Which classes or experiences at Dartmouth helped prepare you to be a tech entrepreneur?
I didn’t take any computer science at Dartmouth and I was fairly light on math. I was an economics and history major. What really helped me was learning how to form an argument, to be articulate, and to identify smart people and communicate with them. All of that developed my ability to define a problem, determine a potential solution, and then execute it. Now, I think the curriculum could be revised a bit so computer science is a mandatory course. Classics was a mandatory course for me, and it taught me how to think. But a computer science course would have served me well, too.
You’re passionate about traveling. Is passion essential for an entrepreneur?
Absolutely. You have to love what you do, whether it’s washing cars, making burritos, or creating a travel site. When you have passion about something, you tend to think about it all the time. Some of your best ideas will come at inopportune moments, like the middle of the night, when you’re sick, or when you’re taking a shower. If you’re not in a job that you’re passionate about, you’re not going to be thinking about it in the shower.
Kayak has been a tremendous success and its range of services continues to grow. What’s your ultimate goal for Kayak?
We started Kayak to have one app for planning and managing your travel, worldwide, and we’re far short of that goal. We’re really good at helping you find plane tickets, hotels, and rental cars—at the best prices around. But what we don’t do is take advantage of this new platform called the smartphone. Not only should we help you search and find the best deals, we should suggest where to go and help you throughout your trip. That’s what we’re really trying to achieve at Kayak, and we’re making progress. If you have a Kayak app on your phone, you can capture your boarding pass on it, and you can bypass check-in at some hotels and go straight to your room. Soon we’ll have integration with Silvercar so you can start your rental car with your phone. We want people to travel more, but there are so many friction points in the travel experience. If we can eliminate that friction and make going to Cuba as easy as going to the grocery store, the world would be a better place.