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

👉 Join Master Money Academy today! In this episode of The Personal Finance Podcast, Andrew talks withChris Hutchins—host of All The Hacks and one of the smartest people in the travel rewards world, to answer the burning question: Is travel hacking still worth it as credit card annual fees skyrocket and loyalty programs devalue points left and right, breaking down Chase versus Amex strategies, the rise of cashback alternatives, how to build a smart travel rewards plan for that dream trip you've been planning, revealing advanced tactics and underrated transfer partners that most people don't even realize exist, plus sharing some of the funniest and most ridiculous stories from the world of points and miles, helping you separate signal from noise and squeeze insane value out of rewards programs even as the game continues to evolve. How Andrew Can Help You: Listen to The Business Show here. Don't let another year pass by without making significant strides toward your dreams. "Master Your Money Goals" is your pathway to a future where your aspirations are not just wishes but realities. Enroll now and make this year count! Join The Master Money Newsletter where you will become smarter with your money in 5 minutes or less per week Here! Learn to invest by joining Index Fund Pro! This is Andrew’s course teaching you how to invest! Watch The Master Money Youtube Channel! , Ask Andrew a question on Instagram or TikTok Learn how to get out of Debt by joining our Free Course Leave Feedback or Episode Requests here. Car buying Calculator here Thanks to Our Amazing Sponsors for supporting The Personal Finance Podcast DELL: Get a new Dell AI PC starting at $749.99, at Dell.com/ai-pc Indeed: Start hiring NOW with a SEVENTY-FIVE DOLLAR SPONSORED JOB CREDIT to upgrade your job post at Indeed.com/personalfinance Acorns: Start investing automatically with Acorns and get a $5 bonus at Acorns.com/PFP Chime: Start your credit journey with Chime. Sign-up takes only two minutes and doesn’t affect your credit score. Get started at chime.com/ Thanks to Policy Genius for Sponsoring the show! Go to policygenius.com to get your free life insurance quote. Shopify: Shopify makes it so easy to sell. Sign up for a one-dollar-per-month trial period at shopify.com/pfp Go to https://joindeleteme.com/PFP20/ and Use Promo Code PFP for 20% off! Connect with Chris Hutchins: All The Hacks Podcast Newsletter Instagram Linkedin X Connect With Andrew on Social Media: Instagram TikTok Twitter Master Money Website Master Money Youtube Channel Free Guides: The Stairway to Wealth: The Order of Operations for your Money How to Negotiate Your Salary The 75 Day Money Challenge Get out Of Debt Fast Take the Money Personality Quiz Learn more about your ad choices. Visit megaphone.fm/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Andrew Giancola?

  Now, if you watch this podcast on Spotify, Apple Podcasts, or YouTube, you've probably noticed the wood slat walls behind us. We wanted this podcast set to look professional, but also not be a project that was overly complicated. And I found these slat walls on Wayfair, and it completely changed this space. And it's now basically the background that you see in every single podcast or piece of content that we record. And that's one of the things that I love about Wayfair. You can shop thousands of products across different styles and budgets, use customer photos and reviews to see how things actually look in real homes, and find something that fits your space. They also have Wayfair Verified Products that are hand vetted by product specialists using a 10-point quality inspection.

• 0:44Andrew Giancola?

  And with more than 20 million verified 5-star reviews, you can feel a lot more confident about what you're ordering. I've used Wayfair for this studio and our home, and I absolutely recommend them for your space. So transform your space with pieces that hold up to real life. Join Wayfair Rewards today and get 5% back on every single purchase. Head to wayfair.com or shop the Wayfair app for all things home. That's W-A-Y-F-A-I-R dot com. Wayfair, every style, every home.

• 1:17Speaker 01

  Wayfair, every style, every home.

• 1:20Andrew Giancola?

  When I started the Personal Finance Podcast, I had no idea how big it could become. I just knew I had something I wanted to share, so I started putting it online. And looking back, I definitely wish I would have started a decade earlier. One of the horror parts about building something online, though, is making it look professional. A website used to mean hiring a developer, figuring out design, and potentially spending thousands of dollars. In fact, on my website, I spent tens of thousands of dollars. That's what impressed me when playing around with Hostinger's AI Website Builder. I told it what kind of website I wanted, and I built the first version in minutes. No coding, no designer or developer needed. And Hostinger doesn't stop at launch.

• 2:04Andrew Giancola?

