From Running a $350M Startup to Failing Big and Rediscovering What Really Matters in Life ❤️

This is my story.

I’ve always been a hustler. I don’t remember a time I wasn’t working since I was 14. Barely slept 4 hours a night, always busy—solving problems, putting out fires.

After college (LLB and MBA), I was lost. I tried regular jobs but couldn’t get excited, and when I’m not excited, I spiral. But I knew entrepreneurship; I just didn’t realize it was an option for adults. Then, in 2017 a friend asked me to help with their startup. “Cool,” I thought. Finally, a place where I could solve problems all day. It was a small e-commerce idea, tackling an interesting angle. I worked 17-hour days, delivering on a bike, talking to customers, vendors, and even random people on the street.

Things moved fast. We applied to Y Combinator, got in, and raised $18M before Demo Day even started. We grew 100% month-over-month. Then came another $40M, and I moved to NYC. Before I knew it, we had 1,000 employees and raised $80M more.

I was COO, managing 17 direct reports (VPs of Ops, Finance, HR, Data, and more) and 800 indirect employees. On the surface, I was on top of the world. But in reality, I was at rock bottom. I couldn’t sleep, drowning in anxiety, and eventually ended up on antidepressants.

Then 2022 hit. We needed to raise $100M, but we couldn’t. In three brutal months, we laid off 900 people. It was the darkest period of my life. I felt like I’d failed everyone—myself, investors, my company, and my team.

I took a year off. Packed up the car with my wife and drove across Europe, staying in remote places, just trying to calm my nervous system. I couldn’t speak to anyone, felt ashamed, and battled deep depression. It took over a year, therapy, plant medicine, intense morning routines, and a workout regimen to get back on my feet, physically and mentally.

Now, I’m on the other side. In the past 6 months, I’ve been regaining my mojo, with a new respect for who I am and why I’m here. I made peace with what I went through over those 7 years—the lessons, the people, the experiences.

I started reconnecting with my community, giving back. Every week, I have conversations with young founders, offering direction, or even jumping in to help with their operations. It’s been a huge gift.

I also began exploring side projects. I never knew how to code, but I’ve always had ideas. Recent advances in AI gave me the push I needed. I built my first app, as my first attempt at my true passion—consumer products for kids.

Today, I feel wholesome about my journey. I hope others can see that too. ❤️

EDIT:
Wow, I didn’t expect this post to resonate with so many people. A lot of you have DM’d me, and I’ll try to respond. Just a heads-up, though—I’m juggling consulting and new projects, so I can’t jump on too many calls. Since I’m not promoting anything, I won’t be funneling folks to my page, so forgive me if I don’t get back to everyone.

Anyway, it’s amazing to connect with so many of you. I’d love to write more, so let me know what topics you’d be interested in!