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After Meg Whitman’s exit, Uber’s CEO search is down to only male candidates — as its board struggles and Travis Kalanick meddles

  • As Uber searches for its next CEO, some directors worry ousted chief Travis Kalanick is trying to game the outcome in his favor
  • That follows the exit of Hewlett Packard Enterprise CEO Meg Whitman from consideration to lead the ride-hailing company
  • Sources with knowledge of the situation said the group of four final candidates being considered are all men and all CEOs
Uber CEO Travis Kalanick.
Shu Zhang | Reuters
Uber CEO Travis Kalanick.

Warring factions within factions, conflicting back-channeling, intense media scrutiny, questionable foreign influences and a capricious leader whose jarring moves leave everyone in a state of perpetual uncertainly.

The Trump administration, right?

Well, yes, but also Uber, as it nears its much anticipated decision on who will be its next CEO.

And, according to sources, that top leader is not going to be a woman, as the board of the car-hailing company struggles to move forward.

To add to the drama: Some directors worry that its former CEO Travis Kalanick — who was ousted — is trying to game the outcome in his favor, after he told several people that he was "Steve Jobs-ing it." It is reference to the late leader of Apple, who was fired from the company, only to later return in triumph.

That's why, while I am always loathe to dump a kitchen sink's worth of reporting in one story, it's hard not to since this particular pile of dirty dishes is so stuck together that it's almost impossible to pry them apart at Uber.

"If there was no hair on this dog, this would be a no brainer for anyone to take this job," said one person close to the search of Uber's next leader. "But this is the hairiest company anyone has ever seen."

Ew. But pretty much true.

So, in what is probably a vain attempt to clarify the situation, here's the state of what is a very confused play:

Boys club

With the exit of Hewlett Packard Enterprise CEO Meg Whitman from consideration, several sources with knowledge of the situation said the group of four final candidates being considered are all men and all CEOs. (Also: Only one of those is a person of color.)

Among those choices is outgoing GE CEO Jeff Immelt. But Immelt is not, said several sources, the top choice of several members of the search committee and also within Uber's top ranks. Some are worried that — while he is obviously a very experienced manager — he lacks the entrepreneurial drive to take the company to the next level.

In other words, he's too much a corporate suit and not enough a geek pirate. (Anywhere else but in tech, this is not seen as a bad thing, but here we are.)

Immelt aside, sources said that the inclusion of more women in key decision-making roles at Uber will come via the addition of more independent board members and top execs rather than as its main leader.

That, of course, will be a major disappointment to some, especially given major problems at Uber involve sexism and sexual harassment. While gender of a leader should not matter to dispatching such appalling behaviors, the symbolism over the appointment of a female CEO at Silicon Valley's most toxic-bro startup is unquestionable.

But there are also not that many top women CEOs to pick from. Execs like Facebook's Sheryl Sandberg and General Motors' Mary Barra were not interested, said sources, and others pursued, like EasyJet CEO Carolyn McCall, did not pan out.

It had been hoped that the decision on who will be the next leader of Uber would be completed within the next week, but trouble getting the board to coalesce and trust each other has and continues to complicate the effort.

In addition, sources said the not all board members had met all the top candidates as of this weekend, so that no vote on any one of them had been planned or is planned immediately. (Uber's board now meets regularly every two weeks, so that could change.)

That lack of cohesion impacted the courting of Whitman, which never resulted in any vote (and which had never been scheduled at all, despite one report that it was). This was largely because she had not met with all directors before she suddenly pulled her name out of consideration late last week.

Sudden indeed. Whitman was expected this past weekend to meet in person with more directors, including Wan Ling Martello of Nestlé and Arianna Huffington, which never happened.

Whitman out!

Whitman's departure from the Uber fray was considerably more complicated than has been previously reported. The well-known exec, who is also one of the most prominent women leaders in tech, was indeed interested in the job. That included having several substantive discussions with directors, where she made a series of suggestions on how to fix Uber.

Still, sources close to Whitman said she was never formally offered the job by Uber's board, even though she certainly was intrigued by the possibility.

And why not? Such a role would have been the capstone of a long and largely successful career, most especially in growing eBay to its heights from a small startup. Turning around Uber and taking it public would have been the ultimate addition to her legacy.

But board disagreements, worries about whether all the myriad of problems at Uber had surfaced and concerns about the continued involvement of Kalanick, as well as the public disclosure of Whitman as a possible candidate, ended that possibility.

"Uber's CEO will not be Meg Whitman," she tweeted on Thursday, days after media reports on Tuesday by Recode and Bloomberg that disclosed Uber's interest in her. That then put pressure on Whitman, a situation made worse by another report in Axios that indicated that she was not a unanimous choice of the board.

Such mishegas irked Whitman, who expected a more — ahem — professional process. "What a mess," said one person. "Why should she get dirtied by their playground antics? It's like a sandbox over there."

Well, to be fair, more like a really nerdy version of "Game of Thrones," with 100 percent less dismemberment but 53 percent more intrigue.

Still, as Recode previously reported, Whitman was an early investor in Uber and has helped out with coaching from time to time, especially with Kalanick, so she did have some familiarity with the unusually juvenile management style there.

But sources said she did not like the process, and gave the board a 48-hour deadline to decide if they seriously wanted her to be CEO. While some on the board wanted to move forward immediately, others — Huffington, for example — did not since she had not met them all in person.

"It was artificial urgency, even if Whitman might be the right choice," said one source.

No matter! Whitman out!

We have to talk about Travis

That might not have mattered, as Whitman was also worried more specifically about further disclosures to come from the company related to its lawsuit with Alphabet's Waymo, especially how involved Kalanick was in the allegations leveled against Uber.

