
Skydeck Fail Better
May 5, 2023
Join Ray McGuire, a veteran Wall Street banker, as he shares humbling stories of early career blunders, emphasizing authenticity. Former Greek Prime Minister Antonis Samaras reflects on political integrity amidst setbacks during a financial crisis. Depelsha Thomas-McGruder, a leader at the Ford Foundation, discusses challenges launching MTV Tr3s and its cultural impact. Reshma Kewalramani, CEO of Vertex Pharmaceuticals, highlights the critical importance of hiring exceptional talent to shape a thriving company culture.
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Hardwired Model Humbling
- Ray McGuire accidentally hardwired a flawed financial model and was publicly called out by Joe Perella.
- He had to redo the model and felt deep embarrassment that shaped his attention to detail.
The Fake Rolex Lesson
- Ray McGuire wore a fake Rolex to impress and Joe Perella immediately saw through it in an elevator.
- He ditched the watch and learned you can't fake credibility with appearances.
Losing For Your Convictions
- Antonis Samaras launched Political Spring over a national conviction and accepted its electoral decline.
- He frames the loss as principled, saying losing for your convictions is tolerable and instructive.

