September 12, 2005 1:23 PM PDT

Siebel and Ellison: Software's odd couple

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Steve Jobs, and he was an active supporter of Bill Clinton. Perhaps the only difference between Ellison and Gatsby is a noticeable lack of a ruinous Daisy Buchanan in his life. The playboy adventurer is now on his fourth wife.

Meanwhile, back at the ranch
Siebel, on the other hand, has eschewed the limelight. Like Ellison, the 51-year-old is a licensed amateur pilot and is famously competitive. He's also rich. Siebel made it into the Forbes list at his company's peak and stands to become even wealthier, thanks to the Oracle deal. But he's a major donor to the Republican Party who was regularly hobnobbed with Republican powerbrokers like Marc Racicot, a Siebel board member who three years ago was appointed head of the Republican National Committee.

Siebel has also studiously avoided Ellison's flamboyance. While Ellison tends to stay inside an executive suite, replete with a jewel-encrusted statue of Buddha that's hundreds of years old, Siebel preferred to rub elbows with his employees, often eating lunch in a corporate cafeteria side by side with engineers. The only real indication of wealth in his office was a William Alexander Coulter painting of the evacuation of San Francisco after the city's 1906 earthquake and fire.

Siebel routinely told reporters in interviews that they could ask him anything, but even the most innocent of questions about his family were off-limits. Still, he was embarrassed by press reports three years ago that he threw, at his own expense, a lavish birthday party for his wife in Puerto Vallarta, Mexico, just as his company was running into trouble.

While Ellison revels in being a Silicon Valley celebrity, by many accounts Siebel prefers to keep to himself. He's an avid golfer and these days spends much of his time on a sprawling ranch in Montana. Siebel worked as a ranch hand for a brief time after college and often said that relaxation to him was doing the hard ranch work you don't find very often in corporate offices.

The childhoods of the two executives were different, too. Although they both grew up in Illinois, Ellison was raised in the blue-collar south side of Chicago and is famously a college dropout. Siebel was raised in a comfortable Chicago suburb, attended military school and actually graduated from college. He even has an MBA.

Still, despite Siebel's aspirations, his company and Oracle weren't all that different. Both had extremely aggressive sales forces headed by executives whose personalities were inseparable from the companies they created. Culturally, analysts say, it's not as bad a fit as some would think.

But it's hard to imagine that Oracle, as massive as it is, thanks to its recent acquisition spree, is big enough for both the personalities of Larry Ellison and Tom Siebel.

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