Market Report: Holiday Travel Special w/ The Points Guy!

0:00Haley: Okay, we all love to romanticize being your own boss, but even when you have a team, you still end up being the bookkeeper, the marketing department, and the person rearranging appointments at 11 p.m. And that work isn't just annoying, it is expensive, and it's especially taxing for businesses that run on appointments. So if you own a business that takes bookings, this one's for you. Gloss Genius is a system that runs the operations for you behind the scenes. Scheduling, payments, admin, handled automatically. Payment processing is a flat rate with zero hidden fees. And check out Rebook's clients on the spot.

0:37Haley: Clients can book in seconds too, so there's no login or separate app necessary, so you actually get more appointments. 125 ,000 businesses already trust Gloss Genius to earn them more and save them time. Want to try it out for yourself? Go to glossgenius.com and use code financial for 50 % off your first two months of a premium plan. This is Financial Tea. What's up, Sippers? Welcome back to Financial Tea. This is a very special episode of the market report. I have our first guest, Brian Kelly, friend of the show, the points guy here in Brooklyn. I seduced him to come to Brooklyn. Well, it's close to JFK, so.

1:22Haley: It's okay. Perfect. Yeah. You always have to be close to an airport if you're the points guy, but you are here to do a 911 episode with us about holiday travel. Brian, ticket prices are up roughly 30 freaking percent. Everyone wants to see their families, but you know, this war in Iran is really being the Grinch because our wallets this holiday season, They are barking. So you're here to give us all your best hacks. And yeah, you are in Dumbo where I famously once forced you to move. You lasted about three weeks. It was a good six months. I think I lasted six months in Dumbo. Great neighborhood.

1:55Haley: Story for a different day. But yeah. Those Uber bills. Yeah. They add up. They really do. So that's rent in itself. Okay. Welcome to the pod. I'm being really serious, even though obviously we are best friends because it's like, yeah, shit is really hard. And I'm like, how are we going to get our zippers home for the holidays without spending so much freaking money. So let's just start with the basics. Between the surging jet fuel costs and all of these packed flights, I feel like travelers are really feeling sticker shock these days. I'm feeling it too. Like I said, holiday flights are up 30%.

2:27Haley: So what can people be doing to lower the cost of holiday travel this year? Yep. So the first thing I would do is you have to be strategic. I think people, when they're buying flights, they look once, they look on Google flights. They're like, this is, I don't know, is this a good deal? Isn't it? And then they just book. So first thing I would say is get out of the round trip mindset. Round trip airfare is rarely the best deal out there, especially when you start thinking about points. When you start addressing a trip in one way segments, first of all, it's easier to price like which portion of this flight is more expensive, the outbound or the inbound.

3:07And because domestically, almost all airfare is roughly half the price. It's the same as I always book two one-way tickets for a lot of different reasons. But number one being my plans always change. And if you book a round trip, you have to pay and change and reprice the ticket every time. But if you have two one-ways and say my return, I just want to extend, you don't have to mess with your outbound ticket. You can lock in lower prices. So I think in general, being like thinking in a one-way mindset, not enough people do.

3:34Haley: Okay, I love that. And then with one ways, and I want people to think about mixing and matching. And obviously, I'm the points guy. The way to save money with 20%, 30 % airfare increases is using points. There are still tons and tons of points deals out there. So having points in your arsenal is how you're going to be able to afford to travel in 2027. So when you start breaking down your trips and just focusing on one way on either side, you then can be flexible as well. So maybe I'll pay for the outbound flight. Think about other options to get home, using points for the really expensive, paying for the cheap flights.

4:12And there are tools out there now that will do all the digging for you. You know, instead of having a friend like me that does all the points, you know, a tool, there are two tools I always use. Number one is point.me. So point.me, you can put in, you know, and I always, once again, recommend just doing one ways at a time. Saying, I need to go New York to Paris. I want to go December 26th or 27th. It'll tell you. So if you have transferable points, here are the best deals. And there are still tons of economy. Using award tickets, getting the business class tickets from Tokyo are really hard. But especially if you fly coach or premium economy, there's actually a ton of inventory out there.

