Why Travel Rewards Might Not Be Worth It Anymore With Chris Hutchins

22:29Now, when someone's building out a strategy, let's say, for example, let's look at travel, for example, and they're building out a strategy for next year. So we have this community called Master Money Academy that we kind of go through. And we've had a lot of questions over the course of even just the last week of people saying, hey, I am trying to build out a card strategy for next year, for next summer, I want to start traveling with my family. And so we want to build all of this out. And we've gotten all these questions coming in. How far in advance would you start to open up cards when you are trying to build out a strategy to start travel for free?

23:00I think that there are three things. So one, let me just remind people, none of it's ever actually free, right? Because you have this opportunity cost that if you open up a bunch of cashback cards and you spend all your money on cashback, you would just have money, right? And whatever opportunity cost there was of the money you could have earned otherwise is what that free travel with your points costs. So keep that in mind. That said, as someone who's opened up a lot of cards, spent a lot, earned lots of points and miles, used it to travel around the world many times, I think there's a lot of outsized value.

23:31Here's how I think about when to plan and how to plan. So depending on how much flexibility you have really dictates how easy it is to book your trip. So the two big factors are how flexible are you and how many people are traveling. Because there are a lot of airlines where if you're traveling by yourself and you're super flexible and you want to take a trip next summer, you could open up the card next spring and probably be totally fine. If you are four people and you want to travel in business class to Japan during cherry blossom season next year, like it's a little late to do it at kind of schedule open.

24:07So you're going to have to be really going last minute and, you know, hoping and praying that it's going to work out. So I think the big question is how flexible are you and how many people? So for next summer, I would say you want to have the miles as soon as possible because you never know when availability is going to open up. And flexibility wise, I would encourage people to think not about, oh, I live in Denver and I want to go to Paris. And, you know, maybe there's a direct flight from Denver to Paris. So you're thinking, let's see if that flight's available. That is a way to look at things.

24:40But another way to look at things is, is there a flight anywhere in the middle of the country or even the East Coast that flies to somewhere in Europe? And can I find a seat on that flight? And worst case, if I have to buy a ticket with cash from Denver to Chicago, or maybe I find a flight from Denver to Frankfurt and I have to buy a flight or take a train from Frankfurt to Paris, oftentimes those little what we'll call kind of positioning flights or even positioning trains will be a couple hundred bucks. So if you can save$3 ,000 on your flight across the ocean because you flew out of a city that you had to pay$100 to get to or$200 to get to, it could still be a really good deal.

25:19So when I say flexibility, it might be what route you take. It might be what day you fly. It might be how many layovers you have. It might be how soon you find out where you're going. I told my wife this. So we're planning on going to Japan for spring break. And I was very diligent. I had the miles ready more than a year out because I knew that Japan Airlines releases business class seats at 361 days to a couple partners. So I'm all ready to go 361 days out, but they only released two seats. So I couldn't even planning one year in advance. I couldn't even get all four of us on the same flight.

25:58So I got us on two seats flying from San Francisco to Tokyo Narita and then two to Tokyo Haneda because they have two airports there. So we were on separate flights, but I told my wife, I'm confident that between now and departure, almost a year later, something will happen. Whether that's two seats on one of those flights open and will change, whether that's American Airlines opens up four seats from Los Angeles, you know, like I didn't know what it was, but I knew something would happen. And so I told her, I was like, we're going to be together. I just can't tell you whether we'll find out at the airport.

26:29Like we'll go to the airport ready to leave three hours from now and four seats will open up on a United flight and we'll change everything. But I knew it would happen. Sure enough, it did happen because Capital One announced that they were adding Japan Airlines as a transfer partner. And a lot of airlines make availability open just to their program. And so, yes, you can book Japan Airlines flights from any of their partners, American, British Airways, but they make more seats available to their own program. So we were able to transfer a bunch of Capital One miles to Japan Airlines and book all the seats we wanted.

27:02We're all on the same flight together over and back. My wife's so excited about that. The trip kind of all came together. But had I not had miles in Capital One, I literally, there was no other option. You can't transfer to Japan Airlines from Amex or from Chase. So I would say if you have a trip and you're very specific about what you want, plan more than a year out. If you're really flexible and you're willing to take layovers and your dates can be changed and you'll pay a couple hundred bucks to fly out of a different city and change planes, plan as soon as you can, but it's not as urgent. I don't think that's where it comes into ABA, always be acquiring points if you're going to be looking for, you know, doing some of these big trips.

