Afford Anything - How To Travel For (Almost) Free, with Chris Hutchins

Episode Date: August 24, 2022

#398: Chris Hutchins is an avid life hacker, a financial optimizer and the host of the top ranked podcast “All The Hacks”, where he shares his quest to upgrade his life without having to spend a fortune. These passions have led him to being featured in a documentary on financial Independence called “Playing with FIRE” and collecting millions of points and miles. If you want to learn more about optimizing your spend so that you can travel with less of an impact to your bank account, you’ll want to hear what Chris has to say. Timing of discussion points as per August 2022: 04:13: Is travel hacking a good use of time? 08:15: What is the simple path to optimizing spend? 09:108: Why focus on one rewards program? 10:46: Why are there recommendations for transferable point programs and what are the benefits of co branded cards? 18:08: How can the value of points or miles be estimated? 22:08: Is the best redemption value in booking business class international flights? 32:34: How do you know the best flight to book for optimal redemption? 37:00: What is the difference between airline miles and credit card points? 38:25: What is a “positioning” flight and how do I utilize this strategy? 47:42: What is the process for choosing flights based on reward redemptions? 57:15: What are the best ways to boost an existing points balance? 1:02:12: Discussion on credit cards with crypto rewards… 1:04:17: Tips for those who want deals but don’t want to work with miles or points… For more information, visit the show notes at https://affordanything.com/episode398 Learn more about your ad choices. Visit podcastchoices.com/adchoices

You can afford anything, but not everything. Every choice that you make is a trade-off against something else, and that doesn't just apply to your money. That applies to your time, your focus, your energy, your attention to any limited resource you need to manage. Saying yes to certain opportunities implicitly means turning away others. And that opens up two questions. First, what matters most? Second, how do you align your decision-making around that which matters? most. Answering these two questions is a lifetime practice, and that's what this podcast is

here to explore and facilitate. My name is Paula Pan. I'm the host of the Afford Anything podcast. Today, we speak with Chris Hutchins about a topic that we have never covered in the six years that we have run the Afford Anything podcast. We have never dedicated an entire episode to optimizing credit card rewards, travel rewards, mileage, cash. Some people refer to this as credit card hacking or travel hacking. The financial independence community tends to have a lot of Venn diagram intersection overlap, shall we say, with the travel hacking community. Oftentimes people who are interested in fire are also interested in optimizing their credit card spend so that they can get the most of cashback offers, airline mile offers, airline lounges,

all the bells and whistles, all the special rewards. I've avoided this topic in the past because it seems a little too product-oriented, a little too surface. To use the tree analogy, it has always seemed to me like the leaves rather than the roots. The roots are your values, your priorities, your principles, and also your frameworks, your mental models, thinking about how to think, metacognition. That's the root structure. That's the base of the tree of knowledge. And the leaves, that leaf canopy, that's where products, tools, apps, oh, try this co-branded credit card, no,

try that credit card. That seemed so leaf canopy, so surface, that I've never dedicated an episode to it. And so I told Chris, because Chris is the host of a podcast called All the Hacks, which, as the name implies, it's all about hacking in all its forms, travel hacking, life hacking. And so I told Chris, if we're going to discuss this on the Afford Anything podcast, this needs to be more than merely tactical. This needs to address at a strategic level and at a decision-making level, whether or not such an endeavor is worth our time. And if so, how then do we go about making decisions about the myriad of offers that will come across our path. Because tactics, tips, special offers, these things come and go. But how do we make decisions around them? How do we make

choices? Those are the questions that Chris and I discuss. Now, a little more about Chris, I mentioned, he's the host of a podcast called All the Hacks. He was featured in the Playing with Fire documentary, a documentary about financial independence that many people in the Afford Anything community have seen. prior to starting his podcast, he co-founded two companies, one of which was Grove, a financial planning fintech company that was later acquired by Walthfront, and the other of which was a company called Milk, which was later acquired by Google. He reached financial independence many years ago, but like many FI people, is constantly involved in new projects. Here he is, Chris Hutchins. Hi, Chris. Hey, how you doing? I'm great. And thank you for spending this

time with us, you are known for being the master of hacks, and specifically what I want to chat with you today is travel hacking. Before we get into the who, what, where, when, why of travel hacking, the first question that I want to lead with is for the skeptics who are out there, is travel hacking a good use of time, or is it overcomplicating your life for the sake of what will ultimately amount to a comparable cash value of $5,000, $10,000? I think it really depends on the type of travel you want to do, and the kind of joy you get from deals, right? If you're someone who only buys one or two domestic flights a year, you know, you're not trying to optimize yourself for flying in business class, maybe just getting a 2% cashback card is like the easy path.

But if you want to travel internationally, or if you're trying to get an experience in business class or at a five-star hotel that you otherwise would never pay for, whether it's like at your core. You would never be able to stomach the $5,000 round trip ticket or something. And that thrill is exciting. Then I think it can totally be worth it. And there are services you can pay to have people go through a lot of the arduous work of trying to find availability and book the flights. So when it comes to is it worth your time, you know, usually the most painful part of spending your time on this is like, okay, well, is it available this day or this day on this airline or that airline? You would just pay someone about $200 to go and do all that searching for you. So if you're trying to book a round

trip flight to Europe and it's $5,000 in business and you're going to get it for, let's call it, a thousand dollars worth of points, then yeah, it's probably worth the $200 to pay someone to do it if you don't want to spend your time that way. But I notice in your answer, you talk about, you can pay somebody to essentially be a redemption consultant. So they can help you optimize the way in which you redeem those miles. But before that happens, earning those miles can also be labor intensive. I've certainly gone to conferences where there have been breakout sessions where travel hackers have talked about how they open a certain credit card and then they buy gift cards and they trade in those gift cards for money orders, which they then use to pay off the gift.

And it's this incredibly complicated flowchart of a series of actions. And then they've got their whole spreadsheet of, you know, the next 12 cards that they're going to open with the certain minimum spend that they need to reach on each and precisely when they need to close those cards so that they don't hit that date where the annual fee kicks in. I mean, it feels for the people who are really into this like a second job. Yeah, everyone has something like this in their life, right? If you've met someone who's like obsessed with fantasy football, they're not spending hours and hours and hours every week researching things and tweaking their lineup because they really want to win that, you know, $200 prize at the end of the year. They're doing it because

they enjoy it. So I think taking it to that extreme is not something you need to do to be able to fly and travel for free, but it's something that if you really love it, you might go that deep. But the simple version of just, I'm going to open up one credit card right now that aligns with how I spend money. You spend your money on travel and dining, get a card that focuses on that. You spend your money on groceries, maybe focus on a card there. You don't really spend anywhere specific, get a card that just earns two points per dollar on everything. That kind of simple path of I'm going to open up a card. I'm going to get the sign up bonus and then I'm just going to spend depending on how much money you spend. Maybe you end up racking up, you know, a few hundred

thousand points every few years and taking a vacation for your family every couple years. You want to get extreme and open up five cards a year, 10 cards a year, have the spreadsheets, go buy everything you want through gift cards that you bought at the grocery store through your grocery store card or at the office supply store with your office supply store card, you can do that. I don't think it's an all or nothing game where you have to go that far down the rabbit hole to start to get value. If you're spending money on a debit card, you're just giving money away because assuming you can responsibly pay off your credit card, you otherwise would just be getting at a minimum 2% cash back, if not points that could be worth more than that every time you

buy something with a credit card. For the average person who's listening to this, what is that optimal 80-20. Is it just opening one card? Is it something a little bit more sophisticated than that? If you spend a lot of money in the types of categories that often credit cards give really big bonuses for, that's like travel and dining and that kind of stuff, you know, the 80-20 is to probably get, you know, like a Chase Sapphire preferred or reserve, which is, you know, two or three X on travel and dining and pair it with like a Chase Freedom Unlimited, which is one and a half X on everything else, right? That's like two cards in one platform, like financial institution. You're not trying to keep track of lots of things. One of them has no annual fee. There's that version.

