Tech Brew Ride Home - (Bonus) World Cup Of Entrepreneurs Part 1

Episode Date: May 15, 2025

Who is THE entrepreneur of the Internet Era? In this episode, we cover the round of 16 matchups as voted on by YOU. (Originally posted November 2021) Learn more about your ad choices. Visit megaphone.fm/adchoices

On April 4th, 2023, around 2 in the morning, a man was found stabbed multiple times on a sidewalk in downtown San Francisco. Hey, who did this to you? What happened next turned the story into a political firestorm. Reports have identified the victim as Bob Lee, the founder of Cash App. From Bloomberg Podcasts, this is Foundering, the Killing of Bob Lee, beginning April 16. Welcome to an extremely special episode of the TechMeme Ride Home Experience. I'm Brian McCullough as always. And my co-host, as always, Chris Messina is here.

Chris. Howdy, howdy? Glad to be here. I'm very excited to be part of this World Cup of Entrepreneurs. That's right. This is something we've never done before. I think it's going to be a lot of fun. The whole process thus far has been a lot of fun.

but we are going to figure out who the Ney Plus Ultra entrepreneur of say the last 30 years is and to help us do that we have the boys from the Acquired podcast and I'll let them introduce themselves individually like Ben you go first

Brian thanks for having us feels like we've got the super group of podcasters here so excited to be a part of it Hey, everyone, I'm Ben Gilbert. I am the co-founder of Pioneer Square Labs, a startup studio and venture fund in Seattle, and the less dulcet tone half of the Acquired podcast co-hosted by my co-host David. First in our hearts. First in our hearts. David over to you. I'm David Rosenthal. I am the more dulcet half of the acquired podcast,

I guess. Thank you, Ben. I'll use that from now on. I'm an angel investor based in San Francisco. And yeah, thank you, thank you guys for having us on here. This is going to be so much fun. Anybody who listens to Acquired knows that we do like insane amounts of preparation and like everything is scripted to the like T and like, not like word for word scripted. But we love doing stuff like this where we get to just like pontificate without doing research. So thank you. Well, and let me say that Ben and I were talking. I think it was five years ago.

We did an episode together early on in both of our podcasting careers. And I want to specifically mention this because I listened recently to your two-part history of Andreessen Horowitz, where you were kind enough to mention some of my early research from the Internet history podcast. And I do have one bone to pick with you, too. Oh, go for it comes. Here's the problem. You guys figured out. I'm glad we're getting the arguing out of the way now so that we can all agree on the picks.

You guys came up with the concept or the term that Al Gore was Mark Andreessen's VC. And that's like the most perfect way to put it. So I'm pissed at you guys because I did a whole episode about like, did Al Gore really invent the internet and things like that. But like I remember that one. Putting that in those terms was cute enough that I wish it was in my book. I wish I had thought of it myself. So screw you guys. Second edition.

Second edition. Yeah. Okay. Thank you, Brad. Yes, yes. I listen, the Acquired podcast is not an acquired taste. It is an essential listen. And I couldn't recommend it more highly.

Okay. So a lot of people, most people, would be regular listeners to the show. So you would know that over the last two weeks, we have been doing a World Cup of Entrepreneurs sort of Brackets voting thing on Twitter. 16 entered, only one came out of the Thunderdome. And essentially what we're going to do is go through each of the matchups and we're going to talk about the person that lost in that matchup and that will allow us to eventually get through everyone until we get to the one that was left

standing. By the way, Brian, when you first explained that to me, I was like, it didn't quite make sense. And then I realized, oh, because in like the NCAA tournament of 64, there's 63 losers. So if you just talk about the losers enough, you eventually cover all but the winner. All of them. Right. Well, and the only winner that, well, right, that we'll talk about when they win, the person that we talk about last will be the winner, right? So that's a way to queue up that we're going to have to talk about. Everybody's got to listen to the end. I like this. Right, right. Exactly. So, right. We have our first.

matchup, and we're going to talk about the loser of that first matchup. The first matchup was, and by the way, this was voted on by listeners on Twitter, randos on Twitter, people on Twitter. The matchup was Evan Spiegel of Snap, Snapchat, whatever you want to call it, versus Reed Hastings of Netflix. Reed won this, 84 and a half percent to Evans 15 and a half percent. And so again, what we're going to do is talk about Evan first. And here's how I'd like to kick it off. I kind of feel like this should have been closer. We can argue about why it wasn't closer.

Here's my bull case for Evan Spiegel as a great entrepreneur. How many people have created product? What would be the term, Chris? What would you call like stories or even before that, like, you know, ephemeral messaging and things like that. It's a new medium, right? That's what it takes advantage of an emerging technology as that technology is still being deciphered or used. He's like the chief product officer for the internet. Right. Well, for Facebook, certainly. Yeah, right. I mean, it's almost better than Jack Dorsey, right? Like, you know, he doesn't even get to be CEO of both companies. Now, do we know,

I mean, I guess, does anyone know the story behind that? Like, it's not necessarily that Evan is the one that came up with stories or ephemeral mess. I mean, obviously, you know, know, early on, ephemeral messaging as the, as the, I think what Evan probably gets credit for is opening to the camera by default. And so every other, and part of this had to do with, I think the iPhone getting to a place where it was stable enough, where, you know, the camera wouldn't crash and stuff like that, and it was performant. And so that was just unorthodox, because you kind of had to like first start with content.

