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Bill Gurley
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Ann Barry
for Friday, February 27th it's Brew Markets Daily and I'm Ann Barry. Anxiety around AI is on the rise, or actually it's just risen among software investors watching sector stocks sell off among white collar employees wondering if they will be displaced among young people who've not yet entered the workforce but are asking fearfully which options will be there when they do well. For a positive outlook on building careers today, almost an antidote to these fears, renowned venture capitalist Bill Gurley wrote his new book Running Down a Dream. And we welcome Bill to the show to break down how the pillars that he advocates for passion, curiosity, lifelong learning, peer and mentor networking, going to where the action is and to talk about how these have manifested in public company leaders. We discuss founder CEOs and their company stock price performances, how Sachin Adela reframed the value of learning to turn Microsoft around, why Elon Musk's range across multiple industries defies leadership norms but indicates one replicable secret to long term success how the best CEOs don't delegate curiosity about industry and competitor changes and why the likes of the PayPal and Amazon mafias, groups of peer alums, have gone on to do extraordinary things. And we go beyond the book that builds insights into the market today. A general partner at Benchmark, a leading Silicon Valley venture capital firm, Bill has invested in and served on the boards of such companies as Nextdoor, OpenTable and Uber. And today he still serves on the board of Stitch, Fix, Ticker, SFIX and Zillow, the NASDAQ listed real estate innovator for more than two decades. He's written about technology on his popular blog above the Crowd and on his social media accounts. So we sit down in studio. Bill was in from Austin, Texas, and we talk about the industrialization of venture capital, why fewer big tech winners are going public, and how IPOs need to change to work for retail investors. That conversation in just a moment, but first a word from our sponsor, Charles Schwab Trading at Schwab is powered by Ameritrade. Unlocking the power of thinkorswim. The award winning trading platforms loaded with features that let you dive deeper into the market. You can visualize your trades in a new light on thinkorswim desktop with robust charting and analysis tools all while you
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Ann Barry
Learn more@schwab.com trading and now my conversation with Bill Gurley. Bill Gurley, thank you for joining. Looking very smart and suited up. Fresh off the set at CNBC this morning.
Bill Gurley
Yeah, I told my wife I don't normally wear suits but I'm going to today.
Ann Barry
Well, here it is. So we've got it in the brewmarket studio. Well, you've got this fantastic new book out which I absolutely devoured over the weekend. It's called Running Down a Dream. A reference I think to Tom Petty. There's a shru in the studio. Maybe so, maybe no. And it's all about finding one's passion and trying to build a career that is founded in passion and most importantly, curiosity, which is a big learning I took from your book. Talk to us about that curiosity and how it feels long term commitment to it, to a path.
Bill Gurley
Well, I think in order to really differentiate yourself in a field, you need to be a lifelong learner and you have to keep wanting to learn. I think a lot of these kids have so much pressure on them when they get all the way through college and they're grinding so hard, they're like, whoo, I don't have to learn anymore. And they go off into the workplace. But it's the wrong attitude, the best. And we have profiles, deep dives on nine different careers where people started at the bottom. They all are constant, continuous learners. The reason this matters to what you just asked is in order to be able to do that without it feeling like a grind, like being in that flow state that you read about, you have to really be curious about it. You have to care about it. Like if there's something new that pops up in your field, you just consume it naturally without even thinking. And all the best that really love what they do have that skill set and it's hard.
Ann Barry
It's hard. And you call it a skill set which is sort of interesting as opposed to the sort of natural thing that courses through people's veins. Do you, do you think that learning to love, learning is something that can be taught or do you think it's innate? Where do you think it comes from?
