S4, E3: I’ve Been Booking Trips With Points Since I Was 12—Here’s How To Win at Travel

On this episode of Unpacked by Afar, host Aislyn Greene chats with Brian Kelly, aka The Points Guy. In his new book, How To Win at Travel, he breaks down his best tips and strategies to help travel beginners and frequent fliers maximize their travel potential. In this episode, you’ll learn how to avoid common mistakes when booking with points and miles, the mindsets and strategies that have brought Brian decades of success and what tools will help you win at the game of travel with points and miles.

Transcript

Aislyn: I’m Aislyn Greene, and this is Unpacked, the podcast that unpacks one tricky topic in travel each week. And this week, our guest is Brian Kelly, or as most people know him, The Points Guy—that’s his nickname and the name of the popular travel blog, thepointsguy.com, that educates travelers about travel credit cards, points and strategies, and so much more.

Brian has been in the points and miles game since he was literally a child. He booked his very first trip using miles, at the tender age of 12. A few decades and many blog posts later, he has consolidated all of that knowledge into a new book called, appropriately, How to Win at Travel. It’s a primer for anyone who feels overwhelmed by points and miles and knows they are missing out, but intermediate and even expert points-and-miles-aficionados will find useful nuggets too. Here’s Brian Kelly on how to win at travel in 2025.

Brian, so nice to meet you. Welcome to Unpacked and congrats on the book.

Brian: Thank you so much. Yeah. I just had a baby boy and this is like giving birth again, six weeks later. So one-two punch, but, uh, I’m so excited.

Aislyn: Wow. OK. So six weeks between baby and book launch.

Brian: Give or take. Yes.

Aislyn: Wow. That’s a lot.

Brian: When it, when it rains, it pours. I’m a believer.

Aislyn: There you go. And do you have a book tour planned?

Brian: I just announced it. So I’m actually, my first ever—I’m from Bucks County, Pennsylvania. So my local bookshop that I went to growing up, Doylestown Bookshop, will be my first stop. And then I’m going to Philly, New York, Miami, L.A., um, and then probably Austin, Chicago, Boston, and a couple others.

So, I’m excited. I love meeting readers of the website, hearing their travel stories, so. . . and you know what? I can earn a bunch of frequent flier miles while I’m at it.

Aislyn: If you didn’t, I would be shocked and horrified.

Brian: Gotta practice what you preach.

Aislyn: Gotta practice what you preach. Well, could we start at the beginning? I love that in your book you share your origin story when it comes to points and miles. And it goes back to your childhood, speaking of childhood. So could you share, kind of, the abbreviated version of how you got to where you are today?

Brian: So, I was always the techie. I was born in 1983. And I remember I got my first computer in 1990, ’91. So I was like the eight-year-old hacker of the family. And I was on AOL and Prodigy back in the day. And my dad got a job for a startup and he was working from home. So I was his computer wiz booking his travel.

And the long and short of it is he came to me one day and said, “I have all these frequent flier miles.” I’m one of four kids, you know, we didn’t do Europe, you know, we were comfortably middle class, but my parents were pretty frugal, like we would road-trip, maybe go to Florida. But I’ve always, I don’t know, I think it’s genetic, and I talk about it in the book, like this wanderlust gene, but I was like, I don’t want to do Daytona, you know, so I figured out how to book all six of us to go to the Cayman Islands for free.

I mean, and this is 1996.

Aislyn: Oh my God.

Brian: Uh, I was 12 years old, planned our first family trip. We had to get passports. I remember my dad was like: “Are there hospitals in the Cayman Islands?” I actually used Vrbo. The first year Vrbo was around. So we were, we were able to rent this beautiful beachfront cottage, you know, that was a doctor’s in New Jersey.

It was his winter house that was empty most of the year, so he was happy to rent it. So we, we had this amazing family trip. So throughout the ’90s, every year, my job was to use my dad’s points. ’Cause he traveled so much. So it was kind of like our consolation prize, ’cause he was a business traveler and that’s—never in a million years did I think it would become what it has.

But I’ve been doing this game now for a long time. Almost 30 years.

Aislyn: A long time, and I like how you talked about the anxiety of that first trip. What happened?

Brian: The night before we’re all supposed to leave, and mind you, my dad and three siblings flew nonstop Philly to Grand Cayman. We didn’t have enough miles to fly together. So my mom and I flew through Miami, we had American miles. And I remember, I remember so vividly flying over Cuba with my mom after that layover in Miami, just thinking what the heck’s gonna happen?

Like, when I see my dad at immigration, is he gonna like punish me? Is it horrible? And the look on his face when I saw him, he was just beaming with joy. And I think that probably was the definitive moment for me where travel, it can have its high stakes, but the payoff when that trip is amazing and life changing. Like, I think as a 41-year-old, I think about that trip all the time.

