I've befriended some of the most thoughtful, brilliant, curious, eccentric, and sincere people I've ever met in the tech industry. Many of my dearest friends are former coworkers. I've also encountered the most egocentric, delusional, irritating personalities imaginable in tech.
It is a mixed bag, like anything. But increasingly, the egomaniacs are not only taking center stage at the most influential tier of their respective companies - whether as 'founding engineers' or founders/CEOs/CTOs/ETCs or 'GTM engineers' - but they're also talking about themselves incessantly online.
That is not good for any of us.
This blog is long so here is the short version: the technology industry spent forty years accumulating a very specific kind of trust and mostly had boring motives, which made us appear trustworthy and largely benign. Over the last decade and change, its leadership discovered that this trust could be liquidated and converted into a different asset, attention, at what looked like a great exchange rate. The problem with liquidating an illiquid asset though is that you don't find out the real price until you try to buy it back. The Founder's Fund Mafia video is the most egregious example of this. If there are any founders out there considering doing their own version of the Mafia video, please don't. Instead, focus on publicizing your core nerd values: a love of learning, curiosity, an obsessive interest in your domain, and an admirable humility re: how you present yourself to others and talk about your accomplishments. This will probably catch on slower and be less viral, but it will pay off in the long-run once people 'turn against' tech founders as reality stars, which they eventually will.
The charming & visionary nerd trope
Ten years ago, the cultural idea of the technologist was still basically Jobs and Wozniak.
Jobs was flawed and everyone knew it, but it was all par for the course. He was aggressive in his ambition, uncompromising about even the most minute details of his company, and occasionally arrogant (not always, IMO. Sometimes you're just right.)
But people admired him anyway because the products he made worked well and were more tasteful/subtle/beautiful than any consumer electronic that had come before it. When Jobs was cruel, in the public's memory at least, he was cruel about kerning or whatever. The cruelty was bad, but it was presented as if he was cruel for our sake - for the sake of the customer. You could model him as a man who wanted the customer experience and the legacy of his business to be perfect, and that's exactly what we want our CEOs to do.
Then there was Woz, the patron saint of computer science: bashful, generous, humble, averse to the spotlight, and content with having a reasonable amount of wealth but not an absurd, evil-seeming amount of wealth. He gave away early Apple stock to colleagues because he felt weird about having so much and went back to teaching fifth grade. Woz was the proof of concept that you could be at the absolute center of the most important industrial transformation of the century and still not clamor to be famous for it. Instead, you could just do what you loved and make great money and share ideas about what you'd learned.
Together they told this story: the people building your future are, at worst, perfectionist jerks, and at best, gentle obsessives, and in either case their attention is mostly focused on their work, not at 'the world' with its glamorous sins.
Whether this was accurate or not is irrelevant. It is what the public thought. We trusted those people partly because they didn't seem to want our attention. They were nerds with money who mostly just wanted to be left to their projects, and it made sense that they were in charge of our digital experience.
We have strayed pretty far from that.
A short history of how tech leaders went from charming nerd to terrifying overlord
I'm going to massively simplify the transition from 'helpful, obsessive nerd who makes bank' to 'tech oligarch from hell who people joke is not human' into 3 phases.
Phase one (late 1970s to 2007): the founder as charismatic, mysterious byproduct. Founders appeared in media, but the coverage was mostly centered on what they were building. There was a mythology to them and they'd take photos in their garage surrounded by sparkling machinery, and they'd do keynotes and magazine interviews, but they were always orbiting around their products and companies vs. boastfully putting their own identities as rich/influential people center stage. We heard from them at regular intervals, but they were reasonably spaced apart so we didn't feel 'surrounded'. They never got too personal with us. Even Bill Gates, the era's villain, was on the cover of every magazine but we knew little about him beyond that he was competitive and well-read, which is true of all CEOs.
Phase two (2007 to 2015): the founder as parable. TED talks become a fun and popular way to learn new things and find interesting thinkers, The Social Network is a huge commercial hit, and the beginnings of 'founder' as an identity starts to sneak into the cultural mainstream. Starting a company becomes a viable career path thanks to YC, and the founder-as-protagonist narrative became the recruiting funnel for the entire industry. This phase was fine, because the parables were about innovation: products were still appended to founders, but now the founder was the central fixation culturally, and the product was proof that they deserved our admiration and curiosity.
Phase three (2015 to now): the tech industry as grift-adjacent. The digital commons of 2026 is defined by its grifters. So it's not purely tech's fault that its now seen as a sort of avenue for getting rich quick and amorally, even if you are an otherwise ordinary person. But it is our fault that many of our 'figureheads' are leaning way the hell in on this. Elon Musk is the most absurd example of this, but he almost doesn't count because he is in his own tier of ridiculously self-promotional and attention hungry.
But beyond Elon, we also have OpenAI acquiring TBPN, a founder-circuit podcast. An AI lab bought a talk show. That is a sign of something, and it's not something that falls in line with the tech moguls of yore. It's disconcertingly similar to Jeff Bezos buying The Washington Post.
