It was the most un-San Francisco scene imaginable: Thirty of the city’s young founders arriving early in tailored suits and elegant black dresses, not a hoodie in sight.
Under a glass chandelier, the mostly male founders mingled in a wood-paneled room straight out of an East Coast country club, eager to learn the art of a proper handshake and the classy way to do a caviar bump.
“It’s a new world,” Sam Lessin, general partner at Slow Ventures, told attendees in the decisively Old World setting. “All of a sudden, the Mark Zuckerberg of ‘The Social Network’ parody movie is actually pretty cultured and knows how to be in a bunch of different rooms.”
The founders were gathered at the Four Seasons in San Francisco’s financial district for Slow Ventures’ “Etiquette Finishing School,” a three-hour seminar to equip them with basic manners and refined tastes. Lessin, an investor who was an early employee at Facebook, decided he needed to do something about the hundreds of young founders in San Francisco who can’t write an email or put together an appropriate fit.
“You have a lot of young founders who dropped out of school at 12, and they spend all their time talking to Bob in accounting about what to build,” Lessin said on the podcast (opens in new tab) he hosts with his wife, The Information CEO Jessica Lessin, and fellow married investors Brit and Dave Morin. “They don’t really understand anything about etiquette or how to interact in the world.”
Lessin, who exudes eccentric professor energy, admits that the etiquette school started as kind of a joke. But he sent his deputy Jack Raines to Y Combinator’s Demo Day in September to gauge interest and found that besides optimizing their supplement stack, the AI kids were actually interested in learning which wine to pair with seafood and how to make eye contact during a conversation.
Not everyone was on board with the idea. Garry Tan, CEO of Y Combinator, the same startup incubator where Lessin was farming for prospects, warned founders on an internal forum not to attend.
“You don’t need finishing school. You need to build something great, make your users happy, and have craftsmanship. We’re just here to make stuff. We’re not here to impress anyone by how fancy our shit is,” Tan wrote on X (opens in new tab).
“The truly wealthy are wealthy in meaningful relationships and the outcome of actually making something people want, not bullshit appearances or impressing people or running power moves or playing zero sum dominance games,” he added.
Still, the class was free, and so was the wine. A few hundred founders applied for Etiquette Finishing School, and about 50 were accepted. Not everyone showed up.
One founder, who wished to remain anonymous, said he was there to learn to be “less feral.” A meeting with a Japanese conglomerate made him realize he had no idea how to be a “functioning adult in polite society.”
Marie Paoli, cofounder of the AI assistant startup Mellow, said she was about to start fundraising and hoped the session would help her sharpen her ability to charm investors. “And there’s caviar. I absolutely love caviar,” she added.
When the room was called to order, the crowd took their seats at round tables draped in white linens. Each place was set with a gift bag containing a travel-size lint roller, mouthwash, and dental floss.
In his opening remarks, Lessin stressed that etiquette school wasn’t about memorizing rules but about moving through the world with confidence. Then he demonstrated the perfect handshake. Always look them in the eye. Strong, firm grip. Slight smile.
On cue, the fashion show started. Like a scene out of Silicon Valley “Zoolander,” six models, outfitted in Brunello Cucinelli, Bottega Veneta, and Huishan Zhang, showcased looks for the office, brunch, board presentations, and cocktail parties.
Many of the founders’ mouths were agape when they were asked to consider ditching their Patagonia vests for a suede Cucinelli number that retails for nearly $5,000.
The rest of the afternoon could best be described as a crash course on being a human. There were sessions about public speaking, projecting charisma as a leader, and maintaining office decorum once you start hiring employees. During the lessons, servers delivered to each table three-tier stands stacked with beet tartare, compressed watermelon poke, and smoked salmon gougères.
Between bites, founders jotted down a steady stream of advice in notebooks and on napkins. A few tips: If an invitation says black-tie optional, choose black tie; in conversation, ask more questions and talk less; and whatever you do, don’t roll up to the Rosewood in a flashy car (gauche).
One speaker earnestly suggested good conversation starters, including “What show are you currently streaming on Netflix?” and “What’s the last fiction book you read?” The founder he asked simply could not remember.
Throughout the event, Lessin doubled down on etiquette’s importance in Silicon Valley. A few decades ago, he said, the region was a backwater where the sight of an unshowered techie wearing a rumpled T-shirt to work was slightly endearing. But those days are over.
“Know the codes,” Lessin said. “Tech is no longer playful and cute. It’s taking people’s jobs and changing environments. Everyone’s threatened by it, which means you need to be like, ‘I’m here and respectful,’ as opposed to ‘I’m here and intentionally disrespectful.’”
The crowd nodded intently, before the closing session: a lesson about caviar and wine.
Each table was brought a tin of caviar on ice and blinis. Geoffrey Chen of Caviar House & Prunier guided the founders in a posh accent through how to take a bump of the salt-cured sturgeon eggs. He advised them to use a mother-of-pearl spoon to avoid ruining the taste with metal and offered a rule to live by: Always order Champagne, never rosé.
Despite the pomp and circumstance, the founders — all of whom made steady eye contact and were perfectly polite — said the most valuable lessons were the bits of wisdom Lessin sprinkled throughout the afternoon.
“I liked what he said about taking a breath and lowering your blood pressure before you enter a room,” Paoli said. “I’m definitely going to remember that when I’m meeting with investors.”
“The highlight for me was what Sam said about having an abundance mindset. There’s always more opportunities around the corner,” said Maxim Sindall, a Toronto-based founder who had traveled to San Francisco to attend etiquette school.
Peretz Partensky, the founder of ImmuneBridge, said he’d recommend future etiquette school events to his peers. (Yes, there will be more, and Lessin said he is considering writing a book called “Modern Etiquette in Silicon Valley”). But the absurdity of the occasion wasn’t lost on him.
“This should definitely be an episode of ‘Silicon Valley,’” said Partensky. “Reboot the show!”