Bill Gurley
It could possibly be taught. And so many of the greats, you know, whether Buffett to. I just saw a long podcast with Toby from Shopify. If you give one piece of advice, what would it be? And they all say read, read, read, read. And I do fear that in this short attention span world we're in that the children read fewer books. They do get more information from podcasts and those kind of things. So learning doesn't have to be, you know, one dimensional as in a book. But you know, I read almost none until I got to graduate school and then a bit flip for me. So I would like to think that that could be true of anyone. Like the. And I, once I started consuming books, it, it became addictive and I, you know, I'm still a vast reader today. At the back of my book is a, I think 35 books that I recommend to other people. So I think, I hope, I'd like to hope you could learn to learn. But the learning I'm talking about, like if you've identified your, your real obsession, it doesn't even feel like learning. Like it's not something they'd have to teach you to do because it would just come naturally. If you watch these interviews with Magnus Carlson, he says, you know, he says I, I hate grinding through exercises, but I love learning about my craft. And he's read all these history books on chess. Like there's he, he devours the information but on his own terms.
Ann Barry
You know, that idea that someone has that hunger for learning and perfecting their craft over time. When we think about that transferability from a markets perspective, Bill I really thought about public company CEOs just sort of bring it to that space for a bit. Those who have found a run and those that are not. And there was some interesting data on this. There are some papers out there that suggest that founder led companies have outperformed the S&P 500 significantly in recent years. A lot of that being tech, which of course is the field that you're a leader in. You know, Amazon, Tesla, Nvidia, Meta, Shopify, app, Lovin. Do you have a perspective on that?
Bill Gurley
I think founders are unbelievably determined about what they're doing. In fact, one time I asked Bezos how he was such a good angel investor when he's obviously busy doing, running one of the largest companies in the world. And he said, I only look for one thing. I want to know that this person's going to go do this thing come hell or high water, whether I invest or not. And so you have this determinism. But I think that determinism also drives learning and, and curiosity about what they're doing. So any. You know, I was just listening to Brett Taylor talk about Sierra, this new AI company that he's running. And he obviously has spent the past three years repotting himself as an AI executive. Like he's, he's, he's out there every day testing what's possible, studying what's possible. And all the great founders do that. You know, the, there's a great book, the Innovator's Dilemma, that explains how founders disrupt other industries. And the key thing that enables that is when new wave comes along, they are on the front of understanding it and what's possible and how to use it then. And that's the skill set that allows them to be successful.
Ann Barry
Do you think that skill set is going to be table stakes in a world in which AI is causing so much anxiety about how to get a career and keep one?
Bill Gurley
I do. And I would offer you the, the what to me is a stark contrast and, and almost this ironic reality where if you don't really love your job and you just kind of dial it in every day and, and I think, I fear there's a lot of people in that situation.
Ann Barry
Most people, yeah.
Bill Gurley
We found this Gallup poll from 2023 that said it was over 50% of people who aren't engaged at work. That's where the term quiet quitting came from. Then I think you're really at risk because you're not, you're not pushing to understand what it's going to mean to be in your role in the future, 10 years from now. This AI is a new technology, no different than really than a computer or other technologies that have come along and you need to be proficient in it no matter what role you're in. And the people that are hyper curious, I think, are already figuring that out. Like the minute it popped up, they were playing around with it. And they are the ones who know in each and every industry, we, what it's capable of because they're out there testing it every day. And so I think if you're able to put yourself on a custom career path where you're really chasing your craft almost the way an artisan would, then I think AI is a superpower. Like, it's the flip of that person who may be dialing it in and not trying, because all of a sudden I can go accomplish more than I ever could have before. I can learn faster. Like, there's one just truism today, you can learn faster about anything than at any point in history before us. And, you know, the Internet brought us Wikipedia. But AI is just completely different. And we, of course, we have podcasts and YouTube interviews, like, you can, you can study now any topic faster. Like, way faster than you ever could in the past. And that should be, like, super interesting to someone who wants to get ahead. But you have to have this proactive mindset that I'm trying to win.
