(Bonus) World Cup Of Entrepreneurs Part 2

Summary

Techmeme Ride Home: (Bonus) World Cup Of Entrepreneurs Part 2 – Detailed Summary

Release Date: May 18, 2025
Host: Brian McCullough
Duration: Approximately 105 minutes

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Introduction

In this special bonus episode of Techmeme Ride Home, host Brian McCullough, alongside guests Chris Messina, Ben Gilbert, and David Rosenthal, delve into the highly anticipated World Cup of Entrepreneurs. This contest extravaganza, voted on by the podcast's dedicated listeners, aims to crown the most influential entrepreneur of our time through a series of head-to-head matchups. The episode meticulously analyzes each round, offering insightful discussions on the visions, impacts, and legacies of some of Silicon Valley's most prominent figures.

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Quarterfinals

1. Jeff Bezos (Amazon) vs. Reed Hastings (Netflix)

Result: Jeff Bezos Wins – 77.9% to 22.1%

Discussion Highlights:

• Impact on Economy vs. Lifestyle: Jeff Bezos is celebrated for revolutionizing e-commerce and logistics through Amazon, fundamentally altering how goods are bought and sold globally. In contrast, Reed Hastings is recognized for transforming media consumption with Netflix, changing how people entertain themselves.

• Cultural Disruption: Bezos's Amazon has not only reshaped retail but also introduced AWS, which powers countless startups and enterprises. Hastings’s pivot from DVD rentals to streaming and original content creation marked a significant shift in digital media.

• Key Conversations:

  • Chris Messina [03:29]: "Jeff Bezos has changed the way we buy things and have a bigger impact on the economy, while Reed Hastings has changed our recreational lives."
  • Ben Gilbert [06:04]: "Reed was right in pivoting to streaming, similar to how Netflix navigated technological and consumer challenges."

• Conclusion: Despite Hastings's significant cultural impact, Bezos's broad economic influence and innovative business models secured his victory in this matchup.

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2. Jack Dorsey (Twitter, Square, CashApp) vs. Elon Musk (Tesla, SpaceX, Neuralink)

Result: Elon Musk Wins – 73.2% to 26.8%

Discussion Highlights:

• Entrepreneurial Scope: Jack Dorsey is lauded for his contributions to social media and fintech with Twitter and Square (now Block). However, Elon Musk's ventures span electric vehicles, space exploration, neural technology, and more, showcasing a wider range of groundbreaking initiatives.

• Cultural and Strategic Influence: Dorsey's innovations with Square and CashApp have significantly impacted digital payments and financial technology. Musk, on the other hand, is viewed as a modern industrialist pushing the boundaries of technology and human potential.

• Key Conversations:

  • David Rosenthal [12:20]: "Reed's entrepreneurial journey was largely path-dependent, stacked by consumer demand and legal frameworks."
  • Chris Messina [30:39]: "Elon’s relentless pursuit of his visions, like colonizing Mars and advancing electric cars, demonstrates unparalleled entrepreneurial spirit."

• Conclusion: Elon Musk's diverse and audacious ventures, combined with his unwavering determination, resonated more with listeners, leading to his decisive win over Jack Dorsey.

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Semifinals

1. Jeff Bezos vs. Elon Musk

Result: Elon Musk Wins – 62.3% to 37.7%

Discussion Highlights:

• Innovation and Risk-Taking: While Bezos established Amazon as a behemoth in e-commerce and cloud computing, Musk's ventures like SpaceX and Tesla represent bold leaps into uncharted territories.

• Cultural Impact and Public Perception: Musk's visibility and willingness to engage in high-stakes projects have garnered him a passionate following, whereas Bezos is often seen as more reserved despite his monumental contributions.

• Key Conversations:

  • Ben Gilbert [33:10]: "SpaceX’s potential for a $10 trillion market cap showcases Musk’s forward-thinking initiatives."
  • Chris Messina [80:04]: "Elon embodies the spirit of an entrepreneur who pours everything into his next big vision, defying conventional limits."

• Conclusion: Musk's multifaceted approach to entrepreneurship and his ability to capture the public's imagination with ambitious projects secured his victory over Bezos.

2. Larry Page & Sergey Brin (Google) vs. Steve Jobs (Apple)

Result: Steve Jobs Wins – 76.7% to 23.3%

Discussion Highlights:

• Vision vs. Execution: Larry Page and Sergey Brin are credited with building Google into a centralized powerhouse that organizes global information. However, Steve Jobs is revered for his unparalleled ability to merge technology with design, creating products that resonate deeply with consumers.

• Cultural and Organizational Influences: Google's decentralized, innovation-driven culture contrasts with Jobs's focus on creating aesthetically pleasing and user-friendly products. Jobs's commitment to "taste" and "artistry" in technology is highlighted as a key differentiator.

• Key Conversations:

  • Ben Gilbert [38:19]: "Larry and Sergey, while not the quintessential entrepreneurs, laid the foundation for Google's dominance through strategic acquisitions like YouTube and Android."
  • Chris Messina [94:17]: "Steve Jobs integrated his visionary ideas with a relentless drive to humanize technology, resulting in iconic products like the iPhone."

• Conclusion: Steve Jobs's holistic approach to product development and his ability to infuse technology with artistic vision earned him the win over Google's co-founders.

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Finals: Steve Jobs vs. Elon Musk

Result: Steve Jobs Wins – 68% to 32%

Discussion Highlights:

• Taste and Vision: Steve Jobs is celebrated for his exceptional taste and ability to create products that are not only functional but also aesthetically pleasing and culturally impactful. His vision transformed Apple into a leader in personal computing and consumer electronics.

