Bill Gurley says that right now, the worst thing you can do for your career is play it safe

"The number one thing is to get out of your head this ideal that gets passed around in the self-help world: 'go get a mentor,' and everyone runs out and cold calls someone that's ridiculously too high and unachievable, and it doesn't work."

source https://techcrunch.com/2026/02/22/bill-gurley-says-that-right-now-the-worst-thing-you-can-do-for-your-career-is-play-it-safe/