And then it would load a feed, typically, whether that was Instagram or it was Facebook or Twitter. And then, and I, And also remember, the assumption was that people were more consumers. You know, the 90-10-1 rule of social media is that 90% of people are just there to consume. And, you know, 1% of the people are actually content creators. This changed that whole dynamic by turning the camera into a communication device. And assuming that a new and younger generation would find it easier to communicate visually through the camera,

as opposed to sending text messages or anything else. So that was, you know, I don't think it's enough to say stories was the innovation. It was really thinking differently about communication from a generational perspective. Oh, man, that's such a good point. Like, before Snapchat, yeah, like, it really was, you know, I think now about, like, the percentage. Actually, well, I don't know what the percentage of producers versus just consumers, is on like Twitter or Instagram or like, but like, no question in my mind that it is vastly higher than it was pre-Snapchat and it is all thanks to Snapchat.

Yeah, right. Yeah. And also I think like there was like a preciousness about photos before where if you took a photo, especially if you were coming out of like the Kodak era where you actually used film, then every image that you took needed to be something that was like good and worthy. And everything that you shared on Instagram, Instagram was curated. And so this, like the ephemorality was a kind of response to the abundance of communicating through visual images. So it really didn't make sense to hold on to everything anymore. Whereas before it was, you know, sacred to have these digital artifacts, what I think Evan realized was, you know, we don't save all of our phone calls. So why would you save all of your,

you know, photos that are being shared? Ben, let me let me ask you this on a straight. entrepreneur sort of level. Evans also famous for not selling to Mark Zuckerberg. And like, let's think of that from the pure entrepreneur standpoint of turning down billions of dollars, being the being able to say no and being like, I'm going to build a social media company that will thrive. It has been thriving. And as an entrepreneur, we remember when Snap's stock recently,

was in single digits and things like that. To have those diamond hands to use common parlance now, to believe in your vision, like, that's a rare thing. Yeah, and the grand irony of it all is that maybe the only person who has performed that same exact act of saying, no, I'm going to go build a social media company of my own that's going to be worth billions, multiple billions, maybe even trillions,

and I'm going to turn down your billion dollar offer was Mark Zuckerberg just a decade before. And, you know, the famous, of course, crying in the bathroom after turning down the billion dollar offer by yacht. Vomiting in the bathroom. I can't, I'm sure there may have been many other things. There are lots of bodily. Lots of limited. No, but, but, you raise a great point. And even very recently, like I just looked it up, Snap is a $116 billion market cap company.

People had counted them down and out. obviously so many times. But think about when Instagram launched stories. And there was sort of that admission to Chris's point that, geez, Instagram is a museum and Snap is a bar. And the bar is way more fun to hang out than the museum. And of course, we're losing a lot of users to it. And of course, they clone stories.

And what that did in the three, six months after cloning stories was Snap had penetrated the U.S. in a big way. And Instagram launching this basically cut off the needs. for people to ever download Snap internationally because they could get the same functionality out of Instagram where they already had that multi-billion dollar install base. And so it is really amazing that despite that just gnarly move by Facebook and Instagram to cut off that growth opportunity, there's still a hundred billion dollar plus company now and I've overcome it. Let me play the pundit here a little bit, like a sports pundit and say that, you know,

I think that this is a, the result is a bit unfair to Evan. Like, I would, if I were the one, you know, voting, I would say that he probably should have advanced further in the tournament. For all the reasons just said, but then also for that last bit, too, about how, you know, it's not just that he has a company that, that, that, that, um, reach a scale, then goes public, but then also has troubles and then can, can theoretically fix those troubles and, and, and continue to thrive. and things like that. I'm going to move on to play. One quick thing before I move on. Yes, go ahead, David. Yes, please.

Just met a point that I think we talk about this. We've been talking about this a lot unacquired recently, but Evan and Snap is such a great example to me of why startups are important. You know, like, it would be such a sad world if only Facebook could only be the only ones innovating and social because none of this ever would have happened. And it's better for everybody. Facebook would have Evan not had Diamond Hands own Instagram and Snap. You know, so like it's almost like.

And that was before stories, right? So like, yeah, no stories if that happened. So it's almost like Gandalf's style, Evan was the one that stood there in the breach and said, no, this era is not going to evolve the way that you think it will, you ballrog you. David liked that one. All right, I am moving on to try to produce this as best I can, so we're not here for five hours. The next matchup was Jack Ma versus Jeff Bezos. And I kind of randomized the matchups, but then if I saw a theme that worked, I wanted to do the theme.

Jeff Bezos won 74% to 26%. But I wanted to match them up because in a way, the cheap thing to say about Jack Ma is that he took the Bezos playbook and took it to China. Not just the Bezos playbook, but the Silicon Valley startup playbook. Thoughts on that as a theme for matching up? I think the easy and dare I say lazy take is you're comparing Amazon to China's Amazon. And I think the 74% voting for Jeff Bezos and the 26% voting for Jack Ma is frankly representative of who follows you on Twitter. The sample size. Yeah.

And the sample source. I mean, we could. Look, I think Jeff Bezos should win this. Like, look at market cap alone. I think. Well, this is like getting seated against, you know, like Duke in the tournament. Like, you know, Jack. It's an unfortunate.

Hold a rough draw here. But I think it's worth acknowledging what a different company, Alibaba, is than Amazon. I mean, the biggest one is their B2B business. I mean, Alibaba moves a tremendous amount of merchandise through a B2B e-commerce experience, of which doesn't really exist in the U.S. yet. Like, Amazon business is a thing, and you can order from it as a business. But the B2B commerce market is much larger than the B2C commerce market. And Amazon has not been successful at shifting e-commerce online for B2B in the U.S.

