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Reuben Stein
I joined Andreessen Horowitz in 2018 as a deal team analyst, straight out of Stanford. My job was to build financial models, conduct market research, and sit in partner meetings pretending I understood things that I absolutely did not understand. I was 22 years old, and I was in the room when decisions were made about deploying $50M into companies that didn't have revenue yet. It was simultaneously thrilling and terrifying.
After two years at a16z, I moved to Founders Fund as an associate. The cultural difference was enormous. a16z is a machine: systematic, process-driven, with a media and services platform that's basically a startup accelerator attached to a venture fund. Founders Fund is a contrarian bet shop: smaller team, less process, more conviction-driven. Both approaches work. Neither is obviously better. The fact that both can generate top-decile returns tells you a lot about how poorly understood venture capital is as an asset class.
At Founders Fund, I sourced deals, led diligence on several investments (two of which I'm genuinely proud of), and learned the craft of investing by watching people who are very good at it. I also learned the parts nobody talks about: the 60% of portfolio companies that will return zero, the board meetings where you have to tell a founder their company is dying, the LP reports where you explain why a $20M investment is now worth $3M.
I left VC in 2024 because I realized I was better at analyzing and explaining venture capital than at practicing it. The skill set for writing clearly about complex financial structures is different from the skill set for picking winning companies. I'm honest about that.
My writing covers VC mechanics with a level of specificity that makes some of my former colleagues uncomfortable. I write about how term sheets actually work, what "pro-rata rights" mean in practice, how valuation benchmarks shift, and why most fundraising advice from VCs on Twitter is self-serving. The piece that got the most attention was a breakdown of how a hypothetical $100M fund's returns are distributed across LPs, GPs, and management fees. A lot of founders told me it was the first time they understood where their investors' incentives actually lie.
I'm based in New York. I angel invest in a few companies a year with my own money, which keeps me honest. I play chess (badly), I run Central Park loops (slowly), and I'm learning to cook because Seamless is destroying my finances.
Experience
- Associate, Founders Fund
- Deal Team Analyst, Andreessen Horowitz
- BS Symbolic Systems, Stanford