• Resilience and Leadership: Jobs's journey, including his ousting from Apple and subsequent return, exemplifies resilience. His ability to persevere through setbacks and refine his vision was a crucial factor in his victory over Musk.

• Cultural Legacy: Jobs's influence extends beyond products; he shaped corporate culture at Apple to emphasize design, user experience, and innovation. His advocacy for integrated hardware and software solutions set new industry standards.

• Key Conversations:

  • Ben Gilbert [101:10]: "Steve Jobs did acid and integrated thinking, allowing him to make unique connections that transformed consumer technology."
  • David Rosenthal [95:42]: "Steve Jobs was the link between the counterculture of the 60s and the technological innovations that followed, embodying the spirit of visionary entrepreneurs."

• Conclusion: Despite Elon Musk's impressive portfolio and relentless pursuit of futuristic ventures, Steve Jobs's profound impact on technology, design, and consumer habits ultimately resonated more with listeners, earning him the title of the World Cup of Entrepreneurs Champion.

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Conclusion

The World Cup of Entrepreneurs concluded with Steve Jobs emerging as the definitive champion, celebrated for his unparalleled taste, visionary product design, and resilient leadership. While Elon Musk showcased a broad and ambitious entrepreneurial spirit, and other figures like Jeff Bezos and Reed Hastings made significant contributions to their respective fields, Jobs's holistic approach to integrating technology with human-centric design secured his top position. The episode underscored the multifaceted nature of entrepreneurship, highlighting how vision, resilience, and cultural impact play pivotal roles in defining entrepreneurial greatness.

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Notable Quotes

• Chris Messina [03:29]: "Jeff Bezos has changed the way we buy things and have a bigger impact on the economy, while Reed Hastings has changed our recreational lives."

• Ben Gilbert [06:04]: "Reed was right in pivoting to streaming, similar to how Netflix navigated technological and consumer challenges."

• Chris Messina [30:39]: "Elon’s relentless pursuit of his visions, like colonizing Mars and advancing electric cars, demonstrates unparalleled entrepreneurial spirit."

• Ben Gilbert [38:19]: "Larry and Sergey, while not the quintessential entrepreneurs, laid the foundation for Google's dominance through strategic acquisitions like YouTube and Android."

• Ben Gilbert [101:10]: "Steve Jobs did acid and integrated thinking, allowing him to make unique connections that transformed consumer technology."

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Final Thoughts

This episode of Techmeme Ride Home offers a comprehensive analysis of some of the most influential entrepreneurs in recent history. By dissecting each matchup with depth and engaging discussions, listeners gain valuable insights into what defines entrepreneurial success and legacy. The victory of Steve Jobs serves as a testament to the enduring power of vision, design, and unwavering commitment to excellence in shaping the technological landscape.

Transcript

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[Chris Messina]

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 what 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 reintrod my usual guest or no co host, Chris Messina, inventor of the hat alone, the west coast business development at Republic. Right.

[Ben Gilbert]

Is that your head of business development at Republic?

[Chris Messina]

Head muckety muck Republic. And we're joined by the co hosts of the acquired podcast. I went with Ben first last time. So, David, introduce yourself.

[David Rosenthal]

Oh, out of order. Ben always introduces himself first on our shows. This is good. I want 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.

[Brian]

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.

[Chris Messina]

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.

[Ben Gilbert]

Hastings invented Netflix and chill.

[Chris Messina]

Right? Like he has more of an impact on how we live our lives every day maybe than Jeff Bezos. Discuss.

[David Rosenthal]

Not if Jeff Bezos has anything to say about it.

[Ben Gilbert]

But like Reed Hastings, business is probably built upon a business. One of the businesses that Jeff Bezos built feels like one of the, 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. 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.

[Chris Messina]

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, that until Netflix tech actually was successful at media. Right. Now you can argue that Steve Jobs via the itunes store.

[David Rosenthal]

And Pixar too.

[Chris Messina]

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.

[Ben Gilbert]

Where was Blockbuster based?

[David Rosenthal]

Texas.

[Chris Messina]

Right. Houston.

[Brian]

In the past.

[Chris Messina]

Yeah.

[Ben Gilbert]

Right.

[David Rosenthal]

There's such a good stuff always years ago that we did the two part on Netflix unacquired. But if I'm remembering right, there's such a good, like Blockbuster really should have.

[Brian]

Won and they had the right strategy. Yeah, it was like a weird shareholder thing. Like they had, they were about to pull the trigger on like putting Netflix in their grave and then shareholder problems.

[Ben Gilbert]

You know, I will say that in Reed Hastings defense, you know, 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 was the one from last year that, you know, fizzled out also that had like $7 billion in funding. Quibi, Quibi, thank you. A Qwikster A quibi similar. But actually, David, let me just make my point though.

[Chris Messina]

Yeah, yeah.

[Ben Gilbert]

Like, because this was also a bet the farm moment. I don't know if you can say whether the rollout was botched or whether 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 to me this is the product learning and the learning about people is that that was so much more present for them. Going to a Blockbuster and getting people VHS or DVDs was so important. Getting the DVD in the mail was a ritual and it was understood. And streaming. The performance sucked. Your computer sucked. You didn't have your computer hooked up.

[Brian]

To Silverlight when they first launched.

[Ben Gilbert]

Oh God, Silverlight. Yeah, Silverlight. Microsoft. DRM bullshit. It was like worse than Flash.

[David Rosenthal]

At the same time, Reid was right.

