Book More Meetings with Business Owners

Hey oh, Happy Friday. The weekly biz-buying newsletter that’s your perfectly-timed Tic Tac for freshening up that ‘sales breath’ so you can book more meetings with business owners.

This week’s breath freshener:

1. Book More Meetings with Business Owners: 3 Things You Must Know

Book More Meetings with Business Owners: 3 Things You Must Know

Let’s be honest:

Most people cold call like they’re trying to sell a used car in Jersey. Awkward intro. Rambly pitch. The person on the other end smells the sales breath and is repulsed.

But if you’re trying to buy a small business, cold calling is still one of the best ways to get in the room—especially if the owner isn’t actively listing.

Here’s how to do it right and actually book a meeting without sounding like a robot or a PE bro.

And before you start….here’s a bonus:

Put your best Lewis & Clark hat on and be a curious explorer, not a closer—seek to learn, not desperate for a “yes.”

Detach from the outcome: when you dial in with zero pressure and all curiosity, you’ll sound confident, authentic, and way more human. That mindset shift is the foundation of these actionable tips to book more meetings with business owners.

Step 1: Nail the Open (First 20 seconds)

You’re not trying to “close.” You’re just trying to not get hung up on. Say this:

“Hey [Name], my name’s [Your Name], we’ve never spoken, but I came across your business and wanted to ask a quick question. Is now a bad time?”

Why it works: It’s casual.

It gives them control.

You’re not selling anything (yet). You’re just a curious human.

Bonus tip: Smile when you say it. It comes through in your voice. Weird but true.

Step 2: Ask Something That Gets Them Talking

Now that you’ve earned the right to exist, go here:

“Are you still the one running the day-to-day at [Business Name]?” “A lot of owners I talk to lately have been thinking about what comes next—retirement, succession, or just de-risking a bit. Have you ever explored what it might look like to transition the business someday—or is that way off your radar?”

Then shut up. Like, really shut up.

Why it works: You’re not asking “Wanna sell?” You’re asking “Ever thought about it?” This is the difference between being ignored and getting real answers.

Step 3: Book the Meeting Without Being Pushy

If they bite (even a little), say:

“Totally get it—it’s not about rushing anything. I’d love to set up a quick call to swap notes and share how other owners are thinking about this. Even if it’s not a fit, I think you’ll walk away with some good insight. Would sometime next week work for a 20-minute chat?”

Why it works: Low commitment

You’re offering value, not a sales pitch

It sounds like something they might want, not something you need

Then send a calendar invite with a tight subject line and a couple bullet points on what you’ll cover (valuation trends, succession options, etc.). Keep it pro, not spammy.

TL;DR: The Cold Call Formula

Mini invite → “Can I ask you a quick question?”

Qualify → “Are you still the one running the show?”

Engage → “Ever thought about transitioning someday?”

Book it → “20 min next week to swap notes?”

That’s it. Casual. Clear. Human. Now get out there and dial.

P.S. Here is cold call script you can steal to book more meetings.

Want the full call script, objection responses, and show-up strategy?
Reply “OWNER” and I’ll shoot it over.