Snack: Bill Gurley
How Success Happens
September 27, 2026
Bill Gurley doesn’t just invest in unicorns—he helps create them. In this clip, legendary Silicon Valley VC Bill Gurley shares candid advice with college students on how to think about careers, risk, and opportunity long before you launch your own startup.
Speakers Bill Gurley
SPEAKER_1 (0:00)
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upwork.com. You know, another thing that you write about in the book, I know, is, and this ties into learning is mentorship. How do you make those connections?
Bill Gurley (2:47)
First of all, I try and divide it into two places, because I think immediately people think they want their mentor to be Warren Buffett. And like, that's not realistic. And so what I suggest is that they have a group of what I call aspirational mentors, and then more realistic, pragmatic mentors. So the aspirational ones, make a list of the people who really stand out in the field you want to attack and study them and learn from them. You know, it's interesting, like going way, way back, you might have needed to meet someone for them to mentor you today in this day and age with YouTube videos and podcasts. Like a lot of these people are out talking about what they do and you can go like consume all that. And then for identifying mentors, you're actually going to meet with, just be more pragmatic. There are people two tiers down from the greats that no one ever calls, right? Find out who they are. They'll be flattered if you're studying them. And, you know, they may not all respond, but you might be surprised, like 40% of them might say, okay.
And then the last thing I would just say, different mentors can bring you different things. So you might use one mentor to know about one topic and a different one for another leadership or some particular skill. And so you don't have to, you don't have to have this, this, you know, Yoda type person who's all knowing.
SPEAKER_1 (4:13)
I spoke with Damon John a while back, and he talked about this a little bit and said, you know, being a mentor, like I'd love to give you advice, but don't come to me and say, I've got this problem, give me money to fix it. That's not what mentorship is.
Bill Gurley (4:29)
Yeah, I think, I think, you know, I mentioned in the book, you need to be nuanced about how you approach mentors and the types of things you ask for. I think you can't waste a ton of their time. I think you can't pretend they want to spend three hours at a dinner with you. But if you can be efficient with their time, if you can know what they know that you don't, and if you can be very specific about what you want. Like, I think it is okay to say, I've got this tactical problem. Here are three ideas I have. What's your feedback? By the way, many of the people in the book that we profile did this thing where they identified the greats and kind of studied them.
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