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Brian McCullough
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 Messina
Chris, howdy, howdy. Glad to be here. I'm very excited to be part of this World cup of entrepreneurs.
Brian McCullough
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 ne 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. Ben, you go first.
Ben Gilbert
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.
David Rosenthal
First in our hearts. First in our hearts.
Ben Gilbert
David, over to you.
David Rosenthal
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 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.
Brian McCullough
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.
David Rosenthal
Oh, go for it.
Brian McCullough
Here's the problem you guys figured out.
David Rosenthal
We're getting the arguing out of the way now so that we can all agree on the picks later.
Chris Messina
Clear the air right now.
Brian McCullough
Came up with the concept or the term that Al Gore was Marc Andreessen's vc. And that's like the most perfect way to put it. So I'm pissed at you guys cause 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.
Ben Gilbert
Second edition.
David Rosenthal
Second edition. Yeah.
Unnamed Speaker
Okay.
David Rosenthal
Thank you, Brad.
Brian McCullough
Yes, yes, 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. Sixteen entered, only one came out of the Thunderdome. And essentially what. 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 then that will allow us to eventually get through everyone until we get to the one that was left standing.
Ben Gilbert
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.
Brian McCullough
Right.
Chris Messina
Well.
Brian McCullough
And the only winner that. Well, right. That will 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.
David Rosenthal
He's got to. Got to listen to the end. I like this.
Chris Messina
Exactly.
Brian McCullough
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 84.5% to Evan's 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 stories? Or even before that, ephemeral messaging and things like that?
Chris Messina
It's a new medium, right? That's right. It takes advantage of an emerging technology as that technology is still being deciphered or used.
David Rosenthal
He's like the chief Product officer for the Internet, Right?
Chris Messina
Well, for Facebook, certainly.
David Rosenthal
Yeah.
Chris Messina
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.
Brian McCullough
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, early on, ephemeral messaging, as what Evan probably gets.
Chris Messina
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 performance. 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 also, remember, the assumption was that people were more consumers. The 90101 rule of social media is that 90% of people are just there to consume, and 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.
David Rosenthal
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 the 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 taking that.
Chris Messina
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 was curated. And so this, like, the ephemerality was a kind of response to the abundance of communicating through visual images. So it really didn't make sense to hold onto everything anymore. Whereas before it was sacred to have these digital artifacts. What I think Evan realized was we don't save all of our phone calls, so why would you save all of Your photos that are being shared.
Brian McCullough
Ben, let me ask you this on a straight entrepreneur sort of level. Evan's also famous for not selling to Mark Zuckerberg. And let's think of that from the pure entrepreneur standpoint of turning down billions of dollars, being able to say no and being like, I'm going to build a social media company that will, will thrive. It has been thriving and has as an entrepreneur. We remember when, when, when Snap stock recently was under, 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.
Ben Gilbert
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 the famous, of course, crying in the bathroom after turning down the billion dollar offer by Yahoo.
Brian McCullough
Vomiting in the bathroom.
Ben Gilbert
I'm sure there may have been many other things.
Chris Messina
There are lots of bodily.
Ben Gilbert
No, but Brian, you a great point. And even very recently, like I just looked it up, Snap is $116 billion market cap company. People had counted them down and out obviously a lot of 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 it's, it's, 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 US in a big way. And Instagram launching this basically cut off the need for people to ever download Snap internationally because they could get the same functionality out of Instagram where they already had that multibillion 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, they're still $100 billion plus company now and have over comment.
Brian McCullough
Let me play the pundit here a little bit like a sports pundit and say that I think that the result is a bit unfair to Evan. If I were the one voting, I would say that he probably should have advanced further in the tournament for all the reasons just said.
Unnamed Speaker
But then also for that last bit.
Brian McCullough
Too about how it's not just that he has a company that. That reaches scale, then goes public, but then also has troubles and then can theoretically fix those troubles and continue to thrive and things like that. I'm going to move on to play.
David Rosenthal
One quick thing before I move on, Dave. Am I allowed?
Brian McCullough
Yes, please.
David Rosenthal
Just met a point that I think we talk about this. We've been talking about this a lot on acquired 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 in social because none of this ever would have happened.