And I just am so excited for others. Even if you haven’t gotten into the points game by now, the game is everything. You know, you. It’s not even like a nice to have this, this, uh, sub-community of frequent flier people, like frequent flier miles and loyalty are the future. So, I’m excited for more people to get to experience that.

Aislyn: And your book is kind of the perfect tool to set everyone up. So in, in the kind of beginning of the book, you talk about how people romanticize, like, the golden era of travel, and you say that actually we live in a much safer and more beneficial time. So can you tell us, what is the platinum age of travel?

Brian: So, so, you know, it’s so easy. You know, I think a lot of people are just pessimists. I’m an optimist. I look at the bright side of things. And when you look at just the numbers and how safe travel is today, how connected the world is and how affordable—you may think travel is really expensive today, but when you look back over time, it actually used to be, the golden age of travel was only for rich people, period, full stop.

So yes, you know, you might see pictures of people. Oh, that’s when they got dressed up. That’s just because there was only rich people back then.

Aislyn: Yes.

Brian: And that’s not a good thing, you know, that, you know, it was so exclusive. It was basically 1 percent of your salary was a domestic flight. So, I talk about now. So platinum is a play on loyalty status and that you don’t have to be rich today to fly first class, to fly international.

And that is the underpinning of this book is to teach people that to be an expert traveler, it does not take buying 10,000 tickets. You can have that experience for far, far less. You just need to know how to play the game. So even the most beginner, you may have friends who have points you have, may have said this thing’s too complicated.

Well, now there’s a book, so there’s no more excuses. You can sit and read this book. I’m 100 percent sure you may not get every single of the more nuanced credit cards. It might get a little confusing, but it will give you the foundations to understand, “Oh, this whole ecosystem, it’s, it’s lucrative.”

And I want everyone to finish the book and say, “There’s like three big things I need to be doing today. Whether it’s paying my rent with a credit card that has no fees. So I not only earn points, but increase my credit score.” And that’s another kind of overarching theme of the book, is like, by playing the points game smartly, you don’t just get points in free travel, that’s like a really nice perk of it, but also you’re just smarter. Your credit can go up and you learn how to maximize. That’s my favorite word. It’s like you approach things differently when you become a points person, because you realize there’s so much value on the table.

Aislyn: Yeah, it is a mindset shift. When I finished your book, I felt like, oh, this is a book that I would have to read two more times. And each time maybe you go a layer deeper or you become a bit more sophisticated, but there were things that I’m like, oh, I got to do this right now.

It’s like 10 p.m.

Brian: And I, I had to stop myself. So the book’s 300 pages, 15 chapters, and this is like trimmed down. There were so many things and it was challenging for me because I’m a blogger to the core. So, you know, starting the Points Guy 15 years ago, I love to go into one topic and go down a rabbit hole, and I found myself doing that while writing the book.

And I had to say to myself, this isn’t a blog post. I need to give the high level . . .

Aislyn: Yes.

Brian: I know for sure, like the book will give you the foundation of being like, Oh, you’re going to take notes and be like, “I got to follow up here, here, and here,” ’cause people did say, they’re like, “Well, why would anyone read your book?”

’Cause there’s a million blog posts all over the internet. I’m like, because there’s a million posts, what human can start sequentially and put it all together?

Aislyn: Yes.

Brian: And I know that most people can’t ’cause I started this blog 15 years ago. And while I’m so proud of how popular it’s become, people are still confused because the game keeps, like, keeps changing.

So like what I’m teaching in the book is like fundamentals to think differently so you can tweak your personal strategy.

Aislyn: Well, you mentioned that you are an optimist, and that did jump out throughout your book, because there’s been a lot of talk, especially over the past few years about inflation around points and devaluation. So how are you still an optimist?

Why are you still an optimist?

Brian: So look with points, there’s three sides of the coin, really: earning points, redeeming points, and then perks, getting these non-point-related values from your card, such as protections when things go wrong. People don’t realize your credit card, if your flight’s delayed and you have to go and get an airport hotel, you may have to wait in line for two hours with an airline to get a voucher for Motel Six when your credit card will put you up at the west end in the airport for free. Or you lose something and there’s purchase protection: I bought a coat and lost it recently and I got it instantly taken off my credit card bill.

So the perks are super valuable. But back to your question of inflation. So, when you look purely at, like, the cost of flights in terms of miles. Yes, the airlines keep charging more and more. So, like, that round-trip flight 10 years ago to Europe in business class used to be 100,000 points. It’s now 250,000 on some airlines, but there are many where it’s less. So you beat inflation two ways: number one, by diversifying your currencies.

