The Mind of Larry Ellison w/ Tom Dotan

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 cares 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 https://discord.com/invite/QUUQUP9szv 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: [email protected] mailto:[email protected] See omnystudio.com/listener https://omnystudio.com/listener for privacy information.

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• 3:24Speaker 06

  Hello and welcome to Better Offline. I'm your host, Ed Zetron.

• 3:39Speaker 06

  On August 17, 1944, the Allied forces pushed Germany out of the south of France. And in the Bronx, a child was born that would go on to become one of the most leathery and ghoulish software orcs in the history of capitalism. I am, of course, talking about Archdemon and Oracle founder Larry Ellison. And today I'm joined by Tom Dotan, a wonderful writer who just had a piece published about this vile old fart in Vanity Fair. Tom, how are you doing?

• 4:03Speaker 07

  I'm doing great, Ed. I really like that X-Men-style Magneto intro to it. So Larry Ellison.

• 4:09Speaker 06

  Yeah, he's like Magneto, but he kind of attracts bad debt at the moment.

• 4:13Speaker 07

  I was about to say, yeah, exactly. His superpower is a magnet for debt.

• 4:17Speaker 06

  It's acquiring companies. Because it's funny, having you on 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 mostly on the financial side. And the thing that keeps popping 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?

• 4:43Speaker 07

  Yes, yes, very much so. They've been doing it for, I can't stand up that particular superlative. We should look into it, but that's been...

• 4:51Speaker 06

  It's 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.

• 5:01Speaker 07

  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 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.

• 5:17Speaker 06

  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?

• 5:29Speaker 07

  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. So this is like, you know, a cohort that produces Steve Jobs and Bill Gates and Steve Wozniak. And Bill, sorry, Larry is a self-taught programmer. He works for a couple of early, early days software companies. I'm not going to remember all of the names, but one of them has an internal project working

• 6:12Speaker 07

  for the CIA, providing a database, basically. Larry is very into the plumbing and database side of things.

• 6:18Speaker 06

  Which was quite boring at the time, right? It wasn't really...

• 6:20Speaker 07

  Extremely boring, right? Yeah, I mean, you have people, sorry, what were you saying?

• 6:24Speaker 06

  No, just keep going.

• 6:26Speaker 07

  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 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.

• 7:08Speaker 07

  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 get that name. And their first client, the company that later becomes Oracle, their first client is the CIA.

• 7:28Speaker 06

  Nice, okay.

• 7:30Speaker 07

  Right.

• 7:30Speaker 06

  Nice. So really like nice beginnings for this company then. And how did it grow? Was it through government services? Was it just because databases were actually a necessary tool?

• 7:41Speaker 07

  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. 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.

• 8:24Speaker 07

  He and Bill Gates are tremendous enemies, later friends.

• 8:27Speaker 06

  What do they argue about? What are they getting at each other's throats over?

• 8:31Speaker 07

  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 that, you know, the business world has ever produced. And Microsoft could only get so big just by selling Windows and, you know, 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, two competitors going at each other. But it was also very personal.

• 9:01Speaker 06

  Yeah, the whole industry also just has never really liked him. That's, this is not because Larry is... 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.

• 9:16Speaker 07

  Yeah, I mean, Oracle is an infamously customer unfriendly company. It's sort of baked into their, baked into their DNA is that they don't really give a shit about how much they can upcharge 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 Marc Benioff is an early Larry Ellison acolyte.

• 9:43Speaker 06

  Oh, really? I actually didn't know that.

• 9:45Speaker 07

  Yeah, yeah, no, I mean, there were, you know, Benioff 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, you know, something that Oracle invests in, and Larry and Marc 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?

• 10:27Speaker 06

  As opposed to, I've heard Oracle referred to as a law firm with a software company attached.

• 10:33Speaker 07

  Yeah, absolutely brutal. Nobody really loves it. The software I hear works pretty well. Like, I give them maybe some credit for the fact that no one has displaced them with maybe a better product, but...

• 10:44Speaker 06

  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 on trying to fix Oracle. But I mean, this is kind of typical of the greater Silicon, we don't need to get too sidetracked, but it's kind of typical of the overall Silicon Valley experience at the moment.

• 11:03Speaker 07

  Yeah, yeah. And Oracle never really changes course. Like, their 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? You know, 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, you know, make it through various upheavals in the tech industry, like the dot-com bust, you know, and 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.

• 11:42Speaker 06

  But it's never been like a rip-roaring 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 companies. It's not necessarily true. It feels like they've just chugged along without dying.

