On 22 and playing with house money

I started this post back in March, around when I turned 22, as a way of reflecting on almost graduating and just life in general. As one does. The first few times I tried to write it, the idea I kept coming back to was "playing with house money." It felt like the perfect phrase for the way I had done my best work in college:

1. by playing
2. disconnected from specific ideas of success
3. and free from the fear of failure

At first, I thought that was the whole point. Playing with house money was the mindset I wanted to preserve. But the more I sat with it, the more incomplete that felt. The important point I came to is a bit less interesting and much less creative: I am incredibly grateful to my parents for giving me such an amazing start to my life. It is my job to take advantage of that opportunity and, hopefully, to do the same for my kids one day.

Going back in time, right before starting freshman year, I told my parents that my main goal of college was to drop out. The short summary of how I essentially achieved that goal is as follows: as a freshman, I got very involved with the entrepreneurship center while working on a project to help other students apply to internships. They put me at the center of their alumni and industry events, and at one of those events I met Toshit. From there, he became my mentor through the program, and we started working together. Eventually, he left his day job and we started working on Tollbit. Toshit and Olivia raised a bunch of money, and I got to take a leave of absence from school and work full time. I lived in New Hampshire, then in SF for a while as the company grew. If I wanted to, I could have never returned to school and never graduated. I had essentially dropped out.

What I was doing in that moment was exactly playing with house money. Not because Tollbit wasn't real, or because the work didn't matter, or because there was no risk. It was real, and it mattered a lot. But the downside was survivable. If it didn't work, I could go back to school. If I failed, my life would not be over (even though that's how most people choose to think in startups).

That is a hella privileged situation to be in. It feels cringe to say directly, but avoiding it would be worse. A lot of what I might have described as courage was also security. My parents gave me a life where I could take swings before I had fully earned the right to call myself brave for taking them.

And now, as I've learned and grown with Tollbit, I have the opportunity to continue the spirit of what it means to play and do great work. Not because my parents will always support me, or because I will be able to take zero-risk bets for the rest of my life. But because I have now learned how to support myself, and have seen myself do it once before.

There is a lazy version of playing with house money, where the lack of downside becomes an excuse not to care. That is not what I mean. The version I want to take with me is almost the opposite. I can choose harder games. I can take bigger risks. I can work with more joy and less fear. I can afford to be patient, but I don't want to be complacent.

So that is more accurate to what I want to take with me as I continue on my journey. Not the fantasy that I am fearless, or that I built everything myself, or that success does not matter. I want to take the gratitude seriously enough that it changes how I act. I have been given a real chance to play. The only unacceptable thing would be to sit at the table and play scared and not go all in.