From Layoff to Launch: How Losing My Job Led Me to Start My First Business

Apologies for the gap since my last newsletter—it’s been a month! I recently had the incredible opportunity to travel to Chile with Dahlia, who, as a travel planner, took us to incredible hotels and on amazing adventures. I was happy to tag along as her “secretary” (a role I’m happy to play when she’s in charge) and enjoy the ride as her plus one.

DM me if you want more information about Santiago, Patagonia, Torres Del Paine, or Chiloé Island in Chile.

Now, back to the story.

I stumbled into the greatest career one could ever ask for in 1996. The Web was new, and the question of how entrepreneurs could monetize it was very much on everyone's mind. The online advertising industry was born, and I happened to be young, cocky, in NYC, and willing to work for nearly free.

My first real job was signing publishers up for the Cliqnow! ad Network, which later became 24/7 Media. We grew from dozens of employees to thousands, with offices around the world. I was a paper millionaire at 24, and I believed that with my incredible talent, hard work, and ambition, my career was only going up!

When I got laid off in 2002, I had more questions than answers. How could this happen to me? Don’t they know who I am!?

Getting laid off hit hard. There’s a certain shock that comes with that sudden shift, a wake-up call that maybe I wasn’t quite the unmissable talent I’d thought I was. If you’ve been there, you know: it’s humbling. And, truthfully, it was one of the best things that could have happened.

I had a moment of clarity in that uncertain space. I realized that if I was going to bet on anyone, it had to be myself. The very next day, I sat down, gathered my thoughts, and started my first business. It wasn’t a fully formed idea yet—more of a rough vision powered by pure necessity and adrenaline. But I dove in, learned as I went, and leaned into the process.

Reflecting on that journey, I learned three key things I’d never have grasped otherwise:

1. Humility fuels growth. Getting knocked down reminded me of the power of staying curious and adaptable. No one has it all figured out.
2. Betting on yourself is powerful. Starting from scratch with no guarantees isn’t easy, but it’s incredibly liberating.
3. Every setback has a purpose. That layoff was a turning point that forced me to step up, innovate, and take ownership of my career in a way I hadn’t before.

For anyone else facing a professional setback: take it as an opportunity. Sometimes, losing your footing is the only way to find your path.