Talking Points Episode 16: Finding Mistake Fares and Affordable Flights With Scott's Cheap Flights
On today's episode of Talking Points, host Brian Kelly, The Points Guy, brings on the CEO and founder of Scott's Cheap Flights, Scott Keyes. Keyes tells TPG why and how he started his company, shares some of the best mistake fares he's ever booked and explains ways outside of Google Flights to find cheap airfare.
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Brian Kelly: Welcome back to Talking Points. This is your host, Brian Kelly, The Points Guy. This episode may feature offers that are subject to change and are offered by our advertising partners. Thepointsguy.com is a free website, so we do advertise in order to generate revenue. For a full listing of our advertising policy, go to thepointsguy.com/advertising. Today we are going to talk all things cheap flights with none other than Scott Keyes, the founder of Scott's Cheap Flights. Scott, thanks for joining us today.
Scott Keyes: Thank you so much for having me. I'm excited to be here.
Brian Kelly: And, you know, I've been following your path for years. I feel like we somewhat grew up in the same era of, you know, people trying to maximize travel. When did you found Scott's Cheap Flights?
Scott Keyes: It was such a very serendipitous story because I was never the type of person who (was), you know, a budding entrepreneur or somebody who really wanted to found a company. I actually worked for years as a journalist in Washington, DC. And if you know anything about journalism, it's, you know, that most folks, at least in the political journalism world, don't go into it because it's super, super lucrative. You know, I ... look, I loved the work, I really enjoyed it, but I also wanted to travel. I was like, "OK, I need to figure out a way to thread this needle."
Scott Keyes: And so there were two, essentially, prongs that I approached with it. One was learning, you know, really deep diving into the points world, the credit card churning, you know, how to maximize all that. Obviously doing a ton of, ton of, ton of reading back on The Points Guy's archives and everything. And then another part of that was really sort of figuring out all the tips and tricks that I could use to try to get the best fare possible whenever I was going to book a flight. And so this then ultimately culminated in 2013 when I got the best deal that I've ever gotten in my life, still to this day, which was nonstop from New York City to Milan for $130 round trip.
Brian Kelly: Oh, was that that crazy ... Was that the Alitalia mistake fare?
Scott Keyes: This was the one that was on Widerøe. I don't know if you remember...
Brian Kelly: Norwegian site, right?
Scott Keyes: Yeah. Before Norwegian Airlines, this is the Widerøe one, you know the, the flights were on United, but you had to buy through Widerøe. Man, I'm so impressed at your memory that you remember this...
Brian Kelly: I remember the people ... I know people who then used that fare and then continued around the world. There were so many ways to exploit it and stretch it out even further.
Scott Keyes: I cannot tell you how heart-racing it was seeing these fares, trying to book them, trying to decide where to go. And the funny thing was, so I got this $130 flight to Milan, but Milan wasn't somewhere that had been on my radar. It wasn't somewhere I was super excited to go. It was just -- for $130, hell yeah, there's nowhere in the world that I wouldn't go. And so when I got back from this trip, you know, all my friends and coworkers -- I guess word had spread -- and they started asking me, "Hey Scott, can you let me know next time you find a deal like that so I can get in on it too." And so rather than trying to remember, you know, every single person that I needed to give a heads up to next time there was a great deal. I was like, OK, why don't I just start a simple little email list and that way I can let everybody know at once.
Scott Keyes: And so, you know, look, I didn't know it at the time. It wasn't something that I had a well-formed business plan or anything. It was just, look, I like finding cheap flights and I'm happy to do this for my friends. And it was something for the next 18 months was just a hobby. But then it wasn't ... It was something -- somewhere around summer 2015 -- that it had grown large enough that we're kind of 5,000 people or so on the list at that point and it had graduated me out of the free tier of MailChimp. So all of a sudden I had to pay for this. And I was like, ah, you know, I love doing this. I didn't love the idea of having to pay in order to send emails to my friends, but at the same time, look, there was a ton of demand for this. There were a lot of friends who'd told friends. Obviously it had grown significantly. And I was realizing ... I'm like, "Huh, I wonder if there's an actual business opportunity there." So August 2015 I relaunched it as an actual business and it's just been growing since then.
