How to Spend Your Miles & Credit Card Points — Deal Master Chris Hutchins Explains

1. 0:00 – 0:51

   Start/preview

   1. CHChris Hutchins0:00

      San Francisco to Tokyo in economy on June 5th, 37,000 points. 37,000 points, if you redeem them for Amazon gift cards, might get you $222.

   2. TFTim Ferriss0:12

      That's nuts. What are the other tools that you would recommend?

   3. CHChris Hutchins0:15

      PointsYeah. You go to the Daydream Explorer feature, and they just give you a map of the world, and you say, "Hey, I wanna go to a beach in first class from the United States. Take me there."

   4. TFTim Ferriss0:29

      Mm-hmm.

   5. CHChris Hutchins0:29

      It'll be like, "Oh, well, did you know that this summer I could go to Lisbon for 45,000 points, but not in coach, in business class?"

   6. TFTim Ferriss0:36

      Mm-hmm.

   7. CHChris Hutchins0:37

      So you wanna go to Lisbon in business class for what Amazon equivalent would've been, like, $275. You know, anyone listening probably knows you're not finding $275 business class tickets to Europe in the summer.

   8. TFTim Ferriss0:50

      And there it is.

2. 0:51 – 5:01

   Coping with a Frankenstein’s Monster of travel points.

   1. TFTim Ferriss0:51

      So Chris, as the caffeine's hitting my bloodstream, and we can treat this as a warm-up. Who knows? It'll might make it into the final cut. The goal here, multifold, so shall we call it goals, is to figure out what on earth I should do with my Frankenstein of points and miles and so on that I've accumulated over my adult life since college, basically.

   2. CHChris Hutchins1:18

      Yep.

   3. TFTim Ferriss1:19

      That's one. The other is to make sure that it doesn't get into the conversation such rarefied air that people are just like, "Wow, this is a great conversation for the .001%."

   4. CHChris Hutchins1:30

      Yep.

   5. TFTim Ferriss1:30

      Right? Which I actually don't think we're at too great a risk of because, and we'll get to the total tally and so on, effectively, as soon as I began starting businesses, I put everything on my cards.

   6. CHChris Hutchins1:45

      Yep.

   7. TFTim Ferriss1:45

      So advertising, monthly spend, trade shows, anything and everything that I could put on the cards, I put on the cards. And you, of course, are a nth degree black belt in the Jedi arts of points and various types of arbitrage and trade and just general skullduggery. Excuse me. Not skullduggery. I just had to use that because Mike Tyson likes that word. [laughs] And there are levels, and then there are levels, right? I would like to think of myself as pretty aware of how to find shortcuts here and there, and it's not really shortcuts that we're looking for, but kinda clever, elegant, not just techniques, but hopefully we'll get to some principles overall that will allow people to deal with what I think is a very common headache because, in my case, I've accumulated all this stuff, and every time I look at my points, and we're gonna get to some of your shenanigans in a second 'cause I want to hop straight to a couple of real-life examples that seem insane. And people look at these points, I look at these points, and I'm like, "Number one, I have no idea what to do with these. Number two, I assume they're basically worthless. Number three, I feel like I've lost a sucker's game every time I look at them." Does that make sense?

   8. CHChris Hutchins3:12

      Yep.

   9. TFTim Ferriss3:12

      That I've sort of signed up for a game that in the end it's like wandering through a casino. The house always wins. And for all of those reasons, plus just the general brain damage of trying to figure out what to do, and do they make it difficult like an insurance claim? [laughs] Whatever. I haven't really put a lot of effort in. Every couple of years I'll put a few hours in and I'm like, "Too hard, too complicated. Don't wanna deal with it." And then I exit the side door, and then I'm right back to where I am-

   10. CHChris Hutchins3:45

       Yeah

   11. TFTim Ferriss3:45

       ... today looking at this balance of points and stuff. So that's my confessional part one. But let's [laughs] start. There's so many different places to start. So I'll let you choose. And I think it's fair to say for the record, and you've been very transparent about your finances and stuff, it's not like you're driving around in a fleet of Bugattis, a different color for every day of the week, that you have a private hangar of 17 jets. Like, that's not your life. You've done very well, and I don't know if it was at the same time prior to or after we recorded that mega-marathon on podcasting. You wanted to ask me a bunch of questions, and so I was like, "Hey, let's just record it." But you've gone full time in the All the Hacks ecosphere. I guess this is all to say I'm trying to set a reference point for people listening for you, right? Because they might assume that you're like Kevin, as in Kevin Rose, or that you're a venture capitalist, or that you have tens of millions, hundreds of millions of dollars, and therefore the numbers that I'm about to give they might discount. And I'll just throw those out, and then you can take this tangled mess of an introduction and do with it what

3. 5:01 – 6:56

   How Chris became obsessed with arbitrage.

   1. TFTim Ferriss5:01

      you will. So you bought 300K worth of gold at Costco in the past year.

   2. CHChris Hutchins5:06

      [laughs]

   3. TFTim Ferriss5:07

      And I'm like, "Wait, what? You could buy gold at Costco," first of all, and then there's the amount. And then I was asking you about [laughs] Amazon-related arbitrage, and you're like, "Yeah. Well, that's fair game, but it doesn't really happen or work anymore, but I did buy $1 million of gift cards in January, 1.02 million to be precise." And I'm like, "What the hell?" Okay. So that is one of the messiest on-ramps I've ever offered a guest, but why don't you take that? I think you understand the intention behind it, which is like-

   4. CHChris Hutchins5:41

      Yeah

   5. TFTim Ferriss5:41

      ... let's give some crazy examples, and let's also ground in reality kind of who you are so these numbers are able to be put into some kind of context.

   6. CHChris Hutchins5:51

      I think that the, the easiest way to explain both those stories and who I am in kind of a very concise way is that I really like the arbitrage of anything.

   7. TFTim Ferriss6:02

      Mm-hmm.

   8. CHChris Hutchins6:02

      And, you know, I kinda grew up in the, you know, maybe upper middle class, middle class But I went to a private school, and my parents didn't give me money.

   9. TFTim Ferriss6:09

      Mm-hmm.

   10. CHChris Hutchins6:10

       Right? They weren't like, "Here's my credit card," like many people I knew did. I was always like, how do I kind of keep up with the Joneses per se, but like I didn't have a credit card to take debt out on. Like, there were no other options. So-

   11. TFTim Ferriss6:22

       Hmm

   12. CHChris Hutchins6:22

       ... you know, I was finding these arbitrages early when I was like, "Oh, kids like pizza. I want pizza. I don't have money for pizza. Let's order pizzas to school, sell slices, and eat my profit so I get free pizza every night."

   13. TFTim Ferriss6:35

       [chuckles]

   14. CHChris Hutchins6:35

       It was kind of like I've always been thinking in the back of my head, "How do I do the thing that everyone else with all this money and all these resources does? How do I get to do that even though I don't have the resources?" And so that's been my-

   15. TFTim Ferriss6:47

       Mm-hmm

   16. CHChris Hutchins6:47

       ... MO for life is I don't wanna sacrifice, but I also don't wanna go into debt, you know, or just spend money I don't have.

4. 6:56 – 12:11

   Flipping gift cards for fun and profit.

   1. CHChris Hutchins6:57

      So you mentioned gold, you mentioned gift cards. The gift card thing was interesting because as is sometimes the case with venture-backed startups, companies are willing to take investor money and sell things at a loss and lose money to grow. And there was this weird window late last year, early this year, where there were ways that if you were creative, you could buy gift cards at a huge discount.

   2. TFTim Ferriss7:22

      Gift cards to where? What kind of gift cards?

   3. CHChris Hutchins7:25

      There was an app called Pepper.

   4. TFTim Ferriss7:27

      Okay.

   5. CHChris Hutchins7:27

      And they were selling gift cards for a discount in a convoluted way. They'd be like, "Well, you could buy Amazon gift cards. You could get a $500 Amazon gift card for $500, and then we're gonna give you 30X points in 14 days that you can redeem for other gift cards." But they were holding the best deals for the biggest spenders, so like the average consumer wasn't getting the best deal. And I just realized that I don't necessarily wanna take on the risk of if this company goes under, they owe me 20, 30, 40, $50,000 worth of points. But there were lots of people that did, and they didn't want Amazon gift cards, so they were willing to sell them at a loss. Or not at a loss, at a, at a break even.

   6. TFTim Ferriss8:08

      Mm-hmm.

   7. CHChris Hutchins8:08

      They were like, "I'll buy Amazon gift cards for what at the end of the day will be 20% off, and I'll sell them for 18% off."

   8. TFTim Ferriss8:16

      Mm-hmm.

   9. CHChris Hutchins8:16

      And I was like, "I could do much better trying to arbitrage that than take on a lot of risk."

   10. TFTim Ferriss8:22

       Mm-hmm.

   11. CHChris Hutchins8:22

       I, I literally sent an email out to my list and said, "Hey, who wants to buy gift cards?" And I set up an e-commerce site, and we were selling Amazon gift cards at 10% off.

   12. TFTim Ferriss8:30

       [laughs]

   13. CHChris Hutchins8:31

       Now, who doesn't want 10% off Amazon?

   14. TFTim Ferriss8:32

       [laughs]

   15. CHChris Hutchins8:33

       Why not? But I could buy the Amazon gift cards for somewhere, depending on the day, between like 12% and 15% off. And so people were stoked getting 10% off Amazon.

   16. TFTim Ferriss8:43

       Mm-hmm.

   17. CHChris Hutchins8:43

       I was stoked 'cause I was making a little bit of a profit. But even better, I could buy all those Amazon gift cards from people with a credit card. So I spent a million dollars. I probably made, you know, 2 million points buying those million dollar of gift cards, and then a little bit of profit on top of that. And then everyone that bought them was like, "I'm saving money on Amazon." So it was a total win-win-

   18. TFTim Ferriss9:05

       [laughs]

   19. CHChris Hutchins9:05

       ... because there was this rare moment where gift cards were selling at ridiculous prices.

   20. TFTim Ferriss9:10

       [laughs]

   21. CHChris Hutchins9:11

       And that's still true today, maybe not as ridiculous. But just so people don't think, "Oh, I missed the boat. This is never possible," anyone that has a credit card, whether it's Amex or Chase, there's all these parts of the website where it's like, "Here are some of the special offers you, you have on your card."

   22. TFTim Ferriss9:28

       Mm-hmm.

   23. CHChris Hutchins9:29

       And earlier this year, Amex had one where it was spend $200 at Lowe's, get $50 back. I don't need anything at Lowe's, but I had that offer on seven different cards. So I took my daughters, we went to Lowe's, we bought seven $200 gift cards to Dick's Sporting Goods, and then we just resold them for like 91 cents on the dollar. But because we were getting 50 off each $200 purchase, we were buying them for 75 cents on the dollar.

   24. TFTim Ferriss9:55

       [laughs]

   25. CHChris Hutchins9:56

       That kind of stuff happens all the time. And so anytime I see something that's extremely on sale, I think, "How can I make money?"

   26. TFTim Ferriss10:03

       Yeah. So let me hop in here for a second because I imagine there are some people who are like, "I'm definitely gonna do that," who are listening. And then there are people who may be cut from a similar cloth to myself, and this is part of the reason why before we started recording, I said, [chuckles] "Chris, let's get to unraveling the mysteries of the universe," because I realized, much like someone said to me long ago, they said, "If you wanna understand somebody, talk to them about money and talk to them about sex." But like once you get into arbitrage and time and value, it kind of opens Pandora's box to everything, [chuckles] right? Philosophically speaking, your beliefs about the world. [chuckles] That might sound like a grand statement, but here's where I'm going. There is a religious war afoot. You guys may have seen it in the news. I'm not talking about the Middle East. I'm talking about personal finance, where you have [chuckles] ultra frugality on like one end of the extremism, let's just say, like super, super reusing cotton balls type stuff. And then you have on the far other end, maybe where I'm perhaps a little bit closer, folks who are like, "Just make more money," because the upside is unlimited, uncapped in a sense, whereas you could only save so much money. But what I'm hoping for today is that we'll explore kind of the whole spectrum, right? Because much in the way I'm gonna take a lot of positions in this conversation. Right now I'm gonna be your defense attorney. And the reason I say that is that for you, it's turned into your sport. It started off as kind of a survival arbitrage mechanism to keep up with the Joneses, right?

   27. CHChris Hutchins11:44

       Yep.

   28. TFTim Ferriss11:45

       And then it's become kind of a professional sport that you play at the highest level, much like if I go to Uzbekistan, which I did long ago, I might try to learn Uzbek, but like for most people, that's fucking ridiculous. Like you'd never wanna learn any Uzbek. It's a total waste of time, but like that's my sport, right? So with all that said, let's talk about the gold, and then I have some maybe opening questions that we can, that we can get into. So

5. 12:11 – 17:36

   The mechanics of Costco gold arbitrage.

   1. TFTim Ferriss12:11

      what's the story with Costco gold?

   2. CHChris Hutchins12:13

      So Costco sells a tremendous amount of gold. I can't remember the stats, but it's gotta be on the order of hundreds of millions of dollars, I guess, of gold. And it's kinda funny because sometimes you'll check out a Costco and it'll be like, "Do you want this gold bar? It's $3,300."

   3. TFTim Ferriss12:28

      [laughs]

   4. CHChris Hutchins12:29

      And it's, like, more than anyone would normally spend on groceries at all. Now, the crazy thing about Costco is that if you have a Costco Executive membership, so they have two tiers, 65 and $130, at the Executive level, they give you 2% cashback on everything you spend at Costco-

   5. TFTim Ferriss12:45

      [laughs]

   6. CHChris Hutchins12:46

      ... up to $62,500 a year. Which for a normal-

   7. TFTim Ferriss12:50

      Okay

   8. CHChris Hutchins12:50

      ... person is, like, plenty of cashback.

   9. TFTim Ferriss12:52

      Yeah. I think I see where this amount of gold is coming from. [laughs] Okay.

   10. CHChris Hutchins12:55

       Yeah. But when they sell gold, they don't have a dynamic price. They say, "Today gold is 3,329.99." And the gold market changes throughout the day. There are times where when you're at Costco, if you look up online, would buying this gold bar and selling it, what would be the, the margin? And I would say you almost never make money. Costco is not selling gold at a price that you could flip it for a profit. But they are giving you 2% back, and very often that 2% back makes up the loss you would take reselling it.

   11. TFTim Ferriss13:29

       Hmm.

   12. CHChris Hutchins13:30

       And you can buy things at Costco with cash, you could buy things at Costco with a debit card, and you could buy things at Costco with a credit card. So, you know, if you were to buy $100,000 of gold and you didn't lose money, you could still keep the points you got from that transaction. But I'd actually argue that if you time it right, you can also make money-

   13. TFTim Ferriss13:48

       Hmm

   14. CHChris Hutchins13:49

       ... on the spread because sometimes that spread might be half a percent, and Costco's willing to give you 2% back, and so that one and a half percent can be profit.

   15. TFTim Ferriss13:57

       [laughs] Okay. Got it. So the 300,000-plus of gold basically was hitting the upper maximum of what you could get-

   16. CHChris Hutchins14:06

       Yes

   17. TFTim Ferriss14:07

       ... in terms of cashback.

   18. CHChris Hutchins14:08

       When I'm sitting at the checkout counter at Costco, I'm like, "Okay, gold's this price." I look at my phone and I say, "Okay, what could I sell this gold for? Okay, I could make a profit selling it. Forgetting even points, I could just make a profit selling this gold. Okay." R- ring up the Costco groceries, total's 180 bucks. Could you please add five, which is the limit, five $3,500 bars? And they're like, "Really? Oh, okay. Your total now instead of $180 is, like, $15,180." [laughs] And then a- assuming you have a card with the right limit and your bank's not gonna decline a $15,000 transaction, tap to pay, thank you Apple for the simplicity, and, and then I literally sell it before I've left the store. Like, I'm not trying to invest in gold.

   19. TFTim Ferriss14:49

       Now, that's my question. Okay, so the gold is not solid bars sitting in a shopping cart because you [laughs] there would just be, there would just be people hanging outside.

   20. CHChris Hutchins15:00

       No, you get f- five bars.

   21. TFTim Ferriss15:02

       You do?

   22. CHChris Hutchins15:02

       Yep.

   23. TFTim Ferriss15:03

       Okay.

   24. CHChris Hutchins15:03

       I wish I had them here. I have a rack that holds them. But as an example-

   25. TFTim Ferriss15:06

       [laughs]

   26. CHChris Hutchins15:08

       ... this is a rack from Pamp, which is a Swiss company that just holds bars. So this rack probably holds 20 bars of gold, one ounce bars.

   27. TFTim Ferriss15:16

       Okay. All right, hold on. So I guess there are two questions. So do you just basically, like, keep one hand on your concealed carry, which is probably not something you can do in California, but then you take, like, a loop around the store with your shopping cart full of gold and then return it to the store? When you say you've sold it before you leave the store, what do you mean by that?

   28. CHChris Hutchins15:39

       Sorry. So what I mean is I've gone in and I've locked in the price.

   29. TFTim Ferriss15:43

       Yeah.

   30. CHChris Hutchins15:43

       I did a whole episode, by the way. If someone, like, wants to go really deep, the guy who runs the marketplace Pure, collectpure.com-
6. 17:36 – 20:27

   Using AwardTool for finding point deals.

   1. TFTim Ferriss17:36

      for people who are wondering, because you may not have Chris as a friend who's willing to do this on your podcast, we are gonna discuss how you can find low lift approaches or sort of time efficient approaches to exploring a lot of this stuff. For instance, there was a website you recommended, Chris. I know we're hopping all over the place, but I had never even heard of it before. I put it in my newsletter and I'm blanking on the name.

   2. CHChris Hutchins18:03

      AwardTool.

   3. TFTim Ferriss18:04

      Yeah. So could you describe what this is? Because it's very straightforward, and it was simply off my radar of awareness. So what is this?

   4. CHChris Hutchins18:14

      If we zoom, zoom back a while, I think we live in this world where- Credit card points are easier to get than they've ever been. If we go way, way back in history, it's like they didn't exist, then you could get one per dollar, and now it's, depending on where you purchase, you could get five points per dollar. You can get 100,000 points when you open a card. And then we were in this weird area for a few years where it was like, well, there's lots of them, but it's very difficult to use them because to get the most value, you have to know all the kinda Jedi mind tricks, if you will. And then a couple companies came out and said, "Hey, we're just gonna build tools that are as simple as Google Flights that make it really easy for you to find ways to get real value out of your points." So there's two sites. There's probably like five or six. I'll give the, the three that I like and how they're slightly different.

   5. TFTim Ferriss19:03

      Okay.

   6. CHChris Hutchins19:03

      There's really two things you might want in this world if you're trying to use your points. One is inspire me and give me the best deal, and one is help me find the best way to get from A to B.

   7. TFTim Ferriss19:16

      Mm-hmm.

   8. CHChris Hutchins19:16

      AwardTool, which is the one you talked about, I think is better for the person who's like, "I wanna go to Japan. I have a few days of availability that I could explore. I could go a couple days earlier, a couple days late, but ultimately I wanna go to Japan."

   9. TFTim Ferriss19:30

      And that's just AwardTool.com?

   10. CHChris Hutchins19:32

       AwardTool.com. So you could say, "Hey, I'm going from San Francisco to Japan," or you could even say, "San Francisco to Asia, and I wanna go in this window." And it'll come back and say, "Here are the best deals." And you could filter them and say, "Hey, I only want nonstop. I only wanna fly in business class," or, "I only have points with Amex, so don't show me other options."

   11. TFTim Ferriss19:54

       Mm-hmm.

   12. CHChris Hutchins19:55

       And you get these things where right now from San Francisco, and I just looked at Asia, but here, San Francisco to Tokyo in economy on June 5th, 37,000 points plus $11 in taxes and fees. 37,000 points, if you redeem them for Amazon gift cards, might get you, I don't know, I think it's s- point $0.60. So $222. It is rare that you will find a flight to Japan, even in economy, for $220.

   13. TFTim Ferriss20:24

       Yeah. That's nuts. Okay, cool. That's the equivalent I was

7. 20:27 – 22:31

   Daydream exploring with PointsYeah.

