If you run a marketplace or platform, let me give it to you straight: you’re going to get sued.

It might not be today. It might not even be this year. But if you scale—and especially if you succeed—it’s only a matter of time. That’s not fear-mongering. It’s the reality of operating in the high-stakes, highly visible world of digital platforms.

If you run a platform that hosts user-generated content, May 19, 2026, is a date you should have circled on your calendar. That's the compliance deadline for the Take It Down Act (TIDA) - and the FTC just made it very clear they're watching.

Online moderation of social media (Facebook, Instagram, TikTok) and gaming platforms (Minecraft, Roblox) is just one area where AI should be a natural fit on the surface. HR is another. That being said, it’s not a complete replacement for manual, human labor. There are areas, including labeling, oversight, and QA, where humans and AI can work together to create more effective, efficient ways for businesses to operate better than ever before.

You might think you know what kind of business you’re running—but if regulators, courts, or the IRS disagree, you’re in trouble.

Let me guess—you didn’t start a marketplace because you love tax law. I didn’t either. But here’s the reality: if your platform facilitates transactions, tax compliance isn’t optional—it’s inevitable.

In Chapter 8 of Bulletproof Your Marketplace, I pull back the curtain on one of the trickiest, most misunderstood parts of scaling a platform: taxes. It’s not glamorous. It’s not fun. But if you ignore it, your business could end up in serious legal and financial jeopardy.