Years later while working at AOL, Palihapitiya did a deal to integrate Instant Messenger with a fledgling product called Facebook (He had wanted AOL to try to buy Facebook, but the company was too tangled up in legal drama).
Eventually the partnership unraveled, and Facebook’s founder (a then-teenage Mark Zuckerberg) asked Palihapitiya if he would leave the venture firm where he had taken a job, and join the startup instead.
“I said, ‘What is the distribution of outcomes at Facebook?’ he asked himself at the time.
“Most of the scenarios were less than [I would make at the venture firm], but there were a few scenarios where I could make a case that it could be equivalent to what I would make at Mayfield over a four-year period, and in a very small number of cases it would be in excess,” Palihapitiya said. Even if it doesn’t work out, he thought, “I will have met some of the smartest people in the world, and I’ll be in the game. And I will have learned something about myself, whether I can do something at a really early-stage scale.”
As it turned out, of course, Facebook was a pretty good bet for him.