Yeah, Alibaba has a sales force for their core marketplace. Like Amazon doesn't have a sales force for their marketplace. And I mean, look, in theory, the, you know, Jeff Bezos also was early in a market. But, you know, Jeff Bezos is early in a market in the West, in the U.S. or whatever. Consider the also complicating factor of Jack Ma bringing entrepreneurialism and, you know, the Silicon Valley style entrepreneurialism to China in the late 90s and early 2000s. Like that is breaking ground that is, you know, apoccal, essentially. I think one thing that's missing from this a little bit, though, and this is more my ignorance,

I think more than anything, is I don't know what sort of business practices or concepts Jack Ma sort of brought to the world that then were socialized and popularized elsewhere. And one that I'm thinking of particular, and this isn't meant to sort of be, you know, singing Bezos's praise, but the way in which like Bezos sort of required product direction to be done through written testimony effectively, to sort of write the whatever the three-page document, have people read it in silence, and then to socialize that. I don't, I mean, I'm sure Jack Ma had very similarly powerful and important tactics. But I wonder to what degree those tactics were. actually adopted by other companies in China versus the way in which Amazon and its aggressiveness and some of its techniques were socialized within the American business. Have you guys done Alibaba unacquired? Pardon my ignorance on that. Yes. It was a few years ago though. I think we make it called out for this for people that know better, but I think it's fair to credit

Jack Ma with popularizing the 996. I think that, yeah, the notion that like Chinese companies move much faster than their American counterparts. I was going to say, you should unpack that a little bit, like for the listeners, because I know that it's something at TikTok that is current today. So maybe that is an example of that cultural phenomenon that was socialized. So what is that? Working 99 hours per week. No, no, 9 a.m. to 9 p.m. 6 days a week.

Yeah, 9 to 9 6 days a week. Which I don't, maybe that is around 99 hours. It might be about 99 hours. I don't know. Yeah. More than 40. Just like, we will win because we will outwork our competition. And of course, in such a competitive country where you have so many people, you have the very recent rise of the middle class,

you have special economic zone. So, you know, capitalism in a very small and different way is very new to the country. You know, you have a whole bunch of people pursuing an opportunity concurrently. And the reason that everyone's so focused on a single opportunity is a top-down mandate, the country deciding, the party deciding that, hey, this is one of five categories. It's very important to us right now. And so when you have someone like Jack Ma that's sort of saying, well, we're going to win by working this absurd amount, and of course, this is a couple decades ago, it then sort of raises the bar. And when you have so many people competing, they're all going to be at that bar. And you end up with the sort of state of startups that you have in

China these days. I'm going to move on real quick because I, you know, Jack is having issues. I just want to say that Jack. You mean vanishing issues? Yeah, I was going to say. Yeah, that's the problem. Jack was the first sort of face of like, you know, Silicon Valley style tech startup entrepreneurship in China.

And he also might be the first one out to pasture. I don't know. moving on to matchup number three because that is our first upset. Now, if you're looking at the email that I sent you, I got the numbers wrong. The matchup is Mark Zuckerberg versus Jack Dorsey, and Mark Zuckerberg loses. Jack Dorsey got 71.1% of the vote. Mark Zuckerberg only got 20. You did this on Twitter, so.

Okay, understood. You're saying Jack logged in and tip the scale? Well, but look, to bring, you know, David mentioned seeds. Like if I had thought of this as a seeded tournament, for sure Mark Zuckerberg would have been one of the seeds, right? I am genuinely surprised that Dorsey beat Zuck. And if you hosted this on Facebook for the poll, I wonder if anybody would have actually participated. Okay, well, all right, maybe. I'll tell you what, let's address, let's address the upset first, and then we can give

Zuck his do as an entrepreneur at the end. Could it just come down to people don't like Zuck? Yes. Likely. I think if you had run this poll in 1994, and you had Bill Gates in there, like Bill Gates would have gotten unseated in the first round, too. Well, now, having said that, Jack Dorsey is not exactly known. There are people that don't think Jack Dorsey is a great business leader, decision maker. So in a way, I don't remember if I consciously put these two against, I think I put these two against each other because Twitter represented the first sort of threat to the social media model that Zuckerberg had created. But at the same time and you can argue that Jack of course has created two companies. So I guess maybe if I'm

if I'm going to play devil's advocate, the argument against Zuck as a great entrepreneur would be that he had one good idea. Now you can argue that's not even true. That's not true. Okay, Chris, take it. He didn't have any ideas. He had wirehog. That was a good. I'm pretty sure that was built on Napster or like I mean honestly, to give Zuck his due, he's probably the best at stealing ideas and surfing behavior and seeing what's happening next. I mean, he is, you know, like I hope he and his airs never hear this, but like he's probably like the least inventive person ever and yet the sort of smarmiest of them all by monetizing, capitalizing, and building on that. Like he is truly Bill Gates the second coming. He is like Caesar's heir, you know, given that he wants to build an empire. This is the World Cup of Entrepreneurs.

This is the World Cup of like nice guys. I mean, what's the goal? I'm just, look, people voted on this. I'm not saying the people who are right or wrong. I mean, you know, Zuckerberg is the guy that would shank you, you know, if he got the chance and then, you know, claim that it was the Snapchat guy. Yeah, but I'm with Ben there. Like, that's what an entrepreneur should do. He should be willing to shank.

The consequence of that is people aren't going to like you. And so you're going to lose Twitter popularity contest. So there you go. I think Zuck doesn't care. I think so. Yeah, I think so. Let me, let me, I guess is this playing devil's advocate for Zuck? There's a famous story where when Zuckerberg turns down the Yahoo offer or the one of,

one of the many billion dollar offers, he says the reason that he's going to turn it down is because if he did take the money, he just take it and start another social network and he already likes the one he has, right? Okay. This is probably not going to help his case. there are certain entrepreneurs that can see clearly one vision and can execute it on it perfectly, whether it be you're Rockefeller and you see that oil is going to power the 20th century. Ooh, next acquired episode foreshadowing.

