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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👉 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