Then there's Founders Fund, which installed its chief marketing officer as the editor-in-chief of his own media outlet and now, as we'll get to, a game show host. So, smartly, these companies and funds have learned that becoming media firms is a lot easier and more efficient than buying ads in existing media outfits, who are typically held back by something like journalistic integrity. The theory is correct short-term, but it ends in a vast humiliation of media. Our media outlets are already hanging on by the skinniest thread. With endlessly wealthy and powerful tech companies turning their 'big cyclops eye' onto sucking up share in the attention economy, I can only imagine the illusion of objectivity is going to deteriorate further.
And so, the founders attention has pivoted, in the eyes of the public, from their seemingly sacred work on nerd shit to an obviously shallow pursuit of power, money, and fame.
The Founders Fund Mafia video
Eight years ago, the Jobs/Woz image was wobbling. Five years ago the first long crack appeared at the base of tech's reputation. Fast forward to today and the facade has shattered into tiny pieces to reveal 10,000 snakes.
The snakes really got loose IMO with the Founders Fund Mafia Game video. This shit is fucking insane.
This is Peter Thiel's VC firm creating a slickly produced show in which Sam Altman, Palmer Luckey, Bryan Johnson, Moxie Marlinspike, Dylan Field, Ryan Petersen and a rotating bench of the firm's favorite 'characters' play a party game about deception!!!!!! WHY WOULD YOU DO THAT!!!!
Even if it goes well short term, you are setting yourself up to be a punchline down the road. If any of these guys are involved in a Cambridge Analytica-level scandal in the future, people are going to point to this and be like 'see, he's a good liar', or 'he was hiding how good he is at deception here.' This is so dumb it's blowing my mind.
It's hosted by Mike Solana of Pirate Wires. The debut episode is titled "Can Tech Legends Find the Liar?" They filmed it at Tosca Cafe, the same San Francisco bar where the PayPal Mafia posed for their famous 2007 gangster photo shoot, so the self-mythologizing is out of control.
Obviously, commenters called the cast a "nightmare blunt rotation."
One critic revealed what the format is for: reality TV is a 30 yr old laundering technology, they said. It takes someone you'd keep at arm's length and makes him a recurring guest in your living room until the strangeness wears off. Ozzy bit the head off a bat so MTV made him the lovable bumbling dad who couldn't work the remote, and he became a lot more likeable. If the video editor and PR team can make enough smart cuts in post, everybody comes off pretty damn charming.
Applied to this cast, this strategy becomes undeniably sinister. One of them runs the most consequential AI lab on the planet and a side project to biometrically enroll the species. One of them builds autonomous weapons for the Pentagon. Between them, the principals hold the capital, the weapons contracts, and the line to the White House, and the show's function is to make you fond of them despite all this. (The shrewdest casting decision is Moxie Marlinspike, who doesn't have our future in his hands as explicitly, and is one of the most respected privacy engineers around. His presence at the table makes this all seem above-board. He is the equivalent of the beloved indie band on the festival poster, and the fact that the format needs him there tells you the producers understand exactly what their true goal is with this content.)
It is a charm offensive, in the technical sense: an offensive, conducted with charm. And even if it racks up some views and convinces a few people who already ride for Sama that tech CEOs are cool, it will disturb the rest, at least in hindsight.
You can still be a public founder, just remember who you are
There is no reason founders should disappear from public life. There are too many advantages to building in public to ignore it.
We just need to be a little smarter about how we present founders and tech workers in general to the public. It's extremely simple to do it the right way. Just remember who you are: a smart kid, often alone, tinkering around with hardware or on your computer, trying to understand how things work and see what you can make yourself.
What I'd recommend for founders and their top-level teams is:
- Be transparent about your goals. Launching a reality TV show as if your aim is to entertain and help people 'get to know' your partners and portfolio founders is deceptive and creepy. You're trying to humanize people who have fucked their reputations in a covert, dopamine-laced way.
- So if your goal is to promote some product or talk about yourself, just keep it a buck fifty. See Jason Fried's social presence for proof of what this looks like when you go about it with some semblance of humility and authenticity. He is fine and not a clown show. He and DH Hansson have retained the nerd-dom that made tech interesting/fun/curiosity-driven/charming for an audience with a certain taste in the first place. With them, it at least 'feels' like what you see is what you get. That does wonders for your reputation.
- Keep your ego as balanced as possible. Obviously, being a founder is aspirational, there are tons of material benefits, people think you are cool, and you have probably done interesting or admirable things. But just try to be chill about it if possible. Resist the urge to flex incessantly. Even though YouTubers do it, and even though it does result in impressions and views and likes from people who want to work at your company or be like you, it is cheap, flimsy attention that doesn't have a ton of staying power. The harder, slower work of winning admiration and attention through the strength of your product decisions, business acumen, and customer value is worth the effort.
Founder brands are necessary now. But they do not have to be as cringe and occasionally disturbing as they've become. Rather than projecting an obsession with wealth and power, trustworthy founders must instead focus carefully on projecting an obsession with core nerd values: enthusiasm about niche interests, obsession with technical pursuits, a love of learning and curiosity, and a deep-down humility and skepticism of the spotlight.