After returning from the Sydney to Hobart Yacht Race to the Oracle campus in suburban Redwood Shores, Calif.--an almost surrealistic contrast to the ravaging seas of the South Pacific--the swashbuckling chief executive began to think of more practical consequences of his adventuresome ways.
Who would run the company he co-founded if something were to happen to him?
That question--as well as speculation as to who is running the $200 billion database powerhouse right now--has been a topic of conversation throughout the high-tech industry ever since longtime No. 2 executive Ray Lane abruptly resigned in June. Sources told CNET News.com that Lane had essentially been pushed aside as Ellison decided to reassert his leadership in a bid to transform Oracle from a traditional software manufacturer to an Internet company.
Lane has moved on, having joined the powerful venture capital firm Kleiner Perkins Caufield & Byers. But back at Oracle, the void created by his resignation has given rise to a new round of internal sniping, political jockeying and concerns among investors over one of the most important companies in the global technology arena.
The question of who might be Oracle's next chief executive is anything but clear. Many sources close to the company believe that, regardless of titles, Ellison will remain firmly in control as long he stays with the corporation.
"Larry has divided Lane's former responsibilities with people who won't argue with him," one former Oracle executive said. "All decisions run through Larry. He's calling all the shots."
But he can't run the company alone--and Oracle, like so many other large corporations, has no shortage of ambitious executives vying for a place by his side. What has emerged is a small circle of three high-level players who are perceived to be running the company on a daily basis, always under Ellison's watchful eye: Gary Bloom, executive vice president of the system products division; Safra Catz, executive vice president of business practices; and longtime chief financial officer Jeff Henley.
It is an odd mix, even for a company with Oracle's controversial history. Bloom is widely viewed as an ambitious but meat-and-potatoes kind of executive, a solid department head yet far from a visionary. Catz is a relative newcomer who sources say has quickly become a confidante to Ellison despite her short tenure. Henley is a classic numbers guy, a trusted officer who has kept Oracle's finances on track for many years but not someone to lead the charge into battle.
None of the three agreed to be interviewed on the record for this story, but several former executives and other sources familiar with the company say the troika had been increasingly assuming control of the company as Lane's authority waned. At the same time, none appears to have a strong command of all aspects of Oracle's far-flung operations. And that, sources say, has been structured intentionally by Ellison so that only he can maintain full control.
"A CEO has to be able to think for themselves and make decisions," another former executive said. "And right now, there are no such people at Oracle."
That line of thinking particularly applies to Bloom, according to many who know him, and helps explain his rapid rise from relative obscurity.
Bloom, who joined Oracle in 1987, spent nearly a decade toiling away in the less glamorous divisions of the company, current and former executives say. At a time when Unix was hot and Microsoft's NT was gaining momentum in the corporate software market, Bloom was assigned to the task of getting Oracle products on IBM mainframes.
"Gary had all the backwater products. He was a good solid journeyman but wasn't bursting with a lot of ideas," a former employee said. "Gary is colorless. He's very process-oriented and is better suited to minding the shop."
But other former executives note that Bloom has one of the strongest relationships among development managers when it comes to working with Ellison.
"It was clear Larry had a lot of respect for the guy. Gary often joined us when we held meetings to discuss our product advertising," said Zack Nelson, chief executive of MyCIO.com and former Oracle vice president of worldwide marketing. "It was real unusual for product development managers to get involved with advertising, but Gary was a key driver of some of the content we used. Larry is a creative guy on the copy front, and Gary contributed a lot of excellent copy."
Bloom's rise has been conversely related to Lane's decline. Bloom saw his responsibilities grow to include marketing and got more exposure throughout the company by attending various events. On a business trip to Japan a couple of years ago, the head of Oracle's Asia operations even introduced Bloom as the company's next heir apparent, sources said.
Today he oversees a large chunk of Oracle's operations, including system software products, marketing, business development, venture funding, support, education and the company's partnership program. Still, while Ellison is believed to have at one time leaned toward Bloom as his successor, that support seems to have waned.
Few believe that he would be allowed to run the company alone. Even if Bloom were given the chief executive's title, sources speculate, Ellison would continue running the show.
"Gary is good at executing what Larry wants done. And right now, Larry wants those kind of people," a former executive said. However, the source said, "the prospect of Gary being the future CEO died about a year ago."
If Bloom has become Oracle's main salesman, Catz has become its de facto chief of staff.
Joining the company only last year as senior vice president, Catz was promoted about six months ago and has acquired more responsibility and influence ever since, current and former executives said.
Though not apparent to most at the company, some senior executives said the signs of her sway with Ellison were evident from the start: Her office was placed within the confines of Ellison's spacious 11th-floor suite, allowing the two executives to work within sight of each other, sources said.
Lane, who served as president for four years before his resignation, had to settle for an office across the hall from the CEO suite. Henley, who has served as CFO for the past nine years, had an office five floors below.
"She came in as an SVP, and the dynamics between her and Larry was clearly that he trusted her and wanted her to trawl through the information given by others to challenge it," a former executive said. "It was a bit awkward, as she didn't understand the business and was challenging some of the old icons."
Catz joined Oracle about the time the company was establishing its new budget last year. As she sat in the meetings, she voiced strong concerns about reducing costs.
"Jeff (Henley) had been saying the same thing for years," a former employee said. "He would say we had to pay attention to profit margins and costs. But Larry didn't pay attention to it until Safra came aboard. Once she arrived, they started looking at ways to cut costs and set the $1 billion savings out as a goal. The budget meeting was run more by Safra than Jeff, and it seems she was diminishing his role."
Eventually, Henley got used to her participation in financial matters. "Safra's like the chief of staff, and (Henley) is like the U.S. Treasury secretary," one source said.
Wall Street analysts such as Morgan Stanley Dean Witter's Chuck Phillips agree that Henley's place is secure. "Of all the Oracle executives, he has the most credibility on how things are developing," Phillips said.
Catz's assertive nature has been noticed in other areas as well. Sources say that she tends to be more aggressive in speaking her mind than Bloom is at meetings and is less likely to automatically defer to Ellison.
Regardless of their differences, those inside and outside the company say Catz, Bloom and other high-ranking Oracle executives may have a short period in which to prove themselves, given the blistering pace of technological change and Ellison's mercurial nature.
As one former executive said of Ellison: "He's supportive of certain people at certain times--and then it takes a turn."