In 2004, Orbitz alumnus Steve Hafner co-founded Kayak and fixed the aggravating process of shopping for airplane tickets. As Kayak’s CEO, he managed the company through an IPO in 2012 and its $2.1B acquisition by The Priceline Group in 2013. We asked him how he gets his work done.
Location: Miami, FL
Current Gig: CEO, Kayak
One word that best describes how you work: Selectively
Current mobile device: iPhone 7 (only because I bricked my 6 with water last week)
Current computer: An underpowered 2015 MacBook Air
First of all, tell me a little about your background and how you got to where you are today.
Like most Americans, I’m a mutt. My mom is Swedish and my dad is German and Irish. I was born in Peru and moved around a lot growing up.
The Internet was created right when I was finishing college and I knew it would revolutionize commerce. After a few years of management consulting to pay the bills, I left to help start one of the first online travel agencies. We took that company public in 2003 for over $1B. But I wasn’t satisfied with what we had built, so I left and started Kayak.
Since then, Kayak has become a global travel company with local websites in 60 countries and over 2 billion consumer requests for information each year. The Priceline Group bought us in 2013 for $2.1B but nothing’s changed in my role. The world is a big place and people need to see it. Our mission at Kayak is to help with that.
What apps, software, or tools can’t you live without?
Kayak for sure, plus Uber and Waze. I travel all the time and FaceTime keeps me connected to my five daughters and fiancée Staci. For work, Slack, Google Docs, and Dropbox. For play, Netflix, Spotify, Laughable and SeatGeek.
I’m also an Amazon Alexa fan. We just recently upgraded the Kayak skill so that you have the option to book a hotel room with just your voice. We’re the first travel company to offer voice-bookings and while it’s early days, we’re excited about where it’s headed.
What’s your workspace setup like?
Minimalistic. Only a few people at Kayak have offices and I’m not one of them. I don’t keep much on my desk because we move seats fairly often so our teams have the opportunity to get to know new people. Right now, my seat is right outside of our kitchen.
What’s your best time-saving shortcut or life hack?
Take real vacations. My out of office messages tell people that their emails will be automatically deleted while I’m gone. If it’s important, they can tell me when I’m back or handle it themselves. Life is too precious and short to always be “on.”
What’s your favorite to-do list manager?
I keep a small spiral notebook and write everything down in it—very old-school for a tech guy. But it’s somehow satisfying to scratch completed items off my list, and it helps me have a historical record of what I’ve done over time.
What everyday thing are you better at than everyone else? What’s your secret?
I’m great at just about every bar game—pool, cards, cribbage, cornhole, Connect Four, you name it. I’ve probably spent way too much time in bars during my travels.
What do you listen to while you work?
The news annoys me these days. So most of the time I listen to Spotify playlists of either Lorde, The Movement, or Willie Nelson.
What are you currently reading? Or what’s something you’d recommend?
My favorite book is A Confederacy of Dunces and I’m reading it again right now. It’s too funny not to revisit every year. I also recently read Elon Musk’s biography which I found inspiring.
How do you recharge? What do you do when you want to forget about work?
I’m fortunate to live in Miami Beach, and I also have a beach house in Rowayton CT. To relax, I just take my daughters to the beach or on our Chris Craft. I also like working out and cross training.
What’s your favorite side project?
I love manual tasks like yard work and tinkering with broken stuff. I spend so much time on computers and in tech that it’s comforting to actually use my hands in the physical world.
What’s your sleep routine like? Are you a night owl or early riser?
I aspire to be a night owl, but having two daughters under two makes that really hard. So these days I’m an early (and often) riser.
Fill in the blank: I’d love to see _________ answer these same questions.
Paul English, co-founder of Kayak, and our former CTO. The best leaders know their strengths and deficiencies, and plug the latter with complementary talent. Paul is everything that I’m not, which was essential to our success in the early days.
What’s the best advice you’ve ever received?
Be likable. It seems silly, I know. But people have a choice of whom to be around, and if you’re likable, they’re more likely to share information and ideas, work better together, and be productive. Kayak’s office culture and environment reflect that idea too. We want our folks to have surroundings that add energy to their lives and enjoy coming to work.
Is there anything else you’d like to add that might be interesting to readers?
While most of my time is spent thinking about how to make Kayak’s travel services and tools even better, I also think more broadly. I’m always on the lookout for how to make life simpler. There’s so much wasted time, effort, and capital in the world.
For example, I can’t wait for self-driving cars and car-sharing fleets to become mainstream. Imagine a world with fewer streets, parking lots, garages, and traffic. New York City could have green pedestrian thoroughfares!
This interview has been lightly edited for clarity.