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Already rich, already successful, why the last wave of tech winners is grinding again
A number of already-wealthy, already-accomplished tech figures are returning to hands-on operating or engineering roles, driven by a fear of missing what they see as the defining moment of the AI era and the prospect of even greater financial rewards. The trend spans people rejoining others' companies in junior-sounding technical positions as well as veteran founders launching new AI ventures of their own, suggesting that AI's perceived scale of opportunity is drawing back people who had already stepped away from day-to-day work.
Examples include Tom Blomfield, co-founder of GoCardless and Monzo, who is taking leave from Y Combinator to join Anthropic's compute team as a "member of technical staff" — the same deliberately non-hierarchical title used by Andrej Karpathy, who joined Anthropic's pre-training team in May, and by Peter Bailis, who left his role as Workday's CTO for Anthropic after less than a year. Instagram co-founder Mike Krieger became Anthropic's Chief Product Officer in 2024. Others are building their own companies: Chamath Palihapitiya has taken his first full-time operating role in over a decade as CEO of 8090 Labs, an enterprise AI coding startup that raised a $135 million Series A led by Salesforce Ventures, while former Opendoor chief executive Eric Wu has launched NavigateAI, an AI "copilot" for construction workers, backed by $25 million in seed funding.
In short
- Wealthy tech veterans are returning to hands-on AI roles, fearing they'll miss out.
- Tom Blomfield leaves Y Combinator to join Anthropic's compute team.
- Chamath Palihapitiya and Eric Wu are launching new AI startups.
Steelman: both sides, in good faith
The strongest fair case each way — we don't pick a winner.
The case for
AI genuinely represents a transformative historical moment requiring the best available talent. These accomplished individuals bring valuable expertise that could meaningfully advance crucial development. Choosing to apply one's talents where they matter most is rational stewardship of one's abilities, and wanting to be part of shaping history's most consequential technology is understandable and legitimate.
The case against
The pattern reveals how wealth and status can create an insatiable drive for more, even among the already-enormously successful. Rather than finding meaning in their accomplishments or addressing pressing problems elsewhere, these figures chase the latest opportunity, seemingly driven by FOMO and fear of irrelevance. This concentrates opportunity within a privileged elite and raises uncomfortable questions about whether it serves society's broader needs.
Explained simply
Artificial intelligence (AI) is software that can perform tasks such as writing, analysing information or helping create computer code. Companies are investing heavily in it, and some founders and executives see it as a major shift that could create new businesses and large financial returns.
The people involved have varied backgrounds: some founded or led established technology companies, while others have worked in research or investment. Their new roles range from technical jobs at AI firms such as Anthropic to starting companies that apply AI to business software or construction.
Their moves matter because they show how the expectation of rapid change is drawing experienced people back into day-to-day work. They also illustrate how AI investment is spreading across both large technology companies and newer ventures.