Tech Brew Ride Home - (Bonus) World Cup Of Entrepreneurs Part 2

Episode Date: May 18, 2025

Who wins? Jobs? Gates? Musk? Bezos? Collison, even? The grand finale of our #WorldCupOfEntreprenurs. (Originally aired October of 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 back to another super special episode of the TechMeme Ride Home Experience. We're going to do part two of our World Cup of Entrepreneurs, I don't know, a contest, extravaganza, hashtag World Cup of Entrepreneurs.

These were all voted on by you, the listeners of the TechMeme Ride Home podcast. So that everyone knows people's voices. Let me reintroduce my usual guest or not. a co-host, Chris Messina, inventor of the hashtag. The West Coast business development at Republic, right? Is that your... Head of business development at the Republic. Head-muck-dy-muck.

Yep. Republic. And we're joined by the co-hosts of the Acquired Podcast. I went with Ben first last time, so David, introduce yourself. Oh, out of order. Ben always introduces himself first on our... says this is good. I'm going for, I'm going to really bask in this now. I'm David Rosenthal. I am one half of the acquired duo. I'm an angel investor based in San Francisco.

And Brian, I was thinking earlier since you said contest or battle. I think Thunderdome is the correct. Right. The correct thing of what we're doing here. Hey, everyone, Ben Gilbert. The other half of the acquired podcast. And by day at Pioneer Square. labs in Seattle. Well, this is where the rubber meets the road, folks. This is the quarterfinal round. Everyone that is in this round has overcome a competitor. Again, all of this voting happened over the last two weeks on Twitter,

voted on by the TechMeme Ride Home listening audience. Our first matchup is going to be, Reed Hastings of Netflix, who lost to Jeff Bezos of Amazon. And the winning percentage for Jeff Bezos was 77.9% to Reed Hastings, 22.1%. Now, again, we spoke last episode about how if we were going to do seeds, obviously Jeff Bezos would have been one of the seeds. However, I would have thought that this would have been closer in the sense. that. And this is me playing devil's advocate a little bit. Jeff Bezos has changed the way we buy things. And you can make the argument that that's a bigger impact on the economy. But Reed Hastings

has changed the way that we live our lives, our, you know, our recreational lives. Maybe I would make the argument that Reed Hastings... I mean, he invented Netflix and chill. Right. Like, he has more of an impact on how we live our lives every day, maybe than Jeff Bezos. Discuss. Not if Jeff Bezos has anything to say about it, but. Like, Reed Hastings business is probably built upon a business. One of the businesses that Jeff Bezos built feels like one of the challenges that he would have had to overcome.

I also, you know, maybe the other issue is with your audience. You know, had this been like the media gazeder audience, there would have been more of an appreciation of what Reed Hastings had to overcome coming from outside of Hollywood and disrupting that world. Like only recently has Amazon bought MGM. And so the fact that like the way, the power of Hollywood, I think is probably not well understood by people in Silicon Valley, relative to the power that Silicon Valley now has in the world.

And so that feels like one of the reasons why maybe Reed Hastings didn't fare as well. I think that that is 100% the way to frame it for Reed because we know that tech disrupted media, disrupted Hollywood. But that doesn't necessarily mean that until Netflix, tech actually was successful at media, right? Now, you can argue that Steve Jobs via the iTunes store, you know. And Pixar, too. And Pixar, too.

But in the case of iTunes, it was solving media's problems. It was giving them distribution. It was giving them a business model. But before Netflix, I can't think of a tech company that actually, it's like that old thing about when the iPhone came out. Well, computer guys are going to come in and disrupt the phone ecosystem or whatever. No one from Silicon Valley had come in and disrupted. Where was Blockbuster based?

Texas. Right. Houston. In the past. Yeah. In the past. In the past. Right. There's such a good story.

Oh, it was years ago that we did the two part on Netflix on Acquired. But if I'm remembering, right, there's such a good. Like, Blockbuster really should have won. Oh, they had the right strategy. Yeah. It was like a weird shareholder thing. Like they were about to pull the trigger on like putting Netflix in their grave and then sugarholder problems. You know, I will say that in Reed Hastings defense, you know, one of the things is so important about the Netflix story is the pivot from being a DVD focused company to one that was digital and streaming.

You're a quickster? Yeah. Thank you. Yes. It's sort of like was the one from last year that. that, you know, fizzled out also that had like $7 billion in funding. Quibi. Quibi. Thank you. A Quicksster, a quibby, similar. But actually, David. Let me just make my point though. Yeah, yeah. Like, because this was also a bet the farm kind of moment.

And I don't know if you can say whether the rollout was botched or whether the consumer, like the consumers just couldn't see the future and didn't believe in it. And the familiarity and the tactility of DVDs. And I guess like to me, this is like the product learning and the learning about people is that that was so much more present for them, like going to a blockbuster and getting VHS or DVDs was so important. Getting the DVD in the mail was a ritual, and it was understood. And streaming, the performance sucked. You know, your computer sucked. You didn't have your computer hooked up to your TV. Oh, God, Silverlight. Yeah, Silverlight. Microsoft DRM bullshit. It was like worse than flash. At the same time,

Reed was right, you know. That's my point, right? So so many things kind of had to happen. And like, I mean, and I guess I say this also because, you know, when people like asked me about like the hashtag, I have a similar feeling where it's like, you know, had Twitter and social media and Instagram not succeeded and not taken off, you know, no one would give a shit about like me or the hashtag. So the same thing was true with like, you know, Netflix. The streaming platforms had to come out.

Computers had to get faster. A lot of things that we assumed were going to happen did. And as a result, Netflix was able to. way. Right? Did the episode, and I know I listened to it. But where do you come down on the idea that they, of course, posit these days, which is, well, we always knew we were going to do streaming. There was a reason why it's called Netflix and it's not DVD by mail.com. Do you believe that, that they always had this vision and that the DVD by mail was just a placeholder for them? Not this exact vision, but I totally believe that they were going to be whatever the form of movies on the internet takes.

And I really do think most big companies become valuable by having one multibillion dollar innovation. And Netflix has had three. And it's quite remarkable. Like even Apple's only had two or three. Microsoft has had two in Windows and Office. Netflix had, we are going to figure out how to get a distribution by doing this mail thing, and we're going to time it perfectly with when you can mail DVDs, and we're going to make that cost effective, and we're going to shock the world by saying, keep a DVD as long as you want.

We're not like Blockbuster, where you have to return it two days later. Amazing, disruptive concept. Then again, with streaming, then again with original content. Like, they kicked off this new golden era of television that we live in where the power has sort of shifted one click in the value chain away from the studios and actually to these platforms, which maybe that's good, maybe that's not, but it's totally disruptive. Actually, I mean, to build on that, what you're suggesting I think is super important because tech companies have always wanted to get free labor and free content. And so crowdsourcing was the methodology by which you would fill your feeds, your news feed, your Instagram profiles.

And if you motivated it with likes and other types of dopamine, then you can get people to work for free. So Netflix's going in the other direction and saying actually quality content is important and it is worth paying for and we're going to spend more than Hollywood currently does. In some ways. Business model. Well, in some ways has ushered in. Yes, I mean, YouTube probably, you know, there's no founder of YouTube in here.

But YouTube, but also Netflix sort of ushered in what is happening now with the creator economy where people have an expectation that content is worth paying for. Yep. At the end of the day, so Brian started this matchup by talking about the fact that Netflix really revolutionized how so many people are entertained and Amazon and sort of all they did was sort of modernize the way that we get stuff. And I was just looking at the numbers to try and figure out how many people are, it's actually quite interesting.

