Better Offline - The Mind of Larry Ellison w/ Tom Dotan

Episode Date: October 21, 2026

In this week's Better Offline, Ed Zitron is joined by writer Tom Dotan to talk about the life of Larry Ellison, his children, his companies, his decades of existential crises, and how all he really ca...res about is his own individual legacy.Tom’s story on Vanity Fair: https://www.vanityfair.com/story/larry-ellison-profile?srsltid=AU7gw4U1qN-QypB2hyj-E4wJoas1nKH1KI3dlXxSJrUS4_O1QWVtz8WO https://archive.ph/MCSfk (archive link) https://x.com/cityofthetown https://substack.com/@tdotan Tom’s latest story on Lightspeed Capital: https://www.newcomer.co/p/after-missing-ais-early-days-lightspeed  Save $10 off a year of my premium newsletter: https://edzitronswheresyouredatghostio.outpost.pub/public/promo-subscription/gzqwkv54e1 YOU CAN NOW BUY BETTER OFFLINE MERCH! Go to https://cottonbureau.com/people/better-offline and use code FREE99 for free shipping on orders of $99 or more. --- LINKS: https://www.tinyurl.com/betterofflinelinks Newsletter: https://www.wheresyoured.at/ Reddit: https://www.reddit.com/r/BetterOffline/  Discord: chat.wheresyoured.at Ed's Socials: https://twitter.com/edzitron https://www.instagram.com/edzitron https://bsky.app/profile/edzitron.com https://www.threads.net/@edzitron Email Me: ez@betteroffline.comSee omnystudio.com/listener for privacy information.

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Starting point is 00:03:18 talking about Archdemon and Oracle founder Larry Ellison, and today I'm joined by Tom Dutton, a wonderful writer who just had a piece published about this vile old fart in Vanity Fair. Tom, how you do him? I'm doing great, Ed. I really like that X-Men style Magneto intro to it. Yeah, he's like Magneto, but he kind of attracts bad debt at the moment. I was about to say, yeah, exactly. His superpower is a magnet for debt. It's acquiring companies because it's funny having you want to talk about Oracle, this is one of my favorite and least favorite subjects because I spent really the last like 10 months digging into this company here and there, but I'm mostly on the financial side. And the thing that keeps popping
Starting point is 00:03:58 up is this is a very strange company. Like they have, I think they may be one of the most aggressive stock buyback companies in the world ever. Yes, yes. Very much so. They've been doing it for, I, I, I can't stand up that particular superlative. We should look into it. It's a 190 billion or more since inception, which isn't the most that anyone's bought, but I think as a percentage of overall revenues and such, it's one of the highest ones. Yeah, absolutely. And it's a key part of their strategy as, you know, they've been basically using their excess cash to buy up stock
Starting point is 00:04:31 and keep Larry Ellison further and further into control. I mean, that's been like a major part in why their stock has been able to be, you know, even relatively flat during the years that the company was basically floundering. So yeah, it's key. Yeah, it's a strange company. So how did we get? What is the actual founding story of Oracle? Because I know that they, I've read vaguely that they worked with the CIA, but how'd this get going?
Starting point is 00:04:54 All right. So basically what happens is Larry Ellison comes out to California in the 1960s. He's a college dropout, sort of a layabout bum, moves out to San Francisco with no real plan in mind. I think he's like a river guide or something in Yosemite for a couple of years. but he has a chip on his shoulder and dreams of being rich. This is extremely important to him from an early age. And he kind of falls in with the burgeoning Silicon Valley crowd of the era.
Starting point is 00:05:19 So this is like a cohort that produces Steve Jobs and Bill Gates and Steve Wozniak. And Larry is a self-taught programmer. He works for a couple of early, early day software companies. I'm not going to remember all of the names, but one of them has an internal project working for the CIA. providing a database, basically. Larry is very into the plumbing and database side of things. Which was quite boring at the time, right? It wasn't really...
Starting point is 00:05:46 Extremely boring, right. Yeah, I mean, you have people... Sorry, Ed. What were you saying? No, just keep going. Yeah, so you have people like Steve Jobs who are interested in the proliferation of personal technology and Bill Gates who's interested in, I guess, I don't know, licensing software, but more or less the same kind of consumer approach. And then Larry is taken by this concept of the relational database, which,
Starting point is 00:06:08 In very simplistic terms is basically about how you can connect one piece of data to another. And we're about to have an explosion of data as all these companies start collecting customer and other sort of, you know, specific data into these mainframes. And Larry is, you know, makes this bet that databases are going to be the future of how businesses are run. And so he's working for this company and their first client or one of their biggest clients is the CIA and the internal name for the project of the CIA software. contract is Oracle. So that's where the name comes from. He leaves that company and then he starts his own. It doesn't, it isn't initially called Oracle, but years down the road, it does take that name. And their first client, the company that later becomes Oracle, their first client is the CIA. Nice. Okay. Right. Nice. So it's really like nice beginnings for this company then. And how did it grow?
Starting point is 00:07:00 Was it through government services? Was it just because databases were actually a necessary tool? I think you could argue it was a great business. at the time. I mean, someone needed to provide this service. There were about to be an explosion of kind of hyper-targeted, not really targeted, but businesses were just trying to make sense of what they could do with the fact that technology was able to suck up transaction data or other specific things. And they were really the best game in town doing it or the most aggressive game in town. And Larry, to his credit, is a technologist and he sort of understands the direction of where the Silicon Valley, you know, ecosystem is going.
Starting point is 00:07:38 Databases are a huge part of it for a lot of years. And they were one of the most effective games in town. Also ruthless, you know, they have huge fights with Microsoft in the 90s. He and Bill Gates are tremendous enemies, later friends. What do they argue about? What are they getting at each other's throats over? Well, basically they were moving in on each other's business, you know, like Microsoft is, you know, Bill Gates is one of the most rapacious, competitive, insane people
Starting point is 00:08:04 that the business world has ever produced. And Microsoft could only get so big just by selling Windows and office productivity tools to people. And then you have, you know, Larry Ellison who wants to own all aspects of the customer relationship. And it was just straight up, you know,
Starting point is 00:08:22 two competitors going at each other. But it was also very personal. Yeah, the whole industry also just has never really liked him. That's... Where are your bills? Well, I mean, yeah. The answer is yes. But yeah, it seems that Larry has kind of pissed off just about everyone, including his customers over the years as well.
Starting point is 00:08:42 Yeah, I mean, Oracle is an infamously customer unfriendly company. It's sort of baked into their DNA is that they don't really give a shit about how much they can upchart their customers because they have complete lock-in from them. And I mean, we can talk about this if you're interested. But one of the interesting kind of diversions in, you know, the direction of software in Silicon Valley is that, Mark Benioff is an early Larry Ellison Acolyte. Oh, really? I actually didn't know that. Yeah.
