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

“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. To 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.”
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
“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. 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.”
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 don't care where I'm going to stay. Find me the best deal. So I think it'll be a while before the average person thinks that way. I think the average person, whether an AI tool is doing the searching or not is like, I want to 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. I think AIs 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. Like it was really hard 10 years.”
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 that happens, great. The reality is it seems like merchants are not going to all of a sudden just like 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 point 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 want to go to Japan and it'll be like 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, you know, 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 going to look for MSF. I might look from the West Coast.”
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
“Stripe or a square or lots of other ones. The issuer and the network. So Visa MasterCard is a network. The issuer is your chase. And so those fees pay for this. In a lot of other countries, that interchange is capped. So like I think in the EU, it's capped at 0.3%. And in the US, it can be as high as 3%. So the credit card competition act is like, in my personal opinion, like a bad attempt at trying to make this better in that I'm not going to 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 0.3%, you would not be earning all this cash back and points on anything. That's why cards in Europe are much less lucrative, if not completely foreign concept.”
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 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, you know, 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 going to 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. And that fee gets split between the payment processor, like a”
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
“Funny enough, the last I saw you was in Austin at the live indignation, and I saw Chris Saka 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 want to do this. Like, I want to go resell gold. Like, he just like loves the arbitrage opportunity. So there's something fun about knowing you kind of like got one over the system.”
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 feel lucky that I basically just started recording a day in the life of myself. He's like, today I'm going to 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 city status not too difficultly. Great, that's an episode. Like, let's deep dive on gold. Let's deep dive on award 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
“19 to 29% APR that most of these cards are charging is worth any of these points. So 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 is not worth it. Stop. Do not pass go. Do not do any of these strategies. If you can't 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. 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. Might have 30 cards, which is a little insane. The difference between two and 30 is very minor. The difference between one and two is pretty decent. So I would say Finding the two cards that optimize is really the gold standard.”
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 most optimal would be open up some brokerage account, throw 100 grand in treasuries, and not worry about it. 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, it's like go open the Fidelity card that gets 2% on everything and you don't have to move money anywhere. There are multiple cards that are in 2%. Capital One has a spark cache on the business side and then a venture card, which is just 2x points on everything on the personal side. So there are a lot of options, but for you and anyone 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”
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 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. So at a minimum, it's like. 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, three and a half percent cash back on travel and dining. Stop worrying about these 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
“So, you can do two things. You can book a flight in the Amx portal for anyone. You can transfer those Amex points only to your loyalty account, but you can book it for anyone. So you can transfer those membership rewards to Air Canada and book a flight for anyone in the world. On any flight that Air Canada's 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 Amx 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
“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. 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 want to go in the month after you graduate. 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.”
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
“Is the value of the thing you're giving and all that? Another option, though, for anyone who's a business owner, it's like, oh, I could give all my employees a thousand dollar bonus, or I could send them all on a $5,000 vacation that cost me $1,000 worth of points. That employee is going to have this incredible experience pick any luxury resort that's in the Hilton portfolio, Amex transfers one to two to Hilton. Know 24 million Hilton points. You're like, where do you want to go on vacation”
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
“Don't have an answer to that, but. I would be very surprised if you bought a flight for someone and if you asked your accountant, they might say like, it seems fine. Like I'm not an accountant. I'm not going to tell you what to do. I'm sure someone listening will tell you there are tax implications.”
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 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 want to go? Like we'll find a time where the flights work. I will book you there. You will save $20,000 if you otherwise would have 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 because like 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 amazing trip. And so I would say.”
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've been talking to this woman, unfortunately, for like three or four calls before I knew the price. And she was like, your wedding town's fun. Like, 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 a honeymoon. And she was like, gosh, it would be fun to do your wedding. It'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? Always wanted to go to the Seychelles. The street price of two.”
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 last story was that, and this goes back to my earliest days of buying pizza in college, when we were getting married, we had no idea how expensive things could be at a wedding. And so this guy 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. And I was like, no, like 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.”
