Imposters Run The World

This week a founder in our community booked time with me during my weekly office hours and asked how to get over imposter syndrome.

This is something we all feel at one point or another. It can be hard to shake.

But almost all advice I hear about what to do about it is wrong.

So I told this founder the truth.

And now I’m going to tell you exactly what I told them.

This one’s for the underdogs 👇

Imposters Run the World

I’m An Imposter

In 2016 I went from driving for Uber to make extra money while running an agency, to working on Uber’s fast growing Uber Eats product.

I was 2 years removed from graduating from the University of Miami — a far cry from Stanford or the Ivy League — and was struggling to find my footing in the real world.

I’d spent those 2 years first working as a (bad) software engineer at a small startup in my hometown of Philadelphia and later in trying (and only sometimes succeeding) to get my own agency off the ground.

When I needed extra cash to pay rent, I drove for rideshare services.

I’ll tell the story of how I got the Uber job through cold outreach another time but you can imagine the culture shock when I started.

Suddenly I, a severely underachieving C-level student, was surrounded by lifelong high-achievers.

My new teammates had come from private equity, elite consulting firms, or had profitable side projects.

They were welcoming and friendly but all were sharp and bound together by a shared ambitiousness and high-bar. My first manager, in particular, did not tolerate mediocrity.

Unlike every school or job I’d ever had this was not a place that catered to the lowest common denominator.

It was exhilarating. I instantly felt like I’d finally found my people.

But I doubted they felt the same about me.

The same thing happened when I founded my first startup:

• I went from being laid off to being interviewed by The New York Times from a McDonald’s parking lot in Tulum the next quarter.

• Andrew Chen from a16z (our eventual lead investor) was one of our first 100 Twitter follower.

• The people who wanted to be our members were far more accomplished than I was.

What would happen if I couldn’t keep them interested?

The Bad Advice You Always Hear

If you ask ChatGPT what to do about imposter syndrome as a startup founder, here’s what it says. One of its recommendations is “seek professional help”….

Human-written articles tend to say similar things. You should rely on the validation of others, find and lean on mentors, celebrate small wins you have, etc.

Basically if you have imposter syndrome the common advice can be summed up by saying that you should manage it like some sort of medical condition you’re stuck dealing with.

All of this is bad advice for someone who is or wants to become a startup founder — a role that requires you to move mountains to make even an inch of progress, with long and often lonely hours with nothing to fall back on other than your own will.

The typical advice to deal with imposter syndrome is passive. Founders can’t be.

You’ll never be free of it if you treat it that way. It’ll always be hanging around, waiting for you to forget to say your affirmations one morning.

The Truth and What to Do About It

It turns out imposters run the world.

So why do some imposters rise to the top while others mourn their fate and handicap themselves?

How did I turn my initial feelings into a successful tenure at Uber where I repeatedly increased my responsibilities, and later built a startup that did millions in revenue and raised millions more from some of the best investors in the world?

I turned imposter syndrome into a superpower.

Feeling uncertain of whether I belonged meant I had no pressure on me. If I failed, it was ok — I was likely to (maybe even expected to).

For any sports fans reading this, it meant I was Muhammad Ali (the still-upstart boxer) and everyone else was Sonny Liston (the veteran).

I allowed myself to be shameless.

I allowed myself to be cringe when I needed to.

The pressure was off me and, instead, on the people with more credentialed backgrounds.

They were the ones who had to maintain the weight of those track records.

I had no idea whether any of them actually felt more pressure than I did or not and it didn’t matter — that wasn’t the point.

Framing it that way dissolved the feeling entirely. I didn’t have to succeed, and ironically this made me more likely to.

More practically, this meant nothing was outside my reach as a founder.

I felt more confident cold emailing and pitching top investors, convincing former Y Combinator-backed founders to join my team as employees instead, or leaning into sales and cringe content to grow faster.

It sounds cliché but the worst that could happen is that they’d say no. Then I’d try to understand why and try again. That’s it.

Understanding this has become a compounding advantage in my career.

If you’re frequently able to be even just 1% more sure of yourself as a founder than you were the day before it will become one for you as well.

So what should you do if you feel like an imposter?

1. Don’t manage it like a chronic condition

2. Realize everyone fails and expects you to too

3. Embrace being an underdog

That third point is your superpower.

💡 How I Can Help