And then if you're not someone who spends a lot of money in the categories that often have bigger bonuses, could just be get one card like the Capital One Venture or Venture X, where you get two points per dollar on everything and you're not really worried. Like I think that's the easiest entry is one or two cards that align with your spending or align with all. spending and focus them on one program. Why focus them on one program? So the challenge is, let's say you were earning points in Amex and in Chase and you're like, ooh, I found this great hotel I want to stay at it. It's a Hyatt Hotel. Well, Amex doesn't

let you transfer points to Hyatt. So now you have like points in one platform and not in the other. So I think if you want to get to the point where you have six figures of points in a program, maybe you can expand. Maybe you could have two. But when you're just getting started, you know, having 20,000 points in one airline and 5,000 points in another and 10,000 in another credit card program, it's not enough to take a vacation in any of them. So until you're like, in one program, I have enough to plan a trip, I feel like it's too soon to start spreading thin. That said, if you're flying on an airline that you don't fly on a lot, definitely open up a mileage account with that airline and earn the miles. Like, I'd rather have 5,000 delta miles

than zero delta miles. But I'm just saying if you're going to start to pick a way to try to increase those points by spending money on a card, don't spread yourself thin until you're sure that you can earn enough in all the programs to make it worth the time. Now, I notice that most people in the travel hacking community tend to say something similar to what you've said in that they recommend cards like Chase Sapphire, Chase Freedom, Capital One Venture, where you can transfer points to a variety of different airlines or hotels. So they are not specific to any one brand of airline carriers. or hotel carrier. Why is that? And what are the pros and cons of branded cards? So, for example,

Delta or American Airlines or Hilton Hotel's branded card, co-branded card. Yeah. I mean, the main reason is that where you're going might not have a Hilton or, you know, where you're going, Delta might not fly to. My wife and I live in the Bay Area. And, you know, we have a bunch of Delta miles and Delta flies to like five cities from here. So, you know, now that we have kids, we're valuing nonstop flights a whole lot more than we used to. It's like it's not that useful to have Delta miles. Now you can use those Delta miles on Air France or you can use them on some of their partners. So it's not like you're tied to the one airline that you have points in.

And if you have Marriott points, you know, Marriott has like 20 different hotel kind of lines that you can use. But if you have a transferable point, you could say, okay, well, the flight I want is actually on British Airways. So I can transfer my Chase Ramex points to British Airways or actually this time it's on Korean Air, so I'll transfer it to something in the Sky Team Network and book there. So it just gives you a little bit more flexibility. The downside to it, though, is for that particular brand that the card would have otherwise been associated with, when you have their card, you're usually getting more than just

points. You know, United Card might give you checked bags for free. I think the highest Delta card lets you into their Sky Clubs, or even some cases, lets you earn the types of miles that give you status on the airline so you can get upgrades. You know, some of the hotel cards, you might get 10 points per dollar at the hotel, you know, when you're using their card and giving them your, you know, status program number. So you can earn points a lot faster with those programs. But it's not always true. I find it kind of strange that, you know, one of the United cards earns you two United points per dollar when you spend on it.

And then the Chase Sapphire Preferred or Reserve earned three Chase points that you could transfer one to one to United. So you actually earn more United points per dollar using. the Chase Reserve card, then you do using the United card buying a United ticket. But what you're not going to do is you're not going to get a free check bag. You're not going to get access to the lounge. You might not get priority boarding or whatever perks come with that United card. So if there is an airline or a hotel chain that you're rather loyal to, and I'll get to why hotels are a little different and maybe even more important in a second, then it could be worth having that card. You just have to weigh the pros and cons. Do I spend enough or fly enough on that airline that it's worth

having another card paying that annual fee if there is one to get those benefits. Because if you fly United once a year and the check bags, you know, are going to cost you $50 and you've got to pay $100 every single year. Right. You know, maybe it's not worth it. Hotels, one of the interesting things is there's a lot of blogs online that'll say, this is how much United points worth. This is how much a chase points worth. They do these valuations. The points guy has kind of started doing this, at least other blogs I'm sure have. And they have all of them. The flexible points are usually worth a little bit more because you just have more option value of how you use them. But most hotel chains, the points are worth less. Not because the program is worth less, but if a hotel you can earn

10 points per dollar, the points are just, you have more of them. So a lot of the hotel chains, points are worth less than a cent. And then a lot of the airline programs, they're worth more than a cent. And a lot of the flexible currencies, Chase Ultimate Rewards, Amex points, you transfer generally one to one. And so the reason why you could be a little bit more loyal to a hotel chain, maybe get a co-branded hotel card, is just that you usually don't get a great deal transferring your Amex, your chase, your built card points to hotels because you get one Hilton point for every Amex point. You get one Marriott point for every chase point. But those Marriott points are worth, you know, on average, about half of what an airline mile is. So you're getting a

much worse value. The notable exception is Hyatt. So if you have a built rewards card or you have a chase card, Hyatt actually is a, the currency is just worth more. That's not to say the program is. It just means that each single point is worth more. A hotel might cost 30 or $40,000 for a top tier with a Hyatt, but at Marriott or Hilton, it might cost 80 or $100,000 points a night, which just means you need more of them. So if you don't have a card that transfers to Hyatt, you're probably not going to be earning free hotel stays as easily as you would if you were, you know, dedicated to earning points on a hotel card. But another option there is just use your points for flights and just buy your hotels with dollars. The fun part about the Chase program and Capital One

a little bit also is that you don't have to go all in on committing to go down this rabbit hole, right? You can get a Chase Sapphire preferred or reserve card. You can earn all these points. And then you can later decide, I just want to use the points to book flights and hotels. I don't want to deal with transferring. I'm going to log into Chase's travel portal, and I'm going to get, depending on the program and the card, one to one and a half cents per point. So if you've got a card that's earning two points per dollar and you can get one cent, then like your fallback is that you've got the value of a two percent cashback card. With the exception, you have to use the cashback to book travel. But if you're spending $100,000 over the course of this card and you're earning two percent

back, you're earning $2,000. So you have to spend $2,000 on travel, which I imagine for most people that spend $100,000, like, they probably are going to spend $2,000 on travel eventually. And so I think the fallback of it is you always have the value of these points as cash. You just have the opportunity if you want to transfer them to airlines or hotels to get even more value, but you don't have to. You know, there are tools out there that make it easier to search for availability and get, you know, inventory and hotels and flights. But if you don't want to do that, you can just go book any flight or any hotel and get one to one and a half sense for those points. I think you usually, even doing that, come out ahead over using a cashback card.

