CEOInterviews.AI
Start App
Bill Gurley
General partner at Benchmark, Benchmark

Venture capital legend, Bill Gurley.

📅 Apr 27, 2026 Forbes 46 MIN 123 SEGMENTS · 20 SPEAKERS
Follow ⁠Forbes Under30⁠ (https://feeds.megaphone.fm/FSML6624324469) Recorded LIVE from the 2026 30 Under 30 Summit ...

Questions asked in this interview

12
  1. 0:02You're so far away. What's up, guys?
  2. 4:20Do you agree or disagree with that?
  3. 7:27How do we figure out what the signal is?
  4. 13:07What was the valuation when they were pitching you?
  5. 15:05What would your advice be for someone who's 29, kind of at the junction of going full in project management, full in as a realtor, not climbing the wrong ladder?
  6. 19:39What would your advice to them be on free or charge?
  7. 24:48You've already figured out how to hack it, right?
  8. 29:12They always have a note from you, right?
  9. 30:36And how do you avoid diluting yourself across too many things?
  10. 34:08... question is how do you think about allocating your time between the demands of active investing and the things that don't have an immediate ROI like mentoring founders, doing writing, speaking at events and how has that changed over time?
  11. 39:06And what makes you confident in that?
  12. 41:05What advice do you have for aspiring VCs like myself that are all looking to raise their second fund as to like what we should do and some of the things that we should avoid?
Randall 0:02 ↗
You're so far away. What's up, guys? All right, this is fun because this is the part of the summit where you guys are part. This is kind of like a town hall. So, start thinking about your questions. Not yet, but then we'll take your questions for Bill. But this is really fun because we got one of the world's great investors with us. You know, Zillow, Uber, Open Table, I mean, winner after winner after winner. But what's fun is that today instead of being one of the world's greatest investors, we have the world's tallest mentor. I was with Bill, we both gave TED talks last week. We were both in Vancouver. Shameless self-promotion. My TED talk was released yesterday. Okay. So, if you want to go to TED, I am at the top talking about philanthropy and billionaires. Check it out. Bill's talk, we're getting a preview because Bill's talk's not out yet, but I got to see Bill talk. This guy has a lot of wisdom for this crowd. And he's got a new book out called Running Down a Dream. And we got a bunch of dreamers here. So, with that, Bill, tell us real quick the thesis of your book because really it's a book for this audience.
Bill Gurley 1:19 ↗
Yeah, I've come to believe that there are too many people that are chasing a career that they were pushed towards, thought was the smartest thing to do, and it doesn't necessarily overlap with something they're fascinated with. And we could go into more detail, but the people that are in careers where they're fascinated are going to learn faster. They're going to do more. They're going to run more. They're going to get noticed. They're going to be wildly successful. And AI makes that even more true because the best that I've seen pick this stuff up and they run even faster. I mean, one negative might be you could see a further kind of separation, like inequality separation, but I do fear there are way too many young people that are grinding for the sake of grinding and achievement that aren't living the best life they possibly could be living. And I wanted to give more people more permission to do that thing.
Randall 2:22 ↗
What you say, fascinating, right? You're fascinated with. How does it, you know, we've all seen like follow your passion. That's the cliche. Follow your passion. You're using a different word. Is that the same?
Bill Gurley 2:36 ↗
No, I actually borrowed the word from Jerry Seinfeld, but he gave a Duke commencement speech. But I think fascination involves work in that when you're fascinated by something, you're endlessly curious about it and you just constantly want to study it and know more.
Randall 2:55 ↗
Like a puzzle.
Bill Gurley 2:56 ↗
Yeah. And so much of what separates an individual for success is understanding nuance. And innovation is really about understanding nuance because it's the edge of disruption in your field. And in order to get from the history to the bedrock to the nuance just requires tons of reps at this thing.
Randall 3:19 ↗
Yes.
Bill Gurley 3:20 ↗