Okay, there you go. So it's like there are several cases. Like, who's the guy in New York real estate that just realized that Manhattan is an island? So you buy real estate. It's eventually going to go all the way to the top. It's like having that vision and executing on it and not wavering from it, that is kind of the sign of a brilliant entrepreneur. Yes, and I would even add onto that, a similar sign of a brilliant entrepreneur is being willing to do something that you see as the future when nobody else does around you. That is the story of Zuck, like the whole time, you know, not dropping out of Harvard.

That was like, wow, that's crazy. Who does that? You know, not selling the Yahoo. That's crazy. Going public at $100 billion valuation, crazy. And everything happening now. David, let me, let me point out that again, this comes right after the dot com bubbles bursting. There is not a precedent for people, again, to use the term diamond hands, for being that brave.

You should take the billion dollars and run. People did, you know, like the fact that that Amazon was until recently still controlled by its founder, think of every other company that was founded in the 90s. That is not true necessarily. So like the fact that he was the first, I would say that Mark Zuckerberg is the model for the modern concept of an entrepreneur. Yeah. I mean, the social network inspired so many people. It was the liar's poker of like our generation. Dude, for like five years when I would write code, I would do it to the social network sound track.

Totally. Yes. Chris, you were shaking your head when David said that. Yeah, I just, you know, one of the reasons why I think the Twitterverse may not have been wrong is because I just can't think of Zuckerberg as an entrepreneur. Like, he, he's an empire builder. Like, he and I play civilization. What is an entrepreneur then? No.

Like an entrepreneur, like it's French and basically it's, you know, someone who, you know, makes bread and like, you know, from strange ingredients they have lying around. Like to me, Zuckerberg, you know, saw the map as black and wanted to painted blue and, you know, by moving his troops around. And so to evaluate him from convention, like what Brian's saying, yeah, like most of the time founders will leave after, you know, their 10, 15 years stint because they're bored or they're tired. They want to do something else. That has never been the case with Zuckerberg. Z Zuckerberg has always wanted to. expand his empire. All roads lead back to Rome. The Facebook Connect, Beacon, all of the things that he built into the platform were about expanding the influence as a dominant power. And I just can't evaluate him on the same, you know, kind of public company set of principles that I would other entrepreneurs. Can I, I'm going to put a pin on this one unless someone has one more thing to say. But I'm, you know what, Chris, I don't know if you and I have influenced each other on this, but I've come around to psychoanalyzing Zuck that way, where I believe the theory that he played civilization and he loves civilization and he knows that he can't be a modern day Julius Caesar. He knows now he can't run for president. But he knows that also.

He is a modern Caesar. He is doing it. He's doing it in the modern way. And so you don't need an army anymore. You just need people to log into your website. You know, there's that line and he was a stiff nut growing up. A stiff nut? He was a nut about civilization.

Right. Yeah, he was. He said it in interviews, yes. That's awesome. So my theory to psychoanalyze him is. And also, he studied the classics. Right. Only, like, courses that he actually, like, finished in college were about, like, the Roman emperts.

Literature and Latin and, like, all that stuff. So my theory is. Maybe I'm typecasting too much, but I just, I can't let that idea go. No, I'm with you. This is, I've. come to this conclusion is that, you know, because the really lazy thing to say is, well, why, you know, if I were in his position, I've got all these billions of dollars, I'd, you know, date beautiful people, I'd buy yachts and stuff. Why does he still go to work every day? It's because there's that line in the movie Heat where for me, the action is the juice.

One of the robbers says that to somebody else. The action that is the juice for Zuck is people have to play in my game. People have to play in my world. Why does he care about if you have to do your banking via the cryptocurrency he creates. Because that's the juice for him. That's the juice. He hangs out with like Jay Z's like votes and stuff. You know? Like Zuck's like he does like little photo ops in Hawaii.

It's like you make it look like he's like, you know, an American or something. Like you know, he's like, I just have to do this. Versus grilling meats or something. So your guys argument to sum it up is is that Zuck is Caesar but not Romulus and Remus. Yeah. Right. Ben, what were you going to say? I, it's almost like we first have to define what even word, what the game is here.

Because the most extreme version of my argument is, well, let's just go look at the market cap of all the companies that all these people found it. And then we have an answer and we don't have to have a conversation here, which, you know, it is a, which is one definition of success. But B, like it doesn't take the creativity into account. Chris, what you're sort of arguing is like part of entrepreneurship is, you know, having an initial idea and then seeing that idea through and making something people want in YC's parlance and then, you know, figuring out how to both capture value from what the thing that people want, but also create a ton of value in the world. And I think your argument is basically like, not really sure this guy's growing the pie, but he sure has captured a lot of it. Yes. And also he's, and I think this is the last thing I'll say on this is that he has changed behavior. And that is the hardest thing to do in the world, which is to get people to go along with the way that you see the world and then to go and to embrace it. And all along, every step of the way, people have resisted the vision that Zuckerberg presented. And yet they went with it anyways. Like the news feed was the first example of this where the whole team, like after there was like literally protests in the streets.

Palo Alto against the news feed and it started the whole complication with privacy oh no he's he doubled down you know he had his troops of you know his 300 troops with like boss and like the rest of them they had their shields up and their spears and they came out and they decimated the whoever it was they were fighting the jibians that um or who who was making the argument that he is just the best at looking at the data and understanding yeah that was chris right or somebody yeah Well, that's how I say. He basically is like observing because, one, he's created the system to ingest all the data to see how young people are operating. And then he basically takes that and then makes it easier for them to keep doing what they're already doing. So we saw people looking and snooping on each other's profiles. And he basically productized that creepy behavior. And so then everyone's like, you know, it's like dogs. Right. Like what you really want to do is you want to have like some, I don't know, this is going to get really weird all of a sudden. But, you know, like the dogs just like sniff each other's butts. Like humans do the same thing in different ways. like their profiles. And so he just built that system that automatically updated you. So whenever there was a fire hydrant that was peed on, you got a notification. That's Facebook. Oh, that's so good.