• 11:56Speaker 07

  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. 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 is the easiest way to put it.

• 12:37Speaker 06

  I did not know that. The 90s were crazy, man.

• 12:41Speaker 07

  Yeah, yeah.

• 12:42Speaker 06

  So I actually didn't know that Oracle nearly did that. Because there's so much, there's so many fun stories that happened with this company, but they mostly start in the 2000s, in my experience.

• 12:52Speaker 07

  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, you know, generally the way the internet 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 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, this pretty clever banker, Safra Kats, who I'm sure we're going to talk about.

• 13:28Speaker 06

  Safra Kats?

• 13:29Speaker 07

  Yeah. 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 hostile takeover situation.

• 13:49Speaker 06

  And when they acquired Sun Microsystems, they immediately, it was like a couple months later, filed a suit against Google claiming that its patents were infringed?

• 14:00Speaker 07

  Yeah, I actually don't know that particular story, but sounds, sounds right. Sounds like Oracle.

• 14:04Speaker 06

  Well, actually, while I have you, though, I want to tell my favorite Safra Kats story, which I know I messaged you, but I need the listeners to hear. So...

• 14:10Speaker 07

  Yeah, let's do it.

• 14:11Speaker 06

  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, get shit canned from HP. And by the way, the terms, 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 Hurd as president. So a few years later in 2014, six hours before an announcement saying

• 14:56Speaker 06

  that he and Safra Kats would be co-CEOs of Oracle, Kats turns to Hurd and says, going to Adam Blashinsky of Fortune, that he would not live long enough to regret getting between Larry and her, or attempting to unseat Larry. Five years later, Hurd dies of cancer, making Kats the sole CEO of Oracle. And just to be clear, fuck Mark Hurd. Like, fuck, you don't have to agree with me, Tom, but I think he was a piece of shit. It's good he's gone from the world. Fuck him. Nasty little pervert. Anyway, that's who Larry Ellison was backing. But back to Safra Kats.

• 15:28Speaker 07

  Yeah, no, no, listen, and like you said, Mark Hurd does die of cancer, which is tragically, if you are sympathetic to the guy, a big theme in Larry's life. A lot of the people that he's closest to do end up, do end up dying. But Safra Kats, you know, she comes in, she was a banker at, fuck, I can't remember the name of the banker that she...

• 15:45Speaker 06

  I'm going to look it up real time.

• 15:47Speaker 07

  Yeah.

• 15:48Speaker 06

  I'm going to look it up, yeah.

• 15:49Speaker 07

  So she's a banker. She comes in to basically manage this acquisition era of Oracle. We mentioned Sun Microsystems, which is effectively a bid to acquire the language Java. They buy PeopleSoft, which is incredibly messy. PeopleSoft fights it, becomes a hostile takeover situation. The anti, the Department of Justice gets involved, 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.

• 16:23Speaker 06

  And that was, that was 2021, took on a bunch of debt, and has actually been kind of a catastrophic one because it was so expensive.

• 16:30Speaker 07

  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, 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.

• 17:05Speaker 06

  I also can't get over that it's like women's fashion. First of all, this man has five divorces. He probably should know that there's real money in that. But on top of that, what the fuck's he talking about?

• 17:17Speaker 07

  Well, yeah, he just was flat out wrong. I mean, there's just no, 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, you know, Microsoft is floundering during the Balmer years in this era. Being the huge winners of the hyperscale cloud computing world, and Oracle, which by every means 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 Kats,

• 18:01Speaker 07

  you know, is alongside there. And they're just not a company people pay that close attention to until obviously the AI boom.

• 18:09Speaker 06

  So just so I'm clear, I just really want to, like, make sure I've got this clear. So they did, from what I've 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, a decade ago, and it's like 20-something?

• 18:30Speaker 07

  20. I don't have the exact number in front of me, but yes, in the mid 20s.

• 18:33Speaker 06

  Something like that.

• 18:34Speaker 07

  And goes up to 40.

• 18:34Speaker 06

  That's fucking crazy.

• 18:36Speaker 07

  It is. As for a company that's worth $400 billion, I mean, you have, you know, huge ownership stakes and private companies. But for, for a $400 billion 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 traded private company with Larry in complete control.

• 19:00Speaker 06

  And that's crazy as well, because if you look at, if you look at the kind of revenue of Oracle, adjusted for inflation, it's flat. And 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.

