Every time I’m about to step on stage, talk to someone famous, or pitch a crazy successful, twice-exited founder, the same thought pops up: Who the hell am I?

But, that’s the Philly in me. 

We’re perennial underdogs. There’s no real tech scene, no ecosystem — nobody from my childhood writing code, just a bunch of people who think “Series A” is a fancy section at the Linc.

So when I’m in a room full of “founders,” there’s still a very loud South Philly voice in my head that’s like, "What are you doing, you hoodlum — you do not belong here”.  

I felt that way back in October 2020.

It was my first all-hands as CEO of The Hustle.

Thirty faces on Zoom, waiting for me to prove I belonged.

You could feel the quiet skepticism: He didn’t build this — so why him?

And truthfully, I’m sure I asked myself the same question.

So I did the only thing I knew how to do — work.

No big speech, no fake bravado, not trying to be somebody, or some thing. 

Just: here’s who I am, here’s what I know, here’s what I don’t know.

Then I went straight into the real problems — busted payment stack, low morale, comp issues. 

And a funny thing happens when you just start fixing:

Within a few weeks, nobody gave a sh*t who I was.

Because I was useful.

That’s the cure for feeling like an imposter; it’s not confidence you need, but contribution.

Imposter thoughts are momentary. They show up, they whisper “you sure about this?”, and push you to prepare harder.

Imposter syndrome is different. Syndrome is when the doubt moves in, sets up shop inside your head, and starts narrating your entire story.

Everyone gets imposter thoughts. It’s a natural (and useful) part of the job.

Doubts make you double-check your work, listen harder, prepare more, keep chasing the truth.

But when the question “Is this good enough?” turns into “Am I good enough?”, or, even worse, “Is that other person better?”--  that’s when doubt stops being fuel and becomes friction instead.

In my experience, confidence isn’t some fixed part of who you are, but rather something you build through evidence over time. 

Sure, I’ve always had a base level of self-belief (thanks, Ma), but the real confidence came from proof; from doing the work, seeing good results, and then stacking those little wins.

That’s why I tell anyone with imposter syndrome, just focus on your craft, not your story or your perceived credibility.

If you focus on credibility, you’ll always feel behind, less then, ill-prepared. 

When you chase credibility, you’re playing someone else’s game, trying to look the part instead of doing the work. And that’s a losing strategy in startups, because none of us are actual credible to be doing most of the things we’re doing.

Startups are chaos by design. You’re flying the plane while you’re building it.  

That’s what Ben Horowitz meant in The Hard Thing About Hard Things when he wrote about “The Struggle” — that constant hum of doubt every leader feels:

Paul Graham said it another way: startups are “always on the verge of not working.”

It’s OK to feel that way. That’s not imposter syndrome. That’s just the cost of admission.

The trick is learning to live there without absolutely losing yourself.

In 1998, you could build quietly. Nobody gave a sh*t who you were. 

Today, the founder is the funnel. You can’t just build the thing, you have to narrate the build, tweet it, podcast it, live stream it, and then document the whole process. 

This is where I see a lot of founders struggle, where their imposter thoughts turn into a syndrome, and then, if they’re not careful, they can really multiply. 

You might trust your product completely, but still feel fake performing yourself.

And social media has just poured a liter of jet fuel on that fire.

You used to compare yourself to a few people in your orbit, the guys in your class, your neighbors, maybe some local hotshot who started an “online” business. 

Now you’re stacking yourself against every successful founder on the internet, all of them podcasting, posting, and personal-branding their “journey.” 

Trust me when I tell you, half of them are exaggerating, curating, or outright lying. The whole thing warps your sense of reality and makes imposter syndrome feel like the default setting.

A newsletter reader of mine recently told me he feels totally confident in his business model, team, and vision — but he freezes a bit when he has to talk about himself.

He worries it limits his ability to raise money or build business-critical relationships.

He’s not wrong to feel that way.