Is a little bit more work? Yes. But the option value of, oh, I decided I want to transfer my points and get a lot more outsized value, it's there. If not, you don't need to do it. Right. So thinking through the math of what you just said, so if it's a card where you get two points per dollar, per dollar that you spend, and you then redeem that at a value of one and a half cents per point, then essentially you're getting the equivalent of about three cents for every dollar you spend 3%, which would then put it ahead of most cashback cards because I've never seen a cashback card that pays more than 2% back. Yeah, so Chase Reserve is a pretty common like travel card.

You get three points on travel and dining. The Chase Reserve is one of the only cards that makes those points worth one and a half cents. So there, all your travel and dining spend is worth $4.5.5 cents because one and a half times three, four and a half percent back on travel and dining is pretty good. The cool thing about Chase is if you have any of their other cards with one of the cards that gives you more value, you can move them around. So if you get the freedom unlimited, which is one and a half percent back on everything, you can use those at one and a half cents per point, and you actually get 2.25% cash back on everything. So that's why I think it's a great combo. It's like,

if you want to think just cashback, you're getting four and a half percent on travel and dining and 2.25 on everything else. That's better than a 2% cashback card. And that's without playing the miles and points transferring booking game at all. That's just use those points to go say, I want this flight on this date. I don't care if there's award space. I just want to book it. Given the variation in redemption, so we started this conversation by talking about how in the world of travel hacking,

there are basically two giant actions that a person takes. A person is either earning and accumulating points and miles, or they are redeeming points and miles. And there are different strategies, tactics, and techniques for each of those two actions. given the variation in efficacy of redemption, right? The fact that you could have two individuals who person A is very efficient at optimizing their redemption and person B is not, how can you estimate overall the value of a point or a mile? So the way most people do it is they'll say, okay, how much is Chase point worth? And they'll say, well, Chase can transfer to all these partners.

So let's first go see what are all these partners worth. So then it's like, okay, how much is a united point worth? They're like, okay, well, this is easy. Let's go price out what it would cost to book. I think the points guy, when they recently started redoing their process, they priced out hundreds of flights across different time horizons and say, okay, well, this flight would have cost me $300 to book and it cost this many points. And this flight would have been $1,200 and it cost this many points.

They go through all of these options to just kind of say, okay, well, this is the value of a united point. And if you do that across every program, and this is not something I expect anyone listening to do, but there are websites out there that do this, search valuation of points, then they say, okay, well, if you look at all the programs out there that you could transfer a chase point to, you know, they range from a point being worth 0.5 cents all the way to 1.7 cents. And then this is where you kind of do some fun math and you're like, okay, well, obviously if I can go to all of them, it has to be more valuable than just having the one that's worth 1.7 cents. And then this is where you kind of do some fun math and you're like, okay, well, obviously, obviously if I can go to all of them, it has to be more valuable than just having the one that's worth 1. So let's round up and call it 1.9. That last little bit of math, I don't think there's like a perfect answer for how you do that, but, you know, the flexibility is worth something. That's, I think, how they figure out what it's worth. Are there circumstances where people are willing, are able to get much more outsized value? Yes.

In the best case scenario, I once got 10 cents per point. What? All right. I'm going to ask you about that later. And that's not normal, right? you know, a really good redemption in my mind is really anything over, let's call it, two cents, because you can get one and a half. And most of the outsized redemptions, if not almost all of them, come from booking flights that otherwise would be really, really expensive, which are usually

international business class flights, and occasionally flights between small airports that are really expensive to fly to. But for the most part, it's this kind of weird thing that still continues to be true is that flying business class internationally costs anywhere from three to ten times as much as a coach flight. And for many airlines booking a business class flight with points costs two to three times as many points. And so if you double the points, but you'd have to five X the price, the points are worth more when you're booking business class. Now, I'll play the counter to myself, which is to say, is it really worth the cost of that business class flight if you never would have taken the business class flight

in the first place, right? If you were only going to fly coach, then you can't really say you got 10 cents per mile unless you were actually going to buy the business class flight. And that's where I'm like, yes, you're right, but I don't have a better way to say, what's a business class flight worth? What would I have paid for it?

I could go through some kind of math of like, oh, I'd pay 20% more, 30%. I don't know. I've never actually paid for an international business class flight with dollars. But that's where the kind of fun of it, it is. I'm not saying I got that much value and that's how you should think about it and savings and value your time. I feel pretty good that I got this $10,000 flight for our honeymoon and I only

paid $120,000 points for it. In a while, I'm going to ask you to go into the story of how you were able to do that. But backing up a little bit and talking conceptually about what you just said, I guess two questions. Number one, would it then be accurate to state generally that the best value redemption is business class international flights. And B, if that is the case, is it better to book it as a business class ticket right away or to book it as a coach ticket and then use your points to upgrade? Is there a distinction in terms of redemption? I would say that business class is like the best, but like international economy can be very, very good. I don't want to scare people off thinking, well, the only way to get your value out of your miles is to have enough to do the, you know,

$150,000 business class flight. I've seen some incredible economy redemptions. I think if you transfer your points to Turkish airlines and you want to fly from anywhere in the U.S. to Hawaii, I think it's like 7,500 points, like less than 10,000, which can be a really expensive economy flight and can be a really good deal. But I think, you know, the nature of business class flights being astronomically expensive, like $10,000 can sometimes make the miles such a better redemption value. But if you want to fly economy halfway around the world, you can get some really good deals. On the upgrade front, most of the programs these days, I'm sure someone listening will know more about this than me and point out the edge case. But in many cases, to use your miles to upgrade,

you often have to book like a full fair economy ticket or a really, it's not just like the cheapest tickets out there. And so I can't think of a single time in the last five years. And I've looked that buying the coach ticket and upgrading with miles was a better deal. Many airlines don't even kind of display the inventory for upgrades available online. A lot of them don't clear until you're at the gate. So do I think maybe there's a chance that if you're willing to risk that it won't clear and you'll just like at the gate find out if you got upgraded, could it maybe have been a better deal? Yes.

But if you want to confirm it in advance, I don't know of a lot of circumstances. And in fact, I can't think of one I've ever found in the last five or six years. where booking the economy ticket and upgrading it with points was a better deal than booking it with points in business. What about booking the economy ticket with points and then upgrading it with cash? Could that be the cheaper way to get that if you were to use that hybrid? I'm not even aware of any airline that would let you do that. I don't know of an airline that lets you upgrade your award tickets. So I don't think that would be an option.

I'm sure there are a few that maybe like, you know, as you're nearing the flight, you could say, hey, can I upgrade this? Hotels will let you do it. Hotels will let you book a regular room and then call and say, hey, I booked a, and this is often done, the most common in the points world, it's like, I booked a room at one of these hotels around the world with overwater bungalows, but like you can't usually book the overwater bungalows with points. So people will book the just beach room and then they'll call and say, hey, can I upgrade with dollars? That is more common in the hotel world of booking a room and trying to call and upgrade it with dollars. But in the airline world, I'm not familiar with any cases where that works.

So then tell us about when you got 10 cents per mile or per point. How did that happen? Yeah, I mean, this was our honeymoon. And so it was one of those times where you have like a year to plan and you're going on something, you know, exotic. And really, your dates are kind of flexible. Some people want to go on their honeymoon the day after they get married. But we were like, okay, we have 18 months to plan.

