Silicon Valley is a place built on the myth of the "college dropout in a garage." We love the story of the underdog. But the story of Oracle isn't really an underdog story, even though it started with a tiny $2,000 investment. It's a war story. Specifically, it is the story told in Softwar: An Intimate Portrait of Larry Ellison and Oracle, a book that remains arguably the weirdest, most aggressive, and most revealing business biography ever printed.
If you haven't read it, the premise is wild. Journalist Matthew Symonds spent years shadowing Larry Ellison, the founder of Oracle. But Ellison didn't just sit for interviews; he demanded the right to annotate the entire book. The result is a text where the author makes a claim, and Ellison literally interrupts in the footnotes to say, "That’s not how it happened," or "I was right, everyone else was nuts."
Honestly, it’s hilarious. It's also the only way to truly understand how a man who almost died of pneumonia as a baby in the Bronx ended up owning his own Hawaiian island and a fleet of fighter jets.
Why Softwar Still Matters for Business Strategy
Most business books from 2003 are paperweights now. They talk about "synergy" and "dot-com potential." But Softwar: An Intimate Portrait of Larry Ellison and Oracle is different because it documents the exact moment the "Cloud" was born—even if they weren't calling it that yet.
Ellison’s obsession in the book is the "Network Computer." He hated the PC. He called it a "ridiculous, complex device." He wanted everything to live on a central server (the database) and be accessed via a simple terminal. He was about twenty years too early, but he was fundamentally right.
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The Sybase War and the Near-Death Experience
One of the most intense sections of the book covers the early 90s. Oracle almost went bankrupt. Most people forget this. They were booking "future sales" as current revenue—a classic aggressive sales move that blew up in their faces.
- The Crisis: In 1990, Oracle saw its first-ever quarterly loss. The stock tanked 80%.
- The Rivalry: Sybase was actually beating them. They had "stored procedures" and "referential integrity" while Oracle 6 was a buggy mess.
- The Pivot: Ellison didn't play nice. He fired the old guard, brought in Ray Lane, and bet everything on Oracle 7.
It worked. But the book shows the scars. Ellison admits in the footnotes that sacking Geoff Squires was the "worst decision" he ever made. That kind of candor is rare in the C-suite.
The Personality of a "Sprinter"
There is a famous quote in the book where Ellison compares himself to Bill Gates. He says, "I am a sprinter. I rest, I sprint, I rest, I sprint again." Gates was a grinder; he never stopped. Ellison, however, would disappear for weeks to go sailing or obsess over Japanese architecture.
This reveals the "intimate" part of the portrait. Ellison wasn't just a tech mogul; he was a guy who felt he had something to prove because his adoptive father told him he’d never amount to anything.
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He treats business like a sport. He doesn't just want to win; he wants the other guy to lose. He famously quoted Genghis Khan: "It is not enough that I succeed. Everyone else must fail." In Softwar, you see that this isn't just a tough-guy act. It’s his core operating system.
The Footnote Feud
The footnotes in Softwar: An Intimate Portrait of Larry Ellison and Oracle are where the real gold is. Symonds writes about Ellison's personal life—his four marriages, his reckless body-surfing accidents, his $100 million Japanese-style estate.
Then Ellison chiming in?
"I don't think I'm reckless," he'll write, essentially. He views himself as a rational actor in an irrational world. The book highlights his "War on Complexity." He truly believed that if you made software simple and integrated—an "all-in-one" suite—you’d win. At the time, companies like SAP and PeopleSoft (who he later acquired in a hostile takeover) were selling "best-of-breed" individual apps. Ellison thought that was a scam by consultants to make more money.
What Most People Get Wrong About the Oracle Legend
People think Oracle won because they had the best sales team in the world. And they did—their sales culture was legendary and terrifying. But Softwar argues they won because of a specific technical bet: the Internet.
While everyone else was still building for "Client-Server" (where the power is on your desktop PC), Ellison moved the entire company to "Internet Computing" in the late 90s. He told his engineers to stop everything else. If the internet failed, Oracle was "toast."
It didn't fail.
Actionable Insights from the Ellison Playbook
You don't have to be a billionaire to use the logic found in this portrait.
- Question the Experts: Ellison’s favorite thing is being told he’s wrong. If everyone agrees a certain technology is the "future," he looks the other way.
- Integrated vs. Fragmented: Whether you’re building a business or a personal workflow, fragmentation is the enemy. Integration is the "moat."
- The Power of the Pivot: Oracle was months away from death in the early 90s. They didn't "tweak" their way out. They changed their entire management structure and product focus.
- Embrace the "Sprinter" Mentality: You don't have to work 100 hours a week every week. You just have to be able to go harder than anyone else when the "sprint" starts.
Softwar: An Intimate Portrait of Larry Ellison and Oracle isn't just a history book. It’s a manual on how to survive in an industry that tries to kill you every ten years. Ellison is still around, still competing, and still writing his own story.
If you want to understand why Oracle is still a titan in the age of AI, you have to look at the foundations laid in this book. Go find a used copy. Read the footnotes first. They tell the real story of how a "misfit" from Chicago became the most feared man in tech.
Your next steps: Track down a copy of the 2003 hardcover of Softwar to see the original formatting of the footnotes—they are much easier to read than in the digital versions. Focus specifically on the "Epilogue" regarding the PeopleSoft takeover; it is a masterclass in hostile negotiations that still dictates how M&A works in the software industry today. Afterward, compare Ellison's "Network Computer" predictions to your current use of SaaS—you'll realize the "cloud" we use now is exactly what he described thirty years ago.