TLDR · 2026-04-23 · 53 min
Most founders stay in the CEO seat too long. Tony Jamous didn't. In this episode of TLDR, I spoke with Tony (founder of Oyster) and Hadi (new CEO) about stepping back when the company needs something different. Not because the company was failing. Because it needed something different to scale. Tony asked himself: "What needs to happen for Oyster to reach $10 billion?" The answer? A different CEO. That realization took months to accept. Oyster was his baby. The mission - anyone, anywhere can access great jobs - was deeply personal. But 360 feedback from his team made the gap clear. They needed someone closer to operations. Someone built to scale multi-billion dollar companies. Someone with different strengths for the next chapter. So Tony went to the board and said we need to make a change. The process: Hired top-tier executive search. Interviewed 40+ candidates globally. Required a case study: "How would you make Oyster more successful than anyone imagined?" Let the board vote without him voting. Hadi got 100% of votes. Clear #1. But the hire was just the beginning.
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