There are about 200 million prime members and about 200 million Netflix subscribers. It's interesting to note that. So that's crazy that Prime Video hasn't actually taken a cut of Netflix. Well, okay, but here's the thing. Like, I pay Netflix $216 per year before sales tax. I pay Amazon a ungodly crap to lots of thousands of dollars. You know what? Can I make one more analogy because this was the matchup of Bezos versus Hasing, so Amazon

versus Netflix. If you want to give credit to Bezos for this. idea of as people ragged on them for years and years and years, we're never going to make money because we're reinvesting in the company. What is, did, which was right? Which was right. And did Hastings, like, bought, maybe not steal that from Bezos, the idea that we're going to spend, what is it, close to $20 billion on content creation this year. So like we're not, I know that that Netflix is making money, but this idea that you have to spend money to make money, I think actually now that I'm thinking about it, like the cable TV model from the 70s and the 80s comes to that

where it's like you create loads of debt because you can service the debt with the monthly subscription revenue and things like that. But there's an analogy there. Private equity, baby. Yeah, yeah. The spending money to make money is both Bezos and Hastings believe in that. Well, when you also, you asked Brian, did, was it the plan from the very beginning for Netflix to become what it is today. I don't know that, I don't remember enough to answer that exactly, but I will say in a sort of feather in Reed's entrepreneurial hat, this is their outcome where they've gotten to is wholly path dependent. Like they could not have done streaming if they had not had not done DVD. They could not have done original content if they hadn't done streaming in DVD before. It all stacked

up. And it goes back to like the wedge, the thing. that was brilliant, there was the consumer demand. And like Ben, you were saying, it was so much better to use Netflix than to use Blockbuster and not have late fees. But the real thing that they saw was the first sale doctrine allowed a tech company to enter into the movie business without having to deal with the movie studios because they bought the DVDs and then legally they could do whatever they wanted with them and they didn't have to go talk to the studios in the beginning.

And now, of course, they're taking over the studios. but they were able to get this wedge in that was absolutely brilliant. I forgot about that for sale doctrine, David. That's a good call. Well, and now it's all about owning IP and dealing with, like, the ownership of ideas. But I thought that was a great point, too, that whether they were brilliant enough to have a plan where A builds to B, builds to C, that's a good entrepreneur. Another good entrepreneur is someone that doesn't have the plan, but once A happens, you see that B is possible. And once B happens, you see that C is possible so that you see the angles and you play them.

So there's two different kinds of entrepreneurs, the one with the grand plan the whole way, and the one that sees what has been enabled by the success that you've already achieved, essentially. moving on to the next matchup, which is Jack Dorsey versus Elon Musk. And remember, if you remember our previous episode, Jack Dorsey was the big upset against Mark Zuckerberg. But he apparently hit a brick wall when it comes to Elon Musk. Now, the percentages are, you know, one of the closest. I want to look up who actually has more followers on Twitter, Elon or Jack. Do that. I'm going to say the fact that like Elon can be Jack on his own platform is something of a,

like that is a real. I feel like it's like Elon, Donald Trump, and like LeBron James. By the way, guys, do you, do, if you don't know, if you know, I'm saying, but guess, how many followers do you think Jack has? 15 million. Yeah, I was going to say 13. 20 million. 5.6.

Oh, what? Wow. And nothing. I was going to, Elon probably has like 35. What, did he get booted off of who to follow list? Elon has 59.9 million. I was going to say, wow. By the time this episode comes out, he will have 60 million.

Well, listen, here's the percentage is how it broke down. Elon Musk won 73.2% to 26.8%. And again, that's closer than most of these contests. So on the one hand, you could say that. The home court advantage didn't help Jack all that much. At the same time, when I tweeted this, I said, Jack Dorsey of Twitter versus Elon Musk of memes. Like, I put in parentheses, why are, you know, so it's not necessarily that Jack is the meme lord that Elon Musk is. But, all right, our job right now.

By the way, Elon is bigger than LeBron on Twitter. Really? I didn't realize. Not Instagram, though. That's good. Wait, who's the most followed person on Twitter right now? Quick. I don't know. Somebody Google that one.

Maybe Elon. It's entirely, no, it's probably like, um, uh, uh, uh, Ronaldo or, or somebody like that. Yeah. Um, uh, it's, uh, Obama. What? Uh, no. It's like every time I see someone, they're like, yeah. So, Obama's rocking a hundred and thirty million. Whoa, that's more than LeBron has on Instagram, which is 98 million. Wow. Okay. Okay. Somebody. We got a, yeah, Justin Bieber has 114 million and Katie Perry has this is wildly going off the rails yeah well because we need to do we need to do justice to jack dorsey and i'm gonna i'm gonna do it this way which is uh here's here's

two channels and then you can add other channels number one unlike a lot of other people on these lists multiple companies founded multiple hugely successful companies straight But he's up against the only other guy on this list who's currently CEO of two companies. Right. And I said straight, but I know it's Square. But like Square was early to FinTech, which is so huge right now. But then what I said in the last episode, which was that Twitter, which again was Jack's idea. I mean, kind of hazy, but Jack's idea-ish. He has the design for status on a, you know, and line a piece of paper.

But that SAT.us. That is the first sort of kind of new idea after Facebook kind of solves social media in the sense that it's more real time and things like that. Look, you know, if we talk about...

In both cases, though. Yeah, right? You know what, Chris, you should take this. Go. Yeah, go. I mean, but the parallels to me, again, a lot of what we're talking about are these... I think, Ben, you might said it, like these small incremental, but very distilled, you know, like, what is it, like ice wine

kind of, you know, distillations of an idea brought to market and then socialized and built into these behemoths. And in the case of Twitter, it was recognizing that Facebook was a desktop app and didn't work over SMS, which was the new mobile frontier. So the fact that Twitter was largely an SMS app in the beginning is really what separated it and also forced a series of constraints on the product experience. I mean, that's where the hashtag came from. You know, we had 140 characters and I had to make use of that to, you know, solve that problem. Additionally, Square came out of the, which doesn't exist anymore in the iPhone, the headphone jack being used as a credit card reader, which when I first saw that, that was like one of those mind-blowing

moments where you're like, you can do that. Amazing. What? So I feel like those, those, two innovations around, and again, like, I guess I relate to it because, you know, the hashtag came out of the hardware keyboard, the numeric keypad that had an asterisk and a pound symbol on it, and the pound symbol wasn't being used for anything, so I got to use it. You know, there was like the headphone jack that you're like, how do you do payments on the mobile phone? You're like, oh, the headphone jack, right, because you listen to me, like, what? So we're, uh, those two things. With all the, with Jack and all the, and all the Twitter folks in the early days? I was, you know, I was in their social circles.

You know, I could, like, go into, like, Twitter's headquarters. I was more friends with, like, Blaine and some of the more technical folks. I mean, I knew Jack when he was an engineer. I mean, it's also worth remembering that there was a internecine period where, you know, Jack was kind of out of the company and there was a lot of, like, weird politics. And, you know, Twitter itself was a shit show for a long time. The early technical guys that really helped at scale, like, like RSA was there. And Alex Payne.

Yep, Alex Payne. For sure. Yeah, Blaine. Yeah, a lot of those folks. And anyways, you know, Jack sort of persisted. Maybe he was like the last guy out, you know, like he had to turn the lights off and that's how he became CEO. I don't know. But I just, I think it's really important to sort of recognize those innovations built on what I see as almost like drops in a pond that just have these reverberations and ripples out. Whereas, you know, Alon comes along and, you know, granted, I'm sure we'll get to him, you know, and does things that are literally like rocket science or, you know, like car engineering. Like those are not just kind of like one little thing that's like, oh, look, there's those

like a random appendage, you know, that's like built into the apparatus of reality that I can like build upon. Well, let's, let's hold. Okay. Let's without drifting into Elon territory yet, just to give Jack his due. There is this remarkable thing where in general in life, I was like the adage of once you're lucky, twice you're good. and like for Jack, you know, obviously how painful it must be getting ousted when something that was really kind of your idea did blow up, did become this unbelievable, like nothing grew as fast ever as Twitter did. It was just this unbelievable growth story. And that being ousted and saying like, you know what, like, I'm going to gather all the chutzpah I can and I'm going to, I have another really good idea. And of course, like, it's not just that he had an idea. He went to St. Louis and he knew Jim and, you know, they sort of started.

this. But, like, unbelievable that his product vision was sort of validated as a visionary that, like, yep, you got another one in you, and it's just as big. Yeah. We're talking about, you know, finding, Chris is saying, like, finding little niche things like the headphone jack and what can we use it for. And the idea that, like, nothing, nothing was as impenetrable as payments and banking and things like that. And I think you guys have done an episode on it about like, you know, the ways that he saw the way in.

I've heard stories about the people that like explained. Like the wedges. The wedges into finance. But the first person to crack finance being him and leading to this fintech revolution, I think, can't be underestimated, especially as the fintech revolution is basically changing the world right now. I think you could maybe even argue that Jack has, it's not organized as such, but he's got three wins, not just two. He's got Twitter, the original square, and then the cash app. Yep. Have you guys done a, you did a specific episode on the cash app? No, we should.