• 19:26Speaker 07

  Yeah, more recently that. But I will, to Oracle's defense, the cash that they spent buying back shares, it's, you could argue it's decently well-spent. 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, you know, 130, 140 dollars 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.

• 20:00Speaker 06

  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's a good person, which we both know he is. Just kidding. 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?

• 20:34Speaker 07

  Yeah, I don't know the exact number, but the thing about Larry-

• 20:38Speaker 06

  He uses his own shares to pay for his life.

• 20:39Speaker 07

  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. 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, what happened there because it was very, very weird, but-

• 21:04Speaker 06

  I mean, what from, just to explain for the listeners, so-

• 21:07Speaker 07

  Sure.

• 21:08Speaker 06

  Couple of weeks back, there was an announcement that Larry was going to dump eight or nine billion dollars worth of shares. And then within one day, it was, actually it was seven billion. And then within one, one day, because everyone went, excuse me, what the fuck was that, Larry? What you, what you 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.

• 21:37Speaker 07

  No, no, he's, he's, he's very much like many other billionaires uses his collateral to, you know, to, to get margin loans and, 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, you know, internal finances and the tens of millions of dollars that he spends on, you know, his yachting excursions and, 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.

• 22:13Speaker 06

  Yeah, he owns an island in Hawaii.

• 22:15Speaker 07

  He owns an island, which I definitely would love to talk about, but, um, and his, his poor head of his family office, this guy named Philip Simon, who's kind of a, a, 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, the phrase is something like a freight train of debt headed toward us right now because of all of his spending.

• 22:41Speaker 06

  Cool.

• 22:42Speaker 07

  And-

• 22:42Speaker 06

  And what was he spending that money on?

• 22:45Speaker 07

  Personal was the category for, for a lot of this stuff. Um, so-

• 22:50Speaker 06

  But what kind of personal?

• 22:52Speaker 07

  Well, look, I think-

• 22:53Speaker 06

  Boats, boats?

• 22:55Speaker 07

  Certainly boats, certainly boats and yachting and real estate, I would say are the easiest things to, 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 a Oracle receptionist. And that is Megan and David, who are both very much figures in Hollywood. And then with his sixth wife, Jolynn Jew, he has five very young children who he had in his late seventies to early eighties.

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  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, another elder child.

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  Like a- Yes.

• 27:02Speaker 06

  Like a-

• 27:02Speaker 07

  Yeah, so we all know David.

• 27:03Speaker 06

  I know about David, Mr. Normal looking, but I didn't know about Meg.

• 27:09Speaker 07

  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. Um, 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, he's always on the go, making Oracle into one of the greatest Silicon Valley companies of all time. 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 called Anna Perna Pictures, which maybe you've heard of?

• 27:48Speaker 06

  I have not.

• 27:49Speaker 07

  Okay, okay. So they make a bunch of movies in the 2010s like Zero Dark Thirty, The Master. She's very close with Catherine Bigelow and funds a lot of her movies. Detroit was one that was an Anna Perna picture that was actually kind of disastrous for them.

• 28:04Speaker 06

  She owns the rights to the Terminator franchise.

• 28:08Speaker 07

  I actually didn't know that.

• 28:09Speaker 06

  I'm looking at the Wikipedia as we speak because I just learned that this person existed. This, this woman's actually been around a bit. She produced Zero Dark Thirty.

• 28:19Speaker 07

  Yeah, yeah, yeah. No.

• 28:20Speaker 06

  That's crazy.

• 28:21Speaker 07

  Between the two of them, I, I think if you're a movie lover, you have a lot more respect for, for Megan because she's really making a go of it. I mean, her-

• 28:27Speaker 06

  She's actually made movies versus whatever it is that David Ellison did?

• 28:33Speaker 07

  David makes Tom Cruise movies, right? I mean, like, you know, Skydance was, was making its name co-producing the later Mission Impossible movies and it makes Star Trek and, and things like that. Like-

• 28:44Speaker 06

  Oh God, he actually produced Mission Impossible Fallout, which I liked. Uh.

• 28:50Speaker 07

  What are you gonna do?

• 28:51Speaker 06

  No, I just feel like I stepped in something. Jesus Christ. But I, this is, 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?

• 29:03Speaker 07

  Yeah, I think more 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 and I really think-

• 29:12Speaker 06

  Guilt?

• 29:13Speaker 07

  Yeah. I, I mean, look, who's, who's to say what lives inside the mind of a man? But I actually think if you look at the completely, I would argue insane money that has gone into or Skydance's buying spree in Hollywood and the likelihood of any of this turning up into a successful, you know, 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 is like a, you know, paternal obligation to his children. Um, and, and a decent amount of guilt over sort of not being there in their early years.

