If you were Scott Keyes, you would never have to worry about breaking the ice in social situations. People would slide their arm through yours, linking elbows, and pull you gently to groups of movers and shakers, before asking, “Have you met Scott? Ask him about his flight deals!” You would smile politely, almost demurely — to make yourself seem approachable and not like some smug flight douche — then drop some anecdotal magic. “Well, there were the round-trip tickets to Copenhagen or Oslo for $279, the Azores for $271, Kenya for $310, Rio for $363, and Bali for $348. last week, so I’ll be on the road a lot this spring” And, that would be a sufficient amount of information to elevate you to the upper echelons of party guests. You would always have a full glass and an attractive conversation partner with blindingly white teeth.
In reality, Keyes isn’t spending all of his time flaunting his knowledge or exclusively hobnobbing with toothy world travelers. He’s too busy running Scott’s Cheap Flights, a website and email list that alerts subscribers to inexpensive flights. The former journalist is quite adept at deal spotting and his once small group of followers has expanded beyond friends and family, necessitating the introduction of paid subscriptions to finance the undertaking. Now, it’s a profitable business — thanks to travel industry insiders.
Scott’s newsletter may be one of the travel world’s best-kept secrets, but he isn’t crouched behind a curtain demanding that people pay no attention to him. He’s really open about the methods he and his team use to bring the best deals to their followers. Keyes has hosted multiple Reddit AMAs — giving people the answers they want about cheap travel. And, he sat down with us to talk about great deals, how to find them, and the destinations that offer the best value.
What do you say to a group trip to Lithuania? Let’s start planning now.
Can you give me a quick bio about yourself and your travel background?
Yeah, sure. I’ve always been really into travel, especially after college. I really wanted to be able to travel, and then, I looked at my bank account. On a good day, there were four figures on there. On a bad day, there were two to three figures on there. I knew, “Okay, if I want to travel, I’m going to have to figure out a way to do this without spending much money, because I don’t have much money.” I was a journalist for about four or five, six years after graduating. I knew especially as an entry level journalist, I wasn’t going to be getting rich on that. If I still wanted to travel, I was going to need to thread the needle on those two things.
Therefore, I started to get good at frequent flier miles and also searching for a flight. I developed little tips and trick. If you’re gonna buy a flight, what are all the different steps that you can take to make sure that you’re getting the best price possible for it? In 2013, all that culminated in my getting the best deal that I ever got in my life, which was a non-stop from New York City to Milan for $130 roundtrip.
I know! It was amazing. To this day, I still can’t believe I got to take that trip. It was funny because Milan wasn’t on my radar at all. It wasn’t a place I was dying to go to or anything. But, for $130 there’s nowhere that I wouldn’t go to. And so, I ended up having a great trip. I went skiing in the Alps. I went to a new HRM Soccer game. Went down, hiked Lake Tiempitera, Lake Como, all that sort of stuff. When I got back from that trip that all my friends and co-workers started asking me, “Hey, Scott. Can you let me know next time you find a deal like that, so I can get in on it too?” And then, rather than trying to remember each individual person I was supposed to tip off about these deals, I decided, “Alright, I’m just going to start a little email list.” If I find something decent I can just send it out to everybody at once.
That’s essentially how Scott’s Cheap Flights was born. It was just a little email hobby that I did for my friends sheerly for the love of the game. I just like finding deals and being able to help friends travel. For the first 18 months or so, it was a hobby, something that I did for fun. And it turned into a business, which was the furthest possible thing from my mind. There was never any plans or ideas for that. It wasn’t until about18 months later that it started to get big enough. There were, I think, 5,000 people on the list at that point. Just friends, friends of friends. Like, “Hey, this guy over here, he can find some really good deals. You should get in on this.” At that point, I started thinking, “Okay, maybe there’s actually something here. Maybe we can turn this into an actual business.”