Starting point is 00:09:11 Yeah, no. I mean, there were, you know, Beniof was really kind of the prodigy salesperson. He's a pure, I'm saying this in the nicest possible way. He's a salesman. He knows how to kind of pitch something in a compelling way to businesses. And, you know, he's obviously become this quasi-cult-like, you know, Hawaiian-infused figure in Silicon Valley now. But the sort of genius, if you want to call it that, of Salesforce, which is a lot of
Starting point is 00:09:34 is something that Oracle invests in, and Larry and Mark have this on-again, off-again friendship, is that what if we built a company that sold to other businesses that didn't hate them? What if we actually had, you know, at least the appearance of being concerned with their satisfaction with the product? As opposed to I've heard Oracle referred to as a law firm with a software company attached. Yeah, absolutely brutal. Nobody really loves it. The software I hear works pretty well. give them maybe some credit for the fact that no one has displaced them with maybe a better product. Well, I think that, well, I'd actually push back on that. It nearly, there's an Oracle story where they nearly bankrupted the town of Birmingham because of the amount of money they were spending
Starting point is 00:10:18 on trying to fix Oracle. But I mean, this is kind of typical of the greater Silicon, we don't need to get too side track, but it's kind of typical of the overall Silicon Valley experience at the moment. Yeah, yeah. And Oracle never really changes course. Like, they're guiding philosophy for many years is we own these customers on this particular aspect of the relationship. So why would we change what we're doing? We have them by the, we have them by the balls. We can keep upcharging them. They're not going to be able to really go anywhere else because of vendor lock-in. And it's not an amazing business, but it's a very solid one. And they're able to kind of make it through various upheavals in the tech industry like the dot-com bust, you know, and
Starting point is 00:10:58 the rise of cloud, which we can also talk about. But effectively, they're just entrenched as part of the plumbing and it's a profitable software business. And that's like a pretty good place to be. But it's never been like a riproaring company, has it? But there's this kind of mythology I've heard like even in interviews with me where people say, oh, they're one of the most profitable company. It's not necessarily true. It feels like they've just chugged along without dying. Yeah. Yeah. I think that's right. Look, they have software margins, which is one of the great innovations of Silicon Valley is that you can basically with very little, you know, capital until recently, You know, capital expenditures charge people an annual basis on an annual basis for your product.
Starting point is 00:11:39 And it's pretty cheap to do it. And Oracle is able to, you know, once they get their financial house in order, they have a real catastrophe in the early 90s because their books were just shit. They could not keep them together. And I mean, I don't honestly remember all the specifics of it, but the company nearly goes bankrupt because they have just not been properly accounting for their revenue. I think it's the easiest way to put it. I did not know that. The 90s were crazy, man. Yeah. Yeah, early 90s. I actually didn't know that Oracle nearly did that because there's so many fun stories
Starting point is 00:12:12 that happen with this company, but they mostly start in the 2000s in my experience. Yeah, no, 100%. I mean, look, the 90s were an odd era within tech generally. But when you get to like the late 90s, the rise of dot com and generally the way the internet that is upending a lot of these businesses, you see a huge panic among, you know, all the entire cohort of Silicon Valley. But what Oracle basically does during this period
Starting point is 00:12:41 is decide to just buy companies. They're not very innovative. They're not really developing new products and they go on this huge spending spree. They bring on, you know, this pretty clever banker, Safra Katz, who I'm sure we're gonna talk about. Saffircats. Yeah.
Starting point is 00:12:55 She comes in, she was a banker. She comes on to be their CFO and basically leads them through this years of, acquisitions. And so they end up buying Sun Microsystems, which was like very upsetting to a lot of people in the tech industry. PeopleSoft was a huge fiasco because they fought it and it became a hospital takeover situation. And when they acquired Sun Microsystems, they immediately, like, it was like a couple months later filed a suit against Google claiming that its patents were infringed. Yeah, I actually don't know that's a particular story, but sounds right. Sounds like Oracle.
Starting point is 00:13:29 Well, actually, while I have you, though, I want to tell my. favorite Saffircats story, which I know I message you, but I need the listeners to hear. So, yeah, let's do it. In the, in late 2000s, Oracle hired this disgraced HP executive called Mark Hurd. And to kind of simmer down the story Mark Hurd had, it appears, allegedly, et cetera, legal disclaimers, repeatedly tried to use his position at HP as a senior executive to have sex with a former reality TV star, hired her for events, would get a little touchy-feely, real gross piece of shit.
Starting point is 00:13:59 get shit canned from HP, and by the way, the terms of the reasons are, because he used HP's funds to do something that wasn't HP related versus the horniness of it all. Larry Ellison writes a letter to the New York Times saying this was tantamount to Apple firing Steve Jobs in the old days, and he'd go on to hire herders president. So a few years later in 2014, six hours before an announcement saying that he and Safra Katz would be co-ceeos of Oracle, Katz turns to herden, says going to Adam Lashinsky of Fortune, that he would not live. long enough to regret getting between Larry and her or attempting to unseat Larry. Five years later, her dies of cancer, making Cats the sole CEO of Oracle. And just to be clear, fuck Mark Hurd. Like, you don't have to agree with me, Tom, but I think he's a piece of shit. It's good. He's gone from the world. Fuck him. Nasty little perver. Anyway, that's who Larry Ellison was backing. But back to SaffraCats. Yeah. No, no, listen. And like you said, Mark Hurd does die of cancer,
Starting point is 00:14:56 which is tragically, if you were sympathetic to the guy, a big theme in Larry's life. A lot of the people that he's closest to do end up dying. But Saffer Katz, you know, she comes in. She was a banker at, I'm fuck, I can't remember the name of the banker that she, I'm going to look it up real time. Yeah. Yeah.
Starting point is 00:15:14 So she's a banker. She comes in to basically manage this acquisition era of Oracle. We mentioned some microsystems, which is effectively a bid to, to acquire the language Java. They buy PeopleSoft, which is incredibly messy. PeopleSoft fights it, becomes a hostile takeover situation. The Antutraud, the Department of Justice gets involved. It takes 18 months. They end up buying the company. They win. They fire a huge percentage of them. They go on to buy a couple of years later, CERner, which is a health tech, a health records company. And that was 2021, took on a bunch of debt, and has actually been kind of a catastrophic one because it was so expensive.
Starting point is 00:15:54 complete catastrophe. It's mostly a Larry Passion Project, which we can also talk about. But yeah, those are the acquisition years of Oracle, which does keep the company growing to a degree, but their products don't really evolve in a very big way. And then in the next couple of years, you know, cloud takes off. You have the cloud boom in the 2010s. And Larry is very dismissive of this technology. He calls it, you know, basically, the tech industry is basically no different than women's fashion. he said it was gibberish. And it ends up really fucking the company for a period of time. I also can't get over that it's like woman's fashion. First of all, this man has five divorces.
Starting point is 00:16:34 He probably should know that there's real money in that. But on top of that, what the fuck's he talking about? Well, yeah, he just was flat out wrong. I mean, there's no way around it. There's no debating, you know, what happened during this period because you have relative Pipsweet companies like, you know, at least on this front, Amazon and Google and Microsoft is floundering during the balmer years in this era. Being the huge winners of the hyperscale cloud computing world, an Oracle, which by every means
Starting point is 00:17:04 had the customer relationships, had the cash to be able to fund it, just fumbles it, fumbles it really, really badly. And so they lead the way for multi-trillion dollar companies to come out of this revolution. And Oracle is just kind of bumbling along, buying back its stock and squeezing its customers, its database customers. So it's like absolutely a dark period that, you know, Mark Hurd is the CEO and Safra Katz, you know, is, is alongside there. And they're just not a company people pay that close attention to until obviously the AI boom. So just so I'm clear, I just really want to like make sure I've got this clear.