And it was before the rise of the cash app. Okay, because I've, I've, I've obliquely mentioned this on the podcast before about the cash app alone as a product is worth. you know, such a deep dive in like Harvard Business School, like just the way that they've made that successful. Okay, we should. Actually, before this instance, this is like, you know, Jack's last kind of, you know, I suppose. Yes.

I do think, you know, just as Larry Ellison sits in my mind as sort of a Batman supervillain, I do think that like the journey of Jack is interesting in a, I don't want to say, the guru sort of sense. You know, I mean, not only does he sort of like dress the part and, you know, has the beard, et cetera, but like I do feel like he's one that has gone through a personal transformation of sorts where his, you know, he's sort of in the Tim Ferriss camp of like, you know, mind, body alteration towards a almost like more, I don't want to say like spiritual presence, but in the sense that his lifestyle is also influential.

In the same way, like, you know, Brian, you were talking about Oprah. Like in terms of the way that people perceive the way he eats, you know, and meditates and sleeps and, you know, does cold plunges and all these like weird esoteric things, I just feel like that's also like worth thinking about because the rest of the folks who are kind of on this list are a little bit more straight in the sort of, you know, normal, normally kind of in a way of being. Jack move the culture, for sure. Yeah. I just want to put that out there as, you know. No, and actually, Chris, that's an important point because I think both you and I, well, obviously you, but me as well, Jack, I've never met him, but I have more friends that have worked for him and know him personally than almost anyone else on this list. And it has been an evolution. And listen, you know, even Twitter, if we're talking about like, you know, Snapchat coming back, Snap and Twitter have been the comeback stories of, in terms of stocks and social media companies over the last couple of years. So there's that as well, you know, that you can learn and evolve and things like that. It is funny that Patrick Collison is coming up next,

seeing as how we're talking about, you know, fintech and things like that. Again, if you remember from the last episode, Patrick barely beat Oprah, which, listen, again, to be a pundit here. Such a crazy thing to say. Yeah, listen, Oprah should have trounced him. Now, this was a trouncing. We should have, we should have tipped the scales on that one. Yeah. I almost wanted to because I thought it was going to be 50-50, and then I was just going to make the call, you know, because because this, this matchup is Patrick Collison versus Bill Gates.

So I would have loved to have seen Cappellupitz in this one. Right, right, right. I would have loved to have seen Oprah versus Bill Gates. But yeah, this is a, Bill Gates wins this one, 88.9% to 11.1%. I don't know to what degree, to be honest with you, this was. putting Patrick in here was my sort of sop towards like the next generation. So I don't know to what degree we can really make an argument that he's a great entrepreneur yet because he's still so young. Come on. He's he's he's a world class entrepreneur. He's one of the best entrepreneurs that

ever lived. But you have like the most proven entrepreneur versus an in-flight entrepreneur. Okay. So let's do this now though. Make the case, Ben, for why he is. Let's imagine that he will prove to be the best entrepreneur of his generation. Why do you think that he might be? Well, Stripe's core product offering probably created more value in the world as a as a platform than Square. Then just like just to riff off the previous conversation. Yeah, I agree with that. The amount of commerce that can happen digitally on the internet because Stripe exists is like a non-fathomable amount. So you're not including the cash app, just Square pre-cash app. Yes. Yes. So like, Let's just talk, like, I guess I am constantly in awe of the amount of innovation that has been able to happen because Stripe as a product exists.

Just like, you know, it's leaps and bounds better than Brain Tree, which was leaps and bounds better than authorized.net and all the garbage that came before it. So there's that. And of course, this industry is impenetrable. So amazing that they were able to do this in just five lines of code. Now you can accept credit card in your application. And flash forward 10 years, the product velocity that they have today is unbelievable for a company of their scale. And the amount of places that they're playing in the value chain and amount of different customers they serve all with like a pretty simple, like elegant way of understanding what each of these products is, except maybe Striped Treasury, which like I'm still trying to wrap my head around. It's amazing.

Like, and I just think like that combined with the cultural leadership. that the Collison brothers have at Stripe versus any other company of that scale where you get employees fetching about the leadership. You just never, ever hear that at Stripe. It's nothing but reference. I'm going to use another Chris Rock line, but I'm going to paraphrase it because I don't want to use the real line. But there's the Chris Rock line that my wife owns ketchup. The audacity to essentially try to own money, like if we're talking about the chutzpah of an entrepreneur. And we can get into the idea of, you know, APIs all the way down and things like that. But the audacity to be like, we're going to go after money is crazy. And they're doing it.

I mean, like, I think the, you have to start with, and I think this is probably why they're, they're brilliant is, you know, because you start with like, well, what is ketchup? Like, what is money? And the fact that the internet didn't come with payments built in that 402 was never specified kind of left this wide keeping hole. And as Ben said, there were companies that sort of built it in. But again, they were so, you see this over and over again where companies that are wedded to the structures and institutions of the past end up getting swept away in the dustbin of history, so to speak, because they're not reconceiving of what the thing is.

you know, like ketchup as a condiment, probably again, like whoever the entrepreneur was that figured out a little bit of like, you know, tomatoes, which were in rapid abundance and some salt and, you know, some other things put together in a can and took advantage of a new medium, which was cans and canning, like, you know, caused this explosion of all sorts of products from pizza to spaghetti to who knows what else. And in a similar way, the transaction of commerce on the internet was something that was always wanting to happen, but it wasn't enabled. And it wasn't easy enough. And, you know, I can say this because of the work that I did on Oath, like, wanting to move beyond passwords was so hard. It was such a common thing to do. And you had to make

it so mind-numbingly simple and basic to get it adopted. And I feel like Stripe took the same approach to say, look, payments don't need to be hard. We've been exchanging value, you know, since shells, you know, this is a common thing for humans to do. Let's conceive of it in that paradigm for the medium and the moment that we live in. And that, I think, is what sort of separates Colson from, you know, the ones that came before. Chris, would you buy striped stock if it were public today at $100 billion market cap? I probably would. I mean, because honestly, there's still more growth to do. There's still more room to grow, you know, whether they're going to be paving the roads of the metaverse. Like, it just seems like they are, they are like, I mean, all of the stuff

happening about the App Store or whatever is this adjacent space where Stripe just continues to move forward and they're part of so many transactions. And as I understand it, once you're part of the Stripe Metaverse, your customers are locked in there. You can't get them out. And so that's a really, really big moat. And I'm sure that's why one, they command the valuation that they have and why everyone wants to get in there. Because they realize that that sunk cost is going to be impossible to recoup. Here's an interesting thought, which is either, a bull or a bear case for stripe and certainly is an argument that we are going to need to redo this list at some point in time because there's a whole category of folks that are not on.

Are you going crypto, David? I'm saying that Bitcoin's market cap is about 8x stripes right now. So think about that and they were both started it like right around the same time. Justing is we, this is a common parlance right now. VCs and people in Silicon Valley would pay basically any dollar amount to get their hands on stripe shares right now. Stripe is a meme as much as a company. Just like Tesla.

But yeah, what is wild, though, and yet Bitcoin is, you know, 8X hired valued right now. Well, I wanted to, I almost put, I wanted to do Shopify and do Toby on this list, right? And I'm not saying that Patrick is more important. But the thing that put Patrick on over Toby was that like, where would Shopify be without Stripe? Right. So when we're talking about this idea of like the enabling other things, the platforms, the APIs and all that stuff, like it's such going to money on this level is so fundamental. And I get what you're saying about Bitcoin and crypto and all those things. That's not been proven yet.

But right now today what Stripe is doing in real world use cases. And again, please don't at me, crypto people. But like it's happening right now for, you know, a friggin pizza place around the corner. Also, like, these things do not seem like they're incompatible, right? I mean, like, strength. No, no, no, no. If it doesn't already support crypto, can. All right, all right.

Whether-Rymole hates crypto, go on. Exactly, right. I think if he hated Bitcoin, is that the, yeah. Something like that. Yeah. Oh, I'm hot on Solano these days. So, yes, I'm off Bitcoin. Yeah, Salinas had a bad week.

Yeah, yeah, yeah, yeah. I know, yeah. All right, moving on. This is one, I have an interesting case to make on this one. So the next matchup is Larry and Sergey of Google versus Steve Jobs. Now, again, you're going against Steve Jobs. Who's going to beat Steve Jobs? He wins 76.7% to 23.3%, which again, if we're looking at the numbers, it's closer than other competition.