Ann Barry
You know, you have a very positive outlook on it. Right. And there are other voices out there, Bill, who've said something similar, not quite as articulately perhaps, which is use this as a tool and you can turbocharge ahead. But if you take a look at the employment figures, folks coming out of school right now or earlier in their careers are seeing particularly high levels of unemployment. And because employers are saying everything that you've just described, hey, guess what? Current employees go do that. But it means that there are going to be fewer jobs and openings available for the next generation coming up.
Bill Gurley
Yeah, my book wasn't written as an anecdote to AI unemployment writ large, but I would say that. Well, I want to back up real quick. I do fear that the. The evolution of the college career. Matriculation has gotten really, really grindy. And we start worrying about kids getting into college in, like, the sixth grade. Jonathan Haidt calls it the resume arms race.
Ann Barry
Yeah.
Bill Gurley
And we start packing their day and their schedule with chess lessons and cello lessons and lacrosse lessons and volunteering at the spca. And because we're all worried about them getting into school, it's all well intended, but it becomes very grindy, and there's not a lot of time for play or, or creative, you know, and are really trying to identify the thing that you're passionate about. And others have talked about this. Rick Rubin's talked about it. Heit has talked about it. And I fear that the kids are taught to grind. And they. And they. And also, you know, years ago, they wouldn't let you declare a major until the end of your sophomore year. Now you have to apply to a major at many schools like England.
Ann Barry
That was what I grew up with.
Bill Gurley
Yeah. So you're moving from, you know, making that decision when you're 20 to when you're 17. And a lot of these kids have no idea what it is that they really want to go do, and they need time to explore and learn. So anyway, I worry that's part of the problem because you get out and you're exhausted and you're not thinking about this as something that could be fun. You're thinking about this as a drudgery. And so anyway, I think that's also part of the problem. So I would just say if you're looking for I'm not going to say this book will solve all unemployment problems. It's not why I wrote it. But if you're looking for an alternate path to that grind and something that might give you a little inspiration and motivation and the methodology, by the way, to make it work, I would give this a shot like this is a good alternative to the traditional path.
Ann Barry
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Ann Barry
And now back to my conversation with Running Down a Dream author Bill Gurley. You know there was something you said in there, Bill, just now and also in your book, which is about AI's ability to accelerate learning. And you talk about how people who are very successful, even while they're senior and successful, keep on digging actually into details. Now, there's one piece I want to read from your book you wrote. Long after he was already successful, J.D. rockefeller continued studying every element of the oil business, from the roughnecks pumping it to the pipelines and train systems carrying it, including tedious examinations of his competitors, businesses. I hear your Texas draw, by the way. And I read that quote and it also came together for me. But I think, you know, look, I remember, I'm just going to, I went to get my mba, right? That's why I came here to go to grad school. And there was this kind of philosophy that you grind away to your point and then you reach a certain level of seniority. CEO, and then you sort of become strategic.
Bill Gurley
Yes, right.
Ann Barry
You sort of become hands off and big picture and high level and strategic. And you've just described someone who probably was, but was informed by attention to detail and the learning that that took. Just talk about what you see in terms of the kinds of leaders, particularly public companies.
Bill Gurley
Yeah, yeah. So, you know, I was on a podcast, we were interviewing Satya Nadella at Microsoft, and I would, I think it's hard to put what Satya has accomplished in context because it's such an outlier to, to go. Most companies, once they get big and have had an extended period of, of degrowth, like where they really slow down, they never come back, like they never, they never get back to glory. And I think that's been, I think that's just considered a truism. And here he comes along and takes over a company that's 40 years old and is able to get it going again in a vibrant way. And it's, it's truly remarkable. It's probably the best turnaround story, you know, other than maybe Jobs going to Apple, those two. But, but to be at that level. And so you ask, how does it work? How did he do it? And what he says is that he believed the company had become a know it all culture where every single person felt like they were an expert and no one had the humility to ask, you know, what might I not know? And he, he said he, he told everyone, we're going to change it from a know it all culture to a learn it all culture. And a big part of my thesis in this book is you have to be obsessed with continuous learning to stand atop your field. And it's amazing that he could transition a culture in that way so, so quickly, you know, and it's super impressive.