27:38And if you want to do them annually, it's always just trying to kind of grab those points whenever you can. And I think that's really important was the way that how flexible you were based on those plans and how you're actually going to get there, I think is really important. Now, when someone is thinking backwards on this, and they are looking at trying to have a card strategy and how they open up cards, and they're going to try to acquire points over the course of the next couple of years. How do you think about that? If it's someone like who just needs to get cash back points where they want one or two cards, it's someone who is willing to kind of optimize here.

28:07What is your strategy and how many cards you think they should open at a time? I know it's based on your spend and all those types of things as well, but how should they actually think about this and what cards should they actually target and look at? So the prereqs I would ask yourself are, you'll agree with this. The number one is, can I afford to do the spending? Because we don't want to carry balance. Carrying a balance isn't worth any amount of points. So let's keep that as like rule one. Can I pay off all the cards that I'm going to open? So let's set that aside. Then the question is, you know, how much am I spending?

28:34Because the last thing you want to do is get a little too excited, open up a bunch of cards, and then not be able to meet the requirements to get that bonus, right? A lot of times it's earn 100 ,000 points after spending$8 ,000. Well, if you don't have$8 ,000 of expenses that you could spend in the next 90 days or whatever that requirement is, it's not going to be a better deal to get points if you have to buy things you don't need. Now, there are always ways that you can kind of shift your spending, right? Some utility companies will let you prepay more than your balance do. Maybe you can buy gift cards to your grocery store or to Amazon or something.

29:11Or maybe you wait and do it around the holidays when you have more spending than maybe in the summer. So I think there are ways to, without spending more than you need, maybe kind of shift things around so that you are hitting that bonus without increasing your annual expenses. But how do you think about how many? So ultimately, you're going to be limited by your spend. So I would be thinking about that. You're also going to be limited by the kind of application rules of lots of different banks. Chase has a 524 rule. You can't open up a new card with Chase if you've opened up five cards in the last 24 months.

29:44And it's not an official rule that you'll read about on their website, but it's just about as official as it comes. And if you Google 524, there'll be a thousand blog posts that detail all the nuance of it and how some business cards don't count and all that. So I would be prioritizing the banks that are probably more strict. Capital One's a little bit more strict. Chase has a 521 rule, whereas Amex is probably a little more willing to give out cards. Maybe Bank of America also. City somewhere in the middle. That's kind of a high level guiding principle. and I would say after that, I'd be focused on what's the highest bonus, right?

30:18Like I would much rather have a card that was gonna give me 100 ,000 points than a card that would give me 20 ,000 points for opening it. And I'm probably not the best example of this because there are people who open 10, 20 cards a year, right? And they're earning millions of points every year. I'm not quite as aggressive as that right now, but earlier in my life where I didn't have spend and I was traveling more, I probably was. and you'd be surprised at how opening more cards doesn't have the impact that I think a lot of people think it will have on their credit. There was a really cool post someone put on Twitter a couple of years ago where he and his partner mapped out their credit score over 18 months while they opened like 20 credit cards and both of their credit scores went up.

31:01And so the influence of how many accounts do you have, how much of your open credit are you spending? If you have$20 ,000 a credit limit and you spend$5 ,000 a month, you're using 25%. If you open up a bunch of cards and now you have$100 ,000 a limit, you're still only spending$5 ,000 a month. You're only using 5 % of your limit. That feels to a bank safer to lend you money knowing that you're not maxed out on your current cards. So there's a lot of reasons why opening new cards can actually help your credit, especially in the long term, right? It will have an impact in the short term. You have a couple new inquiries that you get every time you open a card.

31:35Average length is going to be shorter. So it will have an impact. I did like like an hour deep dive on credit scores. And I went through all of this in a lot more detail, but it will have an impact. But in the long run, it seems that for most people, the impact is positive. Exactly. I think the utilization side of it is just a huge, huge deal because overall, they kind of did some studies looking at people with credit scores that were over 800 and their utilizations on average were about 7%. And it's because they had probably more cards open and just more opportunity to be able to lower that utilization rate.

32:05So over time, I can definitely see that happening because it's a huge, huge impact on your credit score long term. So for sure. And I think as we start to look at your framework on how you open cards, are you looking at flexible points first? And then once you do that, are you looking at airlines and hotels? Or what is your kind of order of operations when you're choosing those cards? So I think one of the tricky things you can end up doing, which can work against you is if you focus just on the best bonuses, you're like, okay, well, I'm open this card up and I get 200 ,000 Capital One points.

