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Is Roy Riley the Luckiest Man in Tri?

After winning a sweepstakes entry to race in Kona, this P.E. teacher lost his motivation to do the sport. After winning another contest, he's back for good.

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In 2011, physical education teacher Roy Riley saw an ad on social media for a contest. The prize: a free entry to an Ironman race. All he had to do was answer one question: “Why do you want to do an Ironman?” 

The question made him pause. As someone who raced sprint and Olympic distances locally, he had never really thought about doing an Ironman before. But as he thought more about it, he saw an opportunity to inspire the kids he worked with every day.

“I thought about the school I taught at,” Riley explained. “The students were troubled and had a much rougher upbringing than I could have imagined. Children with social and emotional issues, many disabilities and behavioral issues. The children actually live at the campus school full-time with staff caregivers. I wanted to inspire them to accomplish a goal. For me, that goal was Ironman.”

Riley submitted his entry to the contest, but months passed with no word. He had all but forgotten the contest when he received a phone call from the Ironman World Championship broadcast team at NBC. If he was up for the challenge, they had a spot for him on the Kona pier. There was only one catch: the race was six weeks away.

Riley didn’t hesitate. “I knew right then I was going to the biggest triathlon in the world.” 

Most triathletes have a few years of training under their belt before they go to Kona. That wasn’t the case for Riley, who had to scramble at the last minute to prepare for his debut Ironman. “Central Illinois wasn’t Hawaii, and I definitely never rode 100 miles before,” he said. In the weeks leading up to the race, Riley built his mileage up to 80 miles, then hoped for the best once he got to Hawaii. 

RELATED: Triathlete’s Complete Guide on How to Train For an Ironman

“I had no goal but to finish for my students,” Riley said. “I bought whatever the cheapest bottle nutrition I could find and did my weekend rides with it. I bought the cheapest salt tabs I could find online. I made a plan for 700 calories an hour on the bike for nutrition, having no clue if that was a good number. A pack of fruit snacks were 100 calories apiece, so I duct-taped an entire box to my bike on race day. Was I training properly and eating what the other racers were? Absolutely not. I was doing what I was used to up to that point.”

In a multisport fairytale that certainly seems made for TV, Riley had the race of his life. Somehow, despite a less-than-perfect preparation for racing a full Ironman, he finished the Ironman World Championship race in just over 11 hours.

(Photo: Roy Riley)

He was lucky, and he knew it. He had accomplished his goal, inspired his students to do the same, and was riding high. Which is why, after Kona, he fell out of triathlon altogether.

“It was hard to get pumped about a local sprint triathlon after doing Kona,” Riley said. “The motivation just wasn’t there for me after that.”

For ten years, he fulfilled his athletic pursuits elsewhere—mostly obstacle course racing and CrossFit competitions—with no thought of returning to triathlon. But one day, ten years after his Kona race, a new coworker began talking about signing up for a 70.3 event. She asked if Riley had ever considered getting back on the bike, and he said he’d think about it. Then, a few months later, he saw another post on social media that piqued his interest, same as ten years before: Triathlete’s Hawaii From Home free virtual event, where athletes covered the distance of an Ironman triathlon over the week of what would have been the Ironman World Championship.

“Once I saw Hawaii from Home—10 years after I did Kona—I thought, why not?” he said. “Will I ever make it back to Kona to compete? Honestly, probably not. But I can train and enjoy the process again.”

By signing up for Hawaii from Home, Riley was automatically entered into a random drawing for one of the prizes from the event. When he saw an email from Triathlete editors, he opened it and discovered he had won again—this time, a personal coaching call with Ironman legend Mark Allen.

“Lightning isn’t supposed to hit someone twice, and it has for me,” Riley said. “A call with Mark Allen? I have read IronWar multiple times, I have watched film clips of him. The timing was what was just as crazy; it was exactly 10 years to the day of my Kona 2011 event.”

He describes his call with Allen as “two buds chatting about something they both enjoy.” They talked about events, finding time to train with young children (Riley is a new father), and how to prepare for a full Ironman—this time, with more than six weeks’ notice. Once again, Riley is all-in on triathlon.

“I was trying to teach a lesson on goal-setting for my students in 2011. I am still doing that, but now it is also showing the health and fitness lifestyle to my son as well,” Riley said.

RELATED: Getting Ready for a 70.3? We Got You Covered!