   1. TFTim Ferriss20:27

      looking for. What are the other tools that you would recommend?

   2. CHChris Hutchins20:30

      The other one that I like is called PointsYeah.

   3. TFTim Ferriss20:32

      Yeah? Like Y-

   4. CHChris Hutchins20:35

      E-A-H. PointsYeah.

   5. TFTim Ferriss20:37

      [laughs] Okay, got it. [laughs]

   6. CHChris Hutchins20:39

      You go to the Daydream Explorer feature, and they just give you a map of the world, and you say, "Hey, I wanna go to a beach in first class from the United States. Take me there."

   7. TFTim Ferriss20:51

      Mm-hmm.

   8. CHChris Hutchins20:52

      It'll be like, "Oh, well did you know that, you know, if you wanna go to this place, it's only this much." So this summer I could go to Lisbon for 45,000 points, but not in coach, in business class.

   9. TFTim Ferriss21:03

      Mm-hmm.

   10. CHChris Hutchins21:04

       So you wanna go to Lisbon in business class for what Amazon equivalent would've been, like $275. You know, anyone listening probably knows you're not finding $275 business class tickets to Europe in the summer.

   11. TFTim Ferriss21:17

       Yeah. And there it is.

   12. CHChris Hutchins21:19

       I like that from more of a inspire me. It's like I don't know where I wanna go, I don't know when I wanna go. At the end of the day, I would say the more flexibility you have, the more your points will take you way, way further.

   13. TFTim Ferriss21:30

       Yeah.

   14. CHChris Hutchins21:31

       If you come to me and say, "I need to be in Japan, and I need to take this one Japan Airlines flight, and I need it to be on this specific day, what can my points get for me?" Might not be more than you would get just booking the flight on the Amex, Chase, Capital One, et cetera portal.

   15. TFTim Ferriss21:47

       Yeah, so let me hop in here.

   16. CHChris Hutchins21:48

       Yep.

   17. TFTim Ferriss21:48

       So that's the conversion. You mentioned a few things, right? That kinda underscore what makes this whole game attractive to a muggle like me who has not had the inclination, still doesn't really have the inclination to get really deep in the weeds, right? It's like $222 flight [laughs] to Japan, $270 business class flight to Europe in the summer. Like, yeah, of course I wanna do that. I [laughs] grew up being super ultra, ultra frugal, right? So that hardwiring is still there. So as financial savings catnip, like, that is very, very attractive. I hate wasting money. I still way overeat because I'll save leftovers and stuff 'cause I don't wanna waste food. I mean, I'm still that guy who will pack up

8. 22:31 – 27:22

   Why modern airlines rely on loyalty programs to survive.

   1. TFTim Ferriss22:31

      everything. But this has seemed very complicated, so I'm hoping you can help us uncomplicate it. Before we get there, well, let, let me give people a snapshot, right? So you have, through all of your various techniques and tricks and this, that, and the other thing, 22.8 million points, right?

   2. CHChris Hutchins22:52

      Yeah.

   3. TFTim Ferriss22:52

      Something like that. And what is my total at the moment, roughly?

   4. CHChris Hutchins22:59

      I think you're at 15.5.

   5. TFTim Ferriss23:01

      Yeah, so it's 15.5 million. Keep in mind, guys, this is for the last 24 years, right? [laughs] And I've also frittered some of it away using Amex points to buy stuff on Amazon and so on, which would get me a, a heavy ruler on the back of the hand from, from Dr. Chris. [laughs] But we'll get to that. Just a few more factoids. I have not fact-checked this, so I'm relying [laughs] on, on Christopher. But how significant are loyalty programs to airlines?

   6. CHChris Hutchins23:35

      There's a really great video if you wanna go deep on this. I'll give you the kinda high level on both loyalty programs to airlines, which is kinda frequent flyer miles.

   7. TFTim Ferriss23:44

      Mm-hmm.

   8. CHChris Hutchins23:44

      And it's the craziest thing I think I've ever come across when understanding business.

   9. TFTim Ferriss23:50

      [laughs]

   10. CHChris Hutchins23:51

       And it's that the market cap of the major three airlines, American, United, and Delta, meaning the total value of the company, they all have a market cap between $6 and $20 billion. The market cap of the loyalty point program explicitly, not the airline, but just the subsidiary of it, ranges, depending on the airline, from $22 to $26 billion. So the loyalty programs are worth more than the airline itself.

   11. TFTim Ferriss24:20

       [laughs]

   12. CHChris Hutchins24:21

       And if you actually back out So everything that is United that is not the loyalty program is worth negative $12 billion.

   13. TFTim Ferriss24:28

       [laughs]

   14. CHChris Hutchins24:30

       There's this common understanding in this kind of points, miles, airline world that airlines really exist to be effectively banks for their miles and points, and then they just have to fly these planes all around the world so that that bank can continue to operate. Because-

   15. TFTim Ferriss24:46

       [laughs]

   16. CHChris Hutchins24:46

       ... you know, Delta came out and said, I think it was a year ago, they said in 2023, 1% of US GDP went through a Delta Amex card.

   17. TFTim Ferriss24:56

       [laughs]

   18. CHChris Hutchins24:57

       The transaction volume on Delta Amex cards was 1% of GDP, or, or I think they said just shy of 1% of GDP. They didn't give an exact number.

   19. TFTim Ferriss25:05

       Yeah. [laughs]

   20. CHChris Hutchins25:05

       So every time Amex is awarding these Delta miles, every time you're using your Chase points to transfer to United, they're effectively selling those points to those banks so that they can give them to the cardholders. The business of selling those points is massive.

   21. TFTim Ferriss25:21

       Yeah.

   22. CHChris Hutchins25:22

       And the profit margins of an airline, just the airline part of it, are like laughably small. I think the average profit per passenger for US airlines on average is $10, and I think American Airlines was the bottom. It was the profit per passenger per year on American is $3.40.

   23. TFTim Ferriss25:40

       [laughs] So if you're wondering why they shill those credit cards so hard over the loudspeakers while you're trying to watch your movie in peace, this is why.

   24. CHChris Hutchins25:49

       Yeah.

   25. TFTim Ferriss25:49

       Right?

   26. CHChris Hutchins25:49

       United Airlines sold almost $4 billion worth of miles a- as part of their business. This is a, a little old data, but back in 2019, it's probably only gone up from that. And if anyone remembers during the pandemic, the, like airlines were hurting. Nobody was traveling, and so in order to survive, they had to mortgage... They had to basically raise money, and they couldn't put the airline up, so they, all three airlines, put their loyalty programs up. That was the collateral.

   27. TFTim Ferriss26:19

       [laughs]

   28. CHChris Hutchins26:19

       And raised, depending on the airline, like $6 to $10 billion each using the loyalty program as their collateral.

   29. TFTim Ferriss26:25

       [laughs] Okay. This is one of the many reasons, right, hearing facts like this where I'm like, "This is a trap. If I enter into the labyrinth, there's a reason why these are so profitable [laughs] for these companies, and it's not because the person collecting the miles automatically wins," [laughs] right? It can't be.

   30. CHChris Hutchins26:43

       No.
9. 27:22 – 30:29

   Different kinds of points and how to optimize them.

   1. TFTim Ferriss27:22

      So Chris, what would you suggest we do in terms of exploring what I should do with my points? And we're always gonna bring this back-

   2. CHChris Hutchins27:30

      Yep

   3. TFTim Ferriss27:30

      ... to what people can use. I think people will pick up a lot. We can also sprinkle in some crazy points stories, but I think we've given enough of a taste of that, that we can kinda look at the actual nuts and bolts of like-

   4. CHChris Hutchins27:43

      Yep

   5. TFTim Ferriss27:43

      ... what do you do? I'm looking at this printout and I'm like, [inhales] makes my head hurt just to look at all these airlines with all the points, right?

   6. CHChris Hutchins27:52

      We'll break the landscape into... There's two obvious buckets that people are gonna be familiar with. You have airline miles that are linked to a program.

   7. TFTim Ferriss27:59

      Yep.

   8. CHChris Hutchins27:59

      So you have some Alaska, some American, some Delta, and some United. Four major US carriers.

   9. TFTim Ferriss28:05

      Yep.

   10. CHChris Hutchins28:06

       You've got hotel points. I'm not gonna tell you what to do with yours because they all expired. [laughs]

   11. TFTim Ferriss28:11

       Got some international airlines, but whatever.

   12. CHChris Hutchins28:13

       And then you have bank points, and I'm gonna call them transferable points, and the thing that I really like about transferable points, just to set the difference in people's mind and why the kind of street value is higher, is that American Express-

   13. TFTim Ferriss28:29

       Let me pause for a second just to say, right, like by bank?

   14. CHChris Hutchins28:33

       Yeah. American Express, Capital One, Citibank-

   15. TFTim Ferriss28:36

       Yep

   16. CHChris Hutchins28:36

       ... Wells Fargo now, Chase. Amex will let you move your points to 18 different airlines. So you can move your Amex points to Delta, you can move them to Air France, you can move them to Air Canada. The reason why people love them is when we go back to these tools and you're searching, "Gosh, I wanna find a good deal to Europe," well, sometimes that good deal might be a deal with Air France.

   17. TFTim Ferriss28:58

       Mm-hmm.

   18. CHChris Hutchins28:59

       Sometimes that good deal might be a deal on United, but it's an even better deal if you book it through Air Canada, which is a partner of United. When you have the flexibility to take your points and put them anywhere, not anywhere, but to 18 different airlines or five different hotel programs, it just increases the likelihood that you will find a good deal. So I love accumulating transferable points because it just spreads out the surface area of places you can find deals.

   19. TFTim Ferriss29:24

       Yep.

   20. CHChris Hutchins29:25

       That said, the best value that anyone's gonna find from their points and miles is on this kind of aspirational travel, meaning long-haul international business and first class, luxurious five-star hotels and resorts. Because airlines, wh- while this is a shift, they haven't fully shifted to the point that a business class ticket might cost 10 times the dollars, but it might only cost two times the points.

   21. TFTim Ferriss29:54

       Hmm.

   22. CHChris Hutchins29:54

       And a really nice luxury resort might be 10 times the cost of a Holiday Inn downtown.

   23. TFTim Ferriss30:01

       Right, if you're paying in dollars.

   24. CHChris Hutchins30:02

       But it might only be three or four times the cost in the number of points you'd need. That's where you're gonna get the most value.

   25. TFTim Ferriss30:10

       Mm-hmm.

   26. CHChris Hutchins30:10

       That doesn't mean that if you're someone who's only traveling domestically, you can't find good value, because there are a lot of cases where you're flying between small airports, you're flying during the holidays, you're flying last minute, and you'll see a flight where it's just astronomically expensive for what it should be, and it's a great deal with

10. 30:29 – 32:05

    Hoard or spend?

    1. CHChris Hutchins30:29

       points.

    2. TFTim Ferriss30:29

       I'm realizing, I guess, a couple of things that I'll ... throw out there to act as a stand-in for some listeners, right? So number one is that, and I want you to poke holes in this, or it can just be fodder for conversation because I'm realizing that our conversation is always, meaning the last handful of weeks at least, focused on what the hell should I do with all these points? Like staring at this just makes me feel like a sucker playing a sucker's game or someone with undone homework, and they expire, right? Which is ridiculous 'cause it's engineered.

    3. CHChris Hutchins30:59

       Some of them.

    4. TFTim Ferriss31:00

       Some of them expire. But I've realized that there's how to use the miles, and then there's how to accumulate them. Now, I have not focused on the accumulate 'cause by and large they seem like games I don't wanna play, and I think what's gonna be in the mind of a lot of folks, certainly why haven't I done this to date? Time, right? So the Amex is... Let's just say using the Amex on Amazon, it might be a bad trade on the value per point if I assume my time is worth $0, right? But if it takes me an hour to do something to get a bunch of stuff organized to find a better value per point, it could be a Faustian bargain if my sort of value of time per hour is high enough, right? So that's always been sort of the crux of the challenge for me. And also, I should say, just for people listening, we can assume that my hotel points are usable even though they've expired, if that is in any way informative to the conversation. And

11. 32:05 – 35:34

    Creative uses for large point balances.

    1. TFTim Ferriss32:05

       also, I just want to explain one of the motivations for reaching out to you was not just how do I use these points, but, like, is there anything crazy I could do with these points? And I'm not convinced there is, and there may be things that I can do that seem crazy that are just a poor use of points, right? But I was like, okay, I realize I could use some of this for travel, but I can also afford to pay for travel, which doesn't mean I should pay dollars instead of points if I'm just looking at the kind of value per point. But is there something big and nutty I could do? Like one trip where I just blow all of these points. [laughs]

    2. CHChris Hutchins32:46

       Right. Let's start there because I think the reason why the points game is exciting in the first place is that it feels like it's free.

    3. TFTim Ferriss32:58

       Right.

    4. CHChris Hutchins32:59

       Now, I could poke a hole in that and say, if you just used a cash back card the entire time, instead of having 12 million points, you probably would've been sitting on $300,000.

    5. TFTim Ferriss33:09

       Right.

    6. CHChris Hutchins33:09

       Depending on the card you were using. And if someone had done that, they would probably feel very differently about taking $300,000 they've saved and blowing it with no regard.

    7. TFTim Ferriss33:21

       [laughs]

    8. CHChris Hutchins33:21

       Whereas if they had 12 million points-

    9. TFTim Ferriss33:23

       Yeah

    10. CHChris Hutchins33:23

        ... that in their mind, you know, could not fund their kids' education, pay their mortgage, et cetera, why not blow it on some wild vacation or something else? So there's this psychological element of I've earned these things. They are not dollars. Why not spend them flying Emirates first class, taking a shower in the sky, you know, eating caviar and sipping champagne? Why not do that? Because it's not like I'm dipping into my kids' college fund, where, where it might feel differently if they had earned cash back the whole time.

    11. TFTim Ferriss33:55

        Oh, it would feel totally differently. I wouldn't even do it necessarily. But those points are so constrained that it's like, okay, if the only place that I can use these is in, say, travel, it's like, well, they either never get used or they get used, but I can't apply them to paying off my mortgage or paying for my kids' college tuition, so.

    12. CHChris Hutchins34:16

        Yeah.

    13. TFTim Ferriss34:17

        YOLO.

    14. CHChris Hutchins34:17

        Now, I would say in the case of Amex, if you were like, "My time's too valuable to play this stupid game," I would say two things you could do. One, tell yourself or whoever books your travel to just book the travel using the points instead of using the dollars.

    15. TFTim Ferriss34:32

        Mm-hmm.

    16. CHChris Hutchins34:32

        And it's not gonna take any more work to go on Amex's site and say, "New York to LA, business class flight on United, book, checkout, pay with points instead of dollars," and you'd at least get your 1 cent. You could open up a brokerage account at Schwab or Morgan Stanley and open up one card that's the Morgan Stanley or the Schwab Amex, and you could just transfer all your points to your brokerage account.

    17. TFTim Ferriss34:55

        What does that do?

    18. CHChris Hutchins34:56

        Just turns it into dollars.

    19. TFTim Ferriss34:57

        Oh, I see.

    20. CHChris Hutchins34:58

        Depending on the card, what the rate is between 0.8 and 1.1 cents. But, like, there is a way that's better than Amazon to just dump them into a bank account where you don't have to think about it and you just have the money.

    21. TFTim Ferriss35:12

        Yeah.

    22. CHChris Hutchins35:12

        So I will say, like, that is an option, and for people for whom that feels like the better path, I would argue that they'd probably have been better off from the start just using a cash back card and getting 2.625%, which I think is, like, a good target cash back, and never having thought twice about points

12. 35:34 – 38:28

    Cash back card alternatives.

    1. CHChris Hutchins35:34

       at all.

    2. TFTim Ferriss35:34

       What's your current favorite cash back card if you had to pick one?

    3. CHChris Hutchins35:38

       US Bank launched this amazing 4% card. You had to put $100,000 in a brokerage account, and then they were like, "Oh, wow, this isn't profitable." [laughs]

    4. TFTim Ferriss35:46

       [laughs]

    5. CHChris Hutchins35:47

       Like, the amount of money that issuers get from swiping cards is not 4%. It's not even 4% before you pull the margin out for everyone along the way, and so that, that's gone. Robinhood has a card that's 3%, but I've heard some... You know, if you start putting too many business transactions on there, they have problems. The most scalable platform that I'm aware of for earning cash back at scale is the Bank of America... I'd say platform. If you have $100,000 with Bank of America or in a Merrill Lynch brokerage account, you effectively can earn 2.625% cash back on everything with their unlimited card, their travel rewards card, their premium rewards card. And if you have the premium rewards elite cards, it bumps up travel and dining spend to 3.5%.

    6. TFTim Ferriss36:40

       Mm-hmm.

    7. CHChris Hutchins36:41

       So everything you spend on travel and dining, 3.5% back. Everything else, 2.625% back. Obviously that assumes that you have the ability to put $100,000 in a brokerage account. You can just invest it in US treasuries. You can move over a Roth IRA. You don't have to have some Merrill Lynch broker manage your portfolio. But I would say that is the most scalable thing. You know, I know people with large limits can spend lots of money, don't have cards held up and transactions not post and points disappear.

    8. TFTim Ferriss37:13

       Mm-hmm.

    9. CHChris Hutchins37:14

       That I think is a, a solution. If you want something even easier, Fidelity has like a 2% cash back card.

    10. TFTim Ferriss37:19

        Mm-hmm.

    11. CHChris Hutchins37:20

        So if you're not earning 2% back on everything, I would say you're missing out. Everyone, I think if you want the simplest solution for everyone, you should say, "Am I at all flexible enough that I'll be able to get good use out of these points?" And by flexible, that doesn't mean I'm flexible in every vertical. You could be flexible that you could book a trip last minute. You could be flexible that you have to plan it super far in advance. You could be flexible with the destination, but not the dates. You could be flexible with what route you take, whether you go nonstop or not. So I'd say if you have any amount of flexibility, I think you could get a ton of value, and these tools have made it so much easier. Five years ago, I'd say, you know, it's tough. Now I'd say if you were like, "I wanna go to Europe this summer, and we wanna book it more than a month out, and we're kinda flexible where we go," you can get incredible value that will make a cash back card look like a poor return.

    12. TFTim Ferriss38:16

        Mm-hmm.

    13. CHChris Hutchins38:16

        But if every time you travel you're like, "I wanna fly on this date, I don't wanna change planes, and I wanna go to this city, and I wanna book it three months out, and I don't wanna have to think about it after that," you probably would be better off doing cash back the

13. 38:28 – 40:44

    Chris analyzes the value of my 12 million Amex points.

    1. CHChris Hutchins38:28

       whole time.

    2. TFTim Ferriss38:28

       Okay. So let's talk about what I should do with this printout that I'm looking at. It's not actually what I'll do with the printout, but what it represents, which is these various points that are scattered-

    3. CHChris Hutchins38:40

       Yeah

    4. TFTim Ferriss38:40

       ... across however many. Recognizing that Amex is kind of the 800-pound gorilla, right? That's where the vast majority are sitting.

    5. CHChris Hutchins38:48

       Yes.

    6. TFTim Ferriss38:49

       After looking at my full picture, we'll talk about, I guess, a couple things, right? So for people wondering, we're gonna talk about, like, what might I do with all this? What do the options look like that pass the sniff test by Chris? And then [laughs] understanding my, like, psychological profiling. And then also, if it could be done again, right? [laughs] What should I have done?

    7. CHChris Hutchins39:12

       Yep.

    8. TFTim Ferriss39:13

       [laughs] Right? So why don't you take us into the land of what might be done with this stuff, and the easiest way to do it.

    9. CHChris Hutchins39:22

       So I looked at all the points, and I would say if we focus just on the Amex points, it's the bulk of everything. It's a little bit easier to tell a story.

    10. TFTim Ferriss39:31

        Yep.

    11. CHChris Hutchins39:32

        You got 12 million Amex points. The easiest thing, you could spend them on Amazon. They'd be worth $85,000, right?

    12. TFTim Ferriss39:38

        Yep.

    13. CHChris Hutchins39:39

        You could just book flights. They'd be worth $120,000.

    14. TFTim Ferriss39:42

        Can you just repeat this again? All right. Use them on Amazon.

