In this week’s episode, we're diving into the world of online business acquisitions with Jacky Chou.

He's built a portfolio of 50+ online businesses over the last 10 years. And today, he runs ~20 revenue-generating assets doing around $200K/month.

And he shares all of it publicly online…

But here's what makes this episode fascinating: Jackie doesn't sugarcoat the risks and takes us through countless war stories.

He bought a towing directory for $10K, grew it, and flipped it for $195K in 6 months.

Sounds amazing, right?

Except halfway through, he realized the people he was negotiating with on the East Coast were all connected. "I'm pretty sure they're affiliated with some sort of organized crime... they started making subtle threats."

He got out fast.

Then there's…

The $300K bundle of affiliate sites that went to zero.

The Amazon rate card that got yanked overnight with no notice.

The revenue rollercoaster from $70K to $560K back down to $200K/month.

When I asked him about the risks in the space, he said:

"If you were to look back three years ago, the sites that are still remaining today would be like 5% max. They're all dead."

Here’s a sneak peek into what we cover:

🔥 How Jackie runs diligence on online businesses in a few days (and red flags he's caught)

🔥 Why he had to let go of 60% of his team after AI hit

🔥 The "distribution engine" he plugs acquisitions into for immediate revenue

🔥 His current thesis on buying vs. building (it's flipped)

🔥 Why he keeps 30-40% of his net worth in cash and treasuries

Whether you're curious about online assets or just want to understand platform risk before it bites you, this one's a must-watch.

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🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz

This week’s episode with Bill Haig is one of the most impressive absentee owner stories we’ve featured.

Bill owns 4 gym locations in Northern Virginia….

But he’s never been inside any of them.

That’s a lot of first time business buyers’ dream. A ‘passive business’. But how did he get here?

Bill was an Army officer who bought his first gym with zero fitness experience right after his MBA.

And after spending the first few years in the business, he was able to work himself completely out of the day-to-day.

In the episode, we talk about that and…

🔥 What he learned in his first year of being involved in the business. (And some serious skeletons in the closet)

🔥 How he fixed the gym’s broken business model to one that made it possible for him to scale to 4 locations.

🔥 The "fetal moment" he went through after taking over the business, where he was doubting whether he’d made the right call.

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🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz

Your first business acquisition wipes out your life savings.

Your brother has to sell his house to cover the debt. You sell a property just to get back to zero.

Most people would never touch a business deal again.

Nathan Lenahan bought 4 more and built a $13M/year HVAC business.

His story involves 5 acquisitions, 1 catastrophic failure, and 4 wins that took him from broke to $13M/year.

Here's what makes it worth watching...

🔥 He lost everything on his first $350K acquisition of a Diesel Repair business in 2018. (The seller stole from customers, violated non-competes, and falsified the lease)

🔥 He was making so little on his first HVAC acquisition that he started a recruiting business that did $350K year one, $600K+ year two. He’s now working 3-4 hours per week on it.

🔥 He grew his HVAC business from ~ $1M to $13M in revenue in ~3.5 years.

And some of his most insightful lessons:

❓ The 5 deadly mistakes he made on his first deal

❓ His integration playbook after 4 HVAC acquisitions

❓ Why he's spent "more time on compensation plans than anything" (and how he's evolved pay structures every single year)

And unforgettable moments like...

"That was our life savings. All our money was gone…My brother had to sell his house to take care of the debt. I had to sell one of my properties as well to kind of get back to zero... The hard thing is, I would do it again."

— Nathan

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🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz

Devin Fitzgerald acquired 2 declining home healthcare businesses in the Boston area over the last few years and successfully turned them around.

He did it with some of the most creative financing we’ve seen on the show. And he’s already working on acquisition #3 (which is 4x bigger than all of his current businesses combined).

At some points his story is nearly unbelievable. Here are just a few snippets from his interview...

🔥 He bought his first two healthcare businesses making ~$5M in Revenue with only $50k down (and says he shouldn't have put down anything at all)

🔥 He was negotiating six-figure deals while delivering pizzas—literally putting bankers on hold to hand off a pepperoni pizza for a $3 tip

🔥 He bought a business declining 21.5% per year with zero healthcare experience (and turned it around in year one). Then did it again with business #2 (declining ~6% a year).

And some of his insightful lessons:

❓ Why he bought declining businesses (one falling 21.5% annually) when most buyers would run away

❓ The book that completely changed his integration strategy (hint: it's about Warren Buffett and John Malone)

❓ How he's differentiating in healthcare where rates are often capped and everyone competes on the same playing field

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👉 Subscribe to the SMB Deal Hunter Newsletter — free weekly deals & insights: https://join.smbdealhunter.xyz

🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz

💼 Connect with me on LinkedIn: https://www.linkedin.com/in/helen-guo-06674523/

I’m very excited to share this week’s interview with Walker Yarbrough.