Anyways, can we do one real quick digression before we move on? The battles on the streets of Palo Alto made me think of this. Did y'all see the social dilemma? I'm in it. Yeah. That's right. You are in it. Oh, wow. Okay, okay. It's like a cameo for like two seconds. This is the perfect discussion. want your thoughts on. Great movie. But then the end of it, right? Where there's like the mean streets of Palo Alto and the kids get rolled up and like they're getting, I'm like, I lived in like someone gets pushed down. That is not going down in Palo Alto. I do not believe it for a second. I mean, honestly, it underwine the whole movie, you know, it's sort of like, it's like the Sandy Brook thing. It's like this is, this is not. Anyways, I have a lot of problems with that movie. And I think, you know,

it's one of those things where it's important to raise the alarm to some degree, but the lack of personal accountability, you know, that the movie sort of ticks away. And then at the end, it's like turn off notifications. It's like, like,

okay, not realistic. So. Or you're going to go to prison in Palo Alto? Right. Right. All right. Let's move on.

Yes, being the producer and moving on here. The next matchup was Katrina Lake versus Elon Musk. And this is one of those. again, which maybe was an unfair matchup, except I will say there were way worse losses in terms of the percentage. Elon Musk won this matchup, 78.1% to Katrina Lakes, 21.9%. Ben, I think you might have been, when we were soliciting for who the 16 should be, it might have been your idea to include Katrina. And I can make some arguments for why I wanted to include her.

her as a representative of a bunch of things, but make your argument for Katrina as a great entrepreneur. Yeah, I think, I mean, she's just built an unbelievable business in Stitch Fix. I think there's a few, like, if you look at her personally, I think she has this unbelievable combination of left brain, right brain, where she is so, like clear on how all the financial statements. Like, she's financially savvy in a way that I feel a lot of founders sort of glaze over it. Like, most of the time when a seed stage founder is pitching for venture capital, they're not speaking ever in terms of cost of capital. If you're like, actually, it might be cheaper to raise debt than equity if you make a few assumptions. Like, most entrepreneurs are going to be like,

huh? What do you mean? Do I get the money or not? I get the sense that Katrina has like always been an extremely financially savvy operator in addition to like having that Genesecois that a founder has of to use it again, making something people want. So like, first of all, I just have... Stitch fix. If we didn't, I just wanted to make sure that we said that. Oh, good point. Stitch fix. Yes. Sorry, go on. So that's like about her personally. Now, Stitch Fix as the business, I think, has just blown away everyone's expectations of what it could become. I mean, I think there were a lot of clothing upstarts in the last 10, 15 years that had subscription boxes or had, you know, the trunk club was one that sold to Nordstrom.

And this one, like, it just had so much more life and running room because of the way it integrated technology and like physical things in the real world that people need on the day-to-day basis. So I think there's a big component of the business was hiring a lot of the people that built the Netflix recommendation algorithm to sort of be the data science arm of Stitch Fix. And I've just been continually surprised, you know, year over year that this business continues to grow, continues to grow quickly and hasn't been a flash in the pan. Anyone else, David?

Yeah. I mean, to Ben's point, you know, I'll see, you know, there's a, there's so many definitions of entrepreneur, right? But one other thing that Ben, you referenced, but that Katrina did, I think we talked about this a lot on our episode about them that most founders don't, certainly didn't in her era. She was so incredibly capital efficient. Like she, I mean, I remember I interned at Meritech, which is a great growth firm in Palo Alto when my summer in business school. and we were like, you know, oh, Stitch Fix, like, what a great company. Like, we got to get a, they're raising around and like, nope, not raising around.

Don't need the money. Their cash flow positive, not going to sell equity. And like, that was so, you know, contrarian at the time. And, you know, she didn't need it. She protected her cap table. And like, you know, it's done amazingly well. My argument for including her, and I know this is not an easy fit is because it's not a D to C company.

It's not a direct-to-consumer company. Sure it is. Well, not in the perfect sense of like, you know, Warby Parker or something. It sort of rides that line between, like we've been saying, like the subscription. It's a retailer. Right.

But the modern retailer where it is, you have that very close connection with your consumer. You have the subscription aspect to it. So I thought that she was a person. perfect inclusion because she sort of melds all of those parts of like what modern commerce is and modern brands are. I mean, it also feels like, you know, she was so good at understanding like the consumer, understanding the problem space, understanding technology. And in this case, like a good entrepreneur, being able to go all the way, you know, from soup to nuts, as they say, sort of from like the

the highest level of the business and how to operate it down to the individual experience of getting the box and opening it and, you know, dressing yourself. And then the whole. process of data enrichment. I mean, this is, you know, when StitchFitch was really coming up, it was pre-machine learning and a lot of the techniques, you know, that Amazon and others have embraced to get better over time about how to create fashion that people, you know, want and that fits their style. Like that is something that I think she productized and brought kind of a, what's it called? They make cars. They make cars on an assembly line. It's sort of like an assembly line of fashion. And so bringing all those things together.

in a new conception of how commerce could happen, I think, is really like the core insight. And so I don't know. I liked what you guys said. And I think, you know, she definitely is one of those underappreciated female founders that deserves a whole lot more credit and credibility. Yep. Because I'm the one who suggested it, I'll close the book and move us along here. Ultimately, like she's up against Elon Musk here.

