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Why the founder of Scott’s Cheap Flights wants you to take more vacations

Scott’s Cheap Flights founder Scott Keyes, right, and CEO Brian Kidwell. Keyes approached Kidwell to come on board as co-founder in late 2015. “I was not a savvy, aspiring entrepreneur,” he said. (Scott's Cheap Flights)
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When Scott Keyes answers the phone, he is giddy. It’s late April, and he has just found out about a ridiculous deal to Japan: $202 round trip, from several cities in the United States. “I’m so, so excited. Oh, man,” he says. “This has been like a week like nothing else I’ve seen in terms of the number of deals.”

At age 34, Keyes is a cheap flight hunter, to the extreme. What started as a hobby in 2013 has now grown into a business called Scott’s Cheap Flights, which employs nearly 40 people and has more than 2 million subscribers (there’s a free and a paid option) who are all interested in the same thing: getting great deals on airfare. Keyes’s personal and professional mission is encouraging people to take more vacations by traveling on the cheap. In fact, that is the title of his new book, which published earlier this month: “Take More Vacations: How to Search Better, Book Cheaper, and Travel the World.”

From Keyes’s excitement on the phone, it is clear he still gets a rush from the hunt, even when it’s not a deal he is planning to use himself. Take this one to Japan: He says it’s painful to pass it up, but he and his wife are expecting their second child soon, so he’ll settle for living vicariously through subscribers who end up purchasing tickets. (The site doesn’t sell plane tickets; it just publishes deals that his team finds.) “It’s just so exciting to see, especially after the past year where so many of us have not been able to get that joy of travel, to have an exciting trip to look forward to,” he says.

His hobby turned obsession turned business allows him the pleasure of knowing that cheap flights aren’t going to waste — and people are, indeed, taking more vacations.

Humble beginnings

Start-up stories often begin in a garage. Keyes’s story began with a trip to Milan. It was 2013, and Keyes was a 26-year-old freelance journalist. His income was low, but his travel aspirations were high. He knew cheap flights were out there, and he decided to dedicate himself to finding them. He dove into message boards and searched myriad sites and came upon a $130 round-trip ticket from New York to Milan. He had never even considered going to Milan, but at that price, he figured, why not? With that, he learned his first cheap-flight lesson: First find the deal, then plan the trip.

Four experts on cheap travel share their best tips for maximizing value while vacationing

When friends and colleagues heard him talking about the cheap Milan ticket, they wanted in on the secret. They asked him to share his future cheap-flight finds, so he started a newsletter for a small group of people. He didn’t yet see the business potential, though. “A savvy, aspiring entrepreneur would have realized in that moment, ‘Oh, my gosh, you know, there’s an opportunity here. This could be a business. People clearly want this thing,’ ” Keyes says. “But that was not me. I was not a savvy, aspiring entrepreneur.”

Over the next 18 months, friends referred other friends to the newsletter, and it grew from a few dozen recipients to nearly 400. In 2015, Business Insider published a story about Keyes and his cheap-flight pursuits, and, practically overnight, 5,000 people signed up for the newsletter, prompting the newsletter host service to charge him $50 because he had exceeded the contact limits in the free plan.

Here’s where the wheels start turning. Although Keyes hadn’t planned to make money off his hobby, he wasn’t willing to lose money on it, either. So he decided to try a little experiment and see if people would be willing to pay $2 a month to get emails about the deals. He was flabbergasted when, in the first month, 100 people signed up. And the next month, another 100 people signed up. “I felt like Scrooge McDuck, just like swimming through gold coins,” he says. “I could not believe what I had stumbled upon here.”

Keyes decided it was time to bring in someone more entrepreneurial than himself. He had recently met Brian Kidwell, a business-minded ideas kind of guy, who was also working in the travel start-up space. Keyes approached him to come on board as co-founder in late 2015. Around that time, Kidwell — who is now CEO, while Keyes has the title of chief flight expert — recalls they were bringing in about $2,000 per month from subscribers. Then, in February 2016, Condé Nast Traveler published an article about the site, and revenue shot up to $21,000. In May of that same year, they launched the website ScottsCheapFlights.com, and the reputation — and business — has been growing ever since.