    15. CHChris Hutchins39:45

        $85,000.

    16. TFTim Ferriss39:45

        12 million, 85K. All right, got it. Then?

    17. CHChris Hutchins39:50

        I don't think you should, by the way. [laughs]

    18. TFTim Ferriss39:51

        Yeah, no.

    19. CHChris Hutchins39:52

        You could book travel in the portal or transfer them to bank and brokerage accounts. It'd be around $120,000. Just book flights, no problem.

    20. TFTim Ferriss40:00

        Okay.

    21. CHChris Hutchins40:01

        If, and I think you do have an Amex Business Platinum.

    22. TFTim Ferriss40:04

        Yep.

    23. CHChris Hutchins40:05

        Right? You could just book your flights with points in the travel portal. You're capped at how, how much you can do a year, but if every year you used up to 2.85 million, which would take you about five and a half, six years, you'd get $187,000. So more than the $120,000.

    24. TFTim Ferriss40:24

        Mm-hmm.

    25. CHChris Hutchins40:25

        And then if you transferred them and booked, you know, aspirational things with airlines on long-haul international, I think you could get reasonably 250 to $600000 of value. So that's the range. But what should Tim do? [laughs]

14. 40:44 – 43:11

    200 hotel nights or 150 business class flights?

    1. TFTim Ferriss40:44

       Well, let's come back to that. So on the low end, we have use the Amex points on Amazon, right? 'Cause my credit card's already attached. It's one click for a checkbox. It's very easy. That's taking 12 million [laughs] plus points and converting it into $85,000, roughly, of value, right? Now, on the very high end, long-haul international, we've got 600K.

    2. CHChris Hutchins41:08

       Or more. I did some quick math just for fun, and I said, "Okay, what are some things I've done?" Right? I just looked... We've been to the Conrad, which is a chain within Hilton, the Conrad Bora Bora, an amazing property. We've been twice now. We're about to go to the Wal- new Waldorf Astoria in Costa Rica.

    3. TFTim Ferriss41:27

       Mm-hmm.

    4. CHChris Hutchins41:28

       So I looked at those two properties. They have tons of availability using Hilton points. Amex transfers from Hilton one to two, so you'd actually end up with 24 million Hilton points.

    5. TFTim Ferriss41:38

       [laughs]

    6. CHChris Hutchins41:39

       It would be about 200 nights. So if we're talking, like, extreme what you could do, you could transfer all those points over and book 200 nights at a hotel that would normally be 1,500 to $2,000 a night. Like, just to give people's mind, 12 million, what does that mean? Could be 200 nights at, like, an incredibly high-end, beautiful resort.

    7. TFTim Ferriss41:59

       [laughs]

    8. CHChris Hutchins41:59

       If you wanted to take international long haul, like flights to Japan and Europe in business and first class, at redemption values I've gotten multiple times, not once in a lifetime, it'd be somewhere between, like, 130 and 150 one-way flights.

    9. TFTim Ferriss42:17

       To Japan.

    10. CHChris Hutchins42:17

        Let's call it 65 to 75 round trip flights in business class over an ocean.

    11. TFTim Ferriss42:23

        Observation question. So observation, I had this, like, Shawshank Redemption fantasy of sorts, to be clear, towards the very end of the movie, uh, on the beach. [laughs] And I was thinking, well, one reasonably absurd thing that I could do would be, like, a 200-night writer retreat to Bora Bora, right? I might end up more like Tom Hanks in Cast Away, that, that'd be my fear, but at this crazy, crazy hotel, right? So that would be one option for just... If I just wanted to YOLO burn the whole thing. The other I would imagine, tell me if I'm running up against restrictions here, but it's like if I wanted to take, you said 150 flights, let's just call it 150 one-way flights to, say, like Japan, something like that?

    12. CHChris Hutchins43:10

        Sure, yeah.

15. 43:11 – 49:18

    Seat availability challenges and alert rebooking strategies.

    1. TFTim Ferriss43:11

       Okay. Now, I guess I'm gonna run up against the monthly limits here, but would there be a way for me to do one flight to Japan with 150 people, myself included?

    2. CHChris Hutchins43:22

       Let's address the biggest challenge with getting the most out of these points is airlines do not release every f- seat available for use with points.

    3. TFTim Ferriss43:31

       Uh-huh.

    4. CHChris Hutchins43:32

       And when they do, sometimes they release them at tiered pricing. So there might be two seats available for 80,000 points, and then the next two are 300,000, and then that's it.

    5. TFTim Ferriss43:43

       Yep.

    6. CHChris Hutchins43:44

       As an example, this trip we're taking to Japan next year, Japan Airlines releases two seats on every flight when they, when they open the calendar at, like, 360 days. So even knowing everything I know about the system, the most optimal place to put the points to get the deal, we still booked two seats from SFO to Narita and two seats from SFO to Haneda. So my wife and I are each taking one kid, and then we set some alerts, so over the next year if two seats open on either of those flights, we'll log in and change them. Uh, like, the change fee might be $25 on the airline we booked.

    7. TFTim Ferriss44:19

       Yeah.

    8. CHChris Hutchins44:20

       But we couldn't even get four seats on the same flight playing the game as optimally as we want.

    9. TFTim Ferriss44:24

       [laughs] As it stands right now, it's you and one kid and your wife and one kid on two separate flights?

    10. CHChris Hutchins44:29

        Exactly.

    11. TFTim Ferriss44:30

        To two different airports. Oh, fuck.

    12. CHChris Hutchins44:33

        I would say I probably have 80% confidence that by the time we take off we're all gonna be in business class on one flight.

    13. TFTim Ferriss44:40

        Yeah.

    14. CHChris Hutchins44:40

        Like, I- I'm about 80% confident.

    15. TFTim Ferriss44:43

        80% is pretty good.

    16. CHChris Hutchins44:44

        A general rule here, which I'm just gonna give that'll be probably pretty helpful to anyone trying to get the most value out of their points, is the way I would say people that play the game at my level do it is even if you know these dates, no flexibility, one of the great things about points is depending on the program you can book a flight with points and cancel it for no, no penalty. Maybe you pay a $12 fee, a 25, a $50 fee. Depending on the airline, there are different rules, and I would encourage you just search award cancellation rules by airline and you'll find a list. What I will often do is say, "Look, we really wanna go to destination X, and obviously we'd love nonstop, long haul business class. That's the target. But I don't see that now, so let me use some of my points to book a long haul premium economy flight." And then I will use these tools, AwardTool, PointsYeah, Seats.aero is another one if you're, like, a spreadsheet nerd. It's, like, a little bit more database than user-friendly-

    17. TFTim Ferriss45:45

        [laughs]

    18. CHChris Hutchins45:45

        ... but it's really powerful. And I'll set an alert and say, "If two seats open up in business class on the direct flight, or four seats-

    19. TFTim Ferriss45:53

        Mm-hmm

    20. CHChris Hutchins45:53

        ... send me an alert," and then I'll go book that and cancel the other one.

    21. TFTim Ferriss45:56

        Okay.

    22. CHChris Hutchins45:57

        And maybe I have to pay the $12 fee. The way most people I know do this is they book something that's good enough but not optimal, set an alert, and almost always end up with something better.

    23. TFTim Ferriss46:09

        Okay.

    24. CHChris Hutchins46:10

        To the point that we've been at the airport, like check in four hours before our flight from Paris to London back to San Francisco, alert pops up immediately four hours before departure, cancel that flight, book another flight that's Paris direct.

    25. TFTim Ferriss46:26

        Mm-hmm.

    26. CHChris Hutchins46:26

        Now, you might not like that last minute. I don't know exactly if I'm gonna take the flight I, I planned on, but within two weeks of departure, all kinds of stuff happens.

    27. TFTim Ferriss46:35

        Yeah.

    28. CHChris Hutchins46:36

        You can get on Lufthansa first class, you can get on direct flights. So I would say book something that's good enough. Points are often refundable and make it really easy to have speculative bookings, and then you get on something. That said, you're never gonna get 150 seats on the plane.

    29. TFTim Ferriss46:50

        Yeah.

    30. CHChris Hutchins46:51

        So, you know, the best version of that would be pick a day and buy tickets for 150 friends to go somewhere, but no one's really gonna be going to the same place. [laughs] So not as fun.
16. 49:18 – 53:53

    Making use of smaller airline point balances.

    1. TFTim Ferriss49:18

       Also, I should point out to folks a few things. Number one, that I do have people who help with travel, right? So I could very easily have an assistant do this, and I have, still do, for people wondering, you know, virtual assistants in the Philippines and so on, that this is going to become very different, I would say even in the next 12 months, right? I've already invested in companies that are applying AI specifically to the travel vertical. Most people will be able to use AI agents of some type for a lot of this stuff. I would have to imagine within the next two years it could come a lot faster. So having an idea of the process, I think will prove very helpful. So we got AwardTool, Amex. So here are my two, my two questions, right? My two questions are, I've got points on Alaska, American Airlines, Delta, Emirates, TAP Portugal, et cetera, et cetera. Is there an easy way for me to just use those for anything? Like, zero those out. What is the lowest, lightest lift? I guess low makes it a harder lift, but you get the idea. Lightest lift [laughs] in terms of using those. Or is it, you know what? Like, hey, look, you're never gonna use those for anything. Just accept that those are basically sunk costs, and they're trying to pull you into the game of accumulating points, and you, Tim Ferriss, don't need to think about it. Or is there a tool where it's just like, "Hey, I'm never gonna use these for anything. If I can just trade them in for a fucking box of chocolates, and it only takes me 60 seconds, I'll take the box of chocolates." Is there anything to be done with these?

    2. CHChris Hutchins51:03

       I would say the same principle applies, right? If you look at United, you have United, Delta, American, and American and Alaska are both part of the Oneworld alliance. Delta's part of the SkyTeam alliance, and United's part of the Star Alliance. Those cover almost, I don't know, if I had to guess, 90% of all long-haul flights you would ever take in your life.

    3. TFTim Ferriss51:23

       Yeah.

    4. CHChris Hutchins51:24

       And so if whoever's looking to book your travel, you're like, "Oh, you wanna go to Japan?" Way better than any other redemption is just, okay, well, United flies nonstop to Japan, depending on where, what city you're in. So does Delta and American. You're gonna get at least probably one cent of value from each of those points-

    5. TFTim Ferriss51:43

       Mm-hmm

    6. CHChris Hutchins51:43

       ... even if you book it unoptimally. United, a great deal to Japan might be 80,000 points, but you might also find it for 200,000. But if 200,000 points saves you $8,000, like could you do better? Yeah. But I'd rather use that, do that five times, save 40 grand or so. You know, like it's still a good deal.

    7. TFTim Ferriss52:02

       Yeah.

    8. CHChris Hutchins52:02

       So the same rule applies, which is, I would say, when you're booking a trip, go through that same sequence. A lot of these tools, like AwardTool, will show you United, will show you, you know, Delta and American.

    9. TFTim Ferriss52:15

       Mm-hmm.

    10. CHChris Hutchins52:15

        They're not just showing you what you can do with your Amex points.

    11. TFTim Ferriss52:18

        Mm-hmm.

    12. CHChris Hutchins52:18

        And I would say with the caveat that because there's no good alternative, right, with Amex, you can always use those points to just book any flight on any airline at, at least one cent.

    13. TFTim Ferriss52:30

        Mm-hmm.

    14. CHChris Hutchins52:30

        There's no point in cashing them out for a box of chocolates. On United, you can only use them to book United and their partners' flights.

    15. TFTim Ferriss52:37

        Mm-hmm.

    16. CHChris Hutchins52:37

        But the flip side is that there is always a price. Even if there are one last seat, they will still sell it to you with points. It might be a lot of points, but you could still use it for that flight.

    17. TFTim Ferriss52:49

        Mm-hmm.

    18. CHChris Hutchins52:49

        And so I would be blown away if over the next three years you don't take at least one flight that is on each of those airlines-

    19. TFTim Ferriss52:58

        Oh, for sure

    20. CHChris Hutchins52:59

        ... or their partners.

    21. TFTim Ferriss53:00

        Yeah, for sure.

    22. CHChris Hutchins53:01

        And the good news is with United, if you wanna book five seats in business class to Japan, it's gonna be easier to find five seats. It's not gonna be as good of a deal, but you know what? If otherwise you're not gonna use them, why not?

    23. TFTim Ferriss53:14

        Yeah. Also deal. There's like the micro deal and then the macro deal, right? [laughs]

    24. CHChris Hutchins53:18

        Sometimes it just feels good to take a free trip. You know? Like [laughs] who cares if it's a good deal? You went on a trip you weren't gonna take otherwise.

    25. TFTim Ferriss53:25

        Well, totally. Also, if it's a good deal because you have five people flying to the same destination and you know it's guaranteed versus, like [laughs] we're gonna be scattered to the wind and then have to find one another, like Lord of the Rings or something, then fantastic, right? Then psychologically, that's also a good deal. Are there any options, and I think the answer is no, but outside of travel that are interesting in terms of using points?

17. 53:53 – 57:17

    Non-travel uses for points.

    1. TFTim Ferriss53:53

       Let's just say hypothetically, I was like, "You know what? Decided I'm gonna stay in the US for the next three years, and maybe I'll stay in Austin for the next three years straight. I'm tired of traveling."

    2. CHChris Hutchins54:03

       Oh, man.

    3. TFTim Ferriss54:03

       Are there any uses of these points? What are the best options of the worst options [laughs] might be the way to word it.

    4. CHChris Hutchins54:11

       I just looked, and they shut down. I don't know if there's gonna be an alternative, but there is a company that used to exist called Miles for Migrants-

    5. TFTim Ferriss54:20

       [laughs]

    6. CHChris Hutchins54:21

       ... that basically you hand over your miles, and they help, like, refugees relocate around the world using your miles.

    7. TFTim Ferriss54:27

       Oh, okay. That's interesting.

    8. CHChris Hutchins54:28

       But it looks like they don't exist. Like, it looks like they have a, "It's with sad hearts we, we share this news." So there might be some ways to use them for, like, someone else, you know, something like that.

    9. TFTim Ferriss54:39

       Oh. Yeah. That's interesting.

    10. CHChris Hutchins54:41

        So that's one altruist. It's a very charitable cause. It, it provides no value-

    11. TFTim Ferriss54:46

        Yeah

    12. CHChris Hutchins54:46

        ... to you. I don't even think you get the tax write-off.

    13. TFTim Ferriss54:48

        That's fine.

    14. CHChris Hutchins54:48

        But you're helping people relocate with miles you don't need.

    15. TFTim Ferriss54:51

        Here's the thing. Like, I donate a lot of my stuff 'cause if I go and I look at my... You and I both know I have no s- fashion sense, so it's like if I go upstairs and I've got a lot of extra clothing, I'm like, from 1 to 10, how much value am I deriving from, like, this shirt? It's kind of a very left-brained Tim Marie Kondo version. So instead of sparking joy, I'm just like, from 1 to 10, how much value am I getting out of this shirt? Haven't worn it in four months. That's a 1 or a 2 max. If I gave this to Goodwill, somebody would get like a 7 or 8 or more out of it if they really need it, maybe a 10. That's just a better ... use of this thing in the world, right? So for me, I could see actually doing something like that with points.

    16. CHChris Hutchins55:30

        If you found a charity that you cared about and said, "Hey, I've got all these points, can I just help you out?" There's a listener of our podcast, and he reached out to me, and we talked, and he runs a few shelters around the world for women that are suffering from domestic violence and all kinds of stuff, and human trafficking, and he's like, "I use all my points just for the business." All the points his company earns, he uses to book trips-

    17. TFTim Ferriss55:57

        Mm

    18. CHChris Hutchins55:57

        ... for people, for refugees, all this kind of stuff, who have a lot more flexibility. So there's a way that I'm sure someone listening that could reach out [laughs] and be like, "Hey, we could, we could help put these to use if you don't want them."

    19. TFTim Ferriss56:09

        I'm gonna get so many fake-

    20. CHChris Hutchins56:11

        Oh, for sure

    21. TFTim Ferriss56:12

        [laughs] scammers asking for points, but yes.

    22. CHChris Hutchins56:14

        "Tim, give me your points."

    23. TFTim Ferriss56:16

        [laughs]

    24. CHChris Hutchins56:16

        But I would say the easier solution is just decide where you want to give, give with your dollars, and whenever you're taking a trip, tell whoever's booking your travel, a- and this applies to anyone listening, just go, "Look, what would it cost on United? Let's just book it with United this time."

    25. TFTim Ferriss56:30

        Yep.

    26. CHChris Hutchins56:30

        And it's often great deals. We're going to Cabo, and it was a great deal to use points, especially because we weren't sure which day we wanted to come back, so we just booked it for both days, and you can cancel with no penalty. So even if it's not a great deal, just start cranking through them. You don't have any, but just in case anyone's in Austin, one of the best uses of Chase points is transferring them to Hyatt, because Hyatt just is one of the hotel groups that just continues to deliver great value, and there's, like, a Miraval wellness resort right outside of Austin.

    27. TFTim Ferriss57:03

        Oh, yeah. I've been there.

    28. CHChris Hutchins57:05

        It's, like, all-inclusive, and you can use your Hyatt points there. You don't have h- anything that would get you Hyatt points, so-

    29. TFTim Ferriss57:10

        That's okay

    30. CHChris Hutchins57:10

        ... it's not relevant to you, but there are a lot of domestic ways that you could use your points even if you're not leaving

18. 57:17 – 1:01:05

    Strategies for expiring points.

    1. CHChris Hutchins57:17

       the US.

    2. TFTim Ferriss57:18

       So let's look at a situation on my spreadsheet here.

    3. CHChris Hutchins57:22

       Yeah.

    4. TFTim Ferriss57:22

       And let's pretend the numbers are bigger than they are. So I have points on Emirates Skywards, and I have points on TAP Air Portugal. The numbers are not as big as the other airlines.

    5. CHChris Hutchins57:32

       Yeah.

    6. TFTim Ferriss57:32

       But let's pretend that these were more miles, because I'm bringing these up, as you can guess, because they're both expiring this year.

    7. CHChris Hutchins57:43

       Yep.

    8. TFTim Ferriss57:44

       What can people do if they're like, "Oh, shit, I've got three to six months," maybe it's a year, "before these things expire. I do not have any need, maybe no desire, to take, like, an emergency [laughs] trip to," fill in the blank location. Is there anything to be done, or is it just like, "Ah, you son of a bitch, you got me"?

    9. CHChris Hutchins58:07

       No, no, there's multiple things. So most of the programs in the US now don't expire. If you have the credit card with the company you earn points in, usually the credit card points don't expire. But a lot of programs do. And I'd say there's two versions of expiration. There's a couple airlines, Japan Airlines, ANA, where it's truly, like, three years, and they're gone, nothing you can do, and then there are a bunch where it's like, I think American Airlines, if you have no activity for two years, they expire.

    10. TFTim Ferriss58:35

        [laughs] Loyalty rewards. [laughs] Sometimes the stick is better than the carrot. [laughs]

    11. CHChris Hutchins58:41

        I have, in the past with American, I've donated 1,000 miles. That's activity.

    12. TFTim Ferriss58:46

        Yep.

    13. CHChris Hutchins58:46

        That kicks you another two years down the road. You can buy a magazine with your miles, kick the can two years down the road.

    14. TFTim Ferriss58:53

        Yep.

    15. CHChris Hutchins58:53

        Emirates, for example, lets you transfer your Emirates points to Marriott.

    16. TFTim Ferriss58:57

        Mm.

    17. CHChris Hutchins58:57

        So funny enough, it's like you've got Marriott points, they need some activity or they're gonna expire. You have Emirates points, maybe you could transfer all your Emirates points to Marriott, which you're probably more likely to find a hotel that you could use to book with Marriott points, and cash out your Emirates balance.

    18. TFTim Ferriss59:13

        Yep.

    19. CHChris Hutchins59:14

        With TAP Air Portugal, you've got an orphaned 6,500 miles, probably not even enough to book really anything. I honestly wouldn't feel too guilty just letting them expire.

    20. TFTim Ferriss59:26

        Mm-hmm.

    21. CHChris Hutchins59:27

        The thing that I would note in the future for someone listening is TAP Air Portugal is a part of, I believe it's Star Alliance. Yeah, Star Alliance. Whenever you fly on TAP, you should just put in your United number.