[Ben Gilbert]

That's my point. Right. So so many things kind of had to happen. And I guess I say this also because when people ask me about the hashtag, I have a similar feeling where it's like, had Twitter and social media and Instagram not succeeded and not taken off, no one would give a shit about me or the hashtag. So the same thing was true with 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.

[Chris Messina]

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 dot com. Do you believe that, that they always had this vision and that the DVD by mail was just a placeholder for them?

[Brian]

Not this exact vision, but like 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 concept, 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.

[Ben Gilbert]

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 could 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.

[Chris Messina]

In some ways, business model.

[Ben Gilbert]

Well, in some ways has ushered in. Yes. I mean, YouTube probably, you know, there's no, you know, 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.

[Brian]

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 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. It's interesting to note that.

[Ben Gilbert]

So that's crazy. That prime video hasn't actually taken a cut of Netflix's.

[Brian]

Okay, but here's the thing. I pay Netflix $216 per year before sales tax. I pay Amazon a godly crap ton every year.

[Chris Messina]

You know what, can I make one more analogy? Because this was the matchup of Bezos versus Hastings. 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, 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 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, with the monthly subscription revenue and things like that. But there's an analogy.

[Brian]

Private equity, baby.

[Chris Messina]

Yeah, yeah. The spending money to make money is. Both Bezos and Hastings believe in that.

[David Rosenthal]

Well, when you also, you asked Brian, was it the plan from the very beginning for Netflix to become what it is today?

[Chris Messina]

I don't know that.

[David Rosenthal]

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. They could not have done streaming if they had not done dvd. 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 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.

[Brian]

I forgot about that for sale doctrine, David. That's a good, that's a good call.

[Chris Messina]

Well, and now it's all about owning IP and dealing with like ownership of 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.

[David Rosenthal]

Who actually has more followers on Twitter, Elon or Jack do that.

[Ben Gilbert]

The fact that, like, Elon can Jack on his own platform is. Is something of a. Like, that is a real thing.

[Brian]

I feel like it's like Elon, Donald Trump, and like LeBron James.

[David Rosenthal]

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 on Twitter?

[Chris Messina]

15 million?

[Ben Gilbert]

Yeah, I was gonna say 13.

[Brian]

20 million.

[David Rosenthal]

5.6.

[Chris Messina]

Oh.

[David Rosenthal]

What? Wow.

[Brian]

Nothing.

[Chris Messina]

I was getting.

[Ben Gilbert]

Elon probably has like 35.

[Brian]

What, did he get booted off a who to follow list?

[David Rosenthal]

Elon took himself off 59. I was gonna say 59 million.

[Chris Messina]

I was gonna say by the time.

[David Rosenthal]

This episode comes out, he wants LeBron 60 million.

[Chris Messina]

Well, listen, here's the percentages. 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.

[Ben Gilbert]

Say the home court advantage didn't help Jack all that much.

[Chris Messina]

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. So. It's not necessarily that Jack is the meme lord that Elon Musk is, but. All right, our job right now, by.

[David Rosenthal]

The way, Elon is bigger than LeBron on Twitter.

[Chris Messina]

Really?

[Brian]

I didn't realize. Not Instagram, though. That's.

[Chris Messina]

Wait, who's the. Who's the most followed person on Twitter right now? Quick.

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[David Rosenthal]

I don't know.

[Chris Messina]

Somebody Google that one.

[David Rosenthal]

Maybe Elon, it's entirely.

[Chris Messina]

No, it's probably like Ronaldo or. Or somebody like that. Yeah.

[David Rosenthal]

It'S Obama.

[Ben Gilbert]

What?

[Brian]

No, it's like every time I see 6 years old when they're like, yeah.

[David Rosenthal]

So Obama's rocking 130 million.

[Brian]

Whoa. That's more than LeBron has on Instagram, which is 98 million.

[Chris Messina]

Wow.

[Ben Gilbert]

Okay.

[Chris Messina]

Okay, somebody.

[Brian]

Obama.

[Chris Messina]

We got it.

[Ben Gilbert]

Justin Bieber has 114 million and Katy Perry has.

[Brian]

This is wildly going off the rails.

[Chris Messina]

Yeah, well, because we need to do justice to Jack Dorsey. And I'm going to do it this way, which is 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. Stripe.

[Brian]

And he's up against the only other guy on this list who's currently CEO of two companies.

[Chris Messina]

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.

[Ben Gilbert]

He has the design for status on a, you know. Yeah, line piece of paper. We've all sat us that is the.

[Chris Messina]

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.

[Ben Gilbert]

About in both cases though, right.

[Chris Messina]

You know what, Chris, you should take this go.

[Ben Gilbert]

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, like what is it like ice wine kind of 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, do that. 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? So were you famous with all the.

[David Rosenthal]

With Jack and all the. And all the Twitter folks? In the early days, I was, you.

[Ben Gilbert]

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 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.

[Brian]

The early technical guys that really helped at scale. Like RSA and Alex Payne.

[Ben Gilbert]

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 Elon comes along and granted, I'm sure we'll get to him and does things that are literally like rocket science or car engineering. Those are not just kind of like one little thing that's like, oh, look, there's this random appendage that's built into the apparatus of reality that I can build upon.

[Brian]

Well, let's hold. Okay. 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.

[Ben Gilbert]

Yeah.

[Chris Messina]

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, explain 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.

[David Rosenthal]

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.

[Brian]

Yep.

[Chris Messina]

I have you guys done. You did a specific episode on the Cash app.

[David Rosenthal]

No, we should.

[Brian]

And it was before the rise of the Cash app.

