(Bonus) World Cup Of Entrepreneurs Part 2

Welcome back to another super special episode of the Tech Meme Ride Home Experience. We're going to do part two of our World Cup of Entrepreneurs, I don't know, contest, extravaganza, hashtag World Cup of Entrepreneurs. These were all voted on by you, the listeners of the Tech Named Ride Home podcast. So that everyone knows people's voices, let me reintroduce my usual guest or co-host.

Chris Messina, inventor of the hashtag. The West Coast Business Development at Republic, right? Is that your name? Head of Business Development at Republic. Head muckety-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 show, so this is good. I'm going to really bask in this now. I'm David Resenthal. I am one half of the Acquired Duo. I'm an angel investor. based in San Francisco. and uh Brian, I was thinking earlier, since you said contest or battle, I think Thunderdome is 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 Tech Meme 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. you know, our recreational lives. Maybe I would make the argument that Reed Hastings 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. 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 Gazer 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. Only recently has Amazon bought MGM. The fact that 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. 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. Right. Shut up. There's such a good story. It was years ago that we did the two part on Netflix Unacquired, but...

If I'm remembering right, there's such a good... Blockbuster really should have won. They had the right strategy. It was like a weird shareholder thing. They were about to pull the trigger on putting Netflix in their grave and then shareholder problems.

I will say that in Reed Hastings' defense, one of the things that's so important about the Netflix story is the pivot from being a DVD-focused company to one that was digital and streaming. Yeah, thank you. Yes, exactly. It's sort of like, what was the one from last year that fizzled out also that had like $7 billion in funding? Quibi. Thank you. A Quickster or Quibi? Similar. Let me just make my point down. Yeah, yeah. 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 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. You did Silverlight when they first launched it. Oh, God, Silverlight. Yes, Silverlight. Microsoft DRM shit. 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, I guess I say this also because You know when people ask me about the hashtag i have a similar feeling where it's like you know had you know 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 win brian 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 is 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 multi-billion 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 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. They kicked off this new golden era of television that we live in where the power has 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 newsfeed, 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 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, as 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. Yeah. 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 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. It's actually quite interesting. there are about 200 million prime members and about 200 million netflix subscribers wow it's interesting to note so that's crazy that prime video hasn't actually taken a cut of netflix wow okay but here's the thing Like I pay Netflix $216 per year before sales tax.

I pay Amazon a godly crap ton of money every year. You know what? Can I make one more analogy? Because this was the matchup of Bezos versus Hastings, so Amazon versus Netflix. um if if you want to give credit to bezos for this idea of uh 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

Which was right. Which was right. And did Hastings 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. I know 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, 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. Well, you also, you asked Brian, Was it the plan from the very beginning for Netflix to become what it is today? I don't know. I don't remember enough to answer that exactly, but I will say... in a sort of feather and reads entrepreneurial hat.

Their outcome... where they've gotten to is wholly path dependent. Like they could not have done streaming if they had not done DVD and they could not have done original content if they hadn't done streaming and DVD before it all stacked up. And it goes back to 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...

The 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 like

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 the ownership of... uh ideas but i thought that was a great point too that whether 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. The fact that like... elon jack on his own platform is 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, if you don't know, if you know what I'm saying, but guess how many followers do you think Jack has? On Twitter. 15 million. Yeah, I was going to say 30 million. 5.6 Oh, what?

Wow. And nothing. I was going to say Elon probably has like 35. What, did he get booted off a who to follow list? Elon has 59.9 million. By the time this episode comes out, he will have 60 million. well listen here's 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

The whole 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? Not Instagram, though. Who's the most followed person on Twitter right now? Quick.

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I don't know. Somebody Google that one. Maybe Elon. No, it's probably like Ronaldo or somebody like that. It's Obama. What? No. It's like every time I see someone, they're like, yeah. Obama's rocking 130 million. Whoa! That's more than LeBron has on Instagram, which is 98 million. Wow.

Okay, somebody. Justin Bieber has $114 million. This is wildly going on the rails. Because we need to do justice to Jack Dorsey. And I'm going to 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. And he's up against the only other guy on this list who's currently CEO of two companies. Right. And I said Stripe, 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 lined piece of paper. But that's 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. And look, you know, if we talk about... In both cases, though, right? You know what, Chris, you should take this. Go. I mean, but...

