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Jeff Klee: business leader showcase

By getting to know how business leaders tick, we can relate and learn from their experiences to make each of us better leaders ourselves. This interview with Jeff Klee, CEO of CheapAir.com is enlightening and a fun read.

jeff klee chepair.com

jeff klee chepair.com

Tell us about yourself and your work.

A couple years ago my wife told me, half-jokingly, that she knows that my priorities are my work, the Dodgers, and her, in that order. I’d probably edit the rankings and add in my recently born daughter, but otherwise I’d agree that this list sums me up pretty well.

Essentially, I’m just a regular computer geek who has always had a fascination with flying. At CheapAir.com, I get to combine the two. I get oddly excited about the technical challenge of having to sort through hundreds of thousands of flight combinations that may exist for a trip, consider the 10-20 possible fares that might apply for each leg, and come up with a simple, clear, and relevant list of options to present to a traveler. (And to do it all within the 6 seconds that researchers say someone is willing to wait for their results.)

Walk us through a typical day in your life.

I try to wake up before my family, so I’ll usually get out of bed between 5:30 and 6:00 and go right to my computer. I spend about 30 minutes going through my inbox, writing replies, and checking the overnight site stats. Then I’ll go for an hour long run and come home to have breakfast with my wife and 11 month old daughter.

The hardest (but best) hour of my day is the next hour when my wife takes our dog to the park while I watch the baby. Sometimes it’s my only chance of the day to play with her and, as she gets bigger, that keeps getting better. It’s not easy, though, and by the time my wife gets back I’m always thoroughly beaten down and in awe of how she does what she does, which I know is much harder than what I do.

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When I get to work, it’s usually with grand plans of all the things I am going to accomplish that day. But, once it starts, emails and conference calls and meetings tend to take over. A workaholic, I’ve historically stayed in the office until at least 7:00pm, sometimes much later, but ever since my daughter was born I have tried to leave earlier.

As soon as my family goes to sleep, though, I am right back on the computer. Late at night is the best time for me to get some “real work” done – a lot of the software development work that I’m still involved with – and I’ll work as long as I can, until I’m too tired to stay awake any longer.

What is your educational background?

I went to the University of Michigan for undergrad, and have a degree in economics.

Where were you raised? Where all have you lived?

I grew up in Los Angeles, left for 4 years to go to college in Michigan, and then came right back.

At age 15, what did you want to be when you grew up?

I’ve had the entrepreneur bug ever since I was very young. I always wanted to have my own business. As a kid, I was obsessed with making money and I went from one scheme to another, selling anything I could think to sell, like toys and candy to neighborhood kids or food to neighborhood construction workers. At 13 I created a laughably bad computer game for the Atari 800 which drew some interest from a software company. It wasn’t exactly a commercial hit, but it did make me a few hundred dollars.

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By 15, I had turned my attention to scalping Dodger tickets and I actually did pretty well at that, thanks partly to Fernando Valenzuela and the fact that every game he pitched would be a sellout. So I never knew what exactly I wanted to do when I grew up, but I did know that I wanted to be in business.

If you could start over…

If you could start your current career over with everything you know today, what would you do differently?

I would take a different approach to building a team. I have an absolutely incredible group of colleagues right now who are smart, fun, hard-working, and very passionate, but getting to this point took longer than it needed to. In the early days of our company, we had a lot of luck hiring very young people right out of high school or college (or in some cases, still in high school) who were amazingly dedicated and capable.

Over time, many of them began to assume more and more responsibilities and, in fact, most are still with us in some sort of management capacity. There was a point in time where we were a decent sized travel company run completely by people (including myself and my business partners) who, not only had never worked in the travel industry before, but, in most cases, had never even had a real job!

I used to take great pride in the fact that everyone in our organization at every level (again including myself) had started at the very bottom and spent years working in the trenches, answering phones or processing tickets. I used to regularly say that, in hiring, all that matters is character. I truly believed that good people who are smart with integrity and a good work ethic can accomplish anything, even if they have no experience. I still believe that but I also think, in hindsight, there were times where we could have and should have gone outside our organization and brought in individuals with very specific skill sets and very specific experience that we just didn’t have within our group.

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What is something unique that you do to balance work and life?