And that’s a big lesson I hope people get. Even if you like United and you fly United and you have a United Co. brand, that’s not the winning strategy. You can still fly United and have a United credit card for perks, free bags, but you’re going to put all your real spend on a different credit card so that you can transfer to the best frequent flier programs.

So leveraging transfer partners is a big lesson that I think most people, even frequent fliers, get wrong. And secondly, you earn more points. So there’s never been a time where you can earn as many points from credit cards. When I started the Points Guy, it was really AmEx, Chase, and Citi, kind of.

Now there’s twice as many credit card issuers with rock-star credit cards, 100,000-point bonuses, small-business credit cards. You can now earn points on rent, shopping. So as long as you’re earning more than what inflation is happening, you can still win. Plus then you factor in the cherry on top, all those perks. And you’re taking that money off the table. That’s how you stay ahead of the curve. And I think that’s where most people still have a credit card and point strategy rooted in strategy from 10 years ago. And that’s what I want people to open their eyes that like, you need to keep evolving with this industry.

And I’m going to show you the core areas you need to focus on.

Aislyn: Well, you also said that knowledge is our currency when it comes to travel. It’s less about actually having the money and more about having the info. Can you just share a little bit more about what you mean by that?

Brian: Yeah. So, so you don’t need to buy points. So, so many of the points that we earn today are built into the cost of our economy. So, when you go buy a shirt at a store that’s $20, if you pay with cash, you’re losing out on valuable points. It’s the same price of merchandise, but you could have had 40 points by using the right credit card.

And that’s just a tiny little example. So, you just need to know where to get points. Online shopping. The easiest thing you can do is click through online shopping portals. It puts a cookie on your computer and you earn free extra points in addition to those credit card points. So there’s all of these ways to be raking in value without spending a single extra cent and that’s what I tell people, the more you mine your knowledge into the loyalty programs you have, the more valuable they become. So, yes, you can take the defeatist attitude of American Airlines keeps changing the rules. Therefore, their miles are less valuable.

No, there’s still tons of sweet spots for those who know. There’s tons of technology. Now, I go into all these new apps and tools that scan for you.

So, when you combine earning more points than ever, new technologies to scan airlines, to snatch those really good flights that are still out there. That’s where experts and even intermediates in this space can get outsized value. So basically for those who want to put in a little bit of extra work, there’s huge returns.

Aislyn: Well, getting into some of those concrete tips, because you likened traveling better or winning at travel to a sport. So how would you suggest that someone begin their training regimen, so to speak?

Brian: Travel is my favorite sport and I’m not going to lie, it can be challenging some days, but . . .

Aislyn: Yeah.

Brian: The first step to winning at travel, I would say, is before you leave your house, it’s while booking travel. I think a lot of people make mistakes by, you know, just going to one airline’s website and assuming they’re getting the best price.

Or, you know, just going on to book hotels and going through an online travel agency. When, if you went directly to the hotel for the same price, you could also get really valuable hotel rewards, perks, or by booking through, if you’re, if you like luxury hotels, like I do, it kills me because so many people will go directly to fourseasons.com but you can even get cheaper rates by booking through partnered, high-end luxury travel advisors. Same rate, but hundreds in extra perks: late checkout, free champagne. But that’s why people just don’t know that, because if you’re not a luxury traveler, you’re going to spend one, you know, I’m going to go on my honeymoon to the Four Seasons Maui.

Oh, let me just go to fourseasons.com/maui. No, please.

Aislyn: Yeah. Yeah. Yeah.

Brian: And that’s where people always come to me after the fact. And they’re like, “Oh, I booked this really cheap economy ticket in this real, like basic economy. It’s my honeymoon, but now I want to upgrade it.” I’m like, “You can’t because you booked the wrong fare class.”

So winning at travel starts at, and I go through this in the beginning chapters, thinking strategically about how you book travel, the platform, the website, because, you know, even with airlines these days, the airlines want you to book direct. And if your flight gets canceled, if you booked through an on some online travel agencies, if there’s a flight 30 minutes later, if you booked through the airline, they’ll put you on the next flight.

But if you booked through certain OTAs, you have to call the OTA. Can you imagine? I know this, sitting at the airport waiting to get through and you missed the connecting flight. And that happens to lots and lots of people, and I see it keep happening. I’m so keenly attuned to social media, especially during these meltdowns. The airports.

I see people waiting in the two-hour-long line and I’m like, “No, people.”

Aislyn: Don’t do it.

Brian: Like, you can go online, chatbot, you know, when you’re, when you’re stuck at the airport, call the international line, the Mexico helpline for example, for your airline, you’re probably going to get through in five minutes versus two hours And that is winning because you can get through before everyone else and snag the last seat home.