The modern founder has to live in two realities: the quiet, focused work of building and the noisy, performative work of telling. 

Both matter.

Talking about yourself often feels easiest when it’s in service of the work or about something you love.

Don’t force certain topics. And don’t “brand” yourself. Just narrate your process. Share what you’re learning, what’s working, what’s not. When the focus is contribution, not validation, the cringe starts to disappear.

(The most viral thing I ever wrote was highly personal -- it was an external narration of my decision to step-down from the CEO role at a really successful company. I wasn’t branding, or ‘trying’, just letting people into my process.)

You don’t need to look the part; you just need to actually be the part.

Quite literally translated to: just, be, you.

Charisma fades fast when it’s not backed by something real. The founders or builders who stand out the most aren’t the most confident or qualified, they’re the most authentic. 

They believe their own story, so everyone else does too.

(My wife’s been trying to scrub the sailor out of my mouth for years. No luck. I drop f-bombs the way some people say “um.” I always have. It’s not a branding choice — it’s just how I talk. And funny enough, that’s what people respond to. Not the polish, but the honesty.)

Your personal story shouldn’t feel like a résumé. It’s context for why the company exists.

Talk about what problem broke your brain enough to fix it. The pain that pushed you to start. The lessons you’ve learned along the way. Those are the things people are excited to hear about.

(Brian Chesky didn’t start Airbnb because he loved hospitality; he started it because he couldn’t afford rent. Three airbeds on the floor during a design conference became the seed for a global company built on belonging. Same with Melanie Perkins: she wasn’t chasing a billion-dollar idea, she was just tired of watching her design students suffer through Photoshop. Both founders built what they needed first and that honesty is what made their story resonate with everyone else.)

Every time you share something true and someone says “me too,” that’s a data point that’s helpful. It’s proof you’re not trying “too hard” or being an imposter.

Remember, you don’t need to convince people you’re credible; you just need to show them what’s true and let it resonate.

The more evidence you share — wins, losses, lessons — the more trust compounds.

(Think of Patrick Collison at Stripe or Sara Blakely from Spanx, who share what’s working and what’s not; that transparency is the credibility.)

I’ve had my own insecurities.

I worked at one company for 13 years. We grew it from $50 million to $400 million, but I wasn’t there from zero to one. And I certainly wasn’t the founder. 

Then I became CEO of The Hustle near the end of its run. Did cool stuff, but again — it wasn’t mine.

Then CEO of Hampton. I joined early, but not on day one. Close, but not founder-close.

I could certainly say to myself, Man, I’ve never built my own rocketship.

But here’s the truth: nobody’s story is pure, and everyone I have ever met is insecure about something.

The Boise founder wishes they lived in SF, the SF founder wishes they’d bootstrapped.

The one who exited way too early wishes they’d held on & gone bigger, and the one who missed the window wishes they had any exit at all.

We’re all just different flavors of second-guessing ourselves.

And trust me, I say that having the receipts to back it up. 

I’ve been behind the closed doors — the private groups, the Slack channels, the side texts — with a thousand-plus founders, hundreds of companies. I’ve sat at board dinners with John Mackey from Whole Foods, spent hours with Steve Kerr, the former Chief Learning Officer at Goldman Sachs. 

I’ve talked strategy with Google’s VP of Engineering, met Obama while at HubSpot. I’ve been behind the scenes at a $40B SaaS company, on the last-minute Zooms, in the rooms with founders going from $10M to $100M and figuring it out as they go. 

And I promise you this: nobody really knows what the f*ck they’re doing. 

Well, fine, maybe Obama did.

But, a little doubt keeps you honest. Keeps you curious. Keeps you awake.

Confidence isn’t something you are. It’s something you earn. One piece of evidence at a time.

So yeah, imposter thoughts show up. Just don’t let it turn into a syndrome. 

If you liked this blog post, you might enjoy this other one on the difference between luck and hard work.

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