#404 How Larry Ellison Thinks artwork

#404 How Larry Ellison Thinks

Founders

November 4, 2025

This episode covers the unique way Larry Ellison thinks. I spent over 40 hours reading (and rereading) this book on Ellison written by Matthew Symonds. ⁠ I then spent several days editing down 40 pages of notes into a one-hour nonstop stream of Larry Ellison's ideas.
Speakers: David Senra
**David Senra** (0:00)
So the book I want to talk to you about today is called Softwar, An Intimate Portrait of Larry Ellison and Oracle by Matthew Symonds. The book is about 25 years old. The first time I read this book was about five to six years ago. And I think if you're going to read a biography or a book on Larry Ellison, this is the very first one you should read, because the author had access to Larry Ellison and traveled extensively with him for two years. And they have these unbelievably, just brutally frank conversations in the book. And so I wanted to read the book and look at it through the lens of like, can I get inside of the mind of Larry Ellison? Ellison has had a very unique set of life circumstances. He founded Oracle all the way back in 1976 He's one of the wealthy, fast forward, you know, 50 something years later, he's still one of the wealthiest people in the world. And so I wanted to understand how he thought. Now, the interesting thing about this book is, Ellison annotated this book. So he made an agreement. He could not change anything that the author wrote, but he was able to add his own footnotes in his own words. And so in addition to these brutally frank conversations, by reading the footnotes, you start to understand his point of view and the way his mind works. So that's what I just want to talk to you about a few of those things today. I want to start with the very first thing. Ellison is his own harshest and most unrelenting critic. A huge chunk of this book is Ellison being embarrassed by his performance as CEO of his own company for the first decade and a half of its existence. That's another thing that Ellison has in common with a lot of history-based entrepreneurs and really great entrepreneurs. He has extraordinarily little interest in the recent past, combined with an obsession to read voraciously about history. Ellison refuses to and I think is incapable of resting on his laurels. He was best friends with Steve Jobs for 25 years and I think Steve just absolutely nailed it with why it makes no sense to rest on your laurels and instead you should do this. This is what Steve said. If you do something and it turns out pretty good, then you should just go do something else wonderful and not dwell on it for too long. Just figure out what's next. What interests Ellison is not the last five years, it's the next five years and what he's going to do in that period. Another thing, Ellison is naturally contrarian. Larry and the author get to know each other in the late 90s. The book is written in the early 2000s, and one thing that pops up over and over again is he understood, Ellison understood the truth of the internet earlier and in a more clear way than almost anybody else. And so everybody at the time, their main product, Oracle's main product, was a database. And they're like, oh, it's over. They said that the internet is going to end the database market. And Ellison said, no, the internet is not going to end the database market. It will drastically expand it. Ellison understood better than anyone else the potential impact on the internet, on enterprise computing in general, and on Oracle in particular. While the technology analysts in the investment banks confidently predicted the maturing of the database market, Ellison realized that the internet would exponentially increase both the number of database transactions and the number of people who would interact with Oracle's databases. That would mean the opposite of what the analysts were predicting. That would mean more license growth than the analysts had ever dreamed of. And so that's something he's going to repeat over and over again. He is very comfortable. He's probably only comfortable when he believes and then acts on the belief that very few, if no one else is doing or understands. And when Ellison believes in something, he acts on it in a big way. This term, burning the boats, reappears over and over again in the book. He likes to burn the boats. Ellison's decision to the horror of many colleagues and customers to abandon all further development of client server based applications and concentrate Oracle's entire engineering effort on building for the new computing architecture of the Internet. This idea was fueled by his mantra, which he would repeat over and over again, which is the Internet changes everything. And during this part of the book, he realized, oh my God, we're in the wrong business. And if we stay here, we're dead. He talks at length why he went all in on the Internet early. By getting to the Internet first, assuming that the software could be made to work, Ellison would force Oracle's competitors to become followers. What distinguished Ellison's take on the Internet from that of many other enthusiasts was that he saw it not just as a great way to get information or to go shopping, but as a platform for a completely different and infinitely superior kind of computing. There's a lot of parallels, in my opinion, between what Ellison is seeing in the late 90s, early 2000s, and what is going on in AI today. Right from the outset, he believed that the Internet really did change everything. Another thing that he repeats, which I guess won't be a surprise since I already mentioned that he was best friends with Steve Jobs for 25 years, I don't think you could hang out with Steve Jobs for two and a half decades, and be neighbors with and go on vacation with, if you didn't have this just visceral disgust and hatred for complexity.

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