Brian McCullough
Well, and because everybody Facebook would had Evan not had Diamond Hands own Instagram and Snap, you know, so, like, it's almost like.
David Rosenthal
And that was before stories, right? So, like, yeah, no stories if that happened.
Brian McCullough
So it's almost like Gandalf 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.
Unnamed Speaker
You Balrog, you.
Brian McCullough
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. The Silicon Valley startup playbook. Thoughts on that as a theme for matching up?
Ben Gilbert
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, sample size and the sample source. I mean, we could look. I think Jeff Bezos should win this. Like, look at market cap alone, I think.
David Rosenthal
Well, this is like getting seated against, you know, like Duke in the. In the tournament. Like, you know, Jack.
Ben Gilbert
It's an unfortunate pull, the rough draw here, but I think it's worth acknowledging what a different company Alibaba is than Amazon. The biggest one is their B2B business. Alibaba moves a tremendous amount of merchandise through a B2B E commerce experience of which doesn't really exist in the US yet. 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.
David Rosenthal
The US yeah, Alibaba has a salesforce for their core marketplace. Amazon doesn't have a salesforce for their marketplace.
Brian McCullough
Look, in theory, Jeff Bezos also was early in a market, but Jeff Bezos is early in a market in the west, in the US or whatever. Consider the also complicating factor of Jack Ma bringing entrepreneurialism and Silicon Valley style entrepreneurialism to China in the late 90s and early 2000s. That is breaking ground. That is apocal. Essentially.
Chris Messina
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 in particular, and this isn't meant to sort of be singing Bezos praise, but the way in which Bezos sort of required product direction to be done through written testimony, effectively to write whatever the three page document, have people read it in silence and then to socialize that. 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.
Brian McCullough
Have you guys done Alibaba? Unacquired? Pardon my ignorance on that.
David Rosenthal
Yes, it was a few years ago though.
Ben Gilbert
I think we may get 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 I was gonna say that. Yeah, yeah. The notion that like Chinese companies move much faster than their American counterparts.
Chris Messina
I was gonna say you should unpack that a little bit, like for the listeners, because I know that it's something at TikTok that is. So maybe that is an example of that cultural phenomenon that was. That was socialized.
Ben Gilbert
So what is that working 99 hours.
David Rosenthal
Per week, 9am to 9pm oh, you're right.
Ben Gilbert
Yeah. Nine to nine, six days a week, which I don't. Maybe that is around 99.
Chris Messina
Might be about 99 hours, I don't know.
Ben Gilbert
Yeah, more than 40. 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 zones. So capitalism in a very small and different way is very new to the country. 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, 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.
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Brian McCullough
I'm going to move on real quick because Jack is having issues. I just want to say that Jack.
Ben Gilbert
You mean vanishing issues?
Chris Messina
Yeah, that's the problem.
Brian McCullough
Jack was the first sort of face of like Silicon Valley style tech startup entrepreneurship in China. And he also might be the first one out to pasture. But 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 two this on Twitter.
David Rosenthal
So.
Unnamed Speaker
Okay, understood.
Ben Gilbert
You say Jack logged in and tipped the scale.
Brian McCullough
Well, but look, to bring, you know, David mentioned seeds. Like if. 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.
Chris Messina
And if you hosted this on Facebook for the poll, I wonder if anybody would have actually participated.
Brian McCullough
Okay, well, all right, maybe I'll tell you what, let's address the upset first and then we can give Zuck his due as an entrepreneur at the end. Could it just come down to people don't like Zuck?
David Rosenthal
Yes, likely, yes.
Ben Gilbert
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.
Brian McCullough
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. 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 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.
Chris Messina
That's not even true. That's not true.
Brian McCullough
Okay, Chris, take it.
Chris Messina
He didn't have any ideas. They were all other people's ideas.
David Rosenthal
Oh, he had Wire Hog. That was.
Chris Messina
I'm pretty sure that was built on Napster or like, I mean, honestly, like, 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 heirs 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 them. Like, he is truly Bill Gates, the second coming. He is like Caesar's heir, given that he wants to build an empire.
Ben Gilbert
This is the World cup of entrepreneurs. This is the World cup of, like, nice guys. I mean, what's the goal here?
David Rosenthal
I'm just.