  Their AI can help with SEO, website copy, email marketing, and more. Your domain, website, email, and marketing can all live in one account with plans starting at just $3 every single month. Hosting or build your vision step by step. Create your website today. Go to hosting.com/pfp and use code PFP for 10% off now. On this episode of the Personal Finance Podcast, is travel hacking dead? We're going to ask Chris Hutchins.

• 2:51Andrew Giancola?

  What's up everybody and welcome to the Personal Finance Podcast. I'm your host, Andrew, founder of mastermoney.co. And today on the Personal Finance Podcast, we're going to be talking to Chris Hutchins about travel hacking. If you guys have any questions, make sure you join the Master Money Newsletter by going to mastermoney.co/newsletter. And don't forget to follow us on Spotify, Apple Podcasts, YouTube, or whatever podcast player you love listening to this podcast on. And if you want to help out the show, consider leaving a five star rating and review on Apple Podcasts, Spotify, or your favorite podcast player. Now today, we're going to be diving deep into a topic that's been heating up in the travel rewards world. Is the game still worth playing right now? See, credit

• 3:35Andrew Giancola?

  card annual fees are skyrocketing and loyalty programs are devaluing points left and right. And a lot of people are asking a fair question. Is this still worth it for the average person? Or has the golden era of travel hacking started to fade? Now, to help us separate signal from noise, I brought in one of the smartest people I know when it comes to points, miles, and optimization, the host of all the hacks, Chris Hutchins. Now, Chris has traveled the world on points, built incredible strategies around loyalty programs, and is known for squeezing insane value out of rewards that most people don't even realize exists. And today, we're going to break down a bunch of different things from Chase vs. Amex, loyalty point devaluations, and the rise of cash back strategies to how to build

• 4:17Andrew Giancola?

  a smart travel rewards plan for that big trip you've been dreaming about. We'll also dig into advanced tactics, underrated transfer partners, and yes, some of the funniest and most ridiculous stories from the worlds of points and miles. So without further ado, let's welcome Chris to the Personal Finance Podcast. So Chris, welcome back to the Personal Finance Podcast.

• 4:38Speaker 02

  Dude, I am excited to be here.

• 4:40Andrew Giancola?

  I am pumped to talk about this because we are getting a ton of questions coming in. A lot of people are kind of setting up plans for where they want to travel. They're talking about points and miles and a lot of things have shifted in the points and miles game over the course of the last couple of years that I want to talk through here today. So we have seen credit card annual fees skyrocketing. We've seen it across, you know, things like the Chase Sapphire. We've seen it across Amex and these fees are rising, but then the perks that are associated with them, a lot of people are saying, well, maybe these perks are worth it, maybe they're not. But what is your honest take and is this hobby worth it for most people in 2025?

• 5:13Speaker 02

  I think that for the right person, the hobby is definitely worth it. If you're able to take advantage of big welcome bonuses, use your points to take vacations, I think you will come out ahead. That said, I think that if your end result is you're often just like booking in the Amex and Chase travel portals, I'm not convinced that you would have been better off earning points over cash back. The real value still comes from when you take your points and you transfer them to travel partners, airlines, hotels and book with them. However, the points and miles cards offer the most generous welcome bonuses. So I could argue that cash back could be more competitive, but a good cash back card might say, hey, sign up for our card and you get 200 bucks.

• 5:58Speaker 02

  And a good points and miles card might say, hey, sign up for our card and we give you 200,000 points, which is like $2,000. So if you're always working on a welcome bonus, points is going to be your best friend. If you're never working on a welcome bonus, you just want one card, you never want to open up another card ever again, well, it's going to be tough to win on the point side if you are not taking those points and transferring them to airlines, which inherently requires you to have some flexibility. The other place I think that we kind of get caught up is saying, what are all these credits worth on these cards? And I would push people back and say, ask yourself how much you would buy someone else's credits for, and they might not be worth as much as you think, right? Like if your Chase card gives you $250 every six months off of a booking of

• 6:44Speaker 02

  The edit through their like luxury hotel program. You can't call that $250 because I am sure you wouldn't buy it for $250. Right? Like if you asked your friend, hey, will you book a hotel for me? You know, like, and you're going to cash out their $250 credit. It should be worth a lot less. And so I think you can get value out of a lot of these credits that justify, quote unquote, these really high annual fees. But you've got to be honest about what they're really worth. And sometimes if you're booking a hotel, you've never were a book in the first place to get $250 off. I wonder whether that's really worth $250.

• 7:18Andrew Giancola?

