“There’s Something Exquisitely American About the Fear That the Guy Sitting Next to You Got a Better Fare Than You Did”
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Welcome to the next installment of our interview series where folks share their thoughts about Big Travel with Small Money!
Miles & Points Interview: Scott’s Cheap Flights
How and when did you start collecting miles and points?
After graduating college, I needed a credit card. I knew nothing about which one to get, but I liked traveling, so I figured why not an airline card? I got an American Airlines card with a 50,000-mile sign-up bonus, and didn’t think much about it.
Fast-forward 6 months. My friend was doing research down in the Galapagos Islands and encouraging me to visit. When I took a look at flights, Expedia may as well have slapped me in the face. They were $1,600! Mind you, I was just out of college. That was a small fortune I did not have.
Then I remembered my 50,000 American Airlines miles. I’d never gotten an award ticket before, but hey, I had a college degree, I could figure this out. So I read a few tutorials online (shout-out to the Million Mile Secrets Beginner’s Guide!) and managed to find an award ticket down to the Galapagos for 35,000 American Airlines miles round-trip. Struggling against disbelief, I booked it.
Even as I got to the airport, I figured there must be a catch. They were going to deny me boarding, or ask for an additional $500 to get on the plane. Only after none of those things happened, and I got back from an amazing week swimming with sea lions, did I realize how opportunistic collecting miles could be.
Why did you start Scott’s Cheap Flights? What’s special about it?
In 2013, I got the best deal of my life: A nonstop flight from New York City to Milan for $130 round-trip. Milan hadn’t even been on my radar at all, but for $130 round-trip, there’s nowhere in the world I wouldn’t go. And it turned out to be an amazing trip! Went skiing in the Alps, saw an AC Milan football match, hiked Cinque Terre, hung out on Lake Como. It was fabulous.
When I got back, word spread among friends and coworkers about the deal I got. Friend after friend feigned interest in how my trip was, before getting to the real question: would I let them know next time I found a fare like that so they could get in on it, too?
So rather than try to remember a long mental list of people I was supposed to alert when a great deal popped up, I decided to start a simple little email list instead so I could alert everyone at once. Scott’s Cheap Flights was born.
For the first 18 months, it was just a little fun hobby I did for my friends. Purely for the love of the game. It wasn’t until August 2015 that it’d generated enough organic growth that it made sense to think about turning it into a business.
What’s the one thing people can do to get more miles or cheap flights?
Since most interviewees discuss miles, I’ll tackle the cheap flights perspective.
The most important thing people can do to get more cheap flights is patience & booking quickly when there’s a good deal.
Let’s say you want to bring your family of 4 from Des Moines to Rome. Typically, those flights would cost ~$1,200 apiece, or ~$4,800 total. Yikes.
But you’re smart, and started looking at prices 6 to 8 months before you wanted to travel, rather than the last month or 2. Though the price seems to stay put every day at $1,200, and you think about a long road-trip up to Chicago to get cheaper flights out of O’Hare, you’re patient. You know that every 4 to 6 weeks or so, a massive (unadvertised) sale ~$400 round-trip to all over Europe pops up from nearly every US airport.
Sure enough, like clockwork, another huge Europe sale comes around and flights from Des Moines to Rome dropped from $1,200 to $420. Your family’s flights now cost $1,680 rather than $4,800 the day before. These unadvertised sales often only last a few hours, so you jump on it quickly, knowing that because you booked directly with the airline you have 24 hours to cancel penalty-free if you wish.
Typically for international flights, you want to book around 2 to 6 months ahead of travel. (Add a couple months if you’re going during peak summer, Christmas, or New Year’s). If you get antsy and book a not-great fare too early, you’re locked in at a much higher price than might be available later. And if you’d waited too long to start looking at fares, you won’t have enough remaining time to be patient and hope for a cheap flight to pop up.
What’s your most memorable travel experience?
For me, the most memorable travel experiences are the unexpected ones. I’m not as into the bottle of wine near the Eiffel Tower as I am the bizarre encounter in the backstreets of Bangkok.
In 2016, my wife and I went to Belarus to visit her family. The trip got off to a rocky start, because until very recently Belarus required visitors to jump through an absurd number of hoops to get a visa — one of the primary reasons Belarus is the least touristed country in Europe.