[Chris Messina]

Okay. Because I've obliquely mentioned this on the podcast before about the Cash app alone as a product is worth such a deep dive in Harvard Business School. Just the way that they've made that successful. Okay.

[Ben Gilbert]

We should actually before, since this is like Jack's last kind of. I suppose.

[Chris Messina]

Yes.

[Ben Gilbert]

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, like, 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, yeah, 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 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 normally kind of way of being.

[David Rosenthal]

Jack moved the culture for sure.

[Ben Gilbert]

Yeah. I just want to put that out there as.

[Chris Messina]

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, like, 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, you know, if.

[David Rosenthal]

Yeah.

[Chris Messina]

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 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.

[Ben Gilbert]

A crazy thing to say.

[Chris Messina]

Yeah, listen, Oprah should have trounced him. Now this was a trouncing.

[David Rosenthal]

We should have tipped the scales on that one.

[Chris Messina]

Yeah, I almost wanted to because I thought it was going to be 5050 and then I was just going to make the call because this, this matchup is Patrick Collinson versus Bill Gates. So I would have loved to have.

[Ben Gilbert]

Come up in this one.

[Chris Messina]

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.

[Brian]

Come on, he's a world class entrepreneur. He's one of the best entrepreneurs that ever lived. But you have the most proven entrepreneur versus an in flight entrepreneur.

[Chris Messina]

Okay, but. 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?

[Brian]

Well, Stripe's core product offering probably created more value in the world as a platform than Square than just like just to riff off the previous conversation, the amount of commerce that can happen digitally on the Internet because Stripe exists is like.

[David Rosenthal]

So you're not including the Cash app. Just Square pre Cash app.

[Brian]

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 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 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 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. 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 reverence.

[Chris Messina]

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. If we're talking about the chutzpah of an entrepreneur and we can get into the idea of 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.

[Ben Gilbert]

But I mean, I think you have to start with, and I think this is probably why they're brilliant, is because you start with, well, what is ketchup? What is money? And the fact that the Internet didn't come with payments built in, that 402 was never specified, left this wide gaping hole. And as Ben said, there were companies that 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. Ketchup as a condiment probably. Again, whoever the entrepreneur was that figured out a little bit of tomatoes which were in rapid abundance, and some salt and some other things put together in a can and took advantage of a new medium which was canned and canning, 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, 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 since shells. This is a common thing for humans to do. Let's conceive it in that paradigm for the medium, in the moment that we live in. And that I think is what sort of separates Collison from the ones that came before.

[Brian]

Chris, would you buy Stripe stock if it were public today at $100 billion market cap?

[Ben Gilbert]

I probably would because honestly, there's still more growth to do, there's still more room to grow, whether they're going to be paving the roads of the Metaverse. 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.

[David Rosenthal]

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 wrong.

[Brian]

Are you going crypto, David?

[David Rosenthal]

I'm saying that Bitcoin's market cap is about 8x stripes right now. So think about that. And they were both started at right around the same time.

[Chris Messina]

Just thing is this is a common Parlance right now.

[Unknown Speaker]

VCs and people in Silicon Valley would.

[Chris Messina]

Pay basically any dollar amount to get their hands on Stripe shares right now.

[Brian]

Stripe is a meme as much as a company, just like Tesla.

[David Rosenthal]

But yeah though. And yet Bitcoin is 8x higher valued right now.

[Chris Messina]

Well, 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 enabling other things, the platforms, the APIs and all that stuff, like it's, 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, it's happening right now for you know, a frigging pizza place around the corner.

[Ben Gilbert]

Also, like these things do not seem like they're incompatible, right? I mean like strike no, no, no. If it doesn't already support crypto can.

[Brian]

All right, all right, all right. Whether Ryan McCullough hates crypto. Go on.

[Chris Messina]

Exactly right.

[Brian]

I think he hated Bitcoin. Is that the. Yeah.

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[Ben Gilbert]

Something like that.

[Chris Messina]

Yeah, I'm hot on Solana these days. So yes, I'm off bitcoin. Yeah, Solana's had a.

[Ben Gilbert]

Had a bit down for 17 hours.

[Chris Messina]

Yeah, I know, I know. 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 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.

[Ben Gilbert]

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, I think is one part of it. I think the bigger part of it is I think they just don't give a shit. They don't really have a world changing world building play. Right? Like Elon wants to go to Mars. Like 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 guess where they're going now.

[Chris Messina]

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.

[Ben Gilbert]

So this raises a question, 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 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 and are willing to go there, even if it's uncomfortable. I feel like Elon will go to the galas and stuff like that with Grimes, not necessarily because he wants to, but because 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 his master plan and vision. And I feel like Larry and Sergey are kind of like. Like they did like the Ellison thing, they bought their island and now they're gonna like live there. Because, you know, screw humans, you know, billionaires. Billionaire stuff.

[Brian]

It's like. And like, Elon doesn't really do billionaire stuff. Like he lives in a shab house. Like he lives in a two bedroom, little like maybe 2,000 top square foot house.

[Ben Gilbert]

That's what I mean.

[David Rosenthal]

It's way less than that.

[Ben Gilbert]

Like, they're building like this vision in this world that they want to sort of get to on behalf of other humans, on behalf of the human race. And maybe I'm. I don't 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 and 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.

[Chris Messina]

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 COVID Yes, that's right. You can do these things right. And life is short, you know, and.

[Brian]

No one's blaming you, but you're not going to win our contest that way.

[Chris Messina]

So let me.

[Ben Gilbert]

That's right, that's right.

