When I was running Seedscout, I met a lot of smart founders building great businesses—but many of them deeply misunderstood startup culture. That misunderstanding made their journey through tech way harder than it needed to be. Worst of all, no one was really incentivized to help them, because it’s hard to know where to even start. That’s why I’m excited to announce that I’m writing a book on this exact topic.
The goal of the book is simple: I want to be able to tell any founder in the world, “Grab a copy,” and once they’ve read it, I can trust they have the foundational context needed to navigate startups, tech, and venture capital. No more gatekeeping. No more guesswork. Just truths from the belly of the beast.
I’ll be leaking early excerpts of the book through this newsletter as I write. The first one is called Pawn of Pawns.
Everyone in tech is playing a game. There are a handful of different games to choose from, but make no mistake—everyone is playing one. One of the common denominators across all these games is the pursuit of status within the tech ecosystem.
And one of the most effective ways to build that status? Find someone early in their career—someone brilliant but undiscovered—and back them.
You mentor them. You invest. You introduce them to your network. You bring them to the parties. And as their star rises, so does yours. Their success becomes part of your résumé. One of the clearest examples of this is Keith Rabois and Delian Asparouhov. Keith took Delian under his wing—and now Delian is a force at Founders Fund, which led to Varda. Win-win.
But here’s what most people don’t tell you:
Sometimes, this dynamic isn’t about helping you—it’s about using you.
The tech world is full of status climbers constantly scouting for the “next big thing.” If you’re smart, young, and unproven, you’re a prime target. They’ll make you feel special. Give you access. Talk like they’re your new best friend. You’ll feel like you’ve arrived.
But often, they’re just betting on you like a penny stock. If you take off, they cash in—socially and financially. If not? They move on to the next bright-eyed dreamer.
And the dangerous part is: they usually won’t tell you what game they’re playing. Because if they did, it would break the illusion of genuinely wanting to help you. Sometimes, their incentives even conflict with your best interests.
Say you’ve built a great business that doesn’t need venture capital, and you aren’t actively seeking it. But along comes a VC who sees an opportunity—for them. They convince you to raise. They sell you the dream. They get their mark on your cap table and their foot in the door of your story.
And just like that, you’re on a track you may never have needed to be on.
Y Combinator is the master of this. Their pitch is: “Think bigger. Go faster. Build something people want.” But under the hood, what they’re really saying is: “We want one of you to return our fund, and we don’t care who it is. So swing for the fences. If you fail, we’ve got 349 other irons in the fire this year.” And they rarely walk founders through the true cost of that pressure.
If you’re a smart, early-stage founder and someone is making your entry into tech feel a little too easy… pause. Chances are, they’re playing the game. And you are part of the play. Does that mean you shouldn’t take their help? Not necessarily.
Sometimes, self-serving behavior aligns with your own goals. Sometimes, that mentor, investor, or guide will actually change your life for the better. But just know—everyone has incentives. And sometimes, they have no incentive to share those with you.
So pay attention. Ask questions. Stay independent-minded. Because in this game, understanding the rules is the first step toward not being played.
Well said. All too often, people in venture capital are treated as merely means as opposed to ends. Choose your company, confidants, and collaborators wisely.