As Jason Middleton explains it, he was a chubby kid whose major interest was sitting on the family couch in Bakersfield watching TV. Then at age 11 he fell in love with triathlon, did an Ironman at age 15, and turned pro at 17.

When lack of a run ended that dream, he got in on the ground floor of pro adventure racing. After that, he took up flying and co-founded a private jet charter company in Santa Barbara that helps support his wife Tricia and their children Aiden, Camryn and Nolan.

Slowtwitch: How did it all start?

Jason Middleton: I was born and raised in Bakersfield and my parents were not athletes. I was a chubby kid and I wasn't active.

ST: What led you to triathlon?

Jason: About 5th grade I met [future pro triathlete and Navy SEAL] Kerry Classen and we hit it off. He was an athlete and his parents were triathletes. Kerry and his parents were into road biking and I saw Kerry had this really cool road bike. So I saved my money and bought a black and red Trek 560. I was 11 years old and soon after I did a kids triathlon held with the Bakersfield USTS race.

ST: How did it go?

Jason: That first triathlon kicked my ass, but I fell in love with it. I started swimming and biking and running more, and after I hit puberty, I grew six inches and lost all the extra weight. When I was 14 I was pretty fast on the bike.

ST: You did your first Ironman very early.

Jason: I was 15, I could not get into Ironman Hawaii because they had a minimum age of 18. So I did Ironman Canada in ’88.

ST: How tough was it?

Jason: I talked to a few Ironman triathletes and they all said, ‘Don’t go hard at all.’ In my 15-year-old brain that meant don’t go 95 percent, just 90. I swam well and pushed the bike and I hit the turnaround in something like 5th place overall. I thought, ‘Uh-oh. All those guys told me to go easy!’ I backed off and cruised the last half but the damage was done. I jogged and walked to the run turnaround and on the way back I saw a really beautiful lawn with shade where I laid down and fell asleep. When my dad found me, I said, ‘I am done.’ He said, ‘You are so far ahead, you can walk to the finish.’ I finished in about 12 hours.

ST: You turned pro at an early age.

Jason: One of my best performances was a Bakersfield USTS race. That year they changed the course to a half Ironman with a 9.3 mile run. The pro field was strong and I started six minutes behind. I had a really good swim and because I rode that course almost every day, I caught Scott Tinley. I thought, ‘Holy shit! I am six minutes ahead of you right now!’ I passed every pro but Mike Pigg – and I put four minutes on him. I had a decent run and I ended up third or fourth. I was 17 and decided to turn pro.

ST: Were you going to college?

Jason: My parents didn't go to college. I was more interested in chasing girls and being an athlete.

ST: What happened with your pro career?

Jason: I raced a lot when I was 18, 19 and 20. I rode at the front and I would fall back to 20th on the run. No matter how much I worked, my 10k time was 36 minutes. So I stopped racing triathlons and took a year off.

ST: What did you do?

Jason: I partied, stopped working out and got fat. I wish I had someone to tell me go off and race bikes. I was fast on the bike, but my run sucked. If I had somebody pivot me into cycling, I could have had a decent career.

ST: You were there at the birth of adventure racing.

Jason: I saw the Raid Gauloises on TV. It looked really hard. I was 20 and that got me fired up for sport again. And they announced the first Eco-Challenge in the U.S. to be held 1995 in Utah.

ST: How did you go about it?

Jason: Some triathletes from Santa Cruz needed a teammate. I was 21 years old. We had no idea what we were doing. We showed up with monster backpacks, heavy hiking boots, three layers of clothes, sleeping bags and lots of food. It weighed a ton.

ST: Prize money?

Jason: There was a little money and we finished two days behind the winning team. During that race I thought ‘I am never doing this again.’ As soon as we finished, I thought, ‘Let’s get ready for next year.’

ST: What did you do to improve?

Jason: When we showed up to Utah our packs weighed 70 pounds. Two years later our packs were 15 pounds – with water. We wore running shoes and bunny running shorts. Three days into that race we were leading. But some personal issues erupted between some of my teammates and we fell apart halfway through. It frustrated the hell out of me. So I decided to start my own team and we were sponsored by Reebok.

ST: What did you learn that prepared you for running a charter air business?

