“Be less scared of overconfidence” by benkuhn

When I was deciding whether to work for Wave, I got very hung up on the fact that my “total compensation” would be “lower.” The scare quotes are there because Wave and my previous employer, Theorem, were both early-stage startups that were paying me mostly in fake startup bucks equity. To figure out the total compensation, I tried to guess how much money the equity in each company was worth, with a thought process something like: Both of these companies have been invested in by reputable, top-tier venture capitalists. The market for for-profit investments is pretty efficient, and most people who think they can do better are being overconfident. Who am I, a lowly 22-year-old programmer, to disagree with reputable top-tier venture capitalists? I should defer to them about the valuations. So I valued the equity by taking the valuation each company's VCs had invested at, and multiplied it by the fraction of the company my shares represented. That number was higher for Theorem than for Wave. Seven years on, the Wave equity turned out to be… a lot more valuable. That raises the question: how dumb was my take? Was [...] --- First published: November 9th, 2026 Source: https://www.lesswrong.com/posts/5yC6qAPz3B9BGEKwL/be-less-scared-of-overconfidence-1 --- Narrated by TYPE III AUDIO .