The parallels to me, again, a lot of what we're talking about are these, I think, Ben, you might have 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 behemoth.

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. We had 140 characters and I had to make use of that to solve that problem. Additionally, Square came out of 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 like you can do that like what so i feel like 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

Were you buzzed with Jack and all the Twitter folks in the early days? I was in their social circles. I could go into Twitter's headquarters. I was more friends with 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 an 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 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 you know 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 like a random

appendage that's built into the apparatus of reality that I can build upon. 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 uh once you're lucky twice you're good and like For Jack, obviously how painful it must be getting ousted when something that was really kind of your idea...

did blow up. Nothing grew as fast ever as Twitter did. It was just this unbelievable growth story. And being ousted and saying, you know what? I'm going to gather all the chutzpah I can and I have another really good idea. And of course, it's not just that he had an idea. He went to St. Louis and he knew Jim and they sort of started this. But 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. Yep.

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 explain 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 specific episode on the Cash App?

No, just a square and it was before the rise of the cash app. Okay, because 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, since this is like, you know, Jack's last kind of, you know, I suppose, I do think you know just as um

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 guru sort of sense you know I mean not only does he sort of like dress the part and you know has the beard etc 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 ferris 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

and meditates and sleeps and does cold plunges and all these weird esoteric things. I just feel like that's also worth thinking about because the rest of the folks who are kind of on this list... little bit more straight in the sort of you know normal normally kind of uh in a way of being jack moved 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, even Twitter, if we're talking about Snapchat coming back,

Snap and Twitter have been the comeback stories in terms of stocks and social media companies over the last couple of years. So there's that as well, 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 Trounce them. Now, this wasn't trouncing. We should have tipped the scales on that one.

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 this matchup is Patrick Collison versus Bill Gates, so I would have been glad to have seen him. come up in this one. Right, right, right. I would have loved to have seen Oprah versus Bill Gates. But yeah, 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 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 platform than Square.

than just to riff off the previous conversation. The amount of commerce that can happen digitally on the internet because Stripe exists is like 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 Braintree, which was leaps and bounds better than Authorize.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 and just five lines of code. Now you can accept credit card and 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 the amount of different customers they serve. all with a pretty simple, elegant way of understanding what each of these products is, except maybe Stripe Treasury, which I'm still trying to wrap my head around. It's amazing. 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 reverence. 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, you know, we can get into the idea of, you know, APIs all the way down and things like that.

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 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 like the fact that the internet didn't come with payments built in that 402 was never specified kind of left this wide gaping hole and you know 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 I can say this because of the work that I did on OAuth, 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 it in that paradigm for the medium and the moment that we live in. And that, I think, is what sort of separates Collison from, you know, the ones that came before. Chris, would you buy Stripe stock if it were public today at $100 billion market cap?

I probably would. I mean, because honestly And 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 All the stuff that's 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... 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 it. 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 at like right around the same time.

The best thing is, 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 is. Bitcoin is 8x higher value right now. 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 than the other, 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 the enabling other things the platforms the apis and all that stuff like 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 But Like it's it's happening right now for you know a friggin pizza place around the corner So like these things do not seem like they're incompatible I mean, like, if it doesn't already support crypto, Ken. All right, all right, all right. Brian McCullough hates crypto. Go on. I think he hated Bitcoin. Is that the... Yeah.

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So 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 devil's advocate. 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 that the point that you guys made before where they kind of like one good idea and then they just kind of like built it out um 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 they kind of

They don't really have a world-changing, world-building play. Elon wants to go to Mars. Bill Gates took over the world with his software and is now curing malaria. Larry and Sergey wants to... 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 guess 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,

So this raises a question, right? And I think this is one that I've been trying to figure out in this mix, which is, the degree to which as a 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, you know, in the arena. Yeah.

are willing to go there, even if it's uncomfortable. I feel like, you know, Elon will go to like the galas 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, with humans that just don't understand like his, his master plan and vision. And I feel like Larry and Sergey are kind of like, like they did like the, the Ellison thing, they bought their Island and now they're going to like live there. Cause you know, screw humans, you know, Billionaire stuff. And Elon doesn't really do billionaire stuff. He lives in a shack. He lives in a two-bedroom little...

