Softwar: An Intimate Portrait of Larry Ellison and Oracle

by Matthew Symonds, Larry Ellison (Commentary)

In a business where great risks, huge fortunes, and even bigger egos are common, Larry Ellison stands out as one of the most outspoken, driven, and daring leaders of the software industry. The company he cofounded and runs, Oracle, is the number one business software company. Perhaps even more than Microsoft's, Oracle's products are essential to today's networked world.
In Softwar, journalist Matthew Symonds gives readers exclusive and intimate insight into both Oracle and the man who made it and runs it. As well as relating the story of Oracle's often bumpy path to industry dominance, Symonds deals with the private side of Ellison's life. With unlimited insider access granted by Ellison himself, Symonds captures the intensity and, some would say, the recklessness that have made Ellison a legend.
With a new and expanded epilogue for the paperback edition that tells the story behind Oracle's epic struggle to win control of PeopleSoft, Softwar is the most complete portrait undertaken of the man and his empire -- a unique and gripping account of both the way the computing industry really works and an extraordinary life.

Genres: Biography, Business, Nonfiction, Technology, Finance, History, Software

528 pages, Paperback

First published September 23, 2003

Reviews

[Arjun · Rating 3 out of 5]

3.5 stars.

A fun book with a longer blog post (with all my notes) certainly coming soon. I picked up Softwar after Ellison stepped down as CEO of Oracle a couple of months ago.

The most important thing I picked up from Softwar was how often historical trends repeat themselves — fundamentally, the battles we're currently witnessing with SaaS stacks are just iterations of wars that existed between database stacks and enterprise systems in the mid-nineties. Oracle and Ellison were in the thick of this — more than anyone else I've seen, Ellison goes to war (and wins).

A lot of syllogisms touted about business now are lessons from history — while platforms change and major players shift, the game is still fundamentally the same. My favorite example of this is Thiel's philosophy about monopolies — Microsoft might be a dinosaur now, but focusing on monopolising smaller markets (and settling its' many anti-trust cases) was how it rose to prominence early on.

At it's core, Softwar is a fascinating case study of Oracle's rise to prominence and provides an intimate profile of Ellison (one of my favorite characters in the industry), as promised. However, the book probably could have been half the length it was — 600+ pages should give me a "shut the door on this topic" tome of a biography (ala anything Issacson or Gleick writes). There was an excessive amount of detail about Ellison's personal life and a lot of esoteric details of Oracle corporate politics that could have been cut.

My favorite part of the book was seeing what predictions were made for the next 10-15 years in the early 2000s. Slowly realised that Ellison is often radically wrong — but Oracle's bread was won on the basis of him being right more often than not.

Recommended for anyone who's fascinated by history of the software industry, Larry Ellison or enterprise software. Else, skip the book and check out my (forthcoming) notes.

[Tech Historian · Rating 2 out of 5]

I always wanted to read this book, and now a decade later I finally get to it...

Good news
- There's some great reporting embedded in what is really a ~500 page PR piece for Ellison
- The Ray Lane story was worth the read
- Ellison at the emergence of the Internet and struggling (like others) to see the future is a great historical read

Bad news
- Giving the subject of your book permission to have a running commentary on the bottom of each page of your text, makes a mockery of the word journalist. (Doubly so because Ellison's commentary was unnecessary and extraneous. It added nothing to the story. It only proved how badly he compromised the author.)
- The book was in desperate need of an editor. It has periods of true reporting sandwiched in-between verbatim transcripts of Ellison position papers. Easily could have been 1/2 the size and twice as good.
- Tons of tactical details about: Ellison firing execs, defending Ron Wahl is spite of overwhelming evidence of incompetence, management by parachuting in, management only in crisis,etc. but none of this gets put into a coherent description of 1) who is Larry Ellison, 2) why given the permanent dysfunction of the company did it and he succeed. If there ever was a great example of "can't see the forest for the trees" reporting, this book is it.
- The whitewash of the Oracle contracting scandal with the State of California is a great example of when reporters become PR flacks of their subject. The author spent 3 years with Ellison and couldn't conclude "of course Oracle was pushing the edge?" A reporter would have asked if the "sales at any price" culture that almost killed the company in the 1990's had returned. A comprised flak rationalized it.
- Three years with Ellison and Oracle and no summing up of how this talented and flawed human being built the company

[David Kopec · Rating 4 out of 5]

Great Read, but Flawed

True to its subtitle Softwar does indeed deliver an 'intimate portrait' of billionaire business leader Larry Ellison. Unfortunately, although the book is enthralling and features an incredibly interesting format including written responses by Ellison to points raised by Symonds, it falls short in two important areas for biographies.

