The Silicon Valley Founder Meat Grinder
Ranked #1 on Hacker News with 47 points and 11 comments.
A few years I met a guy, let’s call him Jim, who was trying to break in tech by going to a bootcamp to become a developer. In the meantime, he worked as a bartender and had been living off the support of his girlfriend, who was from a well-off family and Jim was her trophy boyfriend. He approached me because he was really into startups and wanted to become a tech entrepreneur, and make the big bucks. His motivations notwithstanding, he was currently struggling with a routing issue in his food delivery app project, and asked for my help, which indicated to me that Jim is years, probably decades away from fulfilling his billion dollar startup dream. After helping him debug it, we exchanged contacts and kept in touch.
Despite his current state of affairs, he seemed to have potential: he was ambitious, hungry, determined and hard-working. And, perhaps more importantly, he was tall, looked exotic, had a pronounced English accent, and was quite athletic. Jim had charisma. He could make people listen to him.
A small nudge in my network got him a job at a startup that got acquired a year later by a Fortune 100, and just like that, Jim got into the 6 figure territory. It was crazy seeing him advance at such pace.
Things took a turn when Jim’s kryptonite became exposed once he started making money: He lost focus and became reckless. He bought some fancy tree slice table for 10k bucks, got into brewing beer, got a dog, a cat, and overall, went completely over himself financially. A few months post-acquisition, he got fired for an allegedly silly reason, but my intuition is that he was coasting hard and couldn’t focus at all because of home office and lifestyle creep.
While collecting unemployment money and also being busy taking delivery of his new sports car, Jim complained to me that the place where we were based in was “too small for his dreams”. He was now setting his sights on the Silicon Valley. The promised land. At that point, I had completely written Jim off. He showed me his true colors, and I was sure that his lavish lifestyle will sink him lower than his bootcamp days.
I was horribly wrong. He was still on great terms with his former bosses, the now-acquired startup founders, who were still holding positions at the acquiring company he had been freshly fired from, and they connected him to somebody in the US who had been working on some legal startup. And, lo and behold, Jim and that guy applied to YC and got in. My guy was now flying to San Francisco and properly gunning it.