We decided we wanted to go to the Seychelles, which we'd never even heard of. but I think Prince William had just gotten married and gone there on their honeymoon. And so when you Googled, you know, when we were searching like honeymoon destinations, everyone was like, this is just dreamy. It's amazing. We were like, well, you know, if you're going to fly halfway around the world, a honeymoon seems to be a good excuse. And so we knew in advance that we were going to do this flight. We knew that the best way to book it at the time was using Delta miles on Air France. And so we just were searching. We had alerts set up with a, you know, a subscription site that I pay for that's like, when does everything open up? And we were just set

alerts for all these dates. And as soon as it opened up, we booked it. And I want to say, I could probably go back and look at notes, but I want to say it was 120,000 points per person. So we spent about 240,000 points. And we ended up booking flights that were, I think, somewhere around $11,000. So it might have technically been, you know, a little bit less than that. You know, so it was $22,000 for 240,000 point. It might have been, you know, nine and a half cents per point. But it was definitely a lot. And if you figure, I'm not saying this is repeatable or easy, and I don't think it's ever happened to me again. But I do get a lot of fun satisfaction thinking, wow, if I have a card that gives me three points per dollar and I can get nine cents, that's like getting 27% back on a card.

27% off is amazing. But I would call that you're like once in a lifetime redemption. And maybe for a lot of people's honeymoon, they will spend the $22,000. We did not have the money to spend $22,000 on our play. So if we didn't have points, we would have been flying coaching. somewhere, and probably not to the Seychelles, but that was it. And to just add like one more exciting bit to that story, we had seen a friend of ours's wedding video. And when we were planning our wedding, our budget was nowhere near what many people's budgets were. But I had no idea how much

it cost to hire a videographer. And so I had seen this video that a friend of mine who I knew had a lot of money had done. And, you know, some things, flowers, it doesn't matter how much money you have. Like the flowers, you buy more flowers, but people don't mark. up flowers for rich people. Maybe they do somewhere. So we called this videographer that made his video and we're like, your video was amazing. We would love to talk about doing our wedding. We talked to them and we get so excited. Then they sent us this proposal and it was something like $12,000 to do our wedding. And I was like, so we can't afford that. So this is not an option. And she was like, oh, I'm so sorry. And we built a relationship with this woman because we met her and

we were talking about things. And I don't know. We were just. just talking. This is back almost 10 years ago. We were talking on G-Talk or whatever Google chat was at one point in time. We were just casually talking. She's like, how's the planning going? I was like, we just booked our honeymoon to the Seychelles. She was like, oh, my gosh, my husband and I have dreamed of going to the Seychelles. I was like, really? She was like, we would do anything to go on that trip. It would be amazing. And I just said, well, we booked ours with points. What if we booked yours with points? I was like, could we trade? What if we sent you to the Seychelles, not on our honeymoon? You're not coming with us. But what if we booked flights for you guys?

and she was like, I would probably just do the wedding for free. And so we ended up, there was this promotion at the time, which is why I proposed it, where Delta was like, if you transfer points to a friend, which you have to pay for it, which is not cheap, but they would double them. And so we had just transferred all these points to my account to book this honeymoon. We had like found the tickets, but we hadn't booked it yet. I was like, this is what we're doing. And I ended up saying, okay, I looked at it.

It was like $2,000 to transfer all the points to my wife. So I was about to book our honeymoon and I just transferred them to my wife, paid $2,000. And then we booked our honeymoon like the next day out of her account instead of mine. But we had 240 extra thousand points sitting around because Delta had a promo where they doubled them. And so then we said, great, let us know when you want to go. And so instead of $12,000, we got our wedding videographer for about $2,000 in point transfer fees. So that was like, I didn't factor that into the 10 cents. But if you throw that in there, I feel like it was a really good deal.

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You mentioned the foundation of all of this was that you knew that the best way to fly to the Seychelles and to redeem your points for it was by booking Delta through Air France. How did you know that? So this is like a good thing and a bad thing for the points world in the last decade since that happened. So the bad thing is airlines used to make it really easy. On their website, they would say, here is our chart. You want to fly from the United States to Africa or to the Middle East or anywhere in Coach. It costs this many miles. Really simple.

Some airlines still have these. I think American Airlines had a chart like that or something. Or maybe it was United. And they had two different classes. it was like the saver class and then the standard class. So United always had this saver and standard. It was so easy. You knew exactly what you were going to look for.

You knew what it was going to cost. In the last 10 years, a lot, if not almost all, not all, airlines have kind of changed. And now they're kind of dynamically priced. And there's no chart. If you search for a United Award chart, I don't think you can find one anymore. Some airlines have them. Air Canada still has one. But a lot of them are gone.

So the downside is it used to be really easy. You'd say, okay, if I want to go from here to there, the limited. is two things. What airline flies there? So it's like, okay, there's five airlines that fly here. Then you could go look at all the websites of the airlines that fly there and their partners and say who has the cheapest. So that's the downside is that those don't exist. The upside is there's now 20 or 30 or 40 or probably thousands of blogs about this. If you go online right now and say best Miles Redemption to go to the Maldives, I bet there are seven blog posts at least where someone who is as much of a nerd or more than I am,

has gone in and outlined here with chase points or amex points is the best way to get to the Maldives. So we've lost a little bit of the ability for you to just directly do the research yourself because these charts are not there anymore. But what we've gained is a community of people that are passionate about sharing information and write blog posts and videos walking you through how to do it

and what exactly you need to do. And tools like there's a site called point. point. Me. If you go to point. me, it's like an award searching engine. It's not free, but you know, you can go and say I'm going from New York to Rome and on these dates and they'll

say, okay, well, here's this flight. It's this many miles, but it's this many if you book it by transferring Amex to Delta and it's this many if you book directly with Delta points. It's this many if you transfer it to Air France first. And so we've gotten

better tools and we've gotten better content but we've lost the simplicity of here's a chart of exactly how much every flight from region A to region B costs. Basically, they made the process less transparent. And as a result, a crop of entrepreneurs sprung up to plug that inefficiency. Yeah. And that entrepreneurship has taken the shape of companies that build software and just websites that write information and content creation.

And I think sometimes we forget that content creation can be entrepreneurship, what we're doing right here. We both have podcasts, and in many ways, that's a similar type of entrepreneurship. It's just different. Right, exactly. I often think that there's a thin line between content and software, thinner than one might think. I don't think I've thought about that, but I spent the last, I don't know, 10 years of my life building software, and I think the way I approach creating a podcast, writing a newsletter is like a business, right?

I'm looking for sponsors just like companies are looking for customers. I'm looking to make good content just like businesses are looking to improve their software, improve their services. So you could look at it as I'm just writing and talking, but I'm doing it for an audience that I want to come back. I want to deliver the best content I can. So a lot of the same skills I use starting companies in the past are skills I'm using running a podcast and a newsletter, which are companies, right?

