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Books

Softwar: An Intimate Portrait of Larry Ellison and Oracle: Software companies that sell to businesses can have crazy nonlinear changes in valuation, where VCs decide that they're worth 50x or 100x revenue. That kind of bet can work when investors have a good model of where software fits into an existing stack, how it can be priced, how it gets sold, etc. Softwar is, basically, a book about how that knowledge was won.

Like many novels, the book opens in media res and then tells the rest of the story in flashbacks. We begin with Larry Ellison rushing from one meeting to the next, flogging his latest software suite, while tech spending collapses in the wake of the Y2K spending burst and the end of the dot-com bubble. It sounds stressful: at one point, two executives at an Oracle client company realize Ellison is traveling in their general area, so they hop on the company jet to tell him in person how peeved they are about the quality of Oracle's latest release. Ellison's messaging in this tour is interesting, because Ellison's big themes are 1) you should not be hiring lots of systems integrators to customize Oracle's products (and, coincidentally, take money out of your budget for buying Oracle), and on a related note 2) you shouldn't buy software customized to your business practices, but should instead customize your business processes around the software. Which is all incredibly self-serving, but also in a sense true: if you can squash the marginal cost of sending information or executing simple rules to roughly zero, that completely changes what your company ought to be good at.

The backstory is one of a company that was both technically strong and incredibly good at sales, but occasionally not great at managing cash flow; they had a near-death experience in the early 90s where they almost ran out of cash (and, as a nicely literary premonition, this started right around when one of their brand new incentive programs was paying some sales commissions in gold). But they managed to survive that, get back to growth, and expand from databases to ERP to CRM to everything else. The stretches that take place in the 90s ought to be a relief to anyone at a high-growth company right now, because Oracle is described as completely chaotic, full of corporate infighting fueled by weird grievances, and run by a CEO who's occasionally checked out to focus on yachts, mansions, etc. And yet, everyone does well; even the people who lose out in corporate knife-fights end up with a big pile of stock options, even if they have the strange habit of getting suddenly fired right before another tranche vests.

(Conspiracy-minded readers will be delighted to know that not only was Oracle's first customer the CIA, and "Oracle" was actually the code name for an internal CIA project. They also mention that the first big customer category was other intelligence agencies, including the NSA. The less conspiratorial read is that of course the government needs database software, and during the Cold War they tended to be more tech-forward. And if you're trying to create a company with state-compatible backdoors, you probably want to give it funding through front companies and you definitely want to coach the CEO about the importance of not blabbing about all of his intelligence ties to friendly corporate biographers.)

Ellison does produce some notable wisdom about selling complex software packages to big customers. One of the interesting ones is his claim that analysts and the media tend to like whichever product is growing fastest, and if you're dependent on client demand and on integrations with other products, you need that endorsement. So, better sales and marketing can actually make a product better for customers even if the product itself doesn't change. This has some explanatory power, for better or for worse.

The book's style is unique. Ellison is clearly a fan of deals as well as technology, and his arrangement for the book was that he cooperated with the author but got the right to include his own footnotes. This means he gets the last word every time one of his former colleagues complains about his behavior. And it gives him the opportunity to vociferously deny that he would ever wear a pink tank top ("This is very important," he explains). So you're getting a rough draft of text history, annotated by one of its most important players. A lot has changed since the book was published in 2004 (though Ellison doesn't seem to have aged much). Softwar shows how that change happened.

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