32:33Then I'm going to do this one and get 175 ,000 Amex points. And I'm going to do this one and get 100 ,000 Chase points. That's not the worst strategy. Right now, you have a lot of points, but they're in three different programs. And if you look at transfer partners of all these airlines, you'll see that there's a lot of overlap, right? So if you go to all the hacks.com slash TP, I have a spreadsheet you can pull up and it shows all the transfer partners of every airline. And something like British Airways, Avios, or Air Canada, Aeroplan, or Air France, they're partners with most of the programs if not all of them and so if you're transferring your points to a program where all of the points transfer so if you're like avios is a transfer part of everyone air france is everyone except this new home ownership card called mesa so if it turns out that the flight you want is on air france this was a great strategy because you got way more points and by the way when i say on air france i actually mean bookable with air france It's very possible that flight is on Delta or KLM or some other partner of that airline.

33:35When I say Air Canada Aeroplan, that doesn't mean you have to fly Air Canada. You can fly United, you can fly Lufthansa, you can fly Swiss Air, you can fly Eva Air. Like there are a lot of, there are these three big alliances with anywhere from probably 15 to 30 airlines. And they allow partners to book flights. Now they don't allow partners to book all the flights. So like in the Japan Airlines example before, sometimes having points in a specific airline is more valuable than having points with their partners. But there are a lot of these programs where you can transfer from everywhere. However, let's say you want to go to Asia and you can only find good flights to Asia on EVA Air or Japan Air.

34:14Well, they are not partners, either of them, of Amex or Chase. And so if you earned a lot of points on Amex and Chase, but you earn no Capital One or Citi points, and now the flight you want is only available on Capital One or Citi, by transferring to those two airlines, you're kind of out of luck. So that's definitely probably an advanced strategy. At the outset, I would probably focus on earning the most number of points in one program and then get to a point that you have enough points to book one trip. So if you're a solo traveler looking to fly in coach, maybe that's 100 ,000 points. If you're a family of four looking to fly internationally in business class, that might be 800 ,000 points.

34:52It's a very different answer depending on what class you want to travel and how many people. And then once you have enough points in one program, then I start thinking, okay, let's get a second program. Let's get a third program. Now, there are also cases where your personal financial circumstance might make it worth getting other programs. So if you're a homeowner, the Mesa card is super interesting because you earn up to 100 ,000 points a year on your mortgage. If you're a renter, the Built card is interesting because you're going to earn up to 100 ,000 points a year paying rent. And so there are programs that might be worth getting separately from like these big welcome bonuses just because there are some really lucrative opportunities to earn points based on paying rent or owning a home.

35:35But for the most part, I try to accrue in one program until I have enough for a trip. then I go to multiple programs, which just gives you more and more flexibility. And for those of you out there who haven't heard of the Mesa program or the Built program, both those cards are basically, you could pay your home costs. So like your rent or your mortgage, you can pay on a credit card and actually acquire points on those, which is a really, really powerful thing that we haven't had available to us in the past. It's a huge thing that you can do because you spend so much money on that stuff. And so those are just free points that you can go out and get for sure.

36:04So the Mesa card, by the way, is even crazier because you don't even have to pay your mortgage. You just have to have a mortgage. So you upload your mortgage statement and say, hey, we spend$4 ,000 a month on our mortgage. And as long as you spend $1 ,000 a month on their card, they just give you 4 ,000 points. You don't even need to pay the mortgage because a lot of people think, oh, how am I going to pay my mortgage? I have to go on this portal and I have to say, they don't take credit card. How am I going to make this work? Nope. You just tell them you have a mortgage. They one month in say, verify this, upload your mortgage statement.

36:33So don't tell them you have a$10 ,000 mortgage because they're going to ask. If you do, great. But if you don't, that'll be a problem. But so it's that easy. And with Bilt, they'll mail a check to your landlord. Your landlord doesn't have to accept credit cards to do it. So those are kind of like free gimmies. Like if you have a high enough rent or mortgage that it's kind of a meaningful number of points, I would look at both of them. For sure. I think that's such a huge tip for anybody. Anybody can utilize those because somebody's either paying rent or mortgage unless you are living with someone for free somehow.

37:02So for sure, that's a huge one. And now let's get into some tactics and optimization when it comes to some of this stuff. What are some of your favorite transfer partners right now? Because I think some people out there who maybe aren't even aware that transfer partners exist. And we talked about Chase on our last episode and some of the transfer partners that are available there. But what are some of your favorite ones now that offer some of the best redemption value? Yeah, so this is an interesting one. So first off, I did this episode 166. And I would actually look for it on YouTube. You can go to allthehacks.com slash 166.

37:32and I went through all the best award tools. And so I want to explain this because I think people get really caught up here. They think, okay, so Chris is going to tell me that Air France is the best place to transfer my points. I don't have an Air France account. I don't even want to go to France. Like it seems a little crazy. And I'll point out that one, you don't have to learn all of this because there are a couple tools out there. If you don't want to watch the episode, you can go to awardtool.com or pointsyeah.com are two I really like. and they will search for availability using all these other programs.

