This transcript was generated from the episode audio and may contain minor errors.
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Hello, greetings, what's up and welcome back. This is Noticeful School, I am your host, Chris Guillebeau. Got a story today about a little email list that grows to several hundred thousand subscribers, ends up becoming a seven figure hustle, which is pretty cool and it's all about travel. Now I love the topic of travel. For 15 years, I have been actively traveling all over the world.
In fact, I had a quest to go to every country in the world for about 11 of those years. That project evolved from my love of travel and goal setting, making lists, and people often have a lot of questions about it. So I wrote a whole book about quests called "The Happiness of Pursuit." But one of the questions people ask me about a lot is, well, how did you pay for that? How much did it cost? I go into a lot of details about that in the book and on my blog.
But the short version is that as part of the process, I learned a lot about what I called travel hacking, which was the art of seeing the world on a budget, using frequent flyer miles, mistake fares, round the road plane tickets and other creative strategies. And after a while, I kind of became obsessed with this world and I would spend a lot of time, way too much time, reading hundreds of forum posts and newsletters and blogs, searching for airfare, every chance I had. And today's story is about someone who's also obsessed with the world of cheap travel. As I said, this is a big success story. So in just a moment, you'll learn how a Washington DC political analyst used his travel skills to help other travelers save money while making more than a million dollars himself in building an email list of more than 275,000 people.
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And now our story. For many years, Scott Keyes worked as a political journalist in Washington DC. He wrote about topics ranging from voting rights to homelessness, but most of all, political campaigns. The job required a lot of travel to events and rallies around the country. And Scott realized from the beginning that frequent flyer miles would be a major perk of the job.
So he set about learning how to generate as many as possible and get the most value he could from them. He studied up on the basics of mileage earning and credit card churning, and pretty soon became a frequent flyer miles evangelist. Now, so far, Scott sounds a lot like me, but he's probably less annoying than me because I love to talk about these things. And whenever I meet someone who says they're taking a trip, I always have lots of questions for them about what airline they're flying. Then I have all kinds of comments about the aircraft, where the best seat is, which terminal they're connecting in, where to get the best coffee there, all this kind of stuff that probably 99% of people do not care about.
So I try to turn it off and only give advice when people want it. Okay, so back to Scott. Before long, Scott realized that all this information he'd been collecting about frequent flyer miles might be useful to others. He noticed, just as I did many years ago, that frequent flyer programs are often purposefully opaque since the airlines know that miles that aren't used are essentially profit to them. So they don't always want to make it super easy.
Therefore, Scott decided to start combining his day job of writing with his side hobby of travel. He first wrote a brief explanatory ebook on how to generate and use frequent flyer miles. That book was called "How to Fly for Free, Practical Tips the Airlines Don't Want You to Know." And it sold enough copies to buy a couple of beers a week, but that was about it. Fast forward two years, and he's now living what he calls a terrible journalist's life in Oaxaca, Mexico, and mostly working on a freelance basis. He decided to write a second ebook, which was called "How to Find Cheap Flights, Practical Tips the Airlines Don't Want You to Know," which was a very similar title to the first ebook.
And that one went over okay, but still it wasn't bringing in a ton of money. It really was just a little hobby thing he was doing. But in the midst of all this writing, he had developed a reputation among friends and colleagues as a travel expert. In 2013, he bought a ticket from New York City to Milan for $130 round trip. When he got back home, dozens of his friends asked him to let them know the next time he saw a fare like that so that they could jump on it too.
And rather than try to remember each person's name and information individually, he decided to make a very simple email list and just let everyone know it once. He called this Scott's Cheap Flights. And over the next 18 months, it grew by word of mouth from a couple dozen friends to maybe 300 people or so. But it's still just a hobby at this point. And then something really big happened.
Scott posted a map on Facebook showing his friends the two month trip he was planning to take with his girlfriend. This trip would go to 13 countries, include 21 flights, about 20,000 miles around the world, all for free using award tickets. Now, as luck would have it, one of those friends forwarded the map to a friend of hers at Business Insider who decided this sounded like an interesting article. She wrote a piece and it ended up going viral. Now, as a result, his sleepy email list for friends grew overnight from 300 people to 5,000 people.
This was a blessing and a curse. Because when you have an email list of 300 people, it's either free or it doesn't cost very much, maybe 20, 30 bucks a month. When you have an email list of 5,000 people, all of a sudden you're paying a bit more and he didn't want to pay out of pocket. And Scott loved doing this. He loved helping people with cheap flights, but he didn't necessarily want to pay to help them with cheap flights.
So he went on the two month trip and he didn't do anything right away, but he kept thinking about how best to monetize this opportunity. Should he use affiliate links? Should he have advertising? Something else. And he finally settled on a freemium model where anybody who wanted to could sign up for free as they'd been doing, but he'd also have a premium section with extra perks for folks who wanted to pay.
Now, as I said, this was in 2015 and the newsletter continued to experience tremendous growth at a very high rate. It's definitely abnormal and amazing that less than two years later, he now has more than 275,000 subscribers on that list that was just made for friends before it became a business and hasn't even been a business for more than 18 months. Okay, so what about the money? I mentioned this freemium model. People sign up for free.
He sends them a certain number of emails about fares he's found and it's legit content, like he's actually sending helpful information and it's not all a pitch to sign up for something else. But of course, there is that premium service with those extra perks. You can customize which destinations you're looking for. You can filter your results, get more or fewer sent to you. And because he was delivering good value, a lot of people really did sign up for the premium version over time.
Now, specifically around last fall, he did a really big Black Friday promotion to try to convert more free subscribers to premium subscribers. And the free list at the time had been about 204,000 free subscribers and with the promotion and some other things he'd been doing throughout the year, he had pushed his premium subscribers all the way up to more than 29,000. And after Black Friday ended, he had generated more than $960,000 in sales throughout the year, pushing it over the seven figure mark before the end of 2016. The site now employs several people, but Scott continues to spend a big part of his day searching for those flight deals and sending them out to his small list of friends, which was 300 and is now approaching 300,000. [Music]
So what an amazing success.
As I said, it certainly doesn't always happen this way or even usually happen this way, but it is really cool to see a small topical email list grow to the point where it's making a million dollars. Fantastic. Now, I also think even though Scott and I have some things in common, we have similar interests, but different personalities because I often talk about the strength of doing more than one thing, but this is a great example of someone who is a bit different than me and has been extremely successful in focusing on that one thing. On the landing page for his website, it says Scott searches for cheap flights all day every day because he has no life. Well, I don't have a life either, but I do more than one thing.
When I asked him what's coming next, he said, "My plan is to continue scouring for cheap flights like a hungry dog, improving the features and customer experience at Scott's cheap flights, all while I continue to travel the world." So I love that narrow focus and I totally respect it. In the show notes today, you can learn about Scott's cheap flights, maybe join his newsletter list if you want. You might not be an obsessive like Scott, but you can learn from him. Remember, inspiration is good, but inspiration combined with action is so much better. If you wanna see those show notes for today's episode, they're on sidehustleschool.com/5151.
And if you're curious to learn more about travel hacking, how I was able to go to every country in the world, how you can quickly earn a lot of miles for yourself, I'll include some links with info on those things as well, including a trial offer for a service I founded several years ago called Travel Hacking Cartel. I hope you enjoyed this episode. I hope you get your own cheap flight to wherever you want to go in the world. I'm probably on an airplane today because that's what I do. I'm Chris Guillebeau, this is Side Hustle School, and I'll see you tomorrow.
