How much hustle is too much, and other lessons from the Travis Kalanick saga

2017 is Uber’s annus horribilis — one that is far from over even with iconic CEO Travis Kalanick departing in the middle of the year.

Image Credit: Anisha

Key takeaways:

  • Uber’s public fallout has been in the making since 2014.
  • The early hustling and shifts in the grey areas became breeding grounds for an unethical culture as the company grew.
  • Travis Kalanick should’ve made way for a new CEO or COO three years back.

“Necessity taught me the very fine art of bootstrapping. Blood, Sweat and Ramen is what I like to call it. I was always thinking about how to make things ultra-cheap, hyper-efficient while making a good story out of it.”

This is a tale that any entrepreneur would relate to. The great ‘hustle’ of building a product and achieving phenomenal scale. A post by Travis Kalanick in his archived blog, Swooshing, talks of the different ways in which he hustled over 10 years in different companies that he established and sold. These are powerful stories, ones that entrepreneurs find inspiring, mentors yearn to be associated with and investors put money into.

And yet on 13 June, in a letter to Uber employees, while announcing his indefinite leave of absence, he wrote:

“For the last eight years my life has always been about Uber. Recent events have brought home for me that people are more important than work, and that I need to take some time off of the day-to-day to grieve my mother, whom I buried on Friday, to reflect, to work on myself and to focus on building out a world-class leadership team.”

A week later, he succumbed to investor pressure and resigned, leaving behind a whole lot of questions and no real answers about the future of Uber. The CEO of one of the most valuable startups in the world had left with no real line of succession in place. The unicorn, valued at $68 billion, is now going to be run by 14 of its senior executives.

Uber is a mature product with a global presence. It has legions of loyalists, so the brand will sustain, for at least a while. Most investors believe that Uber will put an interim CEO in place before setting out to find a new leader.

The candidates have their work cut out for them because they will need to break the hustle-your-way-through-it-all image that Travis had acquired. In the meantime, what’s left is, as the Wall Street Journal put it, 14 bosses and one corporate Game of Thrones.

Half a world away, we look at the tragic character flaws and circumstances that served up a near-Shakespearean tragedy.

The tipping point?

Was it the #DeleteUber campaign? Was it Susan Fowler’s catastrophic blog post? Was it the Waymo lawsuit? Was it the ‘Hell’ or ‘Greyball’? The medical records saga? What went wrong? Which of these was the tipping point?

Krish Seshadri, who has earlier worked as a senior executive for Facebook and Zynga in the Valley and in India, believes it was a combination of cultural chaos and lack of leadership:

“Legal troubles and business problems are always a part of business. What really went wrong with Uber was the lack of a proper leadership that (should have) built a company solid with cultural values.”

Travis built a successful startup that not only changed the face of personal transportation but also became a force to reckon with while earning a sky-high valuation. When Uber started in 2011, based on an idea that is credited to Co-founder Garrett Camp, Kalanick was exactly the type of leader that the San-Francisco based ride-sharing app needed.

“There are very few startups that can succeed the way Uber has, and there are fewer entrepreneurs who have such a lasting impact on the world. There can be no denying the work he has put in. People in over 600 cities across the world love and use the product,” Kris points out.

Change-maker, rule-breaker

Travis was the driving force behind Uber’s growth. He built the company by pushing people hard, all the time. Given its unique model, he knew that Uber would have to walk a fine line between what was legal and what wasn’t. In defiance of taxi unions, it was making calling a cab a simple experience that put the cab driver in direct touch with the passenger.

Uber was ruthless in the way it got ahead. It reportedly deployed the dubious ‘Greyball’ technology, since 2014 to serve up an alternative (and non-functioning) version of its app. The aim, say, critics, was to avoid legal scrutiny in cities where its service had been banned, including South Korea, China, Australia and parts of the US.

Between 2014 and 2016, Uber is also reported to have used ‘Hell’, a software tool that could track how many of its competitors’ drivers were available for new rides and where. “We needed to get the job done. When you have a large vision, the focus is on ensuring that things get done,” an Uber employee based in the Valley conveyed to YourStory on condition of anonymity.

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