4:52So points are not just for people who want to go to the Maldives and first class. Yes, that can be a great redemption. But some of the best redemptions I'm seeing now are on these really expensive thousand dollar flights within the U.S. that you can use points really valuably. But transferring to different partners is where it's at. The U.S. programs generally charge a lot, but they have alliance partners that will charge much less. And so tools like PointMe will actually tell you, transfer your built points to Japan Airlines and get the cheapest tickets, but not on a flight to Japan, even if you're flying their partner British Airways to Europe.

5:28It's very confusing, But now, bottom line, there's technology that will tell you, on this day, this is the cheapest way to go on points.

5:36Haley: So you mentioned that there are two tools that you use. Point me. What is the other one? The second one is seats.aero. A-E-R-O. Seats.aero is especially good if you're flexible. This is the other thing. I mean, you will save money the more you're flexible, meaning what days you can leave, meaning what airports you fly into. So if you're trying to plan your Euro summer 2027, yeah, if you look at cash prices right now, crazy for economy. But funny enough, like award tickets, there's tons of availability even in business class. So one of my favorite loyalty programs for Europe, and I go to Paris every other month, is Air France, their loyalty program Flying Blue.

6:13They have tons of 60 ,000-mile business class award inventory one way. So 60 ,000, think of that. Your credit card point,$60 ,000 is going to get you a$500 gift card or a$3 ,000 one-way business class ticket to Europe. So Seeds.Aero lets you put in, say, New York, you can put in to Europe. You can actually search by month, by year, and you can search. Just show me the dates in June where I can spend$60 ,000 to fly business class. This is how you plan, fly in the front, and on those business class awards, you're spending$200 in taxes and fees. So by being flexible and sorting an entire year's worth of availability and planning in advance, you can still, there's lots of good inventory out there.

6:58Haley: I love that. I think it is hard though, like when you have these holidays coming up and obviously they really come and get you, but it's like, oh, you want to be home for that holiday. Back to the flexibility thing. So putting points aside, if you just want to get a cheap flight, you have to be flexible on the days. I just looked up for flying New York to LA. If you want to go Wednesday to Sunday, it's$675. But if you go Thursday morning to Monday, it's$375. It's crazy. And you know, so especially if you're traveling with kids and a family, that adds up. Here's what, instead of getting in late Wednesday night, which is the busiest travel day of the year, flying 6am the morning of Thanksgiving, sleeping on the plane and showing up in LA at 855am.

7:45Haley: Who cares? And the first morning out flights statistically are 80 % more likely to go out on time. So even if you're not a morning person in general in life, especially over the holidays, so take the first flight out, save a ton of money. Just think to yourself, was my 12 hours of sleep in my family home bed worth that$300? No, just fly Thursday morning. You'll get there. And if you're someone who hasn't booked their holiday flights yet, do you, and you're listening to this episode, should you pull the trigger immediately? Or is there a scenario where it piece to hold off. If you're using cash, book yesterday.

8:18Generally, cash prices, the sweet spot in general domestic airfare is six to eight weeks before departure. But this year, we've seen demand increase as prices go up. Flights sell out, especially over the holidays. So I would book using cash today. If the prices are too high, I mean, this is where using points. I'm a points maniac.

8:38Haley: I know. I haven't booked New Year's Eve travel yet. I may stay home, I may go somewhere, but I'm going to be opportunistic. And this is where using points last minute, and the points people hate when I share this is, but the airlines open up tons and tons of points availability, even the day of, the day before. So all of, I can go to Asia sometimes without a flight home, but I have so many points in different programs. I know as long as I'm flexible, I will always get home. And this is the mentality I want people to have with travel. Another tool is using AI. There's a tool called With Autopilot.