So, winning is a mentality that you need to do a little bit of research, hence my book which takes you from the beginning to when things there’s a whole chapter on when things go wrong, how to upgrade, etcetera. So yeah, it’s a, it’s a mentality and it’s a sport and it gets better with time as you practice.

Aislyn: Speaking of flights, you shared a few misconceptions around booking flights that I thought were quite interesting. Would you mind sharing just one or two?

Brian: I think people need to be more strategic about booking flights, you know, not all airplanes are the same. Like I talk about New York to L.A., there are certain aircraft that have beautiful lie-flat beds with your own privacy doors. And then there are some with 20-year-old business class that are angled lie-flat, where you have to step over your seatmate and they’re the same price.

So when you look on Google flights, it all looks the same, but it’s not. So I teach travelers—here are the things that you need to look out for. Also, you know, the flight time, the time in which you fly, especially internationally and especially for jet lag. I learned so much while writing the travel health chapter.

I sat down with scientists and learned all about the circadian, uh, your circadian clock is so critical to jet lag. And it’s funny, I was writing this book, a portion of that chapter, I was in Tokyo. And interestingly, the, the, the hardest hit route for jet lag is New York to Tokyo.

And when I came home from that Tokyo trip, it was six days of waking up at 3, 3:30, 4 a.m. wide awake—and I’m a dad and I’m writing a book and also working full time and I’m like, you know, you realize later in life, like your time is more and more precious.

And back in the day, OK, jet lag, I’ll wake up and watch some like crappy TV show. But then you’re like, “Oh no, but I need to be on and a parent all day and, and then work and then go on live TV to do my job. I, you know, I just can’t run on that three hours of sleep like I used to. So, the whole jet lag chapter is really fascinating, learning about light exposure. I was doing, you know, I always just assumed, OK, just try to get as much sleep on the plane and then you’ll be good to go. But in fact, that can be really detrimental and set you back. You can actually hurt yourself by sleeping at the wrong times and by getting exposed to light at the wrong times.

So I hope people just take nuggets out of that to think a little bit differently about how they approach travel because I know it’s tough when you’re in first class on a plane and you want to drink the free alcohol.

Aislyn: Yeah. Yeah.

Brian: But think about it like: I’m going to Paris, let me just have a much better martini at a gorgeous restaurant, fully rested than being bleary-eyed, falling asleep at this fine dining restaurant. I just like to have different mindsets for people to think about, just think a little bit differently about how they approach travel to flights. The flights they book, just being a little bit smarter.

Aislyn: Well, moving on to credit cards, if someone is a beginner who has flirted with this, like what are the core tips to begin in this space?

Brian: Number one to win at the credit card game: You must pay your bills off in full every month. So travel credit cards that offer points have really high interest rates compared to like the 0 percent APR. So there’s a credit card for every situation. And I go through this in the book.

Like if you’re in debt right now, and you’re paying 20, 30 percent APR, you will be paying many times more the value of the points you’re earning. So the core focus should be just getting debt free. That’s the easiest way to get your credit score up. I was in credit card debt and did dumb, dumb things. When I graduated college, I thought bills would just disappear. They don’t.

And I want people to treat their credit score like an asset. So step number one is understanding the upside with credit cards and understanding how credit works. I think it’s amazing how we never learn how credit scores work. So . . .

Aislyn: It’s not part of our education, yeah.

Brian: There are a lot of myths out there that like, “Oh, if I apply for a credit card, it’s going to destroy my credit score.” And it’s like a nugget of that is true and that like your score will go down to maybe 5 points now out of 850, that’s negligible.That’s not tanking your score.

But what people don’t realize is as long as you pay that bill off in full every month, the more available credit you have to you. The way credit works is they judge how responsible you are by how much available credit you have and how much you’re using. It’s what’s called utilization.

So if you were to have one credit card, $5,000 credit line, and even if you paid off on the due date, but it’s $3,000 a month that you’re paying off, it, it can report, um, as, like, 75 percent utilization and your score can drop really far. But if you had $50,000 through five different credit cards and you were using $3,000, your utilization, which is your second highest aspect, is super low.Your score will shoot up.

So the more credit you have available, the more credit cards you pay on time every month, which is the number one factor that goes into your score. So that’s how you can get these juicy signup bonuses, which are thousands of dollars these days if you know how to use them. And then number two, you have a lot of different credit cards that you can get bonuses on the category spend, making sure you’re earning for your groceries, dining, you know drugstores, streaming.

There’s so many different—rent. You want to look at every single category that you spend money on and make sure you’re getting ideally more than one cent or one point per dollar spent. So the credit game is fascinating. You earn all these points, but your score goes up over time so that when it’s time to get a mortgage, you’ll get a better mortgage rate and that can save you many thousands of dollars.