Firstly, Symonds is not objective - he clearly worked very closely with Ellison and certainly paints a more rosy picture of the complicated man than a more impartial observer may. Secondly, the structure of the book is lacking.The first section of the book (although it is not actually divided as a section) covers Ellison's business life chronoligically and perhaps in too detailed a manner to always remain interesting (there's an alphabet soup of executive names that are never heard from again). Then what I would consider the second section of the book jumps around from business to personal ventures and lacks a real 'feeling of time'. A more traditional fully integrated narrative of the personal and business sides to Ellison's life would perhaps have been superior since it's difficult to gage how much pressures in one area of Ellison's life are affecting the other.

Even with its flaws, Softwar is well written and comes as close to being autobiographical as a non-autobiography can. The subject himself is certainly interesting enough to warrant the 500 pages, and the unique response format is refreshing.

[Tyler · Rating 2 out of 5]

I tried but 200 pages of drivel with Larry Ellison chiming in from the back row is too much for me. There were a couple interesting ideas early on but VP alphabet soup is exhausting to read. It's just not worth it. Go find the couple good quotes and save yourself the hours.

[Barack Liu · Rating 5 out of 5]

533-An Intimate Portrait of Larry Ellison and Oracle-Matthew Symonds-Biography-2003

Barack
2024/08/25

An Intimate Portrait of Larry Ellison and Oracle, first published in 2003. In addition to telling the story of Oracle's bumpy road to industry dominance, Simmons also tells the private side of Ellison's life. Granted unlimited insider access, Simmonds captured the intensity and recklessness that made Ellison a legend.

Larry Ellison was born in 1944 in New York City, US. He studied at the University of Illinois, Urbana-Champaign (no degree) and the University of Chicago (no degree). He is an American businessman and entrepreneur who co-founded the software company Oracle Corporation. He served as Oracle's CEO from 1977 to 2014 and is currently its chief technology officer and executive chairman. He is also known for owning 98% of Lanai, the sixth largest island in the Hawaiian Islands.

Matthew Symonds was born in 1953 in the United Kingdom. He is a British journalist and has served as the executive director of the Larry Ellison Foundation since 2018. He was a co-founder of The Independent in 1986. In 1988, he and Josephine Lawrence McAfee, a lawyer for The Independent, had another daughter, Carrie Symonds. Their daughter is now married to former British Prime Minister Boris Johnson.

Table of Contents
1. Larry and Me
2. On the Road
3. The War on Complexity
4. Beginnings
5. To the Limit
6. Growing Up
7. Best-of-Breed
8. Falling Out
9. The Laboratory

When the author met Larry (Larry Ellison) in 1997, they discussed the problem of "client-server" software architecture in their conversation. Larry believed that software services should be obtained through browsers so that the user's terminal can become very simple. We should show the simple part to the user and hide the complex part, instead of making the client more and more fat instead of thin like the Windows system. At that time, Windows 95 was achieving huge commercial success, and Microsoft's success in the client field seemed to refute Larry's point of view. However, today we see that the trend that Larry emphasized at the time actually does exist. Judging the future itself is very difficult, and it is even more difficult to make such a judgment at the right time. Sometimes, making judgments and choices too early may miss the opportunities of the times. Yesterday, when I was chatting with a college classmate, he mentioned that since graduation, he has deeply realized that "choice is more important than hard work." This topic has actually been the focus of everyone's hot discussion. He shared his thinking on making choices: the first step is to collect information, the second step is to make a decision, and the third step is to go back and collect more information if you feel that the information is not enough.

We, ordinary people, face many important choices in life, such as which school to go to after graduating from high school, which major to choose, what research direction to choose after entering university (especially at the graduate or doctoral level), and which city to work in, which company to join, and what position to take after graduation. The impact of these decisions may last for ten years or even decades. In fact, the same is true for the development of a company. The helmsman of a company needs to make important decisions at critical moments, and these decisions may lead the company in two completely different directions: heaven or hell. When we look back and review, perhaps some choices seem extremely clear, and it seems that we should have chosen a certain option without hesitation. However, in the context of the time, these choices may not be obvious. In fact, everything happens with signs and indications. When you can quickly come to an intuitive conclusion without thinking deeply or conducting in-depth investigations, it is likely that everything is too late. Just like if we join a company before it becomes famous, whether it is the difficulty of joining or the position we get in the company, it is far better than waiting until the company is well-known. However, faced with so many companies and professions, how to choose?

