June 17, 2021
DO YOU LIKE TO TRAVEL!?! Do you like unique business models?! Amazing. If you said yes to at least one of those, then today’s podcast interview is gonna make your week. Today we’re talking to the CEO of Scott’s Cheap Flights, Brian Kidwell.
If you haven’t heard about Scott’s Cheap Flights, we’d honestly be shocked. They’re a subscription email list company that sends out emails to their subscribers every month finding incredible deals on cheap flights.
Brian was a digital nomad who had always been interested in entrepreneurship and travel. After backpacking through Europe after college, Brian started a website focused on building a travel community where he would sell a bundle of deals on travel services. One thing led to another and Brian teamed up with Scott Keyes – the author at the time of a cheap travel ebook, and the two of them ended up founding Scott’s Cheap Flights which now has 30+ employees and around 1 million subscribers and growing.
Today we talk to Brian all about building Scott’s Cheap Flights. We ask him the ins and outs of an email list subscription program and how it works, building his team and company culture, how they navigated the pandemic in 2020 as a business built around travel, what he’s learned working with a business partner, and so much more. This conversation is not only fascinating and so cool, but it’s also incredibly inspiring as a business owner to think outside the box, be innovative, build a company mission and culture of honor and value, and so much more. I know I’m walking away ready to do more and do better and I know without a doubt you’ll feel the same.
Scott’s Cheap Flights is a travel subscription service that alerts subscribers to incredible deals for international and domestic flights. An average savings of $400-$500 per ticket for international flights and $150-$250 for domestic flights. It’s similar to a Spotify model, where there is a free tier and a paid tier that provides the full experience. For $49 a year people can sign up and get alerted on amazing deals, not have to search themselves, and save a bunch of money.
The limited list is their free tier that just gives everyone a sample of the deals that their premium members receive. Our limited members receive some of the deals and they’re not receiving all of their deals or best deals. And there are ads in their limited emails.
Their premium membership is geared towards anyone who travels once per year or more. Premium members receive all the deals that they find for the airports they follow. You can set your home airport and follow other airports as well, to receive deals only out of those airports. The premium membership receives domestic deals which the limited membership does not receive.
Emails are filled with mistake fares, which is when an airlines make a mistake and misprice a flight. Which can lead to huge savings, 90% below your typical cost on your flight. The last thing they send to their premium members is rare deals to destinations that you might not usually find deals for. The limited members receive a small sample of those.
Brian has always wanted to be an entrepreneur and run his own business. Always on the look for opportunities to start his own. Completing an entrepreneurship study abroad program in Barcelona in college, he tried to start a couple of businesses after but nothing took off. Feeling stuck he decided to take off for Europe in the hopes to spark new ideas! Not having a lot of money to spend he started Googling “how to find cheap flights” and found an ebook called, “How to Find Cheap Flights”. Purchased it and the next thing he knew he was backpacking Europe, visiting 14 countries in 49 days.
From his trip, Brian realized there were two areas everyone was always looking for advice on. One, people wanted to save money when traveling and two, everybody was always talking and asking for advice and insider tips on how to make their trips wonderful. Brain returned from that trip focused on starting a business in the travel space. He created a travel community focused on giving people discounts on travel products.
It was around this time that Brian received an email from the author of the cheap flight book that he had bought before his trip. That author’s name was Scott Keyes and is now his business partner.
The email he had received from Scott was saying for just a couple of dollars a month he could receive flight details straight to his inbox. Brian ended up buying a couple of subscriptions and then asked Scott if he could interview him to create content for his audience.
That is where Brian heard Scott’s story of finding a round trip ticket to Milan for $140 and when he returned all his family and friends wanted him to alert them next time there was a deal like that. Thus his email list began and slowly grew over time.
After their interview, Brian and Scott stayed in touch sharing feedback about different projects they were both working on. They then realized their skill sets complimented each other with Brian more oriented towards business and marketing and Scott an expert on all things travel. Scott then asked if Brian wanted to partner up and see what they could do with the cheap flight subscription. And that is how Scott’s Cheap Flights became.
It all started with Scott Googling searching and digging away. He was bored and was a journalist at the time and didn’t have a lot of money to travel. He would look for deals and ended up getting good at it.
The more you do something, the better you are going to get at it.
By the time they were going full-time on Scott’s Cheap Flight, Scott would spend 8-10 hours a day looking for cheap flights to send out. Then they grew a team, they got good at it, started finding other ways to find cheap flights and now they have built a lot of technology around that to automate the more route aspects on that so they can do it on a much larger scale.
