YouSaid · the spoken record

Chris Hutchins

lines on the record: 169
first: 2025-06-10
most recent: 2025-06-10
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“So 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. 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 because it was like actually saved over if we had paid cash. So it was amazing.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“And we ended up at this amazing resort in Mallorca last year called Caprocot. 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, well, that looks beautiful. If you want to go in the summer, it's like two to five thousand a night. 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, it's going to be a lot harder to find a good deal. So instead, we search 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 going to get you on these long haul routes.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“Seats.arrow, 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. You can book using United Miles in first class for 165,000 points. 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 that'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 flew first class on Lufthansa. But like you could basically just schedule a, I'm going to take an amazing trip. I'm going to”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“If we did it this way, I said the best deals are with the ultimate flexibility. So you could say, hey, just blow my mind, make me feel like I got so much value out of this. What could we do? What could we do that's really awesome? Block off a week and say this week, I'm just going to blow it out of the water and I'm going to do something awesome. And I don't know what that's going to be. I don't know where it's going to be. And you go to one of these tools and you say, where can I go this week? I think you could have a good time anywhere. So for example, great.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“And Emirates is not part of any of the major alliances. They have some partners, but because they have the escape valve of transferring them to Marriott, I would just be done. But if you had some Air France miles, you could probably use them even if you weren't going to France to book a Delta flight. Or if you had British Airways to book an American flight or something like that.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“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, which is a Greek airline part of Star Alliance. And I was like, what do I do with these miles? I'm not going to 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 on United. Now, 6,000's not enough to do that, so I wouldn't even worry about it. But if you had...”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“Whenever you fly on tap, you should just put in your united number, right? Like 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 want to 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 then you don't have to worry about having these little balances all over the world in random airlines.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“I have in the past with American, I've donated a thousand miles. That's activity. 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. Emirates, for example, lets you transfer your Emirates points to Marriott. So funny enough, it's like you've got Marriott points. They need some activity or they're going to 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. cash out your Emirates balance. With Tap Air Portugal, you know, you've got an orphaned $6,500, probably not even enough to book really anything. I honestly wouldn't feel too guilty just letting them expire. 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.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“There's multiple things. So most of the programs in the US now don't expire. If you have the credit card with a company 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, A&A, 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. And so in the case of Airlines where if there's no activity, they expire loyalty.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“Give me your points. 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 and this applies to anyone listening. Just go look. What would it cost on United? Let's just book it with United this time. And it's often great deals. Like 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 since 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. It's like all inclusive and you can use your Hyatt Points there. You don't have anything that would get you high up points. So it's not relevant to you.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“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. Like all the points his company earns, he uses to book trips 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 could reach out and be like, hey, we could help put these to use if you don't want them.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“That's one, it's a very charitable cause. It provides no value. To you, I don't even think you get the tax write off, but you're helping people relocate with miles you don't need.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“Looks like they have a it's with sad hearts we share this news. So there might be some ways to use them for like someone else, something like that.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“I just looked and they shut down, and so I don't know if there's going to be an alternative, but there is a company that used to exist called Miles for Migrants that basically you hand over your miles and they help like refugees relocate around the world using your miles.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“Sometimes it just feels good to take a free trip. Who cares if it's a good deal? You went on a trip you weren't gonna take otherwise.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“And so the good news is with United, if you want to book five seats in business class to Japan, it's going to be easier to find five seats. It's not going to be as good of a deal. But you know what? If otherwise you're not going to use them, why not?”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“Like, there's no point in cashing him out for a box of chocolates. On United, you can only use them to book United and their partner's flights. 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. 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 or their profile.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“One cent of value from each of those points, 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, could you do better? Yeah. But I'd rather use that, do that five times, save 40 grand or something. You know, like it's still a good deal. 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 award tool, will show you United. We'll show you Delta and America. They're not just showing you what you can do with your Amex points. 