Look The Part

Excerpt #5 From My Upcoming Book

One of the biggest disconnects in the startup world is the myth that you can raise venture capital purely on the merit of your product or your passion. The hard truth? Most investors don’t just invest in products—they invest in people who feel familiar. And familiarity often comes from behaving like you’re already part of their world. In other words, if you want to raise money in tech, you can’t just be smart—you have to look the part.

Earlier today, I posted something that stirred up some controversy: a list of tools you should use if you want to blend in with insiders.

To some, it sounded shallow—like I was suggesting playing dress-up in startup drag. But what I was really getting at was this:

If you’re a founder trying to raise capital, especially from Silicon Valley, your number one job is to become familiar. That means getting inside the networks where trust flows and deals get done. Outsiders can raise money, but it’s much harder. Even if they land a seed round, the next raise becomes exponentially tougher without the right signals and relationships. Fundraising as an outsider is like swimming upstream. Doable, but brutal.

So the practical question becomes: How do you become an insider—or at least look like one long enough to get a seat at the table?

This is where behavior matters. Tools and workflows might seem cosmetic, but in tech, they’re cultural markers. They signal that you know how the game is played.

Take Superhuman. It’s not just an email client; it’s a shorthand for “I know the right tools.” If a Silicon Valley investor sees that you use Superhuman, it communicates a few things instantly: you’re probably plugged into certain tech circles and you’ve opted into the same workflow as many top-tier founders. That’s familiarity.

Or consider what happens when a VC asks how your company is structured. If you respond with, “We incorporated via Stripe Atlas,” that tells them you’ve done this before—or at least done your homework. You understand how startups are typically formed. You’re not asking them to educate you on the basics.

This stuff may sound superficial. But these are the cues that insiders look for before deciding to lean in. Most founders never make it past that first filter—not because their product is bad, but because they don’t speak the language. They’re missing the shared reference points that create trust.

Here’s a rough analogy: Imagine I cold email Mark Cuban and somehow get a meeting. That’s great in theory. But if I’ve never seen a single episode of Shark Tank, have no idea he owns the Dallas Mavericks, and don’t understand the industries he invests in—what are we really going to talk about? I wouldn’t know how to speak his language or make the most of the conversation. That’s how most outsider-to-insider outreach comes off. It’s not that you’re unworthy of time—it’s that you haven’t shown you’re ready to make it worth their time.

So if you want to raise money—really raise money—you need to do three things:

1. Cloak yourself in insider behaviors.

2. Mirror the tools and workflows of the people you’re trying to reach.

3. Use those shared reference points to create trust.

If you use Mercury, Brex, Superhuman, Notion, and set up your company with Stripe Atlas, you’re starting to play the part. It doesn’t make you fake—it makes you strategic. And done right, it becomes hard to tell whether you’re an outsider at all.

And that’s the point.

Because if a VC or founder can’t tell whether you’re in or out, they’re more likely to say, “Sure, I’ll take the meeting.” And once you’re in the room, anything can happen.

This isn’t about selling out or pretending to be someone you’re not. It’s about understanding how credibility is constructed in the startup world—and learning how to build it when you weren’t handed it at birth or by location.

You don’t need to be in SF. But you do need to act like someone who belongs there.