Entrepreneurs Who Built Businesses Off Their Love of Travel

Quit your job to travel the world — it’s a reality for some and a pipe dream for others. And still others flip the cliché on its head to turn travel — or the business of travel — into their jobs.

Click through to meet seven entrepreneurs who successfully started their own travel companies, from a college grad who built a business out of emailing flight deals to his friends to a healthcare industry veteran using data science to revolutionize travel planning. They share how they got started, how they made money and what they wish they’d known at the beginning.

Scott Keyes, founder of Scott’s Cheap Flights, What his company does: Scott’s Cheap Flights is an email newsletter with both free and paid subscription options. It alerts subscribers to cheap flight deals in real time and has saved people more than $1,000,000 on travel to date.

How he got his start: “Necessity is the mother of invention,” Keyes says. As a recent college graduate working in journalism, he didn’t have a lot of money, but he wanted to travel. To make it happen, Keyes started immersing himself in guides, video tutorials and message boards on everything from credit card points to cheap flight hacks. It paid off in 2013 when Keyes found the best deal of his life: a nonstop round-trip flight from New York City to Milan for just $130. He remembers his palms sweating and his hands shaking, but he booked the trip before the deal disappeared — then jetted off to explore Milan, ski the Alps and visit Lake Como. Upon his return, Keyes was overwhelmed with colleagues asking him if they could let them in on the next deal he found, so he started an email list to keep his friends informed.

For the first 18 months, it wasn’t a business at all, “just a hobby that I did for fun in my free time,” Keyes says. By summer 2015, that email list had grown large enough that Keyes would need to start paying to send it out via MailChimp. The high level of interest prompted him to gauge how many people would be willing to shell out a couple of bucks for the service. His initial goal was simply to break even on the email-sending cost: Get 25 people to pay $2 a month.

How he turned a profit: The idea of convincing people to pay for something they’re used to getting for free concerned Keyes, so he set an extremely low price point at first with $2 a month. The first week was touch-and-go, but after a few weeks, he had made $100. After a few months, he and his co-founder realized that on $2 a month, “credit card fees are eating you alive,” Keyes says. At a standard 3 percent plus 30 cents per transaction, card companies were earning double-digit percentages on every transaction. They graduated to a longer-term subscription model to save on fees: $15 for three months, $25 for six months or $39 for one year.

His secret to success: “There’s a little bit of an illusion or a story we like to tell ourselves — that as soon as we get things up to a certain point, then we can stop working as hard,” Keyes says. Although that might be true for passive income such as ongoing book sales, it’s not true for business. “The more it grows, the bigger it gets, more people are relying on you,” Keyes says. It’s important to make sure you’re passionate about what you’re building.

What he wishes he’d known: Don’t quit your day job too soon and too early. There’s “real romanticism about the tireless entrepreneur who quits their job and liquidates their bank account” because they worked so hard at their dream, Keyes says — but you don’t hear as much about the startups that don’t work out. He kept in mind the idea that most startups fail in order to stay humble and to remind himself to be smart financially. It wasn’t until six months after Keyes made his first dollar that he stopped taking on freelance writing projects, and although he knew he’d never feel 100 percent ready, he advises gathering enough evidence that there’s a market for your product or service before jumping in with both feet.

Top consumer tip: Keyes says one lesser-known tool is the fact that if you book a flight directly with an airline, you’re entitled by law to a 24-hour no-fee cancellation period (unless the flight departs within a week). If you find a great deal, you can buy the flight, lock in the price for yourself and then decide whether to keep it. “In general, the better the price is, the shorter [the time] it’s going to last,” Keyes says.

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