    22. TFTim Ferriss59:40

        Mm.

    23. CHChris Hutchins59:41

        Try not to overcomplicate things. You're flying on Air France, put in your Delta number. Do I think Delta points are the best ever? No, and if you wanna play this game at a crazy level and have six-figure balances and 25 airlines, great, but when you're getting started, if you have Delta, American, or Alaska, and United, any foreign flights, credit there, and, and then you don't have to worry about having these little balances all over the world in random airlines.

    24. TFTim Ferriss1:00:09

        Yeah. That's a good point.

    25. CHChris Hutchins1:00:11

        But at 6,000 points, I don't care. At Emirates, if you thought one day you'd use them, great. Otherwise, I'd transfer them to Marriott. I will say there's a strange reason why I ended up with 25,000 Aegean Air miles.

    26. TFTim Ferriss1:00:26

        [laughs]

    27. CHChris Hutchins1:00:27

        Which is a Greek airline, part of Star Alliance, and I was like, "What do I do with these miles?" Like, I don't e- I'm not gonna go to Greece. But Aegean Airlines is part of Star Alliance, so I just use them to book a flight from San Francisco to Denver.

    28. TFTim Ferriss1:00:38

        Mm.

    29. CHChris Hutchins1:00:39

        You know, like, on United.

    30. TFTim Ferriss1:00:40

        Yeah, okay.
19. 1:01:05 – 1:02:10

    Flexible booking for maximum value.

    1. TFTim Ferriss1:01:05

       Okay. That makes a whole lot of sense. All right. Where should we go from here? I mean, I'm tempted to sprinkle in some crazy points stories, but we could also go somewhere else, right? Because it, it seems like the answer is use these for flights that are coming up. They don't expire. There's definitely part of me that's like, "God, it's just-" It's not very inspiring, but I certainly could do it. That's the best value per point is to use AwardTool, and then if that fails, Amex Travel Portal

    2. CHChris Hutchins1:01:35

       What if we did it this way? I said the best deals are with the ultimate flexibility. So you could say, "Hey, I just wanna have an amazing... Like, just blow my mind. Make me feel like I got so much value out of this." What could we do, right? Like-

    3. TFTim Ferriss1:01:50

       Yeah

    4. CHChris Hutchins1:01:51

       ... what could we do that's really awesome? Block off a week and say, "This week, I'm just gonna blow it out of the water, and I'm gonna do something awesome."

    5. TFTim Ferriss1:01:59

       Yeah.

    6. CHChris Hutchins1:01:59

       And I don't know what that's gonna be. I don't know where it's gonna be. And you go to one of these tools, and you say, "Where can I go this week?" And I think you could have a good time anywhere.

    7. TFTim Ferriss1:02:09

       Yeah, I agree.

20. 1:02:10 – 1:05:55

    Using Seats.aero for flights.

    1. CHChris Hutchins1:02:10

       So for example, Seats.aero, one of the cool things they have is they have this tool that's like the ANA first class finder and the Lufthansa first class and the JAL first class finder. So you could say Lufthansa first class. Well, for anyone who's interested, the San Francisco to Frankfurt flight today [laughs] you can book using United miles in first class for 165,000 points.

    2. TFTim Ferriss1:02:33

       Yeah.

    3. CHChris Hutchins1:02:33

       Now, one of the best things about Lufthansa first class, and I've not been able to fly it, is that in Frankfurt they have their own private first class terminal.

    4. TFTim Ferriss1:02:41

       [laughs]

    5. CHChris Hutchins1:02:41

       It's separate from the other terminal. It's known for if you go take a bath there, they give you these rubber ducks that you can post on the internet to show people that you-

    6. TFTim Ferriss1:02:49

       [laughs]

    7. CHChris Hutchins1:02:50

       ... flew first class on Lufthansa. But, like, you could basically just schedule a, "I'm gonna take an amazing trip. I'm gonna go somewhere awesome," and just see where that leads you.

    8. TFTim Ferriss1:03:01

       Yeah.

    9. CHChris Hutchins1:03:01

       We've done this a handful of times, and we ended up at this amazing resort in Mallorca last year called Cap Rocat. It's a small luxury hotel of the world. It's built in an old fortress. If you just search for it, you're like, "Wow, it looks beautiful."

    10. TFTim Ferriss1:03:17

        Cap Rocat.

    11. CHChris Hutchins1:03:18

        You know, if you wanna go in the summer, it's like 2 to 5,000 a night.

    12. TFTim Ferriss1:03:22

        Yeah.

    13. CHChris Hutchins1:03:22

        And we're like, "Wow, Hilton has five nights here." We had five free Hilton night certificates. We found some points to get ourselves to Europe. I think one interesting thing for people to consider, we live in the Bay Area. We wanted to go to Mallorca. If you just search for a flight from San Francisco to Mallorca-

    14. TFTim Ferriss1:03:40

        Yeah

    15. CHChris Hutchins1:03:40

        ... it's gonna be a lot harder to find a good deal. So instead, we searched for San Francisco to Europe. We ended up getting a flight to Paris, and then we just bought a $79 ticket from Paris to Mallorca. And so consider the fact that you could buy really cheap flights at the beginning or end of your trip, and your points are gonna get you on these long-haul routes. We ended up having, like, a $20,000 vacation. We didn't even realize when we booked it that we were flying to Paris during the Olympics.

    16. TFTim Ferriss1:04:08

        [laughs]

    17. CHChris Hutchins1:04:09

        So we ended up staying there for two days and going to the Olympics, and we did the whole thing on points. It was, like, $20,000 saved, not $20,000 of value.

    18. TFTim Ferriss1:04:19

        Hmm.

    19. CHChris Hutchins1:04:19

        Because it was, like, actually saved over if we had paid cash. So it was amazing.

    20. TFTim Ferriss1:04:25

        Yeah. All right. I like that idea.

    21. CHChris Hutchins1:04:28

        I would challenge, give me a week of your time, and I will come back with a, "Tim is going to this place and this amazing deal, and he's gonna stay at this incredible property and just unwind for a week and explore whatever part of the world we send him to."

    22. TFTim Ferriss1:04:45

        [laughs] Sierra Leone, Four Seasons. [laughs] Here I come. [laughs] So what was the name of that place? Si Rocat. No. What was it?

    23. CHChris Hutchins1:04:56

        Cap Rocat.

    24. TFTim Ferriss1:04:57

        Cap Rocat.

    25. CHChris Hutchins1:04:57

        Beautiful hotel.

    26. TFTim Ferriss1:04:59

        Sounds like a Russian prison drug. I like it.

    27. CHChris Hutchins1:05:03

        There's tons of ava- I mean, I don't know what Mallorca is like in October, but right now you can go for a week or two in October. Obviously, I know summer's probably the prime time, but I think when you start to look at shoulder seasons and, and last-minute stuff, you could just get crazy, crazy deals.

    28. TFTim Ferriss1:05:20

        Shoulder seasons means right outside of the prime season, like, to either side of it?

    29. CHChris Hutchins1:05:25

        Yeah. So we're going to Costa Rica in June, which is not the height of rainy season, but it's certainly not, like, the most perfect time to go to Costa Rica.

    30. TFTim Ferriss1:05:37

        Mm-hmm.
21. 1:05:55 – 1:07:04

    Using Rooms.aero for hotels.

    1. CHChris Hutchins1:05:55

       I think we mentioned all these tools before, but when it comes to hotels, a lot of these tools also have the same thing for hotels, so you can go switch from the flight page to the hotel page.

    2. TFTim Ferriss1:06:05

       Mm-hmm.

    3. CHChris Hutchins1:06:06

       Seats.aero has a sister site called Rooms.aero.

    4. TFTim Ferriss1:06:09

       [laughs]

    5. CHChris Hutchins1:06:09

       And you can literally be like, "Find me a small luxury hotel in the world that has five nights available June 25th. Where am I going?"

    6. TFTim Ferriss1:06:17

       Now, is the .aero, like, a wink wink insider thing in the travel world, or is that just an indication of the person who made this spreadsheet heavy website is the same person who should not be in charge of branding? [laughs]

    7. CHChris Hutchins1:06:30

       [laughs] I know the guy behind it's an engineer, and I think it was like, "What'd be a cool easy name?" Seats.aero.

    8. TFTim Ferriss1:06:36

       Okay. [laughs]

    9. CHChris Hutchins1:06:37

       Easy domain, short word.

    10. TFTim Ferriss1:06:39

        Arrow spelled like an arrow, A-R-R-O-W?

    11. CHChris Hutchins1:06:42

        Oh, sorry, A-E-R-O, Seats.aero. Like-

    12. TFTim Ferriss1:06:46

        Oh, Jesus

    13. CHChris Hutchins1:06:46

        ... aeronautical, you know, aeroplane.

    14. TFTim Ferriss1:06:49

        See? There's the problem. I got it. .Aero, A-E-R-O. I am absolutely not the only person who immediately went to arrow, [laughs] A-R-R-O-W.

    15. CHChris Hutchins1:06:59

        I'm very glad we, we clarified that, right? [laughs]

    16. TFTim Ferriss1:07:02

        [laughs] Show notes would've been messy.

22. 1:07:04 – 1:09:56

    Point strategies gone wrong and the optimizer’s curse.

    1. TFTim Ferriss1:07:04

       Okay, so I, I wanna explore a couple things. Number one is points gone wrong.

    2. CHChris Hutchins1:07:09

       Yeah.

    3. TFTim Ferriss1:07:09

       Right? [laughs] In other words, where [laughs] you did something and you're like, "Fucking A, that was just such a waste of life energy," right? There must be some examples of where this didn't work out, right? Or where you had a practice, and you were like, "At the end of the day, isn't worth it." Now- I have to bust your balls about this because it's just so funny. So I've, I've heard you tell stories of comparison shopping for fruit at the grocery store. You will drive from one grocery store to another to save something like [laughs] correct me if I'm getting this wrong, but like two or three bucks [laughs] on berries, something like that. But I'm wondering, even for you, if there's been an example where there's like a practice or an attempt and you're like, "Okay, that really didn't work out. That was just way more headache or way more time than ended up being worth it." Right? The juice wasn't worth the squeeze. How often do you feel that way, and can you give an example?

    4. CHChris Hutchins1:08:08

       I think the, I don't know, I'll call it the optimizer's curse, but like that is the challenge that I have learned to get better at over the last year or two or three, which is, take the berries example. I think I'm probably more likely to look online and be like, "Should I order my groceries from, you know, Amazon Fresh or Whole Foods, and which one's cheaper?" Than necessarily drive store to store. But I'll credit Ramit Sethi for these money rules where it's like, okay, for groceries, we stop caring. Like, it doesn't matter.

    5. TFTim Ferriss1:08:40

       [laughs]

    6. CHChris Hutchins1:08:41

       Now, does that mean that when I go to Costco to buy berries and I might see like blueberries are twice the normal price, maybe we just buy strawberries instead.

    7. TFTim Ferriss1:08:50

       [laughs]

    8. CHChris Hutchins1:08:51

       I'm not gonna not buy berries if they're expensive, but I, I might pick the berry that's the better deal this week. But I'm not gonna not do it, and I'm not gonna drive to another grocery store to get it.

    9. TFTim Ferriss1:09:01

       [laughs] Throw in $15,000 worth of gold bars [laughs]

    10. CHChris Hutchins1:09:05

        Yeah

    11. TFTim Ferriss1:09:05

        ... with my, with my bargain basement strawberries.

    12. CHChris Hutchins1:09:09

        Yeah, yeah. It's a rounding error. The transaction would be 15,000 and, like, 12 or 15,000 and 14.

    13. TFTim Ferriss1:09:14

        [laughs]

    14. CHChris Hutchins1:09:15

        But I've had to get a lot better at this because there are times where I could spend three hours trying to find a flight deal and, like, figure out the most optimal way to do it, only to be like, "Oh, we're not even gonna take this trip."

    15. TFTim Ferriss1:09:27

        Right. Yeah.

    16. CHChris Hutchins1:09:28

        My wife sometimes asks me, I was like, "Hey, which flight should we take for this trip?" And then she's like, "I'm okay answering that question, but why do I have a 47-row spreadsheet [laughs] as like the source of this information?" And so for me, part of it is sport, like we talked about.

    17. TFTim Ferriss1:09:44

        Mm-hmm.

    18. CHChris Hutchins1:09:44

        Part of it is figuring out at what level do we stop caring? So it's like when I was early to this game, it's like if I'm gonna save $20, I'll stop caring. Maybe now that threshold's at $100.

    19. TFTim Ferriss1:09:52

        Mm-hmm.

    20. CHChris Hutchins1:09:53

        Maybe for some people it's at 1,000 or even higher.

23. 1:09:56 – 1:10:49

    Websites to decide if a trip is worth the points.

    1. CHChris Hutchins1:09:56

       So I've gotten better at, is this a thing I wanna optimize or is this a thing where I'm just gonna buy the flight? I, I gotta go to this conference in San Diego. Flights aren't that expensive. Let's just buy it.

    2. TFTim Ferriss1:10:06

       Mm-hmm.

    3. CHChris Hutchins1:10:07

       For anyone thinking that way, and this is also good for you, there's this great browser extension called Points Path, which just layers on Google Flights.

    4. TFTim Ferriss1:10:15

       Points Path.

    5. CHChris Hutchins1:10:16

       And they have an opinion.

    6. TFTim Ferriss1:10:17

       Okay.

    7. CHChris Hutchins1:10:18

       They're like, "This is a good deal with points. This is a good deal with cash."

    8. TFTim Ferriss1:10:22

       Mm-hmm.

    9. CHChris Hutchins1:10:22

       So you're like looking on Google Flights to go to San Diego and it's like, hey, actually go use United points. Don't buy this one. Oh, this is a bad deal. So it's even easier than these other tools 'cause it lives where you're already searching.

    10. TFTim Ferriss1:10:34

        Yeah.

    11. CHChris Hutchins1:10:34

        Now, and sometimes I'm like, let's just book it, be done. I don't wanna spend my afternoon on saving $5 or $20 or even $50.

    12. TFTim Ferriss1:10:42

        [laughs]

    13. CHChris Hutchins1:10:43

        I kinda do at $50, but I should not.

    14. TFTim Ferriss1:10:45

        [laughs]

    15. CHChris Hutchins1:10:47

        I think that's it.

24. 1:10:49 – 1:13:37

    The Dunning-Kruger curve of points hacking.

    1. CHChris Hutchins1:10:49

       Sometimes this stuff goes wrong, and wrong is a stretch, but I make mistakes that I talk about not making all the time.

    2. TFTim Ferriss1:10:57

       Mm-hmm.

    3. CHChris Hutchins1:10:57

       And I, I had this woman, Devon Gimbel, who has a podcast called Point Me to First Class, on and we talked about the points journey and like you start off and it's so great. You're like, "I used my points at Amazon. This is amazing," and it feels like points are amazing, and then you start to learn more. And this is, I think it's the Dunning-Kruger effect. It's like now that I know a little more, oh man, now I know I've been doing it wrong the whole time. You feel terrible. And then you start to learn and you're like, now I'm doing great again. But there are gonna be a lot of people that listen to this conversation right now and they're like, "Now I know more. Now I feel worse about what I'm doing."

    4. TFTim Ferriss1:11:31

       [laughs]

    5. CHChris Hutchins1:11:32

       There is another side to that, the valley of despair, where we'll get past it or listen to that conversation I had with her and that would help.

    6. TFTim Ferriss1:11:40

       Wait, the value of despair? Is that what you said?

    7. CHChris Hutchins1:11:42

       Valley of despair.

    8. TFTim Ferriss1:11:44

       Oh. [laughs] I like both. Yeah, that's like the trough of sorrow in Y Combinator.

    9. CHChris Hutchins1:11:50

       Yes. There's like dozens of names of, of what it means to learn more and then not yet master it and all that. So I think to where you were going, I have made mistakes. I've booked flights that were non-cancellable and then tried to cancel them and got no refund. Like, I've booked trips we never needed to take. I've booked backup flights and forgot to cancel them and lost points. Make tons of mistakes doing all this. That's just how we learn and even once you know the things, you do it wrong. But the value of everything I've gotten out of it has far exceeded those mistakes and I'm okay with making those mistakes. And I've just learned to say, "Is this the giant trip of the year where we can save $10,000 or is this the I need to go to this place for a meeting and it's not worth my time?"

    10. TFTim Ferriss1:12:35

        Yeah, totally.

    11. CHChris Hutchins1:12:36

        And that changes, right? Like, earlier in your career it might always be worth your time.

    12. TFTim Ferriss1:12:40

        Oh, for sure. Yeah, definitely. I mean [laughs] yeah, back in the day. I mean, when I first moved to Silicon Valley, I don't know if I ever told you this. When I very first moved, it was 2000, couldn't find an apartment. Bought a standby ticket to, I think it was, I was just waiting for San Francisco or San Jose. So I had, I wore my one suit back when I thought I needed a suit to do like job interviews [laughs] in Silicon Valley and ended up staying at a kickboxing gym. This was Fairtex Gym and I lived on a bunk bed with one of the Thai guys up in basically the attic and I would like wash my clothing in the sink. And so like I was definitely looking for any cost savings that I could find in any capacity whatsoever. And like you said, the threshold has just changed over time and how I think about my time has changed

25. 1:13:37 – 1:16:56

    When frugality becomes a burden.

    1. TFTim Ferriss1:13:37

       over time. But I'll talk about another optimizer's curse actually. Because I don't think this gets as much air time, or at least I haven't heard very many people talk about it. There's the curse of, like, over-optimizing deals/frugality, but then there's the curse of over-optimizing efficiency where people come to value their time so highly that any wasted minute causes tremendous psychological anguish. Do you know what I mean? Like, if they have to wait for something for five minutes, it bothers them to such an extent, maybe even after the fact, that just like the sort of frugality and excess kind of becomes the opposite of what, what you were looking for, which is this, like, psychological peace perhaps, or quality of life. The same thing is true with people who feel like they have more money than time, or that their time is incredibly, incredibly valuable. Like, there is a point where it starts to hurt you and not help you. Does that make sense?

    2. CHChris Hutchins1:14:38

       Yeah.

    3. TFTim Ferriss1:14:39

       It's like, so finding that Goldilocks is something I think about a lot because if you read The 4-Hour Workweek, whatever, yes, like there are guidelines for people who have perhaps not ever tried to objectively value their time for looking at annual income and cutting this, this, and this to determine your kinda hourly rate per se, right? The value of an hour of time. But when you take that and apply it to everything and start to really ratchet up your perceived value of time, it can actually create a lot of anxiety, which I imagine the sort of hyper-frugality side can as well.

    4. CHChris Hutchins1:15:15

       Yeah.

    5. TFTim Ferriss1:15:15

       Right? So like they share more in common than I think people might realize.

    6. CHChris Hutchins1:15:20

       I think about this all the time. When I spend time... The fact that it is sport makes it easier for me to justify spending an hour going down a rabbit hole, because not only do I kind of enjoy the process, but I can also... I have a podcast. I can share the process with other people, and then they can skirt some of the process by not making the mistakes I do.

    7. TFTim Ferriss1:15:39

       Yeah.

    8. CHChris Hutchins1:15:40

       On the flip side, I often think about what is my time worth. You know, I get requests for people to, "Oh, hey, could you consult on this thing?" And I'm like, "Ah, it's just... I got other stuff to do." And I'm like, "Well, if I said no to a consulting call for $250, then, like, my time must be worth $250." Do I wanna lay in bed and watch this movie? It's $250 to watch a movie.

    9. TFTim Ferriss1:16:03

       [laughs]

    10. CHChris Hutchins1:16:04

        Somehow I've been able to just be like, "Nope," and I just ignore it all.

    11. TFTim Ferriss1:16:07

        Yeah.

    12. CHChris Hutchins1:16:07

        But I imagine there are people that think about that and can't stop thinking about it, and my only advice is to just try to not calculate every little thing, because it's impossible, and think about maybe your 9:00 to 5:00 time. You know, think about your work hours of whether they're most efficiently used. But in free time, I try to ignore the value of time. It's like, uh, does it cost me $1,000 an hour to play with my kids? Like, I don't... That-

    13. TFTim Ferriss1:16:34

        [laughs]

    14. CHChris Hutchins1:16:34

        ... that's just a, a ridiculous thing I'm not even gonna entertain.

