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.
What followed was a flurry of social media posts and updates, each crazier from the previous one - photos with Sam Altman, bold statements with hundreds of views and likes, presentations, interviews, big valuation numbers.
His startup failed, but that’s okay, that’s the norm! And he was in San Francisco anyway, so he was in the big leagues now. Jim quickly joined another startup as Head of Engineering (for perspective, it happened 3 years after he completed the bootcamp), had a short stint there, founded another startup with an ex-Big Tech software engineer as a founder, but that failed too, so then he founded another startup…and then things started to get weird: His posting became daily, and it was complete utter AI slop. These were sprinkled with ALL CAPS POSTS that were peeking out from the polished slop timeline. These were unintelligible blather, which I’m certain he wrote by himself, presumably under the influence of some strong chemicals.
And then, silence.
Months passed, and I forgot about Jim since he simply evaporated from the internet. Around a year later I had a catch-up with a common acquaintance of ours who shared with me his dismay over Jim’s debauchery: Jim had participated in drug-fueled “founder parties”, group orgies and all other crazy experiences in San Francisco. This naturally led to the breakup with his fiancée and a nervous breakdown. Money went dry, and he begged our common acquaintance for money for a plane ticket so that he can get back home. Since then, he had disappeared from the face of the Earth. Nobody knew his whereabouts, or if he was alive at all. My guess is that he went back to bartending, and found another rich girlfriend to feed him.
Even though my writing might come off as pejorative towards Jim, I genuinely admire his ways. In the span of just a few years, he went from nobody to a tech founder hotshot. Before Jim, I always believed that I have what it takes to be a tech entrepreneur - I took risks, started from zero, built companies, moved countries…but I also played safe - I chose to stay in school, to help my family, and to be more level-headed. While Jim’s trajectory was an inverted parabola, mine has been mostly linear. I moved upwards slowly, but steadily.
This all reads like fiction, but you have to trust me on this - Jim is a real person. And I don’t believe his story is a precedent. I suppose everyone who’s deeper into the startup community in SV know several Jims, but this particular Jim was my first, and it made an impression on me. It made me realize that the Silicon Valley has an established pipeline for such people. Thousands of Jims go through the meat grinder. A few make it and get celebrated, most get squished and thrown away. After all, it turns out that steady is indeed, in 99.9% of the cases, fast.