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

A pattern is emerging among people who’ve already made it big. They’re rolling up their sleeves again, seemingly out of fear of missing AI’s defining moment and, presumably, the irresistible allure of making even more money — potentially a lot more.

Tom Blomfield, who co-founded GoCardless and Monzo before spending 4.5 years mentoring founders as a Y Combinator Group Partner, announced on Monday that he is taking a leave of absence to join Anthropic’s compute team — not as an executive, but as a member of technical staff.

He’s not alone in making that kind of move. Instagram co-founder Mike Krieger joined Anthropic as Chief Product Officer in 2024, and Andrej Karpathy, a founding member of OpenAI who went on to lead AI at Tesla and start his own company, Eureka Labs, joined Anthropic’s pre-training team in May, framing the decision almost identically to Blomfield’s, writing that “the next few years at the frontier of LLMs will be especially formative.”

Not everyone is joining someone else’s lab. Chamath Palihapitiya, the “SPAC King” who has mostly stuck to boardrooms and all things “All In” since leaving Facebook in 2011, just took his first full-time operating role in over a decade as CEO of 8090 Labs, his enterprise AI coding startup, which he announced a couple of weeks ago along with a $135 million Series A led by Salesforce Ventures. Wrote Palihapitiya on X, “I am convinced that what we are building now is even more important, so there was no decision to make except to be all in.”

Similarly, Eric Wu, who ran Opendoor for a decade before stepping back in 2023, recently launched NavigateAI, an AI “copilot” for construction workers, with $25 million in seed funding. Wu told me directly on a recent call about his decision to dive into an AI startup, “I knew if I looked back in 10 years and didn’t do something related to it, I would probably regret that.”

The clearest sign of how keen people who’ve already “made it” are to work on what they view as the still-early-innings of AI might be the job title itself. “Member of technical staff” is the deliberately flat, non-hierarchical label that Anthropic and OpenAI use for nearly everyone on their technical teams, regardless of seniority. It’s the same title Blomfield is taking.

It’s also the title that Peter Bailis took this March, just months after becoming Workday’s CTO, a role overseeing AI strategy across an $8 billion-revenue business. Bailis lasted less than a year before trading it for a spot at Anthropic.