Bill Gurley on Broken IPOs, Founder CEOs & Buying the AI Dip

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For Friday, February 27th, it's Brew Markets Daily and I'm Anne 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 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 Satya Nadella 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 competitive 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 for Bill's 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.

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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.

Yeah, I told my wife, I don't normally wear suits, but I'm going to today. Well, here it is.

So we've got it in the Brew Markets 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 shrug 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 fuels long-term commitment to a path.

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, 'Whew, 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.

It's hard, and you called it a skill set, which is sort of interesting, as opposed to the sort of natural thing that courses through people's sort of veins. 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?

It could possibly be taught. And so many of the greats, you know, whether Buffett, too—I just saw a long podcast with Tobi from Shopify. And they're like, '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 flipped for me. So I would like to think that that could be true of anyone. And once I started consuming books, it became addictive.

And I'm still a vast reader today. At the back of my book is a list of books—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 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 Carlsen, he says, you know, he says, 'I hate grinding through exercises, but I love learning about my craft.' And he's read all these history books on chess. He devours the information, but on his own terms.

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 minute—those who are founder-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: Amazon, Tesla, NVIDIA, Meta, Shopify, AppLovin. Do you have a perspective on that?

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 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 curiosity about what they're doing. So any, you know, I was just listening to Bret Taylor talk about Sierra, this new AI company that he's running, and he—he obviously has spent the past three years repotting himself as an AI executive. He's out there every day testing what's possible, studying what's possible, and all the great founders do that.

There's a great book, The Innovator's Dilemma, that explains how founders disrupt other industries, and the key thing is, that enables that is when a new wave comes along, they are on the front of understanding it and what's possible and how to use it. And that's the skill set that allows them to be successful.

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?

I do. And I would offer you what to me is a stark contrast 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.

Most people. Yeah.

We found this Gallup poll from 2023 that said it was over 50 percent 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 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. 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 what it's capable of because they're out there testing it every day.

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, of course, we have podcasts and YouTube interviews. Like, 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.

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.

Yeah. My book wasn't written as an antidote to AI unemployment writ large, but I would say that—well, I want to back up real quick. I do fear that 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. And we start packing their day and their schedule with chess lessons and cello lessons and lacrosse lessons and volunteering at the SPCA 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 creative activities, you know, and really trying to identify the thing that you're passionate about.

And others have talked about this. Rick Rubin's talked about it. I've talked about it. And I fear that the kids are taught to grind. And, 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, that was what I grew up with.

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 drudgery. And so anyway, I think that's also part of the problem. 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.

Let's take a break. When we come back, more of my conversation with Bill Gurley.

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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—I hear your Texas drawl, by the way, and I read that quote—and it also came together for me. But I think, you know, look, I remember, 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.

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.

Yeah. So, you know, I was on a podcast where we were interviewing Satya Nadella at Microsoft. And I think it's hard to put what Satya has accomplished in context because it's such an outlier. Most companies, once they get big and have had an extended period of degrowth, like where they really slow down, they never come back. Like they never get back to glory. And I think that's been... Like, 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 do you 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 said 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 quickly, you know, and it's super impressive.

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.

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 gets stuck in one place. I think it's a bit of an elevated... assignment just for—for the—for your listeners. Like, 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.

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. Yeah. 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.

Yeah. Well, I mean, in his famous Stanford graduation speech, Steve Jobs makes this argument that 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 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, these podcasters interview, 'How do 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 ability.

energy to do multiple companies simultaneously. So I don't know if we can go recommend it for everybody.

Well, you've been in the position of hiring CEOs or 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?

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 helping to lead the company. And that is a common practice.

I want to talk a bit more about one other suggestion or principle in the book, which is to go where the action is. Yes. 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. It's the center of the globe, and I moved over.

I did the exact same thing in 1993.

That was it. Go where it's happening.

In the digital world, there has been a lot of talk about democratization of access. Yes. And AI, frankly, would be the next incarnation of it, right? Do you still have the perspective that going geographically where the action is?