So this points game, all the travel perks are great, but like your credit score being primo and getting a lifetime of really low interest rates for cars, for mortgages, that’s, that’s the big picture that I want people to see.

Aislyn: And I do appreciate that throughout the book, that you really emphasize, responsible credit card management. And I wanted to touch on that a little bit and get your suggestions because there is that research that points to people spending on average like 10 to 20 percent more, when they use credit versus like cash or debit.

So how have you stayed within your spending goals? I don’t want to say a budget. And what do you, what would you suggest for travelers?

Brian: Well, I don’t necessarily agree. I think a lot of those studies were many years ago. And, and frankly there is a large population of people who if given any credit will spend crazily. There is a culture in America . . .

Aislyn: Yeah.

Brian: . . . and truly, like, this book and credit cards isn’t for you if it’s—if you don’t want to play by the rules. There are rules to this game, you know?

Aislyn: Yeah. Yeah. Yeah.

Brian: And you have to play by them. So if you, and I say this very clearly, if you’re gonna get a new credit card and you’re gonna be spending more than you would have—you’re losing, don’t do it. Like, but I think most people, I think financial literacy is a muscle, especially younger generations now with Fintalk and people are getting the game, like how to win against these big companies.

So I do think consumers are smart at the core level, and I actually think people spend smarter when they can see how much they’re spending in digital apps that can show how much you’re spending. There’s a lot of downsides to cash.

So not only are you for, forgoing the points, but you’re also forgoing the protection.

So that package from a random Instagram ad that never shows up. This happened to me the other day. You literally just text, you know, through the app, dispute the charge. I never got this. They can’t prove you did. Boom. It’s off. So, like, credit cards offer so much protection and those are the intangible perks that I really just wish more people knew about.

And then thirdly, instead of just using your cash, you can let that sit in a high-yield savings account for a month to 45 days before you pay it off. So you’re earning interest, earning points and earning protections if anything goes wrong. Like that is the mentality. You should let these banks loan you free money.

Aislyn: Yeah.

Brian: If you’re smart about just keeping your cash in high-yield savings and earning and paying your bills off when you need to.

Aislyn: It’s like you need to know yourself, right? And know what temptations lead you astray. So, you mentioned in the book too that you have 28 credit cards, which you say is on the low side for those in this industry, which I’ve heard is upwards of 50, 60. So how do you manage all of that?

How do you recommend that travelers, like to make sure you’re getting the benefit out of each one—it seems complex.

Brian: It is complex and, and you know, I have a spreadsheet. I think there’s apps that you can use. I do warn that a lot of these apps you’re going to give a lot of personal data.

Aislyn: Yeah, yeah.

Brian: I’m pretty crazy. Most of my credit cards are Amex, Chase, Capital One, and Bilt. You know, those are the ones I use every day. I, I have auto pay for all of them.

And I always have enough cash to at least do—no matter what, always have every single credit card, the minimum payment.

Aislyn: Smart.

Brian: I mean, even if you get hit with an interest payment one month, it’s not the end of the world. Half the time, if you don’t pay it, you can actually pay it right away and call and ask them to waive the interest.

Aislyn: Interesting.

Brian: That’s another core tip of the book is it never hurts to ask. With airlines, with credit cards, people feel defeated, but I can’t tell you how many free things I’ve gotten over the years: upgrades, you know, getting on the earlier flight, even though it’s international and technically you’re not supposed to, but if you’re nice to people, it never hurts to ask.

So back to your answer, you know, I’m maniacal about it. I think anyone in the points game should be. Always, you know, do routine audits to make sure that you’re actually getting the right amount of points for certain purchases. Did it code as a restaurant? Sometimes restaurants switch their processors, so you can kind of double-check on your own to make sure you’re getting what you deserve. And nowadays with chatbots, it’s so easy to say, “Hey, for this big banquet purchase for my birthday party, it didn’t code as 4X for dining. Can you fix that?”

So, I’m pretty manual about it still, you know, there are apps out there that I go into [in] the book: AwardWallet, one that’ll track most of your miles and points. It’ll let you know if there’s expiration, uh, there are apps that’ll let you know, if you’ve got credits that you haven’t used on your credit card. But I’m a little old-fashioned and I recommend people in the beginning, just put up a spreadsheet with the core information: Here are the perks on this card that I need to use, you know, what is this, what categories, does it give me bonuses, etcetera.

Aislyn: You mentioned AwardWallet and there were a few other tech tools or apps that you recommend throughout the book. Are there say three that you feel like are essential?

