Want to know how to travel in style, just like the pros? We check in with frequent fliers to find out how often they fly, their favorite destinations and what they never leave home without.

John K. Hart
John K. Hart

Name: John K. Hart

Occupation: Founder & CEO of Imagine If, a startup

Hometown: Arlington, VA

Residence: Arlington, VA

College: University of Virginia

College major: Entered as an Honors Engineer—a Rodman Scholar, with a major in Computer Science. Transferred my second year and became an Echols Scholar, with a major in Government & Foreign Affairs. I was also in Army ROTC (like a double major!).

Website: StaySmarter.com

Twitter: @JohnKHart

Short bio: I am the Founder and CEO of Imagine If, a team of hotel insiders that is the maker of the StayFaster and StayAtHand websites and apps, a powerful suite of tools that are the smartest way to get your hotel stay. I have spent over 25 years delivering innovative, award-winning solutions at the intersection of people, information and technology. I love using technology to solve problems. I started programming when I was 13, was an honors engineer at the University of Virginia, a software developer for a defense contractor and an IT project manager at Marriott. I also enjoy building high performing teams, whether as a small unit leader in the Army, a National Board classroom teacher, a licensed soccer coach for elementary through high school teams, a project manager, a functional leader and as the CEO of a disruptive start up.

How often do you fly? Only when I must, typically once a month. I used to love to fly as a child, and did so quite often. As I’ve become older, I like flying less. I fly around the country to meet investors, sometimes even just for coffee or a meal. I usually take the redeye so I can return to be with my family, and to save our company money on both the ticket and the hotel.

How many countries have you been to? Approximately a dozen—besides US, Canada and Mexico—I spent time in Europe and in Southern Africa.

How many continents have you been to? Three (NA, Europe, Africa).

Earliest travel memory: I was 7 and flying with my 5-year-old brother unaccompanied from the East Coast to Denver, CO. The flight attendants adopted us, took us to the travel lounges, gave us special packages and rewarded us with visits to the cockpits. After that, flying with my parents was somewhat of a letdown.

Favorite American city: Washington, DC. I love the educated, cosmopolitan city that still has room for locals, green spaces and lots of sky.

Favorite international city: Capetown, RSA. Simply the most beautiful city I’ve ever seen. The contrast between the city and Table Mountain is breaktaking.

Friendliest people in the world: Children. Whether in Africa, Central America or across the US, children are openly curious, kind-hearted, and simply fun to be around. I have fond memories of playing soccer in Lesotho (Southern Africa) with the villagers—many of whom were barefoot, with a rock designated as the goal. One side of the field was a several-hundred-foot cliff—so it made for an exciting field of play!

Favorite airline: Alaska Airlines.

Favorite aircraft type: Anything without propellers.

Aisle or window: Aisle.

Favorite U.S. airport: MCO (Orlando International Airport).

Favorite hotel: The Ritz-Carlton.

Favorite beach: North Myrtle Beach, SC. I love the long, shell-free sand, the few-if-any jellyfish, the gentle slope of the beach, and the great food in all of the nearby restaurants.

Favorite fancy restaurant: 1789, Washington DC. I have been eating there over 30 years.

Favorite fruit: Strawberries.

Favorite food: Surf & Turf—I love shellfish and steak.

Least favorite food: Fried jellyfish—not that I’ve tried it—but I can’t imagine anything would convince me to do so.

Drink of choice (in the air and on the ground): I actually don’t like drinking on flights—but on the ground, I like craft beer at casual events, white wine at formal events before the meal, and red wine with my meals.

Right now I am reading: “The Hard Thing About Hard Things” by Ben Horowitz. One of the best books about the startup experience, it speaks to the truth of the emotional journey.

Top 3 favorite travel newsletters/magazines/blogs: 1) Magazine, Travel + Leisure; 2) Blog, Million Mile Secrets; 3) Blog, Kidventurous.

Favorite travel website(s)—besides JohnnyJet.com, of course! Our Kids—This amazing site provides a terrific directory on DC area activities for families, and great deals through its member services.

5 things you bring on a plane: 1) Water; 2) snack; 3) phone; 4) laptop; 5) magazine(s).

What do you always seem to forget? Cufflinks—not that I always need them, but when I do, I’ve forgotten to bring them.

What do you like least about travel? Being away from my family. I just really enjoy the time we get to spend with our daughters, who are in 2nd and 4th grade.

What do you want your loved one to buy you from an airport Duty Free store? Godiva chocolate—the older I get, the better it tastes. I absolutely love it!

Favorite travel app(s): StayAtHand—for all of my stays; Google Maps—for getting from here to there; Uber—for my rides.

Most embarrassing travel moment: As a young man, chatting up an attractive woman in the seat next to me, then getting airsick just as the plane landed.

Worst travel moment: Taking the hovercraft from CapeTown to Robbin Island after a late night of drinking games with the local bartender. My wife said it was the first time she had seen someone who was actually green.

What’s your dream destination? Australia—I could spend a month visiting the country and seeing the culture.

Best travel tip: When in Rome do as the Romans do.

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