Starting point is 00:17:39 So they did, from what I found, $190 billion of stock buybacks. And this allowed Larry Ellison to consolidate his shares because he would, he had massive, he has like 40 something percent of the company. now and that's up from what decade ago when it's like 20 something 20 I don't have the exact number in front of me but yes in the mid 20s and goes up to 40 I mean crazy it is as for a company that's worth 400 billion dollars I mean you have you know huge ownership stakes and private companies but for for a 400 billion dollar company that's publicly traded to have a single person owning 40% of its shares is is almost unprecedented you know I was talking to an analyst who has been covering the company for decades. And his line to me is like, it's basically a publicly
Starting point is 00:18:22 traded private company with Larry in complete control. And that's crazy as well, because if you look at the kind of revenue of Oracle, adjusted for inflation, it's flat. I've looked this up myself. And which is so crazy and there's so many crazy things about it. But it's flat and the company has been sinking tens of billions of dollars into buying back its shares mostly, mostly to benefit one leathery man and his large wet son. Yeah, more recently that. But I will, two Oracle's defense, the cash that they spent buying back shares, you could argue it's decently well spent.
Starting point is 00:19:00 I mean, they were buying these shares at, I don't remember the exact price, but let's say it's in like the 20s or 30s. You know, the stock is trading at $130, $130, $140 now. There's other ways you can use this cash, obviously, but just on a pure financialization basis, I don't think that many people are upset, you know, that their cash was going toward buying back shares. It did prop up the stock. I mean, it propped up the stock, but that money could have also gone literally anywhere else. It also, it propped up the stock for one stockholder. I mean, we're just debating whether Larry Ellison is a good person, which we both know he is. Just kidding.
Starting point is 00:19:37 But it's, I don't know, I just, everything I read about this company and this man is so peculiar because in your story you mentioned as well that he also has his kind of own private financial situations. Like he's, from my count, he has what, at least $21 billion, if not more dollars in personal loans? Yeah, I don't know the exact number, but the thing about Larry- shares to pay for his life. Yeah, yeah, I mean, look, Larry, like most, almost every billionaire out there, doesn't actually spend his own money. You know, he doesn't sell off his shares.
Starting point is 00:20:11 In fact, and again, we can talk about this. There was a very, very bizarre moment a couple of weeks back where it looked like Larry was potentially going to offload billions of dollars in Oracle shares, which he hasn't done in decades and ends up pulling it back a couple of days later. And I'm still trying to dig into what happened there because it was very, very weird. But I mean, just to explain for the listeners. So a couple weeks back, there was an announcement that Larry was going to dump eight or nine billion dollars worth of shares.
Starting point is 00:20:40 And then within one day, it was actually, it was seven billion. and then within one day, because everyone went, excuse me, what the fuck was that, Larry? What you're doing with those shares? They pulled it back and now he's doing another margin loan where he offers the shares up as collateral, which appears to be how he usually does business. Like, Mad Larry doesn't tend to sell his shares. No, no. He's very much, like many other billionaires, uses his collateral to, you know, to get margin
Starting point is 00:21:08 loans and fund his lifestyle and passion projects. And as I reported out in the story, there's a really interesting shareholder lawsuit that happens in the 2000s where you actually get a glimpse at his internal finances and the tens of millions of dollars that he spends on, you know, his yachting excursions and everything to do with his yacht racing, his personal life, his real estate. I mean, the guy is one of the most prodigious holders of properties around the world. Yeah, he owns an island in Hawaii. He owns an island, which I definitely would love to talk about. But, and his poor head of his family office, this guy named Philip Simon, who's kind of a beleaguered figure in the Larry Ellison universe. There are emails that come up in discovery in the shareholder lawsuit where you see Simon basically begging Larry to rein it in. He's like, we have, I think the term is the phrase is something like a freight train of debt headed toward us right now because of all of his spending.
Starting point is 00:22:06 Cool. And what was he spending that money on? personal was the category for a lot of this stuff. Yes, but what kind of personal? Well, look, I think... Boats, boats? Certainly boats. Certainly boats and yachting and real estate.
Starting point is 00:22:23 I would say are the easiest things to look to. There's obviously the stuff as his children get older, two of his children get older and become very interested in... Well, he has seven of them now, but he has two from... He has two from his third marriage. to Barbara Booth, who was an oracle receptionist. And that is Megan and David, who are both very much figures in Hollywood. And then with his six wife, Joel and Jew, he has five very young children who he had
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Starting point is 00:23:24 So if you're looking to connect, then we hope you'll join us. Listen to the Honest Talk podcast on I Heart Radio or wherever you listen to your podcasts. I'm Melissa Jeltson, and in my new podcast, what happened to her, I'm bringing you new stories and conversations every week. Stories about women whose deaths were too quickly ruled a suicide. she was starting to get worried and get scared for her safety. Stories of survival. The only difference between me and her, frankly, was a little bit of luck, because by all rights, I should be dead. Cases that everyone else called closed.
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Starting point is 00:24:39 digital intelligence than there is biological intelligence, it's hard to imagine humans being in control in that scenario. I'm Walter Isaacson, host of the new podcast, The Builders. Right now, we're living through an AI arms race. So I went directly to the people shaping that future. Elon Musk, Dario Hamiday, Alex Carr, Faye Faye-Fei Lee, Palmer Lucky, because I wanted to understand what the most consequential builders believe, what they fear, and where they think this is all headed. Silicon Valley is always saying the cliche thing about the way. way to predict the future is to create it. Well, yeah, it's up to us. But when you say us,
Starting point is 00:25:21 who's us? Is it 400 people that you know in Silicon Valley? Is it me down here in New Orleans? They're brilliant, controversial, and they're already shaping the future. The question is, whose imagination do we want to live in? This is going to determine the fate of nations and economies and the future of humanity. Listen to the builders on the IHeart Radio app, Apple Podcast, or wherever you get your podcast. Damn, my man's fucking, I guess. I mean, that's the first time anyone said that on a podcast about Oracle. But I didn't know he had another elder child.
Starting point is 00:26:07 Like a, like a Megan. I know about David, Mr. Normal look in, but I didn't know about Meg. Oh, Megan is fascinating to me. I actually, honestly, between you and me, Ed, I find her more interesting than David. She's the more kind of like Shakespearean figure of the two. So both of these guys want to go into Hollywood as they grow up. Larry is not involved in their life early, early days. He's always on the go making Oracle into one of the greatest Silicon Valley companies of all time.
Starting point is 00:26:37 And later on, both Megan and David decide they want to be big time Hollywood producers and moguls. Megan is more interested in Oscar bait. She really likes kind of prestigious art films. And so she starts this company. company called Annapurna Pictures, which maybe you've heard of. I have not. Okay, okay. So they make a bunch of movies in the 2010s like Zero Dark 30, The Master.