Brian: Yeah, I’ll say AwardWallet is wonderful. It’s been around for many years. I know the founder, he’s a points nerd. It’s not perfect. So, without getting into the weeds, the loyalty world is so lucrative for airlines and hotels. The airlines and hotels don’t like these third-party apps coming in and trying to take you out of their ecosystem. So sometimes it’s a cat and mouse game. Some airlines don’t allow you to track automatically. There’s work-arounds. So, the reason why it’s not because for lack of trying, but the loyalty industry, it’s a big, big moneymaker. This is how the airlines make more money selling points.

So they want you going directly to their website. I have to say that the, the app or the tool Point.me, I would say it’s the closest thing to be like Google Flights. So airlines all share their fare data so that you can shop on online travel agencies when buying a flight, but the same does not exist or hadn’t, when using your miles. So if you have miles all over the place and you just want to go Chicago to Paris . . .

Aislyn: Yeah.

Brian: . . . in the old day’s you’d have to go airline by airline, check their award prices, sort of have 20 tabs open. Now there’s a bunch of new tools.

They’re not, not one of them is perfect, but Point.me is the closest I would say, and it’s free if you have Amex and Bilt. So this will actually tell you, “Oh, you can transfer your points to all these different—this is the price to go Chicago to Paris.”

Instead of spending on $1,000 economy flight, you might be able to book it, which is a 100,000 points, through the credit card or paying, you can get it for 30,000 by transferring to Air France or 50,000 by transferring to, to AeroPlan, which is a partner with United, because it gets very complicated on the redemption side.

So Point.me is one of the more user friendly. So you can just put in a certain day, you can put in your airport where you want to go. Seats.aero is the more expert tool and this one I adore. It takes a little bit to get used to. But if . . .

Aislyn: Sounds like it.

Brian: . . . to win at, to win at points you need to be flexible and a key thing I mentioned in the book is like, let the deal shape where you go because if you can find great award deals, book the trip around those dates when you can find them, and then save so much money so that you can spend on the things you love, like those fancy meals. So Seats.aero allows you to take airline by airline, and let’s just take Emirates, for example.

Emirates is one of my favorite airlines. Their first class is out of this world, unlimited caviar, Dom Perignon, showers onboard certain aircraft. They fly JFK to Milan, which is the most fabulous way to go on your summer trip to Italy. Well, Seats.aero will actually, if you’re a pro version, it’ll actually take a full year and it’ll show you all the days that are first class, and by route. So you can take that data and then you work your trips around the availability, if that’s a possibility. I love just getting inspiration to be like, “Oh, there’s business class to Tokyo next week. Let’s do that.” You know? Be spontaneous.

Aislyn: Yeah, yeah, yeah.

Brian: So having those tools takes a lot of the manual search out of it. So those tools, they’re a little wonky, each one has its own . . . but trust me, if you’re in the points game, you can get three times the value of your points than what you’re normally getting by leveraging these technologies.

Aislyn: Because I think that’s actually from my anecdotal understanding where people get the most confused is on the redemption side, like the earning feels a little more straightforward. But when it comes to redeeming, it’s just feels like Wild West a little bit. So that chapter was really helpful.

Brian: Yeah, there’s a, there’s an epidemic of points hoarding. There’s a lot of mental . . .

Aislyn: Yeah.

Brian: . . . a lot of people just want to keep their points. But once again, the inflation is going up. So your points lose value over time. So use them now. Stop hoarding points, because if you just keep holding them, you’re losing value. On the same token, you don’t want to squander your points for like magazine subscriptions, but . . .

Aislyn: Totally.

Brian: . . . you want to have a strategy in place. And once you start redeeming for really good value, when you’re redeeming for business class for less than what you would have paid for coach, that’s when this will click and that’s when you will become a hardcore points user.

Aislyn: One of my main takeaways was that you don’t really chase elite status on an airline anymore. I thought that was so interesting. Could you just share a little bit about where we’re at with that?

Brian: So elite status, when I started the Points Guy in 2010, basically 80 percent of domestic first-class seats were given away for free to elite members. So elite status, and back then you could fly a certain amount of cheap flights and get top tier status. So there was a lot of gamification of that, like where people go on mileage runs.

So you could fly $500 to Tokyo and get elite status and free upgrades for two years. That game has flipped. So now only about 20 percent of those same seats are available for upgrades. So a lot of the perks have been getting watered down. I’m now more loyal to my credit cards, because the airlines now have increased the bar for elite status, decreased the benefits.

So the calculation is not a slam dunk like it used to be. The old notion, the habit of just getting elite status, cause you’re hooked on it, take a deep, hard look and say, the airlines now require much more than just flying on them. Now you need to spend huge amounts of money and the opportunity costs, which you learn about in the points earning chapter, is that by spending on a frankly meh airline cobrand card and earning these somewhat less valuable airline miles when you could be earning huge amounts of super valuable credit card points that you can transfer to all different airlines. There’s a huge opportunity cost by, by saying to an airline, I’m only going to get airline miles.