2000 top square foot house. That's what I mean. 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. 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, that's where I'm kind of like, just a hundred percent.

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 COVID. 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. That's right. That's right. Let me say 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 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. I think that's what I'm saying. When it comes to the grit, of being an entrepreneur in the business world. Okay. They would have preferred to stay. They seem like the least gritty people on this list. Yeah. Let me also clarify, that isn't to diminish their achievements. That isn't to say that they're less amazing. 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 leave the arena, you know, and they'd like walk out and they'd be like, too much blood. Can I do real quick two last little feathers for them? YouTube and Android. Huge, huge fan. 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 gotta 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... Oh, 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 um they're not as bloodthirsty They also did have the insight, or at least that was in their nature, that 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 for that. yeah i think like having having worked there and worked on the google campus and

there was a lot more playfulness and a lot more generosity for ideas. But, you know, you did, there was a kind of credentialing and a very kind of... quasi arrogant elitist, you know, you have to be super smart. Did you feel like you were like, like literally like, wow, this is like the assemblage of the best and brightest people on the planet right now. Like, um, the way that I would.

The way that I would evaluate it is on a couple of different 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+, 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 they were just aloof. You know, I think about Google Glass.

you know versus like the product that you know facebook just launched um you know with their spectacles like 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. And that hubris and arrogance was a type of deficiency and... there was like defensiveness around it that i think googlers not all i don't want to over generalize but were 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.

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 bracket. 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

quick proposal here. So the email that you sent us has so much of question marks. Right, because these votes hadn't happened yet. So do you want to guess? Or should we call our picks definitive and argue and come to a consensus on this call? Okay. All right. I like the idea of guessing, and then we want to hear what the public said. Guess who you think won. 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 37.7. 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. Okay, alright, 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 Andreessen 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? No. And then we can go into all of the other things, spending money, being willing to lose money forever and ever to build the business. 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. I mean I don't know even where to go.

with this not to mention just like the supply chain innovation you know and like prime and like the membership thing and prime warehousing fulfillment centers I feel like all of the best business quotes are Jeff Bezos quotes like anytime 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 of platforms, that it wasn't until we had UPS and the internet that you could build Amazon, that he took advantage of the giants that came before him. He has this unbelievable conciseness to be able to communicate business concepts that I think inspire generations. And I'll say... So this is going to sound trite, but I actually really believe it, and I think it's true in Bezos' case.

All of the amazing stuff that, uh... he and Amazon created, I think the most amazing thing is the culture at Amazon. And before Amazon, just like we were saying about Google. How would you sort of describe it, right? Given my description of Google, how would you talk about Amazon? It's so different, right? They are 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, you know, maybe Ford was, like, the first, like, you know, industrial, like, you know, manufacturing line, assembly line company. Amazon is the first decentralized company. Like, they really mean the Two Pizza team. 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. And we're starting to see it disseminate out into other companies like it, but it's just going to continue. It's a wholly different way of conceiving. what the organization... is and how it operates and how innovation happens and what we do here. And again, lots of people don't like it. It has its challenges.

There's some things that are great for the world, there's some things that are bad for the world with it, but it was wholly new. And I think that's, 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 think the fact that Jeff Bezos started in the financial world.

Right, he started, and Brian, you can probably speak to this better than I can, but started in... 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% 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 outside of a Petri dish, right?

He was the Sam Bankman parade 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 you know lots of people saw the wave coming and again he's the one that wrote it all the way so yeah

It's such a good point. 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-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. Exactly. Apple and Microsoft are from the 70s. Facebook and Google are post-bubble. Yahoo's not around. I actually think like 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. The fact that he's Tesla's chief engineer. They're having the Model 3 shortages and he's sleeping at the factory. It's just a very different... type of person and mentality then 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 he was 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. Yeah, it's funny. 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... Hashtag proud investor. 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 50 X 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 X it is, but whatever. I'm going to do one thing to close out with, with Bezos.

because this might lead us into eventually the Steve jobs conversation. Um, but to use, uh, 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 um 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? The book was written by Mike Moritz too, which makes it worth reading in and of itself. Building culture, building a process, a way of doing business.