[Chris Messina]

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, that they. I don't think that they had the entrepreneur, I don't know, spirit, gift, whatever that is.

[Ben Gilbert]

I think that that's what I'm saying.

[Chris Messina]

Yeah.

[Ben Gilbert]

Like, when it comes to the grit of being an entrepreneur in the business world.

[Chris Messina]

Okay.

[Ben Gilbert]

They would prefer.

[David Rosenthal]

Seem like the least gritty people on this list.

[Ben Gilbert]

Yeah. I mean, again, let me also clarify. That isn't to diminish their achievements. That isn't to say that they're less amazing.

[Chris Messina]

Yeah.

[Ben Gilbert]

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 be like, too much blood.

[David Rosenthal]

Can I do real quick two last little feathers for them? YouTube and Android. 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.

[Chris Messina]

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, made those things happen. Right.

[David Rosenthal]

I'm not saying that, like, they should win. I'm just saying, like, I think we got to give them some credit for.

[Chris Messina]

Oh, no. Okay. Before we leave them, I want to make this very, very, very. 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, that we want to create a place where we want to work, where the best and brightest are here.

[Ben Gilbert]

Yeah, I think that's.

[David Rosenthal]

And that was not the case for them. Yeah.

[Ben Gilbert]

I think, like, having. Having worked there and worked in the Google campus and there. 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 have to be super smart.

[David Rosenthal]

Did you feel like you were literally like, wow, this is the assemblage of the best and brightest people on the planet right now.

[Ben Gilbert]

The way that I would evaluate it is on a couple 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, you think about Google Glass, you know, versus, like, the product that, you know, Facebook just launched, 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 it was, like, defensiveness around it that I think Googlers, not all. I don't want to overgeneralize, 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 and loved.

[Chris Messina]

Okay, y' all, great. That 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.

[Brian]

So wait, so hang on before you tell us. Quick proposal here. So the email that you sent us has a bunch of question marks, right?

[Chris Messina]

Because these votes hadn't happened yet. So do you want to guess or.

[Brian]

Should we call our picks definitive and argue and see if we can come to a consensus on this call?

[Chris Messina]

Okay. All right, now, let's.

[Brian]

Let's Let's. I like the idea of guessing. And then we want to hear what the public said.

[Chris Messina]

Guess who you think won. And try to give me some numbers.

[David Rosenthal]

I'm going with Elon. 6040.

[Brian]

Exactly what I was going to say.

[Ben Gilbert]

74, 36.

[Chris Messina]

Elon wins. 62.3 to 37.7.

[Brian]

Boom. Rosenthal.

[Ben Gilbert]

Yeah, very good.

[Chris Messina]

Which means we have to say goodbye to Jeff Bezos.

[Ben Gilbert]

He's going on his rocket ship anyways.

[David Rosenthal]

Yeah, he's saying goodbye to all of us, too.

[Unknown Speaker]

I was just going to say that.

[Chris Messina]

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, Marc 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. 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 AWS to, I.

[Brian]

Don'T know, friggin, being able to attract the shareholders who are going to bear with you for 25 years while you lose money.

[Chris Messina]

We're even talking about. We're even talking about Netflix's recommendation engine. The recommendation engine comes from the software innovations that Amazon created.

[Brian]

Collaborative filtering.

[Chris Messina]

I mean, I don't know even where to go with this.

[Ben Gilbert]

Well, not to mention just like the supply chain innovation and the ability and like prime and like the membership thing.

[Chris Messina]

And prime warehousing fulfillment centers.

[Brian]

Plus, he's got a delivery. I feel like all of 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 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.

[David Rosenthal]

I'll say. So this is going to sound trite, but I actually really believe it. And I think it's true in Bezos's case, all of the amazing stuff that he and Amazon created. I think the most amazing thing is the culture at Amazon and before Amazon.

[Ben Gilbert]

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?

[David Rosenthal]

It's so different, right?

[Brian]

Like they are the most innovative large company.

[David Rosenthal]

Yeah.

[Ben Gilbert]

How though?

[David Rosenthal]

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 paradigm of how to organize companies. Ford was the first industrial manufacturing line, assembly line company. Amazon is the first decentralized company. They really mean the two pizza team thing.

[Ben Gilbert]

Yeah, I mean, actually 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.

[David Rosenthal]

We'Re starting to see it disseminate out into other companies. But it's just going to continue like 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.

[Brian]

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.

[Ben Gilbert]

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 hedge 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.

[Chris Messina]

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 growth like that outside of a petri dish. Right.

[Unknown Speaker]

So if we're talking about this Sam.

[David Rosenthal]

Bankman Fried of his era, if we're.

[Chris Messina]

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.

[Brian]

So yeah, 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 cap wise, revenue wise.

[Chris Messina]

That's just a Wall street thing. Because it was stocks going up at the same time.

[David Rosenthal]

Yeah.

[Brian]

So you look at those five companies, Amazon is the only one that was a dot com company that survived the dot com bubble.

[Chris Messina]

Exactly.

[Brian]

Apple and Microsoft are from the 70s. Facebook and Google are post bubble.

[Chris Messina]

Yahoo's not around.

[Brian]

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 like 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 3 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.

[Chris Messina]

Oh, 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.

[David Rosenthal]

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 secondary.

[Brian]

Hashtag proud investor.

[David Rosenthal]

Yeah, hashtag. Oh yeah. I'm really, I'm going to take a lot of credit for SpaceX. But of all the FAANG 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.

[Chris Messina]

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.

[Brian]

And that it still had 50x left.

[Chris Messina]

10 years ago, 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 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 when Alex Ferguson left Manchester United, 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?

