PayPal Mafia Alumnus Jack Selby: Wealth, Serendipity, and Secondary Success

TLDR: Jack Selby, the long-time managing director of Thiel Capital and member of the “PayPal mafia,” discussed venture investing, luck, and the changing aspirations of entrepreneurs during a private event. Selby emphasized the importance of grit and grandiosity in entrepreneurship and highlighted the role of luck in business success. He shared insights on the emergence of the next PayPal and the significance of the entrepreneur in investment decisions. Additionally, Selby discussed his relationship with Peter Thiel and the challenges of filmmaking. He expressed his willingness to be a “second banana” and the importance of being open to learning from smart people.