9:11And there's a couple other AI tools out there that you can -

9:13Haley: You can share name names, like whatever ones you're using. With Autopilot's great. You can book a flight and tell it. And it'll automatically keep checking. And if the price drops, they will get you a refund or a credit for the difference. And then they take a cut of that refund. But only if they save you money. So I would challenge you as one for rental cars called Auto Slash. Auto Slash, you can book a car through them. and especially car rentals are really expensive these days. But within a week, they often drop dramatically for last minute. And most car rentals are refundable. But most consumers, we're too busy.

9:47Even hotel reservations, most hotels that you can refund up until a day before, you should be checking. We're all too busy to do that. But these are the tools that will do it for you and automatically rebook. And this is why like AI, we're just on the cusp of the agentic overtaking of the travel world. but trust and believe that the airlines and hotels are using AI to charge us as much money as possible and starting to use our data against us. As consumers, we have to be on the offense as well, using these tools to save us money.

10:17Haley: So, okay. Remind the name of that just so we can all use it. Yeah. So the tool when booking flights with autopilot.com. With autopilot.com. And then auto slash.com for rental cars, where it'll rebook you and save you money. And are there any other AI tools that you are using for travel and for credit card rewards? And do you think it's safe to connect your loyalty accounts? You have to be careful. You know, this agentic world, I use instinct. I love my text assistant. So when I'm going to Paris, I knew that there were going to be strikes with all the protesting going on. But instinct actually told me about a nationwide strike before I read it on the news.

10:53And it allowed me, I had a restaurant reservation at Jules Verne, the Eiffel tower. I was going to take my parents, but I knew there was going to be a strike, which would likely cancel that. So I rebooked the last remaining reservation for the next day. And of course, Jules Verne calls me, they cancel it. And they're like, sorry, we have no other reservations. But I had already rebooked for the next day because I had the intel. So I think using AI for any trip you're on.

11:17Haley: I love that. So something that I notice in your content is when you're actually at the airport, you have this arsenal of apps that you use to make navigating your travel day easier. So I wanted you to walk us through what those are and how you use them, like between the lounge and your delays and all this stuff. I feel like you've really got a good toolkit. Yes. So I highly recommend the app Flighty. Flighty is, you know, if you're an aviation geek, if you love planes. So what Flighty does, you can link up all of your reservations. It'll know what flights you're going on. And it's really cool.

11:52It'll track all your flights. It'll tell you, you know, I fly Air France all the time. It'll tell me you flew this plane last in October of 2024. This plane's been flying since 2009. So from a nerdy aviation perspective, it's really fun. It tells you all the information, but it also updates you. So before you leave the house, even because what happens a lot with airlines, especially the holidays, cancellations, they'll change planes around. And I'm six foot seven. And even in business or first class, I'm very particular in the seat I sit in because choosing the right

12:22Haley: seat on that plane can be, especially when you're tall, it really matters. No, I'm so tall too. And that's, I mean, that's why you started the points guy. And so apps like Flighty will alert you, Hey, there's been an aircraft swap. You're now on a 737, check your seat. And lo and behold, most of the time when airlines do this, you might lose your seat assignment. So every tip I'm giving you today is you need to be on the offense and using technology. So Flighty will say, Hey Haley, that flight you're taking to Tokyo just got downgraded. It's this old aircraft with the really bad configuration.

12:53So flighty gives you up to date before you leave your house, you know, it's a flight on time. It'll even give you stats. Historically, this flight leaves 95 % on time. Oh, wow. And this information is helpful, especially when planning connections. You know, when you're buying a flight, I think it's criminal. So many airlines, they'll still sell 55 minutes in Paris, which is psychotic. Even on the best day, you're going to be stressed.

13:16Haley: Yeah. So don't set yourself up for failure. But there's just so many unknowing consumers out there who say, well, if the airline's selling this, oh, great. So flighty's amazing. I also, you know, I have clear, clear. I also recommend signing up for TSA touchless ID. So anyone listening, if you have TSA pre-check, that ain't enough these days. You need to opt in to touchless ID. You have to go to the airport to do it. You have to upload with all the major airlines, they support it. You have to go into your American Airlines, your Delta, United, you have to upload your passport and you have to opt in to touchless ID.