[David Rosenthal]

The book was written by Mike Moritz, too, which makes There you go. Worth reading in and of itself.

[Chris Messina]

Building culture, building a process, a way of doing business. It's looking good for Manchester United this year because they got 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, like, would it be like, oh, my God, Bezos was more of a genius or less of a genius? Because we'll see. We'll find out.

[Ben Gilbert]

With that, I will say, go ahead. 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 ahead, the SS Amazon, so to speak. And then he was able to step aside and let Andy Jassy come in and the guy who's in charge of aws, and there wasn't a huge disruption. I mean, I feel like when Tim Cook took over from Steve Jobs, 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 Apple. Steve Jobs even had sort of parting words like, oh, I cracked the TV and all these other things, and it was sort of just building out generations 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?

[Brian]

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?

[David Rosenthal]

Well, and that's what I think. That's kind of what I meant about that culture. Like, that, the way it works. It's not like some genius. It's not like Bezos, hands down, what you look at the fire phone, right? Like, it's the way that the organization works. Is it's like, 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. So.

[Ben Gilbert]

And to build on that, though, the principle of being the world's most customer centric company 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 onto 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.

[Chris Messina]

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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[Chris Messina]

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. But you know, it helps God and kill Emilio. Yes. Well, that's right. Okay. Right. I forgot about the first time he left. 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.

[Ben Gilbert]

By the way, Brian, is that, Is that Bezos on the wall behind you?

[Chris Messina]

Which one? Yeah, that one. Is that when he was Time magazine person of the year in 1999.

[Ben Gilbert]

99. I mean, that is a run. That is a run.

[Chris Messina]

Yeah. Okay. I'm transitioning to the second semifinal, which is perhaps the most classic matchup you could have in a tournament like this.

[David Rosenthal]

Clash of titans.

[Chris Messina]

This is, this is what the punters in the stands paid their tickets. It is Steve Jobs versus Bill Gates.

[Brian]

I mean, it is taste versus iron.

[Chris Messina]

Okay, you know what we're going to 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% at 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, going against what the voters have said. Bill Gates is a better entrepreneur Capital E than Steve Jobs. Yes. No. Am I, am I canceled?

[Brian]

He is a. This is hard. I mean, it really depends on. Like, this is. This brings it back to the very first thing that we talked about. You know, 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 person, strategist.

[Chris Messina]

What is the difference.

[Brian]

Good at capturing value that they create.

[Chris Messina]

What is the difference between an entrepreneur that creates a product and an entrepreneur that creates a business? So they're a business person.

[David Rosenthal]

That's a good question.

[Ben Gilbert]

To me, it feels like these are two different either archetypes or heroes, or there's Batman and there's Superman, and they're not the same.

[David Rosenthal]

Yes. I love this.

[Ben Gilbert]

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. Yes.

[David Rosenthal]

Are willing to totally Batman, by the way, put ads, Jobs being Superman out.

[Ben Gilbert]

There, where there's a person throwing a hammer at Big Brother and willing to take that on and of course, eventually becomes Big Brother. Whatever, it's fine. On the other hand, there is someone who just is a meticulous planner and executor and finds ways of almost like Jiu Jitsu, using the momentum of other players in the space to benefit their own platform. And that is why, when we evaluate Zuckerberg, Bill Gates is not far behind. Because Zuckerberg absorbs. I mean, he's like Rogue with the X Men, who just absorbs all the talent of people around him and all their ideas. He did that with Bill Gates.

[David Rosenthal]

He's like Robin, too, with Batman. Robin was different, but he's the Batman. He's the next actor to play Batman.

[Ben Gilbert]

Whoever is the Robin that wanted to become Batman and was sort of jealous of him, but sort of also was Robin.

[Brian]

You're talking about Zuck wanting to be Gates.

[Chris Messina]

Right?

[David Rosenthal]

That was what I meant.

[Ben Gilbert]

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, and.

[Chris Messina]

Talking too much about Steve Jobs.

[David Rosenthal]

This is fair. Fair?

[Ben Gilbert]

I thought I was talking about Bill Gates.

[Chris Messina]

Bill Gates, Right.

[Ben Gilbert]

I was comparing and contrasting archetypes, all right. 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.

[David Rosenthal]

Windows Explorer, which was Mosaic. Internet Explorer.

[Chris Messina]

Explorer. Yes. Yeah, yeah, yeah.

[Ben Gilbert]

Well, okay. Anyway, the fact that Windows enabled, just like Stripe, all of these different players to basically become or join the computing revolution, provided again, all roads led back to Windows. That was the Bill Gates playbook. And then Zuck saw that and did the same thing with the Facebook platform.

[Chris Messina]

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 Windows software on every computer the world, it wasn't that Microsoft software, it was Microsoft software.

[Unknown Speaker]

So if we go back to the.

[Chris Messina]

Idea of only one good idea.

[Brian]

Wait, no, it was a computer on every.

[Chris Messina]

Every desktop or every desktop in America. Yes.

[Brian]

Or in the world. I can't remember running Microsoft that they.

[Ben Gilbert]

Never shrinking the size of the ambition.

[David Rosenthal]

Right.

[Brian]

Was running Microsoft software.

[Chris Messina]

So the one good idea. So let me, 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 we. And so if Zuck only has one good idea, which is social and it's. And you can make the argument that Bill Gates, you know, 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.

[Ben Gilbert]

Okay. 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.

[Brian]

Unbelievable.

[Ben Gilbert]

In the early, earliest days of the.

[Brian]

Whole world, discovering the greatest business model in history.