  And there's two types of people that we kind of come across when it comes to this hobby that I've noticed as of late. And one is the optimizers. The optimizers are the ones that are going to focus on trying to transfer those points to those transfer partners. And really want to be able to go out there and get some of these free trips. Then there's people who want to simplify their finances. They want the simplest path possible. They're going to stick with that one card. And so like you're saying, maybe cash back is the better option for them. Because if they want to stick to one or two cards, that may be the way to go. But the signup bonuses are the real way to actually acquire points. And that's the name of the game if you're looking to travel hack going forward. Now, there's a big, big piece that's been in the news a lot as of late, and it's Chase versus Amex. And there's a lot of, you know, the new cards that are coming out where they have all these additional perks.

• 8:01Andrew Giancola?

  But those yearly fees are really, really high. So which one has better rewards right now in your opinion? And is it worth it?

• 8:08Speaker 02

  Well, it's interesting. So Chase and Amex have been competing. So Chase came out and they're like, we're going to bring the high annual fee from, you know, I think it was five, 650 or 595 up to 795. And Amex, without even saying what they were going to do, said, no, no, no. Our card's coming out. We're not going to tell you why it's better, but it's going to be a higher annual fee. It's like, who can have the highest annual fee seems to be the game they're competing on. I would say there's a lot of ways to look at this. And by the way, Capital One, I think is just as compelling. And they've said, you know, we're not going to play this game. We're not going to try to have the highest annual fee. And from that perspective, I would say maybe they're the ones that people should be thinking about. They've added a couple of new transfer partners. Meanwhile, Amex has lost a couple, like Capital One's, I would put in the running up against Chase and Amex. But between the two really

• 8:54Speaker 02

  expensive cards. I think it's pretty clear that Amex added a lot more value for the increase in fee than I think Chase did. So when you're just looking at whose card justifies the annual fee, I think it's probably Amex. If you're looking at whose rewards are better, I think I give the edge to Chase. And it's primarily because Chase still has opportunities in their travel portal to book things at an elevated value. It used to be that if you had their premium cards, you guaranteed you could book any travel for one and a half cents. They got rid of that and now it's between one and two cents, depending on the flight, the hotel and all this stuff. But I think it's easier to get more value out of your points in all scenarios with Chase than it is with Amex.

• 9:37Speaker 02

  But I think it's just so much easier to earn Amex points. Amex has so many more cards. They're doing so many more promotions. The lucrative signup bonuses. So I think it's easier to earn Amex points. It's probably easier for the average person to get more value out of their Chase points.

• 9:50Andrew Giancola?

  And for those of you who haven't seen it, it's, you know, Chase and Amex have come out with just all these additional perks that they've thrown out. And Amex is the big one as of late where they've added in things like a $200 Lumen credit and they've added resi credits and they've added in, you know, aura ring credits. And people are buying aura rings just to get those credits. And that's one of the traps I think people are falling into is they're spending more dollars on specific things just to get those credits, plus the yearly subscription and all those different things. And so really, overall, you got to figure out, hey, what brings the most value to what I am trying to do? And then kind of go from there. Now, I agree with you. I think Chase has just so many different transfer partners. But Amex does have a bunch of different ways to acquire points. And so that's kind of the trade off that you have there. So how have loyalty point devaluations changed your personal strategy?

• 10:32Andrew Giancola?

  How do you actually think about this within your personal strategy of how you look at cards and open cards?

• 10:37Speaker 02

  So on one hand, you could look at it and say, wow, I can't remember. I went back and looked at one of my first international trips I ever booked. You know, it was like 50,000 points, round trip in business class. It was some like amazing thing. And now it would cost twice as much as it would. And I looked back at some old historical signup bonuses. There was a period of time where a card would offer 30,000 points and that was amazing. And so, yes, if you want to book flights with your points, it costs more, not just. Just because the underlying dollar cost of the flights has gone up, but airlines that have kind of fixed prices, they're like, oh, you know, flights used to be 50,000, now they're 80,000. They're always going up in price, which means that your points are effectively getting devalued.

• 11:18Speaker 02

  But back in the day, a 50,000 point signup bonus was incredible. Back in the day, I had a card that earned like one and a half points on everything. It was incredible. Now you have cards earning three, four, five points per dollar. You have signup bonuses that are all the way up to, I think the highest recently is 300,000 points for an Amex Business Platinum. So, do I hate that my points are worth less? Yes. Do I love that I can earn them at a faster clip? Yes. So I actually think we've come out ahead. I think that it feels worse because the points we have are worth less, but I think you can accumulate them faster than they are getting devalued. Does that trend continue forever? I don't know. But the fact that there are credit cards offering 100, 200, 300,000 points to get started,

• 12:03Speaker 02

  like, that is something we've never seen before, and it more than makes up for the fact that you might need 20% more points for the trip you want to take.

