Re:Start

A year has passed since I parted ways with Cater2.me. The anniversary came and went, and I hardly noticed.

About six months ago, deep in the throes of confusion about what I wanted to do next, I committed to giving myself a full year of rest. I told myself I didn’t need to figure out my next professional chapter immediately. I could take some time, decompress, and eventually the answer would become clear.

Well, the year has come and gone, and I’m no closer to knowing what comes next. For better or worse, I’ve settled into a comfortable daily rhythm centered largely around family life. I spend some of my time advising a few startups and working on projects as they momentarily capture my interest, but I haven’t committed myself fully to anything. And as more time passes, I’ve noticed something that makes me uncomfortable: my ability to focus on starting another business seems to be slipping, while my hesitation about taking on something big seems to be growing.

That has led me to a more fundamental question than what I should do next: Who am I?

For a long time, I had a pretty clear answer. I centered my self-image around my work ethic, focus, and resilience. I felt most comfortable when I was working on something difficult and most gratified when I achieved a hard goal. I was the guy who didn’t shy away from challenges, who could endure more than other people, who would keep going when things got difficult.

Now, when I contemplate throwing myself back into the fire of early startup life, I’m more hesitant and, perhaps, more scared than I ever expected to be. That unsettles me because it calls into question not just what I want to do, but the person I thought I was.

When I started Cater2.me, my sense of myself was largely unformed. I was 26. I knew I wanted to try something hard, and I gave myself over to the task. I was a lump of clay, ready and willing to be shaped by whatever came next. And Cater2.me did shape me.

Through years of trial and error, success and failure, exhaustion and persistence, I gradually developed an image of myself as a leader, as someone who didn’t shy away from challenges, and as someone with an almost inexhaustible supply of resilience and grit. More than anything else, though, I became someone whose life revolved around work.

Even after I got married and had kids, work remained my primary focus. I tried to be there for my family, and in many ways I was. But I also knew that only part of me was ever truly focused on them. Somewhere in the back of my mind was always an employee problem, a client issue, a cash flow concern, or some other fire waiting to be put out.

Over the past year, I’ve experienced something very different. I’ve joined the PTA at my kids’ school. I’ve taken on more of the planning and management of our household. I’ve been more physically present with my family, but more importantly, I’ve been more mentally present. My attention isn’t constantly being pulled somewhere else and I’ve really enjoyed it.

What I didn’t expect was how much that life would crowd out some of my ambition. Perhaps it was naive to think I could simply add greater involvement with my family on top of the person I already was. I assumed I could be just as professionally ambitious and driven while simultaneously making family a much larger part of my life. Instead, I’ve found that attention is finite. As one part of my life has expanded, another has contracted. I don’t think I’ve fully come to terms with that.

There’s another part of this transition that is harder for me to admit. At times, I’ve felt a slight sense of embarrassment about the life I’m living now. When I’m walking around in the middle of a weekday or helping with something at my kids’ school, I sometimes catch myself wondering how other people see me. There’s a voice in my head telling me that, as a man in his early 40s, I should be out working. Building. Achieving.

I’m not sure where that voice comes from. Maybe it’s cultural. Maybe it’s the environment I’ve spent my adult life in. Or maybe I simply spent so long defining myself as someone who created economic value, employed people, and built things that I don’t quite know how to value myself without those markers.

The irony is that I don’t view this past year as wasted time. Quite the opposite. Being more involved with my kids, my family, and my community has felt meaningful in ways that work often didn’t. Yet some part of me still seems to believe that the work counts more.

I’m trying to figure out whether that discomfort is telling me something. Maybe it’s a signal that I’m ready to get back out there. Maybe the itch to build something is returning, and I’m beginning to miss an essential part of myself. Or maybe it’s just another piece of an identity I spent 15 years constructing that I need to learn how to let go.

When I left Cater2.me, I thought of myself as fully formed. Cater2.me had taken that 26-year-old lump of clay and hardened it into something recognizable. I knew my strengths, my weaknesses, what motivated me, and what I was capable of enduring. A year later, I’m not so sure.

Maybe the mistake was thinking that the person Cater2.me shaped me into was the finished product rather than simply one version of me, built for a particular time and a particular challenge. I don’t know what shape I’ll take next. I don’t even know yet whether another company will be part of it. But perhaps figuring that out requires becoming comfortable with being malleable.

An object in motion stays in motion. An object at rest stays at rest. Newton’s First Law refers to physics, but I’ve found the principle applies just as well to work.

On a day-to-day level, starting a project can feel like pushing uphill, forcing yourself to focus, shaking off the urge to procrastinate, peeling away from whatever you were doing before it’s time to settle in. But once you’re over that initial hump, the day flows. The same dynamic plays out over longer stretches: go on vacation in the middle of a busy work period, and it takes a day or two to actually decompress. By the end, the thought of returning feels almost painful.

This pattern has continued since I left Cater2.me last year. At first, I felt the pull to charge directly into the next thing; I couldn’t imagine what it would feel like to not be consumed by work. But over the following months, I started to loosen the grip of the always be working mentality and got more comfortable with being at rest. The question I ask myself almost daily now: am I getting too comfortable? Will I be able to break out of this restful inertia when the time is right?

When I was contemplating leaving Oliver Wyman to start a company back in 2009 and 2010, I never got the chance to ease off, so I never had to experience the pain of starting anew from a standing stop. I brainstormed and ideated on Cater2.me while still fully engaged in my day job. When I resigned in mid-August 2010, I took no time off and Cater2.me was officially formed at the beginning of September. Looking back, it seems crazy that I didn’t take even a short break. But at the time, I needed to work, knew I’d be without income for a while, and a prolonged break wasn’t feasible. More than the practicality of it, though, the simple inertia of staying in motion felt easier than slowing down and then having to speed back up.