Chris Messina
Look, people voted on this. I'm not saying the people who are right or wrong. I mean, Zuckerberg is the guy that would shank you if he got the chance and then claim that it was the Snapchat guy.
Brian McCullough
Yeah, but I'm with Ben there. That's what an entrepreneur should do. He should be willing to shank.
David Rosenthal
The consequence of that is people aren't going to like you, and so you're going to lose Twitter popularity contests.
Chris Messina
So there you go.
David Rosenthal
I think Zuck's having the last laugh here.
Chris Messina
Yeah, I think so.
Brian McCullough
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 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'd just take it and start another social network. And he already likes the one he has.
Unnamed Speaker
Okay.
Brian McCullough
This is probably not going to help his case, but there are certain entrepreneurs that can see clearly one vision and can execute on it perfectly, whether it be you're Rockefeller and you see that oil is going to power the 20th century.
David Rosenthal
Next acquired episode, foreshadowing.
Brian McCullough
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.
Ben Gilbert
Yes.
David Rosenthal
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. And that is the story of Zuck. The whole time dropping out of Harvard. That was. Wow, that's crazy. Who does that? Not selling to Yahoo. That's crazy. Going public at $100 billion valuation. Crazy. And everything happening now.
Brian McCullough
David, 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 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 the fact that he was the first. I would say that Mark Zuckerberg is the model for the modern concept of an entrepreneur.
David Rosenthal
Yeah. I mean, the Social Network inspired so many people. It was the Liars Poker of like our generation, dude.
Ben Gilbert
For like five years, when I would write code, I would do it to the Social Network soundtrack after that movie came out.
Chris Messina
Yes.
Brian McCullough
Chris, you were shaking your head when David said that.
Chris Messina
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's an empire builder. Like he and I.
Ben Gilbert
What is an entrepreneur then?
Chris Messina
No, an entrepreneur. It's French. And basically it's someone who makes bread from strange ingredients they have lying around. To me, Zuckerberg saw the map as black and wanted to paint it blue by moving his troops around to evaluate him from convention. What Brian's saying, most of the time, founders will leave after their 10, 15 year stint because they're bored or they're tired. They want to do something else. That has never been the case with Zuckerberg. 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 kind of public company set of principles that I would other entrepreneurs.
Brian McCullough
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.
David Rosenthal
He is.
Brian McCullough
He is doing it. He's doing it in the modern way.
Chris Messina
And so you don't need an army anymore. You just need people to log into your website.
David Rosenthal
You know, there's that he was a stiff nut growing up.
Chris Messina
Stiff nut.
David Rosenthal
He was a nut about civilization, right?
Chris Messina
Yeah, yeah, he was.
Brian McCullough
He said it. He said it in interviews. Yes. That's awesome. So my theory to psychoanalyze him is.
Chris Messina
And also he studied the classics. The only, like, courses that he actually, like, finished in college were about, like, the Roman emperors literature and Latin and like, all that stuff.
Brian McCullough
So my theory is maybe I'm typecasting.
Chris Messina
Too much, but I just. I can't let.
Brian McCullough
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, 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 crypt? Cryptocurrency he creates? Because that's the juice for him. That's the juice.
Chris Messina
Hangs out with, like, Jason Boats and stuff. You know, like, Zuck's like. He does, like, little photo ops in Hawaii to, like, you make it look like he's like, you know, an American or something. Like, you know, he's like, I just.
Brian McCullough
Have to do this versus grilling meats or something.
David Rosenthal
So your guys, to sum it up is, is that Zuck is Caesar, but not Romulus.
Chris Messina
And we.
Brian McCullough
There you go. Right, Ben, what were you going to Say.
Ben Gilbert
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 of the companies that all these people founded, and then we have an answer, and we don't have to have a conversation here, which is a, which is one definition of success, but B, it doesn't take the creativity into account. Chris, what you're sort of arguing is like part of entrepreneurship is having an initial idea and then seeing that idea through and making something people want, in YC's parlance, and then figuring out how to both capture value from 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.
Chris Messina
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 newsfeed was the first example of this where the whole team, like, after there was like, literally protests in the streets in Palo Alto against the news feed, and it started the whole conflagration with privacy.
Ben Gilbert
Oh, no.