He started off with long hours in Investment Banking until he looked up at his bosses and he realized he didn’t want their job (at all).

"Even once they'd climbed the ladder, they still just didn't have a lot of control of their own time…They were doing great by a lot of standards, but in the office super late and working on weekends and traveling all the time. It was just a future I didn't see for myself."

• Walker

So, Walker did what a lot of us do who want to get into ‘business’. They do literally everything under the sun, hoping something will work:

• $35,000 on an Amazon automation store. Started great—days with $1,000+ in sales selling Calvin Klein cologne. Then Amazon banned the store. Money gone.
• Print-on-demand t-shirts. His girlfriend had a successful Etsy shop, so why not? Too competitive. Went nowhere.
• Options trading. Sometimes worked. Mostly stressful. Never consistent.
• Sports betting analytics site. Got CLOSE. Almost signed the deal. Then Walker realized: "If something breaks, I don't think I'm gonna be able to fix it."

Then, he decided to simplify and buy a business he could understand.

A vending machine company with 7 locations in Atlanta. Fully owner-operated by a 75 year old who wanted to retire.

But here’s where things get interesting:
💡 Walker had to beat out an experienced vending machine company competing for the same deal.
💡 The deal got held up for 2 MONTHS over a $200 bill.
💡 And when it DID close, Walker made a classic first-timers mistake. He hired an operator to run the business and went off on vacation. Aiming for a ‘passive’ investment. Until the operator quit 3 months later.

The full story involves a panicked craiglist job hunt, Walker losing one of his biggest customers, and realizing that the business was practically run out of the previous owner’s car.

It’s a wild ride. And at the end, Walker not only succeeded but excelled. So much so, that he’s one of our new M&A advisors.

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👉 Subscribe to the SMB Deal Hunter Newsletter — free weekly deals & insights: https://join.smbdealhunter.xyz

🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz

I’m very excited to share this week’s interview with Raj Kankaria.

It is an absolute roller coaster involving layoffs, divorce, rappers, a quarter life crisis, and Raj buying a $1.3M / year business with 100% seller financing.

Here’s a sneak peak:

Raj was a former army vet who had gotten a job at Citi Bank as an investment banker.

He had just been laid off.

He was in the middle of a messy divorce.

And one day, he opened the door to a process server who handed him his divorce papers.

Out of curiosity, Raj asked the man how much he made for every delivery.

The answer: Over $100 per delivery

So, Raj started digging in…and 18 months later, with a lot of twists and turns along the way, Raj ended up OWNING a company that did exactly that.

But it gets crazier:

💡Raj ended up negotiating a 100% seller financed deal (after his SBA loan fell through)

💡He ended up building the biggest litigation support company in Harris County. With $1.3M in revenue. 1000+ contractor network. And a recession-proof business model.

💡 And before all that, Raj actually spent over a year working as a process server himself. (And he shares advice on why this was pivotal to his success later on)

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👉 Subscribe to the SMB Deal Hunter Newsletter — free weekly deals & insights: https://join.smbdealhunter.xyz

🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz

Join me as I interview Kofi Acheampong...

Kofi’s interview is unique because he actually went through our Pro program and bought a Home Restoration business cash-flowing $715k+ / year in a record 5 months.

But this interview goes a lot deeper into…

💡 How Kofi actually launched a software startup that got to #3 on Product Hunt - and how he walked away when his wife got pregnant and he had no health insurance.

💡 How he bought his $3.2M business with only 5% down and 8 months later, he’s already under LOI on a second deal with 67% seller financing.

💡 How he succeeded in buying the business after 6-7 other people had already tried and failed (including the current GM…who also happened to be the seller’s son-in-law)

👉 Subscribe to the SMB Deal Hunter Newsletter — free weekly deals & insights: https://join.smbdealhunter.xyz

🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz

I’m very excited to share this week’s interview with Michael Loftus.

Michael really shows you how far you can go with a simple strategy. Here are just a few snippets from his interview…

🔥 He bought his first 3 companies with no banks involved…with upwards of 50% seller financing…

🔥 He’s acquired 7 landscaping businesses over the last five to six years (and talks about what makes them so recession resistant)

🔥 He was able to take a 3 week honeymoon last year without taking a single phone call.

And some of the juiciest lessons…

⁉️ How Michael is able to retain 90% of the customers from each acquisition…

⁉️ How he has built up to 80 full-time employees and $6M in revenue

⁉️ His secret for hiring high quality employees (and how acquisitions are a big apart of it)

👉 Subscribe to the SMB Deal Hunter Newsletter — free weekly deals & insights: https://join.smbdealhunter.xyz

🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz