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Four key questions that will shape the outcome of Uber’s latest financial mess

Use these as signal in a whole lot of noise.

SoftBank founder and CEO Masayoshi Son at Sun Valley Conference in Idaho
SoftBank CEO Masayoshi Son
Scott Olson / Getty

Tension in Uber’s upper ranks have already ricocheted to every corner of the company. An early investor has sued ex-CEO Travis Kalanick just as he tussles with the board over the search for his successor. Meanwhile, deep-pocketed suitors are circling for a piece of the $70 billion startup.

We know Uber is in advanced talks with a consortium of investors as part of a deal that would allow some early backers to cash out and could resolve some of the stewing and have enormous implications for the company’s future.

But there are questions hovering over the behind-the-scenes bargaining.

Who is the seller?

Perhaps no question is more dominant right now than which company exactly is going to sell its ownership in the most valuable startup in the world. The long-presumed seller is Benchmark, which stands to make a killing no matter how this story ends, but it’s leaning against selling any of its stake, according to sources.

The uncertainty surrounding Uber’s future makes it an attractive time to exit. But while it’s unlikely that an institutional investor like Benchmark would vacate its entire position, the pressure for them to do so from some Kalanick loyalists — and fellow investors — is real.

But the typically understated venture firm has dug in its heels and claimed publicly it is “long” on the company. So who else is ready to take chips off the table? That, of course, depends on the price, which is still being worked out by Goldman Sachs. Some in the talks believe that a pool of earlier investors, eager for liquidity, could jump if the payday is big and certain. But no savvy negotiator would raise a hand this early.

What is Benchmark thinking?

Benchmark’s decision to launch an aggressive lawsuit has already spooked rising entrepreneurs, divided the board and is not unanimously supported by Uber investors — even those who don’t like Kalanick much. The suit is unprecedented in recent history, and their ultimate goal isn’t clear.

Which is a higher priority: Changing Uber’s governance, or extracting the highest possible price for their shares? Benchmark has argued that it is pursuing the former to achieve the latter — that the company is too promising to let Kalanick interfere with its future. But would Benchmark be willing to sell its position — weakening its influence and perhaps emboldening Kalanick by selling to a buyer friendly to him — if the price rises? And is Benchmark actually preparing to go to court if it doesn’t get its way, or is the litigation just another bargaining chip that can be traded away?

What is SoftBank’s price?

We reported over the weekend that SoftBank, the monstrous Japanese investment fund, had originally been thwarted by Benchmark when it sought to buy Benchmark’s shares at a mere $45 billion valuation. It was beginning to “make the rounds” and talk to potential buyers — not yet to raise the offer.

Then this new constellation of groups emerged — led by Dragoneer Investment Group, General Atlantic and others — that briefly complicated any deal. The relationship between the players, for now, is described as friendly (Will that last?), but few expect any deal of scale to happen at such a low secondary valuation. The $45 billion number could just be the start of negotiations, but SoftBank is eager for a deal. For existing investors, this raises bigger existential questions about the impact of the last six months: How much of a haircut do they think their company merits after all the drama? If there’s too much of a perception gap on that question, this deal could fall apart fast.

What is Shervin thinking?

One last obstacle could be the protestations of Shervin Pishevar, Kalanick’s longtime ally and at one point a board observer. Pishevar is arguing that Benchmark should sell 75 percent of its position — and claims that he has investors at the ready to buy the shares. Who, exactly, would be able to front those billions of dollars? Who knows.

Even people close to him do not seem to quite understand his master plan. It’s possible that Pishevar could find himself aligned with the SoftBank contingent, especially if Benchmark sells some of its stake. (Benchmark is said to be not interested in selling directly to him.) But more broadly, Pishevar’s strategy seems to be to muddy the waters with explosive allegations, the most recent of which was sent to the board on Tuesday evening. If everyone is acting improperly — Benchmark, Chris Sacca, Lowercase Capital — then maybe Travis Kalanick doesn’t look so nefarious after all.

Correction: an earlier version of this story incorrectly named Arianna Huffington as a target of Pishevar’s letter.

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