Ann Barry
You also talk in your book, Bill, about how learning shouldn't just be limited to one's own field. You say perfect your craft, but also be a citizen of the world. Be out there and learn from other places. Talk about that.
Bill Gurley
Yeah. So the person that probably, I think developed that theory the best is David Epstein with his book Range. But it turns out that a lot of the most interesting innovations come from people who weren't in that field forever. It's people that transitioned into that field from other places and brought mental models that were different because there's groupthink that get stuck in one place. I think it's a bit of an elevated assignment just for your listeners. It's. It's harder to go listen to a talk about something that's in a field different than yours and pull out the nuggets because you have to sift through the noise a little bit. But if you find them, I think there's quite a bit of history. And David went through so many examples where it could be a really big unlock and a differentiator. Right. Because other people aren't doing that. So I found that to be remarkably rewarding myself. It's one of the reasons I'm involved with the Santa Fe Institute. It's very committed to interdisciplinary work. A lot of the colleges, by the way, and universities are creating more kind of cross discipline institutes for this reason.
Ann Barry
It's interesting because listening to that description, I couldn't help but think of Elon Musk. And I read Walter Isaacson's biography of him. Right. And there's this one part that really struck me where he sort of pulls SWAT teams out from SpaceX to go solve something at Tesla, or from Tesla to go solve something at X when he first took over Twitter. What's your perspective on that? Because lots of CEOs are actually not given permission to spend their time in a multidisciplinary way like that. He's maybe an extreme example.
Bill Gurley
Yeah, well, I mean, in his, in his famous Stanford graduation speech, Steve Jobs makes this argument like, it's almost hard to believe that a calligraphy course in college that he took had a massive impact on the first version of the Mac. So that's a like, that's a very extreme example of the same thing. Yeah, I read that Isaacson book. You know, he's talking, and he's talked since then in several podcasts about this decision to use stainless steel at SpaceX. And you know, his podcasters interview him. How'd you know how to do that? And he said, well, you know, I had a little experience with stainless steel over at Tesla. So, yeah, he has frequently talked about borrowing from one and taking it to another. I'm not sure that most CEOs have either the mental capacity or the energy to do multiple companies simultaneously. So I don't know if we can go recommend it for everybody.
Ann Barry
Well, but you've been in the position of hiring CEOs or leads, you know, senior leaders in companies private or in preparation for their own IPOs. Board members. Do you practice what you preach or what you've been inspired?
Bill Gurley
I think it's certainly a really great idea from a board perspective to put people that have different expertise and disciplines on the board so that they can have this type of effect on. On helping to lead the company. And that is a common practice.
Ann Barry
I want to talk a bit more about one other suggestion or principle in the book, which is to go where the action is.
Bill Gurley
Yes.
Ann Barry
Right. And that resonated with me because I was in London, I knew I wanted a career in finance, and I was like, I've got to go to New York. Absolutely center of the globe. And I.
Bill Gurley
Exact same thing in 1993.
Ann Barry
Yeah, that was it. Go where it's happening.
Bill Gurley
Yes.
Ann Barry
In the digital world, there has been a lot of talk about democratization of access.
Bill Gurley
Yes.
Ann Barry
And I, frankly, would be the next incarnation of it. Right. Do you still have the perspective that going geographically where the.
Bill Gurley
Yeah, and I'll tell you why. But you just said something that I want to double click on. You know, you talked about, like, your ability to have access is easier than ever before. So identifying both peers and mentors and people that you could learn from and even the ability to connect to them either through something like X's DM feature or in a Reddit subgroup or whatever. Like, that's never been easier either. So two of my core principles are learning as much as you can and connecting with peers and mentors. Both of those are easier than they've ever been. And this is where I'm trying to paint some optimism onto where this stuff's taking us. But, no, I fundamentally believe that if you. You are certain what you want to do, if that industry has an epicenter, then. And you have the wherewithal to get there, which is not. Some people obviously have commitments that don't allow that you should absolutely go to the epicenter. I think most humans have this innate fear. They make two things that I think are wrong. They have an innate fear that it'll be overly competitive, so they won't be able to stand out. And then they also have this. They talk themselves into this idea that it would be okay to be a big fish in a small pond. And I disagree with both of them.
