Join me as I interview serial acquisition entrepreneur Ujwal Velagapudi.

Ujwal left his corporate career working in supply chain management to buy small businesses.

His experience spans a variety of industries, from buying a local sports bar and gym (among others) to now focusing on amusement vending machines.
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Join me as I interview Gretchen Roberts, an entrepreneur who acquired Red Bike Advisors, a remote-first accounting, tax, and advisory firm based in Wilmington, NC.

What makes Gretchen’s story unique? She’s not a CPA and doesn’t come from an accounting background.

Before buying the firm, she worked in marketing at a major public tech company. Now, she owns and operates a professional services business — without ever having prepared a tax return.
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This week, I sat down with Savannah Rush, Managing Partner at Funded Ventures.

Savannah went from McKinsey consultant to owner-operator of Midway Electric in Columbia, Missouri.

She and her partner Brian Wolf (who I interviewed previously) have closed two home services deals and are laser focused on building a long-term holding company.

She's not aiming to flip or exit. Her goal is to build a compounding machine.

Here are some of the highlights from the deep dive:

🔥 How she went from "ETA skeptic" to running an electrical company in a market where she doesn't exactly look like the typical president

🔥 The state of the business when they bought it (everything was on paper, hourly rates were 40% below market, and the owners were barely holding on)

🔥 How they turned it around in months, including the pricing conversation with the team that actually got buy-in

🔥 Why they're willing to go "super, super small" on acquisitions when everyone else says to go bigger

Here's her must-watch breakdown...

She also shared some things I don't hear enough people admit out loud:

❓ Why she was nervous about stepping into the role

❓ The one thing her McKinsey background didn't prepare her for

❓ Why "being involved in the community" has become one of their biggest unlocks for finding proprietary deals

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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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

What would you pay for a failing street sweeping business that was:

Making $200k / Year in revenue (down from $1.1M)

Barely breaking even on profit

With trucks breaking down constantly

Underpaid drivers (constant turnover)

Brandon Dixon paid $0 down.

100% seller financed with a 60-month term.

He jumped head first into the turnaround with no experience and turned it into a $96K/month business in 14 months.

We dove into a few big questions throughout the interview...

❓️How did a professional baseball player buy a failing street sweeping company for $0 down and 5x revenue in 14 months?

❓️Why did Brandon say he'll "never buy this small again" - and what would he do differently?

❓️How is Brandon running a 35-40% margin business from 7 hours away with an offshore hire managing day-to-day operations?

❓️What happened when 3 trucks broke down on his first day as a full-time operator - and what did it teach him about equipment businesses?

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Join me as I interview Brian Wolfe, a lawyer, small business investor, and PE and search fund professor.

Brian founded Funded Ventures, which partners with builders to buy and build small businesses.

Their first platform which was formed to acquire SaaS companies in the martech space successfully exited to Alpine Investors after 3 completed acquisitions in 20 months.
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