And if you study something you don't like, you get tired. You're like, 'Oh, you have to take breaks.' Yeah. Everyone's done that in school. But when you're studying something you love, you just do it on your own. I think one great test is does it compete with social media or Netflix or something else that you'd be doing in your spare time, right? Are you more drawn to a breakthrough in your field almost as a piece of content?
Randall 3:32 ↗
Like accounting class for most of these people. So, right.
But then how do you nuance that versus the word passion? Because you know what's the difference between fascination and passion?
Bill Gurley 3:58 ↗
I think there's lots of people that could claim to be passionate about something just because they're kind of infatuated with the idea. But if it doesn't then lead to reps and work, then I think it's kind of short-lived or there's no motor that's going to accelerate you past everybody else.
Randall 4:20 ↗
Let me, you've probably seen, you know, Scott Galloway went viral, you know, with his career advice, which is like don't chase what you're interested in. Chase what you're good at. And you'll become passionate about what you're good at because you prove you're making money from it. Do you agree or disagree with that?
Bill Gurley 4:37 ↗
I don't buy into it really. And I was actually on his podcast and we talked about it a little bit, but I don't think there's any spirit to that. Like there's no, I think when you talk to somebody who's fascinated with something, you can sense it, you can see it, you can feel this kind of, they idolize the idea of being good in that field and I just don't think you get that with just 'Oh, I'm good at this thing.'
Randall 5:10 ↗
Right. When you make investments, I mean you have hundreds of founders coming in front of you every year. Are you looking for that?
Bill Gurley 5:20 ↗
You know, I had a chance to interview Bezos once and was asking him how he did so many great angel investments and he said because he's busy with that day job, right? He said he just really looks for this kind of unbridled determinism that you can't stop. And I think there's an element of that and what I'm talking about, like you sense this person is going to be so deep in what they're doing and understand every little bit of it that you have high confidence they're going to be successful. You're often betting on people that are riding new technology waves. And I think for the most part tech founders are always, their fascination is the edge of what the technology can accomplish. And you see people repot themselves. I like to point out Brett Taylor who we've backed three different times. You know, he was doing maps at Google and then he worked on social media and now he's running Sierra, which is an AI customer service play. He's just always right there as the thing changes and on top of the next thing.
Randall 6:28 ↗
How is this, you know, you've had a couple different careers within your career. How is this mindset, you know, how did you apply it to yourself?
Bill Gurley 6:37 ↗
Well, I did. So, and this, I think, is a really important message for young people. I had a three-year career as a computer engineer. Decided that wasn't my dream job. Partially by asking myself, do I see myself doing this 30 years from now? I went to MBA school. I went to Wall Street. Worked there for three years, had the same discussion with myself which got me looking in a different direction, went to Silicon Valley and then I was a venture capitalist for 25 years. So the first two things didn't take me to that place. They were stepping stones. They weren't a waste of time. But it's okay to change if you're not there. And the journey to find it can be multi-step.
Randall 7:27 ↗
Your investing career. You've, you know, again, you're one of the very first investors in Uber, you know, just again dozens of winners. You're very good at pattern recognition. How does that apply to kind of this philosophy in terms of when people are trying to figure out what's my thing? Especially right now with what is happening with AI, there's all these notes out there, you know, we got a lot of noise out there. How do we figure out what the signal is?
Bill Gurley 8:01 ↗
I mean, I really think it comes down to understanding whether this thing you're tilting at is something that you feel so strongly about that if you, I mean, one thing I find founders sometimes don't recognize and it's gotten worse in the past two or three years. You might be doing this 15 years from now, right? Because a lot of founders have, like me, have ADHD and like bouncing all over.
Randall 8:28 ↗
We got a lot of ADHD in the audience. Let's hear it for ADHD.
Bill Gurley 8:34 ↗
But you could, you know, and you start hiring people and you do one round and you do another round. You're kind of pot committed at that point.
