’t about the deal. It’s about connection.

You can talk about earnouts and structure later. But if you start with “synergistic expansion of fragmented verticals,” don’t be surprised when your email lands in the trash.

Want more responses? Ditch the pitch deck. Start the conversation like this:

  • What inspired you to start the business?

  • What’s been your proudest moment building it?

  • What’s something you wish more people understood about running it?

Those are the kinds of questions that make people want to talk. And if you want to buy their business, you need to understand more than the balance sheet. You need to understand them. This isn’t a takeover. It’s a transition. And it starts with trust.

So stop sounding like Wall Street. Start sounding like someone worth talking to.

Now tell me honestly, does anyone actually fall for those “synergistic partnership” emails? Or are we all just pretending they work?

P.S. If you're ready to stop watching from the sidelines and start owning the field, let’s take the next step together. Click here to see exactly how I buy my businesses. 

Thinking About Exiting Your Business?
You’ve built something incredible—now it’s time to make sure you get the most from your exit. We’ve helped countless entrepreneurs maximize their business sales, ensuring they walk away with more than just a deal—they walk away with the best deal possible.

Want to see what’s possible for you? Schedule a complimentary call (click here) today to see how I can help you get the most out of your exit.

Whats Going On

Recently On The Business Lunch Podcast: In this episode, get into the art of creating effective offers and adapting sales strategies for different business models. From navigating the challenges happening because of rising ad costs to understanding the nuances of sales motions, we share valuable insights and practical tips. Whether you're selling high-ticket items or aiming to optimize online conversions, this episode is packed with advice to help you convert successfully..— Listen on Apple Podcasts I Spotify 

Want to learn my full process?: Join me where I break down my entire, exact system, step-by-step, how deals are sourced, structured, funded, and closed. No theory, just proven strategy. Watch here. 

The Riff

The $4M deal was dead. We were stuck in a standoff for 3 weeks, nothing moved. Then I asked one question that flipped the entire negotiation on its head.

It wasn’t about the money. It never is. What happened next turned a broken deal into something bigger….for both sides. I break it down in this short video: 👇 Watch below or click here.

P.S. Follow me on Instagram for my latest