Brian Kelly: Awesome. Yeah. Actually there's a lot of parallels between, you know, The Points Guy's story. So I started in 2010 when I was in HR at Morgan Stanley, which you know, you don't go into HR if you want to get rich in this world. And I, I also love to travel, had no money and really started to just ... So I started the blog in June of 2010 as just a way to share, you know, the tips with my friends. Very similar to you. And I do ... You know, we still cover flight deals to this day. And I do remember vividly being at work and there was $143 ... it was a Delta, a mistake, to Stockholm and Copenhagen. And I remember the rush. Our top posts ever was, you remember that Etihad deal three years ago to South Africa for like $150 or whatever?
Scott Keyes: Yes.
Brian Kelly: So I remember it was Christmas Day, I was jet lagged in London and you know...
Scott Keyes: That was the Christmas day fare. I remember...
Brian Kelly: And I remember I was jet lagged at 6am and I was annoyed and I saw that come across the wire on Twitter. And at that point I ... I don't write that many blog posts anymore myself, but I was scrambling to get into the WordPress admin to share it and get it out. And you know that one went viral and people, people still come up to me and they're...
Scott Keyes: There's no drug in the world quite like that rush of knowing that you've got this mistake fare. It is time limited. You have no idea how long it's gonna last. And you got to get it out as quick as you can.
Brian Kelly: Well, we officially ... This is a podcast of two people who get drunk on cheap clients. So bring us ... So it's 2019, you've got to a team of people, some ... I even know some people who work for you. So how does your team ... How has searching for cheap flights changed as your team has grown and the airline industry has changed?
Scott Keyes: Yeah, you know, we are so fortunate right now to be living in what I call the golden age of cheap flights. It has never been cheaper to fly, let's just say for American audiences, to fly from the US over to Europe or from the US over to Asia as it is today in 2019. And so it is ... The thing is though, because airfare is such a difficult product for people to kind of wrap their heads around because it's not like, you know, you're buying a loaf of bread where you can kind of predict the price or the price is going to stay pretty similar day to day. It's always jumping around. It's so hard to predict. Because of that difficulty, people just frankly get very confused and don't know when to ... When should I book, where should I book? You know, how early?
Scott Keyes: And so that's all kind of a lot of the sort of ... In that atmosphere is where we really tried to insert ourselves and say like, look, because airfare's always jumping around and you never know when those really good deals are going to pop up, those $130 flights to Milan, those, you know, $300 flights to South Africa, and when they do pop up, you know that they're not going to last very long. Either you can spend, you know, 16 hours a day monitoring airfare, searching and searching and researching... most people, that's not their idea of a good time. I'm kind of weird that that is my idea of a good time. But it's like, look, you can do that on your own or we can provide that service for you.
Scott Keyes: And again, this is what I was doing for my friends. And then just kind of expanded on that as an actual business, where we just get our kicks out of searching, finding those little nuggets, you know, peppered throughout the flight search engines. And then when we do find those really, really good deals, putting it together in a little email, (to) let you know, "Hey, here's the fare we found," you know, how long we think it's going to last, the airline when it's available, and a couple of sample search links to get folks started.
Scott Keyes: So you know, originally, look, back in 2015 it was just me doing it and now there's about 40 people on the team, which is still mind-boggling. I can't believe it. I mean I definitely feel a lot of synergy with you [inaudible 00:08:03] obviously a couple of years ahead of me, but you've gone through that same sort of transformation growing up where it used to just be you, and now there's a whole team. And I don't know if you ever thought of yourself as, you know, being the boss or the one in charge...
Brian Kelly: I know a media executive that was ... I actually, for years we didn't hire that many people. I was like more people, more problems. I left corporate America so I could have freedom. But, it's ... I, today, in 2019, am having the most fun I've ever had with The Points Guy. And truthfully, I mean, we've got about 50 full time employees and about 50 ... there's 55 contributors and consultants and such that work on the business on a weekly basis. And we're launching in the UK and Brazil this year. So I'm like, you know what, let's just ride this wave. Let's have fun. And, so yes...
Scott Keyes: It's a fascinating thing because, you know, rewind nine years ago, I'm sure you never in a million years could have imagined ... 50 or 100 people and you know, growing it to the way it's heading. The things that you've had to learn, I'm sure along the way. Everything from managing people to, like, I'm sure some light coding or, or...
Brian Kelly: Yeah, SEO, the tricks of SEO and you know, our paid channels, how to pay to get the right customers. So I, yeah, it's such a multifaceted business.
Scott Keyes: I'm still to this day, that's a lot of my day to day -- learning and learning, and trying to do the best I can. But I'm the same way. You know, we kept things kind of bottled up for a while. I think in the first ... by, like, year two there were maybe 10 people on the team, you know, we were kind of very purposefully trying to grow slowly. And now you know, we're really kind of seeing the opportunity and sort of letting it [crosstalk 00:09:44]
Brian Kelly: I think it's better to grow slow in the beginning than to grow too big and overstretch yourself and then not be able to sustain it. So, hey, it's working for us.
Scott Keyes: Exactly. [inaudible 00:09:52] I didn't want to be so worried, you know, and get out ahead of our skis and then all of a sudden have this behemoth that couldn't be supported.
Brian Kelly: Before we keep going we're going to take a quick break.
Brian Kelly: So, talk to me. So today, so you guys still do a lot of manual searching for these cheap fares. So, you guys are like truffle pigs for cheap flights. How do you go about doing it? I'm sure people at home are like, "Give me the tips so I can do it."
Scott Keyes: So yeah, we do all of our searching by hand. Handpicked, artisanal ... and I think that surprises a lot of people because we do ... we send out a ton of ... We find really good deals and send out ... We support the entire world. You know, it's not just for folks in the US, but for folks on every single continent. And I think last month we sent out about 700 cheap flights that we found. So it's surprising to people that we find these by hand rather than using algorithms.
Scott Keyes: But there's a reason why we continue to do it that way rather than, than building up, you know, a sort of system of computers to search for the fares. And the reason why is that there is an extensive kind of list of factors that people think about when they are booking a flight. And, yeah, price is really important. It is probably first and foremost, I think, the most important thing. But it's not the only thing. You know, there's routing, there's the airline, are bags included? What time of year is it available? Maybe are there specific sort of destination holidays, maybe, you know, Oktoberfest in Munich or Saint Patrick's Day in Dublin? How much availability is there, you know, is there just one or two dates or is there a bunch? What's the deviation from the normal price? Like, a $130 fare to Milan is incredible. A $130 fare to Toronto, you know, I mean that's good, but it's not out of this world. How often does the deal pop up? How recently have we sent it out? You can see these tons and tons of different factors that are all kind of weighed against one another and juggled together. And so ...
Brian Kelly: So do you have editors? So the low fare searchers pop it up to an editor who makes that judgment call based on all those...?
Scott Keyes: I think you really hit the nail on the head there. That I think the best analogy for what we do is something of a newsroom, where we have folks who are really sort of going out, hunting, being those... those truffle pigs. And when they find things that look really good, then they'll kind of run it up the flagpole. And there'll be folks who have been flight experts for a number of years and are playing more of an editor role in they're giving a kind of go/no go decision. Either green light, "Yeah, this deal looks amazing. Let's get it out." Or, "Oh, you know, maybe let's see if there's more availability or other cities." Or you know, "No, this deal just for one of these reasons just isn't quite up to our standards."
Scott Keyes: And so we want to make sure that every single deal we send out passes this kind of rigorous set of criteria rather than it just being like, "Oh, you know, it looks like a good price, but actually there's four stops and it takes 60 hours to get there and it's only available on, like, one day in February." You know, nobody's interested in that deal and so we're not going to send it out. So that's why we've kind of made the determination that like, look, humans are the best ones to actually judge these sorts of qualitative factors and weigh all the totality of a deal and decide if this is kind of worth our while. Is this is one of the best deals of the day, or is it something that we can pass over?
Brian Kelly: Got it. Well, it's actually a kind of funny thing about truffles, that your flight alerts are actually cheaper than probably most truffles that people find in the ground.
Scott Keyes: Wow, I never thought about that, that's a great point.
Brian Kelly: And then, so I mean, are you using ... What's the actual platform, right? Do you recommend Google Flights for the novice flight searcher or, you know, sites like Hopper? People always ask me, what's the cheapest OTA to find flights. And I know there's not one answer, but I'd love to hear your thoughts on the different ones out there.
Scott Keyes: I'll give you my thoughts. I ... the short answer is yes, I love Google Flights. You know, it's really powerful, it's really quick. You get the results in seconds if not milliseconds, as you're supposed to. If you're searching on other places, sometimes, you know, it will take 20, 30 seconds, which, granted, if you're doing one or two searches, is totally fine. But if you're doing, you know, hundreds, if not thousands of searches like us in a day, obviously that adds up pretty quickly. So that's why I like Google Flights. But the sort of longer answer is, I don't think it really matters because OTAs all plug into what are called a GDS, a global distribution system, where they're pulling these fares from. And various OTAs will sometimes, you know, massage the fare, a couple of dollars up, a couple of dollars down, depending on if they're running a promotion or they're trying to gain some market share. But the fares tend to be basically about the same, you know, 95% of the time, between various....
Scott Keyes: But I think if you're just starting out, you've never searched before, use Google Flights. If you have one that you really love for whatever reason, go for it. You'll find basically the same results there. The only thing, though, that I would recommend for folks is Google Flights is great and really powerful, but it's only searching a small subset of places where you can buy. So it's searching directly with the airline and it's searching some of the largest OTAs, or online travel agencies. See, so, you know, Orbitz, Priceline, places like that. Other metasearch sites. So ones like Momondo, Skyscanner and Kayak, they also search a lot smaller OTAs. And you know, look, there's a long conversation to be had about smaller OTAs, are they worth it? Are they risky? But oftentimes you can find fares that are a lot lower on smaller OTAs, but it's a lot easier to, you know, do these metasearches on Momondo because they're searching a couple hundred of them at once rather than just searching, you know, five or six of the largest ones.
Brian Kelly: I like Google Flights but it's not always perfect. I know as much ... I was searching in Asia and Singapore Airlines flights were just not coming up on certain routes. So it's never, like, fully perfect. The whole GDS system is ... it's a fascinating and interesting world about how the airlines file fares, especially in business and first class, because a lot of the ... a lot of the focus is on coach fares. What are you guys... Are you guys seeing more and more interest in, you know, mistake business and first class fares, or is your bread and butter mostly, you know, economy flights?
Scott Keyes: When the price is right, absolutely... There's nothing I love more than a really good fare that happens to also be in business class. So, you know, last month for instance, we found fares from New York down to Lima in business class for $587, down to Argentina Buenos Aires for $728. We had some incredible fares last year. One of the best deals of the year, which was there were some mistake fares from LA and San Francisco over to Bali, Bangkok, Vietnam, China in like the $600s round trip. These fares...
Brian Kelly: Was it Hong Airlines?
Scott Keyes: Yeah. Hong Kong Airlines. Not only did we get hundreds if not thousands of our subscribers who booked these flights, I feel like half of my coworkers booked the flights as well. So there's half the team...
Brian Kelly: Yeah, we had a bunch here as well. It's so funny. My phone blows up whenever there an amazing fare. Everyone's like, "Can I go? Can I go?" I'm like, "Well, you know, if you review it for us, sure."
Scott Keyes: You know, I was ... That's one of those that I was on the cusp of booking myself. The problem was at that time my wife was seven months pregnant. And so it just wasn't a good time. But man, that one hurt to pass on. I'm glad so many of our coworkers and our subscribers were able to get it.
Brian Kelly: And how many subscribers are you guys at now?
Scott Keyes: We're at over 1.5 million today. And again, all over the world. Not just in the US but folks in Europe and Australia, Asia, Latin America, the Caribbean. Africa is our most recent expansion. Yeah, all over the world and over a million and a half. It still, to this day, is absolutely mind boggling for me because again, I started this just as a kind of hobby for a couple dozen friends. And here it is now with a million and a half people.
Brian Kelly: Love it. Makes me very happy to hear. I asked some of the people in the office what they would ask you and the first thing was: Will elite qualifying earnings ever be included in alerts?
Scott Keyes: That's a great question, you know, and I appreciate whichever of your coworkers asked this question because we're always kind of looking for new ideas. You know, I don't want to make any promises about kind of specific features, but we're constantly tinkering and testing out new features. There's a ton of stuff that's happening behind the scenes that we're getting ready to roll out. And so hearing, sort of feedback from members, is honestly the best way to guide and direct our efforts. You have a lot of people who are really interested like, "Hey I really want to know, you know, what are the elite qualifying earnings on given fares that you send out? What's the fare class on it?" You know, are they basic economy, regular economy, all of these types of things. It's really helpful to hear what people are interested in and then that helps guide our efforts. So I wouldn't say it's something that's going to happen next week, but it's absolutely something we're going to be considering.
Brian Kelly: So what I would recommend to people listening, if you see a deal, look at that fare class and then there's websites like wheretocredit.com that will actually tell you the earnings in different programs. 'Cause airlines certainly haven't made it easy with the new partner, you know, elite qualifying earnings versus, depending on whether the ticket is booked at as a marketed flight...
Scott Keyes: It's gotten so much more complicated since when you started this thing nine years ago. I mean, the amount of [inaudible 00:19:44] now is...
Brian Kelly: Flying ... Those were the good old ... I would ... The $150 fares to Scandinavia. I was going on weekends, leaving on a Friday night, spending Saturday in Stockholm and then coming back Sunday. And I, as a Delta Diamond at the time, I was earning 50,000 Delta miles for each $150 trip. And actually maybe it was $250? No, it was $143. And I remember the value of those miles alone were like three times the cost of the ticket plus, you know, actually getting to go.
Scott Keyes: I feel like one of the unfortunate kind of casualties of the shift towards elite qualifying earnings shifting towards the dollars spent on the ticket rather than the distance flown is that now all of a sudden the cheap flights, the ones, you know, those $150 flights aren't nearly as valuable from a miles earning perspective as they used to be.
Brian Kelly: But luckily, if you value travel they're still amazing. So, last question about the business, you know, and another feedback from the team is like, considering, you know, and something we're thinking about at The Points Guy is as we grow, is personalization. So how do you view, you know, people who only want certain airlines or alliances, or from certain cities? How can people ... What's the smartest way to sign up to get just the deals that are most meaningful to people?
Scott Keyes: Yeah, that's a great question. So, that's actually one of our biggest goals for 2019 is -- up until now, the way that we have sent out alerts, is, you know, look, you sign up for Scott's Cheap Flights, you say this is where I live, these are the airports that I would like alerts for, and then it's just hey, whenever a really good deal pops up from that airport, we would like for you to be able ... You know, we want to make sure you know about it. So maybe you live in New York, you know, you might get a deal today to London and, you know, or one to Tokyo, but who knows what might actually pop up.
Scott Keyes: What we've realized, though, and one of the things as we've sort of grown and built out the infrastructure is yeah, you know, people definitely love cheap flights, you know, when that $130 flight pops up you might go somewhere you never expected. But at the same time, people do have certain real- world constraints. You know, look, maybe you've got young kids or you're a teacher and you just hear...
Brian Kelly: Or if you're too tall for coach like me.
Scott Keyes: Yeah, if you're too tall for coach, $130 flights -- as much as you would love those -- if that happens in, you know, October and you've got kids in school, or if that happens in coach and you just can't fly that, it doesn't matter. And so we want to try to really sort of build out, all right, maybe let folks be able to say, we only want deals in these months. Or have folks be able to come in and say, "Look, I've already been to ... You know, I just got back from London. I don't want any more deals to London. I'm good on that, but I want to go to South America," or something like that. Or, "I just really want to go to the beach. I don't care if that's in Puerto Rico or Spain or, you know, Okinawa, get me to the beach. It's cold as hell right here."
Scott Keyes: If we could have done this technologically, I would have done it yesterday. I would love to be able to do that. Obviously it's a little bit of a coding and programming lift to be able to build out that infrastructure. But that's something that we're really excited, keen to be working on going forward in 2019 to give people, like you said, that sort of personalization, customization so that they're not only getting the best deals, but especially ones that they are particularly interested in and not the ones that they're not interested in. You know, a lot of focus goes towards the cheap flights, the alerts that we do send out. But in a lot of ways I think it's just as important the ones that you don't get sent. Being respectful of people's inboxes. You know, I hate spam. I hate...
Brian Kelly: There's so much inbox fatigue these days. Yeah. [crosstalk 00:23:33]
Scott Keyes: [crosstalk 00:23:33] Right, so like getting people's preferences so we're making sure that we're only hitting them with the ones that they are interested in and avoiding ones that they couldn't care less about is a real goal for this year.