Jason: When I started Team EarthLink in 1999, I became an entrepreneur. I had a hard time getting sponsors and asked Mark Burnett to sit down with me for coffee. I brought my 50-page sponsorship package and he said, ‘Jason you are doing this all wrong. You should be selling yourself. You have to give them one page and tell them what you will do for them. That’s it.’ I cut my proposal to one page and got a meeting with EarthLink. I told them we are going to get on the cover of a major magazine, we will get 48 Hours to follow us at Eco-Challenge and we will be featured on Discovery Channel coverage at Eco-Challenge. They gave me a one year contract.

ST: What next?

Jason: The next year EarthLink signed a 5-year contract for major money. That’s when I started making money. I was running a team so I had to manage all sorts of things - tax issues, travel schedule, logistics.

ST: What led you to flying?

Jason: Tricia and I were talking about starting a family and Burnett was phasing out Eco Challenge. Mark was the glue that kept the sport in the media, so I wondered what to do. Adventure racer buddy of mine was a corporate pilot and told me, ‘Man you’d love this.’

ST: What was the first step?

Jason: While I was still racing I trained and raced and flew when I could. I got my private, multi-engine and CFI instructor ratings all in one year.

ST: Was it the thrill of flying?

Jason: I love flying. But it was going to be my job. I've done very little flying for fun.

ST: Was it a straight line to success?

Jason: Before 9/11 you instructed for a year and went right to one of the regional airlines, then you went to a major airline. Then 9/11 changed all that. The airlines took 9/11 as an opportunity to cut. So I got a job flying charter airplanes. I am really glad, because it suited me more.

ST: How did you start your company?

Jason: Seven years after I started flying, I worked for a private owner whose business started to fade. He was a smart guy and he said, ‘Jason I have to get rid of all my assets. Market is gonna crash.’ His airplane was the first thing to go and I was without a job. Right then a friend just sold his software company and wanted to buy an airplane. I said, “What if we bought an airplane together and started a charter company?” He said, “I’m in.” A business guy in town came in as partner and CFO. We ran the company with one little jet. Our headquarters was a storage room in Hangar 3 at Santa Barbara Airport with two desks and an airplane parked outside.

ST: What kind of jobs did you get?

Jason: Our customers were light jet fliers - lieutenants of industry. That first year we had a lot of business. Then everything fell apart. We were lucky because we were very small and had little overhead. Some months I made nothing.

ST: When did you expand?

Jason: It took a year. We were a flight business and a management company. We operated aircraft for individual owners. We are also an air carrier which allows us to operate airplanes commercially. When the owners aren’t using the airplane, we can generate revenue through charter and share the profits. The next four years we added a few airplanes. My philosophy is we wanted the best airplanes, with the best pilots for the best customers. We also are a young company. In 2009 and 2010, we really learned how to run a business efficiently. By 2012, Silver Air started to take off.

ST: You hired an old friend.

Jason: Yes. Kerry Classen in one of my pilots.

ST: I was sad to read that one of your children died.

Jason: Our daughter Emory Grace died in 2010. She lived for about 2 and a half months. She was on life support and never left the hospital.

ST: How did you cope?

Jason: We were devastated. My wife couldn’t even function for a year. I had a company in crisis so I went back to work. That was actually good because it gave me something to focus on.

ST: What led you two to start a charity for parents who lose a child?

Jason: Tricia always wanted to do something to make a difference in people’s lives based on what happened to us. We found there was all kinds of support for sick kids in hospitals, but very little for parents who lose very young children. Tricia decided to start the Emory Foundation to support people who lose a child. We get parents to counseling and hospice care. We lay out the whole thing. Once your child passes away here is what the next week looks like. What do you do? How do you do it? Part of the problem was funding. We were looking for a way to fund it.

ST: Where did you look?

Jason: For seven years I had done a local bike ride called the Santa Barbara Century. It was run by people who were looking to do something for a good cause. They didn’t raise much money and they didn’t really know how to. So I asked to get involved.

ST: What did you propose?

Jason: I told them Silver Air will be the title sponsor and we would raise money for the Emory Foundation so it gets us involved in something I’m passionate about. I brought Tricia to run the event because she had the background in sports production with Eco Challenge. Last year we rebranded it the Santa Barbara 100 and raised about 100 grand for charities. This year our goal is $250,000.

ST: What do you do for fun?

Jason: Now I ride my bike twice a week. Aiden my son is getting into bike racing. He just started riding for a little junior team in Santa Barbara called Echelon. They have really good coaches and really good group of people in support . We are trying to get them sponsors and make it a little more organized.