Chris Messina
He doubled down. You know, he had his troops of, you know, his 300 troops with, like, Boz and like the rest of them, they had their shields up and their spears, and they came out and they decimated whoever it was they were fighting.
Brian McCullough
Well, that comes back to David's argument that. Or 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.
Chris Messina
Yeah, well, that's. That's how I see. 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 from. 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, 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 the dogs just sniff each other's butts. Humans do the same thing in different ways for 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.
David Rosenthal
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?
Chris Messina
I'm in it. Yeah, that's right.
David Rosenthal
You are in it. Oh, wow. Okay. Okay.
Chris Messina
It's like a cameo for, like, two seconds.
David Rosenthal
Perfect discussion. I 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 riled up and, like, they get. I'm like, I lived in.
Chris Messina
Like, someone gets pushed down.
David Rosenthal
That is not going down in Palo Alto. I do not believe it for a second.
Chris Messina
I mean, honestly, it undermined 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 it's one of those things where it's important to raise the alarm to some degree, but the lack of personal accountability that the movie sort of takes away. And then at the end, it's like, turn off notifications. It's like, okay, not realistic or you're.
David Rosenthal
Gonna go to prison in Palo Alto. What?
Brian McCullough
All right, let's move on. Yes. Being the producer and moving on here.
Unnamed Speaker
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Brian McCullough
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 Lake's 21.9%. Ben, I think you might have been when we were soliciting for like 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 as a representative of a bunch of things. But make your argument for Katrina as a great entrepreneur.
Ben Gilbert
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. She's financially savvy in a way that I feel a lot of founders glaze over it. 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, 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 always been an extremely financially savvy operator in addition to to having that je ne sais quoi that a founder has of to use it again, making something people want. So first of all, I just have.
Brian McCullough
Stitch Fix. If we didn't, I just wanted to.
Ben Gilbert
Make sure that we said oh, good point.
Brian McCullough
Stitch Fix. Yes, sorry, go on.
Ben Gilbert
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 the Trunk Club was one that sold to Nordstrom and this one, it just had so much more life and running room because of the way it integrated technology and 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 algorithm to sort of be the data science arm of Stitch Fix. And I've just been continually surprised year over year that this business continues to grow, continues to grow quickly and hasn't been a flash in the pan.
Brian McCullough
Anyone else? David?
David Rosenthal
Yeah, I mean to Ben's point, 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 certainly didn't in her era. She was so incredibly capital efficient. I remember I interned at Maritech, which is a great growth firm in Palo Alto when my summer in business school and we were like, oh Stitch Fix, what a great company. We got to get they raising around. And like nope, not raising around. Don't need the money. They're cash flow positive, not going to sell equity. And that was so contrarian at the time. And she didn't need it. She protected her cap table and it's done amazingly well.
Brian McCullough
My argument for including her and I know this is not an easy fit is because it's not a D2C 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 I want, it's a retailer, it's right. But the modern retailer where it is, you have that very close connection with your consumer. You have the subscription aspect to it, you have. So I thought that she was a perfect inclusion because she sort of melds all of those parts of what modern commerce is and modern brands are.
Chris Messina
I mean, it also feels like she was so good at understanding the consumer, understanding the problem space, understanding technology, and in this case, like a good entrepreneur being able to go all the way from soup to nuts, as they say, sort of from the highest level of the business and how to operate it down to the individual experience of getting the box and opening it and dressing yourself and then the whole process of data enrichment. This was, you know, when Stitch Fitch 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, how 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 she definitely is one of those underappreciated female founders that deserves a whole lot more credit and credibility.
Ben Gilbert
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 in terms of the scale and impact of it. Particularly both the combination of SpaceX and Tesla.
Brian McCullough
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.
David Rosenthal
This is so close.
Brian McCullough
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. I don't.
Chris Messina
So close.
Brian McCullough
This is another one.
David Rosenthal
Into triple overtime.
Brian McCullough
Well, but also, as a pundit, I feel like, you know, I feel like Oprah really should have won this one.
Chris Messina
She's robbed.
Brian McCullough
Not necessarily robbed, but I'm gonna.
Ben Gilbert
She's doing pretty well for someone who's been robbed.
Chris Messina
Fair. Fair.
Unnamed Speaker
Well, right, so.