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 an extreme version of points arbitrage. A lighter version is just I spend a lot of money on Amazon. I mean, let's not use Amazon because 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 forex points on groceries, you get Forex on Apple instead of one because you bought the Apple gift card at the grocery where you get elevated points. And so looking at places where you can move around your spending or buy things that are easy to sell on a card, great options.”
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 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. And so I think.”
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 it's just a great example of learning to spot places where promos or credit card rewards can be pretty lucrative. And so if anyone was around in the mid-2000s, the U.S. government kind of passed some legislation to get this $1 coin in circulation. And so they basically said, we've got to get this coin in circulation. And so they basically let you buy dollar coins from the US Mint website for $1. And you can put them on a credit card. And so you would go on. And the idea was coins last longer than bills. And so the government said a $1 coin would save us $5 billion over 30 years because it would last, you know, we didn't have to reprint all these bills. And so they sold $1 coins, shipping included for $1. And this one guy, I don't know his name, bought two. Half million dollars of dollar coins.”
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 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.”
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
“Pretty short stories, so 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, it was like you get a thousand 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 barcodes. 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 him in.”
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, the card is marketed as earning 1.5 or 2 points, and then they multiply it. So it's a little, I wouldn't say it's like that complicated, but it's not as straightforward in that they're not marketing as that. But on the website, they say, you know, deposit $100,000 and hold it at a Bank of America account for your business, 2.625%. If you're a business that doesn't want to think about this game, you just want to get the rebate on everything. 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
“The way Bank of America works, they have this program called Preferred Rewards. And depending on how many dollars you have on deposit, they multiply your earnings by up to 1.75.”
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 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. And for that case, Bank of America, similarly, has business cashback cards that if you put $100,000 in a business bank or brokerage account, you get 2.625% back on every business transaction. Like that's the primary business card we use.”
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
“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? Pretty cool. They don't think about the cost of travel. Now, they can only go where Southwest goes if they want to go for free, so trade-offs, but.”
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
“All the points and miles they've earned from Southwest. They used to buy flights for them, and their kids fly free with them everywhere they go.”
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
“25,000 points. If you spend $125,000 on a Southwest card, you will get companion pass. 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. 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 know, you pay the $5 to $50 depending on where you're going. That one's one where 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 paths because 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
“Depending on the airline, it might be. Upgrades as available, right? Like not anytime, you know, free Wi Fi, whatever the perks are. Like Southwest is one of the ones where you actually get the guarantee if you earn $100.”
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
“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 and hyatt their highest global 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. What does that give 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
“And then on the, if someone's in the chase ecosystem, there's a Chase Inc. preferred card, which is 3X on ad spend and travel. I think it's also office supplies and shipping or something like that. I can't remember all of them off the top of my head. So that's one path. 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 until you can redeem them. There's no value. So what some people do, and clearly 1% of GDP on Delta cards is an example. Most of the airline credit cards and”
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 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 in for their family reunion in some city in America. They're not trying to go to the Maldives or Borobora every weekend and they're not ready to book it on a dime. These aspirational stories are just that. They're aspirational. And so if they're not in your short-term future racking up Hilton points doesn't do you a lot.”
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 mean, that was just on hilton.com. Hilton points are notorious for going on sale all the time. I will say you can't buy chase points. You can't buy Amex points. Airlines points go on sale from time to time. So there are places where you could buy points from airlines if you see an amazing deal. 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 award tool. Go to points. Yeah. 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.”
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, someone who'd been playing the cashback game their whole life could just go to the Hilton website, buy 120,000 points for $600, book the $3,000 room for $120,000, and get effectively the same elevated value that I got from playing the points game without ever playing the points game.”
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
“It was $120,000 Hilton points per night. Hilton points when I booked the hotel were on sale for half a cent each. 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. But on the website, the same day you could just buy $120,000 for $600.”
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
“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 want to play the game and try to get the most out of it and take all these aspirational trips? Or do you want to just put cash in the bank and not worry about it? And that doesn't mean you can't get some of the value. If we look back to one example I shared, the Capro Cot Hotel. Beautiful hotel.”