Starting point is 00:27:01 She's very close with Catherine Bigelow and funds a lot of her movies. Detroit was one that was an Anapurna picture that was actually kind of disastrous for them. She owns the rights to the Terminator franchise. I actually didn't know that. I'm looking at the Wikipedia as we speak because I just learned that this person existed. This woman's actually been around a bit. She produced Zero Dark 30. Yeah.
Starting point is 00:27:25 Yeah. Yeah. No. Between the two of them, I think if you're a movie lover, you have a lot more respect for Megan because she's really making a go of it. She's actually made movies versus whatever it is that David Ellison did. David makes Tom Cruise movies, right? I mean, like, you know, Skydance was making its name co-producing the later Mission Impossible movies. and I make Star Trek and things like that.
Starting point is 00:27:50 Oh, God, he actually produced Mission Impossible Fallout, which I liked. What are you going to do? I just feel like I stepped in something, Jesus Christ. So he was out of their life, but he just came back into it. Was he fully estranged or was he just off doing whatever it is he does all day? Yeah, I think more of the latter. I mean, he does have a relationship with them. There's a huge amount of guilt he feels over the fact that he wasn't there.
Starting point is 00:28:16 and I really think, Yeah, I mean, look, who's to say what lives inside the mind of a man? But I actually think
Starting point is 00:28:25 if you look at the completely, I would argue, insane money that has gone into or Skydances, buying spree in Hollywood and the likelihood of any of this turning up into a successful, you know,
Starting point is 00:28:37 mega conglomerate media company, I think a good amount of it. And this is coming from friends of Larry's and people who've worked with him for decades, say that like, it's driven by what he says, says is like a, you know, paternal obligation to his children and a decent amount of guilt over sort of not being there in their early years. Because I admit, I've been trying to work out why,
Starting point is 00:28:59 because at this point, it's reasonable to argue that Larry Ellison is endangering his future with this skydance deal, that he had to, and with AI as well. And I mean, I really must be clear. I think this man is an evil gremlin, on a personal level here, not putting words in your if I think he's a dark figure. I think he's connected with Net and Yahoo, like a really genuinely evil guy. But it's straight. I was wondering why he would do something so illogical with this. And if the answer is he truly loves his big wet son, that's genuinely one of the funniest possible ways this could go. Because- I mean, but isn't that always the case is, you know, with these, billionaire sions? Like, not really. Like, I think that there are plenty of rich people who don't give a
Starting point is 00:29:44 shit about their kids and would leave them, leave them on the, on the floor screen. I mean, Steve Jobs. Steve Jobs, classic, classic, kind of a child lever. Like, the behind the bastards episode where we did, uh, God, back when I started better off lines, like he refused to pay child support to the point that the California DA sued him. Yeah. So I mean, weird that Larry Ellison is less of a deadbeat than Steve Jobs. Interesting. I'll put him on the ranking board. Yeah. Yeah. I mean, These people, for whatever reason, contain layers. I don't want to come down one way or the other on whether or not Larry Ellison is a good or bad person. And the evidence on the bad side.
Starting point is 00:30:22 I don't think it's possible to, but I already have. Yeah, yeah. Okay. I'm not here to convince you, but look, the Hollywood stuff, I think, is super fascinating right now because, and I'm just going to state it out right. And I make the case, reported out in my story, the man does not give a fuck about the movie industry and the entertainment industry. He never has. There are people in Silicon Valley who have. Steve Jobs, for example, he co-found.
Starting point is 00:30:42 Pixar. He is very close with Bob Eiger. He's someone who thinks a decent amount about the music industry, and even though he ends up kind of destroying it, this is a guy who like cares about media. Larry never does. He doesn't even care about news. And, you know, everything that's going on now with Skydance and CBS News and now CNN, people are trying to like attach to this Larry Ellison worldview and he's, you know, in the midst of a political project. I didn't find that in my reporting. I think it's a much more interesting story of, yep, go ahead. How did you come to the conclusion he, Larry Ellison, doesn't really care about it? Because I'm very curious about this. Well, look, let's let's put things, I'll be somewhat measured with this, with this. The guy is
Starting point is 00:31:26 increasingly conservative. He's very influenced by Elon Musk. He obviously is a huge supporter of the state of Israel and is close to Netanyahu. He has his biases. So the fact that CBS News is tilting they say towards the center, but obviously with Barry Weiss in there, it's pretty clear what's going on. I don't want to claim that that is not in any way a reflection of his politics. That said, the guy is not Rupert Murdoch. And I don't think, it's a huge mistake to think of him in that way. He's not a newsman. He's not sitting there saying, and now I will make my big wet son by CNN.
Starting point is 00:32:03 And once my wet son has his hands around it, I will twist this to the pleasure of Donald Trump. You don't think that that's really what's driving it. I think it's a tertiary, if not below cause and what's going on here. Fascinating. I think with David, he believes he has a vision of turning, you know, this consolidated media company into, you know, a great competitor to Netflix and YouTube. And if we can just kind of stack all these brands together, we can really compete on scale. He's a, he's a Hollywood. He's like, he's a Tom Cruise movie guy.
Starting point is 00:32:35 He doesn't care about news. I think this whole thing is a huge nuisance to him, frankly, everything with Barry Weiss. To be clear, though, they are obviously. They are definitely right-wing people. Like, just got to be clear about this. But is this based on discussions with sources? Is this the kind of feeling you've gone? Yeah, yeah, it is based on discussions with sources. Fascinating. No, to be clear, I wasn't questioning you. I'm like, I want people to hear this because there's a lot of anxiety, understandably, about the Big Wet Sun and his right-wing views and that, this might be a kind of Elon Musk style takeover when it sounds like it's a rich dad buying
Starting point is 00:33:13 his wet son a big thing and his wet son wanting to be kind of a media magnet almost. He wants to be big like his dad. I think he sees his billionaire dad having, you know. So sad. Yeah. Yeah. And you know, there's a fascinating moment and this kind of ties a lot of different themes together. So Netanyahu is embroiled in scandal, obviously never not. But there's a corruption scandal and investigation that's going on in Israel in 2015, 14 or so. And Larry is ensnared in this because there was a period of time when- How was Larry Ellison ensnared in an Israeli corruption scandal? Yes, yes, because he's close to Netanyahu, Safra Katz, plays a very large part in that she's an Israeli-American and extremely right-wing. No, you know, there's no shortage
Starting point is 00:34:01 of evidence to see that she's someone who, anyway, we can talk about sophomore more if we want, This Netanyahu situation, he tries to convince Larry to buy a newspaper that is run by one of his adversaries. I don't remember the exact name of the newspaper, but they're writing all this shit about Netanyahu, and he tries to get Larry to buy it for him and make it more favorable. And Larry basically tells him no. And Ellison, Larry tells the investigators, the Israeli investigators that are looking into this corruption, I told him no, because I am a technology executive.
Starting point is 00:34:35 I am not a media executive. I am not interested in that business. And so you see from, again, in relatively early stage in his kind of right-wing evolution, he's not, he doesn't believe in mainstream media. He thinks Twitter is the truth,
Starting point is 00:34:50 the light in the way. He gives a billion dollars to Elon. No, no. That's, I think, what the Korean church used to say outside Los Angeles. I mean, see from the free way. Yeah, okay.
