Ask a Genius: How Scott Keyes built his 'cheap' hobby into a business

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Ask a Genius: How Scott Keyes built his 'cheap' hobby into a business
Scott Keyes and his co-founder Brian Kidwell

So you love to travel, but you hate shelling out hundreds (or thousands) for airfare. You spend hours looking for inexpensive flights, only to come up short. You hear about someone scoring a low-priced trip and wonder, “Why can’t that be me?”

You can actually become that person with the help of Scott Keyes.

Known as a “professional cheap flight finder,” Keyes created and runs Scott’s Cheap Flights, a company whose sole mission is to (you guessed it) find you cheap flights. It’s a membership service that alerts you every time flight deals pop up. All listed flights are 40% to 90% off their normal price.

We sat down with Keyes to chat about his company, money and being cheap.

Our conversation with Scott Keyes is the latest edition of Ask a Genius, our regular series of talks with brilliant people. This interview was edited for brevity and clarity.

Did you always know you were going to be a cheap flight savant?

I was never one of those folks who dreamt of being an entrepreneur. I was actually a journalist for many years. I wanted to travel more, but not without spending more than I needed to.

As my side hobby, I started getting really good at finding cheap flights. This culminated in 2013 when I found the cheapest flight I’ve ever gotten in my entire life. It was a non-stop flight from New York City to Milan for $130.

Milan wasn’t even on my radar. But for $130? Of course I was taking it.

When I got back from this trip I had a bunch of friends contact me asking, “Can you let me know the next time you find a deal like that, so I could get in on it too?”

I didn’t want to keep this all to myself. But there was no way I could remember everyone who had asked. I came up with a little email list. So that’s how Scott’s Flights was born.

What happened next?

Over the next 18 months, the list just grew and grew. Friends would tell friends, and it grew to about 5,000 people. It was incredible, but was also problematic, because all of a sudden with the email service I used I had to start paying. I didn’t love the notion of charging a fee, but I realized, “Clearly there’s a lot of interest. I wonder if there’s a business opportunity here.”

So I relaunched with a premium version, much like Spotify. I kind of took a gamble to see if people would be willing to pay a couple bucks a month. I was just trying to recoup my costs. And obviously it’s grown quite a bit since then. We have 1.5 million subscribers today around the world.

Why is looking for flights so annoying?

The problem with buying flights is that it’s both irrational and unpredictable. They can jump up $1,000 in one day and go right back down again the next. It’s infuriating as a consumer because, how are you supposed to know when to buy? Is the price listed good or not?

Finding a good flight is like seeing a shooting star. It comes when you don’t happen to be looking for it, but it’s a magical surprise.

How do you view being 'cheap'?

As you probably won’t be surprised to learn from a guy who founded a cheap flights company, I’m a very frugal person. I’m very keen to find ways to not pay more than I have to. Of course I value quality, but I would rather pay the $130 for that flight to Milan than the guy next to me who paid $1,300. That’s a no-brainer.

There’s something quintessentially American about the fear of being a sucker, the fear that someone got the same thing as you for a much lower price than you did. I probably spend more time than I should getting the best price, whether it’s flights or lentils I’m buying at the store.

If I didn’t have this mentality, this whole dream wouldn’t have happened.

What will your future finances look like?

My wife and I just had a baby. So I’m in that brave new world with getting my baby on a plane without it being a total meltdown.

I’m an organizational freak, for better or for worse. But I’m not a person who has strict budget categories. I just like to keep an eye on everything. At the beginning of each month I’ll go back through all of our expenses and get a sense of what we are spending, and how that matches up with personal income and future long-term plans.

People are terrified of referring to themselves as cheap. I can admit it. It’s not like I don’t like spending money, but I tend to be more cautious. This is why I don’t feel the need to do any sort of limits on our budget, because I have that gut inclination to be frugal. We eat a lot of leftovers. Most of our baby’s clothes and stuff are hand-me-downs.

Do you ever splurge?

Probably when we host dinner parties and have friends over. I’m less inclined these days to go out and get rowdy at the bar, but I love cooking a big meal and inviting all our friends over. And trust me, you don’t have to be in college to be enticed by a free meal. Everyone loves free food.

So what’s the secret to finding cheap flights?

I’m going to tell you, but you’re going to be disappointed. The secret to cheap flights: All you have to do is spend 15 to 20 hours a day searching for them. If you spend that amount of time looking for cheap flights, you will find them, I promise you. Or we could just do the work for you.

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Image: Scott Keyes