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 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. There's no games to play. It's not, what do I use for this? You'd get 2x on everything. You would have probably been a lot better off 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're getting one and a half on a lot of those things for business. But you could have just gotten two on everything. It probably would have simplified your life. And then you could have picked a card, whether it's personal, I'll focus personal use case, which is like Chase Sapphire Reserve card is 3X on travel and dining. The Amex gold card is 4X on dining and groceries. I don't want to 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”
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
“Specifically booked with the airline. And so not a great card for anything other than flights booked with airlines. But getting five points on flights booked with airlines, excellent. But if you figure 90% of the spend you put on that card was not a flight booked with an airline.”
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 tried to model out what you could have done and what the impact would have been. And my rough answer, and I built this whole, I don't know, this optimizers tool, which was like, you could basically put in how much you spend and you could check off like 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. Like that is the optimal solution. 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.”
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
“Somehow I've been able to just be like, nope, and I just ignore it all. 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 nine to five time, 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, does it cost me $1,000 an hour to play with my kids? Like, I don't, that's just a...”
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 think about this all the 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. On the flip side, I often think about what is my time worth? I get requests for people to, oh, hey, could you consult on this thing? And I'm like, 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 want to, you know, lay in bed and watch this movie? It's $250 to watch a movie”
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
“Yes, yeah. There's like dozens of names 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-cancelable 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. Like, you know, make tons of mistakes doing all this. That's just how we learn. Even once you know the things, you do it wrong. 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?”
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 then they have an opinion. They're like, this is a good deal with points. This is a good deal with cash. So you're like looking on Google Flights to go to San Diego. And it's like, hey, actually, just go transfer, go use United Points. Don't buy this one. This is a bad deal. It's like even easier than these other tools because it lives where you're already searching. Now, sometimes I'm like, let's just book it, be done. I don't want to spend my afternoon on saving $5 or $20 or even $50. I kind of do it $50, but I should 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
“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 going to take this trip. You know, like my wife sometimes asks me, she's like, 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 as like the source of this information? And so for me part of it is sport like we talked about. Part of it is figuring out like at what level do we stop caring? So it's like when I was early to this game, it's like, if I'm going to save $20, I'll stop caring. Maybe now that threshold's at $100. Maybe for some people, it's at $1,000 or, you know, even higher. So I've gotten better at is this a thing I want to optimize or is this a thing where I'm just going to buy the flight? Like I got to go to this conference in San Diego. Flights aren't that expensive. Let's just buy it. For anyone thinking that way, and this is also good for 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
“I'm not going to not buy berries if they're expensive, but I might pick the berry that's the better deal this week. But I'm not going to not do it. And I'm not going to drive to another grocery store to get 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
“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 Barry's example. I think I'm probably more likely to look online, be like, should I order my groceries from Amazon Fresh or Whole Foods and like which one's cheaper than necessarily drive store to store? But I'll credit Ramit Sati for these money rules where it's like, okay, for groceries, we stop caring. Like it doesn't matter. Now, does that mean that when I go to Costco to buy berries and I might see like blueberries are like twice the normal price, maybe we just buy strawberries instead, you know, and we don't like.”
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
“Yeah, so we're going to Costa Rica in June, which is not, you know, the height of rainy season, but it's certainly not like the most perfect time to go to Costa Rica. It's not necessary. I think we're going to hit Japan. Obviously Cherry Blossom season is flexible. But like I think we're going to hit Japan in primetime next year. And so you don't have to wait for shoulder season, but there's just so many better options. 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, seats.errow has a sister site called rooms.ero 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”
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 don't know what Majorca is like in October, but right now you can go for a week or two in October. Obviously, I know summer is probably the prime time. But I think when you start to look at shoulder seasons and last minute stuff, you could just get crazy, crazy deals.”
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 challenge give me a week of your time and I will come back with a Tim is going to this place in this amazing deal and he's going to stay at this incredible property and just unwind for a week and explore whatever part of the world we send him 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