• 12:11Andrew Giancola?

  Agreed, and I think that's the big thing is you can just earn them so much easier. There's a bunch of different ways that you can earn points that just will accelerate your path to getting to that higher number. So overall, there's a big, big difference for sure. And I think we kind of alluded to this early on, but you talked about, you know, cash back cards might be a better option for a lot of people. And there's a number of different things that you can do with cash cards. Can you kind of talk about why that might be an option for some people and what you can do with cash back cards? Specifically when it comes to even like taking those dollars and investing them, or taking those points and turning them into investment dollars, and kind of looking at it from a personal finance perspective too?

• 12:42Speaker 02

  Yeah, I mean, there's no surprise that these points are getting devalued over time. And if you take cash and you put it in a high-yield savings account, it increases in value over time. So that like, that is an argument for cash back is that the pool of dollars that you've earned versus points you've earned will grow. That said, if you're getting two, three, four cents of value out of your points, like, you know, it's going to beat whatever growth you'd get on your cash back. Another thing that I think is really underappreciated in this hobby, if you will, is that when you book a flight and you pay for your ticket with cash You earn miles, right? You don't just earn miles on your credit card for booking the flight, or you earn cash back for booking the flight on your credit card. But all the airline programs are going to give you points that you usually don't earn on an award ticket.

• 13:26Speaker 02

  My math shows, and I did a ton of analysis recently on an episode about what are points actually worth a few weeks ago, and I think that you're getting about 10 to 20% of the value of a cash ticket back in terms of earning status, earning points, credit card points. So tickets are basically 10 to 20% cheaper with cash than with points because of all those benefits. So that's one thing that I think often gets lost in the numbers. So I think cash back can be really, really compelling. You could buy whatever ticket you want. You can go whenever you want. You earn points on those flights. You earn points on your cards. It's super simple and straightforward, and you don't need the baked in flexibility that you need to get maximum value out of your points.

• 14:08Speaker 02

  So I am a fan, especially, as I said before, for people who don't want to open 5, 10, 15, 20 cards a year, right? Because that's where the real lucrative benefits are. And there are some cash back cards now that are 3% on everything, 4% on everything, up to like $10,000 a month of spend. So I think for, for people who aren't spending, let's say, more than $100,000 a year on a credit card and don't want to open up lots of cards, there are a lot of lucrative cash back options.

• 14:39Andrew Giancola?

  And I think that's a huge, huge perk overall is being able to kind of recognize that, especially if you want to have, you know, less cards, is to be able to just find, you know, the highest cash back that you can find. Now, I have know people, for example, who have utilized their cash back for long periods of times. And for listeners who haven't heard of this strategy before, they have taken those cash back dollars and they have built six-figure emergency funds with them, and now are taking all the cash back, and they're just kind of growing their, their wealth and investing their dollars in places like Fidelity. I've heard you mentioned before the show, Morgan Stanley, you could transfer Amex points there. So there's a lot of different things that you can do, I think, that are really, really powerful. If your focus is, you know, financial independence or building wealth, and that's the number one thing you want to do. You don't care about traveling as much as being able to put those dollars towards things like wealth building, then that's, I think, a really powerful place to start. So there's all these different cards out there.

• 15:24Andrew Giancola?

  There's all these different premium cards that are coming out, and a lot of people are trying to see, well, does this annual fee even make sense? Can I actually justify this annual fee? Or is it something I should just avoid and just go to a standard card with a normally annual fee every single year? So how should someone look at this and evaluate whether premium card perks are actually worth it for them?

• 15:42Speaker 02

  So this is something that really drives me crazy. Someone emailed me and said, oh, the AMX annual fee is going up to 8.95. I'm canceling the card. And I was like, well, you had the card before the fee went up and you were okay with it. Right? So you were okay with 6.95. You're not okay with 8.95. On the personal platinum card, it went up $200 and they increased the perks of the card from getting $200 of hotel credit to $600 a year. They gave you a $300 Lululemon credit. They gave you a $200 Aura credit. Like they added on a lot more value than that $200. So I could make a case that the 8.95 fee doesn't make sense for someone. It would be really hard to make the case that the $200 increase for someone who thought it was worth it before is now in a worse position.