13:47It's like two clicks. It'll take you two seconds. The best lane in the airport isn't clear sometimes, or even TSA pre-check, it's touchless ID. They're empty lanes and crowded airports. And once again, people will flame me for sharing this tip because the people who know hate when I share this, but, but yeah, so it's just about having opted in before you get to the airport.

14:05Haley: You are very aggressive with your travel and very confident. And something that I see you doing a lot is like, you'll cancel and rebook when the price drops, which you just walked us through. So like, when do you get cash back? When do you get airline credit? When do you get your miles back? How does it work? Are they all refundable? I want everyone listening to really understand most people overlook. I almost always use points for all of my flights because when you use points, in most cases, it's a fully refundable ticket. Why is that? It was actually during the pandemic. They loosened the rules on redeeming points.

14:40So most tickets, now a couple of airlines have basic economy awards, so you have to be careful of that. But if you book in a normal award ticket and most frequent flyer programs, United, you know, say I can book that as a backup. People would be shocked at how many backup flights I have. I changed my flights maybe five or six times before I go anywhere. I love it because I want to get the very best flight for the very best amount of miles. And remember, airlines often drop the price in terms of miles as the flight approaches. So at the same time, when the cost of tickets are going up because they want to fleece those business travelers who have to get to London, Last minute business class tickets to London can be$10 ,000.

15:18But at the same time, you can spend 40 ,000 points. Because the airlines also want to just fill the seats with award ticket users. They want every seat to be open. They want to charge as much possible to those people who will pay. But they'll take award tickets because they're still getting paid on that as well. So it's a way for them to discount without having to forego that really high lawyer that has to pay. I know it sounds exhausting to people, but it's so exhilarating to me. Because you can book one thing, and I just know deep down, better stuff will open up. And I just keep checking.

15:48Haley: How close to the flight can you cancel? You can cancel your flight in most programs up until departure. Oh, whoa. So this is the mentality of understanding the flexibility. But in general, when you pay cash, if you cancel outside, you're getting credits. And I'm the worst with credits. Yeah. I mean, who really has the time to track credits? I hate gift cards, too. You just forget it. I will essentially, I know I will lose the value of that credit. So that's why I almost always just book in points knowing that. But you got to get it back in your trough. And once your points go back, they're back.

16:19You know, there's no expiration. You can easily use them. So I'd much rather do that than be paying and locked in.

16:24Haley: Okay, I love that. You have so many points. Like literally, you are the points guy. But if you're someone who doesn't have a giant points stash, but you just really need that trip home, what is the smartest move that you can make today? I think just use technology. So in Google Flights, it'll tell you if the price is low, medium, high. You can see the price trends for the last 90 days and see. In general, airfare goes up much more than it goes down. So I feel like if you see a price that you're comfortable paying, then just set tools like autopilot that'll keep checking. If it goes down, you save money.

17:01But I think if you don't have a lot of points, the bigger wake-up call is, this holiday season's expensive. Guess what? 2027 is going to be expensive. Guess what? next holiday. So in order to save, you have to get in on points. That's the bottom line.

17:13Haley: So what credit cards should we get? Like, are there any really good bonuses right now? There are huge bonuses out there. So even if - What's like a juicy one? Like give us a big one. The easiest way, you don't need to be the points guy to get tons of miles and points. The beauty is credit card companies will give you 75 ,000, 175 ,000 points just for getting a card. So if you're an everyday person, as long as you have a good credit score of 700 and above, you can be getting one or two new credit cards a year easily, as long as you pay them off in full. But the signup bonuses are - But you're supposed to keep them forever?

17:45Haley: No. I mean - Drop them down to no - I would say with every credit card, if you're getting value out of the perks every year, and let's just talk one. The Capital One Venture X card is the biggest no-brainer that I full throttle stand by because it's$395 a year, but you get$300 a year in free travel off the bat every year. So that really takes - Does it apply it automatically or you have to use it? Yes, yeah. It's very easy to use. So really you're at$95 a year for this card. And they give you 10 ,000 points a year. The 10 ,000 points at the very base level is$100. So walk through the mask. So Venture X, you are earning$5 a year.

