Already rich, already successful, why the last wave of tech winners is grinding again

A pattern is emerging among people who have already made it big. They’re rolling up their sleeves again, seemingly for fear of missing AI’s defining moment and, presumably, the irresistible lure of making even more money – possibly a lot more.

Tom Blomfield, co-founder of GoCardless and Monzo before mentoring founders for 4.5 years as a Y Combinator Group Partner, announced on Monday that he is taking a leave of absence to join Anthropic’s computing team – not as a manager, but as a member of the technical staff.

He is not the only one to make such a move. Instagram co-founder Mike Krieger joined Anthropic in 2024 as Chief Product Officer, and Andrej Karpathy, one of OpenAI’s founders who later led AI at Tesla and founded his own company, Eureka Labs, joined Anthropic’s pre-training team in May. The decision came virtually identical to Blomfield’s, writing that “the coming years will be at the frontier of LLMs especially formative.”

Not everyone joins someone else’s lab. Chamath Palihapitiya, the ‘SPAC king’ who has mostly stuck to boardrooms and the like’All-inSince leaving Facebook in 2011, he has just taken on his first full-time operations role in more than a decade as CEO of 8090 Labs, his AI coding startup for businesses, which he announced a few weeks ago along with a $135 million Series A led by Salesforce Ventures. Palihapitiya wrote on even more importantso there was no other option but to go all in.”

Similarly, Eric Wu, who led Opendoor for a decade before stepping back in 2023, says: recently launched NavigateAI, an AI “co-pilot” for construction workers, with $25 million in seed funding. Wu recently told me during a phone call about his decision to dive into an AI startup: “I knew that if I looked back in 10 years and didn’t do anything with it, I would probably regret it.”

The clearest sign of how eager people who have already “made it” are to work on what they consider the still-early introduction of AI might be the job title itself. “Member of the technical staff” is the deliberately flat, non-hierarchical label that Anthropic and OpenAI use for almost everyone on their technical teams, regardless of seniority. It is the same title that Blomfield assumes.

It’s also the title Peter Bailis took on in March, just months after becoming CTO of Workday, a role that oversaw the AI ​​strategy of an $8 billion company. Bailis lasted less than a year earlier trading for a spot at Anthropic.