David Rosenthal
Lives in the promised land.
Brian McCullough
We're gonna talk about. We're gonna talk about Oprah right here. I'm gonna toss to David. I know why Oprah should have gone farther in this tournament, but if you've got team me up on Oprah.
David Rosenthal
Well, this was one of the most fun acquired episodes that we did. When did we do this, Ben? Last summer.
Ben Gilbert
A year ago?
David Rosenthal
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. That. That's one card in her favor, but that was, like, the only card in her favor. I mean, broken families, sexual abuse, got. 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.
Ben Gilbert
And the two 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, yeah, but, like, I think any of these, like, streamer numbers, like, nothing compares.
Brian McCullough
No, no way.
Ben Gilbert
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.
Chris Messina
Might your point. The way in which people would watch television, you know, in that era, I feel like, 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.
Brian McCullough
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? She has been an entrepreneur in media as it has evolved from the three or four channels. Two.
Chris Messina
I mean, if Evan Spiegel's in here, then she should be in here.
Brian McCullough
Absolutely.
Chris Messina
Inventing mediums and content to fill those mediums well.
Brian McCullough
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.
David Rosenthal
That was the theme of our episode. Like, she was the original influence.
Brian McCullough
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, 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%.
Ben Gilbert
And the incredible thing about Oprah, you know, like, it's one thing to have a lot of views, you know, views don't. 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, 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 started harbor, really the first.
David Rosenthal
Person to say, I'm not gonna 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 gonna work for you. Like, I'm gonna own this and I'm gonna produce it myself, and then I'll.
Ben Gilbert
Auction it off to the highest bidder.
Brian McCullough
There have been bigger stars over the course of the last, let's say 100 years, but they always worked for other people. 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 a hundred percent.
Chris Messina
Well, I mean, to literalize what you're saying, I mean, it's really self ownership in a way that is transformational. And to have, I guess the vision or the wisdom just to realize the system that you're in and then to sort of buy yourself out of it so that you can direct your own fate and then grow this massive business because you look at what everyone else is doing, it's like, like I can do that. So giving herself permission, I think, to go in that path is the path of the entrepreneur.
Ben Gilbert
By the way, she's worth like two and a half to $3 billion. So lest anyone think that Oprah is just famous for being famous. No, she's also rich. Her personal wealth is like the market cap of stitch fix.
Chris Messina
She could buy a stitch fix.
Brian McCullough
I want to pin Oprah by saying that she is the godmother of the creator economy then to make it modern. 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 Wolfe Heard 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 Apple business model. But then there's so many other aspects as well to Bumble. So who wants to take on Whitney here?
Ben Gilbert
I'm just looking up some stats here. Bumble is worth more than half of Lyft at this point. I was always sort of assessing like how big can Bumble get? Really? Like it's a $10 billion market cap company. One of the potentially bigger than Dropbox.
David Rosenthal
Well, the end. The other thing we got to talk about here is it's not just Bumble. She was the co founder of Tinder too, Right?
Chris Messina
Well, so that was another sort of like, was it not Enrico, the other co founder of Zuckerberg?
David Rosenthal
Oh, Eduardo Saverin.
Chris Messina
Eduardo, thank you. Yes, 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. I'm 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.
Brian McCullough
Are interested in what I'm doing of an amazing entrepreneur, which is, screw you guys. I'm going to bury you, you know?
David Rosenthal
Yep. Like, yep.
Chris Messina
I mean, I. 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, 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 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 suggests having severe cojones. And so I think that that's another reason why the fact that they've stayed independent is actually a very unique choice in the dating marketplace.
Brian McCullough
There's one more thing. This is a thesis I've been working on for the last couple years, which is that the next generation of successful companies, it's not just going to be about getting to a market first, planting your flag, getting to scale. It's going to be about taste. This idea that so many. I mean, literally, Match.com was founded in 1994. I think, like, so the idea that Bumble was successful because it. It had taste, it understood the consumer and the market in a different way, that was more conducive to how the market actually functioned. Yes. More tasteful. Exactly. The idea that women. The way that this should work is you don't just. It's. Match.com was.
Chris Messina
Well, they were ahead of the curve in terms of. Of the sort of. Spam abuse isn't the right term, but, like, in terms of the negative behaviors that were happening on social media and on Tinder and the sort of smarminess 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.