18:23And this is a credit card that gets you into all the beautiful Capital One lounges for free. It's a premium credit card that you earn 2x points on everything. And that card has a 75 ,000 point signup bonus, which is enough for one white business class to Europe. You know, so thousand dollars, several thousand in value just from the signup. You're getting lounge. That is a great starter premium card that it pays for itself every year. The other two cards I'll recommend second would be built palladium. So if you pay rent or mortgage built palladium, you can earn points on that. It's 50 ,000 built points.

18:58Bill points are the most valuable points currency out there. They transfer to a ton of different partners. It has a$495 annual fee, but a ton of different perks that pay for that. And then the final one, I mean, there's a lot of other ones I could get into, but Amex Gold is a great 4X on dining and groceries, which we all spend on. And there are targeted offers with Amex Gold. You get 100 ,000 points or more, and that card has a lot of real value every day. So those are a couple of the cards that I'm like, feel very comfortable that you start out with and that could easily get you a free trip.

19:33Haley: I love that. And okay. Just have two more questions. I know you're a busy man during the holiday season. I feel like there's so many delays and cancellations. So walk us through what happens. Like if you get delayed or canceled, like what are, what's our toolkit? What do we do at the beginning? Who do you contact? Yeah. Is this when you would automatically just go on your phone and book that next awards flight as soon as possible? And what about a refund or voucher? So if your flight is delayed or canceled, if it's delayed three or more hours or canceled, unfortunately, you're not owed anything but a refund.

20:08Now, a lot of airlines will try to give you a voucher. Never, ever take a voucher. You are owed a full refund in the form that you paid. If you paid on a credit card, never take a voucher because, once again, we're going to lose the voucher. We're going to forget about it. Cash is king. So always say, no, this flight's been canceled. I want a refund. Um, but you know, really the airline has an, you know, they can give you a refund or they can try to get you home so they can offer you options. But if the option is like the next day, um, and they don't, they're not, they don't have to put you up in a hotel, even if it's their fault, they should.

20:43And most have policies saying they should. And based on availability, they might give you a horrible hotel, but here's what I do instead. I'll immediately go to the airline app, see if what they have available. A lot of the airlines are good. They'll say, here are the flights. You know, rebook yourself. Do that instantly. Never wait in the line. Never call. Self-service first and foremost. And a lot of airlines have actually good, pretty good AI chatbots where you can just say, hey, book me on this next flight. I use a tool called Expert Flyer, another tool I use. It's a little bit more advanced, but it'll show you on the route you're flying all the airlines that have availability.

21:16Now, most airlines won't put you on a partner, but you can go nicely up to a gate agent and say, thank you. You know, my flight's been delayed or canceled. I have to get home today. Can you please, there's availability. I see that there's, you know, why coach availability on this flight on a partner? Could you please, you know, put me on that partner? Never hurts to ask. You always have to be nice. No jerks to customer service reps. I don't care what you say. Promise me this, you know, just be super nice. Even if you're upset, even if they're being mean to you, smile through it. Trust me. It never pays to be mean to them.

21:47Long answer to a short question is like, you don't really have many rights in America. There really is no passenger bill of rights. This administration is not going to be adding consumer rights anytime soon. Don't hold your breath. Advocate for yourself. But what most people don't realize, your credit card. Many credit cards have flight delay and cancellation coverage. So you can go to your sugar daddy bank, which has much more money to give out for delays. And a lot of travel credit cards, if you have an overnight delay, they'll pay for up to$500 per person for a hotel. So don't take the Motel 6 or is it Motel 8?

22:20Haley: Brian's been at the Four Seasons too long. Don't take the motel six credit when your credit card will pay you to stay at the JW at the airport and you get reimbursed for meals and Ubers as well. Okay, last question. I am flying back from Japan the day after New Year's. My sanity is really banking on a lay flat seat. So right now I have this crazy route where I'm going through Seattle and it's a six hour layover. And so I'm just wondering, should I keep that and just monitor on points.me and Seats Arrow up until the day before the day of? I'll say this. So jet lag, so time shifter is the jet lag app.

