My Roadmap to Becoming a Confident Leader

How do we become confident Founders when none of us have ever done this before?

As a startup CEO for over 30 years, I can tell you I have the confidence now, but when I was starting at 19... not even close. I was so out of my depth I was terrified to even tell people I was a CEO for fear they would laugh at me. And they often did.

Back then, I thought confidence was something certain people were just born with — like being tall or having good skin. Growing up, there were always those kids who seemed like they had it figured out. I assumed they had something I didn’t.

Years later I'd come to know those same supposedly confident people very well, and I'd learn a valuable lesson — no one is just "naturally confident." It all comes from experience. But more so, it's an experience we can intentionally develop.

Here's how I did just that.

I Became the King of Questions

I didn’t try to fake being the smartest person in the room. I just became the most curious one. Most people avoid asking questions because they’re afraid it makes them look weak. But asking questions is one of the most powerful moves a Founder can make - because it signals something deeper: you’re here to learn, not to posture.

Back then, I’d walk into client meetings with a giant list of questions. That alone gave me perceived authority - the person asking questions feels like the one steering the conversation. That helped, especially when I looked like a teenager. And it got the client talking. The more they opened up, the better I understood what they actually needed.

Over time, those questions became answers. And those answers became experience. The confidence didn’t come from “knowing.” It came from being unafraid to not know. You can simply never ask enough questions.

I Made Big Plays

Confidence grows in the space between “I don’t know how” and “I’ll figure it out.” I forced myself into hard situations (over and over) where I had no choice but to level up. One of the first was at 19, pitching a major client. They asked if we could build them an e-commerce site — back when e-commerce basically didn’t exist.

We didn’t know how to write real code. We had no idea what a shopping cart system looked like. But I said “Of course!” — mostly out of pride. Then we figured it out. We pulled long nights, found the tools, and delivered one of the earliest e-commerce sites on the internet. That moment rewired me. It told me that my confidence wasn't going to come from what I had done, but what I can do.

That small win would tee me up just a few years later with the confidence to pitch a major Fortune 500 client. We were a tiny 50 person agency with no business pitching at this level, but we went all in and landed one of the most lopsided agency wins in history — a quarter billion dollar per year account that turned us into a billion dollar company. Confidence pays major dividends.

I Got Good at Being Wrong

Early on, I thought confident leaders always knew the right answer. And since I was constantly uncertain, I figured I wasn’t qualified. But I eventually learned: confident leaders don’t avoid being wrong — they get good at it.

They’re not confident because they’re always right. They’re confident because they trust themselves to recover. That shift changed everything. I stopped seeing mistakes as disqualifiers. I stopped needing to be “sure.” I became more decisive — not because I knew I’d succeed, but because I believed I could adapt if I didn’t.

It’s not easy. Especially when everyone’s looking at you like you’re supposed to know something they don’t. But real strength - the kind that builds lasting confidence - is saying, “I might be wrong. But I’ll learn fast. And I’ll make it right.” That’s what lets us take big swings. That’s what keeps us growing. Confidence isn’t certainty. It’s resilience in motion.

Confidence is Built, Not Born

If you’re waiting to feel confident before you lead — stop waiting. You don’t need confidence to begin. You need curiosity. You need a willingness to be wrong. You need to step into situations that force you to grow faster than you feel ready for.

Leadership isn’t about being right. It’s about being present. It’s about being accountable. And it’s about being willing to bet on yourself — even if no one else would.

That’s where confidence really comes from. And the best part? You don’t need to fake it. You just need to build it.

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