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What Captivates the Captivating Tony Haile of Chartbeat

Don’t be fooled by Tony Haile’s eclectic resume, which includes stints in the Middle East, around-the-world yacht racing and polar expeditions. “I see my career as being pretty consistent even though for most people it probably looks bizarre,” says the charismatic chief executive officer of media analytics company Chartbeat. The common thread: “I want to continuously find the things that challenge me and make me better.”

Haile plunged headfirst into the world of startups in 2007 when a friend asked him to take a look at a business plan for a social network startup. Haile, a self-described “closet geek,” wrote a six-page critique of what he considered a terrible business plan. “They said ‘If you’re so smart why don’t you help run this thing,’” says Haile, who, naturally, said yes.

In 2009, the New York startup studio Betaworks tapped him to help grow Chartbeat from an in-house prototype to a viable business. The now 55-employee firm builds tools for web publishers, from Al Jazeera to The New York Times, that bring to light data on where readers are clicking, why they stop reading and how to adapt their content to keep them coming back.    

Entrepreneur.com spoke with Haile about what keeps him captivated.

ENTREPRENEUR: Beginning in 2000, you were part of crew that finished an around the-world yacht race that covered 33,000 miles and lasted nearly a year. Did you grow up sailing?
Haile: I started out with little experience but during university I got this idea that I wanted to do this. Every summer I lived on a boat working as a crew, and I’d do boat deliveries, Atlantic crossings, working for peanuts and learning to sail big oceangoing boats. For the race, my position was bowman, which meant I stood at the pointy end of the boat and got the shit kicked out of me. At times it was utterly terrifying, but I learned more about building a team and dealing with risk in those 10 months than I have at any other point in my life.

ENTREPRENEUR: Companies charter boats for team-building exercises, albeit around the harbor for a day. Do you think sailing is a good analogy for leadership?
Haile: I’ve been the guy serving drinks at those events. Yacht racing is great for learning since there’s no one leadership style. You have to apply different leadership styles to different situations. There are times when everything is going well, and you don’t need a heavy hand; people can have autonomy and get the job done. Then there are times of crisis, when you’re in a hurricane and the boat is in danger, where strong leadership comes in.

ENTREPRENEUR: A couple of years after the race you moved on to the North Pole. Are you prone to boredom?
Haile: On the boat race someone gave me a biography of [Sir Ernest] Shackleton [a famous Antarctic explorer]. I came back and was looking for that next test of myself. It’s not that I get bored. I get fascinated with a topic and within that topic I get a chance to challenge myself and learn where my boundaries are. Sometimes you come across the boundaries very fast and sometimes you see beyond the horizon.

Sailing taught me about teams and the polar world taught me about individual effort and self-discipline. Apart from risk of losing a limb, I find that startups are very similar. It’s not just what you have to learn but what you have to unlearn. Everything that’s true at five employees is very different with 25 people.

ENTREPRENEUR: You’re an avid reader [Haile keeps a log of the books he’s read on tonyhaile.com]. What business books have had the biggest impact on how you think about running a company?
Haile: The book that taught me the most about strategy was The Innovators Dilemma, by Clayton Christensen. The two books that taught me about management are What Got You Here Won't Get You There, by Marshall Goldsmith and The Feiner Points of Leadership by Michael Feiner.

ENTREPRENEUR: Outside of work, how are you challenging yourself these days?
Haile:  
I’ve been taking some Japanese. I wanted something very different from my job and wanted to train my brain in different ways. At first I thought it was incredibly logical, and then I started finding out about the different quirks, all the ways you can count to ten depending on the shape of the object. I’m doing that and piano… I took it up a month ago. I bought a keyboard, which my wife was horrified by because we have a small apartment and it’s a rather large keyboard. Maybe one day I can sing Billy Joel songs in Japanese.

This interview has been edited and condensed. 

Sarah Max is a freelance writer in Bend, Ore. She has covered business and personal finance for more than a decade for such publications as BusinessWeek, CNNMoney.com, Money and The Wall Street Journal. In 2009 Sarah got a first-hand look at the ups and downs of entrepreneurship when she helped launch 1859 Oregon’s Magazine, a quarterly magazine and website for which she is executive editor.

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