• 29:50Speaker 06

  Cause I admit, I've been trying to work out why, 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. I, on a personal level here, not putting words in your mouth. I think he's a, a dark figure. I think he's connected with Netanyahu, like a really genuinely evil guy.

• 30:17Speaker 07

  Sure.

• 30:18Speaker 06

  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-

• 30:30Speaker 07

  I mean, but isn't that always the case? Is, you know, with these billionaire scions?

• 30:35Speaker 06

  Like, not really. Like, I think that there are plenty of rich people who don't give a shit about their kids and would leave them, leave them on the, on the floor screaming. I mean, Steve Jobs, Steve Jobs, classic, classic, a kind of a child leaver. Like the Behind the Bastards episode where I, we did, uh, God, back when I started Better Offline, it's like he refused to pay child support to the point that the California DA sued him.

• 30:59Speaker 07

  Yeah.

• 30:59Speaker 06

  So I mean, weird that Larry Ellison is less of a deadbeat than Steve Jobs. Interesting. I put him on the ranking board.

• 31:05Speaker 07

  Yeah, yeah. I mean, these people, for whatever reason, contain, contain layers. I don't, 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.

• 31:16Speaker 06

  To, but I already have.

• 31:18Speaker 07

  Yeah, yeah. Okay. I'm not here to convince you, but look, the Hollywood stuff I think is, is super fascinating right now because, and I'm just going to state it outright and I, 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-founded Pixar. He is very close with Bob Iger. He's someone who thinks-

• 31:42Speaker 07

  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 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 it's a much more interesting story of, yep, go ahead.

• 32:09Speaker 06

  How did you come to the conclusion he Larry Ellison doesn't really care about it? Cause I'm very curious about this.

• 32:15Speaker 07

  Well, look, let's, let's put things, I'll be somewhat measured with this, with this. The guy is 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.

• 32:45Speaker 06

  Right.

• 32:45Speaker 07

  That said, the guy is not Rupert Murdoch and, and I don't think, it's a huge mistake to think of him in that way. He's not a newsman.

• 32:52Speaker 06

  And he's not sitting there saying, and now I will make my big wet son buy CNN. 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?

• 33:05Speaker 07

  I think it's a tertiary, if not below, cause in what's going on here.

• 33:09Speaker 06

  Fascinating.

• 33:11Speaker 07

  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. He doesn't care about news. I think this whole thing is a huge nuisance to him, frankly, everything with Barry Weiss.

• 33:37Speaker 06

  And to be clear though, they are obvious, they are definitely right wing people, like just, I just got to be clear about this, but you're, is this based on discussions with sources? Is this the kind of feeling you've gone?

• 33:48Speaker 07

  Yeah, yeah, it is based on discussions with sources.

• 33:50Speaker 06

  Fascinating. Now, I wasn't, 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 son 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 his wet son a big thing and his wet son wanting to be kind of a, a media magnet almost.

• 34:14Speaker 07

  He wants to be big like his dad. I think he sees his billionaire dad having, you know.

• 34:17Speaker 06

  So sad.

• 34:18Speaker 07

  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-

• 34:41Speaker 06

  How is Larry Ellison ensnared in a, in a Israeli corruption scandal?

• 34:46Speaker 07

  Yes, yes. Because he's close to Netanyahu. Safra Katz plays a very large part in that. She's Israeli American and extremely right wing. No, you know, there's no shortage of evidence to see that she is someone who, anyway, we can talk about Safra more if we want, but this, 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

• 35:27Speaker 07

  him no, because I am a technology executive. I am not a media executive. I am not interested in that business.

• 35:33Speaker 06

  Huh.

• 35:34Speaker 07

  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, the light in the way. He gives a billion dollars to Elon.

• 35:47Speaker 06

  Is that a quote?

• 35:48Speaker 07

  No, no, that's, I think what the Korean church used to say outside Los Angeles.

• 35:52Speaker 06

  I mean, same.

• 35:53Speaker 07

  You can see from the freeway.

• 35:53Speaker 06

  Yeah, okay.

• 35:54Speaker 07

  Yeah, yeah, yeah, yeah. No, he's, no, but he, he believes that Twitter is the only source of truth. That is a more or less direct paraphrase from several sources.

• 36:04Speaker 06

  That's so fun. I love that.

• 36:07Speaker 07

  Yeah.

