From Gates To Zuckerberg To... Kalanick? What Went Wrong With Uber CEO

In his early days growing Microsoft, Bill Gates was reported to be the original enfant terrible. Very tough on people and teams. And the behavior of Microsoft matched: vaporware was a term coined not to define poorly engineered software, but to hint at Microsoft’s future product development, thus terrifying entrepreneurs and venture capitalists and steering them away from investment in an area that could threaten Microsoft’s future growth. And most importantly, Microsoft had a lock-solid monopoly on their markets.

Mark Zuckerberg’s start was similar to Gates. Hollywood doesn’t make a movie about you because there’s no drama. One of Facebook’s venture investors explained away Mark’s early behavior, saying it was just growing pains. Today 2 billion humans use Facebook, which defines the social network, and with smart moves like Instagram’s purchase, there’s no sign Mark’s game is fading any time soon.

Now comes Uber, the most highly valued startup, growing in just seven years from nada to $70 billion with a lock on one market and the possibility of a lock on an upcoming market – self driving car booking. But for Travis Kalanick, the playbook seemed to break down. Unlike Gates and Zuckerberg, who made their mistakes in their teens and twenties, Travis does not get the youthful indiscretion excuse. At age 40 you can’t explain away boorish behavior or intentionally developing software to thwart local regulators.

What went wrong for Travis, while Bill and Mark matured and prospered?

Three things: first, great entrepreneurs have great partners. Always. Gates had Steve Ballmer and Paul Allen. Gates and Ballmer famously said their highest value for each other was coaching on time and priority management. That’s the essence of a great partnership. Batman and Robin, Sponge Bob and Patrick…Bill and Steve. Want more examples? Steve Jobs – he had Woz, then Jony Ive and Tim Cook. Great entrepreneurs never really go it alone. There’s always a trusted partner waiting in the wings, someone whose opinion they value who holds them accountable.

Second: Great entrepreneurs recognize the difference between the front stage and the back stage – and they keep them separate. Everyone’s heard how diligently Steve Jobs worked to pull off product release events. They were shows, meticulously planned, and the public ate it up. We love cheering on a great performer, and with Steve Jobs his products really changed the way we live.

And Travis? Filmed during an Uber ride in full-jerk mode with someone who is effectively an employee. It’s been viewed millions of times. Is he actually Mahatma Gandhi the other 99 percent of the time? Unlikely. If you aren’t inspiring it hurts to have your worst moments on public display, dispiriting your investors, board, employees – all of the supporters and cheerleaders you need to succeed.

Which brings up the essence of leadership in the public eye in 2017: your employees are another front stage, a public representation of what your company is all about. So when employees start grumbling or in Uber’s case reports of sexual harassment and underpaid drivers surface it’s time to review what you stand for. A good part of Uber’s success was not just the technology, but a full-throated charge to enter new markets despite legal obstacles. That kind of stress needs leadership that grows and evolves as challenges grow. And because the team is responsible for executing management’s plans, biting the hand that feeds – employees, staff, vendors, investors ― is a recipe for disaster.

Finally: great entrepreneurs have incredible self-discipline. Mark Zuckerberg committing to study Mandarin Chinese is an act of self-discipline. He was already a billionaire, had already arrived. He sought for higher goals and more meaning, not just the exercise of power. Morningstar founder, Joe Mansueto, is a relentless student of success, consciously designing his path from startup in a two-bedroom apartment to world-spanning financial publishing powerhouse with 4,600 employees. His design for his own progress included an intense, ongoing study of how successful companies grow, change and adapt to their increasing challenges. He read and studied to learn how to grow an organization and even more importantly how to avoid the pitfalls that trip up so many companies. He formed a board of directors years before going public – an act of self-discipline most private company owners are reluctant to take on at any point.

Before he was fired, Travis announced that 14 managers would run Uber while he took a leave of absence. Fourteen. Any leader of a large, complex organization could have a delusional moment. In private. The double whammy here is that the public ever learned of such a cock-eyed idea. It’s just not the mark of a self-reflective, disciplined leader. What a way to lose the faith and confidence of investors, board, employees and customers.

Steve Jobs had a comeback even more amazing than his first go-round. If you’re a fan of Pixar’s Toy Story, Monsters Inc., Wall-E, or any of its other movies, or if your iPhone or iPad are always by your side, you’re a beneficiary of Steve Jobs’ second act. Bill and Melinda Gates, philanthropists, are proving to be a tremendous force for good in the world. Bill’s second act was not a straight line from software king, but it is dazzling and inspiring.

Goodbye to Travis. Here’s hoping he can eventually pull off a second act even more amazing than Uber.