The Image of Silicon Valley Tech Founders Is Being Reshaped
The image of Silicon Valley tech founders is undergoing a transformation. Sam Lessin, founder of Slow Ventures, a generalist venture capital firm, recently hosted an “Etiquette Finishing School” aimed at young Y Combinator founders and tech entrepreneurs. The goal was to help them learn how to dress and socialize confidently—and even how to overcome their fear of fish eggs.
“The image of Silicon Valley is changing from the one portrayed in ‘The Social Network,’” Lessin said during his opening speech on Wednesday. He was referring to the film about the founding of Facebook, which famously depicts Mark Zuckerberg as an awkward college student living in a gray hoodie.
The event took place in a private room behind a second-floor restaurant at the Four Seasons Hotel in downtown San Francisco, just blocks away from the offices of many new AI startups. Lessin emphasized in his introduction that technology doesn’t simply adopt itself; often, one must “push it into the world.” When you have a new and disruptive product that not everyone initially welcomes, charisma becomes the secret ingredient that opens doors.
Swag Bags and Stylish Lessons
About three dozen participants gathered around four round tables, which were adorned with beetroot tarts, watermelon poke, and truffle cheese balls. Each attendee received a swag bag containing on-the-go mouthwash, a hairbrush, a mini lint roller, and a $100 gift card for clothes shopping at Wilkes Bashford, a San Francisco-based retail store.
The lesson kicked off with a lineup of models dressed in clothing from Wilkes Bashford. The store, which counts former San Francisco mayor Willie Brown among its early clients, provided a stylish backdrop for the event.
Chris Deehan, a style advisor at Wilkes Bashford, dressed head-to-toe in shades of green, shared practical fashion tips. In relatively casual settings like offices or brunch gatherings, founders can get away with many choices—except clashing colors and flashy logos that “scream” for attention.
For more formal occasions—such as presentations to investors—Deehan advised men to wear a cashmere suit or, between November and February, a turtleneck sweater as an acceptable alternative to a collared shirt. Most importantly, he stressed that a tie is a must, or the suit should have a pocket square.
He also highlighted that “every type of suit has very specific buttoning rules.” To help attendees navigate potential confusion, Deehan offered, “If you’re not sure, send me a picture.”
Mastering the Art of Conversation
Silicon Valley’s reputation beyond the Bay Area isn’t always glowing. Sunil Rajaraman, founder of Hamlet, an AI company providing data solutions for developers and attorneys, reminded young tech founders that they are “not exactly beloved” across the country and that Silicon Valley is “not the center of the universe.”
“You need to be engaged beyond work, tech, and AI,” Rajaraman advised. He recommended that founders read more fiction to expand their imaginations and become more interesting conversationalists at social gatherings. “Many of you are making tech that will take other people’s jobs,” he pointed out, underscoring the importance of empathy and awareness.
Lessin added that knowing how to navigate different social settings without demanding excessive attention is crucial etiquette. “You need to be interesting beyond your company,” he said. “Approach situations with a low heart rate and think about what you can give instead of take. Showing up genuinely goes a long way.”
Handling Etiquette Challenges
The session also covered quirky but useful topics. When a vegetarian participant asked, “Does the extraction process hurt the fish?” it sparked a lighthearted moment. As a final tip, Lessin advised that when faced with a lengthy wine list in an unfamiliar language, guests should avoid rosé.
As the event wrapped up, participants received their certificates and began to leave. A software designer seated at my table remarked that while events like these are fun, founders whose businesses are rapidly scaling might be too busy on a random Wednesday afternoon to attend such gatherings.
Nevertheless, this “Etiquette Finishing School” offers a glimpse into the evolving culture of Silicon Valley—where style, charisma, and genuine social skills are becoming as important as coding prowess and technical innovation.
https://www.businessinsider.com/inside-silicon-valley-etiquette-school-for-young-tech-founders-2025-11