What happens when you want to fly Emirates and all you have are Delta miles and you, you can’t, you can’t transfer points from one airline to another. So I want people to at least start doing the calculation. Well, if I’m spending 100,000 thousand on it: Am I getting the value through the elite perks? Am I getting those upgrades and better service? For some people they are, but I would say for the lower elite tiers, you know, take a cold, hard look at that. And so basically be more loyal to credit cards than to airlines.

Aislyn: You mentioned this earlier: A, the importance of kindness, especially when things go wrong, and you have a whole chapter on how to win when things go wrong. You know, in some situations you’re saying like, I know that a flight was canceled before the gate agents do. Um, so any main takeaways from what to do when things go wrong and why it’s so important just to be nice to people?

Brian: So my tip for when things go wrong, which they will, number one is have the right information. People who operate out of a lack of information make mistakes. So understand why the flight’s delayed. That will open up, well, how flexible is the airline going to be with reaccommodating me?

Now, if this was like a nationwide FAA outage, you’re going to have a little bit less flexibility because the agent’s going to be like, look, I’m dealing with everyone, you know, you’re, everyone needs to get to where they’re going.

If the airline oversold the flight, you’ve got a lot more flexibility, and the airline does too. The agents have a different toolkit for how to deal with you. So understanding where you’re at and really understanding, are you asking for a favor, which most people are, and they don’t realize.

Aislyn: Yeah, yes.

Brian: So understand the difference of what am I owed, and the rule of law with, with airlines is the contract of carriage, which most people probably never heard of.

And I explain that whenever you buy an airline ticket, you’re agreeing to a set of rules with the airline. There are some rules with the government, and those have actually gotten better for consumers. But in general, you need to be strategic in your ask. So back to information, is like knowing what other options are available.

If you can go to an airline agent and say, “Hey, look, there’s one seat open on this other flight. I gotta get to, you know, the West Coast. I’m fine flying to San Francisco, flight number Delta 419. There’s one coach seat. Can you please do it? Thank you. Thank you. Thank you.” I can’t tell you how different that is than you screaming at the agent saying, you guys always cancel my flight.

Aislyn: Yeah.

Brian: Think about it. If you were behind that counter and someone’s being a jerk to you, are you going to go above and beyond and even stick your neck out on the line to get, because agents now can get in trouble for bending the rules.

So think to yourself: Am I giving this agent a really good reason to help me? Because they have all the power.

Aislyn: Yeah.

Brian: Bottom line, the airline is not going to care if you complain and you’re, you know, even if you have a big social media following, they don’t care, you know, like.

Aislyn: Yeah, yeah.

Brian: So be strategic. Say: Am I doing everything right now that’s going to get me what I want?

And I get, I’m impatient, so I can get testy, and I still have to learn this many years in, so I get the natural reaction, but think, think bigger picture, and if you’re asking for a favor, you got to approach it a little bit different.

Aislyn: Well, I think you also mentioned how, you know, things go wrong and you’re the first person on the app or on the phone rather than standing in line. Like last year, there was a big epic meltdown on my layover in Dallas. There were two-hour lines waiting just to get hotel vouchers. All the airport hotels were booked up.

I just left. I booked a hotel on my phone, took an Uber, and got one of like the last hotel rooms on the outskirts of the city. And I was like, “Oh, you sometimes you just figure it out on your own and then you try to get compensation later, right?

Brian: Well, that’s what you have to do. So the DOT now has rules that state you will get a refund. If your flight is canceled for any reason, you’re getting a refund if you want it. So knowing that, if the airline you’re flying on has no other flights home, book yourself on another airline.

A, use points. A lot of people don’t realize, when your flight’s canceled on one airline, you can book on points on another as a backup option. And one of the most beautiful things to happen out of the pandemic is almost every airline loyalty program, this is a huge lesson that people don’t realize, is you can redeem your points and cancel up until departure and get all your miles and points back free of charge.

So what I do is, the minute I smell a delay—and another tip I give in the book is how to start smelling delays before it shows up on the board. It’s understanding where your flight’s coming in from, understanding the weather patterns in the country that day, using sites like Flight Aware, you know, to understand, are there delays in Chicago?

So I, I, I get way ahead of the game. And if I see that my incoming flight’s delayed, well, generally that means your flight’s probably going to be. So I then start thinking, OK, if I really need to get to where I’m going, I just book another flight on a different airline, so that if my flight does indeed get delayed and canceled, I’ve already got the backup.

