So Much to Gain, Everything to Lose

From the Introduction to Bulletproof Your Marketplace

If you’re reading this, chances are you’re either building a marketplace or already operating one. First of all—congrats. That means you’re part of a $3.6 trillion global economy that’s reshaping how we live, work, and connect. But while there’s enormous opportunity in building a marketplace or digital platform, there’s also a ticking clock on when—not if—something will go sideways.

I wrote Bulletproof Your Marketplace because I’ve seen too many founders focus solely on product, growth, and fundraising—without considering the unnecessary risk, exposure, and liability that can derail everything they’ve worked for. Trust me, I’ve been there. And I’ve spent the last two decades helping marketplaces avoid that fate.

In the early days of building and scaling Sittercity, I was juggling everything from user safety to patent trolls. I quickly realized that managing legal and risk wasn’t just about “keeping the lights on”—it was a competitive advantage. It was also surprisingly neglected by investors and founders alike. Most people were flying blind. That’s when I started laying down the frameworks and strategies that would become the backbone of this book.

Let me be clear: this book isn’t about how to grow your user base or raise a Series B. There are plenty of accelerators and consultants who can help with that. This book—and this blog series—is about something far more existential: how to protect the business you’ve worked so hard to build.

In this chapter, I share how I transitioned from being an IP lawyer to an operator, to someone obsessed with platform risk, trust and safety, and legal strategy. I also talk about the early days of Marketplace Risk, which started as a small working group and has since become the largest community of marketplace leaders focused on these very challenges.

One thing I emphasize to every founder I work with: if you think legal issues won’t happen to you, you’re wrong. At scale, bad things will happen. Whether it’s a safety incident between users, a data breach, or a headline-making lawsuit—it’s not a matter of if, but when. My job is to make sure that when that moment comes, you’re prepared. Because if you’re not, it can be game over.

This book walks through the top issues I’ve helped hundreds of platforms navigate—things like CDA Section 230, user terms of service, data privacy, trust and safety protocols, insurance, taxation, and incident response. These aren’t “nice-to-haves.” They’re the difference between running a high-growth platform that can scale safely, and one that ends up in a courtroom—or worse, in the headlines for all the wrong reasons.

So, whether you’re just launching or leading a unicorn, this book is your toolkit. I’ve done my best to keep the legal concepts approachable and actionable—this isn’t a law school textbook. My goal is to give you just enough knowledge to be dangerous in the best way: informed, proactive, and protected.

Up next, we’re diving into Chapter 1: The Marketplace—Past, Present, and Future. We’ll zoom out for a minute and explore why marketplaces have stood the test of time, how today’s platforms are rooted in ancient commerce, and what that means for your business today.

Until then, remember: growth is great, but resilience is what keeps you in the game.

Want to dig deeper into marketplace risk, trust & safety, and legal strategy?

Visit www.jeremygottschalk.com to learn more about me, the book, and upcoming events.