Starting point is 00:35:00 Yeah, yeah. Yeah, yeah. No, he's, no, but he believes that Twitter is the only source of truth. That is a more or less direct paraphrase from several sources. That's so fun. I love that. Yeah.
Starting point is 00:35:12 So he's quite close with Musk, isn't he? Mm-hmm. Mm-hmm. Yeah. Elon's come out to Lanai several times. There is rumors. I have not corroborated them myself that Larry brought Elon out to Lanai to help him get dry off ketamine. Um.
Starting point is 00:35:32 Can you imagine the conversations that those do have? Actually, one of the things, talking about conversations, Larry Ellison, the thing that always surprised me was he looks like he's going to be a little fella with a booming or gremlin he voice, but he's six foot one and he sounds like this. Sounds very soft-spoken for the man I thought he'd be. Yeah, I don't know what to his voice. I have talked to Larry once in my life, and that does put me in relatively rare. Yeah, I'm supposedly talking to journalists. He doesn't, he hasn't talked to journalists in a long time. There was a Forbes piece that came out during the pandemic.
Starting point is 00:36:05 where they talked about, you know, some of his health initiatives that he's very into. And also they mentioned this farming initiative on Lanai, which I wrote about at the Wall Street Journal. He was trying to reinvent agriculture and create the Tesla of agriculture on Lanai. But anyway, when I first joined the Wall Street Journal, I was doing a story on Beniof, actually, because there was a period in 22, 23, where there were all these activist investors that were piling into Salesforce. trying to force this company to increase its margins. And Beniof is sort of a master at manipulating the press, or at least developing a kind of chummy relationship with them.
Starting point is 00:36:46 And so as I was doing this piece, Beniof basically weaponized his rolodex to get all of his famous friends to call me and tell me how great of a guy he is. That's so funny. Yeah, yeah. No, in a probably 10-minute period of time, I got texts from Gavin Newsom and Yo-Yo Ma. And he offered to introduce me to Jared Kushner,
Starting point is 00:37:05 Yo-Yo Ma? Yeah. Yeah. Yo-Yo loves the billionaire set. He's a big Davos figure. I didn't know he was like, but that's also just, who else called, if you remember, or is it just those two? Michael Dell called me. Wow.
Starting point is 00:37:22 Andy Jassy was supposed to call me, but they ended up just giving me a statement. I can't remember who else was on that list. I don't have those emails anymore since I left the journal, but it was classic Benny Off. You know, he's, he's a, unlike Larry, you know, Mark really does like, you know, cavorting with that class of people and, and then developing relationships with them and, you know, doing each other favors. But, anyway. But yeah, yeah, I get what you mean.
Starting point is 00:37:49 But keep going. Anyway, so, so one of the people that, that he gets to call me is Larry. And I took the call of, like, I don't know, 5.30 p.m. on a, on a weekday. And the thing I was really struck by is the guy was probably, 79 at the time. He sounds so young. I just couldn't believe that he was the age that he was. I mean, I don't know what to make of it. What does what does sounding young sound like? He doesn't have like a kind of gravelly sort of Tom White's husky voice or the sort of, you know, you hear Rupert Murdoch kind of, you know, like when Murdoch talks, he kind of barks and grumbles and all the Dershowitzian kind of eh. Yeah, he doesn't really, he looks like he should. He looks like he was born with it. But he has this kind of remarkably smooth kind of.
Starting point is 00:38:39 He sounds like a guy that would be like a children's social worker. Sure, sure. Well, he has enough children to. Yeah, I guess that is part of the business. But you know what? Let's change gears. I want to know about this goddamn island. Oh, Lanai.
Starting point is 00:38:55 Linai. I'm fascinated by Lanai. I've been to Lanai three times. Nice. Which is a lot of times, considering I've never once stayed at the four seasons, which is the main reason people go to Lanai. So Lanai is one of the larger islands in the chain of Hawaiian islands. It has been owned by one billionaire corporation or individual billionaires for the entirety
Starting point is 00:39:17 of the 20th and 21st century. It's owned most prominently by the Dole Fruit Company, which turns it into the world's largest producer of pineapples. Dole gets bought up by private equity and this real estate magnet named David Murdoch, who runs the island. horribly for 25 years. It gets hugely in debt. He has to sell the island after the financial crisis in 2008. And Larry sort of comes through to buy this island. And he's owned it since 2012. And it's a fascinating thing to go to a place that is, you know, in a modern
Starting point is 00:39:53 American state, a company town. But the fact is Larry and his holding company called Pulama Lanai own 98% of the island. So almost every single business pays rent. to Larry. And are their residences there, I guess? There are some people who own their own homes, and so they have private residences. But by and large, the largest employer on the island is Larry Ellison. And he owns both the four seasons that are there.
Starting point is 00:40:22 There's a small boutique hotel called Hotel Lanai. He has built multiple houses and compounds for himself on the place. I wrote about this in the story, but there's this most recent compound. It took multiple years to build. He hires these Japanese carpenters who built it in the traditional joinery style. He houses them on the island. Yes, sure.
Starting point is 00:40:43 He houses them on the island for a bunch of years while they're doing this. I mean, he runs it like, I think I wrote in the story that the previous owner of it, this guy, David Murdoch, he kind of ran it like a, you'd imagine a billionaire, kind of an arbitrary dictator, sometimes cruel, sometimes generous. Larry basically runs it like a god. I mean, he's so rich that if he, you'd imagine. decides that there needs to be a new housing complex to provide for the people there, he can basically make it happen.
Starting point is 00:41:10 So is he well liked by the people of Lanai? This is going to be disappointing for you, Ed, but the answer is yes. Right. Tell me more. Yeah. I would say it's a reserved yes because the fact of the matter is, look, he's built housing for them, which is something that they need more of. He has built various amenities.
Starting point is 00:41:32 He reopened a pool that the previous owner had closed. The most recent addition is this bowling alley that he, I think it was formerly a community center, that it was converted to a bowling alley. Again, aspects of his personal life kind of bleed into the infrastructure there. So he turned this dilapidated movie theater into what apparently is one of the nicest movie theaters in the country, largely to play the movies that his children are. producing? I was going to say is this, yeah, this is line of, yeah, it's one of those things where there are benefits, but they're mostly ancillary to the larger thoughts of Ellison.
Starting point is 00:42:12 It's hard to know where one, you know, ends and the other begins. Yeah, but it's, you know, they're all, it's weird to say, it could be worse than Larry Ellison, but that is not necessarily saying, it's not saying he's amazing, but I'm not disappointed by, it doesn't surprise me, because especially for an island, I imagine there's a certain degree of he does have to keep them pleased because at some point, at some point you're going to have to whether turn that into a police state or appease people, which I'm surprised he didn't, I'm surprised he didn't just do that. Well, I mean, the police state thing, I don't know.
Starting point is 00:42:47 There's not too much police there to begin with. It is a very strange place. That's kind of what I'm getting at, though. I'm surprised he didn't just have like Larry force. Yeah, well, funny, funny you bring that up because there's a pretty funny story from a couple of years back where, you know, Larry is always zipping around the island on his, his Corvette. his stingray, this kind of bright orange collar. You can Google it.
Starting point is 00:43:07 And he actually got a ticket once. What? Yeah, yeah. Look that one up to. Hawaiian press was all over it. But some enterprising police officer saw a guy going, God knows how fast on their very windy roads. And they pull him over and they see that it's Ellison.
