Kenn Ricci Illustration by Graham Smith

Illustration by Graham Smith

As principal of Directional Aviation Capital, a holding company that includes Sentient Jet, Flight Options and Flexjet, Kenn Ricci has initiated some of the biggest innovations in private aviation over the last 30 years, from new forms of fractional ownership to aircraft remanufacturing.

The former full-time pilot is chairman of Flexjet, which just opened its second private terminal in the U.S., in White Plains, N.Y.

01 What are you reading? 1944, by Jay Winik, which is about Franklin Roosevelt. 02 What’s your favorite city? Domestically, Phoenix. I moved there in 2002. Internationally, Cape Town. I used to fly Richard Branson there in the early ’90s. 03 How many days a year do you travel? Normally, 150. We have our children skip eighth grade, and we homeschool and travel with them. Last year we visited 29 countries, so well over 220 days. 04 Do you ever fly commercial? [Laughs] We do not. I wouldn’t want to be seen on commercial; I’d want to be seen on our product. 05 When was the last time you flew commercial? I went to North Korea last September on Air Koryo. You can’t fly there privately. 06 What’s your favorite plane as a passenger? As a pilot? They’d be the same: the Gulfstream G550. 07 Who’s the most interesting person you’ve ever flown? Without a doubt, Bill Clinton. [Ricci was Clinton’s pilot during his first presidential campaign.] Hillary’s a hoot—she’s fun, and makes you feel happy to be around her. 08 Outside of private aviation, what’s been your best recent service experience? Villa d’Este at Lake Como. They had closed the outside dining area because of weather, but they set up one table outside for us. 09 What is your investment philosophy? Overweight in cash, and invest in things you know. 10 What’s been your worst investing mistake? A real estate development in Florida. I didn’t understand how the project worked or how it was funded. 11 Your favorite movie? Field of Dreams. Everyone thinks it’s a baseball movie, but it’s about your parents. 12 TV show? Real Time with Bill Maher. I love to hear that contrarian view. 13 Beer, wine or spirits? Beer after a round of golf, a nice Italian wine with an Italian meal and a martini on date night with my wife. 14 Best restaurant? The Office in Cabo San Lucas. 15 What type of watch do you wear? Hublot. Every time I have a successful business transaction, I give myself a watch. I have probably eight or nine. Every time I wear one, it means something. 16 Favorite designer? Donald J. Pliner for shoes; Isaia and Canali for suits—usually made to measure. 17 What do you drive? A Tesla, and my wife’s Bentley whenever she’ll let me. 18 What’s the biggest challenge you’ve overcome? My youngest son has cystic fibrosis—it took 18 months to figure it out. For someone who can add numbers and read sales contracts, that’s really out of your comfort zone. 19 What keeps you up at night? Aircraft safety. 20 What’s your favorite philanthropy? We have a family foundation, and we support Able Flight, a program that teaches disabled people and vets who’ve lost a limb to fly. To see a paraplegic fly a plane is amazing.

This article originally appeared in the December 2016/January 2017 issue of Worth.