THE BLOG
08/22/2014 05:19 pm ET Updated Oct 22, 2014

3 Reasons Why It Sucks to Be the CEO Of Uber

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Sometimes I wonder why Uber CEO Travis Kalanick gets out of bed in the morning. OK, it's probably the fact that his company was recently valued at more than $18 billion which, depending on his ownership, makes him at the very least a billionaire. For most business people, that's motivation enough. But there's got to be an easier way to make that first billion, isn't there? I could never do what he does. I think it sucks to be the CEO of Uber. Why?

You must enjoy fights. Kalanick's battles with regulatory authorities, competitors and haters around the world are epic. Don't believe me? Just go ahead and search for news about "Uber." I just did. And here's what I found today: the company just won a short reprieve in Berlin from a city ban that had previously ruled that Uber did not comply with passenger safety standards and is now engaged in a war with taxi drivers in India. In Pittsburgh they've been required by the courts to provide information about its ridership. The Maryland Public Service Commission recently ruled that Uber is a "common carrier" and should be subject to greater regulation. They are fighting a growing number of ominous reports about people who keep getting into strangers' cars because they think it's an Uber vehicle and cab companies in San Diego who are furious with the ride sharing service for not only taking away business, but their drivers too. The company's rating system recently came under scrutiny and some guy alleging to be a "Boston Uber driver" has attracted attention after making serious allegations about the company's safety practices. By the way... that's just today. Which I guess is just another day at the office for Kalanick. If this were me I'd be jumping out the window.

But it's not me. Case in point: compare Uber with the once popular MonkeyParking app in San Francisco, a very useful application that allowed users to share and auction off city parking space. The founders of that company came under heat from local officials. So...they retreated. I'm not arguing their rationale and I probably would've done the same. Fighting City Hall is time consuming, expensive and intimidating. But would Kalanick have backed away? I seriously doubt it. This guy does not avoid battles. In fact, he seems to gleefully seek them out in order to see his vision accomplished. His advice for others: "Stand by your principles and be comfortable with confrontation. So few people are, so when the people with the red tape come, it becomes a negotiation." That's what successful and great entrepreneurs do. Unlike me, they're not afraid of a fight.

You have to grow a very thick skin. Recently, Uber and its main rival Lyft had a nasty public battle over Uber's competitive practices. Lyft accused Uber of having 177 of their employees order and then cancel more than 5,000 rides on Lyft in order to slow down the service. Uber countered with their own allegation that Lyft employees, drivers and one of its founders ordered 12,900 trips on Uber's app and then canceled them. It's not a pretty situation. But the media and Twitter-sphere loved it. I would've been sick to my stomach.

And for what it's worth, Lyft is not the only company who is less than enamored with Uber's competitive playbook. For example, a taxi association in the Seattle area recently sued Uber for "unlawful and deceptive business practices." Reports of price gauging have continued to plague the company over the past year, particularly after severe weather and concert events. And just this month, one taxi industry "leader" in New York City claimed that "...only rich Jews could afford the car service's surge-pricing program." Super! So along with everything else, the company is now instigating anti-Semitism.

I have never met the 37 year old Mr. Kalanick. But I can easily guess what he'd say if I asked him what he thought of others' opinions about him and how he runs his company. This is a guy who doesn't care what his haters and competitors think. He's changing the world. Me? I sometimes obsess over a single negative online comment. A complaint from one customer can turn my day upside down. I want everyone to think I'm the greatest. I lack the mojo, bravado and ego that great entrepreneurs have. And, of course, the thick skin.

Finally, you must not be afraid to fail. Uber may one day go down in flames. The service may eventually meet political, union and regulatory headwinds that are just too strong to overcome. A new competitor, with more resources and better connections may take away market share. An unplanned incident might occur that generates so much bad PR that customers turn away from the service. You never know. But do you think this will be the end of Kalanick? By now this is something you do know.

The current CEO of Uber is a UCLA drop out. His first company had to file for bankruptcy in order to protect itself from a major lawsuit. He ran out of money several times before founding and then selling another company, all before starting Uber. If Uber tanks you'll see Kalanick back doing something else. That's what makes a true entrepreneur. Someone who not only takes calculated risks, but is not afraid to fail. You get that impression when you read about Kalanick. Sure, he'll fight hard. But if he loses, he'll be back. My whole life as a business owner is spent protecting what's mine, saving money, conservatively managing my assets. Kalanick knows that if he loses everything he can just make it back again. He's not afraid. It's in his DNA.

You have to be a certain kind of person to disrupt the world. I am not that person. I think it would suck to be the CEO of Uber. Thankfully, there are others not like me.

A version of this column previously appeared on Inc.com.