Meet the 29-year old American man who turned his obsession with finding cheap airfares into a million-dollar business

 "I have a weird job. I find cheap flights for a living". That's how Scott Keyes introduce himself during the recent Reddit AMA he hosted. Within three years he succeeded to turn his obsession for finding cheap flights into a million-dollar business. And from a freelance journalist, writing for The Guardian, ThinkProgress and The Nation, now he is the founder of six-employee start-up called Scott's Cheap Flights and an email newsletter with almost 350,000 subscribers.
Everything started when in 2013 he found an amazing deal to fly nonstop from NYC to Milan for $130 roundtrip. When he got back, all his friends wanted him to alert them next time a deal like that popped up. So he created a newsletter where his friends could sign up to get alerted. Soon his 300-person list ballooned to 3,000 and all of a sudden he was hit with hosting fees. "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. Rather than making payment mandatory, though, I decided to go with a freemium model that would consist of: A premium list for people to receive all the deals, especially the best ones, for $3-$5/month. For people who didn't want to pay, I'd keep a free list going, but only send 1/3 of the deals there", wrote he in a post for Reddit. Right now there are 350,000 people now on the list, including approximately 40,000 paying subscribers.

I talked to Scott to find out how he turned his passion into a successful business, how we could find cheap flights and what are the best days to fly. 

 

Scott, how did you end up working as a cheap flight finder?
When I graduated college in 2009, I knew two things: (1) I wanted to travel the world; and (2) I was never going to be wealthy. So if I wasn't going to let #2 prevent #1, I knew I would have to figure out some creative ways to travel without spending my life savings. I began reading up on flight pricing economics, spending hours on various flight search engines, and learning various patterns about flight prices that could help me avoid paying thousands of dollars to travel overseas.

Are you doing this as a full-time job now?
Yep! There are now 6 people on the team, and I've learned pretty quickly that running a startup is more than full-time work.

Is the searching manual or automated? Are you doing all the searching alone or you have hired staff to help you?
It's all manual. There are complicated reasons why automation doesn't work super well for flight searching, so I do all the searches by hand. We've got two other flight searchers on the team, Nicole who covers Australia/New Zealand and Katie who covers Europe. I cover the US and Canada.



How did you turn your obsession into a million business?
A lot of luck and a lot of persistence. My business partner and I have devoted thousands of hours to the business and building it out. I think the key is that it has broad appeal. Everyone loves to travel, and everyone hates paying full-price for flights. Establishing a business to alert people when cheap flights pop up, in retrospect, feels like a no-brainer.

How many premium and free subscribers do you have now? What’s the fee for premium subscribers?
There are 350,000 people now on the list, including approximately 40,000 paying subscribers. The fee ranges from $3-$5/month, depending on how long you sign up for.

Do you cover flights from everywhere, for example from Bulgaria?
Yep! We cover flights departing everywhere in Europe, the US, Canada, Australia, and New Zealand, and we're about to expand to cover Asia and Latin America.

What are the top 3 best deals you’ve sent to you premium subscribers lately?
Departing Europe, the best recent deals have been €280 return to Tokyo, €306 return to Australia, and €224 return to NYC.

How many of the paid subscribers have booked a trip in result of your help as far as you know? Thousands. In the past 6 months alone there have been 2,263 people who bought cheap flights because of the list and told us about it. Most of them are bringing others, and likely far more people bought tickets that we don't know about.



How exactly do you find so cheap flights? What we, the regular passengers, miss when we look to book a flight?
My two favorite tools to search for flights are Google Flights and Momondo. There are also some more complex ones like the ITA Matrix, SkyScanner, and various plugins, but all the tools are publicly available. The reason why Scott's Cheap Flights has enjoyed some popularity, I think, is that unlike most people I enjoy spending 6-10 hours every day searching for cheap flights. I've developed some expertise and know patterns about how/where to find cheap flights now that I didn't know a few years ago, but anyone who's inclined could develop expertise in finding airfare, just gotta put in the time and effort on flight search engines.
The thing most people miss when searching for cheap flights is to be flexible with your cities and your dates. This is the way most people approach getting a flight: (1) pick where they want to go; (2) pick their dates; and (3) see what prices are available. Typically this results in high prices. Instead, if getting a cheap flight is your priority, flip that approach: (1) see what prices are available via Google Flights, Kayak, etc. to various places are around the world; (2) decide which of the cheap destinations appeal to you; and (3) select the dates you like that have the cheap fares available.

Are you relying only on airlines making mistakes? Why don’t they correct them?
Nope. I'd guess about 5-10% of the deals we send out are "mistake fares." The rest are unadvertised sales or other significant price drops. The mistake fares do get corrected, eventually, but the key is to find out about them early enough so you can book them before they disappear. This is one of the main services Scott's Cheap Flights provides.


Do the low-cost airlines make such mistakes too? Could we find good deals there?
Sometimes, but less often. They tend to have newer computer technology their company runs on which is less prone to make errors as legacy carriers.

Are the flight deals you offer typically last minute deals?
I rarely send out last-minute deals. Most of the deals I send out have availability 1-10 months in advance.

Which are the cheapest days to fly?
Tuesday, Wednesday, and Saturday. Doesn't matter what day you buy though.

How many countries have you visited on this base – airline mistakes?
I've visited 42 countries in my life. 5 of those countries were on mistake fares. Buy me a coffee