He's acquired 50+ online businesses making $200k+ / month. (Here's how he does it) | Jacky Chou episode artwork

EPISODE · Nov 28, 2025 · 40 MIN

He's acquired 50+ online businesses making $200k+ / month. (Here's how he does it) | Jacky Chou

from The SMB Deal Hunter Podcast · host Helen Guo

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

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

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He's acquired 50+ online businesses making $200k+ / month. (Here's how he does it) | Jacky Chou

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This episode was published on November 28, 2025.

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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...

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