A Billion Dollars Wasn't Enough

I got everything I thought I wanted. It wasn’t what I needed.

I was 25 when we started our company. If you asked me then whether we’d become a billion-dollar company, I’d say very unlikely. Most startups don’t make it, much less become a unicorn. Out of the 63 companies in our Y Combinator Summer 2011 class, not even 10% are still alive. Ten years later, we became a unicorn (at least on paper). What a moment… or so I thought. I was in a conference room with my executive team when we shared the news. They were thrilled. A colleague said, “Wow, this must be a big milestone for you. It’s everything you ever wanted, right?”

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.

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. ❤️