I'm going to throw this out there. This is the one time that I'm going to be Super Devils advocate. it. I don't think that Larry and Sergey are good entrepreneurs at all. And I think Chris, you might have alluded to that also. I don't think they are at all. I mean, I think the point that you guys made before where they kind of had like one good idea and then they just kind of like built it out. You know, I think is one part of it. I think the bigger part of it is I think they just don't give a shit. Like they kind of, they don't really have a world changing world building like play, right? Like, Ailon wants to go to Mars. Like, you know, Bill Gates took over

the world with his software and is now curing malaria. You know, like, Larry and Sergey, like, wants to, I mean, I think is it's, Larry wants to go, I think, do either autonomous vehicles or flying cars and Sergey wants to wear strange shoes. You know what I mean? Like, I don't really get where they're going. Now, again, the devil's advocate, my own devil's advocate, they, if you put it that way, they're the best entrepreneurs because they're literally creating the moonshots when other people aren't. So they have this one great idea that gives them a shit ton of money, And maybe only Elon is the other person that's like, now that I have this money, I want to do X, Y, and Z that no one's ever done that no one could ever dream of. So for the entrepreneurial spirit in theory, they- So this raises a question, right? And I think this is one that I've been trying to like figure out in this mix, which is the degree to which as sort of a brilliant entrepreneur, you have to actually engage with people and society and the rest of the smelly masses.

and I feel like Larry and Sergey just don't have an interest in it. Whereas there are other folks who are like in the arena and are willing to go there, even if it's uncomfortable. I feel like, you know, Alon will go to like the gala's and stuff like that with Grimes, not necessarily because he wants to, but because like he's willing to. He's willing to be visible. He's willing to be out there. And he's willing to do that shitty work and dealing with humans that just don't understand

like his master plan and vision. And I feel like Larry and Sergey are kind of like, they did like the Ellison thing. They bought their island and now they're going to like live there because, you know, screw humans. You know, billionaires stuff. And like Elon doesn't really do billionaire stuff. Like he lives in a pre-fab house. Like he lives in a two-bedroom little like maybe 2,000 tops square foot house. That's what I mean.

No, it's way less than that. Like they're building like this vision in this like world that they want. to sort of get to on behalf of other humans, like on behalf of the human race. And maybe I'm, I don't know, you know, I worked at Google. Like I have a lot of like respect for the company and what it achieved and its ambitions to, you know, organize the world's information to make it useful. Like that is an amazing goal. But I kind of feel like they got to a certain point and then they kind of like checked out. And that to me feels like you've like left the game like sort of in the sixth inning. And there's still so much more to do. So that's where I'm kind of like a hundred just

100% I think that they checked out. They did do the thing where it's like, you know what, I'm worth billions of dollars. I can have a yacht. I can be in the Mediterranean. Or I think one of them is in Tahitian island and has been since the beginning of coming. Yes, that's right. You can do these things, right? And life is short, you know?

And no one's blaming you, but you're not going to win our contest that way. So let me. That's right. Okay. Let me say, I like that. Two sides of the coin here, which is number one. both of these dudes were academics. They were going the PhD route.

They were going the, we're going to be, they would be professors somewhere with tenure, whatever, whatever. I'm not saying that you can't suddenly become an entrepreneur from another walk of life or whatever. But I don't think,

I would argue that they, I don't think that they had the entrepreneur, I don't know, spirit gift, whatever that is. that that's what i'm saying yeah like when it comes to the grit of of being an entrepreneur in the business world okay they they would prefer to seem like the least gritty people on this list yeah let me and again i let me also clarify that isn't to diminish their achievements that isn't to say that they're less amazing i i think when you evaluate them as entrepreneurs the type of shanking that zuckerberg will do like i just feel like they'd be like they'd leave the arena you know and they'd

like walk out and they'd like too much blood can i can i do real quick two two to two to go ahead. Yes. Last little feathers for them. YouTube and Android. A huge, huge feather. Now, obviously they didn't build those, but I don't think they would have acquired them if they weren't, especially Android, if they weren't like, no, we got to do this. Okay, but David, now I know I've seen the emails that I think it's Larry that's like we should buy Android and things like this. But also, did they just do the thing that is not since Zuckerberg common, which is they did the thing, which is we'll get adults in the room. And they got adults. in the room that made those decisions and made those things happen.

Right. I'm not saying that they should win. I'm just saying, like, I think we got to give them some credit for YouTube. No, no. Okay, before we leave them, I want to make this very, very, very strong case. The modern idea of how a tech startup works, the culture, the way it's organized, the way you hire is them. So even if we don't think that they have the shivability of Mark Zuckerberg, they're not as bloodthirsty. They also did have the insight, or at least the, that was in their nature.

We want to create a place where we want to work where the best and brightest are here. Yeah, I think that's an excellent point. Yeah. I think like having worked there and worked in the Google campus and there was a lot more playfulness and a lot more generosity in, you know, for ideas. But, you know, you did. There was a kind of credentialing and a very kind of quasi arrogant elitist. You know, you had to be super smart.

Did you feel like you were like literally like, wow, this is like the assemblage of the best and brightest people on the planet right now? The way that I would, the way that I would evaluate it is on a couple different like dimensions. Because I want to build on Brian's point by just saying that Google's culture did kind of, it's one of the things that permeated the valley and spread out. And so when I would go to other companies and there were people from Google, there was a language in a way that we would talk that was so specific to where we came from. And so that is very important in terms of influence. In terms of my experience going to Google in 2010 and then working on Google Plus, the huge deficit that Google obviously had was they had very, very smart engineers that knew nothing

about people and didn't care about people. And so that may also explain my previous bias where I think about Larry and Sergey and there were just aloof. You know, you think about Google Glass versus like the product that, you know, Facebook just launched, you know, with their spectacles. There's a sensitivity for fashion and for taste and for culture and for all that stuff that just feels like noise, but is actually quite important to getting things adopted and used in society. That hubris and arrogance was a type of deficiency and there was like defensiveness around it that I think Googler's not all,

I don't want to overgeneralize, but we're reluctant to really care about. And once we entered into the social era of technology, pure mathematical superiority was no longer sufficient to build products that people really wanted to use and loved. Okay, y'all. That ends the quarterfinals. We're on to the semifinals, and so that means there's only three more matchups. With Larry and Sergey bowing out. That brings us. back to the other side of the brackets. So we have Jeff Bezos going against Elon Musk,

which, to be honest with you, ahead of this, I'm not sure I could have called this one. And it is closer. This might be the second or third closest one of the list. Elon Musk. So wait. So hang on before you tell us, a quick proposal here. So the email that you sent us has a bunch of question marks. Right, because these hadn't, these votes hadn't happened yet. So do you want to guess? Or should we call our picks definitive and argue and see we can come to a consensus on this call? Okay. All right. No, let's let's let's let's let's I like the idea of guessing and then then we want to hear what the public said.

Guess who you think won and and try to give me some numbers. I'm going with Elon 6040. Exactly what I was going to say 74, you know, 36. Elon wins 62.3 to 36. 7.7. Boom, Rosenthal. Yeah, very good. Which means we have to say goodbye to Jeff Bezos. He's going on his rocket ship anyways. Yeah, he's saying goodbye to all of us too. I was just going to say that. Okay. All right. Look, there's no other way to say this. He was one of the earliest entrepreneurs of the internet era. And I said in my book that there's no one else.

like even you know Mark Andresen had to go off and become a VC like the person that did the first e-commerce company created the category proved that people that you could make money on the internet did it until about six

what is it three months ago and then we can go into all of the other things the you know spending money being willing to lose money forever and ever to build the business to to AWS to I don't know. To be able to attract the shareholders who are going to bear with you for 25 years while you lose money. We're even talking about Netflix's recommendation engine.

The recommendation engine comes from the software innovations that Amazon created. You know, like filtering. I mean, I don't know even where to go with this. Not to mention just like the supply chain innovation. The ability, you know, and like prime and like the membership. thing. And prime warehousing, fulfillment centers, home delivery. I feel like all the best business quotes are Jeff Bezos quotes. Like any time, like your margin is my opportunity or when you're talking about the AWS primitives

that we're going to build on top of, it's like Jeff reading a sci-fi book. Or when you talk about the idea that, you know, of platforms, that it wasn't until we had UPS and the internet that you could build Amazon, you know, that he took advantage of the giants that came before him. Like, he has this unbelievable conciseness to be able to communicate business concepts that I think inspire generations. And I'll say, uh, so this is going to sound right, but I actually really believe it and I think it's true in Bezos's case. All of the amazing stuff that, uh, he and Amazon created, I think the most amazing thing is the culture at Amazon. Uh, And before Amazon, just like we were saying by the way, how would you sort of, you know, describe it, right?