It's an LLC. It is a business. Right. Exactly. At some future point in time, I want to bring you back on the show to talk about the companies that you've started because you've done unique things that many people in our community, especially in the financial independence, fire community have not done. So we'll put a pin in that and come back to that on a different episode. But for now, to stay on the topic of miles and points, I suppose I should have asked you this at the beginning. What is the distinction between airline miles versus credit cards? points or reward points, and how can a person decide which of the two they should prioritize accumulating? I think in general, the words miles and points to me are virtually interchangeable. Some airlines actually accrue points. So I think rapid rewards for Southwest is just rapid reward points. That's right. And Capital One calls their points Capital One miles. So they're somewhat interchangeable. The way I would think about it at the highest level is if you always fly one airline or if you always stay in one hotel chain, you might do better just going deep on them

for your kind of primary earning. But if you spend a lot of money on dining or broad travel or even groceries, there are credit cards that will really maximize that. So I generally think transferable points is the way to go. Maybe if you're all in on Delta, pick Amex because you can transfer your Amex points to Delta. Or if you're Chase,

you can transfer your chase points to United. Sorry, if you're United, you can transfer your chase points tonighted. If you're American, you can get built rewards and transfer your points to American. So you can kind of play both and kind of hedge and say, I'm really loyal to this airline or this hotel chain. But for all my spend that's not on those brands, I'm going to get a card that at least partners so that I have one place that I can pull up a large number of points. So by the time this episode airs, I will have already gone to Greece. But as of right now, I have not yet booked that ticket.

In fact, I'm planning on booking that ticket probably tomorrow. I have a bunch of miles on a bunch of different airlines. What should I do? Yeah, so Greece is a great country, both to travel to. My wife and I went last year, and it was incredible. So, one, awesome, have so much fun. Two, it's a great case study because there's something that Scott Kyes, who started this company, Scott's Cheap Flights, who runs a newsletter, and he recently wrote a book.

he points out this thing that he coined the Greek island trick. So I'll get into all of this. At the highest level, I think something to think about, and this is true whether you're spending money on flights or whether you're using miles, there are some countries where lots of airlines fly to that country. If you're going to Paris, you know, this isn't as relevant. But if you're going to Mallorca, an island in Spain, if you're going to Greece and you want to fly to Santorini or Crete or Mekonos, a lot of times we all go online and we search, I'm going to go from New York, JFK, to Santorini. And you're like, wow, these flights are really expensive.

Or I'm looking with miles and it's like, wow, there's nothing there. The problem with that search is that there aren't a lot of airlines that both cross the Atlantic Ocean and fly to Santorini. And that search is almost always only going to show you airlines that do both. And so the biggest hack here, which works for paid flights and miles flights, is to do what's called a positioning flight, which is like, I'm going to position myself somewhere where I'm really easily can get to where I want to go. So let's take Santorini as an example. Let's say you're going to Santorini in Greece. I would say, first thing, go to Google flights and search from

Santorini, leave the two empty. And it doesn't matter what date you put and search, maybe a Saturday, because there's most of the flight options that exist are going to be on a Saturday, and then switch the filter to nonstop. And you'll see, here are all the places that if I can get to, I can quickly get to Santorini. I know you can get there from Athens, but you can likely get there from a handful of other cities in Europe. I'm sure there's a Santorini flight from like Barcelona or Rome or maybe Paris and that kind of stuff. And now you're like, okay, well, I don't actually need to get to Santorini with my ticket from JFK. And a lot of those airlines, by the way, that are going to fly to Santorini might be small airlines. Like Olympic Airlines

is an airline in Greece that might fly there, easy jet, Ryanair, some of these kind of discounted European Airlines, they don't fly across the Atlantic Ocean. So they're never going to show up from JFK. So I would say, once you've realized, assuming you don't want to change planes more than once, you realize I want to get to Santorini, I would search New York. And then you can actually on Google flights put a bunch of destinations. You could say New York to Barcelona or Athens, or Milan, or Rome, or Paris. And I think you can put seven or eight in there. And you can from New York, you can put Newark and JFK. You know, if this is a really big expensive trip, let's say you've got a family of five people and you're flying to Europe and you know it's going to be expensive,

I would maybe put Philly. Like a friend of mine was actually doing this. She was in Baltimore and she was looking Baltimore and D.C. And then Philly actually saved on a family of four, save $350 per ticket. So she saved $1,400 by driving an extra 40 minutes to get to the airport. Totally worth it for her. And then you just find, okay, now I've found flights to Barcelona and I could just buy the ticket from Barcelona to Santorini or whatever other city you.

want to fly to Santa Rini from. And it could be, in this case, Turkey. You know, you could fly to Istanbul. Scott called it the Greek island trick because the Greek islands are one of the, like, most notorious places where the airlines that fly to the most of the islands are not the airlines that cross the ocean. And the same thing is true with points. So you've got points in all these different carriers.

I would be out there searching, okay, what are the four or five cities? And you're like, okay, I want to go to this city or this city or this city. And one option, if you've got points on the airlines where it's a little bit easier to search. If you've got American points, you're not going to transfer them to another airline. So go to Americans' website and search, I'm going from New York to whatever the place that connects to where you're going is. And this also works, you know, if you're flying to an airport like Athens, even if that's where you're ultimately just trying to go. You're not actually going to an island. you'd be probably okay if you flew to Rome and had to buy a $75 short flight.

So I typically look at the major cities that are near where I'm going just to see if it's significantly cheaper to fly there or if the points are significantly less. And I've definitely, when we went to Greece, it was like, if you want to get to Santorini, it was like hundreds of thousands of points because it was like one airline that flew there. But if you wanted to get to Athens, it was like 75. thousand points to get there. So it was like, you know, less than half, I remember when we looked, if you went to Athens. And the flight from Athens to, the island we were going to was like $39. Yeah. So that's one. And if you have points at Chase or Amex or something like that,

I think point.comee is the best site to do this. It is not free, but it's not that expensive. They have like short plan. You said you want to book this in a few days, right? I think point at me starts at $5 for a 24-hour pass or $12 a month. So you could try it for a month. You could try it for a day and see how that goes. Explain the logic of taking a positioning flight if you are going to a more populated city. So let's say, for example, that you're flying to Athens or for anyone who's listening to this, let's say that they're flying to a city internationally that is relatively, you know, it's a major capital. It has a lot of different airlines going there. And it's not sparsely flown to.

Yeah. Why would a person take a positioning flight in that case? So let's say you're trying to go to Paris. Maybe one of the easiest in terms of number of airlines that fly to a city in Europe. So you want to go to Paris. For reasons that are far beyond me, it is very possible that an airline like KLM, which is based in Amsterdam, might have really cheap award availability from New York to Amsterdam and no free tickets from Amsterdam to Paris.

Like that for some reason, I don't know why it happens, but sometimes it happens. So what they're going to do is they're going to look and say, oh, well, we can get you to Amsterdam, but we can't get you to Paris, so we're not going to show it to you. Or we don't have any flights to Paris that are cheap. So we're going to have to make this a premium award and it's going to cost twice as much, and we're going to apply that to the whole trip. So occasionally things like that happen, or maybe as an example, there's an area that line that doesn't fly both those legs and they're not partners. So in the case of Paris, I think it's

reasonably likely that if you're flying, you know, tap to Portugal, there's probably they also fly on to Paris. But you wouldn't take a positioning flight if you really want a nonstop flight. I would always start my search with, I'm going to Paris. But instead of searching, I'm going to Paris and I'll take non-stops or one stops, which I could do, I would also at least look at I'm going to Paris or I'd be willing to fly to Brussels or to Amsterdam or something like that. It's not always going to save you money. There can be, if you're checking bags and you don't have a long enough layover, they're not going to necessarily transfer your bags for you.

