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

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.