Elon Musk is the clear sort of winner in particular because Stitch Fix as a business is just not in the same category at all as any of these other businesses. businesses in terms of the scale and impact of it, particularly both the combination of SpaceX and Tesla. Yes, but as in World Cups, sometimes Australia goes against a Brazil. And as much as you might love Australia because they're great players and they play great football, I guess it's just sometimes you're playing Brazil a little bit. But the next one is the closest voting that we had. This is so close.

It is literally, I believe, one vote decided this. And the matchup was Patrick Collison versus Oprah Winfrey. And Patrick won by 50.4% of the voting versus Oprah's 49.6% of the voting. I don't know. So close. This is another one. This one went into triple overtime. Well, but also as a pundit, I feel like, you know, I feel.

I feel like Oprah really should have won this one. She's robbed. Not necessarily robbed, but I'm going to... She's doing pretty well for someone who's been robbed. Fair, fair. Well, right. She literally lives in the promised land. We're going to talk about Oprah right here.

I'm going to toss to David. I know why Oprah should have gone farther in this tournament, but if you've got, team me up on Oprah. Oh, well, this was one of the most fun acquired episodes that we did. When did we do this, Ben? Last summer, I think a year ago. Yeah, a year ago. Oh, man.

Her story is just like, it is unreal. I mean, talk about like an entrepreneurial story. I mean, she came from like literally everything in the world stacked against her. I mean, she's born in America, right? Like, that's one card in her favor. But that was like the only card. her favor. I mean, broken families, sexual abuse, got pregnant at 15, 16, I think, very, very young, just unreal odds growing up in the South as a black woman at that time and became Oprah.

And the two like chapters after that are when you say she became Oprah, it's worth noting the entertainer that she became. Like, I actually pulled the stat from our transcript at peak, and this is before YouTube. This is before DVRs. So these are actual concurrent people tuning into her show. 44 million people would concurrently tune in to watch Oprah. Like, who captures that kind of live attention,

like on an every afternoon basis? Like, just an unbelievable amount of aggregation of attention. But the... I think any of these streamer numbers, like, nothing compares. No, no way. I mean, truly, unless you're at, like, international sort of like China scale. Like, I think, like, the League of Legends, you know, international, like, worlds, I think might, might compare. To your point, the way in which people would watch television, you know, in that era, I feel like it was a lot more engaged.

You know, it was a lot more like lean forward, like solely focused on that attention because there weren't all these notifications. There wasn't chat. There wasn't all these other ways to be involved. Well, but actually, that's actually why I think she's important to be in here because, you know, people might say why in a theoretical, are we talking about tech entrepreneurs? Is she a tech entrepreneur? She has been an entrepreneur in media as it has evolved from the three or four channels to the modern. I mean, if Evan Spiegel's in here, then she should be in here. Absolutely. Inventing mediums and content to fill those mediums.

Well, but not only transitioning from a different kind of media to, a modern kind of media, but also the person as a brand, the influencer would not exist without Oprah, right? There would be no goop without Oprah. That was the theme of our episode. Like, she was the original influencer. And so the concept, because listen, celebrities had been endorsing products and things like that before, but it wasn't that you were a curator of a lifestyle and a certain, like, it's not just that, you know, a certain person has paid a certain amount of money and, and, you know, whatever. But it was, Oprah's like, no, these are products that I believe in for my lifestyle that make my life better. And my philosophy of life is something that you will buy into as a consumer, as a business entity and things like that.

That's, it doesn't, she creates that mold 1,000%. And the incredible thing about Oprah, you know, like it's one thing to have a lot of views. You know, views don't put food on the table. But the way that Oprah was able to like constantly be reassessing her surroundings and aware of her power and influence in the world and create businesses leveraging that. I mean, she wasn't a for hire entertainer by the end. You know, she wasn't employed by people who wanted her on TV. She owned her production. She was the first-

She started Harbour Media. Really the first person to say, I'm not going to just be talent. Like she was that, you know, like the Jay-Z line, like I'm not a businessman, I'm a businessman. Like she was the first, I'm a businesswoman. She was the first media personality to say that. Like, nobody else had done that before of like, no, I'm not going to work for you. Like, I'm going to own this and I'm going to produce it myself. And then I'll auction it off to the highest bidder.

Where there have been bigger stars over the course of the last, let's say, 100 years. But they always worked for other people. You know, there's that Chris Rock joke of you think that an athlete is rich. No, the person that's rich is the person that signs their check. So that's the point is that this concept of talent can be the business. It really kind of begins with her. 100%. I mean, to literalize what you're saying, I mean, it's really self-ownership, you know, in a way that is like,

like transformational. And to have the, I guess like the vision or the wisdom just to like realize the system that you're in and then to sort of like buy yourself out of it so that you can like direct your own fate and then grow this massive business because you look at whatever else is doing. It's like, I can do that. So giving herself permission, I think, to go on that path is the path of the entrepreneur. By the way, she's worth like two and a half to three billion dollars. So, like, lest anyone think that Oprah is just, like, famous for being famous, like, no. She's also rich. Her personal wealth is, like, the market cap of Stitch Fix.

She could buy a Stitch Fix. I want to pin Oprah by saying that she is the godmother of the creator economy, then, to make it modern. And I'm realizing now that, unfortunately, all. three of the women in our list are all in a row here, which if you looked at how I did the brackets wasn't true. They were on opposite sides, but now we're having to do them all in a row. And they're all losing all in a row, although Oprah came so close. I don't know. So the next matchup is Whitney Wolf Hurd versus Bill Gates, which is, again, another one of those, probably this is an impossible matchup. But I will say, again, there were worse beats than

Bill Gates won 80.1% to Whitney's 19.9%. I wanted her to be in this as the sort of the post-iphone app business model, but then there's so many other aspects as well to Bumble. So who wants to take on Whitney here? I'm just looking up some stats here. Humble is worth more than half of Lyft at this point. Like I was always sort of assessing like how big can Bumble get really? Like it's a $10 billion market cap company.

