How former Uber CEO Travis Kalanick could actually make a comeback

JP Mangalindan
Chief Tech Correspondent
This may not be the end for Travis Kalanick’s tempestuous relationship with Uber. (Source: Evan Agostini/Invision/AP, File)

Could ousted Uber CEO Travis Kalanick actually make a comeback?

The 40-year-old serial entrepreneur seems to think so. According to a Recode report earlier this week, Kalanick plans on “Steve Jobs-ing” it, a ballsy reference suggesting he plans on working at Uber again one day. If so, the move would mirror Jobs’ own professional trajectory: being ousted from Apple (AAPL) in 1985 and returning 12 years later to the ailing company as chief executive.

Several sources Yahoo Finance spoke to, who know Uber’s co-founder, conceded a comeback was a longshot, but not out of the question.

“I don’t think he’ll be able to come back unless he has some sort of reconciliation with the community, a mea culpa that promises to fix the issues and not just lip service,” one Uber investor told Yahoo Finance. “It has to be a genuine thing.”

“Travis has a lot of support inside of Uber,” the Uber investor added. “There are a lot of people who think he fought hard, was doing a great job, and the company is really rudderless without him. It would be in a tough spot without him. Many on the team want him back. I think the people who know him internally want him back.”

Another acquaintance of Kalanick’s, Brian Solis, principal analyst at the San Francisco-based research firm Altimeter Group, suggested Kalanick could come back after a period of time passes. The former Uber CEO should also consider some public moves that demonstrate his personal growth and evolution outside of the context of Uber, just as Jobs did with the now defunct NeXT Software. (Apple acquired NeXT for roughly $400 million in 1997.)

“Steve Jobs, too, was not without his issues in that people felt he was incredibly harsh and blunt, and I think that’s par for the course in that all leaders have things that rub people the wrong way,” Solis explained. “No one questions that when companies are doing well. Travis is arguably someone who adds value to the company.”

If that’s actually the case, perhaps time away from Uber may be Kalanick’s greatest asset — provided the hard-charging Kalanick can stay away.

The sexual harassment is damning

While two sources told Yahoo Finance that Kalanick still has a lot of support inside Uber, his mishandling of scandals chipped away at his — and in turn, Uber’s — standing with drivers.

In fact, drivers continue to complain over issues such as low wages, while some passengers remain dissatisfied by revelations around Uber’s turbulent workplace. That’s despite a 15-minute presentation in July in which Uber executives told shareholders to expect increased passenger bookings and narrower losses moving forward.

Thrive Global Founder and CEO Arianna Huffington, who’s an Uber board member, speaks during the Women in the World Summit at Lincoln Center in New York, Thursday, April 6, 2017. (AP Photo/Richard Drew)

One venture capitalist who knows Kalanick also said that a comeback, while possible, could hurt Uber’s value proposition. Kalanick’s neglect of Uber’s work culture and single-minded focus on rapid global expansion enabled the very bro culture where male employees allegedly harassed female colleagues and got away with it (for a while, at least). Meanwhile, the contentious legal battle over trade secrets with Waymo could cost Uber a lot of money if the lawsuit goes to trial and a jury rules in Waymo’s favor. Kalanick’s association with those scandals, at least in the short-term, would continue to be a liability for Uber as it attempts to navigate its way out of a rough period.

“The sexual harassment is damning,” acknowledged the venture capitalist. But was this venture capitalist surprised once the scandals came to light? Not exactly.

“Travis is wizzywig as much as anyone I’ve ever worked with,” the venture capitalist explained. “He has one gear: all-out hyper-aggressive. Like all of these new startups, or like every company, they’re built in the founder’s image. And Uber is, you know, all about [achieving] world domination yesterday.”

Certainly, there are several notable examples of hard-charging tech CEOs who came full circle. Jobs himself is perhaps the most famous example. After being ousted from his position running Apple’s Macintosh group in 1985, Jobs returned to a struggling Apple as CEO. Larry Page stepped aside in 2001 as CEO of Google (GOOG, GOOGL) — now Alphabet — before taking the reins again in 2011. Likewise, current Twitter CEO Jack Dorsey was fired in 2008 as Twitter’s (TWTR) chief executive only to return in 2015.

Yet all those examples have one thing in common: it took years for them to come back.

“Almost all of those examples were ‘white knights’ who came to rescue a broken situation,” the venture capitalist added. “Things aren’t going well. You’re running out of options. The old CEO comes back and saves the day. The reality is broken tech companies are hard to fix. And the track record of having a Steve Jobs, having a person come back and make it work, is a lot shorter than the track record of a person who comes back and couldn’t make it work.”

But if Uber doesn’t flail in the future, perhaps Kalanick won’t have the opportunity he needs to swoop in and reclaim the juggernaut he helped build from scratch.

JP Mangalindan is a senior correspondent for Yahoo Finance covering the intersection of tech and business. Email story tips and musings to jpm@oath.com. Follow him on Twitter or Facebook.  

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