Meet Josh: TPG’s winner of the trip of a lifetime

Oct 17, 2019

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Josh Kirdy has worked in the travel industry for the better part of a decade. But this summer marked the first time he stepped foot outside of the United States, when he and his fiancé Brandon visited Italy, Portugal and London for 10 days.

A longtime TPG reader, Josh credits The Points Guy for helping him figure out how to make the most of their bucket-list Europe trip. “I got the Chase Sapphire Reserve a couple of years ago, which totally changed the way I live my life,” Josh said. “We saw and experienced places I had only read of in TPG articles before.”

Thus, Josh was literally stunned speechless last week when he hopped on a video call and saw the Points Guy himself, Brian Kelly, live on his screen. “Prizeo reached out to tell me, ‘You’re one of the finalists, and we would like to talk with you,'” Josh said. “All of a sudden, I’m on a call with Brian Kelly.”

The shock didn’t end there: After some gentle trolling — “You’ve won 2,000 expired Spirit miles” — Brian informed Josh that he had won the grand prize from TPG’s 2019 fundraising campaign: the trip of a lifetime, using up to one million Chase Ultimate Rewards points, which would be personally planned by the original Points Guy.

“I feel like I won the lottery,” Josh told TPG. “It’s unbelievable. I’m still shocked.” In fact, Josh was so silent that Brian quipped, “Do you know what you can do with a million Chase Ultimate Rewards points?”

But Josh didn’t donate with personal gain in mind. While winning epic giveaways and traveling to Europe are new experiences for Josh, philanthropy has been a big part of his life for a long time. “I had made a resolution a couple of years ago to donate to more charitable causes,” Josh said. “I round up my change at the grocery store and so forth. So when I saw TPG’s fundraiser back in June, I thought, ‘Absolutely — no problem, I’ll donate.'”

“I’ve followed The Points Guy for a really long time, and he’s really someone I have looked up to for quite a while,” Josh said. “It’s really great to see him doing so many great things for organizations like Rainbow Railroad, and using his resources for a good cause.”

Rainbow Railroad’s mission of rescuing persecuted LGBTQ+ individuals worldwide has a very personal connection for Josh. “When I came out at 18, I was fortunate enough to be accepted by all of my family and all of my friends,” he told TPG. “I’m very lucky because of that. It breaks your heart to hear of individuals losing everything because they finally worked up the courage to be the person they are and know they are.”

“I was able to get through that time because of my friends and my family and all of the people supporting me,” Josh said. “So I always want to do anything I can to help others get through that. It’s really cool to see an organization like Rainbow Railroad do what they do.”

Josh’s life story is intertwined with travel and hospitality. A Florida native, he began working at Universal Studios while still attending college at the University of Central Florida. After graduation, he continued working his way up the theme park’s corporate ladder for eight years. In fact, Josh even has his job to thank for Brandon, who works in marketing for Sea World: The two met at a theme park expo several years ago.

Outside of work, Josh volunteers his free time with Give Kids the World, an organization that hosts families visiting Orlando through the Make-A-Wish foundation. A seasoned veteran of the hospitality industry, Josh usually takes on the role of welcoming families to Orlando. “I meet them at the airport, help them get oriented, get their bags, get their rental car and answer any questions they have about their trip,” he told TPG. For many families, “there is a healing power that comes along with just getting away. And it’s an honor to welcome them and be a part of that experience.”

Josh is no stranger to the exhilaration of escaping through travel. “I love flying,” he told TPG. “Aviation and theme parks — they’re kind of my sport. As a child, Mom and Grandma would take me to the Fort Myers Airport in southwest Florida to watch planes take off and land.”

But this self-avowed AvGeek is still looking forward to many aircraft experiences to come. “I had never been on a widebody aircraft before our flight to London this summer,” Josh told TPG. “We ended up on Norwegian Air’s all-white Airbus 330, and the premium cabin ended up being more like first class with lie flat seats.”

Josh has the iconic Boeing 747 and Airbus A380 on his AvGeek list of must-haves. “It would be incredible to get into a business class or first-class seat on one of those amazing planes,” he said. And — as Brian said on their call — now Josh can, thanks to his amazing grand prize.

“Brandon and I are planning our wedding for September 2020, so this prize couldn’t have come at a better time,” Josh told TPG. “I love nature, and I’ve always wanted to see Africa, so that would be so cool.” Although the couple have yet to plan their trip with Brian, Josh believes he and Brandon would be happiest with a shorter honeymoon, focused on quality over quantity: “We’d want to get the most out of our journey there, wherever we go, working those bucket-list flights into the whole new itinerary.”

While Brandon isn’t as much of a plane buff as Josh is, he makes the perfect love interest for an AvGeek. “Brandon tries to stay interested in aviation for my sake, and sends me little articles here and there,” Josh told TPG. In turn, Josh brings the romance in his own way: “We got engaged on our five-year anniversary trip this year, in Lake Tahoe. We flew there for some snowboarding, because it’s just absolutely beautiful: The air is crisp, water so smooth, the mountains go on forever. Tahoe is where Brandon’s parents got engaged, so now it’s a special place for all of us.”

DONATE TO RAINBOW RAILROAD: Although the Chase sweepstakes has ended, you can still donate directly to Rainbow Railroad to help persecuted LGBTQ+ refugees. Each rescue costs about $10,000 on average

Watch The Points Guy surprise Josh here:

All photos courtesy of Josh Kirdy.

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