Given my description of Google, how would you talk about Amazon? It's so different, right? Like, they're the most innovative large company. Yeah. I would say it's the first, to my mind, again, I've never worked there, but just studying it from afar and having lots of friends who do. To my mind, Amazon is the first company of a new. like, I hate this word, but, you know, paradigm of how to organize companies. Like, they, like, like, you know, Ford was like the first, like, you know,

industrial, like, you know, a manufacturing line, assembly line company. Like, Amazon is the first decentralized company. Like, they really mean the two pizza team thing. Yeah, I mean, actually, like, that is exactly how Uber was organized as well. And we had folks at the top from Amazon that designed it more or less after the structure of Amazon. We're starting to see it disseminate out into other companies like it. But it's just going to continue. Like it's a wholly different way of conceiving like what the organization is and how it operates and how innovation happens and what the, you know, what we do here.

And, you know, again, like lots of people don't like it. It has its challenges. You know, there's some things are great for the world. There's some things are bad for the world with it. But it was wholly new. And I think that's like the, to my mind, the biggest thing that Bezos contributed. Jeff Bezos may not be the best entrepreneur on this list. We got Bezos, Musk, Bill Gates, and Steve Jobs, obviously, because the people have voted him out. But he is the best business person on this list. I mean, I... Well, given, you know, I think the fact that Jeff Bezos started in the financial world, right? He started, and Brian, you could probably speak to this better than I can, but started in...

Edge fund. Yeah, exactly, right? And took that mentality and brought it. to the internet and then started with books because of the various attributes of selling books in order to then extend those patterns to every other form of commerce is unique in this list. If we're talking about the entrepreneurs that saw the opportunity of the internet era, he literally was at D.E. Shaw saw that usage of the internet was going up something like 37,000 percent a month or something like that and was like, shit, I don't care. I'm going to do something here. You're never going to see anything like that, growth like that outside of a petri dish, right? So if we're talking about... He was the Sam Beckman-Feed of his era.

If we're talking about of the internet entrepreneurs, beyond Bill Gates, beyond Steve Jobs, beyond any of them, he's the one that in this era is like, I see the tidal wave of history, planning my flag, waiting for the wave to come. But that's not enough for an entrepreneur. Lots of people saw the wave coming. And again, he's the one that wrote it all the way. So it's such a good point. Like if you think about the five large tech companies,

you've got Facebook, Amazon, Apple, Microsoft, Google. And quick diatribe, this notion of fang, including Netflix in there instead of Microsoft, is just stupid. Like the company is not in the same league. Market-tapped-wise, revenue-wise. That's just a Wall Street thing because it was all the stocks going up at the same time. So you look at those five companies.

Amazon is the only one that was a dot-com company that survived the dot-com bubble. Apple and Microsoft are from the 70s. Facebook and Google are post-bubble. Yahoo's not around? I actually think like, so like my, I actually think Jeff Bezos is a better business person, but not a better entrepreneur than Elon Musk. Because I think Elon Musk is the most impressive modern industrialist. Like the fact that he's Tesla's chief engineer,

I mean, you look at like they're having the model three shortages and he's sleeping at the factory. Like it's just a very different type of person and mentality than Jeff. Maybe Jeff was doing that back in the book. I'm sure like when they were trying to figure out how to make every prime order arrive on time. He was doing stuff like that. He was down on the floor, boxing the orders up together.

And his big innovation was he bought knee pads for everybody. And then someone was like, well, we could also have desks. Tables, yeah. Tables. Yeah, I'll say it's funny. Well, not technically true anymore because we had an awesome acquired listener in our Slack community organize a SpaceX secondary SPV. So I do, through via, it's secondarily.

Yeah, hashtag, oh yeah, I'm going to take a lot of credit for SpaceX. But of all the fan companies, and I'm looking down the list, every other company on this list, I only hold Amazon in my personal account, and it is my largest position in my personal account. Yeah, Amazon was one of those stocks that for years, I was like, oh, I missed it. It's gone up so much. I missed it. It's gone up so much I missed it. And then, I don't know. And then it still had 50x left.

10 years ago, right? I'm just like, fuck it. I don't care. And by the way, I don't even know what exit is, but whatever. I'm going to do one thing to close out with Bezos, because this might lead us into eventually the Steve Jobs conversation. But to use, Chris knows I love to use soccer analogies, but I wonder what it means when an entrepreneur like this leaves a company in the sense that like when Alex Ferguson

left Manchester United, you know, Alex Ferguson is someone, a soccer coach or a football manager that people read business people read his book because he was perhaps the most successful professional sports manager of the last 50 years so what does that mean by the book was written by mike maritz too which makes there you go exactly reading in and of itself building culture building a way a process a way of doing business um you know it it's looking good for manchester united this year because they got a Ronaldo back and things like that. But they have not been successful since this person that transformed their fortune for 20 years left. I wonder to what degree, if we did this five years, 10 years from now, would we look differently at Amazon if the transition?

Would it be like, oh, my God, Bezos was more of a genius or less of a genius? Because, you know, we'll see. We'll find out. With that, I will say like, yeah, go ahead. Just to add to this, like the fact that they managed the transition as well as they did this year, where, you know, it really felt like, you know, Bezos was this sort of asymptotic figure, you know, ahead, you know, the S.S. Amazon, so to speak. And then he was able to step aside and let Andy Jassy come in and, you know, the guy who's, you know,

in charge of AWS. And there wasn't a huge disruption. I mean, I feel like when Tim Cook took over from Steve Jobs, like, that was another watershed moment. And a similar question could have been asked. And I think in this moment, the question of what Amazon becomes in the Jassy era is far less clear than I think, you know, Apple, right? I mean, Steve Jobs even had sort of parting words like, oh, I cracked the, you know, TV and all these other things. Right. And it was sort of just building out generation. of the iPhone.

For Amazon, what is the next set of acts? And has Bezos left the right set of playbooks or the right set of roadmaps or what? I mean, there's his leadership principles. He's basically codified his belief of what entrepreneurship is into a set of principles and left them on tablets for the company.

Well, and that's what I think. That's kind of what I meant about that culture. Like the way it works, it's not like some genius. It's not like Bezos hands down. You look at the fire fund, right? Like, it's the way that the organization works is it's like complexity theory. You know, it's just like built on like lots and lots of little experiments.

And then the things that work, you feed them and you're just constantly running experiments. And to build on that, though, the principle of being the world's most customer-centric company, like, is a robust statement. Yeah. That as long as you can continue to agree on who the customer is, that will probably be the biggest political question going forward for Amazon, then I do think that Amazon has that place and position and can hold on to it, because having a unifying principle or idea to bring together decentralized units is probably the most important thing that you can imagine.

And so I think to your point about culture being important, decentralized culture that remains coherent over time, is or could be one of the biggest innovations that persists. I think also when we're talking, maybe if we ever do another one of these, it should be the best CEO, the World Cup of CEOs or the World Cup of Managers or something like that. When you do a transition with a company, it helps if the entrepreneur, the founder, wants to leave. Now, Steve Jobs didn't want to leave. God wanted him to leave, I guess.

You know, it helps. God and kill Emilio. Yes. That's right. Okay, right. I forgot about the first time he looked. That's right. But I think it helps that Bezos is like, I'm good, right?

And so if we ever do another one of these and we'd have to have Tim Cook in there in terms of like the best CEOs and things like that. By the way, Brian, is that Bezos on the wall behind you? Which one? Yeah, that one is when he was Time Magazine Person of the Year in 1999. 99. I mean, that is a run. That is a run. Yeah.

Okay. I'm transitioning to the second semi-final, which is perhaps the most classic matchup you could have in a tournament like this. Class of Titans. This is what the punters and the stand. paid their tickets for. It is Steve Jobs versus Bill Gates. I mean, it's to the death.

Taste versus iron. Okay, you know what? We're going to have, we're, we're not going to talk about Steve Jobs right now because Steve Jobs beat Bill Gates 71.3% to 28.7%. Right, 71.3% to 28.7%. So one of, in the middle of the road, in terms of, of the percentages in terms of victory. I want to come back to that point about taste when we get to Steve Jobs.

But I would make an argument. Again, I don't mean to be doing this, like going against what the voters have said. Bill Gates is a better entrepreneur, capital E, than Steve Jobs. Yes, no. Am I canceled? He is a... This is hard. I mean, it really depends on...