Starting point is 00:43:22 And I think he gets the ticket and writes it. And I don't know what happened to that cop. But, you know, I guess there's some general belief in justice over there. Yeah, I mean, also I think he can probably afford to take it. One interesting thing, because he is definitely an evil goblin ghoul man, but it seems that there are odd times where he's remarkably soft. This is not me trying to capes to the guy. He fucking sucks. But it's interesting how there are like kind of gradations of his evil and how he acts. Look, I mean, the fact is, and I was kind of worried when I was working on this story,
Starting point is 00:43:57 because that is a general perception of him among a certain class, is that the guy is the, you know, an embodiment of a certain type of billionaire asshole, evil, harmless. You know, even Steve Jobs at times found Larry's, you know, greed and fixation on money to be kind of off-putting. hilarious. Yeah, yeah. Larry actually talks about this in a fairly decent commencement address that he gave to USC a couple of years ago where Steve grabs him by the shoulders and he's like,
Starting point is 00:44:23 there's more to life than money, Larry. And I don't really know how much Larry took that to heart. I mean, no, I, no. No, the thing is, is it's like, Larry obviously has a horrible personality, has treated many people, his staff, the people that work with him, the people work around him with contempt. He's treated the tech industry with contempt and his customers with contempt. So yeah, I imagine he's not unilaterally evil in everything he does. And I think that this is one of those situations where it's complex, but he's still like a bad guy. But of course, there are going to be people he's nice to. Unlike Steve Jobs, who was just well known as being a piece. of shit to everyone. Right, but the sense is that he contributed to society because of, you know, the technology and his focus on, you know, consumer electronics and, you know, it felt like it was this artist bestowing his gifts to us, whereas Larry, it's like he's just kind of known for being rich
Starting point is 00:45:19 and into yachts and having lots of wives. The soundtrack to your October from spooky podcasts and chilling playlists to nonstop Halloween radio and more. All the thrills and chills you're craving this season. Press play. I'm Melissa Jeltson, and in my new podcast, what happened to her, I'm bringing you new stories and conversations every week. Stories about women whose deaths were too quickly ruled a suicide.
Starting point is 00:46:15 She was starting to get worried and get scared for her safety. Stories of survival. The only difference between me and her, frankly, was a little bit been in luck because by all rights, I should be dead. Cases that everyone else called closed. They can't convict her, right? Like, she has so much evidence. These stories all start in the same place,
Starting point is 00:46:39 with a woman failed by a system that didn't believe her, that didn't protect her, that didn't see her. No child should ever experience that. And we were babies. She did all of these brave things and came out and spoke about it, and he got a year. You never know who that devil is because he's, where you disguise. Sometimes it's a police uniform.
Starting point is 00:47:01 Listen to what happened to her on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. If there's a million times more digital intelligence than there is biological intelligence, it's hard to imagine humans being in control in that scenario. I'm Walter Isaacson, host of the new podcast, The Builders. Right now, we're living through an AI arms race. So I went directly to the people shaping that future. Elon Musk, Dario Amade, Alex Carr, Faye, Faye Leap, Allmer Lucky, because I wanted to understand what the most consequential builders believe, what they fear, and where they think this is all headed.
Starting point is 00:47:40 Silicon Valley is always saying the cliche thing about the way to predict the future is to create it. Well, yeah, it's up to us. But when you say us, who's us? Is it 400 people that you know in Silicon Valley? Is it me down here in New Orleans? They're brilliant, controversial, and they're already shaping the future. The question is, whose imagination do we want to live in? This is going to determine the fate of nations and economies and the future of humanity.
Starting point is 00:48:10 Listen to the builders on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. It's funny, both of them were kind of trying to do the same thing. Steve Jobs, mostly famous for stuff other people did. Larry Ellison, mostly famous for his company doing well because of buying stuff that other people did. So with that being said, what is Oracle and what is Larry Ellison like right now? Like what is the current state of everything in Ellison world? Yeah. I mean, there's so many parts of Ellison World, which is why I use this metaphor of the octopus to explain him and his ambitions, which I know is kind of...
Starting point is 00:48:56 Tell me more about the octopus, just the reader might not have read yet. Yeah, so that's sort of the structure of my piece. And I know it's kind of there are people who might think of like, oh, wow, brilliant observation to view, you know, a far-reaching power is tantamount to an octopus. But the fact is Larry is obsessed with this image and motif himself. He has multiple holding companies that are octopus-themed. You know, his private equity-ish arm is called the cephalopod corp. He has also octopus holdings itself. There's another arm called tentacle corp.
Starting point is 00:49:29 And then his venture capital arm, which invests in Theranos is called Paco, which is a jack. I really don't like this because of the octopus murders, which is about that gentleman. Danny Casillaro, who was investigating something around something called the promise software. Famously, I don't even want to go into too much detail for fear or get fucking killed. But yeah, I don't love that he's talking about the octopus and promise software. And yeah, there's all sorts of bad stuff about that. Anyway, how normal? keep going. Yeah, so he believes in kind of the far-reachingness of his ambitions. And so at this
Starting point is 00:50:06 current moment, you basically have the core of it, which is Oracle, which is bet the entire company on building AI data centers. They've transitioned themselves from being a, you know, fairly languid database provider into being a neocloud and taken on, as I'm sure you've talked about endlessly on your show, billions and billions of dollars of debt to build data centers effectively for one client in OpenAI, which may or may not have the ability to make good on its multi-a-hundred billion contracts. And it's a $300 billion contract over five years. The data center capacity doesn't exist yet, all that good stuff. Right, right, yes. And building these data centers have been, you know, a total pain in the ass. It's not gone particularly smoothly, as most data center builds at this speed go.
Starting point is 00:50:49 So I don't want to single them out more so than core weave and any number of people that are, you know, at this break net pace to build a capacity for, you know, a small number of frontier labs. But basically they've taken on a huge amount of debt to do that. They also own 15% of TikTok, which is a transaction that is, you know, transverse three administrations or two presidents, but Trump won, Biden, and Trump two. So they are the cloud computing provider and holder of the algorithm for TikTok. There's all the stuff that's going on with his son, David. and then there's his relationship with Trump
Starting point is 00:51:24 and how he's kind of tried to find himself politically in this period. But as I'm sure you've mentioned multiple times on your show, and I get to in the story, it's all built on debt. This is a company that has taken on unprecedented, nearly unprecedented amounts of debt to fund almost every aspect of Larry's ambitions. It has taken Oracle, which was a, as we've said, pretty decent company and turned its cash flow negative in order to handle all the capital expenditures.
Starting point is 00:51:53 And look, if it pays off, it is kind of an incredible last stage act for this entrepreneur in his 80s to take this middling company at this point and turn it into one of the great winners of the AI boom and kind of rectify the wrongs of missing on the cloud computing revolution. But if it doesn't work, I mean, they will be the poster child of the AI bus. There's no question. I'm not even sure how financially they make it out of it. I know, and this is me talking, it's not in the story, but these data centers they're building for Open AI are all, they're all project financing with most of them being non-recourse, but one or two of them, Oracle be on the hook for. It's just unclear how they work it out if this doesn't work out.