Scott’s Cheap Flights are focused on showing the value of the premium membership in the free subscription, which is how they make money for the business. They want as many people to travel with their mission being to help people travel and experience the world. By continuing to send out deals for free, they can maximize their reach whether people sign up for the free or the paid version.
Many people like to try something out before pulling out their credit cards, which they completely understand. They find people hang out on the limited membership for a couple of days, weeks, or months until they want to upgrade to the premium. It also helps to have that amount of people telling other people about Scott’s Cheap flights, forwarding the emails, contributing to the community of people that support them.
As most marketing does, it has changed over the years for them. Early on they would see an article published that would send more people signing up their way. Now they have had to find more scalable channels, which is ramping up a paid advertisement for the first time. They also have an affiliate program, a referral program and encourage people to forward the emails. There are a lot of different parts of their marketing mix that play together, and once one of them is working well, it raises the others too. It’s a loop.
2020 was a very difficult year. Scott’s Cheap Flights had to fight for it last year. Their 2020 revenue was only down 5% compared to 2019.
When Covid began, they were only sending out international deals and weren’t doing domestic or any other deals. They had to move fast and ended up launching domestic to their premium members quickly to keep adding value to them.
Along with launching domestic flight deals, they started a couple of newsletters to keep the inspiration alive and the dream of traveling still there. Having advice about flights being canceled, when people could start traveling, all things Scott was expert on he started writing. The main hope was to help their members even if they weren’t paying them. It was a difficult time for all and they wanted to help everyone through it.
Everyone has their perspective on things should be handled, which is fair. Everyone has their perspective but then there is also the business side of things, trying to keep your employees, keep them paid, and continue to build.
Early on in the pandemic, Scott’s Cheap Flights sent out an email informing all their subscribers how they were going to handle it. They decided to send out deals that would be for three-four months out, focusing on airfare that is refundable and could easily be changed. They changed the deals that they were sending out to meet their members where they were at. Some people were still unhappy that they were sending out deals, but again a lot of it is the inspiration. That little moment in your inbox of this is possible.
For Scott’s, it is both. They were sending out so many great deals that nobody is going to be able to book all those deals. There has to be something besides just booking the deal that keeps people around. If you are going to take one or two international trips a year, you’re not going to book the 50 deals that we send you. There is something to that little mental vacation. When you see it in your inbox and you realize that that is possible for you, there is some joy at that moment, and keeps you sticking around looking for that.
Going back to the beginning it was just Scott sending out emails to his friends and family. There was no website to sign up for, it was a page on the website that he built for his ebook. Scott’s cheap flight’s email list, when they realized they were onto something and wanted to move it onto its website. They discussed renaming it, but every time they came up with something else it was already out there. Brian and Scott decided to call it Scott’s Cheap Flights and started to build everything around Scott.
The emails would say “love, Scott”. The emails would come from Scott, even though they were a team of 5-10. It was deliberate on their part and people still now email in saying, “Hey Scott, I am going to this place will you help me find a deal?”. Since then they have changed the approach and the emails are sent by “love Scott’s Cheap Flights”. In the beginning, they were trying to position themselves as that friend who happens to be the travel expert.
One, Brian highly values working with a business partner that is a lot different than himself. Not only in what they work on, on a day-to-day basis, but they’re different people. Because of their differences, they’re able to challenge each other’s thinking and have really good debates which continue to make them better.
Two is trust. The fact that they are different and can have debates and disagree, but are approaching it from a point of trust and they both have the same intentions for the business in mind. That is how they can come up with what they are and grow the business the way they are. Both trusting each other in the decisions they make even if the other person isn’t involved.
Scott’s Cheap Flights wants to make it a no-brainer purchase. If you push it higher, we start to do that debate in our heads. Right now you book one flight and it is worth it. $49 was the highest price they have had, they started it at $2 a month. They discovered the price naturally of what their members were willing to pay and overtime has gotten better and better at what they do as well.
First and foremost, if you are thinking about it, do it now, the sooner that you do it the sooner that will grow into a bigger business. If you have people paying you every month or year, that adds up into something significant over time.
As far as keeping your members around, a lot of it depends on having that open line of communication. That is one of the benefits that Scott’s has, people, write in and give them feedback whether it is good or bad. You can learn from that, have that connection, get better over time and continue improving.
Get started and listen to your members. It sounds simple, the advice is simple but the actual implementing and doing it can be more complicated.
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