    15. TFTim Ferriss1:16:38

        Where are the robots when you need 'em?

    16. CHChris Hutchins1:16:40

        [laughs] Yeah.

    17. TFTim Ferriss1:16:40

        Don't worry, they're coming. Soft hands, soft hands. Don't be the first of 100 parents to test 'em out. So looking at what I've done, I also wanna ask you about the future of travel, so I'll just plant that seed.

    18. CHChris Hutchins1:16:51

        Okay.

    19. TFTim Ferriss1:16:51

        Like what you think this space is gonna look like in the next handful of years, or what innovations

26. 1:16:56 – 1:19:52

    What I could have done differently with my reward cards.

    1. TFTim Ferriss1:16:56

       you'd like to see. What could I have done in the beginning, right? What would you have done differently looking at what I've accumulated?

    2. CHChris Hutchins1:17:05

       I tried to model out what you could've done and what the impact would've been.

    3. TFTim Ferriss1:17:09

       Oh, boy. [laughs]

    4. CHChris Hutchins1:17:11

       And my rough answer... And I built this whole, I don't know, this optimizer's tool which is like you could basically put in all, how much you spend, and you could check off which cards you have and see other cards and see how much better it would be if you had other ones. The short answer is almost everyone is optimal with two things: a card that gives them elevated earning on the things that they spend the most on, and a card that gives them 2% or 2X points on everything else. That is the optimal solution.

    5. TFTim Ferriss1:17:47

       Okay.

    6. CHChris Hutchins1:17:47

       And so in the case of the Amex Platinum card, which I have multiple of, you're getting one point on everything and five points on flights specifically booked with the airline. Not a great card for anything other than flights booked with airlines.

    7. TFTim Ferriss1:18:01

       [laughs]

    8. CHChris Hutchins1:18:02

       But getting five points on flights booked with airlines, excellent.

    9. TFTim Ferriss1:18:04

       Yeah.

    10. CHChris Hutchins1:18:05

        But if you figure 90% of the spend you put on that card was not a flight booked with an airline-

    11. TFTim Ferriss1:18:12

        It's advertising

    12. CHChris Hutchins1:18:12

        ... yeah, advertising.

    13. TFTim Ferriss1:18:13

        For companies, yeah.

    14. CHChris Hutchins1:18:15

        I would say for your specific case, it's like, well, the Amex Business Gold card gives you 4X points on advertising spend-

    15. TFTim Ferriss1:18:22

        Yeah. I fucked that up

    16. CHChris Hutchins1:18:23

        ... up to $150,000 a year. But, like, you'd be much better off getting 4X than 1X on ad spend.

    17. TFTim Ferriss1:18:29

        Yeah, it's much more than I put on travel, I mean, by 10X, 20X, 50X.

    18. CHChris Hutchins1:18:35

        If you took a card, like Capital One has the Venture and the Venture X card, and on the business side they have the Venture X Business, which is just 2X on everything.

    19. TFTim Ferriss1:18:43

        Mm-hmm.

    20. CHChris Hutchins1:18:44

        There's no games to play. It's not what do I use for this? You get 2X on everything. You would've probably been a lot better off.

    21. TFTim Ferriss1:18:49

        Mm-hmm.

    22. CHChris Hutchins1:18:50

        Right? Because you were getting five on flights, but one on everything else. The Amex Business Platinum does one and a half on purchases over $5,000, so maybe you were getting one and a half on a lot of those things for business. But you could've just gotten two on everything. It probably would've simplified your life.

    23. TFTim Ferriss1:19:07

        Yeah.

    24. CHChris Hutchins1:19:07

        And then you could've picked a card, whether it's personal... I'll focus personal use case, which is like the Chase Sapphire Reserve card is 3X on travel and dining. The Amex Gold card is 4X on dining and groceries.

    25. TFTim Ferriss1:19:22

        Yeah.

    26. CHChris Hutchins1:19:22

        I don't wanna go down every card under the sun, but there are cards that are targeting people who spend in categories that are pretty common, like travel and dining are two of the biggest ones where cards reward you. So I think the average person is best off with a card that earns three to four points on the categories they spend the most on, and a card that earns two on everything else. And whether that's two points or 2% cash back- ... kind of is up to you. Like, do you

27. 1:19:52 – 1:22:27

    Buying vs. earning.

    1. CHChris Hutchins1:19:52

       want to play the game and try to get the most out of it and take all these aspirational trips, or do you wanna just put cash in the bank and not worry about it? And that doesn't mean you can't get some of the value.

    2. TFTim Ferriss1:20:04

       Mm-hmm.

    3. CHChris Hutchins1:20:04

       If we loop back to one example I s- shared, the Cap Rocat Hotel. Beautiful hotel.

    4. TFTim Ferriss1:20:08

       Yep.

    5. CHChris Hutchins1:20:09

       It was 120,000 Hilton points per night. Hilton points, when I booked the hotel, were on sale for half a cent each.

    6. TFTim Ferriss1:20:17

       [laughs]

    7. CHChris Hutchins1:20:18

       So there's this crazy arbitrage that required no playing the points game, which was a night at the hotel was, like, $3,000 or 120,000 points, but on the website, the same day, you could just buy 120,000 points for $600.

    8. TFTim Ferriss1:20:32

       [laughs]

    9. CHChris Hutchins1:20:32

       So someone who'd been playing the cash back game their whole life could just go to the Hilton website, buy 120,000 points for $600, book the $3,000 room [laughs] for 120,000 points, and get effectively the same elevated value that I got from playing the points game without ever playing the points game.

    10. TFTim Ferriss1:20:51

        Yeah. That was on the same website?

    11. CHChris Hutchins1:20:53

        I mean, that was just on hilton.com. The Hilton points are, are notorious for going on sale all the time. I will say Chase Am- you can't buy Chase points, you can't buy Amex points. Airlines points go on sale from time to time.

    12. TFTim Ferriss1:21:06

        Yep.

    13. CHChris Hutchins1:21:06

        There are places where you could buy points from airlines if you see an amazing deal.

    14. TFTim Ferriss1:21:11

        Mm-hmm.

    15. CHChris Hutchins1:21:11

        And I would encourage people to do that, right? Like, let's say you have no points and you're about to take a big international trip. Go to AwardTool, go to PointsYeah. If you see a ridiculous deal and you don't have any points, chances are at least one of the airlines you can book that deal from sells their points, and it might be a better deal to go buy United points or Air Canada points and book it with points.

    16. TFTim Ferriss1:21:32

        Let me hop in here, all right. So I love the kind of on the same website [laughs] arbitrage, because it makes me think that there's some guy running spreadsheets, doing all sorts of fine-tuning internally who's like, "This is for my boys and girls who get the game" [laughs] and just planted, like, this Easter egg, wink, wink, for anybody who actually happens to get the scent trail. I like that story, so I'm gonna stick with it.

    17. CHChris Hutchins1:21:56

        But the reality is most people that have a Hilton account and have Hilton points are using it to book a night at the Hilton Garden Inn for their family reunion in some city in America. They're not trying to go to the Maldives or Bora Bora every weekend and, and they're not ready to book it on a dime.

    18. TFTim Ferriss1:22:13

        Well, you're an edge case.

    19. CHChris Hutchins1:22:14

        These aspirational stories are just that.

    20. TFTim Ferriss1:22:16

        Yeah.

    21. CHChris Hutchins1:22:16

        They're aspirational.

    22. TFTim Ferriss1:22:17

        Hilton can afford the edge cases.

    23. CHChris Hutchins1:22:20

        And so if they're not in your short-term future, racking up Hilton points doesn't do you a lot. [laughs]

    24. TFTim Ferriss1:22:26

        Yeah.

28. 1:22:27 – 1:23:30

    Optimal reward cards for small-business owners.

    1. TFTim Ferriss1:22:27

       All right. Let me just come back to my own situation. So it sounds like for what I'm doing, assuming that... Because this is gonna be true for, I would imagine, a lot of solopreneurs or entrepreneurs with small businesses, that the vast majority of their expenses are on things like advertising, media, maybe also for different service providers, like email service provider, blah, blah, blah, blah, blah, right? Like, those are gonna be-

    2. CHChris Hutchins1:22:55

       Yeah

    3. TFTim Ferriss1:22:55

       ... the big buckets. So it sounds like a next step for me, at the very least, would be to get a gold card.

    4. CHChris Hutchins1:23:01

       Business gold, just to be clear.

    5. TFTim Ferriss1:23:02

       Business gold. Thank you. Business gold. Just to move those types of expenses to that immediately, 'cause it doesn't take much from me.

    6. CHChris Hutchins1:23:10

       Yeah.

    7. TFTim Ferriss1:23:10

       And it will, I guess, 1.5 to 4X my return on that spend.

    8. CHChris Hutchins1:23:16

       Yeah.

    9. TFTim Ferriss1:23:16

       Right?

    10. CHChris Hutchins1:23:17

        And then if someone's in the Chase ecosystem, there's a Chase Ink Preferred card, which is 3X on ad spend and travel.

    11. TFTim Ferriss1:23:23

        Mm-hmm. Yeah.

    12. CHChris Hutchins1:23:24

        I think it's also office supplies and shipping or something like that. I can't remember all, all of them off the top of my head. So

29. 1:23:30 – 1:27:36

    Status benefits and Southwest’s companion pass.

    1. CHChris Hutchins1:23:30

       that's one path.

    2. TFTim Ferriss1:23:32

       Mm-hmm.

    3. CHChris Hutchins1:23:32

       The other path is, okay, yes, you like these points, but you don't really get a lot of tangible value in the moment from them.

    4. TFTim Ferriss1:23:42

       Yeah.

    5. CHChris Hutchins1:23:42

       Until you can redeem them, there's no value. So what some people do, and clearly 1% of GDP on Delta cards as an example, most of the airline credit cards, and Hyatt notably, because they don't just give away their top tier of status, you can spend your way to status on most of the domestic airlines like United, American, and Delta-

    6. TFTim Ferriss1:24:03

       Mm-hmm

    7. CHChris Hutchins1:24:03

       ... and Hyatt, their highest Globalist status. So you could get a Delta Reserve Amex, throw a million dollars of spend a year, and you'd be Delta Diamond. I don't know the exact number. Depending on the airline, it's between 200 and $400,000 a year would get you their highest tier of status.

    8. TFTim Ferriss1:24:22

       What does that give you?

    9. CHChris Hutchins1:24:23

       Depending on the airline, it might be-

    10. TFTim Ferriss1:24:26

        Caviar and blowjobs? [laughs]

    11. CHChris Hutchins1:24:27

        ... priority boarding, upgrades as available, right? Like, not any time.

    12. TFTim Ferriss1:24:32

        [laughs]

    13. CHChris Hutchins1:24:33

        Free Wi-Fi. Whatever the perks are.

    14. TFTim Ferriss1:24:34

        Yeah.

    15. CHChris Hutchins1:24:34

        Like, Southwest is one of the ones where you actually get the guarantee. If you earn 125,000 points on a South... through a... If you spend $125,000 on a Southwest card, you will get companion pass.

    16. TFTim Ferriss1:24:48

        Yeah.

    17. CHChris Hutchins1:24:48

        You can name any person your companion, and every time you fly, as long as there are two seats on the flight, they will fly free with you.

    18. TFTim Ferriss1:24:56

        Mm.

    19. CHChris Hutchins1:24:56

        And it's not two seats when you get there. You can reserve the seat when you're booking. So right now my wife is my companion on Southwest. If I buy a flight, she can come for free, taxes excluded. So you pay the 5 to $50 depending on where you're going.

    20. TFTim Ferriss1:25:11

        Mm-hmm.

    21. CHChris Hutchins1:25:11

        That one's one where, like, every single flight. So if you flew Southwest a lot, which I'm guessing you don't, spending 125,000 on a Southwest card, bring your companion for free. I know a lot of people, my sister-in-law actually and her husband, they own a handful of small businesses in Colorado, and they have two kids. They put a ton of their business expenses on two different Southwest cards. They each have companion pass because of it. All the points and miles they've earned from Southwest, they use to buy flights for them, and their kids fly free with them everywhere they go.

    22. TFTim Ferriss1:25:43

        Yeah. That makes sense.

    23. CHChris Hutchins1:25:44

        Could they have had more Amex points or Chase points if they played the game differently? Maybe. But right now, do they get to take vacations all the time with their family and never pay for any of it? And their kids' flights are always free. Their flights are paid with the points they earn on the card. Yeah. Pretty cool. Like [laughs]

    24. TFTim Ferriss1:26:02

        Yeah

    25. CHChris Hutchins1:26:02

        ... they don't think about the cost of travel. Now, they can only go where Southwest goes if they wanna go for free, so [laughs] trade-offs.

    26. TFTim Ferriss1:26:08

        Yeah, I mean, it's all trade-offs, and I actually do sometimes fly Southwest, [laughs] you'd be surprised to know. It's not all the time, but Southwest and JetBlue, I actually fly with some regularity. That's a story for another time.

    27. CHChris Hutchins1:26:21

        But I just share that someone who spends a lot of money for their business or their person, the optimal solution might be to get a card that matches their expenses or a 2X 2% card and just throw all the business expenses on those cards.

    28. TFTim Ferriss1:26:36

        Mm-hmm.

    29. CHChris Hutchins1:26:36

        And for that case, Bank of America similarly has business cash back cards that if you put $100,000 in a business bank or brokerage account-

    30. TFTim Ferriss1:26:45

        Mm-hmm
30. 1:27:36 – 1:32:12

    Pudding cups, $1 coins, and other heartwarming arbitrage tales.

    1. TFTim Ferriss1:27:36

       All right. So the future of travel we can come to. I know I bookmarked that. I'll let you choose. I'll give you a couple of prompts. Pudding cups, US Mint, or your wedding. Which would you like to go with first?

    2. CHChris Hutchins1:27:51

       I mean, they're pretty short stories. I'll just run through them in the order you gave them. So this guy, Dave Phillips, back in the late '90s noticed that there was this promo from Healthy Choice. If anyone remembers, the green brand that made all these probably not in today's standards healthy foods. And it was like you get 1,000 miles for every 10 barcodes you mail in, and he found that he could buy these trial size pudding cups for 25 cents, and they all had their own barcode.

    3. TFTim Ferriss1:28:20

       [laughs]

    4. CHChris Hutchins1:28:20

       And so he drove hundreds of miles around, filled up a van, bought over 12,000 pudding cups, donated all the pudding cups to local shelters with the requirement that they would need to, as they serve them, give him back all the tops that they peeled off so he could mail them in. And he ended up earning, I can't remember how many miles it was. It was enough miles that he said he spent seven years burning through them, taking friends around the world, going on amazing trips.

    5. TFTim Ferriss1:28:47

       [laughs]

    6. CHChris Hutchins1:28:48

       He got to write off the pudding as a donation. His total cost was like $2,500.

    7. TFTim Ferriss1:28:53

       [laughs]

    8. CHChris Hutchins1:28:54

       It's just a great example of learning to spot places where promos or credit card rewards can be pretty lucrative.

    9. TFTim Ferriss1:29:04

       Mm-hmm.

    10. CHChris Hutchins1:29:04

        And so if anyone was around in the mid-2000s, the US government kind of passed some legislation to get this $1 coin in circulation. They basically said, "We've gotta get this coin in circulation," and so they basically let you buy dollar coins from the US Mint website for $1, and you could put them on a credit card. You would go on, and you... A- and the idea was coins last longer than bills. The government said a $1 coin would save us $5 billion over 30 years-

    11. TFTim Ferriss1:29:34

        [laughs]

    12. CHChris Hutchins1:29:34

        ... because it would last. We didn't have to reprint all these bills. They sold $1 coins, shipping included, for $1, and this one guy, I don't know his name, bought $2.5 million of dollar coins.

    13. TFTim Ferriss1:29:48

        [laughs]

    14. CHChris Hutchins1:29:49

        He said they weighed, like, 40,000-plus pounds, and so he would just get these coins to his house, and he would throw them in his car, wheelbarrow them to the bank, deposit them as US dollars, and just cycle through, earning millions and millions of credit card points buying coins on his card. I think that's an extreme version of points arbitrage, right? A lighter version is just I spend a lot of money on Amazon. I mean, let's not use Amazon 'cause Amazon has a credit card that gives you 5%. But let's say you spend a lot of money at Apple, and you're at the checkout line at the grocery store, and there's an Apple gift card, and you could just buy your Apple gift card at the grocery store, load it up to your Apple account. But because you have a card that earns 4X points on groceries, you get 4X on Apple instead of one because you bought the Apple gift card at the grocery where you get elevated points. Looking at places where you can move around your spending or buy things that are easy to sell on a card, great options.

    15. TFTim Ferriss1:30:47

        Let me throw one out for you just because... You may already know this, but I think it's a fun story, even though [laughs] the conclusion is a little unclear to me. Did you ever hear the story about Kyle Bass, well-known hedge fund manager, and his nickel purchase?

    16. CHChris Hutchins1:31:03

        No.

    17. TFTim Ferriss1:31:03

        Did you ever hear about this?

    18. CHChris Hutchins1:31:04

        I do not.

    19. TFTim Ferriss1:31:05

        Okay. So I just looked it up, and now this is on some random website, so who knows. Fact check everything, folks. But [laughs] here it is. In 2011, hedge fund manager Kyle Bass reportedly bought $1 million worth of nickels. Why on earth [laughs] would anyone want to own 20 million nickels? Let's work out the underlying logic of this trade. A nickel weighs five grams, 75% of which is copper, the rest is nickel. At the time that Bass bought his nickels, the actual metal content of each coin was worth around 6.8 cents. [laughs] So Bass was buying 6.8 cents for 5 cents or 1.36 million worth of base metals for just $1 million. And it goes on. There are a bunch of [laughs] important points in the fine print here, right? 'Cause he's not gonna wanna melt it down himself. Is it even legal for him to do that? Maybe not. So does he have exposure then to the ni- you know, the nickel and copper markets? How does it work? But still Kind of a neat example of how some of these opportunities seemingly, and, you know, make sure you're not too clever by half 'cause you can shoot yourself in the foot financially, but it's like, this kinda makes for a

31. 1:32:12 – 1:34:18

    How Chris saved $11,000 on his wedding by bartering with points.

    1. TFTim Ferriss1:32:12

       fun story.

    2. CHChris Hutchins1:32:13

       The last story was that, and this goes back to my early, earliest days of buying pizza in college. When we were getting married, we had no idea how expensive things could be at a wedding. This guy who was kind of a successful entrepreneur in Silicon Valley had this amazing wedding video he shared, and I was like, "Well, that was really cool. I'd love a wedding video like that." So I looked at who produced it, and I emailed them, and they were like, "Yeah, we'd love to do your wedding." I was like, "Awesome. How much is it?" And the woman was like, "It was like $13,000." I was like, "Uh, no. Sorry. I thought a wedding video would be like a fun thing to have, but $13,000 was like a meaningful portion of our entire wedding budget. I can't spend this on a wedding." And I'd been talking to this woman, unfortunately, for like three or four calls before I knew the price. And she was like, "Ah, but your wedding sounds fun. You're a cool person. I'd love to do it." And I was like, "Yeah, I don't know what to tell you." And I had been talking about our honeymoon, and we were going to the Seychelles, and that was the plan for our honeymoon. And she was like, "Gosh, it would be fun to do your wedding." She's like, "Man, I just, I'd love to hear the story of how your honeymoon goes. I've always wanted to go to the Seychelles." And I was like, "Really? You've always wanted to go to the Seychelles?" The street price of two business class tickets to the Seychelles is like $20,000. But the actual cost to me in miles is like $2,000. So I offered her, I said, "Look, what if I sent you and your husband to the Seychelles in business class whenever you wanna go? We'll find a time where the flights work. I will book you there. You will save $20,000 if you otherwise would've bought the ticket. I'll do it with points. What do you think?" And she was like, "Let's do it." And so she agreed to do the wedding. The only cost we had was we paid for the hotel rooms for the videographer 'cause that was a real cost. But all the time cost and editing cost she ate. And it turns out at the time she wanted to go, it was harder to find the Seychelles, so we sent her and her husband from Colorado to Mauritius in business class. They had an amazing trip. I would say the lesson here is, you know, you can always find ways to negotiate anything. That's one of my principles.