[Ben Gilbert]

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.

[Brian]

He invented FTs.

[Ben Gilbert]

Yes. Yeah, okay, even better. That's even better. And then he monetized it as though they were NFTs.

[Brian]

Yes.

[Ben Gilbert]

Basically every copy of Windows, which had no marginal cost, besides the cost of the disk that it was printed on, could be monetized through subscription. 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.

[Chris Messina]

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. 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.

[Brian]

There's no way mining oil is as profitable as.

[Ben Gilbert]

Probably not, probably not.

[Chris Messina]

So look, if you want to give a frigging Historical Insight Award or something like that, like, 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 funnel that all of modern technology has to go through. That's the greatest insight of our era.

[Brian]

The only better business model than easily replicable software is easily replicable software distributed over the Internet. Internet like it's just one more layer of business model nirvana back to Salesforce, remove all distribution costs.

[Chris Messina]

That's an interesting point because you could argue that as soon as the Internet era comes, Gates is done.

[Ben Gilbert]

I mean, he wrote the book the Road Ahead.

[Chris Messina]

But then is it the doj, David, or is it the fact that.

[Ben Gilbert]

That.

[Chris Messina]

I know that he did.

[Ben Gilbert]

He's the only successful antitrust case in Internet history.

[Chris Messina]

Yes, right. But at the same time, like, yeah, I don't know. Actually, I don't know.

[David Rosenthal]

It may have been. Well, I think this one truly is debatable. I think the one set one point of view is like, look, 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 it.

[Ben Gilbert]

Then.

[David Rosenthal]

On the other hand, the DOJ case was about Internet Explorer. They were right there.

[Chris Messina]

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 play, right, 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.

[Ben Gilbert]

I want to point something out that also just in the way that history doesn't rhyme. But it echoes. No, whatever it is.

[Chris Messina]

It doesn't repeat.

[Ben Gilbert]

When I think about the way in which we think about Zuckerberg as an evil villain, Bill Gates was also an evil villain back in the day. And granted, this is what my TEDx talk is about, but 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 largess the Microsoft millionaires and billionaires have to go, then 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 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. Right.

[Chris Messina]

He can prevaricate and disseminate in ways that Gates never.

[David Rosenthal]

Gates didn't take the time to do.

[Ben Gilbert]

Yeah.

[David Rosenthal]

Zuckerberg didn't realize that the consequences could be that bad.

[Ben Gilbert]

Became more socially kind of 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. So 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. 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 could operate without them at the helm.

[Chris Messina]

Helm.

[Ben Gilbert]

Ben.

[Brian]

So, Chris, I think what you're, you're saying is thank you for coming to my TED Talk. So 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 spaceflight flight with no professional astronauts.

[Ben Gilbert]

Wow. There we go.

[Chris Messina]

All right, well, look, that's no better.

[Ben Gilbert]

Said than timing then.

[Chris Messina]

To the finals.

[Brian]

Kind of unbelievable.

[Chris Messina]

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?

[Ben Gilbert]

We should. I didn't look. We should guess.

[David Rosenthal]

I haven't looked.

[Ben Gilbert]

At least you guys know.

[Brian]

All right, 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%.

[David Rosenthal]

I'll go Elon even higher. 70 to 75%.

[Chris Messina]

Wow.

[Ben Gilbert]

It feels like you guys are right. Although I don't want it to be true, but I think it might be closer. Like 55, 45, Elon.

[Chris Messina]

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.

[Ben Gilbert]

Wow.

[Chris Messina]

Wow.

[Ben Gilbert]

All right.

[Chris Messina]

Which means we need to talk about Elon first because he's the loser. Okay.

[David Rosenthal]

All right. All right.

[Ben Gilbert]

Now that's talk about his achievement from today.

[Chris Messina]

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, in Elon's semifinal 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 army, like, you know, right. Did literally ask the hashtag Twitter army to vote and things like. Or not Twitter, but Tesla Army. 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 living. Yeah. If there's a modern living personification of an entrepreneur, it's Elon Musk.

[David Rosenthal]

He won the living entrepreneur World Cup.

[Ben Gilbert]

Yeah.

[Chris Messina]

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 friggin Medicis or something like that. I don't know anyway. But okay, 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 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 Zip2 thing.

[Unknown Speaker]

There was no question.

[Chris Messina]

He makes this money and he's going to pour it into his next thing, but he pours all of it and.

[Brian]

Then he takes out loans even deeper to finance it.

[Chris Messina]

If we're talking about the spirit of.

[David Rosenthal]

An, the dude never loses, that dude has never lost.

[Chris Messina]

But think about the spirit of an entrepreneur is. 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, zip two, and then PayPal. And then he's like, well, here's what I really want to do 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.

[Brian]

And in this order, I think people forget that, that SpaceX was founded first before Tesla.

[Chris Messina]

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, down. I will go broke to make this vision happen. Not once, not twice, however many fucking times at this point.

[David Rosenthal]

Boring company. We got Neural Link. There's more to. There's still more.

[Ben Gilbert]

I mean, that list is insane.

[Brian]

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, that sure, we've got a trillion dollar company, we got $2 trillion 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. The TAM for the stuff SpaceX is doing could be much larger than any of these big tech companies. Today.

[David Rosenthal]

Yep.

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[David Rosenthal]

Oh, boy.

[Ben Gilbert]

Infinite.

[David Rosenthal]

I think to me, like, you know, I. Same brand. When you about were talking. Second, the biggest thing that is impressive to me about Elon. Well, everything is impressive, but the biggest thing that is impressive is 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.

