From left, Meta chief executive Mark Zuckerberg, US President Donald Trump, first lady Melania Trump and Bill Gates attend a dinner for tech business leaders at the White House in September. Photo / Matt McClain, The Washington Post
Strolling into the Four Seasons Hotel, wearing a suit on a recent Wednesday, artificial intelligence start-up founder Nikolas Huebecker resembled a conventional business executive.
Making an effort with his appearance felt like “counterculture” in Silicon Valley, he said, an industry known for slobby tech bros, not sharp tailoring.
The 23-year-old was heading to an etiquette workshop for techies led by investors who would guide about 40 young founders on how to dress, make small talk and lick caviar off their bare hands - with the goal of boosting their chances of becoming the next tech billionaire.
Tech founders have traditionally eschewed business norms as they worked to upend the status quo, sticking with hoodies and jeans even as dorm-room dreams became billion-dollar corporations, and donning suits only when hauled before a court or Congress.
Scruffy grooming and unrefined social skills became hallmarks of the gifted entrepreneur laser-focused on changing the world.
However, the expectations of how a tech founder looks and acts, and the role models of Silicon Valley success are shifting as the industry gains power and influence.
Tech leaders are centre stage at the World Economic Forum in Davos, Switzerland, and United States President Donald Trump’s White House, where industry moguls such as Tesla chief executive Elon Musk and investor David Sacks, Trump’s AI and crypto tsar, have appeared in the dark suits of conventional business and government elites.
As Silicon Valley’s AI drive threatens to disrupt life and work across the US, founders are being counselled to balance raw technical prowess with people skills and smooth presentation.
A June survey from the Pew Research Centre found that 50% of Americans are more concerned than excited about the increased use of AI in everyday life, up from 37% in 2021.
Tech employers and investors “want the full package”, said Caroline Simard, dean of Northeastern University’s Silicon Valley campus.
That means people who have technical chops, and who “can collaborate, they’re good communicators … they have critical thinking,” she said.
Rising tech leaders are becoming more concerned with how they present themselves.
Victoria Hitchcock, a Bay Area style consultant who has helped tech clients who visited the White House this year, said people in the industry now request “major changes to their entire persona”.
In her 15 years working with tech clients, she has often had to point male founders towards simple areas to improve like personal grooming.
They will now proactively ask how to get rid of under-eye circles or for the best hair replacement programme, Hitchcock said.
Sam Lessin, one of the three investors who ran what they called the “Etiquette Finishing School” in San Francisco, told attendees that a bumbling but brilliant entrepreneur might have succeeded a decade ago, but today they needed to level up their social skills to be effective on a broader stage.
“There are going to be moments where, on the margin, it gets you the extra investor who’s like, ‘Okay, I can trust this person - this person’s projecting confidence,’” he said, before warning the mostly male, 20-something crowd that, to many people in society, “tech is no longer playful and cute”.
Lessin is a former Harvard University classmate of Mark Zuckerberg who became a Facebook vice-president after the company acquired his file-sharing start-up Drop.io in 2010.
He said he decided to hold this first edition of the workshop in part after seeing founders show up to pitch him looking like they had come straight from the gym and neglecting to take their coffee cups to the sink afterward.
Dressing too casually or abandoning dirty dishes communicates “a lack of care and respect for people and expectations that other people will pick up after you”, he said.
Now that AI innovations are potentially threatening people’s jobs, Lessin advised the assembled founders to be more humble and self-aware.
“You kind of need to be like, ‘I’m here and respectful,’ as opposed to ‘I am here and intentionally disrespectful,’” Lessin said.
The workshop began by tackling less fraught issues: How founders look and smell.
Each attendee received a gift bag containing a comb, 2-in-1 shampoo and conditioner, mouth wash, a lint roller and a discount card to Wilkes Bashford, a local high-end clothing boutique.
Representatives from the store introduced a parade of models who showed off looks - for men and women - appropriate for a big presentation or dinner or brunch with the boss.
No ripped or faded jeans here - and the only vest was a US$5000 suede number from Italian designer Brunello Cucinelli, a tech mogul favourite, not a US$200 Patagonia puffer.
Much of the wisdom was budget agnostic.
It’s okay to mix patterns, said Jeff Garelick, Wilkes Bashford’s director of stores, just make sure the pattern on a jacket is bigger than the one on your shirt.
While Huebecker and other workshop attendees had followed the invitation’s stipulation that they should dress in “San Francisco business formal” attire - the average tech founder needs wardrobe tips, according to those who advise and invest in young companies.
Hitchcock said she often fields calls from wives, executive assistants, and chiefs of staff requesting help for a male founder about to step onto a bigger stage, like an initial public offering, an invitation to Davos, or the White House.
“All of this is new to them, and it happens really fast,” Hitchcock said in a phone interview.
She’ll be candid about how someone can refine their appearance - whether that’s a tailored outfit, a stick of deodorant or taking care of those pesky nose or ear hairs - all with the goal of helping someone “look as smart from the outside as they are from the inside”.
The etiquette school could help people who might otherwise struggle to gain a foothold in the tech industry by “demystifying … this kind of invisible curriculum” to being an entrepreneur, said Simard.
“We have a lot of immigrants in Silicon Valley, a lot of international students, fantastic talent from all over the world,” she said.
“This idea of pitching a story, pitching yourself, having a unique personal brand” may not be familiar to all. Lessin’s firm is already planning a second session of Etiquette Finishing School for next year.
After the style tips, Lessin and his fellow hosts, venture capitalists Will Quist and Jack Raines, were joined by two social media influencers who gave advice on how to communicate.
Company pitches should be catchy and brief, they said. Ask questions rather than monologue. And above all, keep calm and connect like a human - especially when you’re selling automation.
After one brave founder pitched his start-up that helps online content creators connect with their audiences and strike deals with brands, Quist warned that diving too deeply into the nuance of your business “is definitely an etiquette no-no”.
Like supportive older brothers, Quist and Lessin advised it was better to devise a snappy description of a business and wait for the audience to ask more about it.
Sunil Rajaraman, the founder of Hamlet, an AI start-up that Lessin’s firm has invested in, urged founders to ask more questions of people they’re meeting in a business context - and ideally, about things beyond AI.
He accidentally demonstrated how challenging that can be in a tech crowd by asking one attendee the last work of fiction he had read - the founder couldn’t name one.
Sometimes connecting on a human level is a more effective strategy than pitching your business, noted Rajaraman, who had more success when he asked another founder where he got his distinctive light-blue cotton suit. The founder had helped sew suits for the brand.
Rajaraman was impressed. “This guy is interesting - you could ask him a million questions, and it’s just so easy,” he said, advising the founders to “just be a person”.
For all the tips on how to act and what to say, much of the guidance was also about not overthinking any one interaction or being too attached to a certain outcome.
After the founders were schooled in the importance of being humble, they enjoyed a moment of indulgence.
Geoffrey Chen, a founder and tech investor, gave instructions on how to consume caviar “bumps” from the back of the hand, saying attendees might encounter the delicacy at a business dinner or networking event.
Chen called caviar “the ultimate flex” and noted that it has been enjoyed by royalty for thousands of years, a nod to the power those in the room could attain if their start-ups take off.
Afterward, the founders collected certificates signifying they had mastered “the noble arts of polite conversation, graceful composure, and the increasingly rare practice of genuine human engagement”.
Then they walked out into the late-afternoon sun, to get back to work in an industry on track to make human engagement even scarcer.
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