• 36:07Speaker 06

  So, yeah, he's quite close with Musk, isn't he?

• 36:10Speaker 07

  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.

• 36:27Speaker 06

  Can you imagine the conversations that those two have? Actually, one of the things, talk of 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-y voice, but he's six foot one and he sounds like this. Sounds very soft spoken for the man I thought he'd be.

• 36:45Speaker 07

  Yeah, I don't know what's, his voice, I have talked to Larry once in my life and that does put me in relatively rare.

• 36:52Speaker 06

  Yeah, I'm surprised he talks to journalists.

• 36:54Speaker 07

  He doesn't, he hasn't talked to journalists in a long time. There was a Forbes piece that came out during the pandemic where they talked about, you know, his, 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, I was doing, when I first joined the Wall Street Journal, I was doing a story on Benioff, 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 Benioff is sort of a master

• 37:36Speaker 07

  at manipulating the press, or at least developing a kind of chummy relationship with them. And so as I was doing this piece, Benioff basically weaponized his Rolodex to get all of his famous friends to call me and tell me how great of a guy he is.

• 37:50Speaker 06

  That's so funny.

• 37:51Speaker 07

  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, but I probably leave him

• 38:01Speaker 06

  alone. Yo-Yo Ma?

• 38:01Speaker 07

  Yeah, yeah, yeah. Oh, Yo-Yo loves that, the billionaire set. He's a big Davos figure, so.

• 38:07Speaker 06

  I didn't know he was like, but that's also just, who else called, if you remember? Or is it just those two?

• 38:13Speaker 07

  Michael Dell called me.

• 38:16Speaker 06

  Wow.

• 38:17Speaker 07

  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 Benioff, you know, he's, 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.

• 38:41Speaker 06

  Well, less so these days, but yeah, yeah, I get what you mean. But keep going.

• 38:44Speaker 07

  Anyway, so, so one of the people that, that he gets to call me is Larry. And I took the call at like, I don't know, 5:30 PM 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.

• 39:08Speaker 06

  What, what does, what does sounding young sound like?

• 39:11Speaker 07

  He doesn't have like a kind of gravelly sort of Tom Waits husky voice or the sort of, you know, you hear Rupert Murdoch kind of, you know, like when Murdoch talks, he kind of just sort of barks and grumbles and-

• 39:23Speaker 06

  Or the Dershowitzian kind of eh, yeah, he doesn't really, he, he looks like he should. He looks like he was born with it, but he, he has this kind of remarkably smooth kind of, he sounds like a, like a guy that would be like a children's social worker.

• 39:38Speaker 07

  Sure, sure. Well, he has enough children to, I, I cut that.

• 39:42Speaker 06

  Yeah, I guess, I guess that is part of the business. But you know what? Let's, let's change gears. I want to know about this goddamn island in Hawaii.

• 39:49Speaker 07

  Lanai, Lanai. I am fascinated by Lanai. I've been to Lanai three times.

• 39:53Speaker 06

  Nice.

• 39:54Speaker 07

  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. But, 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 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 out 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

• 40:39Speaker 07

  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 American state, a company town. But the fact is Larry and his holding company called Pulamal Lanai own 98% of the island. So almost every single business pays rent to Larry.

• 41:01Speaker 06

  And are there residences there, I guess?

• 41:04Speaker 07

  There are some people who own their own homes and so they have private residences, but by and large, you know, the largest employer on the island is Larry Ellison. And he owns both the Four Seasons that are there. 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 build it in the traditional joinery style. He houses them on the island. Yes, sure. He housed them on the island for, 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, the previous owner

• 41:45Speaker 07

  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 decides that there needs to be a new housing complex to provide for the people there, he can basically make it happen.

• 42:05Speaker 06

  But that's so is he well liked by the people of Lanai?

• 42:11Speaker 07

  This is going to be disappointing for you, Ed, but the answer is yes.

• 42:16Speaker 06

  Right. Tell me more.

• 42:18Speaker 07

  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. 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.

• 42:58Speaker 06

  I was gonna say, is this, yeah, this is lineup. Yeah, it's one of those things where there are benefits, but they're mostly ancillary to the larger thoughts of Ellison.

• 43:07Speaker 07

  It's hard to know where one, you know, ends and the other begins.

• 43:10Speaker 06

  It's, you know, they're all, it's weird to say, it could be worse than Larry Ellison, but that is not necessarily a saying, it's not saying he's amazing, but I'm not disappointed by it. 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 either 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.