So you're going to have to get them and you're going to have to recheck them. So I wouldn't say it's like a perfect solution for a heavily populated city. But there are cases where, especially with points, somehow it's cheaper to fly. to, I think another great example, we're going to Tokyo. This is actually a perfect example. I was looking at flights to Tokyo in October this year. And for some reason, there is availability to get to Osaka, but I couldn't find cheap availability to get to Tokyo.

Even though the airlines that fly from San Francisco to Osaka, or in this case, maybe L.A. to Osaka would also fly to Tokyo. It was only cheap to get to Osaka. That was it. And so we knew we were thinking of going to Osaka at some point during the trip. We're like, maybe we'll just start there because we wanted to get there at some point. But in my mind, originally, I was only looking at flying to Tokyo. And so I love this site, flight connections.com.

When you go to flight connections, you can put in any city. And it just shows you all the places that you can fly to from that city. The other place I do this is Wikipedia. If you go to the Wikipedia page for any airport, they usually list all the airlines and all the destinations. I didn't realize that you can fly to Osaka from San Francisco or we were actually thinking of maybe stopping in Hawaii on the way. And there's actually a lot more flights from Hawaii to other places in Japan. So we're like, oh, if we stop in Japan. And actually, now that I'm thinking about this, I think that was from Hawaii to Osaka.

I don't know if you can actually fly to Osaka from L.A. But the same thing still applies that, you know, there was a city that we could fly to, I think, from Hawaii that was much cheaper and more available than Tokyo. but it wasn't showing up for Tokyo. Once you've identified the places that fly nonstop to your preferred destination, how do you then see what that award redemption is? Do you, particularly if you're searching multiple networks, do you have to manually go to each one, the American Airline Network, the United Network,

United is called Star Alliance, American is called, what, One World? Yeah, do you have to manually go to each one? So this is what Point. dot me is trying to solve and they don't work for every airline. But I think they have 33 airlines and they know which points can transfer where. But yeah, sometimes I would just say, okay, I'm going to pull up United's website and I'm going to search from San Francisco to Paris. Okay, now I'm going to pull up Delta's website and I'm going to search San Francisco to Paris. Now, fortunately, if you search online right now and you say best site to search Star Alliance Award availability, you might find that, oh,

maybe Air Canada is the best place to search for all the airlines. That doesn't mean you have to book with Air Canada miles, but Air Canada might have access to some of the partners that you can't book from the United website. There are still some airlines that you can book with United Miles or you can book with American miles, but you can't actually see the inventory to book online. So you might have to go to that airline's website to search and then call American and say, I want to book on this partner. That's where I said, the easy way is I have a bunch of points in airline. I'm just going to check this one. Maybe I'm going to check two. Then the next step is, okay, I'm willing to pay $5 or $12 a month to go search on an aggregator site. And then the next step

is I'm just going to offload this whole project. Point.combe also has a concierge, right? It's $200 a passenger. And they charge a $25 deposit to search. And there are a lot of award booking services that aren't point dot me. And you could just say, I want to go to Greece. I have points in these programs. here's $25. If you find something, they charge you another 175, so $200 total to help you book the flight. And they'll go and they'll search all the airlines' websites.

They have all the tools. They pay for the subscriptions to all the other searching tools, and they'll just go find it for you. Depending on how much your time is worth, depending on the type of ticket you're trying to book. If you're trying to save $100 on a coach ticket off season, it's not worth it to pay someone $200. If you're really eyeing a $10,000 business class itinerary,

like it might be worth it to save $200. So I typically look at the airlines I'm most familiar with, which for me is like the United website, the American website, and see what happens. And 50, 60% of the time I find what I need there. Then the other half of the time I'm looking at point. And I find something that's like transfer to Air Canada from Amex. Great.

One time I've been like, I'm not flexible enough. And I want someone to go do some real searching and, you know, it just saved me time. The other thing I'll say, which, we haven't talked about is all of the availability for many airlines becomes much easier last minute. Many people, especially myself now that we have children, are maybe not as comfortable with this tactic. But if you're listening to this and you're comfortable with it, my wife and I sometimes would say, we're taking this week off to go on vacation. But we don't know where we're going.

And like a week before, or in some cases like four or five days before, we would just start searching, and things open up like crazy in terms of the number of points you need to go somewhere. So if you're flexible and you book within a week or two, you can sometimes get really, really great deals with points. And depending on the airline, one of the positive things, maybe one of the only few positive things to come out of the pandemic is a lot of airlines getting rid of their cancellation fees. So if you book a flight, and this is very true for rental cars, by the way, I'll come back to that. But if you book a flight and it costs 100,000 points for two people to go to Europe, which is actually pretty good. so maybe you're not going to get better than that. But if you book a flight and a week before, you search and it now costs half as many miles,

you can always just book that and then cancel the original one. So I would say, you know, take a look a week before if something opens up. There have been times where we booked something where it was a low number of miles, but we had to change planes one or two times. And then at the airport, I remember one time we went to the airport like three or four hours early. And at the airport, I just looked. And there was a nonstop flight that had availability.

And so called up United, switch the flight. flight, we hadn't checked in yet. That's an important part. Canceled the first ticket, went on the new ticket, and then we just went to a, you know, a different gate to take a different flight, and we went direct. So if you don't find anything great for your flight to Greece and you end up booking with dollars, you could always look the day before, a couple days before. And if your tickets were fundable or you can get credit for it that you think you'd actually use, might be worth looking. Right. But with cancellation policies, will they refund points or miles that have been redeemed? So depending on the airline, some airlines charge like a $100 award

re-deposit fee, and some airlines don't. So some airlines, you know, you could book a flight with miles and cancel it any time. Some maybe it might have to be more than 14 days. It depends on the rules. Every airline is different. But there are airlines where you can cancel and get almost all of them can get your miles back. It's just a matter of whether they have a fee to do that cancellation that you'd have to pay to get your miles back. And after the pandemic, at least a handful of them waived those fees. And what I mentioned on rental cars is also true. Rental cars usually, nowadays, you get this option where it's like, I'm a rent a car and it's like, do you want to prepay or not? And if it's a huge savings and you know you're going on the trip, maybe you prepay. But if not, there is zero cost to

cancel. So I always book a rental car and then, you know, for six months out, every couple months when I'm thinking about it, maybe I set a calendar reminder. I'll look. Prices go down. Rebook the new one. Cancel the old one. They're one of the last holdouts in this. this requirement to prepay and have all these fees. So take advantage of the fact that you can cancel a rental car anytime you want. And if there's something cheaper, rebook it. We'll return to the show in just a moment. In the conversation that we've been having, as we've talked about redemption,

we are assuming that a person has adequate miles that they can redeem. What advice do you have for anyone who's listening to this who wants to boost their points balance or their miles balance? What are some of the best ways to do that? So shifting the conversation away from redemption and onto earning and accumulation. I mean, one of the most common things people talk about is opening up new cards that have big sign-up bonuses. And I don't want to go too deep there because it starts to go down this rabbit hole of, I'm going to open up a card and then open up another card. And it can get addicting because there are cards that earn 75,000 all the way to 100,000 points.