Ann Barry
You do okay.
Bill Gurley
And here's the thing. In order to be successful, I argue in the book, you need to learn as much as possible, find as many peers as possible, and especially peers that would like to co evolve with you and then three to find mentors. All of those things are accelerated massively in the epicenter because your opportunity to do any of those things, if you go to Silicon Valley every single night, there is a networking event you could go to or a talk or some place where you might learn something new or meet someone new. It's unbelievable how many of those things that are out there. And on top of all that, what I just said, a lot of people talk about luck in their career path. If you interview people, they say, oh, this fortunate thing happened. Oh, you wouldn't believe it. I met this person, they introduced me to. So and so in the epicenter, your probability of lucky events goes way up, way up. And so yeah, if you can do it, do it. There's this belief we all have that competition makes it too hard. And in many industry, you know, in downhill ski racing, maybe there's only one winner of the gold medal, but in most industries, lots of people win. And if you can get out of this kind of competitive mindset and get into this, like I want to be in the system and learn and co evolve with these other people, you'll do way better. And it. And so anyway, yes, Go, go, go. I'm glad you went. I did the same thing that particular chapter. This, this book started as a presentation I gave at a university and that tenet wasn't in there. We added it and I'd say it's the one of the people that read the book that gets the most attention.
Ann Barry
It's. I thought actually as I was reading this that exactly this chapter, Bill, I couldn't help but think of certain companies that have become known for quote, mafias that have come out of them. Right? Yeah, PayPal, that's what the PayPal mafia. Peter Thiel, Elon Musk, Max Levchin, Reid Hoffman, David Stack, Steve Chen, Chad Hurley. I mean, and then there's an Amazon mafia too, actually. Now if you take a look at Mark Laurie, you take a look at Eric Ferguson.
Bill Gurley
Yeah, and those peer groups, once you get in them. And by the way, I'll give you another example that I just love is the general magic situation, because that was a failure. But there's a movie you can Go watch. It's free on the Internet. A documentary of general magic. So the company didn't work, but all the people that were in there went on to do these amazing things.
Ann Barry
What did they go do?
Bill Gurley
Well, Tony Fadell's one of them, profiled in the book. But, but anyway, go watch it. Like, I, I don't even want to steal it. It's such a good piece of content. But to your point, you know, you get into these peer networks and not only do you learn faster, but there's a, there's a bit of. I think it's like a positive. I don't think of it as competition, but when you see other people doing certain things. Yeah, it raises the bar for you.
Ann Barry
It raises your game.
Bill Gurley
Right. No doubt. And so when those people leave there and they all, you know, leave PayPal and they all start doing their own thing, you know, they're still in contact, they're supporting one another, but they also see them doing that, I'm going to do it too. You start to believe like in what's possible. So, yeah, I think those are, those happen all the time, by the way. And if that's, that's just another reason to get out there and get in the epicenter.
Ann Barry
Well, I can't let you go, Bill, without trying to get the benefit of your wisdom from decades of success in the sex sector, if you don't mind. And yes, we're at such an exciting moment in tech and also a moment that's causing people to rethink their assumptions around which tech's going to win and which is going to create a new. We're in the middle of the software sector. Sell off. Right. The Saskopolis, to some, they took out other people.
Bill Gurley
They took out doordash yesterday. It wasn't just software.
Ann Barry
Yes, exactly. Delivery. Is this an overreaction? Is this a moment in time?