Randall 8:43 ↗
That's right.
Bill Gurley 8:44 ↗
So I'd really make sure you know and ask yourself the question if I'm still working on this 15 years from now will I be happy or not?
Randall 8:52 ↗
Yes. It's important. Yes. All right. So, I'm giving everyone a five-minute warning. We got a microphone up there. Don't have to line up yet because I, but think of your questions for Bill. At what point, Bill, does your fascination become stubbornness? Because there is the other thing is all right, I can't see myself doing this 15 years on, switch. But on the flip side, maybe I'm fascinated by it, but you can be fascinated and push, but it ain't going to go anywhere. It's just not meant to be. Either you're not good at it or it's not a good idea.
Bill Gurley 9:24 ↗
I mean, I'm probably wildly optimistic that if you're really fascinated and you learn it all that you can make a mark in almost any field. There are obvious categories where talent matters like pro tennis or downhill skiing and in those cases it's kind of, we saw Michael Phelps was here yesterday and he's like I worked harder and there was no doubt I was going to be the best in the world. I can work as hard as I want. I was never going to even be within a minute of him. But I've seen him talk and that work ethic that he had was only possible because he cared enough to go do it. But in any case, the one thing I would say about those jobs though, whether it be Olympic sports or Hollywood, there are so many support jobs around that individual job. And many of the profiles in my book are those types. There was a woman that all she could think about was movies and she didn't see herself as an actress. So, she went and got a normal degree and didn't ever consider it. Later, she found out, oh, there's hundreds of people that surround this individual talent role. And she started as an assistant at an agency and then ended up becoming one of the biggest agents of all time. So there are areas around these talent jobs where there's tons of other jobs. Sports analytics is another one that's a growing field.
Randall 11:04 ↗
That area. Who is the person in your book you think is most relevant to the 30 under 30 community in terms of a story that they can relate to.
Bill Gurley 11:14 ↗
I think I can get that. So, I have a chapter in the book titled Embrace Your Peers, where I encourage people to create peer circles as they're rising up. People that are on the same rung of the ladder as you. And there's a great story. This guy Jimmy Donaldson, 17, loves YouTube, trying to figure it out. There aren't that many people that had figured it out. He creates a group of three other like-minded people. Claims they were on Skype 16 hours a day for four years and they all became millionaires. Jimmy's Mr. Beast.
Randall 11:50 ↗
Okay, that's good. That'll work.
Bill Gurley 11:53 ↗
And so, yeah, I think, yeah, co-learn. And then he would go on to say that he used Malcolm Gladwell's 10,000 hours thing and said this isn't precise math, but he said we got 40,000 hours because we're all learning independently, sharing, and the hive mind version of the Gladwell, you know.
Randall 12:15 ↗
Yeah. And people get overly worried that they have some kind of proprietary knowledge or that sharing is not in their best interest. And I'm completely on the other side. I think you're full open kimono.
Bill Gurley 12:27 ↗
Yes. Yeah. Ideas are a dime a dozen. The more you share, the more will come back to you.
Randall 12:32 ↗
All right. That's a great point of view for this group. What's the biggest mistake either you've made in your career or somebody in your book that you think was the most instructive?
Bill Gurley 12:45 ↗
Well, the biggest mistake I made in my career is when I was three years into the venture capital business, I met Larry and Sergey at their office with 25 employees. They pitched Benchmark and we failed to invest in Google. That name, you know. So, that's about as big a mistake you can make. I'd like to think it kept me motivated for the next 22 years.
Randall 13:07 ↗
What was the valuation when they were pitching you?
Bill Gurley 13:12 ↗
They ended up doing the deal at 80 pre with Kleiner.
Randall 13:14 ↗
80 million. 80 million pre and now what's the mark?
Bill Gurley 13:18 ↗
Yeah, three trillion. Yeah. So, huge mistake.
Randall 13:25 ↗
What's your favorite investment ever?
Bill Gurley 13:28 ↗