23:09I'm an investor of, and actually New York to Tokyo is the worst route for jet lag. You're busy. I want people to think about flying. Like you're busy. You've worked hard. You have points. use them for live flats so you can sleep so that you're well rested it's worth it in your case the non-stop to new york there's nothing open right now so i would this is it's all about changing your mentality and travel so hailey this is my challenge to you in the new year new year new hailey so yes you have like a six or eight hour layover in seattle so you can look at that as i'm like oh i'm just going to be in the airport but no go to centurion lounge or better yet this is what I do.

23:44I love Black Lane. Black Lane is, you know, the black car chauffeur service. I had an eight hour layover in Santiago, Chile recently. And instead of sitting at the, even at a lounge, I'm like, I don't want to sit in a lounge. I got a Black Lane sprinter van with my parents and we went around Santiago, Chile.

23:59Haley: And it took your luggage in it? Yeah, it took your luggage in it, pop around. I would do that with Mr. Dow Jones, have a cute little January 2nd day date in Seattle. Yeah. Do something touristy. And so instead of viewing that layover as like, oh, I'm going to be so tired. No, you're going to be able to sleep in your lie flat. I think everything is just changing your mentality. Layovers can just be an opportunity to see a new city. But really what I want you is have that as a backup, but just know, keep monitoring using the tools we talked about today. And I'm going to use my AI. Problem with AI today is that each and every airline loyalty program, they're not, the AI tools are not fully integrated yet.

24:34Like Google Flights is starting to do AI award search where you can say, hey, book me in like with American in Alaska. So you're My instinct agent can't go and check award inventory at the level I would like it today, although it's getting better. But I don't know. I mean, maybe actually ask instinct. Give it your credentials and say keep checking the Japan Airlines website for a business or first. And if anything opens up, text me immediately. But that's the mentality. Start thinking of like just how am I going to be on the offense? It's not like, poor me. I checked on this one time and date and there's nothing.

25:07Therefore, there's nothing. No. There will be stuff, Haley. I guarantee. I love it. We're manifesting. If your mentality and you, you know.

25:14Haley: It's so true, Brian. I love that. So, and in a worst case, you have your flight home via Seattle. You have a day date and it's a long day of travel, but it's the cap off to like an amazing trip to Japan with your lover. My lover. Okay. So any final words of wisdom to everyone who's like freaking out over how expensive travel is? They want to get home for the holidays. Basically TLDR, use your points. TLDR, you've got to get in on the points game. unfortunately the travel you know unless the war in iran ends tomorrow not likely gonna happen i can't sit here in good conscience and be like flight prices will go down next year but what i can tell you and having done the points game now for 30 years i've redeemed in 1996 the points game is how you want to travel and just you don't have to be an expert get a couple credit cards maximize your spend pay your bills off in full every month avoid interest bank up points and teach yourself the language of points and have that confidence.

26:07Because I assure you, whether your flight's canceled, delayed, it's all going to happen to you. But when you approach travel from a confident mindset, maybe a little delusional, it's all fun anyway.

26:19Haley: The Lulu is perfect. The Lulu in 2027. Yes. Stay rich, everyone. Thank you, Brian. You have to come back because we'll have more travel questions soon. Oh, I'm coming to Tokyo with you. You're coming to Tokyo. And remember, Sippers, rate, subscribe, review. We are up for renewal. Every like, review, subscribe really counts. And yes, stay rich and happy holidays. We hope you get home safe and cheaply. Safe travels. Safe travels.

26:48Here at the Happiness Lab, we're serving up some hot takes for the summer. Big ideas that just might reshape how you think about your well-being. Like the radical notion that we should get rid of small talk completely. We talk about current events. We talk about what you do for a living. But not, do you love what you do for a living? Is this your dream job?

27:04Haley: For more surprising ideas backed by psychological science, check out our new series, Happiness Hot Takes. Listen to The Happiness Lab with me, Dr. Laurie Santos, wherever you get your podcasts.