It's potentially bigger than Dropbox. Well, the other thing we got to talk about here is it's not just Bumble. She was a co-founder of Tinder too. Right. Well, so that was another sort of like what was it in, not Enrico. The other co-founder of Zuckerberg of Facebook. Oh, Eduardo, Savorin. Edwardo, thank you.

Yes, exactly. Exactly. Yes, who also got the boot. So she also had a similar fate getting shanked by your co-founder and your fellow leaders and by the system and saying, screw you guys, are going to go do it my way. And I'm going to build a better product that is more inclusive of, you know, a whole set of people that are interested in what I have offered. A sign of an amazing entrepreneur, which is screw you guys, I'm going to bury you. You know? Yep. Like, yep. I mean, and also like, I don't, I think this is true. I may be speaking out of turn, but

my recollection is that match group essentially owns and is half owned by, you know, if not half owned, maybe more than half owned by the Russian mafia or other interests abroad. And that Bumble is the only one that is not. So not only, you know, to say, screw you to Silicon Valley and the investor class and all the people who are in Tinder, but then to also turn to Putin and say the same thing, I think, you know, suggests having, you know, severe Cajonés. And so I think that that's another reason why, like, the fact that they've stayed independent is actually a very unique choice in the dating marketplace. There's one more thing. This is a thesis I've been working on for the last couple of years,

which is that the next generation of successful companies, it's not just going to be about getting to a market first, planning your flag, getting to scale. It's going to be about taste. And so this idea that so many, I mean, literally match.com was founded in 1994, I think. So the idea that Bumble was successful because it had taste, it understood the consumer and the market in a different way that was more conducive. to how the market actually function. Yes, more tasteful. Exactly.

The idea that women, the way that this should work is you don't just, it's, match. com was- Well, they were ahead of the curve in terms of the sort of spam and abuses in the right term, but in terms of the negative behaviors that were happening on social media and on Tinder, and the sort of smarmyness and the lack of protection for minorities and women, you know, I feel like Bumble got ahead of that. Like, they were aware of it. They built in social interactions where, you know, the female members were the ones who

initiated. And so prioritizing the female experience led to their outsized success relative to the conventional functioning of dating apps at the time. I'm just laughing over here because I want to move us on like four, four dudes try to tastefully talk about why bubble was better. Having been someone who used it, like the interaction of, you can't message a woman until she messages you first is like just freaking genius. I mean, that their first $5 billion in market capital were made on that.

But it's also the genius that is not genius if you're the, you know, the underrepresented founder that understands the side of the market that a male cis founder doesn't understand, right? It's genius to believe in it and to pursue it and then to build product around it and then to convince people to come along with you. That's the genius. Yeah. I do want to move it on because we're approaching an hour for our first round here and we've got two more left. I do believe that this is the worst defeat of the whole round tournament.

And I only put these together for the cute reason of it's Larry Ellison versus Lowe's. Larry Page and Sergey Brin, so the Battle of the Larry's. The Google guys won 93.3% to Larry Ellison, 6.7%. And I don't know if any of us will have that much to say about Larry Ellison because I feel like most people don't like Larry Ellison either. This feels like too much of a beat down to me, though. Okay. I'll make a case for Larry for Allison here.

Okay, make the case because I can do one too. but David, hit it. So, well, okay, the case for why Larry Ellison at least should have, you know, perform better amongst Twitter users versus Larry and Sergey would be Larry and Sergey had one good idea once. And, you know, it was a really, really good idea. But they had one, a good idea once and what have they done since? Larry, you know, back to our, you know, Mark versus Jack discussion, like, this dude

built a freaking empire. like brick by brick over decades. And, you know, say what you will about Larry. He is a character non-par excellence. But that guy is an entrepreneur through and through. Is that this is a different kind of entrepreneur where you do cobble together your empire. It's not just you have the one idea. You have the one great company.

Oracle has, first of all, Oracle, I want to. him in here. I wanted Oracle to be represented because, you know, it represents the, I think the modern, it's definitely a hardware company, but like the modern enterprise company, right? Where, you know, this is the modern IBM where since the internet era began, people have turned to Oracle to make it happen. But Oracle didn't have all of the tools at the beginning. So it's been a series of acquisitions. It's been create cobbling together this empire, just like the person that we're going to get to next in the next matchup. But so I think that, again, like the modern definition of a company that grows by acquisition, that becomes a conglomerate that serves all of the needs of its

customer base is not just one trick. No Oracle, no Amazon. Like, Amazon ran on Oracle until recently. As, as you can hear on the fine internet history podcast, when Brian interviewed the the first engineer, the first hire at Amazon. It's a crazy interview hearing about how the fastest way to market and the most performant database was an Oracle one. You know, I'm going to admit my, I feel like this is like an aesthetic bias, but I feel like Larry Ellison is just of an era of entrepreneurs, I suppose, for Silicon Valley people that just, he's kind of like John McAfee in my mind.

The two I can't quite distinguish. and I just, I think about Oracle and I kind of cringe a little bit. And so I have that bias that they have that, they have that, that great headquarters that you can't miss when you come from the airport to San Francisco. That's part of my point. The database headquarters. I always assumed that the cylinders of the Oracle headquarters are made to look like databases, right?

Oh, they're not the real databases? Or the other way around. I mean, maybe that's why we have that is, because like that's kind of a silly abstract concept for a data store, right? Like hard drives? Is it stacked disks? Yeah. Right.