Starting point is 00:52:42 Like, what the fuck do they do? Because there's not really another business, is there? Well, I mean, other than the existing ones. Yeah, there is the existing businesses. I haven't really gamed out what it would look like if Oracle, and basically what this means is that Open AI has imploded, right? If Open AI is no longer able to fund the data centers that they have signed a contract to do. Yeah.
Starting point is 00:53:02 Well, right. For whatever reason, you know, the spread gets too large and the debt is so onerous that they would never even make money on, you know, the contracts that Oracle would pay out for them. I guess they would just have, you know, massive, massive layoffs to a point that the company is a shell of its former self and is basically existed. a service its existing debt. I don't know. I mean, I can't honestly think outside of like the financial collapse, an analog to what Oracle would look like if this whole thing falls apart.
Starting point is 00:53:31 And, yeah, go on, go on. Well, I'm just saying I want to be somewhat measured here in the fact that like a lot of things have to go wrong simultaneously and in order for this to be the reality of things. I mean, as it stands now, they have debt that they are currently paying off. the company does have existing businesses that are underwriting it. And they're certainly not the only NeoCloud that's taken on debt in order to fund data center expansion. And so I don't, you know, I don't quite see the domino effects playing out right now to envision. I mean, not right now. I do have to push back on that because even though they are not the core weave level, I mean, they don't have 15% bonn.
Starting point is 00:54:19 currently trading at the level. But here's the thing. Oracle can't really service the debt long term with their current cash flows. If the revenues don't grow with it, it'll absorb it. But the thing is, it's not just, oh, can they afford the debt? It's they're going to have bill, if they succeed, $300, $400,000, $400 billion worth of capacity. And there's no buyer in the world that can actually afford it, including Open AI now. So I mean, the natural answer is, I think the minimum is what you said about them being the poster child for the destruction of all of this capital. But I truly don't. I think that there's a future where Oracle shatters, where they have to sell it, which leads me to my funniest outcome, which is, I think that if this doesn't work out, and I think it's a certainty you can disagree, that's fine. But if that's the case, isn't Larry Ellison quite on the hook for a bunch of margin loans?
Starting point is 00:55:14 Like if Oracle stock crashes? Yeah. I mean, just going down the road of funniest possible outcome, having the eighth richest person in the world getting margin called is very funny, is very darkly funny. I agree. I think that that might be the best possible outcome. And so as we wrap up here, anything about the story I've left out, anything particularly funny or weird that we haven't talked about?
Starting point is 00:55:41 I mean, I spent a lot of time looking into his purpose. personal life. Yeah. Which we talked a bit about his children, but, you know, the man is on his sixth wife right now. How, so, so just to quickly run through his wives, you know, two happen as Oracle is sort of on its way up. He divorces them. They have strange relationships with him.
Starting point is 00:56:04 Still relatively good. You have his third wife, who is the parent of David and Megan. His fourth wife, Melanie Kraft, who is. was a romance novelist, and they were together for a number of years. She wrote a book about a billionaire. Not clear if it was based on him. His fifth wife is a Ukrainian model. And then his current wife, Jolyn Zhu, who is born and raised in China.
Starting point is 00:56:30 She went to school here, I think high school and the University of Michigan. There is a very funny story, in my opinion, in the Wall Street Journal recently, about the fact that this woman is apparently kind of shadow managing their football program. largely through Larry's money. But he, and this kind of gets to why I was. Isn't that the one where Larry Ellison also massively boosted a generational bust? Well, has that guy been a bust? I actually broke the story with my colleagues when I was at the Wall Street Journal
Starting point is 00:57:03 about the fact that they were major donors to an alumni group that was able to recruit away this high school quarterback that had committed to LSU. And then they were able to lure him over to Michigan. Has he been a bust there? a college football day. Bryce Underwood has apparently not being very good, but I haven't checked recently. Yeah. Well, I mean, they're sticking with him despite the issues, which is a great way of, which is mostly how Oracle's customers feel. Yeah, yeah. Or you could even look at, you know, what's going to be the bigger bus, Bryce Underwood or their data center, but, but Jesus. This, this, this, this, this, this is,
Starting point is 00:57:33 This kid is, I feel bad talking shit on what is a child, but, ooh, this was, this wasn't, this is, this is not looking so good. He's ranked a hundred and second in passing yards and tied a hundredth for with five touchdowns and semptieth QBR. Not great. That's, that's rough. That's really rough. Well, I don't, again, I also don't want to shit on the kid. Yeah, yeah, I couldn't do what I would scream, I would die the moment I got tackled once by a varsity high school player. So I'm not going to. Yeah, no, no, I'm with you, but, you know, he exists at the University of Michigan by the grace of Larry and his wife, Jolin. And, you know, Larry is in this constant pursuit for connection in my interpretation of his personality and talking to his friends. I think he's obsessed with the woman that he's with at the time is the way he explained to a couple of my sources. You know, he's extremely committed to someone. and then he kind of just falls out of love. And that almost immediately ends things with them. And I look at someone like him and, you know, we live in the age of billionaires.
Starting point is 00:58:43 I know it's kind of a banal statement, but we kind of, as the country becomes more and more oligarchic, we kind of just look to our billionaire overlords and try to read the tea leaves of what it is they want because they're basically going to be directing the future of this country. And, you know, Larry, I find it just be a mysterious figure who is. obsessed with his legacy. You know, he's reached this point where almost all of his friends have died. You know, he's involved in so many different aspects, media and technology and politics. I don't know how much he cares individually about all these things. And at the same time,
Starting point is 00:59:18 he's reading, you know, constantly reading biographies about Napoleon and Winston Churchill and, you know, as some sources mentioned to me, puts himself up in that league of person and kind of aspires to be this world historical figure. But it's also kind of a very lonely. Yeah, basically through Oracle and I don't know, his wives. But, you know, I don't know where, if someone like that ever finds peace in his life and where contentment comes from. And just as like a profile subject, I was fascinated by it.
Starting point is 00:59:48 So I, you know, in one sense, you see this world spanning ambition of, you know, being at the center of all of these different transformations. At the same time, it's like he seems. kind of like a lonely guy. And I hope people find in him as much interest as I did because he really is of the richest people, you know, kind of a mystery and someone who people haven't written much about. And I feel like, you know, even though this piece was thousands of words long, I could have written so much more because I just don't know if I've gotten to the core of him yet. It's fascinating to see him as, because like I'm brief facing this by saying, I think he's
Starting point is 01:00:25 the scum of the earth. I've written probably two. 25,000 words about Oracle or probably have another 10,000, 15,000 in me before the company dies. It's fascinating hearing, and actually kind of statistically enjoying it, watching these people struggle with living. Like, they have all this money. They don't struggle with anything real in life. They don't have mortgage bit, well, I guess he does, but they don't have, like, actual existential threats. So he's sitting around reading fucking books about Napoleon. Yeah. And being like, I'm damn, on White Napoleon, look at me. And it's so funny because you'd think that the big company and all the money and the Hawaiian Island and the five, six wives and the 79 children and the media empire
Starting point is 01:01:11 would be enough. But it's very obvious nothing is enough for him, which is, I realize kind of a banal statement, but it seems like he didn't, because I know he tried to be a yachter. He tried to go out on his yacht and that didn't work out. Well, the yacht thing is actually, an interesting story on its own because I think he is pretty successful in yachting. I mean, he, the Oracle, yeah, you know, he, with his Oracle team and the BMW team or something,
Starting point is 01:01:37 I can't remember how all the sponsorships worked out. They do win the Americas Cup two times, which if you care about that sort of thing, you know, like, that's that's real accomplishment. But didn't he try and say it. Wasn't he trying to be a sailor himself? Yeah, yeah, and he is on the yachts. Some of the times, well, you know, there's this very
Starting point is 01:01:53 kind of harrowing moment in his life in the, in the late 90s, he participates in the Sydney to Hobart open ocean yachting race. And it was this catastrophe where all the yachts went into a hurricane, a literal hurricane. And several of the sailors died. And, you know, Larry's crew on the Sayanara, I believe was their yacht. By the way, Lachlan Murdoch was a participant on that race.
