How a Bag of Cash Led Me to Cybersecurity

I was a theater nerd in high school—the kind who memorized monologues, lived for the stage, and dreamt of dramatic entrances. But my real-life plot twist didn’t happen under a spotlight. It happened in the paddock at the Saratoga Springs, NY racetrack, where I found myself, at 19, wearing a navy blue polo shirt, a security badge, and holding something that would change the trajectory of my life: a sealed envelope containing a quarter million dollars in cold, hard cash.

And I wasn’t just holding it.

I was escorting it—from the vault at the track to the bursar’s office downtown—flanked by an off-duty NYPD cop who had probably seen more chaos than I could even imagine.

I was a kid. I was barely out of high school. I was trusted with something so valuable, so tangible, that I felt the weight of it not just in my hands, but in my gut.

That envelope—thick, silent, pulsing with meaning—taught me something in that moment: security isn’t just about protection. It’s about responsibility, integrity, and trust.

Fast forward a couple decades.

I’ve worn many hats since then—working in TV newsrooms (where I watched 9/11 unfold in real time), building geo-targeting platforms before AI was mainstream, fielding media calls about Sandy Hook on my first day at an emergency alert system company, and helping defense contractors develop radar systems to protect national interests. I even opened my own coaching company somewhere in between.

But the thread? Always: security.

And now, I’m back in it—deeply.

Only these days, I’m not carrying cash.

I’m securing data—the gold of the modern world.

What used to be paper bills stuffed into envelopes is now encrypted traffic, user credentials, private health records, proprietary code.

And just like that envelope of cash, these digital assets are valuable, vulnerable, and often in the wrong hands.

Security isn’t a career I sought out—it’s a calling that found me again and again. From the Saratoga racetrack to the frontlines of cybersecurity, I’ve come to believe this work isn’t just technical—it’s personal.

Because what we’re really protecting isn’t just systems.

It’s people. Reputations. Dreams. Livelihoods. Truth.

As I launch CyberSoul—my upcoming podcast—it was born from that same sense of urgency I felt with that envelope all those years ago. A fire in my belly. A knowing that this matters.

We are in a moment where ransomware hits every day, breaches make headlines, and trust is a fragile commodity. But instead of giving into fear, I want to open up conversations.

Real talk. Human talk.

About where we went wrong.

About what leadership in tech really looks like.

About how to protect the digital world—without losing our souls in the process.

So yes, I was a theater nerd.

Yes, I once guarded jockstraps and stacks of cash.

And yes, I now sit at the table with CISOs, engineers, and entrepreneurs asking the most important question of all:

How do we make tech human again?

Because in this digital age, securing data isn’t just a job.

It’s a revolution.

And I’m here for it.

Want updates on CyberSoul? Stay tuned. The podcast is dropping soon. Until then—keep it human, and stay secure.