    3. TFTim Ferriss1:34:17

       So that seems

32. 1:34:18 – 1:37:41

    Using points for gifts and business benefits.

    1. TFTim Ferriss1:34:18

       to me that might be the golden move that I could apply without inflicting much brain damage, right? 'Cause I work with dozens of contractors for a million different things, and I could say, "Okay, how about instead of paying you rack rate retail for your services, which is 10K, right? I sent you on this trip, which is 15K," if in fact they want to travel or whatever it is, since that's gonna be seemingly the highest conversion, right? I could probably do that a handful of times and squeeze a lot more value out of these points than I would for myself over time since I don't, I just don't foresee traveling with a high enough frequency. It would take a long time to kind of drain the bathtub before it's refilling, so to speak.

    2. CHChris Hutchins1:35:12

       Yeah.

    3. TFTim Ferriss1:35:12

       But if I'm using it also to find opportunities to pay for folks or give them something, I wonder what the tax implications are of that. Who the fuck knows? Yeah, what does, how does that work from a gift tax perspective? Do they get themselves into trouble? I guess that's a problem for them and their accountants.

    4. CHChris Hutchins1:35:32

       I don't have an answer to that.

    5. TFTim Ferriss1:35:33

       Yeah.

    6. CHChris Hutchins1:35:34

       But I would be very surprised if you bought a flight for someone and it ever... If you asked your accountant, they might say like, "Uh, it seems fine." I'm not an accountant. I'm not gonna tell you what to do. I'm sure someone listening will tell you there are tax implications.

    7. TFTim Ferriss1:35:51

       Yeah. I suppose, well, it's different from a gift because it's a barter effectively.

    8. CHChris Hutchins1:35:55

       Yes.

    9. TFTim Ferriss1:35:56

       So there are probably specific elements of the tax code that deal with bartering. I have no idea what they are.

    10. CHChris Hutchins1:36:02

        What is the value of the thing you're giving and all that.

    11. TFTim Ferriss1:36:05

        Mm-hmm.

    12. CHChris Hutchins1:36:05

        Another option, though, for anyone who's a business owner, right, you know, it's like, oh, I could give all my employees a $1,000 bonus, or I could send them all on a $5,000 vacation that cost me $1,000 worth of points.

    13. TFTim Ferriss1:36:18

        Hmm.

    14. CHChris Hutchins1:36:18

        That employee is gonna have this incredible experience. Pick any luxury resort that's in the Hilton portfolio. Amex transfers one to two to Hilton.

    15. TFTim Ferriss1:36:29

        Hmm.

    16. CHChris Hutchins1:36:29

        24 million Hilton points, you're like, "Where do you wanna go on vacation?"

    17. TFTim Ferriss1:36:32

        Yep.

    18. CHChris Hutchins1:36:33

        It's like a gift to employees, to family members. One of the interesting things is you probably have less flexibility in your schedule, but maybe you have family members or friends or nieces or nephews or graduation gifts.

    19. TFTim Ferriss1:36:46

        Yep.

    20. CHChris Hutchins1:36:46

        I heard this great story. A friend of mine gave his son for graduation. He's like, "Right after graduation, you tell me. I'll send you anywhere you wanna go in the month after you graduate." Well, he had all the flexibility. Like, he didn't start his job for a month, so he could... You know, it didn't matter what day, it didn't matter what time, and he and his best friend, he flew he and his best friend to Asia. That was his graduation gift.

    21. TFTim Ferriss1:37:05

        How hard is it to transfer points to someone else, right? I've got 12 million points. If I was like, "Here's a competition-"

    22. CHChris Hutchins1:37:11

        You don't need to. That's the thing.

    23. TFTim Ferriss1:37:12

        What do you mean I don't need to?

    24. CHChris Hutchins1:37:14

        So you can do two things. You can book a flight in the Amex portal for anyone, right? You can transfer those Amex points only to your loyalty account, but you can book it for anyone.

    25. TFTim Ferriss1:37:24

        I see.

    26. CHChris Hutchins1:37:24

        So you could transfer those membership rewards to Air Canada and book a flight for anyone in the world on any flight that Air Canada is partners with. I think Air Canada has the most airline partners of any airline in the world, I think. So Air Canada is like a great target for Amex points.

33. 1:37:41 – 1:40:49

    How Chris would optimize point resources in my shoes.

    1. TFTim Ferriss1:37:41

       So what would you do in my shoes right now, right? Because we talked about the long-haul international. We talked about using the different tools that you've already outlined, right, for checking for flights, AwardTool, A- Amex Travel Portal, et cetera. Talked about getting a business gold card for more advertising. Anything else that is easy for me to do or have my assistant in the Philippines help with doing? But like if it chews up a few hours of my time, I will probably have an allergic reaction. Is there anything else where you'd be like low-hanging fruit Do or don't do these additional things. Get rid of this card, that's bullshit. Do this. This is hurting you more than helping you.

    2. CHChris Hutchins1:38:22

       I know that on your list you have over a million Capital One points that you've earned on... After back and forth with you and trying to look at pictures, I still can't figure out what card it's earning points on. But it earns just one point on every dollar.

    3. TFTim Ferriss1:38:35

       Yeah.

    4. CHChris Hutchins1:38:35

       So at a minimum, it's like if you just got a two on everything or a cash back. Like, I would encourage you to maybe just switch to Bank of America Premium Rewards card. Get 2.6% cash back on everything, 3.5% cash back on travel and dining. Like, stop worrying about these points. [laughs]

    5. TFTim Ferriss1:38:56

       That requires me to have 100K in a bank account there or no?

    6. CHChris Hutchins1:39:00

       The most optimal would be open up some brokerage account, throw 100 grand in treasuries, and not worry about it.

    7. TFTim Ferriss1:39:05

       Yep.

    8. CHChris Hutchins1:39:06

       The easiest would be open up a checking account that earns almost no interest. That would be some opportunity cost. But if that's even too much for you-

    9. TFTim Ferriss1:39:14

       Yep

    10. CHChris Hutchins1:39:14

        ... go open the Fidelity card that gets 2% on everything, and you don't have to move money anywhere. There are multiple cards that earn 2% or 2X point. Capital One has a Spark cash on the business side, and then a Venture card, which is just 2X points on everything on the personal side.

    11. TFTim Ferriss1:39:34

        Okay, cool.

    12. CHChris Hutchins1:39:35

        There are a lot of options, but for you and everyone listening, everyone listening should not be getting less than two points or 2% on any transaction because you're just giving money away. Let me caveat. Unless you're in the middle of rebuilding your credit, and you're not eligible for all these cards, caveat one. Caveat two, no amount of the 19% to 29% APR that most of these cards are charging is worth any of these points. We should have, like, rewind. Anyone that's thinking about optimizing their credit card game, if you can't pay your balance off in full each month, it is not worth it. Stop, do not pass Go. Do not do any of these strategies.

    13. TFTim Ferriss1:40:12

        [laughs]

    14. CHChris Hutchins1:40:12

        If you can pay your card off each month and you have enough credit score to get a card that earns 2X or 2%, that is the floor.

    15. TFTim Ferriss1:40:21

        Mm-hmm.

    16. CHChris Hutchins1:40:22

        Anything earning less than that, it's too easy to earn 2% or 2X points on everything to have any excuse of doing anything else. But I might have 30 cards, which is a little insane. The difference between two and 30 is very minor.

    17. TFTim Ferriss1:40:39

        [laughs]

    18. CHChris Hutchins1:40:39

        The difference between one and two is pretty decent.

    19. TFTim Ferriss1:40:42

        Yeah.

    20. CHChris Hutchins1:40:43

        So I would say finding the two cards that optimize is really the gold standard.

34. 1:40:49 – 1:42:33

    The joy (and livelihood) Chris gets from sharing a day in his life.

    1. TFTim Ferriss1:40:49

       Yeah. I mean, I just have to give credit again where credit is due, but you've turned your obsession/sport/optimizer's [laughs] curse also into your business, right? So there is actually much more so than the average duck walking around doing this behind closed doors an upside to you to experiment, which is what you like doing in the first place. So it's a, it's a very beautiful solution [laughs] that checks a lot of boxes, so congratulations again on that.

    2. CHChris Hutchins1:41:20

       I feel lucky that I basically just started recording a day in the life of myself. It's like, today I'm gonna go down the rabbit hole of every card that Citibank has and, like, break down every little feature and why there's a couple real ways that you could basically earn top-tier Citi status not too difficultly. Great. That's an episode. Let's deep dive on gold. Let's deep dive on award travel.

    3. TFTim Ferriss1:41:42

       Which is legitimately a day in the life.

    4. CHChris Hutchins1:41:44

       That is what I wanna do.

    5. TFTim Ferriss1:41:45

       Yeah. [laughs]

    6. CHChris Hutchins1:41:46

       And I get to share it.

    7. TFTim Ferriss1:41:47

       Makes me think of, I think in the first episode I did with Chris Sacca a million years ago, investor who's now a billionaire. Crazy story, but embracing your... Fully embracing your weird self, right? Like, there is a lot to that that we could unpack in a completely separate episode.

    8. CHChris Hutchins1:42:06

       Funny enough, the last I saw you was in Austin at the live Dig Nation, and I saw Chris Sacca there, who heard me talking about gold, and he was like, "Can I just come with you?" Like, there's still a part of him that he's like, even at his level of wealth, he's like, "Dude, I wanna do this. Like, I wanna go resell gold."

    9. TFTim Ferriss1:42:24

       [laughs]

    10. CHChris Hutchins1:42:24

        Like, he just, like, loves the arbitrage opportunities.

    11. TFTim Ferriss1:42:27

        Oh, for sure.

    12. CHChris Hutchins1:42:27

        So there's something fun about knowing you kind of got one over the system.

    13. TFTim Ferriss1:42:31

        Yeah. Oh, for sure.

35. 1:42:33 – 1:49:37

    Pondering AI’s future impact

    1. TFTim Ferriss1:42:33

       What do you think the future looks like here? Any hopes? Any expectations? I mean, you track this. Not to use this incantation as a catchall for everything, but certainly my frequency of using AI tools has, has gone up 10X in the last two months alone.

    2. CHChris Hutchins1:42:51

       Yeah.

    3. TFTim Ferriss1:42:51

       And a lot is gonna change, and I would imagine maybe just like high-frequency trading and so on affected the investing game, and obviously prior to that, a lot of the quant stuff out of places like RenTech and whatever. Are the arbitrage opportunities going to vanish with the smoothing over of sort of robots who are attempting to do the same thing that a lot of people are doing semi-manually right now? Do you think there's gonna be a lot of amazing stuff coming? I mean, what do you see when you... or hope for when you look into your crystal ball with travel stuff or points stuff?

    4. CHChris Hutchins1:43:29

       I think there's a couple tailwinds and a couple headwinds. So on the tailwind side, one of the challenges with having all of these points is that these programs are always devaluing things all the time, and so there used to be amazing opportunities to do X, and now it costs 20% more. One of the nice things is that the government kind of is doing some sort of, like, we're gonna investigate whether airlines are devaluing people's miles. And so there's currently some sort of investigation going on. So I think we are unlikely to see a lot of devaluing coming in the near-ish future because there's some scrutiny about that. So that's positive. There is this Credit Card Competition Act that's been tried to be passed. The idea being... We didn't talk about this, but the way all of this is funded is that when you swipe your credit card, there is a fee that the merchant pays to use your credit card.

    5. TFTim Ferriss1:44:20

       Yeah.

    6. CHChris Hutchins1:44:21

       And that fee gets split between the payment processor, like a Stripe or a Square or lots of other ones, the issuer, and the network. So Visa, MasterCard is the network. The issuer is your Chase. Those fees pay for this. In a lot of other countries, that interchange is capped. I think in the EU it's capped at .3%, and in the US it can be as high as 3%.

    7. TFTim Ferriss1:44:43

       Yep.

    8. CHChris Hutchins1:44:44

       The Credit Card Competition Act is like, in my personal opinion, a bad attempt at trying to make this better in that it doesn't... I, I'm not gonna go into the nuance of what it does, but the senator who created it has tried to attach it to this Crypto Genius Act that, by the time this comes out, maybe we know the fate of it anyways. But there are some people trying to create legislation to bring down the interchange rates, create more competition. If interchange was .3%, you would not be earning all these cash back and points on anything.

    9. TFTim Ferriss1:45:13

       Mm-hmm.

    10. CHChris Hutchins1:45:14

        That's why cards in Europe are much less lucrative, if not completely foreign concept. If that happens, great. The reality is it seems like merchants are not going to all of a sudden drop their prices if their fees go down. Like, we've seen multiple cases with tariffs, with other things, that that's not usually the behavior that happens. So that's on the, the points side. I think it's become a lot easier to use your points with all these tools, and I think AI will make those tools even better. You'll just be like, "I wanna go to Japan," and it'll be like, "Boop, boop, boop, boop, boop, boop, boop, based on everything you have, based on everything that's out there, here's the optimal way to do it." On one hand, that's kind of a bummer for the people who understand the system now. If everyone can understand the system, then those outsized return options are less. That said, one of the ways that outsized value comes is from still doing things that are like, "I'm not gonna look from SF, I might look from the West Coast."

    11. TFTim Ferriss1:46:14

        Mm.

    12. CHChris Hutchins1:46:14

        "I don't care where I'm gonna stay. Find me the best deal." So I think it'll be a while before the average person thinks that way.

    13. TFTim Ferriss1:46:20

        Mm-hmm.

    14. CHChris Hutchins1:46:20

        I think the average person, whether an AI tool's doing the searching or not, is like, "I wanna go here. How do we go to Paris in June?" Not, "What's a great deal I could get? And I'm willing to buy a ticket to Austin and fly to Paris from Austin if that's awesome on a separate airline and a separate ticket."

    15. TFTim Ferriss1:46:38

        Yeah.

    16. CHChris Hutchins1:46:38

        I think AI keeps blowing my mind every month, so who knows? Maybe it'll understand all of this and help us all redeem our points in way better ways, and maybe this scrutiny will prevent airlines from devaluing and we'll all win. But I still think there will always be edge cases around how to do it and ways to find the optimal inventory flights that will leave some upside for those of us who spend a little bit more time being ahead of the curve, and I'm glad that it's easier for more people to do that.

    17. TFTim Ferriss1:47:07

        Mm-hmm.

    18. CHChris Hutchins1:47:07

        Like, it was really hard 10 years ago to get crazy value. Now it's easier. I think it'll get a little easier, but I still think there'll be a lot of upside for people who pay attention to what's going on.

    19. TFTim Ferriss1:47:19

        Mm-hmm.

    20. CHChris Hutchins1:47:20

        As for travel in general, I'm not sure what AI's influence will be on airlines and hotels and all that. I haven't really thought too deeply about it. It seems like it solves a lot more aspects of my life than leisure travel or even business travel.

    21. TFTim Ferriss1:47:37

        Big question mark for me. Not the slightest clue, frankly. I mean, I'm hoping it can reduce a lot of friction, but how it does that, what the form factor is, how people interact with it, no idea at this point. So TBD.

    22. CHChris Hutchins1:47:53

        I was talking to someone, and they were like, "On Booking.com, this website said the room had two beds, and on all the other portals it said it had one. And then I called the hotel, and they were like, 'We have two.'" Like, so some story like that. It's like the moment you have a travel scenario where AI booked the wrong thing, you're like, "I would rather just do this myself."

    23. TFTim Ferriss1:48:11

        Yeah.

    24. CHChris Hutchins1:48:11

        Get to the airport, and the flight was wrong. It was on the wrong day. I don't know. I'm not gonna let an AI book my travel. But I might like it, let it do some exploration. I do think when it comes to itinerary planning, if anyone is planning a trip anywhere and is not using AI to think about where to go, what to do-

    25. TFTim Ferriss1:48:25

        Oh my God, it's incredible. Unbelievable

    26. CHChris Hutchins1:48:29

        ... that is incredible.

    27. TFTim Ferriss1:48:31

        Yeah.

    28. CHChris Hutchins1:48:31

        Like, plan my 10-day vacation in Japan, the AI tools for planning trips are, are just out of this world. So I would, I would use it for inspiration and, "Oh, I want a place cold. Oh, I'm traveling with my kids. Oh, that's too much travel. Oh, can I take a train between these two cities?" That kind of stuff, it's just so good.

    29. TFTim Ferriss1:48:48

        Incredibly helpful. Yeah, I used it. I was in Japan visiting my host family I stayed with when I was 15, actually. [chuckles]

    30. CHChris Hutchins1:48:56

        Wow.
36. 1:49:37 – 1:52:48

    Hotel relationship building.

    1. TFTim Ferriss1:49:37

       powerful. What have we left out, Chris? What, what should we talk about? Any glaring omissions?

    2. CHChris Hutchins1:49:42

       I've got a couple things. One, there are some people who are like, "I'm into it. I wanna play this game, and I wanna get the most out of it," or, "I've been playing it and I wanna level up." And there are people who are like, "I don't want to." There's still gotta be something I can do. And I would say a couple tricks that I think for people who like to travel that don't require any amount of points arbitrage, credit card anything, is one of my favorites is if you book your hotel directly with the hotel, which outside of getting a deal or cashing out points, I would encourage you to book directly with the hotel because they, they see your profile, they see your name, they see that you have some loyalty. They wanna build relationships. Email the hotel after you book, and then maybe follow up three or four days before you arrive and just tell them you're coming. Tell them you're excited to stay with them. Ask them a question. I have seen I don't know what the percentage, but at least 100 people have sent me photos of something that's happened, whether it's an upgrade, whether they did something really nice in the room for their kid's birthday. Someone had their initials monogrammed in their pillow, which was kind of a weird thing to do. [laughs] Bottle of champagne, free drinks at the restaurant. At the end of the day, the hotel game is still a hospitality game, and if you give people a channel by which to build the relationship, I've been amazed at the payoffs of doing that. So if you can't find the email, ask ChatGPT. If they can't find it, call the front desk and say, "Hey, is there an email for someone at the hotel?" And just say, "Hey, I'm coming. I'm excited to stay with you guys. We haven't been to Italy ever, and, you know, we're celebrating my son's birthday." You don't need to ask for anything. Just let them know you're coming, and, and I would be surprised if at least every other time you do that, something doesn't surprise you.

    3. TFTim Ferriss1:51:29

       Yeah.

    4. CHChris Hutchins1:51:29

       And the hotel doesn't find a way to do something nice.

    5. TFTim Ferriss1:51:32

       Let me add just two things to that also. When you check in, there's no harm in asking, you know, "Just out of curiosity, are there any up- upgrades available?" You can just ask, because stuff happens, as you know, all the time, and it doesn't hurt to ask. And I've also had some crazy, crazy [laughs] upgrades. Nothing to do with my name, actually, because I usually book under an alias anyway. Long story, I won't get into it, but just for privacy and security and bullshit. And the craziest type of upgrades. It's like, if you're just friendly and they happen to have something that opened up and it's last minute. I mean, I've had... I remember at this one hotel, booked a, a decently nice room, nothing like crazy, super over the top. But it was just like chatting them up, having a good time checking in. I was in a good mood, travel was easy, blah, blah, blah. And then asked if they had an upgrade and ended up getting a penthouse suite, which was the entire floor, right? [laughs] Just because they're like, "Well, it's kinda like a zero if, if we don't sell it. It's like 5:00 PM. Nobody's coming to use this thing." And was able to have this incredible experience. Invited a bunch of friends over fr- who lived in the same city, and it was just outstanding. So it's like, you can

37. 1:52:48 – 1:53:50

    Insider restaurant hacks.

    1. TFTim Ferriss1:52:48

       also ask. One last tip. This is for restaurants, and I've got a whole bunch of these in The 4-Hour Chef for people who are interested. But I used to work in restaurants, right? Bussing, waitering, et cetera, on Long Island mostly growing up. If you just ask people if they have a two-top or a four-top, right, like a two-person table or a four-person table. If you use that type of language, very often you will get better service and get upgrades and all sorts of stuff. So [laughs] that's another easy one.

