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...

"We bought an HVAC company from a private equity firm. The old GM showed up, gave us a tour, handed us the keys, and said 'good luck.' No transition. No documentation. Nothing. The first two weeks is the first time in my life I've actually lost hair."

— Michael
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Episode 517: Sex, Lie, and Videotape

TRUE ANON TRUTH FEED

Intro

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