A lifelong passion for aviation led Dan Wolf to cofound Cape Air in 1988 with only eight employees and one route between Boston and Provincetown. The fully licensed pilot trained during college summers in Chatham and soon after graduating from Wesleyan University with a degree in political philosophy, he went to the Quaker School of Aeronautics to get a degree in airframe and power plant maintenance enabling him to be a licensed mechanic. “I figured if I loved flying so much, I ought to figure out how airplanes work and how to fix them.”
Today, the Hyannis-based Cape Air (along with its sister airline Nantucket Airlines) is one of the largest independent regional airlines in the United States with 1,200 employees serving 44 destinations ranging from Hyannis to Guam. The 59-year-old CEO, who lives in Harwich with his wife, recently shared what inspired him to become a pilot, how he divides his time between Hyannis and Boston, where he’s a third-term Massachusetts state senator, representing the Cape Cod and Islands district, and the first item on his 2017 bucket list when he leaves politics.
Q. Why do you like to fly?
A. Oh, my God — it was a passion I was born with and I’ve been flying now for 40 years and I don’t think there’s a flight that I’ve taken that I haven’t felt was magic. You really gain an appreciation and a perspective of the world beneath you — the connectedness of things.
Q. What was your first airplane ride like?
A. It was with my great uncle, who was a brigadier general in the [US] Air Force, who had a small airplane of his own and he took me up to see how I would like it and I got airsick [laughs]! I got airsick for the first three flights, but at the same time I was just in awe — the ability to sit in an item heavier than air and actually fly — it’s a privilege I will never take for granted.
Q. What are your responsibilities as CEO?
A. I still fly on the weekends in the summer and I’m very involved in all the long-term strategic decisions. We’re looking to getting into a seaplane operation from Boston to New York, and over the next 10 to 15 years we’re going to be replacing our 93 planes with new aircraft.
Q. Best part of job?
A. The people I work with at Cape Air, without a doubt.
Q. Worst part?
A. The externalities of the business that we can’t control, like weather, air traffic control, and mechanical issues.
Q. Favorite destination?
A. I’d still have to say the Cape and Islands. It’s one of the most beautiful places environmentally and then culturally it’s one of the most interesting places that has attracted extraordinary people.
Q. Fantasy passenger?
A. It doesn’t have to be fantasy. I’ve flown first family people, Clinton family members, the Kennedys — celebrities. But what I love is sharing the experience — being able to point out just how incredibly beautiful it is [from the air].
Q. How do you divide your time between Cape Air and the State House ?
A. Some parts of the year, like the summer and late fall, we’re not in session so most of my time is “in district” at Cape Air. Then there are times like now when we’re gearing up for budget when I’m here three days a week and Cape Air two days a week. Life is full, but I love it.
Q. Why politics?
A. There have always been two parallel paths that I’ve been interested in — public service, which is the political science part, and aviation.
Q. Is there any overlap with what you do?
A. Airlines are dependent upon good roads and airport access and functioning Federal Aviation Administration regulatory oversight, but also for facilities and air traffic control. It makes me a better legislator to understand the business side and transportation side, and it makes me a better CEO to really understand some of the public policy issues and how government works.
Q. What do you do to relax?
A. I do a lot of bike riding — I’ve ridden the Pan-Mass Challenge five times — and my wife and I have a beautiful dog that we walk. I’m also a voracious reader and usually have a biography and a novel going at any one time.
Q. What are you reading now?
A. “The Good Lord Bird” by James McBride and Robert Reich’s new book “Saving Capitalism.” I’m also working my way through David McCullough’s “1776” about George Washington, which is like 9 million pages.
Q. What is on your bucket list once you leave politics?
A. I want to get to all the Cape Air destinations — 44 really cool places all the way from Rota [in Micronesia] to Glendive, Montana.
Q. By the way, what’s the Cape Air in-flight meal?
A. A great little box of mints.
A. It’s a little joke we came up with because most of our flights are so short.