    2. CHChris Hutchins1:53:18

       Love that.

    3. TFTim Ferriss1:53:19

       Happens a lot too if you sit at the pass, which I love to do anyway. And when I was working on The 4-Hour Chef, it's like I would wanna sit at the pass. The pass is where the dishes that have been prepared are often put under a heat lamp or they're put up with their ticket so the servers can come and get them. And a lot of restaurants will have a handful of seats that are effectively at the pass so that you can watch what's happening in the kitchen. And if you specifically request that, which is not a very common request, again, very often you get much better treatment. So just some ideas.

38. 1:53:50 – 1:56:18

    Signup bonuses and credit score impact.

    1. TFTim Ferriss1:53:50

       What el- what else do you have?

    2. CHChris Hutchins1:53:51

       So I realize someone might be listening to this thinking, "Okay, Tim's got millions of points. Chris has millions of points. I actually wanna take these vacations. Like, I wanna go on these trips. I don't have millions of points."

    3. TFTim Ferriss1:54:03

       Make a wedding video for Chris.

    4. CHChris Hutchins1:54:05

       Yeah. [laughs] You spend some money, but you don't spend hundreds of thousands of dollars a year. So how do you even end up with this many points if you're not running a business?

    5. TFTim Ferriss1:54:12

       Yep.

    6. CHChris Hutchins1:54:12

       And I would say one thing that is one of the ways most people I know rack up points, and I've got so many stories from listeners who are like, "Hey, I just got into this thing, and I've already been able to take this amazing vacation, this amazing everything." So like I've got... I could go through a long list of people who are like, "I'm three months in, and I just took my wife on this amazing thing that we never got to do our honeymoon," et cetera. One of the ways that people accelerate the game is whenever you open up a new card, there might be some kind of offer. Oh, 100,000 points, 75,000 points. While I often say 2X points is a great return on your spend, I will say that if you look at the top, and this I did a couple months ago, but if you look at the top 15 signup bonuses or welcome bonuses right now, earn 75,000 points for spending $5,000, that kind of thing. The average return on spend, valuing the points at just a penny, we're not, not even giving the outside, is about 17%. If you open up a new card and they offer you 100,000 points for spending $5,000, right, that's 20X return on that spend. And so those new card offers are 10X, maybe in this case 20X more lucrative than your regular spending. And so when I tell people that, their first question is, "Okay, but am I just gonna ruin my credit if I open up two or three cards a year?"

    7. TFTim Ferriss1:55:36

       Yeah, exactly. That was my next question.

    8. CHChris Hutchins1:55:38

       And there's this great tweet that, because I haven't seen someone put this visually, and I will send you a link to it. I don't know this person, Chad Janus, he's on Twitter. He opened up this card, and he's like, "My wife and I opened up 26 cards in 2017. We earned 2 million points and traveled to 40 countries for free. That year of traveling changed our lives. Most people ask, 'What happened to your credit score?' What do you wanna know?" And he showed this chart where his wife Hannah, her credit score went from 670 to 798.

    9. TFTim Ferriss1:56:06

       [laughs]

    10. CHChris Hutchins1:56:07

        And his went from 794 to 805.

    11. TFTim Ferriss1:56:09

        Huh.

    12. CHChris Hutchins1:56:10

        So I just wanna dispel this myth of, you know, opening up a handful of cards, totally torching my

39. 1:56:18 – 1:59:26

    Card closure strategy and credit history preservation.

    1. CHChris Hutchins1:56:18

       credit. So what I will say is, what you don't wanna do, and I should've said this earlier, if you've had a card for 20 years and you just realized in this episode that it's the worst card you've ever had and it earns nothing.

    2. TFTim Ferriss1:56:30

       [laughs]

    3. CHChris Hutchins1:56:31

       I wouldn't go out and cancel it, because one of the components of your credit score is the average length of credit history.

    4. TFTim Ferriss1:56:37

       Oh.

    5. CHChris Hutchins1:56:37

       So what you don't wanna do is close the card that you've had for 20 years that's like the anchor in that average.

    6. TFTim Ferriss1:56:43

       Hmm.

    7. CHChris Hutchins1:56:44

       What you could do is just leave it open.

    8. TFTim Ferriss1:56:46

       Now wait, question for you. When you cancel, because I'm glad you said that, 'cause I was like, "Oh, I'll kill my-" ... Capital One card and hop to whatever. If I were to close down the Capital One card, which I've definitely had for probably 20 plus years.

    9. CHChris Hutchins1:56:57

       Yep.

    10. TFTim Ferriss1:56:58

        I think it was, might have been my first credit card because [laughs] long story. Believe it or not, I wanted to work at Capital One when I was gonna graduate from college. Didn't get the job. Probably a blessing in disguise, but no offense to Capital One, but they were doing amazing stuff with direct marketing at the time, which was interesting to me. Anyway, if I were to close that, does it remove that entirely from my average or does it just stop it so that now it's 20 point whatever years and it's not gonna keep growing?

    11. CHChris Hutchins1:57:26

        I believe your average age of credit is only looking at the active lines.

    12. TFTim Ferriss1:57:32

        Oof. Brutal. Okay.

    13. CHChris Hutchins1:57:34

        There are a lot of things that you should not do. Before you close a credit card, I think there's kinda three choices you can make. One, if there's no annual fee, you just leave it open.

    14. TFTim Ferriss1:57:43

        Yeah.

    15. CHChris Hutchins1:57:43

        There's not a lot of risk. Like, just leave it open. In the Capital One case, you can product change it to another card more often than not. So you could call Capital One and say, "What are my options for this card?" And they might say, "Oh, you could move it over to a Venture card and earn two points per dollar on everything. Would you rather have that card?"

    16. TFTim Ferriss1:58:01

        Yep.

    17. CHChris Hutchins1:58:01

        And you could just change it to another card that you do want.

    18. TFTim Ferriss1:58:04

        Mm-hmm.

    19. CHChris Hutchins1:58:04

        Now, the counter to that is if you wanted to get that 75,000, 100,000 point signup bonus on a card, you won't get it when you change cards.

    20. TFTim Ferriss1:58:13

        Yeah.

    21. CHChris Hutchins1:58:13

        So you could be better off just opening that other card up and leaving the Capital One card there. So if it has no annual fee, you can just leave it there. My ritual, I, I would give you two options. One, put one recurring charge that's small on it and set it to auto-pay. Put your Spotify subscription. That way, they never close it for inactivity.

    22. TFTim Ferriss1:58:32

        Yep.

    23. CHChris Hutchins1:58:32

        Or I have this ritual where around the holidays I just kinda, like, go through all the old cards and I just make sure I put a charge on each of them.

    24. TFTim Ferriss1:58:39

        [laughs]

    25. CHChris Hutchins1:58:39

        My oldest card was a United card that I got in college, and I didn't use it for four years and they just closed it.

    26. TFTim Ferriss1:58:45

        Mm.

    27. CHChris Hutchins1:58:45

        And I was pretty bummed.

    28. TFTim Ferriss1:58:46

        [laughs]

    29. CHChris Hutchins1:58:47

        I could have avoided that. Or if that charge has an annual fee, you can usually product change it down.

    30. TFTim Ferriss1:58:52

        Yep.
40. 1:59:26 – 2:02:05

    Amex Platinum Card evaluation and optimization.

    1. CHChris Hutchins1:59:26

       that they could do for you.

    2. TFTim Ferriss1:59:27

       Let's do a retrospective real quickly then on my Amex. So I signed up ages ago, I mean, 20-plus years ago, for Platinum, in part, and this is where AI is gonna change things also, because you and I spoke about this. At the time, as I remember it at least, it gave you access to Amex Platinum Concierge, and I used the fuck out of that thing. Like, I had them put together reports. I was like, "I'm considering getting a high altitude simulation tent." This was for [laughs] the 4-Hour Body research. [laughs] "And I want you to look at, you know, identify the four or five best models." This is back in the day, right? This is probably 2008, 2009. And they put together the most excellent, it was unbelievably good, like, 10-page Word document and send it to me. And so I would use the concierge service for things like that. I don't know if it continues to perform at that level because I have other tools at my disposal now. But is the... I think it's, what, $175 a year, something like that, is probably the annual charge?

    3. CHChris Hutchins2:00:38

       The Platinum Card now I think is 695.

    4. TFTim Ferriss2:00:40

       Oh, fuck me. Okay, so it's 695 a year. All right. Is that worth it, or in what cases is that worth it? Or should I just product down to gold and call it?

    5. CHChris Hutchins2:00:50

       Yeah, I would say the concierges have been less lucrative in recent past than before.

    6. TFTim Ferriss2:00:55

       Yeah.

    7. CHChris Hutchins2:00:56

       And on the personal side, the personal Platinum, the primary benefit of it is you'll get a Priority Pass membership or you can go to Amex Centurion lounges. Priority Pass is like a lounge network-

    8. TFTim Ferriss2:01:07

       Yep

    9. CHChris Hutchins2:01:08

       ... at airport lounges. I only use my Amex Platinum Card for flights. My wife and I each have one. Obviously, we could put all our flights on one of them. So I believe that I am able to take the coupon book of perks that the Amex Platinum gives you and get more value than the annual fee. But I would say knowing you and how many hoops I don't think you wanna jump through, you probably wouldn't.

    10. TFTim Ferriss2:01:31

        Yep. [laughs]

    11. CHChris Hutchins2:01:32

        The question would be, like, do I spend enough on flights that holding this card to get elevated points on flights is worth it? On the business side, I think you should absolutely keep it because redeeming your points is gonna be worth 1.54 cents if you have the Business Platinum versus 1 cent if you don't. Just booking flights, no hassle, no searching for availability, just booking it with Amex Travel using your points.

    12. TFTim Ferriss2:01:55

        Mm.

    13. CHChris Hutchins2:01:56

        On the personal side, I don't know. I only use my personal Platinum Card for booking flights. You could downgrade it to a Gold card and not have it drop off your credit. Another important

41. 2:02:05 – 2:04:39

    Annualcreditreport.com.

    1. CHChris Hutchins2:02:05

       thing, most business cards don't show up on your credit report. So if you've had a business card for 20 years that you don't use and it doesn't show up on your credit report, which by the way, Annualcreditreport.com, it's not a scammy website. It's like a real... It sounds like a scammy website. [laughs]

    2. TFTim Ferriss2:02:22

       Sounds scammy.

    3. CHChris Hutchins2:02:23

       But it's like a government-sanctioned website that lets you just check your credit report I think every week.

    4. TFTim Ferriss2:02:28

       Annualcreditreport.com, is that your phishing site to steal everyone's email addresses?

    5. CHChris Hutchins2:02:34

       You can get a free credit report every week from Annual Credit Report. It's authorized by the government. You could see what cards are on there. You won't get your credit score. Most credit cards give you a free credit score. Credit Karma gives you free credit scores. There is a difference between the FICO score, which is like a private company that looks at your credit report and comes up with a score, and then the VantageScore, which is an alternative. You can go down my credit report score episode if you wanna go down there, but yeah, I would say you could go look. But business cards won't have an impact when you cancel them because they usually don't show up on there.

    6. TFTim Ferriss2:03:08

       So question, looking at... Credit score is something I feel like I can wrap my head around. What good is my credit report without a credit score? What are you looking for in that?

    7. CHChris Hutchins2:03:20

       So your credit report is literally just a list of all the accounts, their status, the, you know, recent balance, all that kind of stuff on there.

    8. TFTim Ferriss2:03:29

       Mm-hmm.

    9. CHChris Hutchins2:03:30

       I would encourage people to freeze their credit report because it prevents other people from opening up credit in their name. I would remind you that if you're gonna apply for a credit card, you should unfreeze it while you do that, or you will most certainly not get approved because they need to access your credit report. But the report is the thing. What happens is there's a company called the Fair Isaac Corporation, which is FICO. They basically look at your credit report and then have an algorithm that creates a score that makes it easier for lenders to make decisions off of, so the lender doesn't have to analyze this multi-page document.

    10. TFTim Ferriss2:04:04

        Oh, wonder what'll happen to that with AI.

    11. CHChris Hutchins2:04:07

        What a person would do with their credit report is just, does everything on here look good?

    12. TFTim Ferriss2:04:11

        Yeah.

    13. CHChris Hutchins2:04:11

        Is there any credit I don't recognize? Are there cards open I didn't know were there? But practically, there's not a lot you do with your credit report.

    14. TFTim Ferriss2:04:20

        Yeah. Got it.

    15. CHChris Hutchins2:04:21

        Don't cancel your oldest cards. Open new cards if you see an awesome bonus. For me, 75,000-plus points is a pretty lucrative bonus, so I like that. And you can product change cards, so if you have a card and you don't really care about earning a new bonus, but you just wanna have something different, you can change it around.

42. 2:04:39 – 2:06:16

    Doubling bonuses with your spouse.

    1. TFTim Ferriss2:04:39

       How important is it for long-term marriage stability for both people to be either into or not into all this type of arbitrage? [laughs]

    2. CHChris Hutchins2:04:51

       I got some flack from someone in a podcast review 'cause they got mad that I referred to my wife as a player, too. They're like, "We're not living in a simulation. This is not a video game" and-

    3. TFTim Ferriss2:05:01

       [laughs]

    4. CHChris Hutchins2:05:01

       In the points and miles world, the player terminology is just, like, standard nomenclature, but-

    5. TFTim Ferriss2:05:07

       Mm-hmm

    6. CHChris Hutchins2:05:07

       ... it is very common for people to have one person who's, like, the primary and another person who's kind of like, "Just tell me which card to use." And I would say this is a fun game in that one plus one often equals more than two. So when you sign up for a card, you get a bonus. Sometimes you can refer someone, they get the bonus, and then you get the bonus for referring them. So I know lots of couples who will, like, both open a card, but one will refer them, and they'll end up with, like, two and a half times as many points 'cause of the referral plus the signup. And if there's a great 100,000-point bonus, two people can have it, right? They're completely separate on, on your credit report 'cause they're separate people. Playing the game with a partner can be fun. I will advise you something that I have learned, eh, the hard way-ish. Just keep your spouse as informed as they want to be. Sometimes I've had fun conversations with my wife, and she's like, "Is this the credit card that you opened without talking to me?" You know, like-

    7. TFTim Ferriss2:06:07

       [laughs]

    8. CHChris Hutchins2:06:07

       I was like, "No, no, no, I talked to you about it." Like, I would say keep them as informed as they want to be, but if you're open... You don't need both people to be as involved

43. 2:06:16 – 2:09:31

    Chris’s travel enjoyment philosophy and spending mindset.

    1. CHChris Hutchins2:06:16

       in the game.

    2. TFTim Ferriss2:06:16

       Here's a maybe overarching question that seems important, and that is, what have you found to contribute to enjoying travel? Because this whole thing seems to kind of hinge on traveling, by and large, right? Some form of travel, right? And it seems like you get the most bang for the buck if it's long-haul international travel. Which means if you don't enjoy those trips, there are some questions that come up about why you're playing the game to begin with, right? Why are you a player? And maybe it's for the love of the arbitrage, and that's actually the part that you enjoy more than the redeeming of points. But let's just say that you're using the outcome to drive the process rather than simply enjoying the process. What have you learned about enjoying, enjoying travel, and are you able to enjoy travel once you're traveling, or are you also constantly looking for, like, price arbitrage and getting the most value out of it?

    3. CHChris Hutchins2:07:19

       I think the bulk of the trip is the cost of the lodging and the cost of the flights. And so once we're there, I'm not thinking about it that much.

    4. TFTim Ferriss2:07:26

       Yeah.

    5. CHChris Hutchins2:07:27

       Like, I'm just trying to enjoy the place we're at. And in some ways... Like, we're about to go to the new Waldorf Astoria in Costa Rica, and in some ways I'm like, look, the rooms were free. We used six Hilton free night certificates. The flights were free. We used United and American points. So if we're gonna spend, like, what is probably an overpriced amount of money on food, so be it, you know? Like, everything else was free. So in some ways, it helps me enjoy the trip even more.

    6. TFTim Ferriss2:07:54

       Mm.

    7. CHChris Hutchins2:07:55

       Now, I did decline. They were like, "Do you wanna go on this tour of the rainforest? You could do it by helicopter, and it's only an extra $9,000." We declined it. Like, I wasn't so in the moment that I was willing to spend anything, but it's freeing.

    8. TFTim Ferriss2:08:07

       So let me, let me push on that a little bit. Like, you could... It would hurt you psychically to do it, but you could do that. Practically speaking, have you ever had an opportunity to do that before? And when do you think the next opportunity would be? Like, is that not something, in the interest of a life fully lived, if you can afford it, you'd have to stomach it, but, like, you could withstand the financial cost, why not do that?

    9. CHChris Hutchins2:08:35

       So I did an episode with Bill Perkins, who wrote a book called Die with Zero.

    10. TFTim Ferriss2:08:38

        Yes.

    11. CHChris Hutchins2:08:38

        And so this comes to me very strongly. It was one of my favorite episodes. And I think that if there were an experience that I thought was going to really be magical, I would be willing to spend that number of dollars. In this case, it was like, do you wanna go on a two-hour drive or take the helicopter for $9,000? And I'm like, I don't know. I haven't been to Costa Rica in 20 years. My wife's never been to Costa Rica. I'm sure it's also interesting from above, but sometimes driving two hours in another country is also interesting. Stop at a random restaurant on the way. So it didn't feel like the experience was so much better. It almost seemed more like, well, if you just don't wanna spend two hours exploring this country.

    12. TFTim Ferriss2:09:21

        Mm.

    13. CHChris Hutchins2:09:22

        So in that case, I don't think it would've made sense. But in other cases, if that's just what it costs to do a thing that I really wanna do, I'm

44. 2:09:31 – 2:11:03

    Paying cash vs. points at the Four Seasons.

    1. CHChris Hutchins2:09:31

       okay spending it.

    2. TFTim Ferriss2:09:31

       What's the last example of you just paying straight cash, no points, no miles, but like splurging on something where you're like, "Totally fucking worth it. Would do it again"?

    3. CHChris Hutchins2:09:43

       I was talking to someone, and he was like, "We recently went to The Four Seasons in Lanai." And he's like, "It was everything I ever wanted a hotel experience to be. The hotel was perfect." And he took his kids, we have two kids, and I was like, "That sounds magical." And I was like, "We don't have any plans for spring break." I was like, "I wanna go to The Four Seasons in Lanai." There's no points deal for The Four Seasons. They don't have a loyalty program. Like, there are ways. We have this hotel program on our site where you can get some perks, like you get a free breakfast, but there's no way to get the price of the hotel covered other than just cashing your points out and spending money. Like, there's just no trick.

    4. TFTim Ferriss2:10:21

       Yeah.

    5. CHChris Hutchins2:10:22

       But something stuck with me, which like, this is the best experience. It's everything you ever want a hot- I was like, "I want to feel that."

    6. TFTim Ferriss2:10:28

       Mm-hmm.

    7. CHChris Hutchins2:10:28

       And so we just paid cash. Like, we just went to the hotel, we paid cash. When we ate meals, we paid cash. Like, did we use a luxury hotel program to make sure we got certain extra bonuses included? Sure. Did we get $100 property credit? Yeah. But when we went to... They have a Nobu there. Did we not order what we wanted to eat because we had to pay for it? No. We just spent all the money we wanted. We just decided that this three-night stay at this hotel, we are just going to not worry about the cost, and we're gonna do what we wanna

45. 2:11:03 – 2:13:22

    Learning how to spend money as a frugal person.

    1. CHChris Hutchins2:11:03

       do.

    2. TFTim Ferriss2:11:03

       What did that feel like for you? I have so many questions, but just as someone who does that not incredibly frequently, right? What did that feel like for you guys? Was it like, "Wow, it's so nice not to have that analytical overlay of all the other stuff"? Was it like, with every bite you're just like, "Oh, God," getting a slight punch in the testicles?

    3. CHChris Hutchins2:11:25

       10 years ago, it would've been a slight punch in the testicles.

    4. TFTim Ferriss2:11:28

       Did you have, like, an expense hangover where it's like, you know, you got home and you felt like you just did a bender in Vegas and you're just like, "Ah, fuck." You know, "Seemed like a good idea at the time"? I'm just wondering how it felt.