38:06And you can even tell them, I only want to search for flights I can book with chase points. And they'll come back and say, oh, you want to go from the East Coast to Europe with chase points? Here's an option. Or they both have some way where you can say, just inspire me. Like I live in Chicago. I have chase points. Where can I go? And they'll show you the best deals you can get with your chase points out of Chicago. So I love these two award search tools. At the end of the day, I would say I'm agnostic to the transfer partners. There are some that I would never transfer to and I don't love. It doesn't matter to me.

38:41I go where the flights are. And so I've gotten a lot of value recently out of Air France because they've just been one of the airlines that releases more than two or three seats, which with someone that has a family, that's really, really advantageous. I really like United and American and Alaska. I'd put Delta in here kind of for the policy reasons, which is you can book flights on those airlines and cancel them with no fee. So if you're booking a American flight or a United flight and you need to cancel it, you get a full refund. All your miles get redeposited. Any taxes you paid get redeposited.

39:17So it's really great for the strategy I'll call of like good enough first, which is we want to go to Europe. We'd love to go in business and we'd love to go direct. But that's not available right now. I hope it becomes available in the future. But I can book a premium economy flight on United for more miles than I want to spend, but it'll work. So I book it on United knowing that we have something that will work. And then I set alerts using all these award search tools for better stuff, like the direct flight in business or maybe a flight from LA in business. And if those things come up, cancel the United, book the other one.

39:51But I have something. so I can start planning the trip, right? Because it sucks if you're like, I think we're going to be able to get to Europe. It's like, well, where do you book your first night hotel? Like, when are you going? When do you request vacation from work? So I like to go and say, let's book something that'll work. And when you use those US carriers, it's great because they're totally refundable. Air France, you can refund it, get all your points back, but you might have to pay a$75 fee. So it depends on the airline, what the program fees are for canceling. Which one do I like? honestly whichever one has the flights I think that I found a ton of recent opportunities with Air France and Air Canada they're probably the two that I think if you told me I had to ditch them they would be near the end of my list of which ones to ditch because Air France I think has a lot of availability and Air Canada has the most number of partners I do love Alaska American United they just have fewer programs you can transfer from so only city transfers to American only built transfers to Alaska, only Chase transfers to United.

40:52So those are good programs, but they're harder to accumulate points that you can transfer to them from because they just don't work with every program. Whereas Air Canada, Air France, and British Airways, Avios, those three programs cover your three alliances, and they all work with Chase, Capital One, Amex, Built, City, Wells Fargo, except for Air Canada. They don't work with City and Wells Fargo, but like a lot of options. That's huge. And I think a lot of people, what they do is they don't understand these transfer partners. And so what they'll do is just go into the travel portal and they'll book all of their travel there.

41:27Do you ever use the travel portal or are you only using transfer partners? And how do you decide between those two when you're booking a trip? I don't think I've ever used the travel portal. And that's primarily because I think I've done this enough. And I'm not saying you shouldn't, right? To be clear, I think there are a lot of people out there who would get tons of value out of using the travel portal. So I'm not trying to dissuade anyone from using it. I think you play this game enough and you start to understand how it works. And I have a really flexible job. My dates are flexible. I can get more value not using the travel portal.

42:00So I don't. But that's not to say other people shouldn't. If you're not flexible, you might never get more value using your points by transferring them to airlines. It'll be really hard. And so anything that lets you take a trip, I think is worth doing. And so if the travel portal is how you're able to take a vacation and see the world and travel and enjoy life, by all means, go use the travel portal. But if you're really flexible and you want to get a little bit more value, you might get that from transferring. There's two particular reasons where I think the travel portal probably can be a better deal than other situations, and that's with Chase.

42:33They have this points boost program, and there are times where you might get two cents a point out of your Chase points booking United flights. If you see that points boost and you're seen like, wow, this would cost you 100 ,000 points, but$2 ,000, that's a way to know you're getting two cents of value out of your points. I don't know. If I saw those deals, I might use them. I'm okay with two cents a point. I like getting one and a half cents or more for my points. So I'm usually transferring, but the Chase points boost can be worth that. And if you have an Amex business platinum card, you can select one airline, which is the airline you get reimbursed for with your airline credit.