Brian Kelly: What do you say to people who ask you what's the cheapest day to book flights? Is there one?
Scott Keyes: Man, so, it's fascinating to me, a lot of these early internet flight things that have grown into myths and legends that are still ... people believe to this day but haven't been true for many years. So, you know, look, it used to be the case decades ago that airlines would load their fares online once a week, Tuesday at 1pm or Wednesday at midnight or, I don't know, Saturday at noon. And that hasn't been true since, like, maybe the late 90s, or early 2000s.
Scott Keyes: Nowadays, airfare's changing by the hour if not by the minute. So there really is no best day of the week to book anymore. But, the upshot is that cheap flights can pop up anytime. It's definitely still the case, though, that, like, last minute flights tend to be quite expensive. You don't want to wait until the last week or two because they tend to jump in price. Whereas a lot of people still assume that, again, like the early 2000s or late 90s or even frankly earlier than that, that the last minute flights used to drop in price because the airlines were trying to, you know, fill any unsold seats because then it's lost revenue. But we know nowadays that they jack up those prices because look, they're trying to get as much money as possible from the business travelers.
Brian Kelly: Yeah. And last question, you know, there was a recent lawsuit from Lufthansa suing someone for throwaway ticketing and United went after SkipFlag. What is your take on throwing away that last segment to get the cheapest fare and do you guys ever publicize those in order to save the most money?
Scott Keyes: So, I'll take your second question first. No, we don't tend to send those out because I think they're a little bit complicated from a sort of user perspective. Look, there's a lot of things that go into hidden city ticketing in terms of, like, not checking bags, you know, making sure that you only book a one-way ticket because as soon as you miss a leg, the rest of the itinerary automatically gets canceled out. Personally, though, I think hidden city ticketing is neither illegal nor immoral. Like the New York Times Ethicist says, you know, "Look, when you buy an entire loaf of bread, you don't have to eat every slice." You don't have to fly every single leg ... I know the airlines would like for you to, they set their prices expecting that you will. But you know, I think you're not under any obligation to use every single one whether that ... to consume the entire product when you buy one, that's true, whether it's a plane ticket or an extra large pizza.
Scott Keyes: But, that said, it is really important to read up on the pitfalls and how to make sure that you don't get stranded in some city without your bags because you didn't realize what kind of things to look out for and things to avoid in order to take advantage of a good hidden city ticket. But look, man, sometimes they can be hundreds and hundreds of dollars cheaper than otherwise. So if somebody finds one and books it, man, more power to them.
Brian Kelly: Yeah, hopefully ... Yeah, the airlines are getting better and better about sniffing them out. So I think in general, as long as people don't do it a ton, but otherwise, you know, they could drain your frequent flyer miles, there are risks, but as with everything in life, weigh the pros and cons. All right, Scott, we've got to wrap up here, but do you want to ... I love to end my sessions with a little self promotion. So for people who want to sign up for Scott's Cheap Flights, how do they do it? What's your ... the cost? And where can people follow you on social?
Scott Keyes: Yeah, so you can sign up at scottscheapflights.com. No dashes, no apostrophes, anything like that. scottscheapflights.com. We've got all our socials on there, Facebook, Twitter, Instagram, all that. It's free to sign up. We've also got a premium tier for folks who want extra perks. All the deals get sent to folks who are on the premium list, whereas just a small subset get sent to the folks who are on the free list. They get to choose certain perks. They can choose their specific airports, they get the deals first. They get, for instance, Hawaii, Alaska deals, all the mistake fares only go to premium members. There's no ads, a 30-day money-back guarantee, but honestly, whichever one you're comfortable with, try it out.
Brian Kelly: How much is the premium?
Scott Keyes: The Premium costs $39 a year, and that helps support the team to be able to build out these new features and continue to send -- to search and send -- for the best deals possible.
Brian Kelly: And last question, the most important, are you an aisle or window person?
Scott Keyes: Oh man, I'm a window. I've got to sleep on those planes.
Brian Kelly: Yeah, I like it. All right Scott, thanks for joining us, and the safest of travels.
Scott Keyes: Thanks so much for having me, Brian, really appreciate it.
Brian Kelly: That's all for this episode of Talking Points. Thanks again to our guest, Scott Keyes of Scott's Cheap Flights.