The question of balance has always been a tough one for me because I’ve never fully bought into the idea that work and life are separate. I have a hard time delineating between the two. I love what I do and my business is a huge part of who I am. My work life and personal life pretty much blend together and work is just another thing that makes life rewarding. I know I’m very lucky to be able to say that.

I’m a workaholic. I work more hours than anyone I know, but that’s OK, because I love what I do. I get up early and I stay up late and no matter where I am, I’m probably at least checking email. But it works both ways. I may work a lot of Saturdays and Sundays, but if there’s a midweek day game at Dodger Stadium I’ll be there more often than not. And when my daughter is old enough to have games, or dances, or anything else, I’ll be there, too. I may be at the computer after midnight many nights a week, but I’ll also be late to the office most mornings, so I can have breakfast with my family. Whether that is “balanced” or “unbalanced” doesn’t really matter to me, I’m not thinking in those terms.

What keeps you up at night?

My daughter. If only she’d start sleeping through the night!

More seriously, though, what makes me more anxious than anything is a country that’s losing its way. America used to be the place where big things were done and big problems were solved. Our parents and grandparents and great grandparents worked hard, made sacrifices, and did whatever needed to be done so that things could be easier for the next generation.

What’s happened to that spirit? Today, vision, ideals, and tenacity have given way to pettiness, apathy, and short-sightedness. I look at my daughter and I know that, barring a radical change, she is going to live in a country that is less hopeful, less inspired, and less a land of opportunity than the one I grew up in. Knowing that makes it really hard to sleep, sometimes.

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If you could be someone else…

If you could spend one day in the life of another industry leader, who would it be? Why?

Sergey Brin of Google. First off, it sounds like he has a pretty cool life (with, apparently, a great office and a great plane). But more importantly he and Larry Page have accomplished a technical feat that still blows me away every time I use Google. As someone who has spent countless hours trying to shave off a second or two from our airfare searches, I understand how challenging it can be to quickly sort through massive amounts of data. Google has built something that is, by orders of magnitude, so much better than what anyone else has done, that most people takes it for granted. It may take 6 seconds to search for a flight to New York, or a few seconds to search the iTunes store, or sometimes up to 10 seconds just to move from one page to another on a lot of web sites. But Google will find virtually any piece of information in the world in less than a second, usually responding with what you need before you can even finishing typing it! I know there are many who are suspicious of Google, but I am perpetually in awe of them.

What tools can you not live without?

For a computer geek, I’m surprisingly not that interested in gadgets. That is, as long as I have access to the internet at all times. I saw a clip of a comedian a few weeks ago doing a bit about being on a plane with in-flight WiFi where the internet connection stopped working. The guy sitting next to him got furious and the comedian joked that it’s shocking how quickly people come to think that the world owes them cheap, unfettered, uninterrupted access to even the most complicated and amazing technologies. For that, I’m as guilty as his seat mate.

I know that the internet is a technical miracle, the way it brings every bit of information in the world to people in every corner of the earth. But if for one minute there is a glitch and that amazing technology gets a little slow, I’m the first to declare what an outrage it is. I can live without most tools, but if I’m anywhere without a high speed internet connection, I get anxious.

What about you would most not believe unless they knew you?

I don’t eat condiments. Ketchup, mustard, mayo, I hate them all. I have spent countless hours debating the merits of a plain Dodger Dog versus one loaded with everything but, so far, it’s been a losing battle. My wife constantly complains that our 11th month old has a more mature palette than I do.

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What inspirational quote has stuck with you the longest?

“The only way out is in.” I don’t know where it came from but it was said to me by a mentor of mine many years ago. Bad things happen in business and in life. Some bad breaks are not your fault and couldn’t have been foreseen. But often it doesn’t really matter why something happened, who’s to blame, or who “should” be responsible for fixing it. I have learned that if something is really important, I need to take ownership of it, put my head down, and just get it done. That doesn’t mean I have to do everything myself; I have a great team that I am lucky enough to be able to rely on. But it does mean taking ultimate responsibility for the situation and the outcome.

The American Genius is news, insights, tools, and inspiration for business owners and professionals. AG condenses information on technology, business, social media, startups, economics and more, so you don’t have to.

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