Confessions of a Compromised Capitalist

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I don't tell this to many people...<br>I was once homeless. Free. Riding across vast stretches of the United States with nothing more than a bicycle, a guitar, and a sleeping bag.<br>Careless, naive, and rejecting anything remotely adjacent to working a 9-5 job, or living as a functional, productive member of society. I simply wanted to experience ultimate freedom and opt out of capitalism.

I even went so far as to promise my friends and family that I'd never ever in a million years be a rich man. I'd never let that happen. I'd sooner play music for money on the street and eat stale bagels from dumpsters than become another cog in the machine.<br>I even remember people's perception of me changing depending on my perceived economic output. When you're on the margins of society and not making or spending money, good luck even getting a business to let you use the bathroom in the downtown of a busy city.<br>I truly believed that being rich was a sin, and I truly believed that humanity overcomplicated life with our side hustles, and purchases, and obsessions with status.<br>Well... If you're reading this now...<br>Spoiler Alert: Life is completely unpredictable, and the things we do and say when we are young rarely take into account the wisdom and experience and changes in philosophy that we find as we age, meet new people, and venture off to new places.<br>If you're reading this now, you probably don't see this adding up.<br>How did a homeless troubadour on a bicycle end up becoming a venture capitalist, seemingly betraying every virtue and strongly held belief he once had along the way?<br>The short answer is that I was always investment-minded, having studied it at a young age, going for weekly breakfast meetups with my Uncle, who had seen promise in me for some strange reason. With the right guidance and ample time spent ideating and iterating over scrambled eggs, delicious pancakes, and crispy, maple syrup-soaked bacon every Saturday morning, I began to fall in love with the idea of investing and owning small pieces of big companies.<br>I was potentially always a miniature VC at heart, yet I found myself aimlessly wandering from job to job, place to place, lifestyle to lifestyle without truly understanding that I could make a life and career out of that.<br>Fast forward a few decades, and I now work in the investment space, helping to back, invest in, build, advise, incubate, and create tech startups.<br>I sit across the table from brilliant founders, trying to decide if they have ideas worth backing.<br>I attend meetings and dinners and events with people who have made their peace with a version of the world I'm not sure I believe in.<br>I rub elbows with people who have obscene amounts of money and influence.<br>And I can't help but feel like a complete hypocrite. I can't shake the feeling that my younger self would be both proud and disappointed with how I've turned out. Maybe he wouldn't even be able to recognize me altogether.

Some days I feel like a traitor to the cause. Conveniently forgetting my old oaths to fight for justice, equity, and dignity for all. Other days, I tell myself I'm a good guy on the inside. A Trojan Horse affecting change from the only place it can truly happen. What's more powerful than being in the right place at the right time with the right connections and resources?<br>It may be abundantly clear now as you read this (if you are still indeed reading this!), but I have not resolved this conflict. Not even a little bit. It's an infinite struggle happening in my head, burning up memory usage while I tick away and try to build my own VC fund, Arcanum Ventures, with one of my childhood friends, Sasha Asheghi.<br>I've been marinating over writing both this "confession" and this newsletter/blog for a long time, trying to figure out how to broach the subject, what to write about, and how to direct my fury, rage, passion, sadness, and conflict.<br>How to channel it into doing something about the injustice I see every day in our industry?<br>I've been inside this industry long enough to see how it works when nobody is performing. Not the version that gets written up in TechCrunch. The other version.<br>The one where founders get managed rather than supported the moment the power dynamic shifts. Where decisions that will affect thousands of people get made in forty minutes because the numbers work. Where exhaustion gets mistaken for commitment and sociopathy gets mistaken for vision.<br>I remember a partner making a reference call on a founder, getting back an honest and unflattering answer from someone who had nothing to gain from being honest, thanking them for their time, and funding the round two weeks later anyway. The founder tested well in the room. That was enough.<br>I'm not naming anyone. I don't need to. If you've spent any time in this world, you already know exactly what I'm describing...<br>And if you haven't, you deserve to know it exists .<br>I could have left it all behind...