• 43:38Speaker 07

  Well, I mean, the police state thing, I don't know, there's not too much police there to begin with. It is a very strange place.

• 43:44Speaker 06

  That's kind of what I'm getting at, though. I'm surprised he didn't just have like Larry Force.

• 43:49Speaker 07

  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 Corvette, his Stingray, this kind of bright orange car, you can, you can Google it. And he actually got a ticket once.

• 44:04Speaker 06

  What?

• 44:05Speaker 07

  Yeah, yeah, looked that one up, too. 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. And I think he, he gets the ticket and writes it. And I don't know what happened to that cop, but you know, they, I guess there's some general belief in justice over there.

• 44:27Speaker 06

  Yeah, I mean, also, I think he can probably afford to take it. What an 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 cap to the guy, he fucking sucks, but it's interesting how there are like, kind of gradations of his evil and how he acts.

• 44:47Speaker 07

  Yes. Look, I mean, the fact is, and I was kind of worried when I was working on this story, 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.

• 45:08Speaker 06

  Hilarious.

• 45:09Speaker 07

  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, there's more to life than money, Larry. And I don't really know how much Larry took that to heart.

• 45:25Speaker 06

  I mean, no, I, knowing every, 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.

• 45:58Speaker 07

  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, 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 and into yachts and having lots of wives.

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• 49:39Speaker 06

  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?

• 50:01Speaker 07

  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 a well-known.

• 50:11Speaker 06

  Tell me more about the octopus, just the reader might not have read yet.

• 50:14Speaker 07

  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 as 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 Cephalopod Corp. He has also Octopus Holdings itself. There's another arm called Tentacle Corp. And then his venture capital arm, which invests in Theranos is called Paco.

• 50:48Speaker 06

  I really, I really don't like this because of the octopus murders, which is about the journalist Danny Casalaro, who was investigating something around something called the Promise Software. It was famously, I don't even want to go into too much detail for fear of 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.

• 51:14Speaker 07

  Yeah. So, so, so he believes in kind of the far reachingness of his ambitions. And, and, and so at this current moment, you basically have the core of it, which is Oracle, which has 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 neo-cloud and taken on, as I'm sure you've talked about endlessly on your show, billions and billions of dollars on 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 hundred billion dollar contracts.

• 51:47Speaker 06

  And it's a $300 billion contract over five years. The data center capacity doesn't exist yet. All that good stuff.

• 51:55Speaker 07

  Right, right. Yes. And, 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. So I don't want to single them out more so than CoreWeave and any number of people that are, you know, at this breakneck 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 one, 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, with

• 52:38Speaker 07

  Trump 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, 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. And look, if it pays off, it is, you know, kind of an incredible last stage act for this entrepreneur in his eighties to take this middling company at this point and turn it into one of the great winners of the AI boom

• 53:21Speaker 07

  and kind of rectify the wrongs of missing out on the cloud computing revolution. But if it doesn't work, I mean, they will be the poster child of the AI bust. There's no question.

• 53:32Speaker 06

  I'm not even sure how financially they make it out of it. I know, and I, this is, this is me talking. It's not in the story, but these data centers they're building for OpenAI are all, they're all project financing with most of them being non-recourse, but one or two of them Oracle will be on the hook for. It's just unclear how they work it out if this doesn't work out. Like, what the fuck do they do? Because there's not really another business, is there? Well, I mean, other than the existing ones.

• 54:02Speaker 07

  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 OpenAI has imploded. Right? If OpenAI is no longer able to fund the data centers that they have signed a contract to do. Yeah. Well, right. If 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 exists to service its existing debt. I, 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. And, yeah.

• 54:47Speaker 06

  Yeah, go on, go on.

• 54:48Speaker 07

  Well, I'm just saying, I, 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 you know, they're certainly not the only NeoCloud that's taken on debt in order to fund data center expansion. And so I, I don't, you know, I don't quite see the, the domino effects playing out right now to.

• 55:25Speaker 06

  I mean, not right now. I, 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% bonds 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 built, if they succeed, 300, 400 billion dollars worth of capacity. And there's no buyer in the world that can actually afford it, including OpenAI now. So I mean, the natural answer is, I think the minimum is what you said about them being the poster child

• 56:06Speaker 06

  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, I think it's a certainty, you can disagree, that's fine, but if that's the case, or isn't Larry Ellison quite on the hook for a bunch of margin loans? Like if Oracle's stock crashes?

• 56:32Speaker 07

  Yeah, I mean, I, 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 dark and funny.