So that can be a big boost. But for people who aren't interested in opening up cards nonstop, because I think that can be, a taxing toll on life. And it has a little impact on your credit score, but maybe not as bad as most think. One that's kind of an easy one is if people are familiar with sites like Racketon, where you can go online, find a retailer and get some cash back, most airlines and points programs like Chase Ultimate Rewards, they have a portal where you can go and shop online and earn points. So we're doing a home renovation.

We had to buy a lot of stuff at Lowe's. So I just went to the Chase website. I went to the Chase Shopping portal. clicked the link to Lowe's, went and bought all this stuff on the Lowe's website, and got an extra point per dollar beyond all the points I would get on the credit card that I used to spend. I actually went a little bit one step further. This is an example of what happens when you do go down that rabbit hole. I wanted to buy, I was actually buying a Japanese toilet from built-in bidet toilet from Lowe's.

First off, I found this site called Save Letterenddeals.com, where they sell Lowe's Home Depot and crate and barrel coupons online. So like the ones you get when you're moving and changing your address or sometimes the Home Depot ones you get from like taking Home Depot webinars. So for $3, I bought a Lowe's 10% off coupon, which is well worth the $3. And then I clicked through the Lowe's website from the Chase site so I could get my chase points. And then I was like, okay, well, the remainder balance, I went to Amazon and I bought Lowe's electronic gift cards from Amazon. And I paid for them. Normally, I would just pay for them. I have an Amazon visa that gets 5% off on Amazon, but this quarter, Q2 2022, the Chase Freedom card, which is a no annual fee card, was doing

five points per dollar on Amazon. So I bought my Lowe's gift cards on Amazon. They show up two or three minutes later, went to the Lowe site checked out. And instead of paying, you know, whatever I was going to pay, I got a 10% discount. I earned five points per dollar plus a six point per dollar in the Chase Portal. So, you know, depending on how you value those points, that maybe is like another 10% off. So it's like 20% off this thing that I was going to buy. Obviously, the easy version is go to the shopping portal. And you can even go to a site like Cashback Monitor, which you type in any retailer, and they say, here's what it would be in the Chase Portal, in the Amex portal, in the American Airlines portal, anything like that. And they compare that to the cashback rates and everything.

So it's a comparative tool. It's a comparative tool that helps you find the best place to get cashback when shopping online. I like that. I like searching around to see if you can find promo codes, but I find that game is harder and harder. So sometimes I just look for, I did like a Craigslist search for Home Depot coupons and, you know, found it. So you could sometimes buy these coupons online. I'm sure the retailers don't like that, but I'm not the retailer. And then sometimes this is a fun hack. If I'm on a website trying to check out and there's live chat in the bottom, sometimes I just reach out to the live chat. I say, hey, I'm about to buy this thing. I'm really excited. it's a little bit over my budget right now. Are there any deals right now? Are there any coupons?

Like 50% of the time, someone's like, here's a coupon for an extra 10% off. Or one time someone said, no, but if you can find a friend that can refer you, you know, referrals get an extra $50 off a purchase or something. And then I just went to Twitter and I searched like referral retailer name. And then I just found someone who had inevitably posted on Twitter their referral link. And then I just clicked through it and got $50 off there. So, you know, I feel like you can go down the rabbit hole a lot of this stuff. I try to, when I write my newsletter, I'm like, here are the, like, most relevant examples. I'm not going to give you every crazy deal and on the podcast.

I try not to go too deep on everything, but I don't know. I think everyone feels you get more than $20 of joy by saving $20 that you otherwise wouldn't have gotten. Right. You know, like, I think there's something there that's like this magical thing, which is probably why I started, you know, talking about this more. is like it just feels really good when you get a price that's lower. You got something better than you were originally going to pay. Like that's satisfaction to me. I'm not paying for it.

I'm actually getting it for free. I'm spending my time. But I really enjoy it. It makes me happy. Right. The little dopamine rush of the win. Yes. I love it.

Yeah. Absolutely. There are now cards that have just started to hit the market that give crypto rewards. What are your thoughts on those? At the end of the day, I think the choice. the challenge with that kind of product is that depending on how you're thinking about crypto, but if it's an investment, it's like, I like to think about investing separate from spending, right?

Like just because I need to do a home renovation now doesn't mean now's the time I want to invest. So that's one thought there. And the other is just comparing the rates, right? Like, am I going to earn 3% back in crypto or am I going to earn 1% back? And I, you know, I'd rather earn 2% if a card were going to give me 1% back in crypto rewards and I wanted crypto, I'd rather just get a 2% cashback card and just buy the crypto. So to me, it's just another way to channel your rewards. And I know the argument, right?

If you had been using a card for the last 10 years buying Bitcoin, maybe for the 10 years prior to this year, Bitcoin would have been worth way more than any of the other points or miles you had if you've been buying it for the last 10 years. And that's definitely true. But the same is true if you had been using a cashback card and using that cashback to buy crypto. It's not about which card you use. It's about whether you're deciding to buy crypto. And so, you know, I'm sure we could do a whole other podcast about how to think about allocating an investment portfolio, but we're not going to go deep there. So I think that's really more

of a question of I love automating investment behavior. I spend a lot of time in my day job at wealthfront, like building software to automate people's financial lives to help them build wealth. And so I'm a big fan of automation. If the only thing that's going to get you to invest is to use a credit card that automatically invests your rewards. I'd rather you do that because I think investing is a really powerful thing to do. But, you know, if you want to earn rewards and fly around the world and travel for free and just invest your money that you're not spending on travel because you're now traveling for free, that's great also.

So let's wrap up. We've talked a lot about tips for people who want to earn points and miles and or who have points in miles that they want to redeem. What advice do you have for anyone who neither has nor want to. to have points or miles, but they still want to get deals, particularly when traveling. So if those people are still listening, thank you for listening through all of the talk about miles and points. I'll give a few. My favorite travel hack has nothing to do with points and miles. And it's probably like the single biggest thing I've get emails about because so many of the listeners of my show have gotten great success. And it's super simple. You're going to

stay at a hotel. You book the hotel directly with the hotel on the hotel's website. And after you book it, you email the hotel. If you don't have the hotel's email address, call the front desk, ask for an email address. You say, hey, I'm coming to your hotel. I'm really excited to be staying with you. If you're celebrating anything, let them know, you can tell them why you're coming. Just you're trying to build a relationship. As much as we think hotels are just transactional, they're really in the hospitality business. And all the other channels you book through, they often don't even get your name until days before the booking. So book direct asks that, and then maybe follow up a week before, a couple days before, say, hey, just want to follow up. I'm really excited to see you guys this

week. See you then. That's all I would do. I think I've probably gotten at least 100 emails from listeners who've been upgraded, gotten a bottle of champagne, or the most unique one was had their initials monogrammed on their pillows for their bed, which I thought I would much rather have a bottle of champagne for free than have my initials monogrammed on a pillow. But so that's one that works for anyone. You're booking a hotel. Always book direct and email the hotel. The flip to that is if you are splurging and you're booking a super expensive high-end hotel,

you know, let's call it in the five-star category, probably hundreds of dollars a night or, you know, maybe even over a thousand. Most hotels offer really great perks to people who book through a travel channel that is a travel agency or in some cases, you know, like a program. like Amex's fine hotels and resorts, booking through one of those channels usually gets you a property credit, free breakfast, upgrade, early check-in, maybe late checkout, free Wi-Fi, all those things. And hotels really value people who book through travel advisors and they know that travel advisors help build the relationship with the hotel and so they offer those perks. So that's one. You can do it through those programs. I'll do a shameless plug that we partnered with the travel agency to be able to give all all the hacks listeners.

