Sahil seemed to join the tech startup sphere around the time I did, back in ~2009 when he was making iPhone apps. I remember beta-testing one of his apps on my first iPhone at the age of 17, I can't imagine he was much older.
He's always been a hustler, and I don't mean that in an entirely negative or positive way. He exemplifies startup hustle culture in a way that I sometimes envy for his ability to move quickly and churn out new things, but that comes at a cost. The cost is integrity, morals, resolution, whatever you want to call it. He's a mercenary with no particular loyalty.
Gumroad has a scandal every year or two, and they're always based on jumping on the latest bandwagon. The company itself was formed in the creator hype phase that birthed Patreon and Kickstarter, it has seemingly had a full reset (i.e. layoffs back to just Sahil) twice, once when they failed to make it big, once again when layoffs were cool. That he is on the LLM hype, in a hype-driven way rather than an actually effective way, is no surprise. And lastly that he has "open-sourced" the codebase again comes across as a cynical move rather than one done for the right reasons.
All this is to say that Sahil joining DOGE is entirely on brand, both in the sense of DOGE being the epitome of the worst of startup hustle culture (we can solve every problem from first principles with some shitty code, screw actual experience!), and in the sense that this is the next bandwagon that will make him cool. Like Zuckerberg, I think Sahil is just another insecure nerd who prioritises addressing that insecurity over standing up for themselves and their beliefs.
I also started following Sahil when I joined the startup world. His name seemed to be all over Twitter and HN. It was through him that I also started following Austen Allred. Sahil was the first guest on Austen’s podcast and the two of them showed up in a lot of articles together.
Both of them seemed like startup superheroes at the time. I remember being amazed when startup sphere heroes would Tweet praise about Sahil or when Paul Graham wrote one of his rare articles defending Austen Allred, of all topics.
It was a learning experience for me to watch as Gumroad laid off all of the engineers who built the site and then investors gifted the company to Sahil, leaving him to operate it as a profitable enterprise for himself while the early engineers saw their equity wiped out (though supposedly he helped some of them to unspecified degrees). It was further eye opening to see the collapse of Austen Allred’s Lambda School after watching Paul Graham and others sing its praises in ways that were at odds of the realities of their students.
I suppose it was all a valuable lesson in learning how to separate the hustler marketing from the reality.
I, too, have followed with interest as Sahil jumped from trend to trend. Pivoting hard into LLM assistants (including the flash-in-the-pan Devin AI coding tool which disappeared as quickly as it entered the scene) and now into DOGE isn’t too surprising. Meanwhile Austen Allred is off on a new pseudo bootcamp, pumping his Gauntlet AI bootcamp via Tweets about how their students are creating SaaS companies in weeks or something, nearly repeating the same marketing he was doing years ago about his bootcamp grads landing high paying jobs (including the famous sample size of 1 debacle).
Austen also swung hard right on his Tweets to the point of hurling expletives at people critical of Trump’s policies lately, which finally prompted me to give up on my curiousity follow. Seeing Sahil lean hard into DOGE is equally on brand.
It’s like these guys have such a deep drive to align with tech industry trends that they sense them coming, go all-in, and do the most status-seeking moves they can make to be seen as on top of those trends. I also don’t know what to say about it other than it’s been interesting to observe.
He's always been a hustler, and I don't mean that in an entirely negative or positive way. He exemplifies startup hustle culture in a way that I sometimes envy for his ability to move quickly and churn out new things, but that comes at a cost. The cost is integrity, morals, resolution, whatever you want to call it. He's a mercenary with no particular loyalty.
Gumroad has a scandal every year or two, and they're always based on jumping on the latest bandwagon. The company itself was formed in the creator hype phase that birthed Patreon and Kickstarter, it has seemingly had a full reset (i.e. layoffs back to just Sahil) twice, once when they failed to make it big, once again when layoffs were cool. That he is on the LLM hype, in a hype-driven way rather than an actually effective way, is no surprise. And lastly that he has "open-sourced" the codebase again comes across as a cynical move rather than one done for the right reasons.
All this is to say that Sahil joining DOGE is entirely on brand, both in the sense of DOGE being the epitome of the worst of startup hustle culture (we can solve every problem from first principles with some shitty code, screw actual experience!), and in the sense that this is the next bandwagon that will make him cool. Like Zuckerberg, I think Sahil is just another insecure nerd who prioritises addressing that insecurity over standing up for themselves and their beliefs.