Nice guys finish last – right?

wild ride

Every heard that expression, Nice guys finish last? It’s credited to Leo Durocher, a famed baseball coach who was definitely not a nice guy. He saw baseball as war and his philosophy was “win at all costs.”

Well I don’t know if Travis Kalanick is a baseball fan or not – I certainly didn’t learn that in Wild Ride, Inside Uber’s Quest for World Domination by Adam Lashinsky, but I did learn he’s pretty far from a nice guy and as far as startup valuations go, Uber is in first place by a mile, valued at close to $70 billion.

If you look at FANG – Facebook, Amazon, Netflix and Google – four of the most popular and best performing tech stocks, are their leaders nice guys or not? Let’s add Apple to the mix, since it’s the most valuable company by market cap in the work.

So we have Mark Zuckerberg (Facebook), Jeff Bezos (Amazon), Reed Hastings (Netflix), Larry Page (Google) and Tim Cook (Apple). From what I’ve read – and I’m a very avid reader of tech news thanks to Flipboard and Leaf – only Jeff Bezos fits the Leo Durocher mode of a not so nice guy, at least according to The Everything Store: Jeff Bezos and the age of Amazon by Brad Stone.

Mark Zuckerberg has joined The Giving Pledge – a commitment by the world’s wealthiest individuals and families to dedicate the majority of their wealth to giving back; Reed Hastings seems a rather low profile CEO, and aside from irritating Netflix users with occasional changes to Netflix’s pricing seems to be a nice guy; Larry Page of Google rarely makes the news, but Google is always at the top of the list as the best place to work; and Tim Cook has taken very public stands in favor of LBGT rights and the environment.

But from reading Wild Ride, Travis Kalanick is not a nice guy. He’s stubborn, aggressive, abrasive, and likes to not just bend the rules but to break them. But in his defense he’s been fighting one of the most highly entrenched government mandated cartels of all time: the taxi industry. I’ve always hated taxis: the cabs are dirty, beat-up and with suspensions that threaten my spinal cord. The drivers never seemed to know where they were going in the days before GPS, the prices were confiscatory compared to public transportation, cabs were often late and sometimes didn’t show up at all. I’ve always done everything I could to avoid taking cabs. And though I’m a serial entrepreneur with the hubris to think I always know a better way to get things done, it never occurred to me that there was an alternative to cabs. Despite the fact that I grew up in a community where car pooling was de rigueur and I spend much of my youth hitchhiking through the U.S., Canada, Europe, and the Middle East.

And truth be told, neither did Travis Kalanick. If you read Wild Ride you’ll find the true origin story of Uber, which started out as a service that tried to displace black cars – limousines – not cabs. And Kalanick was not the founding father, he started out as an advisor and only later became CEO. And it was Lyft that first went after the taxi industry, attacking the low end of the market, since Uber seemed to have the high end.

Wild Ride is a very well written book, based dozens of first hand interviews that delivers an inside look at Uber – it’s not pretty, but it’s fascinating, sort of like a rattlesnake. Oddly enough the book lacks an index, but to the best of my recollection the word mentor does not appear in the book.

So are there lessons to be learned from Uber? There are a few: they have pursued the classic “get big fast” strategy to gain their dominant position. Kalanick has built a highly aggressive, hard charging rule-bending culture, and Uber has perfected the city by city rollout strategy. Like Facebook, whose rollout strategy was brilliant – starting with Harvard, moving to the Ivy league, and so on – Uber has a highly replicable and scalable model that is worth studying for any entrepreneur who has a local service and wants to grow nationally or even internationally. The other lesson well worth noting is how Kalanick and Uber have harnessed the power of their very well satisfied customer base every time local authorities and or the taxi cab cartel has attempted to block them from setting up shop. The voice of the customer can even drown out the loudest lobbyists if channeled as Uber has done so well.

The bottom line: Travis Kalanick is not a nice guy, Uber is not a nice company – just do some reading on how happy its driver are. But right now they are in first place. Time will tell if they can continue to be both the bad boys of billion dollar startups and stay in first place or not.

Author: Mentorphile

Mentor, coach, and advisor to entrepreneurs, small businesses, and non-profit organizations. General manager with significant experience in both for-profit and non-profit organizations. Focus on media and information. On founding team of four venture-backed companies. Currently Chairman of Popsleuth, Inc., maker of the Endorfyn app for keeping fans updated on new stuff from their favorite artists.

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