🎙️The brutal truth about online business acquisitions (from someone who's done 50+ of them) | Jacky Chou

Hello SMB Deal Hunters!

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’s doing around $200K/month with all of them combined.

And he shares all of it publicly online…

But here's what makes this episode even more fascinating: Only 20 of Jackie’s 50+ acquisitions make up that $200k / month. The rest have ‘died’.

We dive in to the risks that come with his style of business buying.

For example, 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.

👉 Dive into the wonderful (and sometimes very risky) world of online business acquisitions with Jacky…

And for our audio-only listeners, jump in and listen on Spotify or Apple Podcasts!

Alumni Spotlight

For those who missed it, we also did an SMB Deal Hunter Pro case study breaking down Mary’s acquisition of a $1M medical billing company that we helped her find and acquire completely off-market.

She did all of that within 10 months of joining the program.

Before jumping into the world of business buying, Mary spent 12+ years in tech as a UX Researcher at major companies like Pinterest and LinkedIn.

She started off where a lot of you are right now.

In the case study, we dive into…

✅ The 3 due diligence hurdles we helped her overcome (including a silent partner she didn’t know about)

✅ The complicated deal structure that led to her keeping the seller on for 10% of the business (with a buyout clause)

✅ The reality of life in the first 90 days into an acquisition (and how she managed it)

And here’s what she had to say when we asked her about her experience:

So, if you want me and my team to work with you to find, finance, and acquire a million-dollar cash-flowing business in the next 6-12 months, you might be interested in the Pro program.

👉️ Learn more and book a call

COMMUNITY PERKS

• Ready to buy and operate a $1M+ business? Get expert help at every step.

• Want to invest passively in SMB acquisitions? Get access to investment opportunities.

• Get a personal introduction to my preferred SBA 7(a) lender, non-SBA lenders, Quality of Earnings providers, or legal counsel

• Raising capital for your deal? I’ll connect you with investors from the SMB Deal Hunter Community.

• Interested in selling your business? I’ll help you connect with buyers from the SMB Deal Hunter Community.

THAT’S A WRAP

Want me to interview you for my podcast? Hit reply.

See you next week with some new deals!

-Helen Guo
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Disclaimer

This publication is a newsletter only and the information provided herein is the opinion of our editors and writers only. Any transaction or opportunity of any kind is provided for information only; SMB Deal Hunter does not verify nor confirm information. SMB Deal Hunter is not making any offer to readers to participate in any transaction or opportunity described herein.