This brings it back to the very first thing that we talked about. Chris and I sort of debating what is entrepreneurship. Because Steve Jobs is a better artist. And he's better at creating products that people love. Creating product. He is a far better business person, strategist. He is so good at capturing value that they create. What is the difference?

between an entrepreneur that creates a product and an entrepreneur that creates a business so they're a business person. That's a good question. You know, to me, this, what, with this, what it, it feels like these are two different either archetypes or sort of heroes or, you know, like there's Batman and there's Superman and they're like not the same. Yes, I love that. And to me, I feel like we have visionaries, people who see the future and see the world differently and are willing to, thank you. I was getting there. But yes, are willing to totally Batman, by the way. Yeah, put ads. Jobs being Superman. Out there, you know, where like there's a person throwing a hammer at, you know, big brother and willing to take that on. And of course, you know, eventually becomes

big brother, whatever, it's fine. On the other hand, there is someone who just, you know, is, is a meticulous, like, you know, planner and executor and finds ways of almost like jujitsu using the momentum of other players in the space to benefit their own platform. And that is why when we evaluate Zuckerberg, like, Bill Gates is not far behind because Zuckerberg absorbs, I mean, he's like rogue, you know, like with the X-Men, who just like absorbs all the talent of people around him and all their ideas. Like, he did that with Bill Gates. He's like Robin, too, with Batman. Robin was different. Like he is, he's the Batman. He's the next actor to play Batman. Whoever is the Robin that wanted to become Batman and was like sort of jealous of him, but sort of

also was Robin. Yeah, yeah. You're talking about Zuck wanting to be Gates. Right. That was what I meant. Yes. And in the sense that, and he did, if you think about the Windows platform and you think about what's happening now with the App Store, right? You think about how Steve Jobs didn't want the app store on the phone. He resisted it because everything that was going to be on this pristine, perfect device had to sort of come from the godhead directly, you know, in, talking too much about Steve Jobs. This is, fair, fair. I thought I was talking about Bill Gates. Bill Gates, right. I was comparing and contrasting these two archetypes. All right. Where one is a visionary and the other is the executor. And I'm drawing a parallel between

the ways in which first Bill Gates created the Windows platform, which was actually a lot more open and free. And I find this very almost offensive to me because of the work that I did on Mozilla and Firefox and fighting against Internet Explorer, yet Microsoft and Windows was more open than the Apple ecosystem, which I live in now. So the irony of these things is very Windows Explorer, which was, which was Mosaic. Yeah, yeah, yeah. Well, okay, anyway, like the fact that Windows enabled, just like Stripe, all of these different players to basically become, you know, or join the computing revolution, provided again all roads led back to Windows, that was the Bill Gates playbook. And then Zuck saw that into the same thing with a Facebook platform.

Right. Now, it's even worse than that because in my research, and I've only found this in a couple of places, the idea that the Microsoft motto, was a Windows software on every computer in the world. It wasn't that. Microsoft software. It was Microsoft software. So if we go back to the idea of only one good idea. Wait, no. It was a computer on every desktop or every desk.

In America. Yes. Or in the world, I can't remember. Running Microsoft. The part that they never really publicized was running Microsoft software. So the one good idea. So let me come back to that. Actually, no, let me do that first.

The one good idea is we just want our stuff running on everything. We know that computers are the future, and so if Zuck only has one good idea, which is social, and you can make the argument that Bill Gates, all of the companies of the 80s that they slew to create the office suite, there were huge, multi-billion-dollar companies that had all of these other products, you know. Wait, wait, but, okay, to this, this original sort of inception idea, right? The thing that Bill Gates did that fucked everything up, but also created the Microsoft Empire, was applying copyright to software.

Okay, believable. In the early, earliest days of the homebring computer club. The greatest business bottle in history. Yes, precisely. So you have infinite abundance in software because you can copy it infinitely. He invented NFTs like in the 80s because he basically said every copy. No, he invented FTs. Yes.

Yeah, okay, even better. That's even better. And then he monetized it as though they were NFTs. Basically, every copy of Windows, which had no marginal cost besides the cost of the disc that it was printed on, could be monetized through subscription. Okay. So invented the entire business model. So that's why, to me, like Steve Jobs is the visionary who said,

this is how I want people to behave. And Bill Gates said, this is how I want to get paid. And it's also taste versus brute force. But as an entrepreneurial insight, the idea that hardware is the commodity, Bill Gates comes up in the era of IBM where it's like you buy a mainframe system from IBM and they just give you the software for free. The software is the differentiator. And because of the zero marginal cost thing, it is.

the margins that no business except for, I don't know, mining gold or some shit, had ever dreamed of in the history of humankind. There's no way mining oil is as profitable as... Yeah, probably not. Probably not. So, look, if you want to give a frigging historical insight award or something like that, I don't think you can argue that Bill Gates seeing that software was the... What's the word?

the pressure point or like the the funnel that all of modern technology has to go through, that's the greatest insight of our era. The only better business model than easily replicable software is easily replicable software distributed over the internet. It's just one more layer of business model nirvana. Back to Salesforce. Remove all distribution costs. That's an interesting point.

That's an interesting point because you could argue that as soon as the internet era comes, Gates is done. I mean, he wrote the book, you know, the road ahead. Is it the DOJ, David, or is it the fact that I know that he did. The only successful antitrust case in internet history? Yes, right. But at the same time, like, yeah, I don't know. Actually, I don't know. It may have been.

Go ahead. Well, I think this one truly is debatable. I think the one point of view is like, look, companies, many companies don't survive transition, platform transitions, and Google was coming anyway, and this would have happened anyway, and the DOJ didn't do a thing. On the other hand, like the DOJ case was about Internet Explorer, you know, like, they were right there. Well, and the case was specifically about platforms as a business model, which again,

is a checkbox in Bill Gates's column, which is that he created the concept of the modern platform play, right? Yeah. That you play in my ecosystem, that I don't necessarily have to charge you and nickel and dime you for everything that you do on my platform. Just having the platform is enough, although they wanted to do that. Of course, they would have done that if they could have. But so, again, I would make the argument that, you know, as Chris said, earlier. Zuck is playing the Gates playbook, essentially. I actually, I want to point something out that also just, you know,

in the way that history, you know, doesn't rhyme, but it echoes, no, whatever it is. It doesn't repeat what it rhymes. When I think about the way in which we think about Zuckerberg as, you know, an evil villain, Bill Gates was also an evil villain, you know, back in the day. And, you know, like granted, this is what my TEDx talk is about, but like the culture of founders, to me, is the most powerful thing that they produce and then generate because it creates progeny. And that progeny goes out in the world and they affect all the subsequent businesses that are started and founded and created and invested in after that point. So whatever large S, you know, the Microsoft millionaires and billionaires have to go that invest downstream, they will then use the lessons that that. they learn from that company and impart that to the next generation.

And if you think about the Gatesian playbook, the reason why they lost, I mean, I would say that they lost the DOJ case was because of the arrogance and the hubris and how awful Microsoft could be as a competitor. And they just like played everyone off of each other and they would like gut you. And you see it in Zuckerberg, but it's almost like he learned some of the lessons to soften it just enough to apologize and not be so obstinate so that he gets away with it and no one knows what to do with it. He can prevaricate and disseminate in ways that Gates never apparently had the skill to do.

That's what I mean. So like to like to Eric. Zuckerberg realized that the consequences could be that bad. He became more socially kind of savvy and sophisticated. And so I think when I evaluate each one of these like entrepreneurs, as we call them, I can't help but also evaluate them through that cultural lens. We spent a lot of time talking about Bezos in the culture that he propagated. So in thinking about these things and Steve Jobs too, like the interesting thing in the

matchup between Elon Musk and Steve Jobs is that they are both visionaries that see the future probably 30 years out and they're building towards it. And they're maniacally pushing down that path without necessarily bringing people along or creating a bunch of businesses, you know, for other people. And I think that's just different. And the culture that they create, this is the last thing I'll say, may be that they are required to sort of be at the helm of these ships in order for them to keep moving, whereas Zuckerberg and Gates and Bezos created cultures

that can operate without them at the helm. Ben. So, Chris, I think what you're saying is, thank you for coming to my TED Talk. Literally. I do have, I do have, I just got an unbelievable push notification that is like, couldn't be more perfect timing. Like it is literally just as we go into this final round, it's from the New York Times and it says, Breaking News, SpaceX sent into orbit the world's first space flight with no professional astronauts. Wow, there we go.