The one that had kind of the most intellectual appeal was probably Open Table because we invested when there were three restaurants on the network and had a theory that a network effect could take place where it could tip towards winner take most. And I remember being on vacation in Bali and going in a restaurant and seeing the unit there. And you know, 20,000 restaurants later and just the fact that the idea played out in the way that we had anticipated, very satisfying.
Randall 14:03 ↗
Powerful. Very satisfying. How much, if folks want to ask questions while you start lining up, in terms of how much have you invested over your career? I mean it's a lot of checks. So how much have you put to work?
Bill Gurley 14:19 ↗
Oh, I've never tried to add that up actually. And to be fair, my firm focused almost entirely on first money in early stage. So, relative to the other venture capital firms, we've always deployed much less money. We've never, less money and higher leverage.
Randall 14:38 ↗
Well, there's, you got a long line, Bill. Look at that. We got 10 people already. So, all right. Here's the deal, guys. No pitching, you know. Yes. You know, people go crazy to get audience with this guy. So, no pitching, just asking and go identify yourself, but quick. Don't need the whole who you are, what you do in 10 seconds, and then the question.
Jana Crum 15:05 ↗
Hi, Bill. I'm Jana Crum, a dual career real estate agent here in Phoenix, pro project manager and also a realtor. I've heard a lot of people talk about what you're talking about. Don't end up climbing the wrong ladder. What would your advice be for someone who's 29, kind of at the junction of going full in project management, full in as a realtor, not climbing the wrong ladder?
Bill Gurley 15:29 ↗
Yeah. Well, I wrote a book about it so you could make sure you get a copy. I'd really, Angela Duckworth has this phrase. She says move towards warmth and nutrients. Like I would really ask yourself which of these things pulls at you the most? Like which one are you really most curious about? And one thing you could do in any of these situations is just role plays. So spend a week telling yourself it's definitely going to be this one thing and study that week, take notes that week and then the next week tell yourself as a game, I'm only going to do this and then do that and then after two weeks I think you'll probably have a good point.
Randall 16:17 ↗
That's an A/B test.
Bill Gurley 16:18 ↗
Yes. Yeah. Your own A/B test.
Randall 16:20 ↗
Thank you.
Pra 16:25 ↗
Hi Bill, my name is Pra. I'm building an AI drug discovery startup using an NVIDIA award-winning AI model and mini brains called organoids to accelerate drug discovery for Parkinson's, Alzheimer's, and other brain diseases. And I just wanted to ask you because I'm obsessed on LinkedIn and looking at venture capitalists' outlook on this industry and a lot of them seem to agree that using technology for health is the next trillion dollar industry and it's the next boom and do you agree with this thesis and how do you think this plays out over the next couple decades?
Randall 17:04 ↗
That was only slightly selling himself.
Bill Gurley 17:07 ↗
But one, I do agree to a caveat. I've not been a healthcare investor, and there are plenty that are, so I'm not the perfect person to ask that question, but in the past five days, I'm sure you read the pancreatic cancer stuff that came out like this and at TED, this was talked about, the woman from the Arc Institute was there. So, I think the world is your oyster. Everyone agrees. I don't think there are any skeptics. It's a good time to be young and entrepreneurial. So, good on you. Good luck.
Randall 17:42 ↗
Great. Great category. Next up.
Steve 17:45 ↗
Hey, Bill. I'm Steve. I'm a partner at Antifund, also a venture capitalist. We're investors in AI, consumer, and hardware. Question for you. It seems like you've made a lot of investments in the consumer tech space. Zillow, Next Door, Uber, Stitch Fix. Very curious what are some interesting consumer demographic trends that you are observing and noticing that is maybe coming with AI?
Bill Gurley 18:17 ↗
Demographic with AI, that's combining a lot of different things. There are a number of people that are trying to use AI to make the decision on behalf of the individual. Part of what happened with the internet is we categorized everything you could possibly buy and now you have the paradox of choice and all this stuff. So, how do you, and people are, I mean we're doing this at Zillow. People are doing it in the travel space. People are trying to figure out how you could custom package things for people. I think the unfortunate reality is there is a bit of an inequality thing happening. And so the other thing you see is people target the high end of the market more because there's more disposable income. By the way, real quick on the health care thing, especially because you mentioned Parkinson's, one sad reality is pre-AI, a lot of drug companies end up focusing on symptom support rather than solving it because there's more money in that. And unfortunately, that's less, you know, it'd be much better if we cured the disease. Yeah. I don't know why I thought of that. Good luck with your portfolio.