"Who knows what could fall out that the closet over there?," said one person, reflecting the concerns of many candidates who have spoken to Uber, including Whitman. "There could be even more skeletons."

Kalanick's continued role figures large in the every person I spoke to who has been contacted about the CEO job.

What's the biggest problem at Uber?, I asked.

"Travis," said one

"Oh, Travis," said another.

"Man, he's brilliant and so important, but who wants to deal with Travis?," said yet another.

If that sounds like a real sad country song, titled "The Travis Blues," you are not far off the mark.

This was certainly not the plan when Kalanick was dispatched to Tahiti to sail around a glamourous yacht — owned by media mogul Barry Diller, with fellow guests like CNN's Anderson Cooper — to cool after he was forced out at Uber.

He initially had agreed to take just a temporary leave, a move that became permanent after a group of key investors — including Benchmark — demanded his full departure a week later.

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But once he returned from the South Seas, his ardor for meddling in the company did not end. According to numerous insiders, the pugnacious entrepreneur has continued to try to involve himself in daily operating decisions, so much so that top execs have been mulling how to get help from the board to rein him in.

"It's not stopped," said one top exec about Kalanick up in the grill of the operating group that is running Uber. "None of us know what to do since it is Travis."

In addition, to cut off Kalanick's access, the Uber board has reinforced a policy that all directors get the same limited access to information about Uber's ongoing operations. "We have had to put guide rails on him," said one person involved. "Even if he keeps trying to break through them."

Indeed, Kalanick was considered by many directors and investors to be obstructive to the process of finding a COO before his departure as CEO.

And there have been more signals that he has been unhappy about this status. Since he left, Kalanick has told numerous people, including at least one job candidate, that he was "Steve Jobs-ing it," an apparent reference to the purge and later return of the legendary Apple founder at the company.

(As I have said before, I knew Steve Jobs, Steve Jobs was a person I wrote about and — you got it — Travis Kalanick is no Steve Jobs. But I digress!)

But the key tenet in this comparison is that the tarnished tech hero leaves the scene to wander in the desert for years before the triumphant return. Instead, what has been described to me by many is an entrepreneur who cannot let go and, in fact, has been trying to plot ways to increase his grip.

Why? "If you think about it, Uber has been his life and it's only more so with his terrible personal situation," said one person, who is fond of Kalanick, referring to the recent tragic death of his mother and the serious injuries sustained by his father in a boating accident. "Giving up Uber is not easy."

As the board turns

And being with each other in a cohesive manner is not something Uber's current board seems capable of either, given all the odd back-channeling and frequent miscommunications that seem to crop up.

While there was a recent dinner at San Francisco's Garabaldi's restaurant that included Huffington, Ling and two other Uber board members, TPG's David Trujillo and Benchmark's Matt Cohler, to try to create some level of comfort, there is a lot to repair.

Here's a clue to how much: The continued media leakage from the CEO process. While this is not completely uncommon — the Microsoft CEO search got a lot of ink — what is unusual is how varying the accounts of the same meetings or circumstances are at Uber. In fact, they are often diametrically opposed to each other.

This is something that many who have been in touch with Uber have experienced. "Consensus is not something you are feeling is happening there," said one person, which makes every possible move seem suspect.

(Have to seen the really complexly plotted spy thriller "Atomic Blonde," where everyone seems to be lying and then lying about lying? Uber is more confusing.)

That's why a recent attempt to discuss a funding offer involving both secondary sales and a new investment from Japanese investor SoftBank has been so riven. While I will not get into the particulars in this hairball of a story here — unless you really want to hear about transfer restrictions, tender offers and more right now — suffice it to say that it has turned into a drama about whose side SoftBank leader Masa Son will land on.

Let me be clear, this is before any investment, which really should not take place without the cooperation of the new CEO, even if there is some urgency in making sure SoftBank's $100 billion fund does not favor only Uber's rivals. Since it just made a big investment in Southeast Asia's Grab, many at Uber remain fretful.

Also, a related cause of tension was a Bloomberg report that Benchmark was mulling selling all of its 10 percent stake in Uber to SoftBank, which sources said was not true. While the venture firm might sell some of its stake if any transaction takes place, sources said Benchmark was wary that such a story was meant to weaken it.

That might not be so far-fetched given the deep tension between Benchmark's Bill Gurley — who left the Uber board in favor of his partner Cohler — and Kalanick and the level of mistrust that has developed over time.

"Every single act feels like it might have another meaning," said one person familiar with the situation. "Even if it does not."

What is all boils down to is the deep concerns around control of Uber's fate: Who has it and who is angling for it.

That distrust has left the board at times in a kind of odd face-off that appears to be more perception than reality, once you really plum the depth of the concerns.

Consider the possible return of Kalanick as CEO, which most will finally admit is overblown unless he decides to go full throttle and end up in a legal fight with the company he founded. In reality, without the support of board members Ryan Graves and Garrett Camp, Kalanick has none of the kind of leverage than has been reported.

"Travis would have to blow it up completely to get his job back," said one major investor, familiar with the cap table of Uber. "And maybe he is crazy enough to do that, but he'd better bring a lot more ammo."

What I can say for sure is that the entire company is leaking like sieve and that the Trump White House has a tighter press ship. Which brings us back to the beginning — if Uber wants to move forward, it had better lose that meme and get back to building the kind of company its employees so desperately want to.

Said one of those top execs to me tonight: "When is this going to stop, so we can do our jobs?"

It's a very good question for the Uber board. Whether they can do their only real duty as directors — hiring a CEO — and make that happen soon is unclear.

One silver lining: Anthony Scaramucci is currently busy with another gig.

By Kara Swisher, Re/code.net.

CNBC's parent NBCUniversal is an investor in Recode's parent Vox, and the companies have a content-sharing arrangement.