Ben Gilbert
I'm just laughing over here because I want to move us on. Like, 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 fricking genius. I mean, the first $5 billion in market cap were made on that.
Brian McCullough
But it's also the genius that is not genius if the underrepresented founder that understands the side of the market that a male CIS founder doesn't understand. Right.
Chris Messina
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.
Brian McCullough
That's the genius. 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 tournament. And I only put these together for the cute reason of It's Larry Ellison versus 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, I feel like most people don't like Larry Ellison either.
David Rosenthal
But that's like too much of a beat down to me though, like, okay, I'll talk about Larry for Alison here.
Brian McCullough
Okay, make the case because I can do one too, but David, hit it.
David Rosenthal
So, okay, the case for why Larry Ellison at least should have performed 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 good idea once and what have they done since? Larry, sort of 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.
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Brian McCullough
Life's been a.
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Brian McCullough
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 wanted him in here. I wanted Oracle to be represented because 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 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 no Oracle, no Amazon.
David Rosenthal
Amazon ran on Oracle until recently.
Ben Gilbert
As you can hear on the Fine Internet History podcast when Brian interviewed the first engineer, the first hire at Amazon. It's a crazy interview hearing about how this the fastest way to market and the most performant database was an Oracle one.
Chris Messina
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, or Silicon Valley people that just. He's kind of like John McAfee in my mind. Like, 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.
Brian McCullough
They have that great headquarters that you can't miss when you come from the airport to San Francisco.
Chris Messina
That's part of my plan.
David Rosenthal
The database headquarters. I always assumed that the cylinders of the Oracle headquarters tended to look like.
Chris Messina
Those are databases.
David Rosenthal
Right.
Chris Messina
They're not the real databases or the other way around.
Ben Gilbert
I mean, maybe that's why we have. Because that's kind of a silly abstraction concept for a data store. Right. Hard drives, stacked disks.
Chris Messina
Yeah, right, exactly. Back when they used to use, like. Yeah. Instead of before solid state drives.
Ben Gilbert
Sorry, Larry. Twitter doesn't like you, but you built a $250 billion business.
Brian McCullough
One of the reasons is probably to tie this back into the whole 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 Larry Ellison's yachts and things like that. So Larry Ellison has been making being a billionaire his business for quite a while.
David Rosenthal
Yeah, he set the culture for. Exactly.
Chris Messina
Zuck and Bill Gates are not in the model.
Brian McCullough
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.
Chris Messina
I feel like he's more like a Bond villain, you know, and that doesn't resonate for our generation.
Ben Gilbert
He's like, 80s Wall street meets tech.
Chris Messina
Yes. Like coke and blow. Like, that's their whole jam and, you know, yachts and buying.
David Rosenthal
I will say Danny and I were in Lanai this summer. We did a little baby moon in. In Lanai on. On Larry Ellison's, you know, island that he owns. And it was very nice. It was very nice.
Brian McCullough
I. Yeah.
Ben Gilbert
Larry give you a call and say, hey, we got a spot for you. You should come in. Really.
David Rosenthal
There are two hotels on the island, and you can bookie 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.
Brian McCullough
Wait. No, I would have. Perfect fucking cliche.
David Rosenthal
There you go.
Chris Messina
See, it's the whole 80s super villain thing. I Don't know. I'm not letting this one go, dude.
David Rosenthal
Lamborghini Diablo. But yeah.
Brian McCullough
Okay. All right, so for. 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.
Ben Gilbert
Of Hawaii, it's one of those things.
Brian McCullough
Where, like, you can't. What are you going to do? Marc Benioff went against Steve Jobs.
Unnamed Speaker
And.
Brian McCullough
Steve jobs won 90.3% to 9.7%. But I can make for sure a case for Marc Benioff for the SAS era for, like, come on, guys.
David Rosenthal
But I feel like even Marc Benioff was voting for Steve Jobs.
Ben Gilbert
That's true.
Chris Messina
That's true.
Ben Gilbert
All right, here's an interesting. So I don't know the. Just to like, 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 Martin Benioff has created 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 most of the growth, like most of the value in the entire tech ecosystem has been added in the last 10 years.