Larry Ellison owns a Gulfstream private jet, drives an S-class Mercedes-Benz, lives in the Hyatt Hotel overlooking Hong Kong's Victoria Harbor, and employs a private bodyguard who used to be a policeman. Is this kind of life enviable? Of course, it is. After all, there are very few people on this earth who can enjoy such a material life. However, does Larry Ellison have no worries? In fact, not only does he have, but he may have more pressure than ordinary people. The Internet bubble in 2001 had a huge impact on Oracle's revenue, and Larry was under great pressure. He went to China to try to develop the Chinese market, but his team had some kind of psychological barrier in their hearts and always felt that this was like making a deal with the devil. So, what should we pursue in life? Is it the pursuit of wealth or the pursuit of happiness? Without a certain foundation of wealth, life will indeed become more difficult. However, no matter how much wealth you have, you cannot avoid some inevitable challenges and troubles in life.

In fact, a large part of the work of CEOs like Larry Ellison is actually selling. It is not only about leading the direction of the company but more importantly, selling products, especially telling other CEO-level figures about the advantages of their products and trying to get them to buy. In essence, this is no different from an individual's efforts to submit a resume and get accepted in an interview to get a job. I have met some people who say that they would rather do some work that does not require dealing with others, such work does not require the assistance of others, nor does it require the assistance of others, and everything is under their own control. At first glance, this seems to be a very ideal state, full of a sense of freedom. However, later I realized that this seemingly ideal state actually greatly limits what we can achieve. The greatest charm of a leadership position may not lie in the generous material rewards it brings but in our ability to bring together the wisdom, time, and strength of others on the cause and goals we are interested in. If our work cannot be built on the work of others, and the work of others cannot be built on our foundation, then our influence on others and the world will be very limited, and the value that can be generated in the end will also be limited. Now that we have made it clear that it is important to interact with others, we need to learn effective communication skills. Communication skills are not just about talking a lot, but knowing what to say and what not to say, which parts need to be elaborated, and which parts can be briefly mentioned. Just like writing a novel, in theory, anyone who can write can write a novel, but the reason why successful writers are successful is that they can accurately express the picture in their minds through words and know where to emphasize.

Larry once said that he didn't mind being called crazy, because in a sense, being considered crazy meant that he was doing something innovative and doing it quickly. However, he also pointed out that such crazy decisions only occur once every three years, because a person cannot always come up with innovative ideas so quickly, nor can he maintain such a high frequency of creativity for a long time. Does this also mean that when we have a good plan, we have the perseverance and determination to stick to it for three years? It is easy to do one thing on a whim today and do another thing tomorrow. But it is not so easy to stick to one thing across time. Larry has always been a strong advocate for the future of the Internet and computers. He opposed "programs running on Windows and client-server architecture". He pursued internal computing, which is completely different from traditional architecture. Microsoft launched Windows 95 in the 1990s and became one of the most successful products in business history at the time. In this context, you can imagine the huge pressure Larry faced. Even successful people like him need to go through these challenges, let alone us.

[Tianze · Rating 1 out of 5]

The author doesn’t seem to know a thing and constant throwing confusing comparison between client-server and the internet architecture- internet is fucking client-server, and it’s an Apple vs Orange comparison between the two. This is a just one of many idiotic descriptions from the author, and it’s fucking boring damn long. It’s a moronic book that just echos his master’s voice in a megaphone - just b.s.

[Scott Cederberg · Rating 2 out of 5]

While this book fanned the flames of a brief obsession with Larry Ellison, it was overly fawning and did not provide much insight into the reasons for Oracle's business success. I suppose I got what I deserved for reading a book whose cover quotes reviews marveling at the "access" obtained by the author.

[Krithika · Rating 3 out of 5]

Silicon Valley has a tendency to forget even recent history, so it was fascinating to see the parallels in leadership, marketing, and competitive dynamics just a few decades ago. Selling enterprise software never seems to change. That said, the rest of the book was dull, unendingly detailed about unnecessary areas, and failed to paint a clear portrait of its subject.