• 16:25Speaker 02

  But I think at the end of the day, you have to ask yourself like, what's the real value you're getting out of these things? If you, like you said, don't want an Aura ring, now you have a $200 Aura credit. So you buy a $400 ring that you didn't even want in the first place. And now you're paying six bucks a month to keep this subscription active. Then it's hard for me to say that you got $200 of value out of that credit. In a way, you got negative value out of that credit. By having that credit, you're now spending money you didn't want to spend. That credit is worth negative to you. Now, if you bought a $400 ring, Aura, got $200 back and went and sold it online for, you know, 300 bucks, then you made $100. So if you don't care about Lululemon clothes, but you buy $75 Lululemon gift cards that

• 17:10Speaker 02

  you sell for 60 bucks, you're getting real dollars back. But if you go buy a bunch of Lululemon clothes that you never wanted or needed and it doesn't replace any purchase you were gonna make anyways, you definitely didn't get $75 of value. Maybe you got $20, like you can ask yourself how much value you got out of it. They have this $50 every six month Saks credit. There's nothing at Saks I really want. So I end up buying like two pairs of underwear, right? Like I wouldn't spend $50 on two pairs of underwear normally. So I can't call it $50 of value. Maybe it saved me 20 bucks, you know? Like plus, how much time did it take me to spend searching on the Saks website to try to find something I wanted? Like if I value my time at really anything, it's probably worth zero. So again, I would.

• 17:52Speaker 02

  Back up and the question I would ask yourself is run through all the perks of that card and ask yourself what you would buy those perks for. How much would you buy $300 of Lululemon credit for? If you spend $1,000 at Lulu every year, you'd probably buy it for, I don't know, $275? You know, like that's real value. If you regularly book hotels, premium luxury hotels through Amex's travel portal, getting $300 off every six months, worth a lot. But if you never shop at Lulu and you never go to these hotels, those perks are only worth a lot less unless you're finding creative ways to, you know, book a hotel for your friend and have them reimburse you. Like there are some creative ways to do it. But at the end of the day, I think you gotta be honest with yourself and just say, what would I buy this for?

• 18:34Speaker 02

  What would I buy a $300 travel credit for? On Chase cards, that $300 travel credit is so easy to use. You book any travel on your card and they just reimburse you. So like on the Chase Sapphire Reserve, that travel credit to me is worth pretty much $300 because all I have to do to get value out of it is book travel. I'm gonna book $300 a travel a year. But some of these other things, like I personally value the Chase the Edit $250 credit at zero because I don't stay in hotels through that platform that cost that amount, ever. So I can't value that credit at anything. That's what I think you gotta be honest about yourself is how much value are you really getting? And I know that Frequent Miler, I can send you the link. They have this premium card worksheet where it lists all the perks out and it gives you the ability to say like, here's how much I value it.

• 19:18Speaker 02

  And you can kind of do the math to see if it's really worth it. And I think for someone who's a real optimizer, I get a lot of value. I'm certain that I spend more than $10,000 a year in annual fees. And I've done the analysis like hyper competitively, like very thoroughly that I get enough value. But I spent a lot of time doing this. I do it for a living. So I'm not saying that other people should adopt that strategy.

• 19:40Andrew Giancola?

  And I do love that the way you're thinking about this too, because a lot of these perks, you can just think of even examples. Like you mentioned the example for Lululemon gift cards. Well, you can even think through all of these different perks. If you're not going to use the Aura Ring credit, for example, you can gift that. I mean, the holidays are coming around. You can gift those types of things and really get a reduction in even the cost that you're going to be spending on gifts coming around the holidays. There's a lot of different ways to use this stuff. And like you said, I think having Or having something in place that actually has a plan of how you're going to use these perks and see if the value outweighs what you're actually spending each and every single year. That's the only way to really look at this in a responsible way. If you're trying to really optimize and squeeze every single dime out of these cards, that's the real way to do it because you got to, A, you got to understand what all the perks are. Some people go into these, they don't even understand or know some of the perks they have with these cards.

• 20:24Andrew Giancola?

  And then two, you have to have a plan in place in order to make sure that we are looking at that properly. So I think that's a great way to look at it overall.

• 20:31Speaker 02

  But if you're looking at a card like the MX Platinum card, and you're able to get 175,000 point signup bonus, right? Which at the least should be worth $1,750, right? For that first year, I'm less concerned about whether you'll get the full $895 out of the value of the card because you're getting $1,750 to open it. And if those points are used more strategically, maybe you're getting $3,000. So if those perks are only worth $400 to you, then your actual annual fee is $495. Okay, that's fine. You're paying $495 for almost $2,000 or more dollars of value. I'm okay with that trade off. At the end of the year, though, when it comes time to say, do I keep this card open?