Brian McCullough
And there are companies that are sort of doing the Playbook that Marc Benioff, can we say that he discovered it or was maybe just the first person.
Chris Messina
And he marketed SaaS. Right. He kind of like, I don't want to say put it on the map, but in the sense that the original.
David Rosenthal
Logo was software with a red X through it.
Ben Gilbert
Right, Right.
Chris Messina
So he was like, I think, Ben, you make a really interesting point. The nexus of those two phenomenon, mobile computing devices and cloud software, had to 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.
David Rosenthal
These are all one device.
Chris Messina
Are you getting it?
David Rosenthal
Are you getting it?
Brian McCullough
I'll do that in our sleep.
Ben Gilbert
We'll talk about Steve Jobs at some point. But just the greatest presentation any human has ever made, that 2007 keynote that.
Chris Messina
And then we could go back to of course the mother of all demos, but that was sort of setting the stage for all the rest of it. But nonetheless, I do think that 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 growth and development. We'll probably save our conversation or comments about Steve Jobs until later, but I think that Marc Benioff is a strange. He is a. I don't know, I'm thinking about the Batman universe. He's sort of, I don't. He's not like two faced in the sense that he's like he's not evil but he has that strain of persistence but then comes from maybe a good or warm heart kind of thing. And so he's kind of in this ambivalence. I have an ambivalent 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 the guy that built it is supposed to be a nice guy and gives to 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, the texture and the grit and the dirt of Steve Jobs feels you can just dive in there. I'd rather probably have a cocktail with, I don't know, Steve Jobs does cocktails. Maybe a joint with Steve Jobs rather than Benny lsd. Yeah, definitely.
Ben Gilbert
I think Mark would be pretty fun to party with.
Chris Messina
True both.
Ben Gilbert
He's the enterprise sales guy. Is enterprise sales guy.
Chris Messina
As long as he's not selling me the whole time on SaaS. It could be fun.
Brian McCullough
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 8? No, probably not. The route lowercase the quarterfinals, the semifinals and the finals. And find out who won the hashtag World cup of Entrepreneurs. Talk to you next time.
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Techmeme Ride Home: (Bonus) World Cup Of Entrepreneurs Part 1 – May 15, 2025
In this exceptionally special episode of Techmeme Ride Home, host Brian McCullough teams up with co-host Chris Messina and special guests Ben Gilbert and David Rosenthal from the renowned Acquired podcast to embark on an unprecedented "World Cup of Entrepreneurs." This unique bracket-style tournament aims to crown the foremost entrepreneur of the last three decades by pitting sixteen influential figures against each other in head-to-head matchups, determined by listener votes on Twitter.
Brian introduces the concept, explaining that each matchup will feature a contender whose loss will be dissected to highlight their entrepreneurial prowess before advancing to the next round. The process continues until the ultimate champion emerges.
Discussion Highlights:
The panel dives into Evan Spiegel's innovative contributions to social media, particularly his development of ephemeral messaging and the "Stories" feature, which revolutionized visual communication. Chris Messina emphasizes Spiegel’s role in transforming the camera into a core communication tool, stating, “[...] it really was, you know, I think Evan realized we don't save all of our phone calls, so why would you save all of your photos that are being shared” ([07:00]).
Brian McCullough praises Spiegel's entrepreneurial spirit for turning down substantial acquisition offers, notably refusing to sell Snapchat to Mark Zuckerberg, highlighting his "diamond hands" mentality. Ben Gilbert draws parallels to Mark Zuckerberg's earlier decision to turn down offers from Yahoo, underscoring the rarity of such steadfast visionaries in the tech landscape.
Discussion Highlights:
The debate centers on comparing the entrepreneurial journeys of Jack Ma and Jeff Bezos. Ben Gilbert critiques the simplistic comparison of Alibaba to Amazon, emphasizing Alibaba’s unique B2B focus, which transcends the typical B2C model that Amazon exemplifies. He notes, “Alibaba moves a tremendous amount of merchandise through a B2B E-commerce experience of which doesn't really exist in the US yet” ([14:03]).
