Inside the Silicon Valley etiquette class teaching founders charisma, couture, and caviar confidence

• A Silicon Valley VC is teaching founders how to dress and socialize.
• Founders at a recent etiquette class were told they're "not exactly beloved" nationwide.
• The caviar drew many curious questions from participants who had never tried it.

The image of Silicon Valley tech founders is being reshaped.

So says Sam Lessin, founder of Slow Ventures, a generalist venture capital firm, who hosted an "Etiquette Finishing School" for young Y Combinator founders and tech entrepreneurs to learn how to dress and socialize, as well as 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 in his opening speech on Wednesday, referring to the film about the founding of Facebook that portrays Mark Zuckerberg as an awkward college student who lives in a gray hoodie.

The event was held 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 said in his introduction that technology doesn't just adopt itself — one often has to "push it into the world." And when you have a new and disruptive product that not everyone will welcome, charisma is the secret ingredient that opens doors.

Spread across four round tables populated with beetroot tarts, watermelon poke, and truffle cheese balls, three dozen or so participants 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.

The event was divided into three sections: styling tips for work outfits, a panel on how to engage in good conversation, and — last but not least — a caviar tasting session.

Tips on working in style

The lesson started with a lineup of models dressed in clothing from Wilkes Bashford, an SF-based retail store, which had Willie Brown, the city's former mayor, as one of its first clients back in the 1960s.

Chris Deehan, a style advisor at Wilkes Bashford, who was dressed in varying shades of green from head to toe, said that in relatively casual settings like the office or a brunch gathering, a founder could get away with a lot — except for clashing colors and flashy logos that "scream" at onlookers.

On more formal occasions, however, such as a presentation to investors, Deeshan recommended that men wear a cashmere suit and suggested a turtleneck sweater as an acceptable alternative to a collared shirt between November and February.

Most importantly, said Deeshan, you must either wear a tie or the suit must have a pocket square.

"Every type of suit has very specific buttoning rules," said Deeshan to some befuddled faces. "If you're not sure, send me a picture."

How to make good conversation

Believe it or not, Silicon Valley is aware that it may not be as popular outside the Bay Area tech circle.

Sunil Rajaraman, founder of Hamlet, an AI company that collects data for developers and attorneys, told 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," said Rajaraman, who recommended that founders read more fiction to expand their imagination and be more entertaining to talk to at a party. "Many of you are making tech that will take other people's jobs."

Lessin said that understanding how to approach different rooms and not overly demanding attention in every social setting is the key to etiquette.

"You need to be interesting beyond your company," said Lessin. "Approach situations with a low heart rate and think about what you can give instead of take. Showing up genuinely goes a long way."

The caviar tasting

The food-tasting portion arrived just in time, as the plates with small appetizers grew emptier. Once tiny cans of caviar arrived on silver platters with mother-of-pearl spoons, the audience was abuzz with questions.

"Does the extraction process hurt the fish?" asked one vegetarian participant.

"How much should we chew the caviar, exactly?" asked someone from another table.

Yours truly had never gone out of her way to try the slightly mushy, olive colored, granular delicacy that Geoffrey Chen, an advisor with the Caviar House & Prunier Group, said is almost as expensive as cocaine, but after consuming a spoonful of it on top of a blini, it became clear that it's not exactly about how it tastes.

"It is a food for a celebratory occasion," said Chen, recommending that savory foods like caviar are complemented best with Champagne, while rich foods like oysters should be paired with sake or chardonnay.

And as the final takeaway, in the face of a menu with a long wine list in a language you don't understand, he said, choose anything but a rosé.

As participants got up to receive their certificates and began to file out, a software designer I had met at my table told me that these events are great fun, but founders whose businesses are really taking off would be far too busy on a random Wednesday afternoon to attend the Four Seasons.

"Well, all this is important," he said of etiquette, "But you can afford to be a little crazy if you're a genius and have a really great product — like Elon Musk!"

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