How a 29-year-old turned an obsession with cheap plane tickets into a $1 million business in under 2 years

A 29-year-old turned an obsession with cheap flights into a million-dollar...

In 2013, Scott Keyes found a nonstop, round-trip plane ticket from New York City to Milan for $130. He knew the deal was a massive score. What he didn't know at the time was that his cyber bargain-hunting would turn into almost seven figures, a five-employee start-up and an email newsletter with almost 250,000 subscribers.

When Keyes, now 29 years old, returned from Milan, his friends were desperate to know how they, too, could secure such jaw-dropping deals.

Some of his most brag-worthy finds include round-trip tickets to Kenya for $310, Rio for $363, the Azores for $271, Copenhagen or Oslo for $279, and Bali for $348. (Azores, in case you are wondering, are a group of islands that are a Portuguese archipelago in the mid-Atlantic.)

Scott Keyes in Milan. His $130 round trip plane ticket was the catalyst for his business.
Courtesy of Scott Keyes

Keyes agreed to share the deals with his buddies. To streamline the notification process, he set up a newsletter to which his friends could subscribe. Just a couple of years later, the newsletter was a thriving business.

In April 2015, a reporter at Business Insider heard about Keyes' cheap plane ticket email list through Facebook and wrote a story about Keyes' flight searching prowess.

"Things just really lucked out on my end," says Keyes. "I never pitched [the piece] or honestly even thought of it as a newsworthy matter. Sometimes serendipity just falls into your lap," he wrote in a response to a reader question in the first of four "ask me anything" reddit sessions he has hosted over the past year.

Indeed. Nearly overnight, his email list of 300 jumped to 3,000.

Scott Keyes in Milan. His $130 round trip plane ticket was the catalyst for his business.
Courtesy of Scott Keyes

Because his email list ballooned above the Mailchimp threshold for free services, Keyes had to start paying to send out his newsletter.

"I'd never thought about charging to be on the list, but the hosting fees made it a necessity, so I wallowingly broke the news to the list," says Keyes, in a post he wrote about his journey for reddit. He opted to continue to send out a portion of his deals for free but to charge $2 a month for access to all of his deals.

The flight path from zero to a million

The premium list launched on Aug. 23, 2015, and after three and a half months, Keyes had 646 premium subscribers. He generated more than $6,000 with the newsletter, almost by accident. At the time he was still a freelance journalist, writing for the likes of The Guardian, ThinkProgress and The Nation.

The growth of his newsletter, aptly named Scott's Cheap Flights, hasn't slowed down. By February, Keyes had generated $24,376 in revenue with 1,687 premium subscribers and 7,847 free subscribers, according to his second reddit forum. By this time, he had also stopped working as a freelance journalist in order to devote all of his energy to growing his business, and he had hired his first part-time employee.

By May of this year, Keyes was up to 6,230 premium subscribers, 53,547 free subscribers and $120,013 total revenue. Currently, Keyes has 29,639 premium subscribers and 204,021 free subscribers (233,660 total) and, thanks to a Black Friday promotion, has now generated $963,234.48 in sales.

Frankfurt, Germany. Scott Keyes and his fiancee flew to Germany and Belarus for 60,000 United miles and $88 per person.
Courtesy of Scott Keyes

In total, Keyes has spent less than $500 in marketing, according to an email he sent CNBC. His growth has been driven by word-of-mouth, press coverage, flight giveaways and, of course, his four AMAs.

"This business would seriously be a fraction of what it currently is without reddit," says Keyes, in a forum on the website. "A sizable percentage of the current subscribership (is that a word?) is due to posting on reddit."

“Google Flights is my life.”

Keyes has built his mini empire by searching for the accidental cracks in the airplane booking system. Many of the deals Keyes offers are a result of what he calls "fat-finger discounts (someone priced it at $59 instead of $590)" or because of translation mistakes between airline partners.

Thus far, all the searching is manual labor. "Kinda crazy when I say it out loud, but Google Flights is my life," he says in one of his reddit posts.

Life on the road. Scott Keyes paused on his tour of the British Museum in London to analyze a great ticket deal.
Courtesy of Scott Keyes

He gets recommendations regularly to try automating the search process. But robots won't catch diamonds in the rough. Outsourcing the searching isn't feasible either, "because it's more of an art than a science. If it were easy to find cheap flights, this business wouldn't exist," says Keyes, in a reddit AMA on his start-up growth.

“It feels super weird to be the ‘boss.’”

As Scott's Cheap Flights newsletter has grown, he has had to staff up to keep up. Currently, he has four part-timers helping him out with the logistics of the newsletter, as well as the actual searching.

The growth of the start-up has been a bit of a whirlwind. "Anyone who knows me knows I'm not a businessman and never really had entrepreneurial aspirations, so it feels super weird to be the 'boss,'" says Keyes, who adds that he "shudders just saying the word out loud."

He is still shocked at his own journey.

Scott Keyes in Hierve el Agua, Mexico, on a round-the-world trip he took with his fiancee last spring. They flew 20,000 miles to 13 countries for 136,500 frequent flyer miles and $20 per flight in taxes and fees.
Courtesy of Scott Keyes

"I am completely blown away by how successful it's been. I started out in August 2015 charging $2/month for the premium list, and wasn't even sure I'd hit the 30 subscribers necessary to cover my costs. That there are now nearly 25,000 people who are willing to pay for this service is still hard for me to fathom," says Keyes in an email with CNBC.

Even as he marvels at his own success, he has ambitious global growth goals. Currently Scott's Cheap Flights is available for would-be travelers searching for flights departing from the U.S., Canada, Australia, New Zealand and every country in Europe. "We'd like to eventually be able to send out deals to people departing anywhere in the world," says Keyes.

Scott Keyes in Athens, Greece, on a round-the-world trip he took with his fiancee last spring. They flew 20,000 miles to 13 countries for 136,500 frequent flyer miles and $20 per flight in taxes and fees.
Courtesy of Scott Keyes

Keyes wants to convert more people to the joy of traveling. Working remotely from the road, from coffee shops, or from his home office in Fort Collins, Colorado, gives Keyes the opportunity to benefit from his own searching. "Oh man, it feels like I am always up in the air," says Keyes in an email with CNBC.

In 2016 alone, Keyes has logged 81,866 miles. He's been to Mexico, England, Spain, Hong Kong, Borneo, Bali, Singapore, Vietnam, South Korea, Germany, Belarus, Japan, Puerto Rico, Las Vegas, NYC, Chicago, DC, and Portland, Oregon (twice).

And he's interested in helping others do the same. "We'd like to keep unearthing mistake fares and super cheap international flights so even more people who thought they couldn't afford to take that honeymoon or visit that overseas relative will actually be able to do it," says Keyes in an email with CNBC.

Scott Keyes at the Olimpiyskiy National Sports Complex in Kyiv, Ukraine, watching a Europa League soccer game.
Courtesy of Scott Keyes