• 21:14Speaker 02

  I would always encourage you to say, well, if the value's not there, talk to MX, talk to Chase. Sometimes if you say, hey, the value's not here, I don't think I want to renew this card. Sometimes they'll say, hey, well, what if we give you 50,000 points? What if we, like, there are often retention conversations that can be had to get more out of a card before you close it if the value's not there. So have that conversation. You could downgrade cards to no or low annual fee cards, and you can close them. So there are a lot of options you have at the end of the year. But I would isolate the value the first year from the following years because sometimes those welcome bonuses are just so lucrative that the annual fee doesn't matter. Like, honestly, like, there are cards where the welcome bonus is so big

• 21:55Speaker 02

  that if it had a $500 fee and no perks, none, not a single credit coupon, anything, it'd still be worth it.

• 22:01Andrew Giancola?

  And that's a huge, huge point to remember is that these welcome bonuses are the first key to look at in terms of making sure you draft out your plan. And if those are in place and those are really outweighing everything else, I mean, that's a huge, huge difference maker for sure. And then downgrading those cards is the easiest way. You just kind of keep your credit intact and everything else. And I think that's really, really important to look at.

• 22:19Andrew Giancola?

  Now, 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 were trying to build out a strategy to start travel for free?

• 22:50Speaker 02

  I 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 opened up a bunch of cash back cards and you spent all your money on cash back, 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. Here'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?

• 23:35Speaker 02

  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. So 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

• 24:17Speaker 02

  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, but 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,

• 25:01Speaker 02

  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. So when I say flexibility, it might be what route you take. It might be what day you fly. It might be, you know, how many layovers you have. It might be how soon you find out where you're going. I told my wife this, so we were 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.

• 25:41Speaker 02

  So I couldn't even, planning one year in advance, I couldn't even get all four of us on the same flight. So 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 gonna be together. I just can't tell you whether we'll find out at the airport. Like, 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.

• 26:26Speaker 02

  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. We'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,

• 27:10Speaker 02

  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.

• 27:22Andrew Giancola?

  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. And 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 was willing to kind of optimize here. What 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?

• 28:06Speaker 02

  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 to 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? Because 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?

• 28:51Speaker 02

  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. Or 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.

• 29:34Speaker 02

  And 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, Citi, 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? Like, I would much rather have a card that was going to 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

• 30:16Speaker 02

  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. And so the influence of how many accounts do you have? How much of your open credit are you spending? If you have $20,000 of credit- Limit and you spend $5,000 a month.

• 31:00Andrew Giancola?

  Right.

• 31:00Speaker 02

  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 card. 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 of new inquiries that you get every time you open a card. Average length is going to be shorter. So it will have an impact. I did 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.

• 31:39Andrew Giancola?

  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. So 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?

• 32:12Speaker 02

  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. Then I'm gonna do this one and get 175,000 Amex points. And I'm gonna 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 allthehacks.com/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

• 32:57Speaker 02

  where all of the points transfer. So if you're like, Avios is a transfer partner of everyone. Air France is everyone except this new homeownership 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. When 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 Swissair, 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.

• 33:41Speaker 02

  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. Well, 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.

• 34:22Speaker 02

  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. You know, like, it'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.

• 35:06Speaker 02

  If you're a renter, the Built Card's interesting because you can 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. But 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.

• 35:33Andrew Giancola?

  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 can pay your home costs, 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. You know, 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.

• 35:53Speaker 02

  So 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 said you upload your mortgage statement and say, hey, we spend $4,000 a month on our mortgage. And as long as you spend a thousand dollars a month on their card, they just give you 4,000 points. You don't even need to pay the mortgage because, you know, 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. So 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 Built, 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.

• 36:37Speaker 02

  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.

• 36:43Andrew Giancola?

  For sure. I think that's such a huge tip for anybody. Anybody can utilize those because somebody's, you're paying rent or mortgage unless you, you know, are living with someone for free somehow. So 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?

• 37:12Speaker 02

  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/166. And 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.

• 37:55Speaker 02

  And 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. I go where the flights are. And so I've gotten a lot of value recently out of Air France,

• 38:36Speaker 02

  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. So 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.

• 39:20Speaker 02

  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. But 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 as 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.

• 40:05Speaker 02

  So it depends on the airline, what the fees are for cancelling. Which one do I like? Honestly, whichever one has the flights. I think that I've 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 Citi transfers to American, only Bilt transfers to Alaska, only Chase transfers to United. So 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.

• 40:49Speaker 02

  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, Bilt, Citi, Wells Fargo, except for Air Canada. They don't work with Citi and Wells Fargo, but like a lot of options.

