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19 December 2025 at 5:14:17 am

Why Larry Ellison Is My Favourite Billionaire

There's an old joke: the difference between God and Larry Ellison is that God doesn't think he's Larry Ellison.


But it's not really a joke. It's a diagnosis.


People worship Steve Jobs for his design taste. Bezos for his customer obsession. Musk for...many things actually.


But Larry Ellison is a dark horse among billionaires. He didn't change the world. But he sure conquered it.


And the reason people miss him is simple: he never offered a flattering story about himself. No noble mission. No moral arc. No "dent in the universe".


He never tried to dress ambition up as virtue.


Just: I want to win.


THE SOURCE


If you want to understand Ellison, start with one of the weirdest biographies ever written: one he argued with.


Softwar is an intimate portrait of Oracle by a reporter who traveled with Ellison for two years. Ellison couldn't change anything but he could annotate it with footnotes, arguing with the author, correcting the record and exposing his own mind in real time.


So you get something founders almost never allow: the myth followed immediately by his argument with it, bound together on the same page.


THE COPYING MACHINE


Oracle wasn't built on invention. Larry didn't invent the relational database. IBM did.


Ellison read their research paper and shipped it first, while IBM was still deciding who should be allowed to sell it and under what conditions.


While IBM was having meetings about meetings, Ellison was selling software that barely worked to customers who didn't know better. The first version was called Oracle Version 2 because nobody buys Version 1 from five guys in California.


The first big customers weren't startups. They were spooks. CIA. Navy Intelligence. Air Force Intelligence. NSA. One week he flew to Washington three times selling the same rough product again and again.


He didn't win because the product was perfect. He won because he was first, loud and relentless.


THE SPRINTER


Larry didn't want to run a company.


His original goal was $10 million in revenue and 50 employees. Enough to control his environment. Enough to not have a boss. Enough to spend his weeks kayaking and riding his motorcycle down the California coast working only when it suited him.


He described himself perfectly: "I'm a sprinter, not a grinder. I rest. I sprint. I rest. I sprint."


His first wife left him because he didn't work enough. His second wife left him because he worked too much.


"Both cases were caused by my self-indulgent without-compromise mode of living."


He never actually wanted to be a CEO. He had two modes, apathetic indifference and complete obsession, and the gap between them is what nearly killed Oracle.


THE NEAR-DEATH


In 1991 Oracle nearly went bankrupt.


The sales org had been booking phantom revenue, selling software that didn't exist to customers who couldn't pay, all to hit quarterly targets. Exotic barter deals proliferated. In one Oracle took a couple of jets from Israeli Aircraft Industries in exchange for software.


When Oracle restated earnings the stock dropped 80%. Larry's fortune collapsed. His third marriage fell apart. His closest friend at the company wanted out.

Underneath all of it was the same voice he'd heard since childhood. His adoptive father: "You'll never amount to anything."


Most CEOs would have sold equity at a massive discount. Larry refused. Even facing margin calls he wouldn't dilute even when that refusal made his situation objectively worse.


So he flew to Japan and structured creative financing with Nippon Steel, trading warrants on Oracle Japan for $80 million in cash. Not Oracle. Oracle Japan. He'd rather do something difficult than surrender control.


Why didn't he quit?


"I couldn't give up. I couldn't prove my father right."


THE CONFESSION


The most interesting part of the crisis isn't the drama. It's the honesty.


Ellison didn't spin it. He admitted incompetence in language that left no room for reinterpretation.


"What kind of CEO lets salespeople write their own contracts? I just didn't know any better."


"I was doing only the things that interested me. It was the same problem I had in school. But this happened in my 40s. I was not a kid anymore."


Other people called his management style extreme delegation. He called it what it was: "It's closer to abdication."


That's rare. One of the richest men alive saying out loud that he was bad at his job.


He learned another painful truth along the way. He used to defend failing executives with one argument: he's very smart. Then someone asked him the only question that matters: "Yeah Larry he's very smart but can he do his fucking job?"


Ellison stared at him. Said nothing. Later he admitted the obvious: "Oh my god he's right. Brilliance is not enough."


THE SYSTEM


After 1991 Ellison became obsessed with engineering everything not just products.


He discovered Oracle had 70 separate HR systems each with its own database. To find out how many people worked at the company you had to query 70 databases all producing slightly different answers.


His reaction was blunt: "Data everywhere and not a drop of information."


He found 200 people globally involved in setting and resetting prices. A pricing committee in California would set a price. Global sales would override it. Geneva would override them. Then Paris Munich and London would each override Geneva. Every country had a different price and everyone believed they were right.


"We were competing against ourselves."


The default state of any organization is chaos. Larry had been a weak king surrounded by strong dukes and in 1991 he learned that the only way to survive was to start executing them.


One senior manager showed up to a budget meeting with 200 slides. Ellison stopped him: "I've got four questions. How much did you sell last year? How much will you sell this year? How much did you spend last year? How much will you spend this year? Answer those first."


The slides weren't information. They were camouflage.


THE ALLIGATOR


In the 90s everyone was afraid of Microsoft. The advice was to avoid them. Be nice. Maybe they'll eat you last.


Ellison's response was characteristically unsubtle: "It's the 'be nice to the alligator and maybe he'll eat you last' theory of survival. I've got a better idea. Let's kill the fucking alligator before he kills us."


He picked a fight with Bill Gates. Publicly. 


Relentlessly. Called Microsoft's software mediocre. Said Gates had no sense of humor which somehow felt more insulting than the technical critiques.


The media loved it. Billionaire versus billionaire. Larry got on the cover of Fortune as "Software's Other Billionaire."


Oracle stopped being compared to other database companies. Now it was compared to Microsoft and IBM.

That wasn't ego. It was positioning.


"We pick our enemies very carefully. It helps us focus."


THE RESPECT


Ellison trashed Gates publicly. Privately he respected him deeply.


One conversation stuck with him. They were on the phone arguing a technical point. Larry made his case. Gates said "I have to think about that. I'll call you back."


Five hours later Gates called. "Yeah I think you're right about that. But what about points A B and C?"

He had spent five hours thinking about a single point admitted he was wrong and then kept going as if the admission itself didn't matter.


"Most people hate to admit they're wrong. It didn't bother Bill one bit. All he cared about was what was right not who was right."


Ellison's conclusion was simple: "That is what makes Bill very dangerous."


THE BURNING


Larry is only comfortable when everyone thinks he's wrong.


In the late 90s analysts said the internet would kill the database market. Larry said the opposite: the internet would exponentially increase database transactions, more users, more queries, more Oracle.


He bet the entire company. Ordered his engineers to abandon client-server applications and go all-in on internet computing. His team thought he was crazy and for a long time there was no proof that he wasn't.


"Once I'm finally certain of the right direction I pick a fight. It helps me make my point and it makes it impossible to do an about-face. Once a course has been plotted I sail a long way off and I burn the boats. It is win or die."


THE PUNCHLINE


Larry has no noble story. No mission statement. No pretense.


"The brain's primary purpose is deception and the primary person to be deceived is the owner."


He stopped deceiving himself in 1991. Realized he was incompetent. Engineered himself into something else.


"Whenever I got too close to a goal I'd raise the bar for fear of actually clearing it. We're endlessly curious about our own limits."


He's 81. Still working. Still acquiring. Still finding the edge.


Silicon Valley is a killing field. Very few technology companies survive.


Larry did.


Everyone studies the wrong founders. They study Jobs and learn taste. They study Bezos and learn customers. They study Musk and learn physics.


Then they get killed by someone who studied Larry.

Vihan Singh @ 2025

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