Why am I doing this to myself (again)?
The First Decision - 2010
As the calendar turned to a new year in 2010, life was simple. I was 26, three and a half years into my job at Oliver Wyman, and on a predictable path toward becoming a partner. I enjoyed the travel, the expense-account lifestyle, and the company of sharp, ambitious peers. The next steps were clear and attainable—if I just kept climbing.
And yet, in the middle of that comfort, I made a decision that seemed reckless from the outside: to leave a stable, well-paying job and start my own company. I knew the odds of failure were high, but I couldn’t shake the urge to try.
Consulting had been stimulating but ultimately hollow. I was constantly learning new industries just well enough to advise people who’d spent decades in them—a process that now feels faintly absurd in retrospect. The work was intellectually demanding but not creative. I wasn’t building anything tangible or enduring. I wanted to make something of my own and feel the consequences of my decisions directly.
My personal circumstances made that leap possible. My girlfriend at the time (spoiler alert, we’ve been married 13 years now) was deep in medical school, I had no kids, no debt, and few obligations. I could take a risk without upending anyone else’s life.
But the push wasn’t just situational—it was deeply personal. Both of my parents ran their own medical practices, and even as a kid I felt proud knowing they were the ones “in charge.” They built something that gave others work and delivered real value. That model of independence stuck with me. It’s what led me to Wharton and, eventually, to committing to my friend and future cofounder, Zach, that I was ready to start something. I wanted to feel that same sense of ownership and creation my parents had modeled—and maybe someday pass it along to my own kids.
The Next Decision - 2025
5,187 days (but who’s counting?) after founding Cater2.me, I sold the company. I stayed through the transition and, a few months ago, officially stepped away. Now I find myself asking the same question I faced 15 years ago: Should I start another company?
This time, the context couldn’t be more different. I’m married, have two young kids, and a life full of responsibilities. I’m older, hopefully wiser, and battle-tested from more than a decade in the startup trenches. I’ve built something real—an organization that employed hundreds and helped other companies thrive. I’ve proven, at least once, that I can shoulder the weight of entrepreneurship.
And yet I remember just how heavy that weight can be. For nearly 15 years, my identity was fused to the company. The stress, the worry, the relentless self-questioning—they became constant companions. Only other founders seemed to truly understand. I often wondered why I kept pushing so hard, even when I was exhausted or unhappy. So why would I willingly step back into that world?
Part of it is self-knowledge. I’ve learned that I operate best under pressure. I draw energy from challenges and take pride in endurance. I may not always be the smartest person in the room, but I’ll outwork anyone.
Another part is curiosity. I want to see what a “second time around” looks like. I’ve watched peers become masters of their respective crafts—medicine, law, finance. My own craft is messier: it’s the combination of leadership, resilience, creativity, and judgment that comes with founding and running a company. I want to test whether those skills are truly transferable.
And finally, there’s legacy. When I sold Cater2.me, I told my son—then seven—about this great accomplishment. His immediate response was not what I was expecting: “So you’re not the boss anymore?” The question lingered longer than I expected. It reminded me how much of my identity, and the example I want to set for my kids, is tied to building and leading something of my own.
Sitting here in 2025, my stakes are higher now, and the calculus is more complex. But the same impulses that drove me 15 years ago—the desire to create, to lead, to test myself—are still there. Maybe that’s what it means to be an entrepreneur: to live in that restless space between fear and ambition, between knowing what it costs and wanting to pay the price anyway.