Relieved to have made it in, our first day in the country we visited The Stalin Line — a “park” that consisted of a big open field filled with old discarded and retired Cold War-era Soviet weapons. Think machine guns, missiles, and tanks, along with large bronze statues of Stalin and Lenin.
As fascinating as it was to see all these weapons that had once been manufactured for possible use against the US, the real gem was the park’s secret menu of offerings. Like In-n-Out Burger but for retired military hardware.
For example, in perhaps the most delightful scene I’ve ever witnessed, I saw a small group of tourists from Asia hand a park operator a few bills. And then they climbed on top of a WWII-era tank. I thought they were just going to take photos, but a few seconds later the tank lurched forward.
Pretty quickly, it was up to 25 or 30 miles per hour, zipping around the entire park. These tourists were having the time of their flipping lives, and it gave me so much joy just to watch them. Photo and video.
What do your family and friends think of your cheap travel hobby?
They love it.
There’s something exquisitely American about the fear that the guy sitting next to you got a better fare than you did. After all, nobody wants to be a sucker.
So for family and friends, having someone they can consult on any given airfare is very much appreciated.
Is there any tool or trick which you’ve found especially useful in this hobby?
I’m gonna let readers in on the honest-to-God secret to finding cheap flights: Spend 16 hours a day, every day, on Google Flights.
The thing about cheap flights is their timing is unpredictable. The best fares are during unadvertised sales — and that’s not even mentioning the mistake fares that occasionally pop up — which by their nature are not publicized, and can arise anytime. On top of that, in general, the better the fare, the shorter it’s going to last.
So the key to finding cheap flights is to be constantly looking and find the unadvertised sales before they disappear. Some people get a real thrill out of spending hours a day searching on their own, but it’s not for everyone.
That’s a big part of why Scott’s Cheap Flights has had a modicum of success: most people would rather outsource 16 hours a day on Google Flights to us rather than doing it themselves.
What was the least expected way you’ve found a cheap flight?
Buying a $170 round-trip flight on JAL from Taiwan to California (We lived in Colorado at the time).
When I stumbled across this fare in early 2016, I wasn’t going to let the fact that I didn’t live in Taiwan or California stop me from buying a $170 round-trip flight across the Pacific. So my fiancée and I booked this deal, setting our outbound date for October 2016 and our return flight in February 2017.
We used miles to for a one-way award flight to Japan in October, spent an awesome week in Tokyo, then hopped a budget flight down to Taiwan to start out $170 round-trip flight. Come February, we went back to Japan on the return portion of the $170 ticket, skipping the final leg from Osaka to Taipei and spending another week in Japan. Another simple one-way award ticket brought us back to the US. (The Southwest Companion Pass helped us get cheaply between Colorado and California.)
Not the simplest 2 trips to Japan, but for the cost of one round-trip award ticket and $170, it was 100% worth it.
What do you now know about booking cheap airfare which you wish you knew when you started out?
How prevalent cheap flights are if you’re patient and flexible. Now that we spend 16 hours a day every day searching for cheap flights, it’s genuinely shocking how often they pop up.
Airfare has never been as inexpensive in the history of flight as it is today. How lucky are we all to be able to regularly travel round-trip to Europe, Asia, etc. for under $450 round-trip.
The flip-side of that is the increased urgency to not settle for just okay airfare. Start planning well in advance, be patient, and book $450 flights to Paris rather than $900 ones.
What would your readers be surprised to know about you?
How debilitating it can be to know all these cheap flights exist! My goalposts have completely shifted, and now I’m incapable of spending more than $400 for a round-trip flight to Europe or Asia. It’s a good problem to have, I suppose.
Any parting words?
It may sound corny, but it’s legitimately an honor and a privilege to send cheap flights to subscribers for a living. I wake up every morning on a treasure hunt for airfare, and get to live vicariously when subscribers book cheap flights.
And as gratifying as it is to read success stories from 1,000s of subscribers who didn’t think they could afford to travel internationally until we found $390 flights to New Zealand, you all have made my dream job come true. Thank you!
Scott – Thanks for sharing your thoughts on Big Travel with Small Money!
If you’d like to be considered for our interview series, please send me a note!
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