Bill Gurley
I personally think it probably is an overreaction. But, you know, stock prices are a really interesting thing. I personally come from like the hardcore academic belief in discounted cash flows is what really values companies. And for most of these high tech companies, you know, the next five years, cash flow are a fraction of their actual market cap, which means all the, all the values in the terminal value. So if you all of a sudden say, well, this company might not be around in 20 years, you know, you're, you're no longer going to trade anywhere close to like a 30 or 40 PE. It's going to come way in. And that's what's been happening. What I would say is, I mean there are obviously certain types of software companies where the, that they're kind of information aggregation where the, the AI tool just immediately does what they were doing. And I think those are more drastic. But, but there was someone tweeting Anthropic is a customer of Workday and Salesforce. Like you're paying for this thing. So I don't think there's any world where people are just going to tell the AI to build their finance tracking software because we have the whole process with auditors and like they need to come in and check the books like that needs to be. There has to be some commonality there. And who in your shop is going to do the bugs like analysis? It's just, I don't think it's realistic. And so I do think one day there'll be a great buying opportunity for these stocks. I think you should, you know, maybe. I think there's, there are reasons why we could have an AI correction just because every time there's a wave you end up with speculation and speculators and bubbles. And so when that. If we had an AI bubble correction, I would. I think your listeners should know the types of software companies and others that they like be getting ready with. Kind of a assumption of where value is from a floor perspective could be a huge buying opportunity. Like who's it. You gotta be greedy when others are fearful. And fearful when others are greedy.
Ann Barry
Yeah.
Bill Gurley
Like if everyone's freaking out, it's time to think about buying and start to build your thesis for that.
Ann Barry
And exactly to your point, the learning that comes in beforehand to get ready for that moment, to be ready to be lucky, shall we say, prepared. Just one more thing, Bill, which is we are, we haven't seen it quite yet, but there's been a lot of hope that 2026 is the year that the bumper IPO crop happens again. Yeah, and I was lucky. I went, I interviewed the vice chairman of NASDAQ and we talked about the pipeline. There's lots of excitement. You've been a proponent of direct listings.
Bill Gurley
Yes.
Ann Barry
Talk to us about that, if you don't mind.
Bill Gurley
Well, before I even go to that, I would tell you I think there's a real challenge out there right now in that the venture capital industry has evolved to a place that's fairly industrialized. So there are venture capitalists now that are raising funds that mimic the size of the big PE funds. And one of the things that they've decided to do is to approach the companies, the best in class companies and offer them Money to stay private and allow for secondaries and all these other things. And so you know, companies like Stripe and Databricks, you know, people thought they were going to go public five or six years ago and, and when the Collison brothers talk now, they almost make it sound like they're never going public. And those funds that do that turn around and tell the LPs these are the foundations and the endowments that invest in these type things. You know, these companies aren't going public anymore. So if you want exposure to these growth years, guess what, you have to invest in us. And it's a clever thing. I don't necessarily blame them for doing it. But I think it is bad for America, I think it's bad for retail investors and I don't think the solution should be retail investors investing through those types of vehicles. I think we need to figure out a way to get more companies public. Now to get to the direct listing part. I do think the IPO process itself has been broken for a very long time. Why they do something that's just flat out ignorant in a day and age where we have technology. So if you ask any first year comp sci student and first year finance student to write a model of how an IPO should work, you would allow everyone to bid and you would award the shares to the highest bidder. It's just not like it should just be tautological. Like I don't know why there would be any debate. And by the way, that's how every bond is priced. And that's by the way how all the initial coin offerings work in the crypto world. It's just what you would do. It's not how an IPO works. The way an IPO works is some banker somewhere at some investment bank picks a price in their head. Why would you have a hand picked price when we know how to match supply and demand and then they really only offer it to their top clients which, which, which is just nutty. And emails have been discovered, I've posted them where the banks admit that they're able to use this as candy for. And then you know, and so the retail, you guess what happens the very next day after an ipo. They match supply and demand like I said and the retail investor unfortunately buys into that. And these lucky, well they're not lucky. They're the largest customers of the investment bank are selling into these retail investors. So you see these massive pops like Figma, then it comes way back down. That's horrible for the company that lived through this thing, and it's bad for the employees. And it could have been all prevented by just matching supply and demand from the very beginning. And they've been reluctant to do it. They were dragged into direct listings, I would say, because I spent a ton of time with them. Both the NASDAQ and the NYSE were pushing to get these things across the line, but I just fear there's a regulatory capture of sorts amongst the big banks. It used to be there were way more banks. There used to in Silicon Valley be these group called the Four Horsemen that did a lot of small IPOs, and none of that exists anymore. It's very common to see all three of the big banks on the COVID And so it's really become an oligopoly of sorts. And I don't know how it gets fixed. I hope one day. Sorry for the long answer.