You know, 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 last year. Um, I wonder to what degree, if we did this five years, 10 years from now, Um, would we look differently at Amazon if the transition, like, 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, just to add to this, The fact that they managed the transition as well as they did this year, where it really felt like Bezos was this sort of... asymptotic figure, you know, I had, you know, the SS 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 TV and all these other things, right? And it was sort of just building out generations of the iPhone.

For Amazon, what is the next set of acts? Bezos left the right set of playbooks or the right set of roadmap. 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, that's what I think. That's kind of what I meant about that culture. the way it works that it's not like some genius it's not like bezos hands down what did you look at the fire phone right like it's

The way that the organization works is it's like complexity theory. It's just built on 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 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 about, 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.

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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. um you know it helps god and kill emilio yes that's right okay right i forgot about the first time 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.

Okay, I'm transitioning to the second semifinal. which is perhaps the most classic matchup you could have in a tournament like this. Class of Titans. This is what the punters in the stands paid their tickets for. It is... Steve Jobs versus Bill Gates. I mean... And it's taste versus iron. Okay, you know what? We're gonna have... We're not going to talk about Steve Jobs right now because Steve Jobs beat Bill Gates 71.3%, 28.7%.

Right, 71.3% to 28.7%. So one of, in the middle of the road in terms 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 a better he's better at creating products that people love creating products is a far better business business 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?

Now that's a good question. 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 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 I guess are willing to totally Batman by the way oh yeah 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, but 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. Zuck wanted to be Gates. Right. That was what I meant.

so 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 because everything that was going to be on this pristine, perfect device had to sort of come from the Godhead directly, you know, and.

Talking too much about Steve Jobs. This is... I thought I was talking about Bill Gates. Bill Gates, right. I was comparing and contrasting these two archetypes, where one is the 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 or join the computing revolution, provided again all rows led back to Windows. That was the Bill Gates playbook. And then Zuck saw that and did 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. 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 in America, or in the world, I can't remember. And 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. To this original sort of inception idea, the thing that Bill Gates did that fucked everything up but also created the Microsoft empire was applying copyright to software. Okay. In the early, earliest days, I'm discovering the greatest business model 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... No, he invented FTs. Yes.

yeah okay even better that's even better and then he monetized it as though they were nfts yes basically every copy of windows which which had no marginal cost besides the cost of the disc that it was printed on could be monetized through subscription 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 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 to then remove all distribution costs.

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. The road ahead. Is it the DOJ, David, or is it the fact that... I know that he's 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. Go ahead. Well, I think this one truly is debatable. I think the one point of view is like... look, many companies don't survive 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, the DOJ case was about Internet Explorer.

They were right there. Well, and the case was specifically about platforms as a business model, which again is a checkbox in Bill Gates' column, which is that he created the concept of the modern platform client, right? Yep. 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, then 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. Actually, I want to point something out that also, in the way that... History doesn't rhyme, but it echoes whatever it is. 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 back in the day.

and you know i 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 and invest downstream they will then use the lessons 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 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. Zuckerberg didn't realize that the consequences could be that bad. He became more socially savvy and sophisticated. And so I think when I evaluate each one of these 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 and the culture that he propagated.

In thinking about these things, and Steve Jobs too, the interesting thing and 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 for other people.

and i think that's just different in the culture that they create this is the last thing i'll say maybe 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 could operate without them at the helm. So Chris, I think what you're saying is thank you for coming to my TED Talk.

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. Alright, well, look, that's no better Saturday 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'm going to guess, regardless of what my actual opinion is, 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. I like it.

It feels like you guys are right, although I don't want it to be true. I think it might be closer. Say it, I'm so... Like 55, 45, Elon. 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. Wow. Wow. All right. Which means we need to talk about Elon first.

Because he's the loser. Okay. All right. All right. Now that's... We're 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 and 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. They literally asked the hashtag Twitter army to vote and things like that. Or not Twitter, but Tesla army.

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 life. Yeah. If there's a modern living... Yeah. Personification of an entrepreneur, it's Elon Musk. He won the living.

Entrepreneur. Yeah. you know what 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 freaking medicis or something like that um but okay uh i don't 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. She... we know that he's had multiple foundings multiple companies multiple ideas but you know how um He had the PayPal thing, or even before that, he had the Zip2 thing. 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.