that whole thing. So if you just go to all the hacks.com slash upgrade, you can read about it. So those are two. On flights, I don't think there's a better tool to save money on flights than Google flights. Almost every flight search begins there

because there are very few places online where you can say, I want to go from San Francisco, and then you can say things like on a flight that's less than 10 hours and has less than one stop for a week in July and move the map

and just see where in Europe you could go, see where in Asia you could go. You know, you can put multiple from airports, from San Francisco or Oakland or San Jose, from Newark and LaGuardia and JFK. I think clicking through dates, looking at their calendar is one of the best ways

to find cheap, international, domestic, anything flights. You can even set alerts. So that's one of the best products that has kind of come to the market in the last 10 years to save money on flights. Those are a few of my favorites.

The last I'd say is if you're a member of Costco, You know, Costco for rental cars has travel discounts for a lot of rental car companies. So do a lot of credit card companies. I actually just wrote this newsletter all about credit card benefits that people don't really realize they have. And there are a lot of credit cards that have rental car discounts that offer car rental insurance so you can decline the rental coverage that offer tons of travel insurance. This is not on this topic of travel, but I've probably cracked a phone screen four times in my life. and two or three of them were paid for by the free insurance I got by paying for that phone on a credit card.

Most credit cards have purchase protection that if you break something within the first three or four months, they'll replace it, whether it's damaged, stolen, broken, or anything. I don't know. Those are a few of my kind of fun savings hacks, but you know, you guys all hopefully at this point know where to go if you want more of them. Awesome. Well, thank you so much for spending this time with us. Where can people find you if they'd like to hear more about you and your hacks? Yeah, so I have a show called All the Hacks. You're listening to a podcast right now. So hopefully you can just go find that wherever you're listening to podcast. We publish weekly.

Got AlltheHacks.com. We write all the show notes. There's a link to the newsletter. There's a link to cards I recommend, all kinds of stuff on AlltheHacks.com as well. And then you can just find me social media anywhere, DM me, email me. I love to hear from people. I love answering questions. Email is just Chris at AlltheHacks.com.

Awesome. Thank you so much, Chris. Thanks for having me. Thank you, Chris. What are three key takeaways that we got from this conversation? Number one, don't overthink it. Think about how you tend to spend money and then open up a credit card that aligns with that. So if you tend to spend a lot of money on gas and groceries more so than any other spend categories, get a card that aligns with that. If you tend to spend your money on flights and travel, get a card that aligns with that. You can just get one card, keep it simple, and once every couple of years, you'll rack up enough miles or points to enjoy something really special.

It doesn't have to be this big, complicated thing. You can keep it simple and optimize for the way that you already spend. The simple version of just, I'm going to open up one credit card right now that aligns with how I spend money. You spend your money on travel and dining, get a card that focuses on that. You spend your money on groceries, maybe focus on a card there. You don't really spend anywhere specific. Get a card that just earns two points per dollar on everything. That kind of simple path of I'm going to open up a card. I'm going to get the sign up bonus.

And then I'm just going to spend, depending on how much money you spend, maybe you end up racking up a few hundred thousand points every few years and taking a vacation for your family every couple years. You want to get extreme and open up five cards a year, 10 cards a year, have the spreadsheets, go buy everything you want through gift cards that you bought at the grocery store through your grocery store card or at the office supply store with your office supply store card, you can do that.

I don't think it's an all or nothing game where you have to go that far down the rabbit hole to start to get value. So that is the first key takeaway. Number two. There are two elements to using reward points. One is accumulation, and we hear a lot about that. The other is redemption, and we don't hear as much about that. Now, the bad news is some of the resources that used to be there for figuring out the best flights

to book for Opt More Redemption. Some of those resources don't exist anymore. That's the bad news. The good news is that a lot of bloggers, podcasters, a lot of individuals have stepped in to fill in the gaps. Content creators have come in to fill in the gaps that software has left behind. And so a little bit of searching can get you a long way when it comes to looking up specific information about how to optimize your redemption for going to a specific. destination. The downside is it used to be really easy. You'd say, okay, if I want to go from here

to there, the limitation is two things. What airline flies there? So, okay, there's five airlines that fly here. Then you could go look at all the websites of the airlines that fly there and their partners and say who has the cheapest. So that's the downside is that those don't exist. The upside is there's now 20 or 30 or 40 or probably thousands of blogs about this. If you go online right now and say best Miles Redemption to go to the Maldives. I bet there are seven blog posts at least where someone who is as much of a nerd or more than I am, has gone in an outline here with chase points or Amex points is the best way to get to the Maldives. So make your search specific and you'll be surprised at how much you can find.

That is key takeaway number two. Finally, key takeaway number three, flexibility is key to getting great deal. The more flexible you can be, and particularly the more ability you have to take advantage of last-minute deals, the better of a deal you're likely to find. All of the availability for many airlines becomes much easier last minute. Many people, especially myself now that we have children, are maybe not as comfortable with this tactic. But if you're listening to this and you're comfortable with it, my wife and I sometimes would say, we're taking this week off to go on vacation. but we don't know where we're going. And like a week before, or in some cases, like four or five days before we would just start

searching, and things open up like crazy in terms of the number of points you need to go somewhere. So if you're flexible and you book within a week or two, you can sometimes get really, really great deals with points. And depending on the airline, one of the positive things, maybe one of the only few positive things to come out of the pandemic is a lot of airlines getting rid of their cancellation fees. So if you book a flight, and this is very true for rental cars, by the way, I'll come back to that. But if you book a flight and it costs 100,000 points for two people to go to Europe, which is actually pretty good. So maybe you're not going to get better than that.

But if you book a flight and a week before you search and it now costs half as many miles, you can always just book that and then cancel the original one. Those are three key takeaways from this conversation with Chris Hutchins. Thank you so much for tuning in. If you got value from this episode, if you learned something, please share this episode with a friend or a family member. That's the most important thing that you can do to spread this information. One of the easiest ways to share this episode is to forward the show notes. You can subscribe to the show notes for free at afford anything.com slash show notes. When you subscribe, you will get timestamps of many of the key points that we've made in this episode delivered straight to your inbox.

It's totally free. and it's a great way for you to have a reference point with timestamps that shows you exactly when we've talked about what. So afford anything.com slash show notes. You can subscribe to the show notes. You can also share it with a friend or a family member. Please also open whatever app you're using to listen to this podcast and leave us a review. And while you're there, make sure that you hit the follow button so that you don't miss any of our awesome upcoming shows. You can chat about this episode with other members of the community at afford anything.com slash community,

where we have villages that talk about specific areas of interest, including traveling, travel hacking, points, everything that we've discussed today. Thank you so much for tuning in. My name is Paula Pant. This is the Afford Anything podcast, and I will catch you in the next episode.