David Rosenthal adds that Jack Ma was instrumental in importing Silicon Valley’s entrepreneurial ethos into China, fostering a competitive and innovation-driven environment characterized by extreme work ethics like the "996" culture (9 AM to 9 PM, six days a week). Chris Messina elaborates on how this relentless work culture has become a benchmark for Chinese startups, contributing to Alibaba’s sustained growth despite intense competition.
Discussion Highlights:
This surprising upset pits Facebook's Mark Zuckerberg against Twitter's Jack Dorsey, with Dorsey securing a decisive victory. The panel deliberates Zuckerberg's role as a visionary yet controversial figure, debating his entrepreneurial merits. Chris Messina criticizes Zuckerberg’s approach, describing him as “less inventive” and more of an empire builder, akin to “a modern-day Julius Caesar” ([26:28]).
Ben Gilbert acknowledges Zuckerberg's strategic acumen in scaling Facebook but questions the depth of his inventive contributions compared to peers like Dorsey. David Rosenthal argues that Zuckerberg’s ability to persistently push his vision, even amid public dissent, exemplifies a core entrepreneurial trait, albeit one that has led to significant privacy controversies and public backlash.
Discussion Highlights:
Katrina Lake is celebrated for her innovative approach to the fashion retail industry through Stitch Fix, combining data science with personalized styling to create a sustainable subscription model. Ben Gilbert highlights her financial savvy and capital-efficient strategies, noting Stitch Fix's impressive growth and resilience in a competitive market ([37:45]).
However, Elon Musk's multifaceted impact across various industries, from electric vehicles to space exploration, overshadows Katrina’s achievements in this matchup. The panel agrees that while Katrina's contributions are significant, Musk's broader and more transformative influence on technology and society grants him the upper hand.
Discussion Highlights:
This closely contested matchup features Patrick Collison of Stripe against media mogul Oprah Winfrey. The narrow margin reflects the diverse definitions of entrepreneurial success. Oprah's journey from overcoming personal adversity to building a media empire is lauded for its inspirational and pioneering spirit. Ben Gilbert emphasizes her unprecedented ability to capture and maintain massive audience attention, stating, “44 million people would concurrently tune in to watch Oprah” ([44:12]).
On the other hand, Patrick Collison's establishment of Stripe as a fundamental infrastructure provider in the fintech space is recognized for its scalability and essential role in enabling countless online businesses. The panel debates the varying impacts of media versus technology entrepreneurship, ultimately awarding the win to Collison by a whisper-thin margin, which underscores the subjective nature of such rankings.
Discussion Highlights:
The collection of Larry Ellison against the duo Larry Page and Sergey Brin results in a massive victory for Google’s founders. The panel briefly touches upon Ellison's legacy in building Oracle through strategic acquisitions and enterprise software dominance but concedes that Page and Brin's creation of Google, with its profound impact on information accessibility and digital advertising, far surpasses Oracle's influence in the modern tech ecosystem.
Discussion Highlights:
In a heavyweight showdown, Steve Jobs triumphs over Marc Benioff. The conversation reflects on Benioff's pioneering role in popularizing Software as a Service (SaaS) and building Salesforce into a cloud computing giant. However, Jobs' revolutionary contributions to consumer technology, from the Macintosh to the iPhone, and his ability to create a cohesive, desirable ecosystem at Apple resonate more profoundly with both the panel and the voters.
Ben Gilbert muses on the compounded growth of tech companies in the mobile and cloud eras, attributing much of today's value to the foundational work of visionaries like Jobs. Chris Messina strongly advocates for Jobs' unparalleled ability to innovate and transform entire industries, cementing his place as a quintessential entrepreneur.
As the first round of the World Cup of Entrepreneurs concludes, the panel reflects on the diverse qualities that define great entrepreneurship, from visionary innovation and strategic acumen to resilience and the ability to scale impactful businesses. With matchups still ongoing, listeners are left eagerly anticipating the next episode to discover who will advance and ultimately claim the title of the top entrepreneur.
Brian McCullough wraps up the episode by thanking his co-hosts and guests, hinting at further exciting battles in the brackets, and encouraging listeners to tune in for the continuation of this groundbreaking entrepreneurial showdown.
Note: Throughout the episode, notable quotes from participants provide deeper insights into the panel's perspectives, enriching the discussion and offering listeners a comprehensive understanding of each entrepreneur's significance.