I don’t want to give the wrong impression about what this current rest period actually looks like. My natural tendency toward productivity keeps my days structured and pushes me to seek out things to check off to achieve the Type A dopamine hit of finishing something. I’ve kept up with advising startups I’ve invested in, joined my kids’ school’s PTA board, set up a daily and weekly task structure to make sure I’m using my time well, and continued to brainstorm new business ideas. There’s still a self-imposed pressure to stay busy and useful. But the idea of leaving this period behind to start something big feels more and more daunting the further I get from the constant mental weight of running a company.

When the right idea comes along, I’m sure I’ll be able to overcome the inertia, it just won’t be easy. You’ve got to hand it to Isaac — he knew what he was talking about.

From -1 to 0

If the amount of time since my last post is any indication, the journey from -1 (no idea for a new venture) to 0 (the start of something new) has been far less straightforward than I expected.

I imagined I’d jump into brainstorming mode, start viewing the world through an entrepreneurial lens, and suddenly… Eureka. An idea would emerge, and I’d be off to the races.

After all, that’s more or less how it worked the first time. When Zach and I decided to start a company, we built spreadsheets to track ideas, walked through business school frameworks (SWOT, 4 P’s, and the rest), researched markets, tested assumptions, and in a reasonably linear fashion, Cater2.me came into focus.

This time around has been anything but linear.

Losing the anchor

Since leaving Cater2.me late last year, I’ve been questioning who I am in a way that’s been both deep and uncomfortable.

For most of my adult life, I’ve had a clear identity and a clear mission. I could pick a path and commit to it completely. But without my company and role to define me, I’ve felt unmoored. I’ve started asking questions I never had to confront before: Do I still have what it takes? And even if I do, do I want to use it again?

I threw myself into Cater2.me. I worked 100+ hour weeks. I took on the most mundane and frustrating tasks because someone had to do them. I sacrificed constantly and was mostly happy to do so because I was driven by something powerful: the need to prove myself. I also had a youthful naiveté that helped me push forward even when things were bleak, trusting that somehow it would all work out.

Now, at 42, with school-aged kids, I don’t know if I can or want to operate that way again.

For someone who has always prided himself on endurance and resilience, doubting my own work ethic has been unsettling. I know exactly how much effort it takes to build a company. Will I still succeed if I don’t outwork everyone else? Has experience replaced brute force? Can I repeat what I did with Cater2.me?

I’ve found myself spiraling through these questions, pausing in ways I never used to, reexamining parts of myself I assumed were fixed.

Fear enters the room

Alongside questioning who I am, I’ve been questioning what I’m even trying to do.

Now that I’ve tasted success, do I want a bigger mountain to climb? Or something smaller? Easier? More controlled? Do I want to go down the entrepreneurial path again at all?

These doubts have surprised me. When Zach and I first decided to start a company, there was no wavering. I had no guarantee of success, but I knew I had to try. I was overwhelmingly confident we’d figure it out, despite the statistics telling us otherwise.

Today, having seen how much luck was involved, and how many startups failed alongside us, I’m afraid of failure in a way I wasn’t before. Experience has replaced ignorance, and confidence has given way to caution.

The missing deadline

Another unexpected factor: the absence of urgency.

Back in 2009, Zach was nearing the end of his analyst program at TPG Growth. He had to decide between business school, another job, or starting a company. That imposed a real timeline. We knew we had less than a year to make something happen, all while working full time.

That constraint forced discipline. It created momentum. It moved us forward.

This time, there’s no deadline. No forcing function.

I assumed I’d be eager to jump back in, but without external pressure, it’s been surprisingly easy to justify a slower, more meandering pace. Comfort has a way of quietly draining urgency.

Finding community in uncertainty

Before closing, I want to acknowledge something that’s helped me navigate this strange in-between period.

At the suggestion of a fellow exited founder, Patrick Ambron, I joined a community called Post-Exit Founders (PEF). It’s a group of more than 5,000 founders who’ve sold their companies.

More than anything else, PEF has shown me that I’m not alone in feeling this way.

The self-doubt. The loss of direction. The identity questions. They’re common. Being surrounded by people who’ve gone through the same transition has been grounding. Through the group, I’ve come across case studies and academic research that pose deceptively simple but profound questions:

“What do I want my eulogy to say?”

“What actually brings me enduring fulfillment, satisfaction, joy?”

These questions have forced me to slow down and reflect on who I am and who I want to be.

Still walking

I don’t yet have all the answers. I’m still not close to completing the journey from -1 to 0.

But I’ve reaffirmed something important: I still want to be at -1. I still feel pulled toward building. Toward creating. Toward seeing what’s possible.

The road ahead will almost certainly be winding. But I’m moving forward with the quiet confidence that I’m not walking it alone.

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.

Starting and running my first business, Cater2.me, was the most stressful, rewarding, terrible, incredible thing I’ve done in my life. For 15 years, I, along with my cofounder, Zach Yungst, was on the front lines of the entrepreneurial experience as we took the company from birth in September 2010 to its ultimate exit in November 2024.

The origin of Cater2.me goes back even further, as we started to brainstorm ideas as early as 2009 that would allow us to leave our corporate jobs and start on the path to self-sufficiency. Along the way, from original ideation all the way through to exit, we did plenty right but also made myriad mistakes.

This blog is about my quest to start another business, and as I go, to compare the major steps and milestones against the first time to see what I’ve learned and what has changed, for better or for worse. I hope that you, the reader, will learn something about the entrepreneurial process and can profit from my experience.

Ever since I left Cater2.me, and for some time before that, I have thought long and hard about whether I want to start another company. I still have that entrepreneurial itch and it’s time to scratch it again. Let’s get started.

This is Re:Start.

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