Yeah, and I'll tell you why. But you just said something that I want to double-click on. You talked about 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, you know, 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—you know, 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 where this stuff's taken us. But, but no, I fundamentally believe that if you are certain what you want to do, um, 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, um, have this innate fear. They think 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'll be okay to be a big fish in a small pond, which, which, and I disagree with both of them.

And, and, 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—the probability of lucky events goes way up. Yes. 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 industries, 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 so anyway, yes, go, go, go. I'm glad you went. I did the same thing. That particular chapter, this book started as a presentation I gave at a university, and that tenet wasn't in there.

And we added it. And I'd say it's the one, of the people that read the book, that gets the most attention.

I thought, actually, as I was reading 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? PayPal, let's look at the PayPal Mafia. Peter Thiel, Elon Musk, Max Levchin, Reid Hoffman, David Sacks, Steve Chen, Chad Hurley. I mean, and then there's an Amazon Mafia too, actually, now, if you take a look at Marc Lore. You take a look at Eric Ferguson.

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 if 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.

Well, Tony Fadell is one of them who's profiled in the book. But, but anyway, go watch it. Like, 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 bit of, I think it's like a positive impact. I don't think of it as competition, but when you see other people doing certain things, it raises the bar for you.

Yes, 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, um, that's just another reason to get out there and get in the epicenter.

Well, I can't let you go, Bill, without trying to get the benefit of your wisdom from decades of success in the tech sector, if you don't mind.

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 chapter. We're in the middle of the software sector sell-off, right? The SaaSpocalypse, to some.

They took out other people. They took out DoorDash yesterday. It wasn't just software.

Yes, exactly. Delivery. Is this an overreaction? Is this a moment in time?

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. It's what really values companies. And for most people, these high-tech companies, you know, the next five years' cash flow are a fraction of their actual market cap, which means all the value's in the terminal value. So if you all of a sudden say, 'Well, this company might not be around in 20 years,' you're no longer going to trade anywhere close to like a 30 or 40 P/E. 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

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 there was someone tweeting Anthropic's a customer of Workday and Salesforce, like, they're paying for this thing. So I don't think there's any world where people are just gonna 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 bug, like, analysis? It's just, I don't think it's realistic. And so I do think, um, one day there'll be a great buying opportunity for these stocks.

I think you should, you know, maybe, 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 if we had an AI bubble correction, I think your listeners should know the types of software companies and others that they like, be getting ready with kind of an assumption of where value is from a floor perspective—could be a huge buying opportunity. You've got to be greedy when others are fearful and fearful when others are greedy. If everyone's freaking out, it's time to think about buying and start to build your thesis for that.

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?

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.

Yes.

Talk to us about that, if you don't mind.

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 companies like Stripe and Databricks, people thought they were gonna go public five or six years ago. 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 of 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 should just be tautological. 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 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... 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 who's selling? Well, they're not lucky. 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, 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 this 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 cover. 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. No, it's a great answer. 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 think that's not true when we have this kind of a broken process. And I hope they wake up to this reality. It's so easy. All a direct listing does is, does exactly what you do the next day, and only do that. So they take out this step where you hand-pick a price and hand-allocate it to your customers. And it's worked. We've done several. Both exchanges have applied for a license to do a primary raise alongside the deal. 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 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.

And maybe with all these new exchanges popping up, not least in Texas. Yeah, the TXSE.

I've talked to them about this as well. They could be a protagonist. We'll see.

I think, Bill Gurley, I think we've had maybe the next chapter in your career as you keep learning. I think we've had lobbyist in your future.

Something close to that, but not a lobbyist.

There we go. Thank you for joining, Bill. Really appreciate it. Congrats on your book.

Thank you.

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.

Brew Markets Daily is hosted by Anne Barry and produced by Jon Croteau, Tarek Abdel-Atif, and Emily Millard. Our technical director is Uchenna Waogu. 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 cover, leave a comment or send an email to brewmarketshow@morningbrew.com.

Have a terrific weekend, and we'll see you back here on Monday, same time, same place.

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