Kidwell says one of the things subscribers appreciate about Scott’s Cheap Flights is its approachable tone, thanks to Keyes’s own personality. “People really felt like Scott was just this friend sending them deals that he found,” Kidwell says. “He really is that friend. He’s such an easygoing, laid-back person. He’s authentic, he cares about everyone that he interacts with, and he’s just an all-around good human being.”

The future of travel, according to Scott Keyes of Scott’s Cheap Flights

Brian Kelly, who is founder and CEO of travel rewards site the Points Guy, says Keyes is known for being a nice, knowledgeable guy who is doing exactly what he set out to do: offer advice on cheap flights. “I think what separates Scott from a lot of others in the travel space is he knows cheap flights and he sticks to it. Instead of trying to reinvent the wheel and monetize through other areas of the travel industry, he knows the flights world, he has a great team and technology stack to scour for those deals, and he delivers on that,” Kelly says, via email. “Overall, I think he is providing a great service to consumers to save money and to also get out there and explore destinations you might not have considered.”

Among travelers themselves, Keyes and his business — which devotees refer to as SCF — have developed something of a cult following. “SCF has totally changed the way I decide when and where to travel,” says Victoria Kelly, 59, who lives in Charleston, S.C. Kelly first subscribed to Scott’s Cheap Flights about four years ago. Before that, she says, she would find an occasional cheap flight from Charleston, but it might have three stops. When she started getting emails from SCF, she realized that there were incredible deals out there, and she just needed to change her approach to be flexible with her timing, destination and departure city. She ticks off the places she has gone with pride: New York to Rome for $220 round trip; New York to Paris for $300 round trip; Charlotte to Madrid for $274 round trip; Orlando to Munich for $350 round trip; Charlotte to St. Thomas for $85 round trip. “Whenever I see something, even if it’s not a city I want to go into, it’s like, well how close is that to something? Where could we go from there? What do we want to do with that?” she says. “Some women get excited about the shoe sales. I get excited about the travel sales.”

Dawn Taylor, 54, who lives in Kansas City, Mo., has also become an enthusiastic follower of Scott’s Cheap Flights. Since 2017, she has traveled round trip to Belize ($368), Seychelles ($685), Croatia ($401) Puerto Rico ($335), Montreal ($294) and Madrid ($429). Before subscribing to SCF, Taylor says she believed travel was expensive. Now, she takes two international trips a year, and booking the next trip is always on her mind. “If I don’t eat lunch out at the restaurant twice a week at work, then in four months it’s a plane ticket,” she says. “I’m constantly thinking in those terms.”

She is especially excited for her next trip: In 2022, she will be traveling to Tokyo for $280 round trip, having purchased one of the flights that Keyes was so giddy about.

Serendipitous discoveries

Keyes wants people to take more vacations. It has become his mantra, and he tells people they can do that by prioritizing cheap flights. “It’s not just the money that you’re saving, but it lets you take more trips, better trips. You’re happier after the trip, you’re happier before the next trip. It ends up bringing vacation back to its core, which is something that’s supposed to take away our stress rather than add to our stress,” he says.

Travel isn’t just about getting away from it all. It’s also about seeking. Cheap flights can be a portal to learning, discovering, meeting new people, finding new opportunities. In his book, Keyes talks about how he met his wife, Anya, thanks to cheap travel. At the time, he was living in Mexico and she was living on the East Coast, and they met and hit it off on a beach in Puerto Rico. They stayed in touch, and cheap travel allowed for regular meetups. It was on a cheap trip to Hong Kong — after hiking up Victoria Peak in the middle of the night — that Keyes asked her to marry him. Now, they have a 2-year-old daughter and the aforementioned child on the way.

So when Keyes has to pass up cheap flights — like the one to Japan — it may smart a little. But he can’t help but be grateful for all that cheap travel has already brought, beyond the trips themselves. And even though he can’t travel as much as he used to, he can still use his cheap-flight hunting skills for good, helping subscribers score inexpensive airfare and explore the world, never knowing which encounters could shape their lives.

Silver is a writer based in Chicago. Her website is thekatesilver.com. Find her on Twitter: @K8Silver.

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