Randall 19:37 ↗
Next up.
Maline Hillyard 19:39 ↗
Hi, Bill. Nice to meet you. Appreciate you, Bill, being here. Maline Hillyard. I'm the founder and CEO of Dopa G. We do overdose prevention and substance misuse training video games and other products around this. I'm curious, you know, kind of the older wisdom is if you have a product that's valuable, don't give it away for free. But now with AI that we can be creating and releasing new products so quickly, is there, and a lot of creators online are giving away education or other products for free as kind of top of the funnel. Are you seeing this with your portfolio companies? What would your advice to them be on free or charge?
Bill Gurley 20:21 ↗
We've done it all. I mean a big part of why my firm backs so many open source companies because the product got out there and became a top of funnel way to get users in. I think you have to, I had a conversation with the guy running the New York Times once and he was thinking this way and I think in their case it was flawed because the people that love the New York Times, it's almost like a wall there. They'll pay this much and you could lower the price and it doesn't really increase their distribution. So you have to understand the target market and the end market and by the way if you're going to do the premium thing it's got to be really big right because otherwise you're going to have a hard time funneling it down. So I don't know enough about that particular category. The other trend you might be interested in is a number of companies have been able to get consumer apps available for reimbursement on insurance claims and that's obviously very good if you can make that happen with a product like that.
Randall 21:27 ↗
I see a lot of nods. Done.
Jay Ives 21:31 ↗
Hey Bill, how's it going? My name is Jay Ives. I am a CEO and founder of a growth marketing agency in New York, Jives Media, and we're also currently working on AI as CRM, which I'm pretty stoked about. I know that you've made a few sound investments over the years. And my question is, what are two or three things that you really look for when investing in a founder? Not just a company, but a founder.
Bill Gurley 21:58 ↗
Yeah. So, I think that determinism Bezos talked about, sales ability. You're selling so often. You're trying to close people, close investments, close deals, close customers. Like you're just, whoever the founder is represents the company. And I've seen people that have 10x sales ability relative to someone else and it really matters. And then lastly, and this kind of relates to the founder, but more the company and relates to the question just before you, many of the best outcomes we've had, the company has some unfair go-to market advantage they've come up with. So, some way of getting customers that's not rote advertising or rote salespeople. And because if you can figure, you know, there's this whole product-led growth, you know, meme, like that stuff really matters.
Jay Ives 22:56 ↗
Cool. I really appreciate you.
Bill Gurley 22:58 ↗
Yeah. Good luck.
Thor Weber 23:01 ↗
Hi Bill. Thanks for being here. My name is Thor Weber. I'm the founder of Skill Dome. We do AI tutors. My question to you is around defensibility and specifically the question is is there any defensibility left in software?

61 more exchanges in this transcript

Sign in free to read the rest of this interview. No card required.

Sign in to read the full transcript

Cite this transcript

APA, MLA, BibTeX
APA

Gurley, B. (2026, April 27). Venture capital legend, Bill Gurley. [Interview transcript]. Forbes. CEOInterviews.AI. https://ceointerviews.ai/interview/869905/

MLA

Bill Gurley. "Venture capital legend, Bill Gurley.." Forbes, 27 Apr. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/869905/.

BibTeX
@misc{gurley2026_869905,
  author       = {Bill Gurley},
  title        = {Venture capital legend, Bill Gurley.},
  howpublished = {Interview transcript, Forbes. CEOInterviews.AI},
  year         = {2026},
  month        = {apr},
  url          = {https://ceointerviews.ai/interview/869905/},
  note         = {Speaker-attributed transcript with timestamps}
}