All right. Well, look, that's no better set way. It's perfect timing. Than to the finals. Kind of unbelievable. The finals are going to be. Steve Jobs versus Elon Musk. Now, I'm assuming you guys, since we didn't do this the last time, but did you guys look?

Do you want to guess who won and what the percentages are? Or have you already looked? I didn't look. We should guess. I haven't looked. I haven't looked. I'm going to guess regardless of what my actual opinion is, like, I'm going to just guess because of the hype cycle we're in right now, that it's Elon 65%. I'll go Elon even higher, 70 to 75%.

Wow. It feels like you guys are right, although I don't want it to be true. But I think it might be closer. Say it so. Like 55, 45, 45, Alon. So I don't know what to think about this, because this is the result I expected in kind of the numbers that I expected. And I wonder if this is generational. I wonder if we had a younger audience if it would be what you guys said.

But Steve Jobs won 68 to 32. Whoa. Wow. Wow. All right. Which means we need to talk about Elon first because he's the loser. All right. All right.

Now that's talking about his achievement from today. That is closer than a lot of the other results, 68% to 32%. It's the most votes that we got of any of the polls. And I, you know what? In Elon's semi-final round, he was losing and then there was a late surge for him. So I was kind of thinking the same thing would happen. I saw people on Twitter. Like, you know, right.

Did literally. asked the hashtag Twitter Army to vote and things like, or not Twitter, but Tesla Army. Yes. Okay. So we can talk about why Steve Jobs won later. But, okay, Elon Musk, clearly if there's any, he took the crown for modern. Yeah. If there's a modern living personification of an entrepreneur, it's Elon Musk.

He won the living entrepreneur World Cup. Yeah. You know, we could do an all-time, like, maybe that's the thing we should do is an all-time, like, we do against Rockefeller. We do against, you know, the frigging Medici's or something like that. I don't know. Anyway. But, okay, I don't even know where to begin, except for the fact that I'll say, if, and this is kind of like, this is a left field thing. One of the things that has always struck me about Elon Musk is that he, we know that he's had multiple foundings, multiple companies, multiple ideas. But you know how he had the PayPal thing or even before that he had the Zip 2 thing. Yep, yep. There was no question he makes this money and he's going to pour it into his next thing. But he pours all of it. Yeah.

Now, and then he takes out loans even deeper. Yeah. To finance it. If we're talking about the spirit of an, the dude never loses. That dude is never lost. But think about the spirit of an entrepreneur is. And I think the analogy that I may have made somewhere is,

is like, you know how in Hollywood there's this concept of like you're a director and you make a movie that becomes successful? And then you go to Hollywood and you say, here's what I really want to do. Elon was successful twice. a zip to and then PayPal. And then he's like, well, here's what I really want to do. I want to go to fucking Mars.

And I will take all of the money that I have and do that. Oh, you know what else I want to do? I want to make an electric car, which... And in this order, I think people forget that that SpaceX was founded first before Tesla. So if we're talking about the spirit of an entrepreneur that is like, I just want to fucking create my business. I've got this vision and I will burn it all down. I will go broke to make this vision happen.

Not once, not twice, however many fucking times at this point. We got a boring company. We got neural link. There's more. There's still more. I mean, that list is insane. I also think, by the way, if you want to make a pure economic argument, which I've been doing a lot on these couple shows,

I think that, sure, we've got a trillion-dollar company. We got two-trillion-dollar company at this point in history. A couple of them. I think SpaceX may be the first $10 trillion company. If they actually are the way that we get stuff up into space, we get to Mars, we colonize Mars, we bring Internet to half the planet, like this, the TAM for the stuff SpaceX is doing could be much larger than any of these big tech companies to date.

Yep. Face. Oh, boy. Infinite. I think to be like, you know, I was saving Brian when you were talking, the biggest thing that is impressive to me about Eli, well, where everything is impressive. But the biggest thing that is impressive is, you know,

we haven't nailed down a definition of entrepreneur. And I think that's right because there's lots of definitions of what an entrepreneur. Redmaker, we talked about this. Right. So one definition, I think, is, you know, related to. this sort of grit thing and like just refusing to lose. And like this is a man who refuses to lose, period. Even when his like the game he's playing is like the biggest in the world.

And literally that is in almost every single one of these companies. It is just that refusal to lose by him that has made these companies. Like it all comes down to that. You know, like I don't. I'm going to try to say this, like, how do I put this? So one of the things that I feel like I've observed, there's two observations that I would make about Alan Musk. One is that he is neurodivergent.

And it feels like, you know, and I would, I would, maybe Zuck is too, and Bill Gates seems like he may be. And there is a broad spectrum of the way in which neurology works in the way in which people think. and Alon to me feels like someone who thinks the way that the internet needs people to think. And that creates a strategic advantage over neurotypicals because his ability to focus and to clear out the noise and the clutter. And although he, you know, has dalliances in, you know, random whatever's, like when it comes down to the execution, it feels like he gets into a tunnel and just executes towards it.

And everything else is a distraction. And if you are a person, and I'm sure he has a healthy ego, et cetera, but if you are or have a normal, if you are neurotypical and have a normal ego, the things that you will do and get preoccupied with from a human culture perspective will hold you back. So I feel like that's why he's able to take off, you know, on these crazy adventures and doing insane things because he just doesn't give a shit, you know,

because his mind works differently. And to be someone who, you know, grew up reading comic books, and this is the other observation, you know, reading comic books and sci-fi, and then deciding, I want to do that, also means that he is sort of the winner of the revenge of the nerds contest. And so people who have always been the underdogs look to him and say, I've never belonged, and yet he is the king of the heap now. and there's hope for me yet. And so those things coming together give him an advantage that I think a lot of other entrepreneurs

lack because they're either unrelatable or they're not of the moment of the internet that Ailon seems to be. I think that's the best description of Elon as an entrepreneur that I've ever heard. I want to, because we're going to, and I know that we shouldn't take away from him because we're going to talk about jobs next. he's crazy and he makes crazy risks and he gets lucky. He hasn't had, I don't know, you could argue he has. He hasn't had what jobs had, which was failure.

Now, so could, now, listen, the definition. What about, the solar thing? That's not a failure like being kicked out of, well, and also he was kind of kicked out of PayPal. PayPal, but he also. Solar City. Solar City. Yeah, yeah, but SolarCit, isn't that part of Tesla now? He bought it.

Right, right, right, right. Okay, well, there was a scandal or there was something. Listen, there was. Steve Jobs was humiliated. Sure. He was kicked out of his company that he was the co-founder of, and he seemed to be a lost boy that had failed. The idea that, you know, it's better to be lucky than good, I agree, and I'm not arguing that he's not a genius.

What if he's just the luckiest? entrepreneur that ever existing. I really don't think so because space, four freaking rockets blew up before the fifth. And Tesla was like dead, dead, dead, in 2008. And then

the freaking 420 thing. Like that company, almost any other person at the wheel, that company died twice. But the fact that like the shame didn't take him out. Yeah. Exactly. He didn't pull a Jack Dorsey and become Zen, you know, and meditate.

He just kind of was like, whatever. You know what I mean? So I smoked some weed. So I did some weird shit. There's something about that, which either is hubris or his arrogance or his ego or is just neurodivergence that allows him to sort of get the wind from the internet and like keep going. Because mostly it doesn't matter in terms of the things that he's trying to achieve. We need to let we need to let Ben go because he needs to run real quick. So, Ben, if you want to do a final word, and then we promise we'll do you justice for

and wrapping this up for you. Oh. I mean, it's kind of funny that, like, Steve Jobs wins. Like, if you would ask me who's the greatest entrepreneur of all time when I was 12, I'd tell you Steve Jobs. So, like, why did we need to do all this? And why didn't have the last 20 years of being in this business? I mean, it's, it's, like, I had the guy's letters, thoughts on.

music and thoughts on flash, like, pinned up on my wall as a teenager. And, like, maybe I have a problem. But, like, his clarity of thought in the way that he wanted the world to be, and then his relentless efforts to make it so. And the taste and the passion in which he did it, I don't think has been matched by anyone else in history. Like, Elon Musk is as good of an entrepreneur and a visionary and maybe in more important ways, but no one will ever match Steve Jobs' taste. And I promise we're going to do you justice so you can dip out quietly while we continue this. But I think that that is the right way to seg into the winner of this World Cup of Entrepreneurs, voted by you, Steve Jobs. It's taste. I don't, it's tastes like an artist has taste.

and people have called him an artist over and over and over and over and over again. But I don't know, you know, if you think of, again, like going back to Rockefeller and things like that, there's not taste in being like, well, I'm going to just get all the oil, or I'm going to monopolize all the railroads or that. There's strategic thinking, there's aggressiveness, there's cutthroat willing to shove people. There's different in nothing that we've talked about, maybe around the edges for certain people, but the idea that you could have a vision, you can have a vision as an entrepreneur. This is an idea that I want to exploit. This is something that I want to build.