If I don’t need that backup option, if my flight doesn’t end up being delayed, I cancel it, get all my points back, no cash out of pocket. So points become an insurance policy, and that flexibility, I would say 95 percent of people out there who have points don’t even realize that you could just be booking backup options when things go wrong and if the airline does take care of you, then just cancel the points reservation—nothing is lost. Just remember to cancel it before departure; if you don’t cancel it before the flight takes off, you lose it. But once again, it’s about knowing the rules and, you know, using them for your advantage

Aislyn: And smelling delays. I like that phrasing. Well, I’d love to wrap up with where you think things are going. So if you had to predict five years from now, where we’ll be, especially with the rise of tools like AI, what would you say?

Brian: Well, I do think there’s a lot of friction in travel today. Whether that’s waiting in lines, immigration, biometrics, AI to help solve problems, you still need to wait in those lines in airports and wait on phone lines, and I think there’ll be more self-service.

So I’m hopeful travel will continue to get easier, and I also hope, you know, right now, there’s a lot of uncertainty with planes and aviation. Boeing is not meeting its production, uh, Airbus. There’s going to be a lack of pilots and planes.

Aislyn: Yeah. Yeah.

Brian: And all while increasing demand. So, there’s a lot of pressure on the system now. But like I said earlier, I’m an optimist, and I do think technology can alleviate a lot of that. But it’s why people today need to understand the system to get ahead of it. You need to be your own best advocate. That’s not changing anytime soon. And unfortunately, we’re going to see some airlines, you know, continue to die out as the big ones get bigger.

We’ve seen huge consolidation. Spirit Airlines is on the brink. They’re in bankruptcy. They just had mass layoffs, JetBlue is struggling. So the smaller ones are struggling, Southwest. The big dogs will get bigger. The small ones get smaller. Is that good for consumers? I don’t know.

Aislyn: Yeah. I see.

Brian: So I’m kind of painting a bleak image. But I . . .

Aislyn: [laughs] Yeah, where’s the optimist?

Brian: Now more than ever you have to know the ins and outs. You can’t just wait, wait to be taken care of because you’re going to be waiting a long time.

Aislyn: Totally, and your book helps people get ahead of the game. Well, thank you so much, Brian, for joining us today and sharing your wisdom.

Brian: Thank you for having me and for, for reading the book. I’m so excited for it to, to get out there.

Aislyn: And that was Brian Kelly. In the show notes, we have linked to his new book, How to Win at Travel, as well as to his website. You’ll also find a link to a complementary story I wrote where I pulled out some of my favorite tips from the book, strategies that I will be putting into place this year.

Next week, we’ll be back with a look at the rise of the around-the-world cruise, including some advice from Cruise Mum and Dad, the TikTok celebrities who spent nine months last year sailing around the world.

Did you feel like you could give yourself permission to just stay on the ship? Or was that part of the pressure? Like we’re only here . . .

Audrey: [I] know what you’re going to tell. I know what he’s going to tell on that. [laughter]

Joe: So,

Audrey: Because I was a novice cruiser, so this is my excuse behind this.

Aislyn: OK.

Joe: OK. So I felt we needed to see the world. We need to get off the ship every day and we put pressure on ourselves, right?

Aislyn: Yeah.

Joe: One of our friends, we ran into one of our friends at breakfast and we said, “Hey, where’s so and so,?” And they go, “Oh, he’s, uh, he decided to stay on the ship today and take a break. And Audrey goes, “You can do that?” And I go, like . . . [laughter]

Aislyn: You thought you had to get off the ship? Oh my God.

Audrey: I had no clue. [laughter]

Aislyn: Ready for more Unpacking? Visit afar.com and be sure to follow us on Instagram and Tiktok. We’re @afarmedia. If you enjoy today’s exploration, I hope you’ll come back for more great stories. Subscribing always makes that easy, and be sure to rate and review the show on your favorite podcast platforms. It helps other travelers find it.

And if you want to ask a question or suggest a topic for coverage, you can leave us a voicemail at the link in the show notes, or email us at unpacked@afar.com. This has been Unpacked, a production of Afar Media.

The podcast is produced by Aislyn Greene and Nikki Galteland, music composition by Chris Colin. And remember the travel world is complicated. We’re here to help you unpack it.

Aislyn: Ready for more unpacking? Visit afar.com and be sure to follow us on Instagram and TikTok. We’re at @afarmedia. If you enjoyed today’s exploration, I hope you’ll come back for more great stories. Subscribing always makes that easy. And be sure to rate and review the show on your favorite podcast platforms, it helps other travelers find it. And if you want to ask a question or suggest a topic for coverage, you can leave us a voicemail at the link in the show notes, or email us at unpacked@afar.com

This has been Unpacked, a production of Afar Media. The podcast is produced by Aislyn Greene and Nikki Galteland. Music composition by Chris Colin.

And remember, the travel world is complicated. We’re here to help you unpack it.