Why 99% of business buyers get hung up on (it's not what you think)

TLDR: The biggest mistake when first contacting business owners is coming on too strong with "Are you interested in selling?" which immediately puts them on the defensive. Instead, position yourself as an "investor" rather than a "buyer," focus on building rapport by asking about their journey and future plans, and avoid requesting financials too early. The key is creating space for conversation rather than pushing for immediate decisions, because the best deals happen when sellers feel understood and aligned with your vision, not pressured into a transaction.

Ever felt your heart skip a beat when calling a business owner? You're not alone.

The Moment That Makes or Breaks Everything

One of the most quietly stressful moments in the entire business acquisition process is also one of the most overlooked: the very first conversation with a business owner.

It's not flashy. It's not about deal structure or financing models. It's about what comes out of your mouth when someone picks up the phone or replies to your message.

Most people botch it. They come in too aggressive, too scripted, too much "buyer energy." It’s like when a sale person has commission breath, you KNOW they want the sale and it ruins any chance of getting it.

The Trust-Killing Mistake Everyone Makes

The typical mistake sounds like this:

OUCH. That question lands like a punch. You're asking them to make a major life decision in the first thirty seconds of knowing you.

Even if they ARE thinking about selling, now they feel like they have to defend something: their ego, their valuation, their future. Walls go up, and you're on the back foot before the conversation has even begun.

The Better Way: Create Space, Don't Chase Closures

Here's a better way to think about it: the first contact is not about closing. It's about creating space. You're not trying to extract a "yes" to a sale. You're trying to earn the right to keep the conversation going.

Here is the Magic Word That Changes Everything. Most buyers don't realize that the title they give themselves changes how the seller hears everything that follows:

"I'm a buyer" sounds transactional, like you're hunting for a deal "I'm an investor" suggests long-term thinking, invites possibility, opens doors

Try This Instead:

That one shift from buyer to investor changes the dynamic instantly.

"But I'm Not Really an Investor..." (Yes, You Are!)

A lot of people hesitate to call themselves an investor because they think they need millions in the bank or a private equity team behind them.

Not true.

Capital isn't just cash. It's also: Time Expertise Relationships Systems Insight Problem-solving ability

If you bring ANY of those to the table (and you should), you're bringing value. That's capital.

The Second Trap: The Premature Financial Ask

Once you've opened the door and they're willing to talk, here's another trap first-time buyers fall into: asking for financials too early.

I get it, you want to see numbers. But remember: to a seller, those documents are personal. They don't know you. Asking for a P&L right away feels invasive.

The Smooth Alternative:

This lowers the temperature and positions you as a collaborator, not an interrogator.

The Secret Weapon: Genuine Curiosity

Before you ever get to numbers, here's the move most people skip: rapport.

You don't need to become best friends, but you DO need to earn their trust.

The fastest way? Be curious about their journey: How did they get started? What made them launch the business? What are they most proud of? What challenges have they overcome?

Listen not just to be polite, but because that's where the gold is. You'll learn what matters to them, how the business really runs, and their emotional connection to the company.

The Future-Pacing Question That Unlocks Everything

Here's an overlooked tactic: future pacing. Ask what they imagine life looks like after they're no longer running the business. Not pushy, just casual exploration:

Maybe they want to: Retire completely Stay involved as a consultant Keep a reduced role. Understanding this helps you reverse-engineer a deal structure that supports their goals, not just yours.

The Real Secret

The best deals aren't about terms. They're about alignment.

When a seller feels understood, when they feel like you actually "get" what they built and where they're trying to go, everything else becomes negotiable. The deal starts to write itself.

Your Next Move

The next time you get nervous about reaching out to a business owner, remember this: you're not selling them anything. You're inviting them into a conversation about possibilities.

When you lead with clarity, empathy, and a solid strategy, they're far more likely to say yes to that second call.

That's when the real dealmaking begins.

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. 

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