Ann Barry
No, it's a great answer.
Bill Gurley
I hope one day that the people inside the SEC recognize, you know, they love to talk about America has the best financial markets in the world. And I. I think we're. That's not true. When we have this kind of a broken process. And I. I hope they wake up to this reality. It's so easy. You literally, all the direct listing does is. Does exactly what you do the next day and. And only do that. So they take out this step where you hand pick a price and hand allocate it to your customer. And it's worked. We've done several. Both exchanges have applied for a license to do primary raise alongside the deal. Neither. Neither of those things. Neither one has done it yet, but they're eager to do it. And so the thing that might be the pressure catalyst is tokenization, because like I said, the crypto world would never consider not matching supply and demand. It would be, you know, it'd be like, so wrong in that world to even think about not using the technology. So maybe tokenization leads us to a place where there's an alternative pathway.
Ann Barry
And maybe with all these new exchanges popping up, not least in Texas.
Bill Gurley
Yeah, the taxes. I've talked to them about this as well. They could be a protagonist. We'll see.
Ann Barry
I think Bill Galley, I think we've had maybe the next chapter in your career, as you keep learning. I think we've had lobbyist in your
Bill Gurley
future, something close to that, but not a lobbyist.
Ann Barry
There we go. Thank you for joining, Bill. Really appreciate it. Congrats on your book.
Bill Gurley
Thank you.
Ann Barry
Well, huge thanks to Bill Gurley for joining us again. Really enjoy this book. Well worth checking out that's it for today's Brew Markets Daily.
Charles Schwab / VanEck Advertiser
Brew Markets Daily is hosted by Anne Berry and produced by John Croteau, Tarkab Delatif and Emily Millard. Our technical director is Ucheno Ogu. Jim Orzo is our audio Engineer. Booking by A.B. silver. The President of Morning Brew, Inc. Is Devin Emery. If you have any feedback or a company you'd like us to COVID leave a comment or send an email to
Ann Barry
brewmarketshoworningbrew.com have a terrific weekend and we'll see you back here on Monday. Same time, same place. Sam.
Podcast Host: Ann Berry
Guest: Bill Gurley
Date: February 27, 2026
In this episode, Ann Berry sits down with legendary venture capitalist Bill Gurley to explore key themes from his new book, Running Down a Dream. The conversation ranges from the importance of curiosity and lifelong learning, to what makes founder CEOs outperform, to hard truths about the venture capital industry, the IPO process, and how investors should approach current volatility in the software and AI tech landscape. The discussion is punctuated with Gurley's practical career advice and candid takes on where public markets and tech innovation are headed.
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The discussion is fast-paced but practical, intellectually optimistic, and draws on vivid real-world examples. Gurley’s insights are candid, constructive, and actionable—he’s both a critic and a coach. Ann Berry’s questioning is incisive yet conversational, pushing into both the “how” and the “why” of career and investment advice.
If you’re thinking about your tech career, your investing strategy, or where the stock market’s future may lie, this episode delivers a wealth of actionable wisdom—especially valuable for anyone anxious about AI or frustrated with how public markets currently work. Bill Gurley’s advice: stay curious, keep learning, build your network, and, when chaos hits, have your playbook ready.