Contrarian Timing: IPO When Nobody Will

"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.”"

"“[ The underwriters] were like, ‘You guys have to have more seasoned execs on here. We can’t take this to our clients,’ ” Woolway remembered. “And we said, ‘Nope. This is the team we have.’ ” Woolway understood the bankers’ plight, though. “The underwriters’ job is to push back on all that stuff,” he said. “Their job is to sell the stock, so they’re doing what they need to do to make it easier to sell the stock.”"