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 least one cent.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“I would say the same principle applies, right? If you look at United, you have United Delta American and Alaska are both part of the One World Alliance. Delta is part of the Sky Team Alliance and United's part of the Star Alliance. Those cover almost, I don't know, if I had to guess like 90% of all long-haul flights you would ever take in your life. And so if whoever's looking to book your travel, you're like, oh, you want to go to Japan way better than any other redemption is just, okay, well, United flies nonstop to Japan, depending on what city you're in. So does a Delta and American, you're going to get at least probably”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“That you will one in probably somewhere between five and ten times find a great deal with your points. And the other four out of five, nine out of ten times, you won't. And that over the long haul, you'll get a blended rate of your points of probably like somewhere between like 1.7 and two cents, because that one time you might get five cents. And then the other times you'll get one and a half cents. And over the course of the next five years, you'll burn through all your points. You'll get twice to three times as much value as you would have using Amazon. And hopefully whoever's helping manage your travel can just like have this principle of search for points, don't find it, use points on Amix. Doesn't work. Pay cash.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“My sequence would be find something like a ward tool and say, I'm going on this trip. Let me search it on a ward tool. Can I use my points? Because chances are you're going to get two to five cents per point on a good award redemption. Nothing on award tool or any of the tools you end up liking. Nothing on award tool? Great. I'm going to go to the MX travel portal and I will book it with my points because you have an Amx business platinum. If you're booking it in business class or with whichever single airline you choose like Amex lets you pick one airline for your annual airline credits, whichever one you pick, you can book an economy also. You book it with points. They'll give you 35% of the points you spend back as a refund. It's the perk of the business platinum card. And you'll effectively get 1.54 cents per point. So I would tell you my guess is that if you're not that flexible with your travel,”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“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. You know, like now you might not like that last minute, like, I don't know exactly if I'm going to take the flight I planned on. But within two weeks of departure, all kinds of stuff happens. You can get on Lufthansa first class. You can get on direct flights. 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 going to get 150 seats on the plane. 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 going to be going to the same place. So not as fun.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“And I'll set an alert and say if two seats open up in business class on the direct flight or four seats, send me an alert and then I'll go book that and cancel the other one. And maybe I have to pay the $12 fee. And so the way most people I know do this is they book something that's good enough. Not optimal. Set an alert and almost always end up with something better. To the point that...”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“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 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. So what I will often do is say, look, we really want to go to destination X. 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, award tool, points, yeah, seats.errow is another one if you're like a spreadsheet nerd. It's like a little bit more database than user-friendly, but it's really powerful.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“So, a general rule here, which I'm just going to 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.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“80% confidence that by the time we take off, we're all going to be in business class on one flight. I'm about 80% confident.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“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. As an example, this trip we're taking to Japan next year, Japan Airlines releases two seats on every flight 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 Haneta. 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. Like the change fee might be $25 on the airline we booked Couldn't even get four seats on the same flight playing the game as optimally as we wanted.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“Let's address the biggest challenge with getting the most out of these points. Airlines do not release every seat available for use with points”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“Like, 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 like once in a lifetime, it'd be somewhere between like 130 and 15 one-way flights. So let's call it 65 to 75 round trip flights in business class over an ocean.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“We've been to the Conrad, which is a chain within Hilton. The Conrad Borabora, an amazing property. We've been twice now. We're about to go to the new Waldorf Astoria in Costa Rica. 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. 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 just to give people mind $12 million. What does that mean? Could be 200 nights at like an incredibly high end, beautiful resort.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“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. If, and I think you do have an Amex business platinum, right? You could just book your flights with points in the travel portal. You're capped at how much you can do a year. But if every year you used up to 2.85 million, which would take you about, you know, five and a half, six years, you'd get $187,000. So more than the $120,000, right? And then If you transfer them and booked aspirational things with airlines on long-haul international, I think you could get reasonably 250 to 600,000 dollars of value. So that's the range. But what should Tim do?”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“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. Got 12 million Amex points. The easiest thing you could spend them on Amazon, they'd be worth $85,000. You could just book flights. They'd be worth $120,000.