But this is something that I want to build because I want to see it realized in the world. That wasn't even enough, right? Because it was like, I want to see it and build it. it, but it also has to behave and perform in the way that I want it to. Yeah. And none of you motherfuckers believe me that it's possible, but I'm going to stay here on your ass until you know until I say yes. And the reason why I think that's so important, and there are so many reports about how Steve Jobs was so hard to work with and, you know, was abrasive and aggressive and all

these things. But clearly there was something in his, and he wasn't always right. I think it's important to recognize that, you know, unlike, you know, we were talking about with Alon where he just, you know, kind of just keeps winning. There were several things that Steve Jobs thought and turned out to be wrong. But there were some things that turned out to be right that were so right. And what I find is when we talk about taste, I think the thing that differentiates jobs from Bill Gates, who was his contemporary and is sort of sworn nemesis. I mean, not to give, everyone's going to cancel me now and like turn off, but like, was the fact that like Steve Jobs like did acid and was an integrated thinker.

I was going to bring that up. Yeah, I don't think you can talk about jobs and not talk about LSD. Okay, so let me explain why I think that's important was because the way in which psychedelics will operate on the way that you think is to a little. allow you to make connections that otherwise wouldn't make any sense. And then to allow you to entertain them in a complete, I mean, like when they say an open-minded way, it really is, you know, the aperture is blown straight open and you can suddenly see things from a different level than people who are stuck into or trapped by conventional thinking and knowledge. And what I think

Steve Jobs did very, very well in an era where this wasn't possible. And I guess I can relate to this to some degree, was he brought that sense of taste, of culture, of artistry, you know, into the software world where it was a very, again, straight, numerical, logical, reductive space. And I think he was able to go beyond that and to really feel through some sort of empathic wisdom, how other people would interpret or experience technology and worked very hard to reduce the feeling and the friction that technology imposes on its human subjects. And so that was the real thing that, like, the iPhone was the epitome of,

was removing the technology from the technology itself or the experience of technology as it had been required to feel. And that's why, literally, anybody who has these fingers, you know, can touch and manipulate a computing device. And so many things. Yes. clearly things have got a long way of course but integrated so many technologies to bring that to people and that's why I think when we talk about taste that's what we mean David I just roll

because you know we can all but but give you give your peace yeah I that's perfect then you should you should wrap up so totally you know it's funny Ben and I on Acquired every now and then with an episode, this theme will come up. Not enough as it should. So I think we need to highlight it more. And I'm really curious, Brian, what you think, given your perspective as a internet historian, I think like the 60s and the counterculture and California specifically in the 60s in the counterculture, like it was this great, you know, hope and dream of like a different world, right? and it failed in like almost all of its intended ways. But tech came out of it, right?

And like, and Steve Jobs is the link, right? And yeah, I think that's the, that's why I think you have to talk about acid if you're going to talk about Steve Jobs as the greatest entrepreneur, you know, of all, of all time. Or the World Cup winner, let's say. The World Cup winner. The World Cup winner. because, yeah, the whole, like, you know, everything, Elon, you know, that we've all sung his praises and everybody else on this list. Jobs, I think, was the first one to say, you know, Chris, as you said, like, this thing that everybody else would have said was, like, unreality can be reality.

And, like, and that's the legacy of the counterculture that made this all happen. That's my piece. Yeah. I said in the book that Silicon Valley's culture is a combination of sort of MIT libertarianism with, you know, hippie countercultural stuff. Steve Jobs' idol, like a lot of people his age, was John Lennon. He did more to realize the vision that he and John Lennon believed in than John Lennon did, I would say. I'm going to not because I believe this, but because I feel like I just want to push back a little bit.

Okay. What if, let me throw the concept out there. Steve Jobs was a bad businessman or entrepreneur in the sense that he did fail his first time out. in the sense that Apple almost died, and it was largely because of the decisions he made. He wanted that lockdown thing. He wanted, you know, you could only do the things that he wanted you to do with his machine. And so we said about Elon, maybe he's the luckiest, but what happened to, I would posit, playing devil's advocate, what happened to Steve Jobs is he got lucky. because in the PC era, the business model that Bill Gates had was superior to the business model that Steve Jobs wanted.

He got a second bite of the Apple. Sorry. And that second time, he got lucky because his vision actually made more sense when the iPhone came around than when he was competing against Bill Gates and the PC clones and things like that. Chris, you look skeptical. What do you think about that? Well, I think that you've brought up a really important point, but it sort of builds on the things we've been talking about. And the point that I would make is that Bill Gates was perfectly suited to create a business model for the business world because he was fighting against the international business machines company. And I think that Steve Jobs, through whatever vision he had on his vision quests or whatever, was more interested in bringing computers to everybody.

And that is why the iPhone was preceded by the iPod, which was an entertainment device and was more accessible to millions of people. And there was always the presence of, you know, fun of things that, you know, people enjoyed, right? Was music, you know, YouTube albums. But personal computing, Chris. Well, there was a PC industry for 20 years. Personal computing didn't start until the iPhone came out. Until you had a computer in your pocket. Yes.

Personal computing. Steve Jobs understood personal computing more than anyone else. He put the personal in personal computing. I agree with you. Even though I understand the haters are going to come on and say, oh, well, personal computing was in reference to time sharing on, you know, shared machines. But like, we're talking about personal in the, this device represents and reflects me and is an extension of me.

And Steve Jobs, I, you know, I don't know. I never talked to him or whatever, but like could imagine extending yourself cyborgenically into these products. And that is what the iPhone became because it humanized technology in a way that no one else had really done or had been willing to achieve. And so the thing that I want to say, when we come back to this question of what is an entrepreneur, it seems to me that what unifies a lot of these people is that they defy fear that otherwise would cause other people to flee the same.

scene, to leave, to abandon their ideas, to abandon their hopes and dreams, it's not enough to be a visionary. It's critical to be, to have the vision and also to stand in the face of fear and to continue to go forward. You know, if you think back to like what Steve Jobs did with next, and he kept trying, even though he was wrong, so many times. And that over time, by just throwing himself into a wall, eventually he had to have learned some lesson that, said, you know, maybe I'm going about this in a slightly wrong way. And when he finally came back to Apple, he was matured. He wasn't as, as I understand it, abrasive. And so it just, it feels like persevering in the face of fear is what really identifies or unites entrepreneurs.

I love that. I think that's, I think that's great. The only small thing I'd add is, you know, the next, you know, it's funny, right? Like, you know, maybe he was wrong at Apple. And then Next was not hugely successful as a company, but it's what Next developed that's in every single one of our iPhones now. Yep. From world religions and from Joseph Campbell that sometimes you have to go out into the wilderness. Yes. You get your redemption arc. I don't know that, gentlemen, that we have solved the question of what an entrepreneur actually is.

I feel good that Steve Jobs won this contest. I'm surprised that you guys thought Elon would have won it, but we don't have time to get into that now. I do want to say this. I want to say number one. David, your podcast is amazing. Ben and you do the Acquired Podcast. I want to just say, if you've never listened to it, you guys do such smart work. Oh, my God.

Thank you. So good. I mean, literal MBA level stuff and beyond. So search your podcast app for Acquired. Is it Acquired podcast or just acquired? Just acquired. You'll find it with Acquired. Yeah, just acquired.

Thank you both of you and Ben for coming on to do this. Thank you, Chris, for doing this again. Yeah, it's fun. And I got to say this. I feel like I came to you guys with a wild, crazy idea, and you guys kind of went along with me because you like me. Jesus Christ, man, I haven't had fun like this in a little while. This was great.

So thank you, thank you for doing this. We do like you and we think this is a great idea. Okay. Great. Well, next time I come at you with a crazy idea, it might not be this good. All right. Thanks, everybody. And hey, Steve, wherever you are at, you won the World Cup.

Congratulations. Yeah. Later.