Michael and his partner, Ashish, only buy businesses that are $5M+ in EBITDA (way above the SBA limit).

He aims to buy a new one every year.

And the last two he bought, were completely off market.

To that point, 90% of his sourcing is off-market.

No BizBuySell. No broker bidding wars. Just relationships built over time at conferences, through colleagues, and by doing a lot of outreach.

But we’ll get to that. First, a little bit of background…

Michael is an Air Force veteran and former private equity analyst.

He and his partner run Skyline Partnership, a holding company with two acquisitions: a cybersecurity software developer and an HVAC company doing $13-15M in revenue.

They’re aiming to build a holding company that they can pass off to their children. One that’s built to last. And they’re just getting started.

And in today’s interview, we dive into a few topics:

🔥 The off-market sourcing playbook that's landed both of their deals (no brokers involved)

🔥 How many companies you actually have to reach to close one deal a year at their scale (the number might surprise you)

🔥 Why they send direct mail to business owners in target geographies (and what actually gets through)

🔥 The CRM habit that keeps cold leads alive until they're ready

Here's his must-watch breakdown...

He also shared some tactical advice I don't hear often:

❓ Why he thinks most searchers are "too agreeable" with brokers (and how to push back)

❓ What to do when a seller says "not interested" (hint: don't delete them)

❓ The industries he's most bullish on right now (they’re not the ones you usually hear)

And moments like this...

— Michael
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You've probably done this…

You found a listing you liked. You sent the NDA. Maybe you even fired off a quick note about your background and the things you’d like to learn.

Then... nothing.

A week later, the deal’s under LOI. No call back, no response to your request.

Here's what you didn't see:

That listing probably got 65 inquiries in the first few days. Of those, 10 of them came in prepared.

The rest never got a serious look. Not because they weren't qualified but because they didn’t understand how to cut through the noise and get the broker’s attention.

This week I sat down with a broker who's going to show you exactly what happens on the other side of a business acquisition.

Alejandra has been doing this for years. She started in Miami, sold her first business in 4 months, got recruited into Deloitte's M&A practice, and recently joined our team as an M&A advisor inside the Pro program.

She's seen hundreds of deals and dealt with countless buyers. Most of them make the same mistakes.

Here’s are some of the highlights from the deep dive:

🔥 Alejandra goes through what the first 48 hours look like from the broker’s perspective when a hot listing goes up

🔥 She shares the three documents she needs before she'll present you to a seller. (Most buyers only send one)

🔥 She shares loads of war stories on deals that went bad and what you can learn form them

🔥 And she pulls back the curtain on why brokers often don’t return calls, why ‘cash offers only’ listings are usually not serious, and how you can stand out from the crowd when competing for a popular business.

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👉 Sign Up For Free to the SMB Deal Hunter Newsletter: https://join.smbdealhunter.xyz

🤝 Work With Me to Help You Buy a Business: https://pro.smbdealhunter.xyz

This week's episode starts with a horror story.

Joe and Colin from Circle City Capital Group bought their first business together in 2018.

After meeting on Craigslist (yes, seriously)

They bought an overnight delivery route business specializing in auto parts. They started with 5 routes and put in less than $100k to acquire the business.

But on their first night as owners…two drivers didn't show up.

So Joe and Colin got in the trucks themselves. And for the next few months, that became the routine. Driving 400 miles a night. Colin doing it while still working a full-time job.

The business ran their lives.

So why did they go on to buy 14 more?

Because somewhere in that chaos, they figured out how to work on the business vs in it. Hiring an operator. Getting out of the day-to-day. And beginning to scale.

Today they've done 15 acquisitions across consumer brands, e-commerce, and financial services.

Every business in their current portfolio has a GM or CEO in place. And they're closing three more deals in Q1 of 2026.

Here's are some highlights worth watching...

🔥 The 11:30pm Denny's interviews that helped them find their first real operator

🔥 How they flipped that nightmare first business to a PE firm in 18 months

🔥 The "two filters" they now run every deal through before buying

🔥 A story involving train tracks that explains why they tell people to work in a small business before buying one