43:11And anytime you book flights in the travel portal, they give you a 35 % rebate if you use points. And so you end up getting effectively about 1.54 cents per point. So if you're using your points in the travel portal getting one and a half cents, you should feel fantastic, right? Could you get two cents or five cents transferring? Yes. Is it going to be a lot of work and you got to figure it out? Also, yes. But I'd say if you're only getting one cent, then I am okay with that if those points were earned via signup bonuses. But if you're spending on a card, not earning signup bonuses, cashing them out on the portal for one cent, I would encourage you to look at cashback.

43:48I think that's a big difference maker there because if you're not getting the true value out of that and you're just booking to the travel portal every single time, then cashback is probably a much, much better deal overall. And I think a lot of people need to look at that prior to doing some of their analysis on this. Now, how are you personally dealing with the rising costs of award charts in terms of, I know there's less availability. I know it's fewer sweet spots than there used to be. How are you thinking about that? Or is it just a patience game? I think it's a combination of patience and flexibility and diversification.

44:18So how am I thinking about it? Trying to earn more points in different places. Trying to make sure that I'm a little bit more flexible. So Diversified gives me more programs I could transfer to. And so, yes, the reason why I would say these transferable points, so for anyone not familiar, you could transfer your points to different airlines and hotels like we've been talking about. The reason why those transferable points are so valuable to me is if I have an Amex point or a Chase point and one of the airlines that they partner with is really expensive now, it doubled the price, great. Well, I still have a dozen others I can use.

44:51Whereas if I were only earning points with Delta and Delta a long time ago made a switch that really devalued their points. I would say it is almost impossible to get outsized value out of Delta miles to the point that I have no interest in accruing Delta miles. But there was a window of time where I've used Delta miles decades ago for really, really great value. If you were only accumulating Delta and all of a sudden you went from being able to get five cents out of your Delta miles to one and a half or 1.2, boy, would that be frustrating. But if you had Amex points, well, okay, so now you just don't transfer them to Delta.

45:26That's fine. You're not worried about it. So that's why I like transferable points. And the more you have, the more flexibility you have, the more you're able to be flexible with your dates, your travel, your style, like where you go. You're like, oh, you know what? There's 10 places I want to go next summer. I'm not committed that I only want to go to Switzerland. Okay, well, now you have a lot more flexibility. I think it's gonna be a lot easier to book that trip. Exactly. And then the other is I'm just like making sure I earn more points, right? Like, yes, they've gone down, but 300 ,000 point signup bonus.

45:55Like, that's insane. Like, I've never seen that in my life. And you can do that right now with the Amex Business Platinum. If you find the right browser or sometimes the offer isn't 300, but for a lot of people it is. And if you find a 300 ,000 point signup bonus, well, you just don't worry about the fact that your award flight costs 20 % more because you're getting 2x the number of points when you open the card. Exactly. And I think just having those transferable points, that's always the first place I always focus on, too, is just trying to find cards that have those transferable points because it's just one of the most flexible things that you can do.

46:24It's just pure flexibility is what you really want when it comes to this game. Summer's right around the corner, and this is the time of year where I want to be planning trips, not stressing if we can afford them. And the goal is to actually enjoy the summer, knowing everything with our money is already handled. Monarch is the personal finance app that tracks everything from accounts, investments, savings goals and spending. Get your first year of Monarch for half off, just$50 with promo code PFP. One thing Monarch helped me realize recently was how easy it is for spending to creep up without noticing.

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49:47New summer arrivals are at Nordstrom Rack stores now. Get ready to save big with up to 60 % off brands like Rag & Bone, Levi's, Adidas, and Free People. Join the Nordy Club to unlock exclusive discounts, shop new arrivals first, and more. Plus, buy online and pick up at your favorite rack store for free. Great brands, great prices. That's why you rack. So, you mentioned recently that you've taken optimization too far. Can you tell us that story and what happened? There's not one particular moment where it was like, Oh, that was it. I took it too far. But I just started thinking about, am I valuing my time enough here?

50:27There have been little moments where my wife and I were joking about trying to sell stuff instead of kind of give it away. And then we were like taking pictures, dealing with people on Facebook Marketplace for an item that costs$15. And you're like, did we just spend two hours to try to sell something for$15? Like, what are we doing? Like, how are we using our time? And I think the same goes for a lot of points games and deals. It's just like, where is your threshold for when you're going to try to get a deal? And if you're buying something that's$10, are you going to go search all the cash back portals?

51:00Are you going to look if you have card linked offers? Are you going to try to find coupons? Or are you just going to pay$10 and move on? And so I think I've tried to scale back where I focus my optimization on and let things go, which is so hard. As someone who likes money and doesn't like throwing it away, it's really hard to turn down a few dollars for free. Like if you're walking on the sidewalk and you saw$5, well, yeah, you'd stop and pick it up. But if you ordered groceries on Amazon and you ordered them to make dinner and they showed up three hours late like they did last night at our house, so we had to figure some other plan out for dinner, and now we have some ingredients that we don't really need because we weren't able to get them in time for dinner, I'm pretty sure that if I go and I message Amazon and I open up a live chat and I explain that this thing got delayed and now we weren't able to make the recipe we wanted.

