What I learned from reading Softwar: An Intimate Portrait of Larry Ellison and Oracle by Matthew Symonds.

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[0:01] Although much of my time with him coincided with a period of adversity for Oracle, I never once saw Ellison downcast. His unquenchable optimism and almost messianic self belief never faltered.

[5:06] The single most important aspect of my personality is my questioning of conventional wisdom. My doubting of experts just because they are experts. My questioning of authority. While that can be very painful in terms of your relationships with your parents and teachers it is enormously useful in life. 

[12:19] People — teachers, coaches, bosses — want you to conform to some standard of behavior they deem correct. They measure and reward you on how well you conform — arrive on time, dress appropriately, exhibit a properly deferential attitude — as opposed to how well you do your job. Programming liberated me from all that.

[16:34] I had always believed that at the top of these companies there must be some exceptionally capable people who make the entire technology industry work. Now here I was, working near the top of a tech company, and those capable people were nowhere to be found. The senior managers I saw were conformist, bureaucratic, and very reluctant to make decisions. 

[23:08] Oracle’s first product reflected Larry Ellison’s desire to do something no one else was doing: The opportunity was huge. We had a chance to build the world’s first commercial relational database. Why? Because nobody else was even trying. The other relational database projects were pure research efforts. If we could build a fast and reliable relational database, we would have it made. I thought that relational was clearly the way to go. It was very cool technology. And I liked the fact it was risky. The bigger the apparent risk, the fewer people will try to go there. We would surely lose if we had to face serious competition. But if we were all alone in pursuit of our goal of building the first commercial relational database system, we had a chance to win.

[26:03] Larry is a sprinter. Not a grinder: Although he always talked about technology and Oracle with passion and intensity, he didn’t have the methodical relentlessness that made Bill Gates so formidable and feared. By his own admission, Ellison was not an obsessive grinder like Gates: “I am a sprinter. I rest, I sprint, I rest, I sprint again.” Ellison had a reputation for being easily bored by the process of running a business and often took time off, leaving the shop to senior colleagues.

[30:55] If you speak out in support of small, unimportant innovations that fly in the face of widely held beliefs—I do it all the time—you are likely to be dismissed as stupid or arrogant, and that’s pretty much the end of it. However, if you defend a really big idea that challenges widely held beliefs, you’re likely to generate a mass of hatred, and you just might pay for it with your life. When Galileo defended Copernicus, he was ridiculed, imprisoned, and then threatened with death unless he recanted. Charles Darwin cautiously postponed publishing On the Origin of Species and The Descent of Man for more than twenty years, but that judicious delay did not save him from vicious personal attacks coming from all ranks of contemporary society.

[37:09] Ellison on mistakes he made before the near death experience of Oracle: I was interested in the technology. I wasn’t interested in sales or accounting or legal. If I wasn’t interested in something, I simply ignored it. I just wasn’t paying proper attention to my job. I was doing only the things that interested me. It was the same problem I had in school. But this happened in my forties. I wasn’t a kid anymore.

[38:40] Surviving Oracle’s near death experience made Larry Ellison stronger. It made him happier: After Oracle’s crisis, looking into the abyss and surviving, I felt emotionally strong enough to take a more realistic look at myself. I was tired of striving to be the person I thought I should be. If I was to have any chance at happiness, I had to understand and accept who I really was. 

[42:12] Larry Ellison’s core business philosophy: Larry Ellison says he’s happy only when everyone else thinks he’s wrong. The core of his business philosophy is that you can’t get rich by doing the same thing as everyone else. “In 1977, everyone said I was nuts when I said we were going to build the first commercial relational database. In 1995, everybody said I was nuts when I said that the PC was a ridiculous device — continuously increasing in complexity when it needs to become easier to use and less expensive.”

[50:56] Larry’s great story about how duplication of effort costs Oracle a ton of money.

[53:13] Never, ever, think about something else when you should be thinking about the power of incentives. —Charlie Munger: One of the worst ideas I can remember was when Ray decided we didn’t do enough selling through partners. The sales force convinced him that the way to fix this was to pay more money to the sales force if the deal went through a partner than if the deal came directly to Oracle. For example , if you sold a million - dollar deal directly, Oracle would get a million dollars and you would get a $ 100,000 commission. But if you sold a million - dollar deal through a partner, Oracle would get $ 600,000 and you would get a $ 120,000 commission. Needless to say, our sales force pushed as many deals as they could through partners that year, so the partners were happy. The sales force got higher commission payments for going through partners, so they were happy. The only loser was Oracle.

[57:57] Ellison’s strategy: 1. Pick a fight. 2.Burn the boats: Once I’m finally certain of the right direction, I pick a fight, as I did with Gates. It helps me make my point, and it makes it impossible to do an about—face and go back. Once a course has been plotted, I sail a long way off and burn my boats. It’s win or die.

[1:01:20] Larry Ellison on Bill Gates: Bill and I used to be friends, insofar as Bill has friends. Back in the eighties and early nineties , all the people in the PC software industry hated Bill because they feared Bill. But Oracle didn’t compete with Microsoft very much back then , so we got on pretty well. As I got to know Bill, I developed a great respect for the thoroughness of his thinking and his relentless, remorseless pursuit of industry domination. I found spending time with Bill intellectually interesting but emotionally exhausting; he has absolutely no sense of humor. I think he finds humor an utter waste of time — an unnecessary distraction from the business at hand. I don’t have anything like that kind of focus or single mindedness.

[1:06:13] Larry Ellison on why Larry Ellison does what Larry Ellison does: My sister told me that 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. The process of self—discovery is one of testing and retesting yourself. I won the Sydney—to—Hobart. Can I win the America’s Cup? I’ll find out. The software business is a more difficult test; it’s a much higher stakes game; there are more people playing this game; it’s a lot more interesting game; and it’s a lot more exciting. If I wasn’t doing this, I’m not sure what else I would be doing with my life.

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“I have listened to every episode released and look forward to every episode that comes out. The only criticism I would have is that after each podcast I usually want to buy the book because I am interested so my poor wallet suffers. ” — Gareth

Be like Gareth. Buy a book: All the books featured on Founders Podcast