Exactly. Back when they used to use, like, yeah, instead of before solid state drives. Sorry, Larry. Twitter doesn't like you, but you built a $250 billion business. One of the reasons is probably to tie this back into the whole your, your, Andreessen Horowitz thing, the whole Netscape thing is one of the reasons that Jim Clark wanted to become a billionaire is because he was jealous of of Larry Ellison's yachts and things like that. So Larry Ellison has been making a, being a billionaire,

his business for quite a while. Yeah, he set the culture for all. Exactly. That, I feel like Zuck and Bill Gates are not in the model. You're right because, Chris, you said that he's of a different generation. And I think you're right in a way. Like, he is sort of, he's closer. I feel like he's more like a bond villain, you know, and that doesn't resonate for our generation. He's like 80s Wall Street meets tech. Yes. Like, Coke and blow. Like, that's their whole jam and, you know, yachts and buying a stentious thing.

I will say, Jenny and I were in Lanai this summer. Oh, it's a little baby moon in Lanai on Larry Ellison's, you know, island that he owns. And it was very nice. It was very nice. It was great taste of islands. Larry give you a call and say, hey, we got a spot for you. You should come in. I saw him.

Really? No. There are two hotels on the island. And you can book you even normal people like us. But yeah, we saw him at one of the hotels. Like, yeah, it was amazing. And dude drives a Corvette, you know, which is like a really, you know, nice. But I would have, I would not have expected that.

Wait, no, I would have perfect. Fucking cliche. There you go. See, it's the whole 80s supervillain thing. I don't know. I'm not letting this one go. Dude, watch Miami, Miami, Diablo, but. Yeah.

Okay. All right. So to round off our round of 16 and to round off this first episode, another beat down that I feel like is kind of similar, but also... Speaking of Hawaii. It's one of those things where, like, you can't... What are you going to do? Mark Benioff win against Steve Jobs. And Steve Jobs won 90.3%

to 9.7%. But I can make for sure a case for Mark Benioff, for the SaaS era, for like, come on, guys. But I feel like even Mark Benioff was voting for Steve Jobs. That's true. That's true. That's true. But, all right. Here's an interesting, so I don't know the, just to like throw out an interesting point of view.

Like, every generation of tech is so much bigger than the previous generation. because technology and the internet reaches so many more people than it ever did before, and it's compounding, and you have population growth and all this stuff. I wonder if Steve Jobs, in all the value creation he did at Apple until his unfortunate early death, is actually less than the total amount of value that Mark Mannyov has traded at Salesforce. Just because of how much of Apple's market cap today has... come from the Tim Cook era. And this is a silly straw man, because at the end of the day,

Apple is Apple because of Steve Jobs, so it all is really attributable to him. But it is this interesting thing to observe that, like, most of the growth, like most of the value in the entire tech ecosystem has been added in the last 10 years. And there are companies that are sort of doing the playbook that Mark Benioff sort of, I don't,

can we say that he, he discovered it or what was maybe just the most, the first person. He marketed SaaS, right? He kind of like, I don't want to say put it on the map, but in the sense that he established the original logo was software with a red, you know, X through it. Right, right. So he was like, you know, that and I think Ben, like you make a really interesting point. Like the nexus of those two phenomenon, mobile computing devices and cloud software,

had to sort of happen together. So there had to be a legitimization of both. Because what the iPhone did was it took a communications device, an internet communicator, and a music player, all together. These are all one device. Are you getting it? Are you getting it?

I'll do that in our sleep. We'll talk about Steve Jobs at some point, but just the greatest presentation any human has ever made, that 2007 keynote. that and then, you know, we could go back to, of course, the mother-of-all demos, but that was sort of, you know, setting the stage for all the rest of it. But nonetheless, I do think that those two things together, the cloud era and the mobile computing era and both eating the enterprise world of the folks we just talked about is what led

to so much, you know, growth and development. We'll probably save our conversation or comments about Steve Jobs until later. But, you know, I think that Mark Benioff is a strange, like he is, a, I don't know, I'm thinking about like the Batman universe. Like he's sort of, you know, a, he's not like two-faced in the sense that he's like, like, well, he's not evil, but, you know, he has like that strain of kind of persistence, but then comes from like, you know, maybe a good or warm heart kind of thing. And so he's kind of in this ambivalence, like, I have an ambivalence sentiment, I think generally towards him. I've been in Salesforce Tower and I'm like, this is a big,

large phallic thing in the middle of San Francisco. But yes, the guy that built it is supposed to be like a nice guy and gives the charity. So I don't really, I'm not quite sure what the vibe is here. You know what I mean? So that's why I'm just kind of left with between those two, you know, the texture and the grit and the dirt of like Steve Jobs like feels like, you can just dive in there. Like, you know, I'd rather probably, you know, have a cocktail with like, I don't know, Steve Jobs does cocktails, maybe a joint, you know, with Steve Jobs rather than Benny. LSD. Yeah. I think I think Mark would be pretty fun to party with. True.

Both. He's the enterprise sales guy, is enterprise sales guy. As long as he's not selling me the whole time on SaaS, it could be fun. Well, listen, I'm going to bring this episode to a close because we're almost exactly an hour. When will we talk about Steve Jobs? What will we say about Steve Jobs? You're going to have to tune in to episode two to find out. Thank you to all of the people on the panel here.

David, Ben, Chris, tune in next week. for episode two to find out who makes it through the, are we allowed to say elite eight? No, probably not. Lower casey. The quarterfinals, the semifinals, and the finals, and the finals, and find out who won the hashtag World Cup of Entrepreneurs. Talk to you next time.