51:49And so now the red curry paste that was$4.79 or something, you know, now we don't really need it. I'm pretty sure they'd refund the$4.79. Do I want to spend 40 minutes like going back and forth and negotiating to get$4.79 back? I try to think, well, when I have free time, I don't hop in the car and go drive for Uber or DoorDash, even though I could probably make 20, 30 bucks an hour. So why would I spend 30 minutes trying to get$4 back if I wouldn't spend 30 minutes driving for DoorDash? You know, like that's helped me kind of change my mental model, which is if every minute that I'm not driving around for Uber, DoorDash, Lyft, Instacart, whatever your gig economy profession of choice is, For every hour I'm not doing that, I am paying$30 or whatever,$20, whatever the rate is in your city.

52:37So I've got to at least value my time for that. And it sucks feeling like you leave money on the table sometimes. It's like, oh, I bought this thing and the price dropped by$3. Should I like return it and rebuy it? It's like, well, yeah, I'd save$3, but I'd have to drive to UPS and drop the thing off and then wait for it. And so, I don't know. It's more of a, I've noticed myself trying to maximize too many areas. And I've tried to just pause and say, like, is this worth the time? And as someone who likes money, it's hard. But if you don't do it, you'll never have time. And it feels like time is the limited resource.

53:12And it's easy for us to all say that. Of course it is. But to start acting on its behalf is really tough. And I think that's one thing that you and I, you know, we were in our 20s. both of us are kind of the same in terms of like we were pursuing financial dependence and we were looking to become optimizers. You know, we were frugal. We were trying to find ways to save money. It's hard to kind of get that mindset shift as time goes on. But once time becomes a more and more finite resource and you look at it in a way, especially when you start having kids and stuff like that, you see how valuable time truly is because you have way less of it.

53:43And so when that happens, a lot of times these things can start to go by the wayside a little more. I remember even like used to drive around to try to find the cheapest gas. Now that's like the dumbest thing I could do with my time is trying to find, you know, save 25 cents a gallon or whatever else it is. And so there's things like that, for sure, that I think a lot of people probably just think through and they want to cut out some of the optimization. But I think that's just part of life. And it's part of growing as time goes on when it comes to that time frame. So what is the biggest win that you have ever had from playing the points game?

54:10Hmm. It feels ridiculous to say this, but there's just been so many memorable trips that like, Like it's hard to say one is the biggest one. And I hesitate from focusing on the biggest value because that's not really the point. Like I could tell you about a trip where we got 10 cents per point. But the biggest thing is probably, and this is probably recency bias, but my wife and I went to the Paris Olympics and we actually did it by accident because we just set alerts to go to Europe and we were like, we were going to take a week off and we were going to go to Europe and seats opened. And I didn't even look at what the dates were.

54:45I just booked it because we were like really flexible in the summer. My parents really graciously offered to watch our kids for a week. So two seats open from SF to Paris nonstop in business. I saw the alert come in because a lot of these award search tools, you can set these alerts. I went into the Air France site. I transferred points from it. I don't know if it was Amex or Chase. And then I booked it. And then I noticed, oh, it's the Olympics. Like we were going right in the middle of the Olympics. And my wife is a huge fan of the Olympics. So I was like, hey, guess what? I guess we're going to the Olympics.

55:13And she was like over the moon. She thought it was so cool. But I looked and like flights to Paris direct from San Francisco during the Olympics were so expensive. And in hindsight, I should have planned a trip to the Olympics anyways. Like my wife was so excited. I can't believe I'd never crossed my mind to just go to the Olympics in Paris. But we stumbled upon it. And if I had the foresight to do that, I probably still wouldn't have acted on it because flights were super expensive. But these tickets were 50 ,000 points each way. And so we actually got a really good deal. and it allowed us to go do a thing we wouldn't have otherwise done that was like such a magical, memorable experience.

55:49And so we used chase points to transfer to Hyatt to book a hotel room that would probably, actually not would probably, you know, one of the really cool things about the Olympics was they made all the cancellation policies so strict that people were kind of scared to book because they knew it was non-refundable. But we kind of were like, you know what, we're going. And so there was actually a lot of availability. So you could get$1 ,200 hotel rooms for tens of thousands of points. It was amazing. And so we wouldn't have taken that trip if it weren't for points and miles. It wasn't necessarily the best value, but it unlocked the coolest experience.