[Michael Siliski · Rating 3 out of 5]

An interesting, though bloated, portrait of Larry Ellison and Oracle.

Really in need of a good editor to cut the length in half and give it some structure. The business parts—technology, strategy, and management—are fascinating, but highly repetitive. There are interminable meetings that are basically all carbon copies of each other, with Ellison explaining yet again the benefits of centralized databases and unified business suites. I recall at least three times Ellison telling some story about how shipping software is like childbirth (a lot of pain, but after you have this beautiful new baby)… okay fine, but one time would have gotten the point across.

The non-business parts: personal life, bigass yacht stuff, Ellison’s $100M house in Woodside, family life, are not super interesting, with the exception of the harrowing tale of the Sydney-to-Hobart race in 1988. They feel like obligatory biographical details, and could have been dealt with in 80% less detail while still communicating what they have to say about Ellison personally. (And he is one interesting dude—vain, brilliant, ruthless, materialistic, technically strong, often strategically brilliant and sometimes way off, an incompetent manager, etc.)

I wouldn’t recommend it unless you have a particular interest in Ellison and Oracle.

[Ryo Ishizuka · Rating 4 out of 5]

8/10: Softwar reads like a 500 page HBS case study.

Over the years, many have chronicled the rise of tech businesses like Facebook, Amazon, and Apple. However, very few have focused on enterprise software. It makes sense. B2B is inherently less relatable. It’s hard to get an average American riled up about API integrations.

This book will certainly reasonate with those in tech biz dev, investing, or consulting. Symonds dives deep into everything from
-Biz model evolutions from mainframe, client/server, and the internet.
-How to cross-sell from databases to apps
-What a bad sales culture looks like
-Why system integrators screw up implementations

Softwar has an interesting format. Symonds, a former writer at the Economist, documents the day to day at ORCL. Interestingly, Lary Ellison also provides unedited commentary. This often creates juxtapositions in which Ellison pours the Oracle Gatorade, while Symonds gives a more somber look.

I enjoyed the book. But it’s certainly not for everyone.

[Titiaan · Rating 3 out of 5]

I picked up this book because it was mentioned by John Collison in an interview. It's a portrait of Oracle written around the turn of the millenium.

I found it quite interesting to read about the positioning that Ellison took about the business problem of siloed data. The same positioning can still be seen today with companies like Snowflake.

I also enjoyed some of the detail around a typical day and week for Ellison, and how he'd show up in meetings.

I stopped the book roughly halfway through as I felt I had gotten most of the gist.

[Brunoob · Rating 3 out of 5]

The structure doesn't make sense, and the psychological analysis of Larry Ellison comes too late. Somewhat boring at times. But it's good to learn that one can make so many mistakes and still build a company as successful as Oracle.

[Andrew · Rating 4 out of 5]

Very good read if interested in the history and drama of the software business. The commentary by Ellison was elucidating and entertaining. It was repetitive in the second half and would have been better if it were 100 pages shorter and had an update 10 years after initial publication.

[Dr. Chadi Saba · Rating 2 out of 5]

I couldn’t finish the book. I was expecting a biography of Larry, but this book isn’t really one. However, I liked the idea that Larry commented on many events; this gives us multiple points of view on the same event.

[Nicholas Moryl · Rating 3 out of 5]

I never want to read the phrase “best of breed” ever again.

[Nick Tommasini · Rating 3 out of 5]

2.75 - interesting enough owing to its subject but highly disorganized and overly biased towards ellison

[iKasonde · Rating 5 out of 5]

A Good Read

I really enjoyed the book and would definitely love to an updated version that builds upon and has transpired in the last 22 years

[Ben · Rating 4 out of 5]

Fascinating to see how many dynamics in software have happened before.

[Ethan J · Rating 3 out of 5]

founding history of oracle was interesting about his vision

[Suraj Srivats]

Joe Oleynik (1/2/26)

[Despoina · Rating 3 out of 5]

It's definitely an interesting story, but the narrative is non existent. Most of the time, it felt as if I was reading the authors notes. Lots of repetition, revisiting the same events without adding anything to the story. Also, we learnt very little about Larry Ellison,and a lot about oracle and how to make software. Very disappointing reading, especially coz it's 500 pages long

[Kevin · Rating 4 out of 5]