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“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. Like five years ago, I'd say, you know, it's tough. Now I'd say, if you were like, I want to go to Europe this summer. We want to book it more than a month out and we're kind of flexible where we go. You can get incredible value that will make a cashback card look like a poor return. But if every time you travel, you're like, I want to fly on this date. I don't want to change planes and I want to go to this city and I want to book it three months out. I don't want to have to think about it after that. You probably would be better off doing cashback the whole time.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“Obviously, that assumes that you have the ability to put $100,000 in a brokerage account. You can just invest it in U.S. treasuries. Like you can move over a Roth IRA. You don't have to like have some Merrill Lynch broker manage your portfolio, but I would say that is the most scalable thing. I know people with large limits can spend lots of money, don't have cards held up and transactions not post and points disappear. That, I think, is a solution. If you want something even easier, Fidelity has like a 2% cashback card. 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 like I'm flexible in every vertical, right? Like you could be flexible that”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“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. That's gone. Robin Hood has a card that's 3%. But 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 an Arel 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, premium rewards elite cards, it bumps up travel and dining spend to three and a half percent. So everything you spend on travel and dining, three and a half percent back, everything else, 2.625%.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“So U.S. Bank launched this amazing 4% card. You had to put $100,000 in a brokerage account. And then they were like, oh, wow. Isn't profitable”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“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 crashback card and getting 2.625%, which I think is like a good target cash back and never having thought twice about points at all.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“Just turns it into dollars depending on the card, what the rate is between point eight 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 like you just have the money. So I will say that is an option.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“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. And it's not going to take any more work to go on Amix'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 one 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. You could just transfer all your points to your brokerage account.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“I earn these things. They are not dollars. Why not spend them flying Emirates first class, taking a shower in the sky, eating caviar and sipping champagne? Like, why not do that? Because it's not like I'm dipping into my kids' college fund, where it might feel differently if they had earned cash back the whole time.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“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. Now, I could poke a hole in that and say, if you just used a cashback card the entire time, instead of having 12 million points, you probably would have been sitting on $300,000, 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. Whereas if they had 12 million points that in their mind 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”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“Or four times the cost in the number of points you'd need. And so that's where you're going to get the most value. 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 points.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“That anyone's going to 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, 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. really nice luxury resort might be 10 times the cost of, you know, the holiday in downtown, but it might only be”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“American Express Capital One, Citibank, Wells Fargo now, Chase. Amex will let you move your points to 18 different airlines. So you could move your Amex points to Delta. You can move them to Air France. You can move them to Air Canada. And so the reason why people love them is when we go back to these tools and you're searching, gosh, I want to find a good deal to Europe. Well, sometimes that good deal might be a deal with Air France. Sometimes that good deal might be a deal on United, but it's even better deal if you book it through Air Canada, which is a partner of United. And so 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. That said, the best value.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“So we'll break the landscape into there's two obvious buckets that people are going to be familiar with. You have airline miles that are linked to a program. So you have some Alaska, some American, some Delta, and some United for major U.S. carriers. Got hotel points. I'm not going to tell you what to do with yours because they all expired. And then you have bank points. And I'm going to 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.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“They're hoping for breakage. They're hoping you redeem you get all these miles, you never use them I think the original models were 60% would get used.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“United Airlines sold almost $4 billion worth of miles as part of their business is a little old data, but back in 2019, it's probably only gone up from that. And if anyone remembers during the pandemic, 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 all three airlines put their loyalty programs up. That was the collateral and raised, depending on the airline, like $6 to $10 billion each using the loyalty program as their collateral.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“Those banks so that they can give them to the card holders. And so the business of selling those points is massive. 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 U.S. 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.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“Delta came out and said, I think it was a year ago. They said in 2023, 1% of US GDP went through a Delta Amax card. So the transaction volume on Delta Amax cards was 1% of GDP. Or I think they said just shy of 1% of GDP. They didn't give an exact number. 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.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT
“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. So everything that is united that is not the loyalty program is worth negative $12 billion. And so there's this common understanding in this kind of point smiles 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.”
2025-06-10 · The Tim Ferriss Show · #815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse · IDENTIFIED FROM THE TRANSCRIPT