• 56:44Speaker 06

  I agree. I think that that might be the, 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?

• 56:56Speaker 07

  I mean, I, I spent a lot of time looking into his personal life. 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.

• 57:19Speaker 07

  Still relatively good. You have his, 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, Jolynn Ju, who is born and raised in China. 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.

• 58:00Speaker 07

  Largely through Larry's money. But he, and this kind of gets to why I was.

• 58:06Speaker 06

  Isn't that the one where Larry Ellison also massively boosted a generational bust?

• 58:13Speaker 07

  Well, has that guy been a bust? I, I actually broke this story with my colleagues when I was at the Wall Street Journal 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, to Michigan. Has, has he been a bust there? I'm not a college football guy.

• 58:30Speaker 06

  Bryce Underwood has apparently not been very good, but I haven't checked recently.

• 58:34Speaker 07

  Yeah, well, I mean.

• 58:36Speaker 06

  They're sticking with him despite the issues, which is a great way of, which is mostly how Oracle's customers feel.

• 58:42Speaker 07

  Yeah, yeah. Or you could even look at, you know, what's going to be the bigger bust, Bryce Underwood or their data center bet, but.

• 58:47Speaker 06

  Jesus, this, this kid is, he's, I feel bad talking shit on what is a child, but

• 58:54Speaker 06

  this was, this wasn't, this is, this is not looking so good. He's ranked 102nd in passing yards and tied 100th with five touchdowns and 70th QBR. Not great.

• 59:06Speaker 07

  That's, that's rough. That's really rough. Well, I, I don't, again, I also don't want to shit on the kid.

• 59:10Speaker 06

  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 gonna.

• 59:18Speaker 07

  Yeah, no, no, I'm with you. But you know, he, he, he exists at the University of Michigan by the grace of, of Larry and his wife Jolynn. And you know, Larry is in this constant pursuit for connection. In, in my interpretation of his personality and talking to his friends, I think he's obsessed with

• 59:41Speaker 07

  the woman that he's with at the time, is the way he explained it 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, 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. I know it's kind of a banal statement, but we kind of, as the country becomes more and more oligarchic, we, we kind of just look to our billionaire overlords and, 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 to just be a, 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 is involved in so many different aspects.

• 1:00:27Speaker 07

  Media and technology and politics. I don't know how much he cares individually about all these things. And at the same time, 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.

• 1:00:46Speaker 07

  But it's also kind of a very lonely.

• 1:00:49Speaker 07

  Yeah, basically through Oracle and I don't know his wives, but you know, I, I don't know where, if someone like that ever finds peace in his life and, and where contentment comes from. And just as like a, a profile subject, I was fascinated by it. 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, I, I hope people find in him as much interest as I did because he really is of the, the richest people, you know, kind of the 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.

• 1:01:34Speaker 06

  It's fascinating to see him as, because like, I'm, I'm prefacing this by saying, I think he's the scum of the earth. I've written probably 25,000 words about Oracle. I'll probably have another 10,000, 15,000 in me before the company dies. I, 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, but well, I guess he does, but they don't have like actual existential threats. So he's sitting around reading fucking books about Napoleon. And being like, I am, I'm damn, I'm white Napoleon, look at me. And it's so funny because

• 1:02:16Speaker 06

  you'd think that the big company and all the money and the Hawaiian island and the five, what, six wives and the. Seventy nine children and the media empire would be up, but it's very obvious nothing is enough for him, which is, I realize is 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.

• 1:02:40Speaker 07

  Well, the yacht thing is actually an interesting story on its own because I, I think he is pretty successful in yachting. I mean, he, the, the oracle, yeah, you know, he, with his oracle team and the BMW team or something, I can't remember how 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.

• 1:03:01Speaker 06

  Didn't he try and say, wasn't he trying to be a sailor himself?

• 1:03:04Speaker 07

  Yeah. Yeah. And he is on the yachts.

• 1:03:05Speaker 06

  But that didn't work out.

• 1:03:06Speaker 07

  Some of the times, well, you know, there's this very kind of harrowing moment in his life. In the, in the late nineties, 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, the Sayonara, I believe, was their yacht. By the way, Lachlan Murdoch was a, was a participant on that, on that race. He was on the yacht. Anyway, they win that race, but Larry is completely freaked the fuck out. After all of that, he, he, he looks death in the eye and is like, yeah, I'm not doing this anymore. And so he gets into Americas 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. And then Larry gets into a protracted legal fight with the

• 1:03:49Speaker 07

  Americas 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, of Americas 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 catamarans or whatever they, 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, the emptiness at the core of this person and, and the search for acceptance, he still, as I understand, attends the Americas Cup races. He's largely rejected by this very waspy community of people who view him as, you know, I don't know, gauche, new money or whatever.