If you're in the software business, this is a must-read. This book was last updated in 2004, which makes it very dated given the breakthroughs and changes over the past decade, but in a way that makes it even more interesting. A lot of Ellison's predictions - particularly about software-as-a-service and the Internet as the dominant backbone for business applications - were spot on. His belief and foresight about the relational database as a commercially viable enabler for organizations was prophetic. The world of software, technology and data would not be where it is today without the advancements in the database that Oracle and Ellison relentlessly built. His other prediction that only a few large integrated software vendors would survive was disproven by his own investment in Salesforce, a CRM vendor that's now the 4th largest business software company in the world by revenue. Even more interesting was Ellison's distaste of acquiring your way to growth. He thought not buying other companies and focusing on keeping their tools integrated was critical. But after this book comes out, what does Oracle do? They go on a shopping spree. Peoplesoft/JD Edwards is briefly covered in the book, but Oracle would go on to buy CRM vendor Siebel, go into the hardware business through buying Sun Microsystems, buy HR app vendor Taleo, and others. Do all these tools work together? No. So did Ellison change his tune personally on acquisitions? Or was he forced to because that's what happens to mature companies when they're near the top of their market? Symonds' book will trigger a lot of questions like these, and they're questions worth asking in the business world.

[Keith Brodhead Jr · Rating 5 out of 5]

OMG!

I work for Oracle and I'm amazed and thrilled to be led by Larry Ellison. I now understand how the culture developed.

[James Gingerich · Rating 5 out of 5]

If you have ever worked with Oracle or competed against them; this book is a must read. It captures the competitive spirit of Larry Ellison and the resultant culture of his firm. The book highlights the "Perfect Storm" of Oracle's infamous encounter with the State of California and details Ellison's gamble in shifting the company from a vendor of client-server software to the E-Business Suite. Whether or not Symonds intended to draw analogies between Ellison's yachting "hobby" and his business pursuits it makes for a very interesting read.

After reading about Oracle's battles against Microsoft you can't help rooting for Ellison and his warrior leadership style.

As a salesperson in the software industry I found it a great read!


James Gingerich
Sr Partner Account Manager
Sybase

http://www.linkedin.com/in/jamesg2006
http://softwaresalespersoneducation.b...

[Sam · Rating 3 out of 5]

"I was most interested in the information on Oracle and Larry's theories on computing. This was dominant in the book, though it wasn't complete. I think I'd like to find a less complementary biography to balance this because I thought the author seemed more than friendly with him. I'd also like to find an update to cover the last 5+ years since the book was printed. For example, I know that the PeopleSoft and Seibel purchases have happened since then, and I'm curious on his take on why these were good for Oracle and his business when he seemed so critical of their business model. Overall, it was interesting, and I generally enjoyed most of it."

[Davis · Rating 4 out of 5]

Great biography on Larry Ellison. I've worked in the IT industry for over 10 years some of which focused on implementing software packages. I've seen Larry give keynote speeches and usually came across as an arrogant, self-righteous person. However, after reading this book and contemplating his ideas for the software industry, I now understand his actions and consider him to be one of the geniuses of the industry. At times the book comes across as a sales pitch, but at least it is a very convincing sales pitch. He definitely has a very interesting life.

[June Ding · Rating 4 out of 5]

A surprisingly very good book, not because it reads well ( not as great at story telling as many of the biographies I read), but because the insight it offers about Ellision and how he made those revolutionary decisions. It feels real and so relevant even though the book was written more than 10 years ago. What Ellison sai'd and believed at the time have been proved so right, which proves him a true visionary. What also amazes me is that throughout the book you read him readily admit his mistakes, all the time. That says something about success .

[Marc · Rating 4 out of 5]

Working for Oracle makes this book not mandatory to read, for sure. However, I was surprised how it helped me to understand business strategies of today. This book gives an autobiographical insight as well, but not more than I expected.
In my point of view the editor sometimes seemed to be too dependant and is lacking to be objective. But overall reading this book was a pleasure due to the unique live comments and footnotes of Larry himself.

[Mark McGranaghan · Rating 4 out of 5]

A surprisingly interesting look at the life and work of Ellison. Not the person I expected.

The book benefited from Symonds' close access to Ellison. One could not have written this book well from a distance.

Unfortunately the book is getting out of date. It's 10+ years old now, a long time in the industry.

[David Flynn]

terrific meandering read on Larry

I mean, I really enjoyed it, but maybe an editor could have helped. Not sure I needed the blow by blow on that much sailing, but the business stuff was terrific.