EPISODE · Jan 16, 2026 · 54 MIN
He bought two $5M+ companies in 2 years (completely off market and with no investors)
from The SMB Deal Hunter Podcast · host Helen Guo
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 readyHere'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_______________________________👉 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
What this episode covers
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 readyHere'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_______________________________👉 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
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He bought two $5M+ companies in 2 years (completely off market and with no investors)
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