• 1:04:33Speaker 06

  Wait, the waspy, wait, wait, that's amazing. So other rich people reject him?

• 1:04:39Speaker 07

  This is my understanding. Yeah. The New York Yacht Club never really likes the guy. And so, you know. Yeah. And so the Americas Cup still goes on. You know, they, they do it every couple of years. And Larry, as I understand it, still attends this thing, but as a participant. And I talked to a source who was actually on Larry's yacht during one of the, 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.

• 1:05:25Speaker 06

  It's so funny because he's just, it seems like he's in a decades long existential crisis.

• 1:05:31Speaker 07

  Yeah, I think that's right. Certainly when you marry a Ukrainian model in your, in your late sixties and seventies, you have to sort of question where, you know, what kind of.

• 1:05:39Speaker 06

  I mean, that's like 50% of marriages over 50 in England. So that's fair. I, I would love to pretend like I'm kidding. I've known one other person who's done that. Wouldn't say I love the person, but nevertheless.

• 1:05:52Speaker 07

  Speaking of England, by the way, Ed, I know we've gone way long.

• 1:05:54Speaker 06

  Oh, please, please. Oh, yeah. Tony Blair.

• 1:05:56Speaker 07

  Yeah, yeah. He's very close to Tony Blair. He's a single, he's single, single handedly bankrolls the Tony Blair Institute, which is this, you know, NGO.

• 1:06:03Speaker 06

  What the fuck is the Tony Blair Institute? God fucking damn. I leave England and anyway.

• 1:06:10Speaker 07

  We could probably 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 Larry, nearly fed Tony a pesticide laced tomato that he claimed was organic. But 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,

• 1:06:53Speaker 07

  this is part of his search for the cure to cancer. And he evidently bought a pub that was once the favorite pub for C S Lewis and J R R Tolkien.

• 1:07:04Speaker 06

  So just to be clear, Blair or Ellison?

• 1:07:08Speaker 07

  Larry Ellison.

• 1:07:09Speaker 06

  He owns a fucking pub in London. Jesus fuck.

• 1:07:12Speaker 07

  Yeah. It's, I think it's in Oxford, but yes, it was apparently the, the pub. Yeah. The pub for, for C S Lewis and J R R Tolkien. And this really pissed people off, the fact that Larry bought this pub.

• 1:07:25Speaker 06

  I love that. What I love about that, thank you, by the way, as we wrap up, this has been one of my favorite episodes because we still, like Larry Ellison's still an evil gremlin goblin ghoul man, but it sounds like he's just struggling to try and find meaning in the world. Like he's, like he's, um, reminds me of Mr. Frog from Smiling Friends. The listeners, email me if you've watched that, where it's just like, he's done everything and nothing scratches the itch. Almost makes me think the OpenAI thing is just like a, nah, fuck it. Just, I've heard a few, a few sources I've talked to about Ellison have just been like, eh, he's old, he's fucking trying it.

• 1:08:02Speaker 07

  Yeah.

• 1:08:02Speaker 06

  Just going for it.

• 1:08:04Speaker 07

  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 McGorick 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, 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, the running of his company to a degree. How do you want to go out as like the database provider that kind of just ambled along for a bunch of years until it was, I don't know, bought out by private equity or merged into some other, you know,

• 1:08:49Speaker 07

  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 and you're that old and you're that much in control, these are the ways you think.

• 1:09:04Speaker 06

  Tom, it's been such a pleasure having you. You've been listening to Better Offline. Tom, I'll put the link to your, 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.

• 1:09:19Speaker 07

  Thanks so much, Ed. This is great.

• 1:09:29Speaker 06

  Thank you for listening to Better Offline. The editor and composer of the Better Offline theme song is Matt Osowski. You can check out more of his music and audio projects at mattosowski.com. M A T T O S O W S K I dot com. You can email me at [email protected] or visit betteroffline.com to find more podcast links and of course my newsletter. I also really recommend you go to chat dot where's your ed dot at to visit the discord and go to r slash better offline to check out our Reddit. Thank you so much for listening.

• 1:10:01Speaker 03

  Better Offline is a production of Cool Zone Media. For more from Cool Zone Media, visit our website, coolzonemedia.com, or check us out on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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