• 41:08Andrew Giancola?

  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 they'll just go into the travel portal and they'll book all of their travel there. Do 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?

• 41:23Speaker 02

  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, so 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,

• 42:07Speaker 02

  by all means, go use the travel portal. But if you're really 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. They 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 seeing 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. Like, I'm okay with two cents a point. Like, 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.

• 42:52Speaker 02

  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. And anytime you book flights in the travel portal, they give you a 35% rebate if you use points. And so you're, 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 cash back.

• 43:38Andrew Giancola?

  I 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 through the travel portal every single time, then cash back 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 cost 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?

• 44:02Speaker 02

  I think it's a combination of patience and flexibility and diversification. So 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 like doubled the price. Great, well, I still have a dozen others I can use. Whereas if I were only earning points with Delta,

• 44:44Speaker 02

  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. That'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?

• 45:27Speaker 02

  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.

• 45:37Andrew Giancola?

  Exactly.

• 45:38Speaker 02

  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, like 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.

• 46:04Andrew Giancola?

  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. It's just pure flexibility is what you really want when it comes to this game.

• 46:17Andrew Giancola?

  It's kind of amazing how much can change in just a single year. Every summer, the kids are a little bigger, a little more independent, and life looks a little different than it did the year before. And it reminds me that while we can't predict the future, we can prepare for it. That's one of the reasons I like PolicyGenius. See, PolicyGenius isn't an insurance company. They're an online marketplace that lets you compare life insurance quotes from some of America's top insurers, side by side, for free. And their licensed team helps you compare coverage, prices, and terms, answers your questions, and even handles the paperwork so you can get the right policy without the hassle. For me, having life insurance isn't about expecting something to happen. It's about knowing my family is protected

• 47:01Andrew Giancola?

  so I can actually enjoy these moments together instead of worrying about what comes next. And with PolicyGenius, you can find 20-year life insurance policies, starting at just $276 a year for $1 million of coverage. Head to PolicyGenius.com to compare life insurance quotes from top companies and see how much you can save. That's PolicyGenius.com. If you've been listening to this show for a while, you know it's not just me anymore. It takes a great team behind the scenes to make everything happen. And if I had to hire someone tomorrow, I'd want someone who could jump right in and make an impact. That's why I'd use Indeed Sponsored Jobs. When workplace chaos hits, Indeed Sponsored Jobs helps you reach qualified candidates faster.

• 47:45Andrew Giancola?

  Your job gets boosted in search results so you're spending less time searching and more time interviewing the right people. Plus, you only pay for results, which I absolutely love. Sponsored jobs posted directly on Indeed are 95% more likely to report a hire than non-sponsored posts. That's a huge advantage when you're trying to grow your business. Spend less time searching and more time actually interviewing candidates who check all of your boxes. Less stress, less time, more results. When you need the right person to cut through the chaos, this is the job for Indeed Sponsored Jobs. And listeners of this show will get a $75 sponsored job credit to help get your job the Premium status it deserves at indeed.com/podcast.

• 48:30Andrew Giancola?

  Just go to indeed.com/podcast right now and support our show by saying you heard about Indeed on this podcast. Indeed.com/podcast. Terms and conditions apply. Need to hire? This is a job for Indeed sponsored jobs. One thing I've learned from running multiple businesses is there's usually a gap between how you think work is getting done and how it's actually getting done. And we've had times where we thought we knew the bottleneck, only to realize later, the real issue was somewhere completely different. That's exactly what today's sponsor, Scribe, helps solve. Scribe is a workflow AI platform trusted by 94% of the Fortune 500. And Scribe Optimize turns real workflow data into decisions your AI strategy actually needs.

• 49:14Andrew Giancola?

  Automatically capturing how work happens across approved apps, surfacing inefficiency and opportunities with no interviews and no manual discovery and no extra work from your team, which is the key. And the live dashboard shows where work is happening, how much time it's taking and where the biggest opportunities are right now. It automatically discovers workflows across multiple tools, then highlights your biggest inefficiencies and gives AI-powered recommendations with estimated time-saving. You know, I love saving time. It's also built with privacy in mind. It only runs across approved business applications, user-level data is anonymous by default, and sensitive information is automatically redacted and never leaves your firewall.

• 49:55Andrew Giancola?

  To see optimized action, head describe.how/pfp and mention PFP for a 30-day risk-free trial. That's S C R I B E dot H O W slash P F P. If you've heard any recent episode of Health Corner, you know that I have spent the last few years trying to optimize my sleep. I've tried sleep trackers, cooling my room, changing my nighttime routine, all the different things, but nothing really matters as much as having the right mattress. And that's one of the reasons I love Lisa. A great mattress is one of those things that you use every single night and you spend a third of your life sleeping. And it can make Huge difference on how you feel the next day.