Starting point is 01:02:16 He was on the yacht. Anyway, they win that race. But Larry has completely freaked the fuck out. After all of that, he looks death in the eye and is like, yeah, I'm not doing this anymore. And so he gets into America's Cup racing, which is kind of, more of a harbor racing yachting thing. And they're pretty successful. They win a couple of times and then they lose.
Starting point is 01:02:32 And then Larry gets into a protracted legal fight with the America's Cup. And then he basically tells them to go fuck themselves and he starts his own league called SAIL GP, which is dedicated essentially to the destruction of America's Cup. That said, from what people in the yachting community tell me, you know, he actually was fairly forward thinking about the future of these hydrofoiling catamorans or whatever they race. And so I actually think there is a ton of respect he has within certain circles of the yachting community. But to get back to like, you know, the emptiness at the core of this person and the search for acceptance, he still, as I understand it, attends the America's Cup races. He's largely rejected by this very waspy community of people who view him as, you know, I don't know, gosh new money or whatever.
Starting point is 01:03:19 Wait, wait, that's amazing. So other rich people reject him. This is my understanding. Yeah, the New York Yacht Club. never really likes the guy. And so, you know, yeah, and so the America's Cup still goes on. You know, they do it every couple of years. And Larry, as I understand it, still attends this thing, but as a participant.
Starting point is 01:03:39 And I talked to a source who was actually on Larry's yacht during one of the last races. And he was like, I was looking at the guy watching him watch this race that he had spent untold amounts of his fortune trying to be a winner in and being accepted by. And he was just rejected by it. And you have this sort of solitary billionaire figure, one of the richest people to ever exist, looking at this community that he wanted to be accepted by and, you know, taken on as its champion, just sort of rejecting him. And, you know, that's kind of where he's at.
Starting point is 01:04:10 It's so funny because he's just, it seems like he's in a decades-long existential crisis. Yeah, I think that's right. Certainly when you marry a Ukrainian model in your late 60s and 70s, you have to sort of question where, you know, what kind of a... I mean, that's like 50% of marriage. marriages over 50 in England. So it's right. That's fair. I, I would love to pretend like I'm kidding. I've known one other person who's done that. I wouldn't say I love the person. But nevertheless. Speaking of England, by the way, Ed. I know we've gone way long. Oh, please. Oh, yeah, Tony Blair.
Starting point is 01:04:41 Yeah, yeah. He's very close to Tony Blair. He's a single, single handily bankrolls the Tony Blair Institute, which is this, you know, NGO. What the fuck is the Tony Blair Institute? God fucking down. I leave England. And anyway, we could probably. We could probably. we do an episode just of the Tony Blair Institute. I'd like to know more about it myself. But as I understand it, it's basically this NGO that has these techno-optimist solutions for African governments, largely pushing software to solve all their problems, including Oracle software, maybe, probably. And so he's very close to Tony Blair. He actually brought Tony out to Lanai once and was showing off the hydroponic greenhouses that he had built there. And nearly fed
Starting point is 01:05:21 Larry, nearly fed Tony a pesticide-laced tomato that he claimed as organic. Anyway, in England, there's a whole bunch going on now that I didn't even have a chance to get to in my story, which is that he's building up an entire health institute at Oxford buying up all kinds of buildings during his, this is part of his search for the cure to cancer. And he evidently bought a pub that was once the favored pub for C.S. Lewis and J.R. Tolkien. So, just to be clear, Blair or Ellison? Larry Ellison. He owns a fucking pub in London.
Starting point is 01:05:56 Jesus, fuck. Yeah, I think it's in Oxford, but yes, it was apparently the pub. Yeah, the pub for C.S. Lewis and J.R. Tolkien. And this really pissed people off the fact that Larry bought this pub. I love that. What I love about that, thank you, by the way, is to wrap up. This has been one of my favorite episodes because we still, like Larry Ellison is still an evil Gremlin-Goblin, goleman, but it sounds like he's just struggling to try and find meaning in the world.
Starting point is 01:06:26 Like he's, like he reminds me of Mr. Frog from Smiling Friends, the listeners email me if you've watched that. Whereas just like, he's done everything and nothing scratches the itch. Almost makes me think the open AI thing is just like a, nah, fuck it. Just I've heard a few sources I've talked to about Ellison have just been like, hey, he's old, he's fucking trying it. Yeah. Just going for it.
Starting point is 01:06:48 And how interested he is in, you know, the data center stuff, he's not very hands-on with it. You know, I've talked to a lot of people who've been out in Abilene, you know, building this shit. And, you know, Clay Magoric and those types are all extremely involved. Larry is sort of this ghostly specter that hangs over the whole project and people there are joking about the fact that, like, we know we can't afford this shit. How are we going to pay for it? It's like, yeah, Uncle Larry will cover it. So, you know, I think he really cares about his legacy. And if you think about the legacy of this company that you founded and he's like the last of the Silicon Valley Titans that's still actually involved in the running of his company to a degree. How do you want to go out as like
Starting point is 01:07:27 the database provider that kind of just ambled along for a bunch of years until it was, I don't know, bought up by private equity or merged into some other, you know, conglomerate or the ones that like fucking went for it and like took on all the fucking debt and became one of the greatest, you know, we were able to avenge the losses of us not being a great cloud computing company. I mean, when you have that much money, you're that old and you're that much in control. these are the ways you think. Tom, it's been such a pleasure having you. You've been listening to Better Offline.
Starting point is 01:07:54 Tom, I'll put the link to your story in the notes. Tom's an excellent writer. He's also done some of the best stuff on AI economics. You've been listening to Better Offline. Tom, thank you for joining us. Thanks so much, Ed. This is great. Thank you for listening to Better Offline.
Starting point is 01:08:16 The editor and composer of the Better Offline theme song is Matt Rosowski. You can check out more of his music and audio projects at Mattisowski.com. M-A-T-T-O-S-K-I-com. You can email me at E-Z at Better Offline.com or visit Better Offline.com to find more podcast links and, of course, my newsletter. I also really recommend you go to chat. Where's Your Ed dot at to visit the Discord and go to R-S-S-Better-O-Line to check out our Reddit. Thank you so much for listening. Better Offline is a production of CoolZone Media.
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