Gurley advises seeking mentors two steps above you rather than shooting too high like CEOs.
“the person that's two steps above you on the ladder has never been asked to be a mentor, and that's probably your best place to start, and they'll be flattered that you ask.”
Gurley observes Silicon Valley has unusually high willingness to give advice to strangers, similar to Nashville songwriters.
“In Silicon Valley, if you walk up to somebody that you don't know and ask them for advice, the probability that they say yes and spend time is higher than you would ever expect.”
Gurley says Seinfeld initially didn't know stand up comedy could be a real professional career.
“Jerry Seinfeld was was wandering around New York thinking about what his career would be, and he had an inkling that he wanted to be a stand up comedian, but he didn't know that it was a real thing. He didn't know that you could actually go be successful and have a career.”
Gurley says Silicon Valley's willingness to grant fifteen-minute meetings is shockingly higher than Wall Street.
“In Silicon Valley, the frequency with which you can ask someone for fifteen minutes of their time and get a yes is shockingly high.”