• 50:39Andrew Giancola?

  Leesa has mattresses designed for different sleep positions and comfort preferences. And their sleep quiz can help you get matched in less than two minutes. Plus, they're designed and they're assembled in the USA and they come with free shipping, easy returns and a 120 night free sleep trial. So go to leesa.com for up to 30% off mattress plus and get an extra $50 off with promo code PFP. Exclusive for my listeners. That's L E E S A dot com promo code PFP for 30% off mattresses plus an extra $50 off. Let them know we sent you in the survey after checkout. Leesa.com promo code PFP.

• 51:22Andrew Giancola?

  So you mentioned recently that you've taken optimization too far. Can you tell us that story and what happened?

• 51:29Speaker 02

  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? There 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, what are, 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? Are you going to look if you have card linked offers?

• 52:13Speaker 02

  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

• 52:56Speaker 02

  this thing got delayed and now we weren't able to make the recipe we wanted. And 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

• 53:36Speaker 02

  driving around for Uber, DoorDash, Lyft, Instacart, whatever your, you know, 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. So 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, 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.

• 54:21Speaker 02

  And it feels like time is the limited resource and it's easy for us to all say that, of course it is. But to start acting on its behalf is really tough.

• 54:30Andrew Giancola?

  And I think that's one thing that you and I, you know, we were in our twenties, 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 to having kids and stuff like that, you see how valuable time truly is because you have way less of it. And 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.

• 55:12Andrew Giancola?

  But I think that's just part of life and it's part of growing and as time goes on when it comes to that timeframe. So what is the biggest win that you have ever had from playing the points game?

• 55:21Speaker 02

  Hmm. It feels ridiculous to say this, but there have just been so many memorable trips that 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. I 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

• 56:02Speaker 02

  two seats opened from SF to Paris, nonstop and 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, 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. And 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

• 56:45Speaker 02

  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. And so we chased 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, 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

• 57:26Speaker 02

  and miles. It wasn't necessarily the best value, but it unlocked the coolest experience. Now, 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. And to do that was to play this game. And so we were able to reduce our travel cost every year to a very nominal

• 58:10Speaker 02

  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.

• 58:35Andrew Giancola?

  And that's the biggest difference for a lot of people out there is that when you try to figure out which way you want to go, if your goal is not to travel, if that what brings you value, if that's not part of your dream life, then really cash back 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 sign up bonus?

• 58:54Speaker 02

  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. So 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.

• 59:36Speaker 02

  And it's not like you sync your gift cards. So it was like, one month, we spent $4,000 on groceries. And 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.

• 1:00:14Andrew Giancola?

  I feel like I'd be the type of person that would just overspend on the gift cards. It's like free money, you know, 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?

• 1:00:37Speaker 02

  I actually got an email from someone that was a really good example of this. They'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? Like, 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.

• 1:01:20Speaker 02

  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. So 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.

• 1:02:03Speaker 02

  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 grand. But if I bought a different flight, it was only 2 grand. And you can do this at any scale. You could say the flight was 1,000, but if I took this Southwest flight, it's only like $300. 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 $5,000 ticket. But I could book another airline and it's $800. So like, just book the other airline. And that's a case where maybe you just booked that $800 flight in the travel portal. I'm not upset with that. Like, I want you to travel. I want you to get out there. But sometimes you can learn how the game works so much

• 1:02:48Speaker 02

  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 of 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. So 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.

• 1:03:31Speaker 02

  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, even though I know how this game works and I've been able to get really outsized value. Friends who just play cash back and they just buy tickets. I'm jealous of the simplicity of it. There'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.

• 1:04:14Andrew Giancola?

  For sure, there is a balance. You could over optimize and have blinders on to 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?

• 1:04:29Speaker 02

  I can only have one. I would say I'm going to have a run on sentence mindset 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% of value that might not be worth it. So 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.

• 1:05:11Speaker 02

  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? Do 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.

• 1:05:54Speaker 02

  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.

• 1:06:12Andrew Giancola?

  For 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?

• 1:06:19Speaker 02

  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 allthehacks.com/email and I just share all the top deals, points, everything that's happening this week. The 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

• 1:07:03Speaker 02

  find it and enjoy and let me know what you think.

• 1:07:06Andrew Giancola?

  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.

• 1:07:12Speaker 02

  Sounds good. Thanks for having me.