    5. CHChris Hutchins2:11:38

       Honestly, the takeaway, my wife was like, "We should do that again."

    6. TFTim Ferriss2:11:42

       [laughs]

    7. CHChris Hutchins2:11:42

       "That was great." We just didn't think about it. And I will say, one of the nicest things about that experience that makes it even better is that hotel, during the time we went, they were doing some construction, so they were like, "Oh, activities are included." And, and it... You'd be surprised at how many higher-end properties, like, don't nickel-and-dime everything. It's like, "Oh, we include free breakfast," and like, you could just eat whatever you want. It's not the Marriott free breakfast where you get a $15 certificate off the meal. And you go to the pool, and sunscreen and aloe are just free-flowing. You don't have to buy them at the gift shop, and-

    8. TFTim Ferriss2:12:18

       Yeah

    9. CHChris Hutchins2:12:18

       ... stuff like that. Your room has bottles of water. In a way, we kind of paid for it at the beginning, and so once we got there, most of the expense was covered, and that's... There's this book, Happy Money, and in it, one of the five kind of scientific ways to spend money that make you happier is to prepay for things.

    10. TFTim Ferriss2:12:38

        Mm.

    11. CHChris Hutchins2:12:38

        It's like when you pay for this hotel in advance and a lot of the stuff's included, you don't even really think about it.

    12. TFTim Ferriss2:12:44

        Mm-hmm.

    13. CHChris Hutchins2:12:44

        That was really nice. Do I want every vacation to be as expensive as that vacation? No. Do I want every vacation to be that great? Yes. And so it's a balance.

    14. TFTim Ferriss2:12:53

        Mm.

    15. CHChris Hutchins2:12:53

        I know that staying at Cap Rocat was a similar experience. If anything, it was maybe even nicer, but we didn't have the kids. It was a different, different vacation. And we did do that one with points. So, like, it's a balance. You kinda alternate between the two. But I think it's given us permission to spend, which learning the art of spending, learning how to spend money as a frugal person is hard, and we could probably have another two-hour conversation about that topic.

46. 2:13:22 – 2:14:32

    High-quality experiences over extreme optimization.

    1. TFTim Ferriss2:13:22

       Yeah.

    2. CHChris Hutchins2:13:22

       And I think I've slowly learned how to spend money at levels that are probably still behind the average for someone in my situation. And I think it's easier to do when the experience is something that I just know there's not an alternative. It'd be really hard for me to spend $10,000 a person on a flight to Japan in business class because I just know how to get that exact flight, maybe with more constraints, but I know how to get that exact same thing.

    3. TFTim Ferriss2:13:51

       Mm-hmm.

    4. CHChris Hutchins2:13:51

       But restaurants is a good example. I have no issue going to a restaurant and spending a lot of money on a meal. There's not a way to do it more optimally. Am I using the right card to get the most points? For sure. I'm optimizing where I can, but I'm not choosing to only go to the restaurant that I could buy a gift card on sale for.

    5. TFTim Ferriss2:14:10

       Mm-hmm.

    6. CHChris Hutchins2:14:11

       If you go all the way back to the beginning, my goal wasn't to save money, 'cause I could just not eat the pizza. My goal was to get the pizza like everyone else and not have to pay for it.

    7. TFTim Ferriss2:14:20

       [laughs]

    8. CHChris Hutchins2:14:21

       Or get the best deal for it. So at the end of the day, I still operate on the principle, I wanna do the thing I wanna do. I don't wanna sacrifice the quality of life, the quality of the experience. Sometimes you can do it,

47. 2:14:32 – 2:17:05

    Bill Perkins and Die with Zero

    1. CHChris Hutchins2:14:32

       sometimes you can't.

    2. TFTim Ferriss2:14:32

       Yeah. Let's hop back to Bill Perkins for a second. So you mentioned Die with Zero, subtitle Getting All You Can From Your Money and Your Life, and I'll just give a quick line on it. The question, since I'll buy you some time, is gonna be what most stuck with you or stuck out to you about your conversation with Bill? Very interesting book. I've read it. Here's the description. This is diewithzerobook.com. So, "Die with Zero by legendary energy trader Bill Perkins details the thought-provoking framework for maximizing net fulfillment over net worth." And I believe this is from memory but that believe Bill used to work with John Arnold, who's a fascinating character. There's a really great interview of John Arnold on Peter Attia's podcast actually, who was also a legendary energy trader, became America's youngest billionaire in 2007 at the time. Super genius. But coming back to Bill Perkins, what, what is the basic premise of the book as you would describe it? And what stuck with you or stuck out to you about that conversation or the book?

    3. CHChris Hutchins2:15:41

       The biggest principle is we're all saving money and, and we usually have this attitude of like, "I'm gonna save it and spend it in retirement." Most people end up not spending as much as they think they will because they, you know, their bodies can't do all the things that they once wanted to spend their money on, and lots of people end up with more money than they wanted, and we should use that money, and we should ideally use it at times of our lives when we can get the most out of it.

    4. TFTim Ferriss2:16:08

       Yeah.

    5. CHChris Hutchins2:16:08

       And there's a bunch of concepts in there, like the concept of memory dividends, where it's like you actually benefit from doing this thing earlier because you can relive the moment, retell the story, share it with the people you went on it and, you know, look at the pictures forever. And it was a very light bulb moment for me because I had always been, like, tracking net worth, grow net worth, have more, have more, and at the end I was like, "Oh." I left the interview and I was like, "Why am I doing that?"

    6. TFTim Ferriss2:16:34

       [laughs]

    7. CHChris Hutchins2:16:35

       In fact, we took a trip. At the end of the interview, he challenged me to do something, and we literally planned a trip right after the interview. We were like, "Let's just spend the money. Let's go on the thing." And everything kind of changed, and I was like, "Why save more?" Like, obviously if you don't have any savings, it's good to save, but if you do have savings, what's the upside of having more money when it could be using that money now and not kind of looking at the scoreboard? And so

48. 2:17:05 – 2:18:28

    Coast FIRE (Financial Independence Retire Early).

    1. CHChris Hutchins2:17:05

       I think we started thinking if we've put aside enough that our savings can grow to what we will need whenever we stop working, and there's this concept of Coast FI or Coast FIRE, which is, you know, you could go search and dig into that, then we should really be spending our money instead of saving it.

    2. TFTim Ferriss2:17:26

       Wait, wait, wait, hold on. So Coast FIRE. Now, FIRE is the Financial Independence Retire Early, right?

    3. CHChris Hutchins2:17:32

       Yes.

    4. TFTim Ferriss2:17:33

       What is Coast FIRE?

    5. CHChris Hutchins2:17:34

       Coast FIRE is this idea that I haven't saved up enough that I could stop working today.

    6. TFTim Ferriss2:17:38

       Mm-hmm.

    7. CHChris Hutchins2:17:39

       But I've saved up enough money that I don't need to contribute to my savings, right? If you're 35 and you have a million dollars in the bank and you wanna work till you're 60, if you don't touch that million dollars, it's probably gonna be more than enough for you to retire. So you probably don't need to keep contributing to your savings. So you can adjust your life so that you can coast into retirement.

    8. TFTim Ferriss2:17:59

       I see.

    9. CHChris Hutchins2:18:00

       And maybe that means stop doing the really hard job that pays a ton of money and do the easier job because you don't need the extra money to contribute to your savings. Or maybe it means stop saving and spend more.

    10. TFTim Ferriss2:18:12

        Is the underlying or one of the underlying assumptions there that that million dollars in, is invested in a low-cost index fund with a basket like the S&P 500, something like that?

    11. CHChris Hutchins2:18:23

        That would be the principle, is like my money will grow at some reasonable rate.

49. 2:18:28 – 2:21:51

    Books for developing a conscious, fulfilling relationship with money.

    1. TFTim Ferriss2:18:28

       What books or thinkers have you found... Like, if you were gonna give people a few books, not many, right, but a few books. Let's just make them books for the time being. Books that you would give someone to help them develop a aware, like, a conscious approach to money and also a fulfilling relationship with money, right? Which is not automatically the same thing as the former, right? Any books come to mind?

    2. CHChris Hutchins2:19:00

       So I like Happy Money, which is a really short read. It's the science of smarter spending. It's just, like, five ways you can spend money that actually lead to happiness based on some research. I like Sahil Bloom's book, The Five Types of Wealth, 'cause it just reminds you-

    3. TFTim Ferriss2:19:15

       Mm-hmm

    4. CHChris Hutchins2:19:15

       ... that wealth isn't just about money.

    5. TFTim Ferriss2:19:17

       Yep.

    6. CHChris Hutchins2:19:18

       So often we get caught up in this world of, like, money is wealth, and there's a lot of things that go into being happy and wealthy and all this stuff that just aren't money.

    7. TFTim Ferriss2:19:28

       Yeah.

    8. CHChris Hutchins2:19:29

       Morgan Housel's got a new book, The Art of Spending Money, which I think is gonna be interesting based on his past book. Before you mentioned specific money, I was like, a lot of the books that I really like thinking about are, like, From Strength to Strength, which is an Arthur Brooks book about happiness.

    9. TFTim Ferriss2:19:45

       Yeah, that's fair. I mean, it's all tied together.

    10. CHChris Hutchins2:19:48

        Like, I think if you think too much about money, you just lose sight of the fact that money is a tool to help you achieve things, and if you don't have any, it's a really important tool, but as you have more, sometimes it just becomes a thing that you focus on way too much.

    11. TFTim Ferriss2:20:01

        Yeah.

    12. CHChris Hutchins2:20:01

        And if you can learn to be happy with whatever you have, you might not need to chase, and that chasing is, like, so toxic. It's so... It's such a challenge for everyone in that rat race and, I don't know, I, I think this isn't a book, but go dig into, like, the Bureau of Labor Statistics. Go, go, like, look at how people actually spend their money because I think what you see on Instagram isn't reality. And so if you base all your assumptions on how people spend their money on data that is not true, you might think you're not in a good place. And then if you go actually look at, like, what does a household with my amount of, you know, wealth or income typically spend on based on actual data that the US government publishes and gives you for free, you'd be like, "Oh, wow, not everyone in my situation is spending $100,000 on a vacation and chartering jets and all this crazy stuff that I see on the internet."

    13. TFTim Ferriss2:21:02

        [laughs] Yeah, totally.

    14. CHChris Hutchins2:21:05

        So-

    15. TFTim Ferriss2:21:06

        Uh, you, you know, I feel like there should be a term There's a term called orthorexia which can be applied to people who are basically unhealthily obsessed with physical fitness or appearance, right? So ortho, the same ortho you would find in orthopedics [laughs] and then rexia, just like anorexia, right? So orthorexia. I'm wondering if there's a term for being unhealthily obsessed with money. I was looking up in Latin, that's pecunia, I think. I'm sure I'm pronouncing that incorrectly. But, like [laughs] pecuniarexia, there's gotta be a word. There's gotta be a good one. If, if not, I mean-

    16. CHChris Hutchins2:21:45

        I feel like AI could answer this question fast.

    17. TFTim Ferriss2:21:47

        AI will answer that question quickly. I'll let people play with it.

50. 2:21:51 – 2:23:53

    Limits of universal financial advice.

    1. TFTim Ferriss2:21:51

       Where do you disagree with, say, Bill Perkins? Was there anything that you remain philosophically, not opposed to in a judgemental way, but where you are simply using a different OS in your own mind? Is there anything that hops out?

    2. CHChris Hutchins2:22:06

       I mean, one of the biggest criticisms that he gets is he has so much money, you know? So, like, it's easy-

    3. TFTim Ferriss2:22:12

       Right

    4. CHChris Hutchins2:22:12

       ... to be like, "Let's spend all my money. I have it." And so I think if there's one thing that it might be missing, it's how do you bridge the gap to the stage in your life where Die with Zero is not an option. You know? Like, you don't have a plan yet to get to that point. There's this book that comes out in a couple months called The Wealth Ladder, and it's like these different stages of wealth and what life looks like at each stage and what the priority at that stage is. And I think the criticism I might give is you can't write a book for every stage. And so someone who's at, like, that first stage of wealth, it's like they just need to get out of it. They need to have any amount of savings to cushion them from their car breaking down, from some medical emergency, and Die with Zero is not a relevant conversation. And so I think Die with Zero is a relevant conversation if you are in a financial situation to save more money than you make, and you've built up a nest egg, and now you can start to think whether the amount of money you're saving is enough to change your behavior. But it's not earlier in your... Like, it wouldn't have been that relevant to me 25 years ago.

    5. TFTim Ferriss2:23:22

       Yeah. Brilliant title, too. I mean, Die with Zero, it's a very provocative position, and I found myself nodding in agreement with a lot of what was in that book. And I think, I believe in almost any field, I've said this before, but it's like the extremes inform the mean but not vice versa, right? So you can really glean a lot from what people might consider extreme positions. Have you ever read The Man Who Quit Money by Mark Sundeen?

    6. CHChris Hutchins2:23:50

       No.

    7. TFTim Ferriss2:23:51

       I highly recommend.

51. 2:23:53 – 2:28:18

    Chris’s potential alternative career paths.

    1. TFTim Ferriss2:23:53

       What is described in the book I wouldn't model exactly, but it raises a lot of really good questions. Just like after you had Bill on, you got off and you were like, "Wait a fucking second," like, "Why am I doing X?" Right? Like, let me step back and ask a couple of questions that didn't even seem necessary to ask, and this, this book is quite similar, so I'll just read a little bit. Mark Sundeen, S-U-N-D-E-E is the author, but The Man Who Quit Money, and here's the description. I've actually read this book multiple times, which says something. Very fun to read, super strange. So here's the description. "In 2000, Daniel Suelo left his life savings, all $30 of it, in a phone booth. He has lived without money and with a newfound sense of freedom and security ever since. The Man Who Quit Money is an account of how one man learned to live sanely and happily without earning, receiving, or spending a single cent. [laughs] Suelo doesn't pay taxes or accept food stamps or welfare. He lives in caves in the Utah canyonlands, forages wild foods and gourmet discards. He no longer even carries an ID." [laughs] And it goes on and on and on. [laughs] It's so extreme but, uh, very eye-opening because it starts to poke at these base assumptions that we have, which we do not realize are assumptions half the time because they're so present, right? It's a fun read, raises a lot of worthwhile questions.

    2. CHChris Hutchins2:25:17

       I think some people think the more you talk about and know about money, the more you think about it, and I'm like, nope. I'm very much the passive index investor. It's like, let's put the money in, let it grow, and like we started talking about stuff, like, let's focus on either making it or enjoying life and all this stuff. So I try to set most of my finances on pretty autopilot so that I don't have to think about the money on a day-to-day basis. And that's not to say it's not important to know how much you're spending and what you're saving and all those things, but it's not something where I'm, like, logging into a brokerage account every day and doing all that kind of stuff.

    3. TFTim Ferriss2:25:54

       Let's pretend that you can't do all the hacks anymore. Podcasting isn't a thing, or at least podcasting, websites, you, you cannot play the content game in the way that you're currently playing it. If you had to start another company or get a job working another company of some type, what might you do? 'Cause you've tried a bunch of different stuff, and I appreciate how you think about things very deeply. So if you couldn't do what you're currently doing, and you couldn't create a clone of it, you can't do anything that's, like, a close cousin, what might you do would be on the short list?

    4. CHChris Hutchins2:26:39

       If I couldn't do this right now, I would probably take every little tiny idea I have and try to, like, build the product to solve the thing with all that AI can do right now.

    5. TFTim Ferriss2:26:48

       Mm.

    6. CHChris Hutchins2:26:49

       But interestingly, when I ended up at Wealthfront as a product manager, I told people, I was like, "I think I could do this job for 40 years." Like, the idea that my job is to go talk to people, consumers, understand their perspectives in a space I care about and just build products to make their lives easier, that was awesome.

    7. TFTim Ferriss2:27:09

       Yeah.

    8. CHChris Hutchins2:27:09

       The idea that we're just gonna build products that simplify something that is complicated for other people so that- They can just get on with their day and, and focus on their life and not get caught up on it. I think if the podcast never happened, I would still happily be in that job.

    9. TFTim Ferriss2:27:25

       Yeah.

    10. CHChris Hutchins2:27:26

        So I don't have the kind of ego of I have to work for myself. I need to go do my own thing. I think I, I just like building stuff, and so I'd be building something. I don't know what that is, and a couple of the ideas I've had in the recent past are all kind of tangential to what I'm doing, so they feel like a cop-out if I told you, "Oh, I just start a blog reviewing financial products." It's like, well, it's kinda like similar to what I'm already doing. Or build a future travel agency. Yeah, well, we kinda do that on the si- Like it... I don't know what that would be. Everyone always tells me, "Chris, you should go launch a credit card 'cause, like, you have all these opinions." But I think at the end of the day, the economics to make it work and be competitive just require an immense amount of scale that I, I don't know if I have it in me to go do that thing, like give up 10 years of your life to go build this crazy thing. I'm not

52. 2:28:18 – 2:29:28

    The fisherman parable.

    1. CHChris Hutchins2:28:18

       compelled.

    2. TFTim Ferriss2:28:18

       Sounds really unpleasant. I mean, what would be the reason to do it? Sounds very uncompelling.

    3. CHChris Hutchins2:28:24

       I don't know. I feel very much like the Mexican fisherman a little bit, where it's like there was a time in my life, and for anyone who doesn't know this parable, which I'm guessing you've referenced in the past-

    4. TFTim Ferriss2:28:33

       Version of it was in The 4-Hour Workweek, yeah

    5. CHChris Hutchins2:28:35

       ... the idea that this guy's a happy fisherman living his life, fishing all day, hanging out with his friends, spending time with his family.

    6. TFTim Ferriss2:28:42

       Playing guitar over beers at night with his family and friends.

    7. CHChris Hutchins2:28:45

       Exactly.

    8. TFTim Ferriss2:28:45

       Yeah.

    9. CHChris Hutchins2:28:45

       And someone's trying to convince him to go build a bigger and bigger fish company, and then he's like, "And at the end, what do I do once I've done that?" He's like, "Well, now you can hang out with your friends and fish and go drink beers." And he's like, "Well, that's what I'm doing already." I don't think I have a thing that's compelling me to be the business person in that story right now, and until there is, I don't like forced entrepreneurship, like s- forcing myself to build a thing 'cause it's what I should do.

    10. TFTim Ferriss2:29:09

        Mm-hmm.

    11. CHChris Hutchins2:29:09

        And I would probably spend a bunch of time playing around with tools and data until I found a thing that pulled me in that direction. And until then, I'd happily go find a company working on a problem space that I'm interested in as a product person and just building products in that space.

53. 2:29:28 – 2:31:01

    Parting thoughts.

    1. TFTim Ferriss2:29:28

       Amazing. All right, Chris, where can people find what you're up to? What would you like to point people to?

    2. CHChris Hutchins2:29:32

       I have a podcast. We talk about all these things. Every topic that I probably brushed on, I've probably gone deep on, and it's called All the Hacks. You can find it anywhere, wherever you're listening to this. Everything I do is at chrishutchins.com or allthehacks.com. It's the same URL. And every week, I send a newsletter on Saturday morning that's just all the stuff I'm finding. Where are points on sale? What routes on certain airlines are going on promos right now? What's changing? So if you don't wanna go so far down the rabbit hole, but you kinda wanna stay on tune of where the deals are, you can sign up at allthehacks.com.

    3. TFTim Ferriss2:30:14

       Well, Chris, thank you very much for the time. I have a, a copious amount of notes I'm gonna have to sit down and figure out what exactly my next steps are, which I think I have some inkling of. So might have to chat with you again to do post-game analysis a little bit on some of this. But thanks for taking the time, man. I really appreciate it.

    4. CHChris Hutchins2:30:30

       Yeah. I hope people that are listening can just earn more and make good value out of it and live happier lives. Thanks for having me.

    5. TFTim Ferriss2:30:41

       Yeah, absolutely, man. And folks, we will have all links to everything in the show notes, as per usual, at tim.blog/podcast. Just search Chris's name, and it'll be easy enough to find him. And as always, be just a bit kinder than is necessary to others, but also to yourself. Until next time, thanks for tuning in

Episode duration: 2:31:22