How I Really Hurt My Startup

My startup rocketship ran on my fear. Until it didn’t. Burnout is the greatest destroyer of enterprise value!

Around six years into my founder journey in 2017, we’d just raised our Series C, doing ~$30M ARR, and would triple that over the next three years. From the outside, everything was working. But inside, I was burnt out and depressed. Despite our incredible trajectory, in private I’d admit to feeling exhausted at the end of most days and waking up without the fire I once had. I’d come home and plop straight on the couch. I’d spend weekends cooped up in my bedroom, eating takeout and watching movies. I didn’t want to see anyone. I just wanted to hide. Not from the work, but from who I’d become… joyless, listless, mechanical. On Monday I’d put on a brave, smiling face and be the calm, fearless CEO I thought I had to be. I believed that things would fall apart if I slowed down, and it would be my fault.

I stepped down as CEO at the end of 2020 after nine years of sprinting. Looking back, I wish I had the courage to do so sooner. More importantly, I wish I’d worked in a way that didn’t burn me out. We obsess over markets, strategy, and competition. But the biggest risk to my company wasn’t any of those. It was me. I now believe that burnout is the greatest destroyer of enterprise value.

To be clear, I have no regrets. I’m insanely proud of our success. I’m also certain that we would’ve been even more successful had I worked more sustainably. Unfortunately, almost every founder I know also burns out. As our companies become more successful, we lose our creativity and joy. We become shells of our former selves. It doesn’t make sense. Our customers, teams, and investors all lose when we can’t play at our best. Imagine Serena Williams or Tom Brady having a career-ending injury at 22 years old.

How I Burned Out

1. I lived a one-dimensional, unbalanced life. I was maniacally obsessed with work and poured every waking minute into it. I couldn’t sleep. My mind wouldn’t stop ruminating. I didn’t make time for family, friends, and hobbies.

2. I denied myself truly restful breaks. I went nine years without a real vacation, convincing myself it was “leadership”. I believed that a real break would make me look checked out and uncommitted. “If I’m not working hard, they’ll judge me as lazy and work less hard”.

3. I tried to control everything. I didn’t trust anyone to do it as well as I could. I struggled to let go of my baby. Even when I “delegated”, it was often with a watchful eye over my shoulder. I needed everything to depend on me. It made me feel important and valuable.

4. I strayed from my Zone of Genius. I believed that a CEO had to do it all and be good at everything. I got stuck in my Zone of Excellence - tasks I can do with sheer willpower but that don’t energize me, e.g. budget reviews, OKR planning etc. I should have focused on what I’m naturally best at - recruiting, visioning, product, etc.

5. I didn’t ask for help. I was so in it. I refused to believe that I needed help. I judged vulnerability as weakness. I wasn’t aware of my unhealthy insecurities and coping mechanisms until far too late. I avoided therapy, peer support, meditation, and other forms of inner work until far too late.

Of course, not all hard work is toxic. And not all obsession is unhealthy. But I was past that point. As my company grew, so did my fear and ego. I sprinted even faster on a hamster wheel of my own creation, optimizing for a local maximum, not a global one. Inevitably, I hit a wall. Game over.

Most founders aspire to build enduring businesses. If we’re lucky, we get to work on something we love for ten, twenty, or more years. But we reward ways of working that make endurance nearly impossible. We forget that the goal isn’t to win the race. It’s to still want to run.