And then he takes out loans even deeper to finance it. If we're talking about the spirit of an entrepreneur... The dude never loses. That dude is never lost. But think about the spirit of an entrepreneur as... And I think the analogy that I may have made somewhere is that, 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, Zip2 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. And in this order, I think people forget that, that SpaceX was founded first.

So if we're talking about the spirit of an entrepreneur that is like, I just want to fucking create, man. 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 times at this point We got Boring Company, we got Neuralink, 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 of shows, I think that, sure, we've got a trillion dollar company. We've got a 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, like, 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.

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Oh, boy. Infinite. I think, to me, like, you know, Sam and Brian, when you were talking, the biggest thing that is impressive to me about Elon Musk where everything is impressive but the biggest thing that is impressive is uh 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 is. We talked about this. One definition, I think, is related to this sort of grit thing.

And just refusing to lose. And this is a man who refuses to lose. Period. Even when the game he's playing is 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?

One of the things that I feel like I've observed, there's two observations that I would make about Elon Musk. One is that he is neurodivergent. And it feels like, and 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 and the way in which people think. And Elon 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 has dalliances in random whatevers, 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 distraction and if you are a person and i don't i'm sure he has a healthy ego etc 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 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, 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 Elon seems to be. I think that's the.

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. You know, 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 uh paypal but uh but he also solar city solar city yeah yeah yeah but solar city isn't that part of uh tesla he bought it yeah right right right okay well there was a scandal or there was something 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? I really don't think so because Four frickin' rockets blew up before the fifth. Like, and Tesla was like dead, dead, dead, dead in 2008. And then the fricking 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 like whatever you know what i mean like so i smoked some weed so i did some weird you know like there's something about that which either is hubris or is 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 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 wrapping this up for you. Oh. mean it's it's kind of funny that like

Steve Jobs wins. Like if you had asked 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 did not last 20 years of being in this business? I mean.

it's uh 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 the, 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, the taste and the. Passion and 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 tastes like an artist has taste. And people have called him an artist over and over and over and over again. But I don't know... You know, if you think of, again, like going back to like 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 whatever. There's strategic thinking. you know, um, aggressiveness, there's a cutthroat willing to ship. There's different.

And 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 wanna exploit. This is something that I wanna build. But this is something that I wanna build because I want to see it realized in the world.

that wasn't that wasn't even enough right because it was like i want to see it and build it but it also has to behave and perform the way i 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 was abrasive and aggressive and all these things. 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 Elon, 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 is his contemporary and his 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. I don't think you can talk about jobs and not talk about LSD.

and 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 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 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 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 i think 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

You see a stylus, we blew it. Yes. Well, clearly things have gone 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, just roll. Because, you know, we can all... But give your piece. Yeah, and then you should wrap up. So...

Totally agree. 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 an internet historian. I think like the... 60s and the counterculture and California specifically in the 60s and the counterculture like it was this great you know hope and dream of like a different world right and it failed in almost all of its intended ways. But tech came out of it, right? And Steve Jobs is the link, right? And yeah, I think that's why I think you have to talk about acid if you're going to talk about Steve Jobs as the greatest entrepreneur of all.

of all time, or the World Cup winner. 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, Chris, as you said, this... thing that everybody else would have said was unreality can be reality. 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 is 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 gonna, 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 this concept out there. um 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. 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, 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?

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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 what you know youtube albums but personal computing chris 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. 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 don't know, I never talked to him or whatever, but I could imagine

Extending yourself cyber organically 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 scene, to leave, to abandon their ideas, to abandon their hopes and dreams. It's not enough to be a visionary.

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 feels like persevering in the face of fear is what really identifies or unites entrepreneurs. I love that. I think that's great.

The only small thing I'd add is, you know, 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. Did you get your redemption arc? I don't know, 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 the search for your podcast app for acquired.

Is it Acquired Podcast or Just Acquired? Just Acquired. You'll find it with Acquired. Just Acquired. Thank you, both of you and Ben, for coming on to do this. Thank you, Chris, for doing this again. 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 while. This was great. So 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're at. You won the World Cup. Congratulations. Yeah. Later.

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