Talk: "Afraid to Fail" at Drexel's Close School of Entrepreneurship

I used to think entrepreneurship was about being fearless. That it was that romantic vision where a founder takes a leap, figures it out along the way, and relentlessly executes on their way to startup glory.

There’s some truth in that.

Every startup story starts with a leap.

But that kind of courage is easy when there’s little to lose.

As a startup grows, the stakes rise: investors start believing in you, employees start depending on you, and your reputation as a founder becomes something you'll do anything to protect.

As that pressure mounted and when the metrics at my adtech company stalled, I didn't respond with curiosity or objectivity or responsibility: I responded with fear.

I didn't see that at the time. I don't think anyone around me was interpreting fear, either. It manifested (outwardly) as bravado and confidence.

But it's now clear I was terrified.

I had already unknowingly begun my journey through the universal patterns of startup failure, fusing my identity with that of my startup. That distorted everything. I told myself that I was fighting for the company, but I was really operating in a personal survival mode like a cornered animal.

I was defensive, reactive, and began rationalizing decisions I never would have otherwise considered.

Eventually, the company collapsed.

And standing in a courtroom months later, a judge looked at me and said something I'll never forget:

It seems you just didn't know how to fail.

She was exactly right. I had no idea how to handle disappointing the people who believed or relied on me.

Instead of objectively working through the many challenges in our operation, I started asking "what will buy me more time?" I started chasing narrative over substance. And perhaps worst of all, I isolated from the many talented mentors that I had engaged with along the way.

What I Told Students at Drexel's Close School of Entrepreneurship

As I shared the story of Benja and the dangers of "fake it 'til you make it" with Drexel students, I also unpacked what fear can do to founders.

Fear narrows your field of view and collapses your time horizon. It convinces you that if you can just survive this week, this round, this deal, things will finally settle. It drives you away from fundamentals and operations, toward narrative and optics.

And eventually, it erodes something fundamental: your ability to be objective and honest.

When you lose that, you stop telling yourself the truth. And when you stop telling yourself the truth, it becomes impossible to be honest with those around you.

There's no question that's what happened in my story.

But fear is a constant in every founder's journey. You can't eliminate it and you can't out-run it.

What you can do is learn to carry it. To see it clearly, to hold it in view, to let it inform you without letting it drive.

That's the discipline of entrepreneurship: to stay honest when denial feels safer, to stay objective when your instincts are screaming to survive.

Because once fear takes the wheel, it's over.

It won't crash the company overnight.

It'll do it slowly, quietly, and convincingly - while you're still telling yourself that you're in control.

This talk, which is part of my work on the patterns of startup failure, was delivered at the Drexel Close School of Entrepreneurship in October 2024. Thank you to Chuck Sacco and Robert Morier for their hospitality, and to the students for their attention.