YouSaid · the spoken record

Chris Hutchins

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169
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2025-06-10
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2025-06-10
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1
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  1. “So there's a really great video if you want to go deep on this. I'll give you the kind of high level on both loyalty programs to airlines, which is kind of frequent flyer miles. And it's the craziest thing I think I've ever come across when understanding business.”

    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

  2. “So I like that from more of an inspire me. It's like, I don't know where I want to go. I don't know when I want to 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. 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, etc. portal.”

    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

  3. “And you go to the daydream explorer feature, and they just give you a map of the world, and you say, you know, hey, I want to go to a beach in first class from the United States. Take me there. And it'll be like, oh, well, did you know that if you want to 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. You want to go to Lisbon in business class for what Amazon equivalent would have been like $275. Anyone listening probably knows you're not finding $275 business class tickets to Europe in the summer.”

    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

  4. “So you could say, Hey, I'm going from San Francisco to Japan, or you could even say San Francisco to Asia, and I want to 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 want to fly in business class. Or I only have points with Amex, so don't show me other options. 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 if you redeem them for Amazon gift cards, might get you, I don't know, I think it's 0.6 cents. So $222. It is rare that you will find a flight to Japan, even in economy for $220.”

    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

  5. “Me and give me the best deal. And one is help me find the best way to get from A to B. So award tool, which is the one you talked about, I think is better for the person who's like, I want to go to Japan. I have a few days of availability that I could explore. You know, I could go a couple days earlier, a couple days late. But ultimately, I want to go to Japan.”

    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

  6. “Yeah, so 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, right? Like 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 like depend 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 kind of Jedi mind tricks, if you will. And then a couple companies came out and said, hey, we're just going to 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 three that I like and how they're slightly different. There's really two things you might want in this world if you're trying to use your points. One is inspire.”

    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

  7. “Taped in a certain way. There's some strict requirements because they don't use FedEx for insurance. Obviously, like FedEx would charge an insane amount of money. So they use like a third party. Insurance”

    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

  8. “So I put in my pocket. I usually try to do this earlier so I'm not just like someone's watching me pick up the gold, walk out the door and all that, but I haven't had any issues. And then I go home and I follow their shipping guidelines to drop it off at FedEx. And so it's kind of funny sometimes to go to FedEx and drop a box off knowing there's like $50,000 of gold in the box, but it's insured, so I'm kind of okay with 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

  9. “So, what I mean is, I've gone in and I've locked in the price. So I did a whole episode, by the way. If someone's like wants to go really deep, the guy who runs the marketplace pure, collectpure.com, it's a gold marketplace for all kinds of stuff. I did an episode interviewing him just about gold and how that works. So I go in. It's a buying, selling marketplace. There's bids and asks and I say, I'm going to go take one of these things. And I've locked in the price. So I don't mean I've shipped it off, right? I go to the counter. I give them my receipt. I put it in my pocket. For people who aren't familiar, an ounce of gold is like. Or four credit cards, and that's in the packaging. It's even smaller if it wasn't wrapped. It's like six SD cards if it's like unwrapped.”

    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

  10. “There'll just be people Yeah, you get five, but I wish I had them here. I have a rack that holds them. But as an example, this is a rack from Pamp, which is his Swiss company that just holds bars. So this rack probably holds 20 bars of gold.”

    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

  11. “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 can make a profit selling it for getting even points. I could just make a profit selling this gold. Okay, bring up the Costco groceries totals $180. Could you please add five, which is the limit, five, three, five hundred dollar bars? And they're like, really? Okay, you're total now instead of $180 is like $15,180. And then assuming you have a card with the right limit and your bank's not going to decline a $15,000 transaction, tap to pay. Thank you, Apple, for the simplicity. And then I literally sell it before I've left the store. Like I'm not trying to invest in gold.”

    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

  12. “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. And so there are times where when you're at Costco, if you look up online, like would buying this gold bar and selling it, what would be 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. And you can buy things at Costco with cash. You can buy things at Costco with a debit card. And you could buy things at Costco with a credit card. So 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 on the spread because sometimes that spread might be half a percent.”

    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

  13. “So Costco sells a tremendous amount of gold. I can't remember the stats, but it's got to be on the order of hundreds of millions of dollars, I guess, of gold. And it's kind of funny because sometimes you'll check out at Costco and it'll be like, do you want this gold bar? It's $3,300. And it's like, you know, 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% cash back on everything you spend at Costco, up to $62,500 a year, which for a normal person is like plenty of cash back.”

    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

  14. “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 have on your card. 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 $7 $200 gift cards to dick 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 on the dollar. 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?”

    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

  15. “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. I was stoked because 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, two 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 like a total win-win because there was this rare moment where gift cards were selling at ridiculous prices.”

    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

  16. “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. Now, who doesn't want 10% off Amazon? You know, 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

  17. “There was an app called Pepper. 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, four $500, and then we're going to 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 want to take on the risk of like if this company goes under, they owe me 20, 30, 40, 50,000 dollars 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 break even, right? 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. And I was like, I can do much better trying to arbitrage that than take on a lot of risk.”

    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

  18. “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 like MO for life is I don't want to sacrifice, but I also don't want to go into debt or just spend money I don't have. 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, a huge discount.”

    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. “I think that 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. And I kind of 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. They weren't like, here's my credit card like many people I knew did. And so I was always like, how do I kind of keep up with the Joneses per se? But I didn't have a credit card to take debt out on. Like there were no other options. So, 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. Like it was kind of 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