[Brian]

Bread maker, we talked about this, right?

[David Rosenthal]

So one definition, I think pork, tomatoes, ketchup sauce 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. It all comes down to that.

[Ben Gilbert]

I'm going to try to say this.

[David Rosenthal]

How do I put this?

[Ben Gilbert]

So 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 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 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, 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, 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. These crazy adventures and doing insane things, because he just doesn't give a shit, because his mind works differently. And to be someone who grew up reading comic books, and this is the other observation, 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 to. 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.

[Chris Messina]

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. 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.

[Ben Gilbert]

What about the solar thing?

[Chris Messina]

That's not a failure, like being kicked out of. Well, and also he was kind of kicked out of PayPal, but he also.

[Ben Gilbert]

SolarCity. SolarCity, yeah, yeah, yeah.

[Chris Messina]

But SolarCity isn't that part of Tesla now?

[David Rosenthal]

He bought it.

[Chris Messina]

Yeah, right, right, right, right.

[David Rosenthal]

Okay.

[Ben Gilbert]

There was a scandal or there was something. There was.

[Chris Messina]

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 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.

[David Rosenthal]

I really don't think so. Because space four fricking rockets blew up before the 5th and Tesla was like dead, dead, dead, dead in 2008. And then the frickin 420 thing, that company, almost any other person at the wheel, that company died twice.

[Ben Gilbert]

But the fact that like the shame didn't take him out.

[David Rosenthal]

Right, exactly.

[Ben Gilbert]

He thinks different Jack Dorsey and become Zen, you know, and meditate. He just kind of was like, whatever, you know what I mean? Like, so I smoked some weed, so I did some weird shit, 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.

[Chris Messina]

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.

[Brian]

Oh, I mean, it's kind of Funny that 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 did I need the last 20 years of being in this business? I mean, 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. 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.

[Chris Messina]

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. That is the right way to seg into the winner of this World cup of entrepreneurs voted by you, Steve Jobs. It's taste. It 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.

[Unknown Speaker]

If you think.

[Chris Messina]

Of again 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 shiv people. There's different in nothing that we've talked about. Maybe around the edges for certain people. 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.

[Ben Gilbert]

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 that I want it to. 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, like, so important. And, you know, 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 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 turn off, but was the fact that Steve Jobs did acid and was an integrated thinker.

[David Rosenthal]

I was going to bring that up. I don't think you can talk about Jobs and not talk about lsd.

[Ben Gilbert]

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, 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. 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 can touch and manipulate the. With a computing device, you see a.

[David Rosenthal]

Stylus, we blew it.

[Ben Gilbert]

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.

[Chris Messina]

David, just roll because we can all but give your piece.

[David Rosenthal]

Yeah, you should wrap up up so totally. You know, it's funny, Ben and I unacquired 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 in California, specifically in the 60s, in the counterculture, it was this great hope and dream of a different world, and it failed in almost all of its intended ways. But tech came out of it, and Steve Jobs is the link. That's why I think you have to talk about. About acid. If you're going to talk about Steve Jobs as the greatest entrepreneur of all time or the World cup winner.

[Chris Messina]

Let's say the World cup winner.

[David Rosenthal]

The World cup winner. Because, yeah, the whole, like, everything. Elon, 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.

[Chris Messina]

Yeah. I said in the book that Silicon Valley's culture is a combination of MIT libertarianism with hippie countercultural stuff. Steve Jobs idol, like a lot of people his age, was John Lennon. He. 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. Let me throw this 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, 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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[Chris Messina]

There.

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[Ben Gilbert]

Well, I 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, albums.

[Chris Messina]

But personal computing, Chris, There was a PC industry for 20 years.

[Ben Gilbert]

Personal computing didn't start until the iPhone came out.

[Chris Messina]

Until you had a computer in your pocket. Yes, personal computing. Steve Jobs understood personal computing.

[Ben Gilbert]

Yes.

[Chris Messina]

More than anyone else.

[Ben Gilbert]

Personal in personal computing.

[Chris Messina]

I agree with you.

[Ben Gilbert]

Even though I understand the haters are gonna come on and say, oh, well, personal computing was in reference to time sharing on shared machines or what? 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, like, 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 vision visionary. It's critical to have the vision and also to stand in the face of fear and to continue to go forward. If you think back to 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, 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.

[David Rosenthal]

I love that. I think that's great. Only small thing I'd add is next. It's funny, right? 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.

[Ben Gilbert]

Yep.

[Chris Messina]

World religions. And from Joseph Campbell, that sometimes you have to go out into the wilderness.

[Ben Gilbert]

Yes.

[Chris Messina]

To 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.

[Ben Gilbert]

So good.

[Chris Messina]

I mean, literal MBA level stuff and beyond. So search your podcast app for acquired. Is it acquired podcast or just acquired?

[David Rosenthal]

Just. Okay, you'll find it with acquired. Yeah, just acquired.

[Chris Messina]

Thank you both you and Ben for coming on to do this. Thank you, Chris, for doing this again. And I gotta 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 liked me. Jesus Christ, man. I haven't had fun like this. This was great. So thank you. Thank you for doing this.

[David Rosenthal]

Hey, we do like you, and we think this is a great idea.

[Chris Messina]

Okay?

[Ben Gilbert]

Agree.

[Chris Messina]

Well, next time I come with come at you with a crazy idea, it might not be this good, so. All right, thanks, everybody. And hey, Steve, wherever you're at, you won the World Cup.

[Ben Gilbert]

Congratulations.

[Chris Messina]

Yeah.

[Ben Gilbert]

Sam.