In that moment, I forced a smile. We had won the lottery. My 25-year-old self was grinning ear to ear, his wildest dreams exceeded. And yet, somehow I felt empty. Why isn’t this enough? If exceeding my wildest dreams doesn’t make me happy, what will? I had chased this goal for a decade, ready for the pot of gold at the end of the rainbow. Surely, this success would make me feel worthy. Surely, I would belong. Unfortunately, it was a mirage. I couldn’t fill the hole in my heart with more of what created it.

In that same week, my friend Brian was taking Coinbase public at an $85 billion valuation. I was thrilled for Brian. He gave us a shot when he was an engineer at Airbnb, who then became our first customer. Back then, Airbnb was “just” a billion-dollar company. When he left to start Coinbase, I recommended him into YC. Coinbase then became an early customer and helped us a lot. Without Brian, our trajectory might’ve been very different.

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But as I received notes of congratulations that week, all I could think about was how Coinbase accomplished so much more than us in less time. I didn’t build what Brian built. My billion-dollar company isn’t enough. I’m less than. I was fixated on what was missing, unable to appreciate all the good in my life. Comparing myself to others instead of my past self meant that even miracles were never enough. I had defined winning and losing within a finite game. The problem wasn’t the goal. It was that I kept moving it. I didn’t need a bigger win, I needed a different source of self-worth. Tying my self-worth to external measures like valuation was a recipe for misery. I’m certain that if we went public at an $85 billion valuation, I’d compare myself to businesses trading at a trillion-dollar valuation. I’d still feel inadequate.

Nothing in life is free. Every version of success comes with a cost. The question isn’t whether we’ll pay. It’s whether we’re conscious of the price. After a decade of sprinting as CEO, I was most depressed and burned out when we became a unicorn. I had gained more than 100 pounds from stress eating and not exercising. I did lasting damage to my body. I skipped family vacations and friends’ weddings and birthdays. My identity as a competitive, successful winner improved my local maximum at the cost of my global one. I had won on one dimension, but lost on many others. Was this winning? Was it worth it?

I didn’t invent my take-no-prisoners drive. It blossomed from my culture. Moments of praise (or lack of it) and criticism. An A wasn’t enough. It had to be an A+. I built a belief that my worth had to be proven. That success meant becoming someone. That if I had no value if I wasn’t producing. While I have no regrets, it’s now clear that I wasn’t really in the driver’s seat. Much of my journey was driven by my subconscious fear, ego, and scarcity mindset. So of course I couldn’t feel happy when we became a unicorn. Of course I burned out and struggled with depression. When we run on dirty fuel, the engine eventually breaks.

Ambition is healthy. It keeps us hungry. But ambition without enoughness is a toxic bottomless hunger that cannot be fed. “I’m not enough. I need more.” Some may contend that enoughness and ambition can’t coexist. This confuses enoughness with toxic complacency. Enoughness is the healthy soil from which sustainable, meaningful ambition emerges. There’s no tradeoff. We can believe both “I am enough” AND “I want more - but I don’t need it”. We should strive for greater heights - but from a place of love, service, and abundance, instead of fear, ego, and scarcity. Clean vs. dirty fuel.

These days, I try to approach work with less to prove. I’m still wildly ambitious, but I try to be less attached to the outcome. I’m trying to be kinder to myself and celebrate every moment. I still catch myself slipping back into old patterns… it’s not easy to rewrite my operating system from within. It’s like unlearning a language I’ve spoken my whole life. If I could go back in time, I’d tell my younger self that it’s OK to want to win - you just don’t need to. You’re enough as you are, forever and always. ❤️

My productivity obsession was fear and ego wearing a costume. I needed to be seen as a hard worker. It was my identity. I derived self-worth from it. I was scared of being judged as lazy and uncommitted. Truthfully, I was already judging myself. I wore my nonstop back-to-back calendar like a badge of honor. I stacked my trophy case with 80+ hour weeks. I got drunk on busyness. Almost always last to leave the office. Look at me, I’m working so hard. I’m setting a good example for my team. But by the end of the day I was too tired to do meaningful work. I’d just mindlessly scroll Slack. Read articles. Stare at a blank screen. My time would’ve been better spent resting, exercising, or seeing friends.

Even rest felt uncomfortable. If I’m not grinding, I’m failing. I’d step away but never truly unplug because a good leader is always there for their team. After nine years of sprinting as CEO, I finally took a six-week sabbatical. “Call me if there’s an emergency.” When I returned, my colleagues said that I was a different person. Calm. Positive. Thoughtful. Energized. Unfortunately, it wasn’t enough to fully refill my tank. My burnout and depression were irreversible. Elite athletes treat rest and recovery as part of the work. We should too.

As we scaled, my need for control and maniacal attention to detail worked against me. I focused on everything, which meant that I focused on nothing. Yes, sometimes Founder Mode is needed. But I wanted perfection everywhere. I’d send a 2 AM email calling out a typo in a support ticket. Occasionally, it was a good use of my time. More often, it was a toxic outlet for my stress, anxiety, and insecurity. I bottlenecked my team. More hours. More context switching. Less impact. Local maximums over global ones.

Now I ask leaders three questions:

1. Have you ever had a day where you got more done than an entire week?

2. If we audited your past quarter, what % of your hours actually moved the needle?

3. How would you work if no one rewarded busyness?

We say we value results. But we often signal that we value activity and visible effort. We reward the fastest reply, not the best thinking. The loudest voice, not the insightful question. The firefighter, not the one who prevented it. Winning over learning. Our teams optimize accordingly. And we wonder why we’re not moving the needle.

Hours worked is a vanity metric. We currently optimize Time ➡️ Impact. This is broken. When the Time vs. Impact curve goes sublinear, the solution isn’t more hours. It’s to change the slope.

The real equation is Energy ➡️ Impact. When we’re not feeling inspired, focused, and creative, we shouldn’t force output. We should change state. Travel. Dance. Watch a movie. Meditate. Whatever it takes to get back to flow.

To be clear, I’m not anti hard work. I’m a fan of 100 hour weeks if we’re in flow. If we’re inspired. But mindless low-impact work is just motion without progress. A traditional 40+ hour week isn’t discipline. It’s an Industrial Age ghost haunting our Creative Age. Stop clocking in and out. Start compounding impact. Or don’t. Just be honest about what it’s costing you.

Side note. Last year I was diagnosed with severe ADHD. “A Ferrari mind with bicycle brakes”1. It means that my attention scatters, and so does my impact. A task that should take an hour might take two. I’m honestly impressed that I was as successful as I was. And I would’ve been even more successful if I had gotten help sooner. I suspect many founders are in the same boat. Neurodivergence is both a superpower and a liability. I encourage proactive diagnosis, and if you have it, learn how to manage its downsides. Knowledge is power!

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.