56:21Now, there's probably other ones that are honeymoons and family adventures and other things that were also equally as great. But I think you mentioned earlier, if you're really pushing on the financial independence path, maybe cash back is a more valuable thing for you. For us, we realized that travel was really important to us. Like we really wanted to go and meet people from other cultures, experiencing other things, like have these experiences. And they were the most expensive line item in our budget. So the cheapest way for us to achieve financial independence was to try and mitigate the largest variable cost.

56:53And to do that was to play this game. And so we were able to reduce our travel cost every year to a very nominal amount by playing this kind of points and miles game and traveling maybe more flexibly, but ultimately to places we want to go. And so in a way, earning points and miles has been one of the fastest things to accumulate financial independence for us. For other people who don't travel, that probably wouldn't be the case. But for us, that's kind of maybe the most valuable thing was that it cut out this huge variable cost and let us accelerate our path to financial freedom. And that's the biggest difference for a lot of people out there is when you try to figure out which way you want to go.

57:28If your goal is not to travel, it's not what brings you value. If that's not part of your dream life, then really cashback could be the best option for you overall. Now, you've been to dozens and dozens and dozens of different countries doing this. What is the most ridiculous thing you've ever done to hit a signup bonus? I don't know if this is the most ridiculous thing, but there was a window where we just weren't spending a lot, but there was a really kind of lucrative bonus. And so I think we just bought Whole Foods gift cards. And I think we prepaid our annual, like the entire year's worth of groceries because we weren't spending that much that we could hit the signup bonus on our own.

58:01So we were like, well, we live down the street from Whole Foods. We buy our groceries at Whole Foods. Let's just buy$4 ,000 of Whole Foods gift cards. And every time we went to Whole Foods for the next year, we were just spending Whole Foods gift cards. And it really messed up our budgeting because we use Copilot to track all of our expenses. And so for like eight months, we had no groceries expenses. Right. Like we had no grocery expense because we were always paying with a gift card. And it's not like you sink your gift cards. So it was like one month we spent four thousand dollars on groceries.

58:30And then for the next five months, we spent zero. So ridiculous because it seems ridiculous, but also ridiculous because it really messed up all of our kind of financial tracking and systems. and I think I basically at the very end, the day we used up the last gift card, I think I went back and just said, well, we bought 4 ,000, it lasted eight months and I just made it 500 a month to try to even it out. But was it worth the effort? I don't know. At that stage in our life, it probably let us take a trip we wouldn't have taken. So I'd say absolutely, but it felt a little ridiculous at the time.

59:02I feel like I'd be the type of person that would just overspend on the gift cards because it's like free money, six months down the line, I'm just kind of utilizing them even way more than I would normally spend. That's hilarious, though. I think that's one for sure that that's awesome. So where do you see people wasting their time when they are looking at redemptions or are they chasing bad redemptions? Do you see people kind of going after, you know, different platforms or things like that where they are just kind of wasting their time? I actually got an email from someone that was a really good example of this.

59:29They'd learned that transferring points to airlines is a great option. They've been doing that for years and they were trying to book a trip for their family somewhere internationally, somewhere in business class. And they emailed me and they're like, the best deal I found is like 3 million points. What do you think? It was some astronomical number of points. And I was like, well, did you even look at the travel portal? And they were like, no. And they went back and they'd gotten so accustomed to booking points by transferring to airlines was such a good deal that they didn't realize that sometimes it's a terrible deal, right?

59:59Like there are times where you'll look at Delta and yeah, Delta can get you where you want to go, but it's like 2 million points for a flight that might only cost$3 ,000, right? Like, and in that case, you'd be way better off buying the flight, earning, you know, a ton of miles. And in this case, it was a business class flight, which usually pays like two times as many miles that you're going to earn flying that flight. So it was just funny that they'd gone so far down the optimization game that they forgot to just check how much would the flight cost. Or they were looking at an isolated thing.

1:00:32So let's say you want to go to Japan from the West Coast and you think, wow, I'm looking at Japan Air and the flight's$10 ,000. So I'm getting such a good deal spending my miles on it. But they didn't consider that Zip Air is another airline that flies actually a subsidiary and it actually flies from San Francisco to Japan. Maybe that flight's$2 ,000 instead of$10 ,000. So it's like you're not comparing apples to apples. You're like, well, this feels like a good deal because the flight was$10 ,000. But if I bought a different flight, it was only$2 ,000. And you can do this at any scale. You could say the flight was a thousand.

