How Crashing a Nightclub Taught Me to Win at Startups and Venture Capital
On New Year’s Eve 1990, I was 14 years old, standing outside a club in Manhattan with a VIP ticket in my hand that might as well have said “this kid does not belong here.” My black-on-black outfit was carefully calculated, sleeves rolled to just the right fold, and my suede Dr. Martens had seen maybe one other party: my friend’s bar mitzvah. I was freezing, faking, and fully convinced that if I didn’t get into that club, my life would be over.
That night, I got in. Barely. And that moment — that freezing, awkward, exhilarating, low-key fraudulent moment — is when I learned something I’ve carried through every business I’ve built and every founder I’ve backed:
Success is just getting past velvet ropes over and over again.
Whether it’s a bouncer, a gatekeeper, a skeptical investor, or a stubborn customer, the rules are the same. You either learn the game, or you get left out in the cold.
Let me explain.
1. The Gate Isn’t There to Keep You Out. It’s There to See How You Handle It.
We show up to Elements - this massive warehouse-looking club in a sketchy part of town - and we’re immediately told we’re in the wrong line. I’m thinking: “There are two lines. Same door. What the hell’s the difference?”
Welcome to nightlife logic. Also: welcome to venture capital.
In life and in business, there are two doors that look identical. One is “general admission.” The other is “VIP.” And the only difference? Perception. Positioning. Presence.
It’s all a test. They’re watching how you respond. Do you panic? Do you apologize for existing? Or do you take the cue, switch lines, and act like you belong there?
In startups, this is your first pitch meeting. Your cold email. Your half-built product. You’ve got 30 seconds to prove you’re not just another name in the “general” pile.
And if you're standing in the wrong line?
Move. But don’t flinch.
2. Fake It — But Not Like a Fraud. Like a Future You.
Listen — I’m not telling you to lie. But I am absolutely telling you to strategically exaggerate your potential.
At 14, I had no business being in that club. But I walked in with Fred’s name on my lips like I was his right-hand man. That night, I became a master of “act like you’ve been here before.”
Years later, when I built JoonBug, I didn’t pretend we were some nightlife empire — we operated like one. We sent newsletters before Mailchimp existed. We built a digital ticketing system before Eventbrite was a domain. We hired 100 photographers before Instagram was even a glimmer.
No one knew who we were until we told them. And then we didn’t shut up.
As a founder, your entire early-stage runway is you faking being bigger, better, and bolder than you technically are — until you’re not faking anymore.
3. You’re Not Selling a Product. You’re Selling a Fantasy.
Let me tell you a secret about clubs: when the lights come on, they all look like busted gyms with overpriced liquor. The real product is the feeling.
When you walk in and it’s pulsing, exclusive, sexy — that’s what you’re paying for. The crowd, the vibe, the music, the illusion.
That’s exactly how startups work.
I don’t care what your app does. What does it feel like to use? Are you solving a real problem, or are you just adding another feature to the noise?
At JoonBug, we didn’t sell tickets. We sold the feeling of being somebody. Of belonging. Of access.
As a founder, remember: no one cares about your codebase. They care about how your product makes them feel about themselves while using it.
4. The Gatekeepers Are Just People — But You Still Need to Play the Game
That doorman that gave us the side-eye and made us switch lines? He didn’t care about our ticket. He cared about protecting the brand, the vibe, the look.
And guess what — so do VCs. So do buyers. So do media outlets. They all have something they’re protecting.
You can hate the game all you want, or you can learn what they’re guarding and speak directly to it.
Are you a first-time founder with no traction? Fine. What narrative are you giving me? What edge? What unfair advantage?
Don’t show up cold. Show up compelling.
5. In the Business of Cool, Data is King
Let’s get one thing straight — I didn’t build the hottest club. I built the engine that powered the hottest clubs.
While others were handing out flyers, I was collecting emails. While promoters were fighting for bottle service spend, I was building a database that Johnnie Walker and Mercedes paid top dollar to get in front of.
I wasn’t chasing celebrities. I was controlling the crowd.
In startups, everyone’s obsessed with product. But if you control distribution? You win.
Whether it’s users, eyeballs, emails, or attention — your ability to move people at scale is your power. Protect it. Grow it. Monetize it.
6. Always Be Throwing the Next Party
The hardest part of nightlife wasn’t getting people in the door. It was doing it again next week. And the next. And the next.
You’re only as good as your last party. You’re only as good as your last raise, your last release, your last W.
Momentum matters.
As a VC now, I see it all the time — founders sitting on a win from 2 years ago like it’s still hot. It’s not. Nobody cares. What’s next?
At JoonBug, we threw 300+ events a year. I was at the club until 4am and in the office by 9. The hustle was real — and relentless.
If you’re building something, remember: the market has the memory of a goldfish. Don’t just have a moment. Have a movement.
7. Know When to Leave the Party
Nightlife taught me how to get in. It also taught me when to get out.
Eventually, I got tired of the late nights, the bouncer drama, the 5am payout fights. I realized the same skills I used to build JoonBug could build something way bigger.
So I built EZ Texting. Then I started investing. Now I help other founders find their version of the velvet rope — and kick it down.
The party doesn’t last forever. But the lessons do.
Wrap-Up: Bring Your Own Rope
If you take nothing else from this, take this:
You don’t need to wait to be invited. You can build your own velvet rope, open your own doors, and throw your own damn party.
Startups are hard. Breaking in is brutal. But if a 14-year-old kid from Long Island with a fake ticket and real guts can get into a 21+ club and build a tech empire from that energy — you can do this.
Show up with confidence.
And never — never — wait in the wrong line again.
See you on the other side of the ropes.
