Contrarian Timing on Economic Cycles

“Thiel’s interest in Girard often led him to zig where others zagged—an instinct that informed the IPO filing. “If you’re in a world where no one goes public,” Thiel explained, “maybe paradoxically, that is the time to go public. Because, you know, it’s a positive counterpoint to the chaos or something.””

“the timing of PayPal’s IPO wasn’t solely a triumph of Girardian logic. Thiel admitted that rivalry, conflict, and emotion also played a powerful role. “The competitive thing in me was just, you know, if the bankers thought we weren’t ready, then it was more important than ever. It was sort of like a Wall Street versus Silicon Valley thing,” he said of his will to prevail, “and there was a part of my thinking where, emotionally, I felt like the Wall Street banks were especially negative because we were encroaching on their turf.””