1:01:03But if I took this Southwest flight, it's only like three hundred dollars. So I think you've got to do your comparisons, not just with the exact flight you're going to be on, but with a reasonable alternative. And so if you do your comparison and you say, well, the points are totally worth it because it's saving me this five thousand dollar ticket. But I could book another airline and it's eight hundred dollars. So like just book the other airline. And that's a case where maybe you just book that eight hundred dollar flight in the travel portal. I'm not upset with that. Like, I want you to travel.

1:01:30I want you to get out there. But sometimes you can learn how the game works so much and forget that sometimes the game isn't the best thing to play. Or this is my own mistake. Sometimes I love how easy it is to cancel flights. Then I'll book a couple options. So I'm never, you know, my flight gets canceled. I already have a backup. And I talked to someone the other day and I've done this before where they did that and then they forgot to cancel the second flight. You know, like one time I booked this flight on American first class from New York back to San Francisco through British Airways. And I was in New York and it was an evening flight and all the meetings I had that day got canceled.

1:02:06So I was like, I'd rather just go home. So I booked a flight on United and I went to cancel the British Airways flight, not realizing that you can't cancel British Airways awards within 24 hours. I didn't realize this till I was already at Newark and that flight was out of JFK. So at this point, I'm like, it's a lost cause. I just canceled this flight and I lost all the points. So I think you can start to play this game at a level that you're optimizing so much and then realizing the mental overhead to manage everything you're doing is so high. And so even though I know how this game works and I've been able to get really outsized value, when I have friends who just play cash back and they just buy tickets, I'm jealous of the simplicity of it.

1:02:45There's no mental overhead for them. They're like, I have one credit card, I put everything on it. When there's a flight, I just buy the flight and I'm just so jealous of how simple it is for them. But then sometimes I'm like, oh, but you're a sucker. You paid so much and I got such a good deal. So it's like there's a balance there. For sure there is a balance and you can over-optimize and have blinders onto everything else. But at the same time, like you said, there's definitely a balance where you can kind of have the best of both worlds, I think, for sure. One last question. If you had to give people one mindset shift to make their point strategy actually work for them, what would it be?

1:03:18I can only have one. I would say, I'm gonna have a run-on sentence mindset that strategy here. Maybe it's like, I guess it's be honest with yourself. And that's both about the time you spend the flexibility you have, because sometimes it's easy to put on your rose colored glasses and think this game is going to be awesome. We're going to travel around the world for free. But be honest, like, are you actually flexible with the way you travel? If you're not, the game might not work. Are you the kind of person that is going to make this an obsession and a full time job such that you're spending 20 hours a week playing this game to get an extra 20 percent of value that might not be worth it.

1:03:52So I would say, think about everything you're doing and what kind of travel you like, be honest about who you are and what you want. And if you fit the mold of someone who's flexible and really wants to get outsized value, especially premium cabin, business class, first class kind of stuff, you're going to have amazing experience. If you don't care about that and you only fly domestically and you don't care about business class and you aren't very flexible, like be honest that this game might not actually give you any outsized value. And so you got to look at yourself and ask, what do I care about?

1:04:23Do I care about simplicity or do I care about a deal? Do I care about long haul international travel in business class or not? And if the answer is I'm flexible, I enjoy this sport and I want to travel around the world, ideally in like fancy luxury ways, you're going to get so much value. And I don't think it has to be luxury. I think international economy is also a really, really outsized way to get value. But I think domestic travel is harder. Like you can get value on really expensive flights that are really short using points. But for the most part, I think if you're not traveling internationally or you don't want to stay in really nice hotels, it's going to be harder.

1:05:01For sure. I completely agree. Well, this has been awesome, Chris. Thank you so much for coming on here. Where can people find out more about you, your show and everything else? Yeah, I did. Two main things are every week I do a podcast called All the Hacks about optimizing your money, your points in your life. And sometimes it's interviews, sometimes it's deep dives where I'll go through all of an issuer and all their cards and how to think about them and rank them. And then every Saturday, I send a newsletter, you can go to all the hacks.com slash email. And I just share all the top deals points, everything that's happening this week.

1:05:31The nature of a podcast is that it's like it's not news, it's kind of, you know, a deeper dive. And so the newsletter is where I share everything you need to know about now. and then the podcast is where I share kind of the deep dives with guests, with myself doing solo stuff. You can find everything at allthehacks.com. You could search all the hacks. If you're listening to podcasts now, you could just type all the hacks and you'll find it and enjoy and let me know what you think. And both are extremely valuable. I cannot recommend them enough. So thank you so much again for coming on and we'll have you back on here soon.

1:06:00Sounds good. Thanks for having me.

1:06:38We'll see you next time. Availability varies 18+.