Our biggest point gambles | Frequent Miler on the Air Ep374 | 9-4-26

Frequent Miler on the Air

In this episode of Frequent Miler on the Air, hosts dive into their most audacious point-gambling moments, from historic deals like Nordstrom's 36X bonus in 2012 to

Key takeaways

• Canadian Aeroplan cardholders can earn up to 3.5 Hyatt points per U.S. dollar through high-value spending categories like dining and gas.
• The Air Canada-Aeroplan-Hyatt partnership offers unique value in Canada due to limited hotel transfer options, especially for Marriott-only users.

Main topics

• Air Canada Aeroplan to Hyatt 2:1 transfer value
• Canadian credit card rewards strategies

Notable quotes

"If you could earn 10 to 15 Aeroplan points per dollar through Rakuten, would you transfer them to Hyatt? Probably not—because you already have access."

Conclusion

While not every point gamble pays off, the most successful ones often

Transcript preview

Speaker 1 (0:01) This is a Voyescape podcast. You can find all of our travel podcasts from around the world at voyescape.com. On today's episode, we'll talk about why Air Canada to Hyatt 2-to-1 transfers can't be a good deal. We'll reminisce about how we won big on a 240X deal, and we'll lament the 250X deal that got away, and a lot more. Frequent miler on the air starts now. Speaker 1 (0:32) Today's main event, our biggest point gambles. Every now and then there's a deal that's maybe too good to be true. And you've got to take a chance if you're going to dive into that thing, because sometimes it's not going to work out. We're going to talk through some stories from going way back in time to close to present day about times where we jumped in, took a gamble and won or lost when in the pursuit of miles and other rewards. And remember, if you want to jump ahead to one of those stories, you can just expand the show description to find the timestamps in that box. And wherever you're watching or listening, don't forget to subscribe, enable notifications, give us a like or leave us a review. We always appreciate hearing from you. All right, let's drag out this week's Giant Mailbag. Today's Giant Mail comes from Josh. Josh wrote in about the Hyatt Aeroplan. Speaker 1 (1:25) tie up. You know, a while back, we talked about some news about Hyatt and Air Canada Aeroplan partnering up, and we were kind of meh about the whole thing from a U.S. perspective. But Josh writes in from a Canadian perspective. And Josh writes, on your recent FM podcast, you discussed the Air Canada Aeroplan Hyatt partnership. And overall, you weren't that excited about it. I totally agree with your sentiment when looking at it from a U.S. perspective, which you should be because that is your audience. But as a Canadian, I thought you might find my perspective interesting. I'm not looking for a response or anything, just thought I would share. There are two main areas I find useful. Point transfers. I think if you look at an aeroplane point as equivalent to a transferable point, then it makes sense to think of the transfer as a bad ratio. Speaker 1 (2:23) And as an aside, so the transfer ratio with this tie up is you could convert two aeroplane points to one Hyatt or two Hyatt points to one aeroplane. And Josh says, even comparing to what you can book with aeroplane points, it might not seem that exciting. But one big difference in Canada is that we can earn so many more aeroplane points that the maximizers like me often end up with more than we can use on flights alone. In Canada, we have that Amex. Cobalt card that earns 5x membership rewards points on dining, grocery, and gas. Speaker 1 (2:59) And when you consider that this is on Canadian dollar spend, that's the equivalent of earning seven points per dollar in the U.S., in U.S. dollars. Now, if you look at the Aeroplan to Hyatt two-to-one transfer ratio, it's like earning 3.5 Hyatt points per U.S. dollar in those categories. That sounds pretty good. Another incredible thing is that we have the Aeroplan eStore that earns a minimum of 3x. when you have elite status, on most Amazon purchases. In the U.S., portals have stopped giving rewards on the majority of Amazon spend. For Prime Day and Black Friday, presumably means in Canada, they run 10 to 15x multipliers, meaning with buying groups, I can earn over 200,000 airplane points just from those few days per year. Speaker 1 (3:50) So, I think you made some good points there. And then the second area where Josh talks about it being a great partnership is with regard to lack of other options. In Canada, we have great ways to earn rewards for flights. We can earn Avios, American Airlines, Air France Flying Blue. But Marriott is our only option for hotels. And even at that, the earn rate and transfer rates aren't that exciting. We have no ways to earn or transfer to Hilton. And up until now, we had no Hyatt options either. Hyatt is really pushing their expansion in Canada with the building of new hotels and taking over some others that were previously owned by other chains. I think this is a good way to get access to the Canadian market without a full credit card launch. If the goal of this partnership was to expand the market share of Hyatt in Canada, then I actually think they did pretty well with it. Speaker 1 (4:44) That's so interesting. I'm glad that Josh wrote in with us because it's fascinating. It makes some really interesting points here. I mean, the ability to earn essentially, like you said, three and a half Hyatt points per dollar on grocery, gas and dining per U.S. dollar, that is. And like you said, that's pretty compelling. I mean, if there were a card that you could earn that with here in the U.S., we'd be pretty excited about it. So I can see where you might have that perspective, particularly if you're earning enough arrow plan points. Speaker 1 (5:14) you don't need more aeroplan points, then yeah, I mean, that really was a lot of interesting feedback there. Also, you know, interesting to mention that they didn't have other hotel options in Canada. And one thing that's kind of interesting is that there is or there are possibilities or opportunities for people to get cards in either country. And the complexities of that vary a little bit. But we know we've spoken at a couple of conferences in Canada, and we know that there are a lot of Canadians that have U.S. credit cards. It's not terribly hard for them. So though they may not have access to Hyatt, they might have access to some Hyatt cards if they're able to get into the U.S. credit card market. Nonetheless, for a lot of people, this does seem really kind of interesting, not for U.S.-based customers probably, but I can certainly see where this would make sense for Canadians. Speaker 1 (6:08) Yeah, yeah. Really, it was eye-opening to me to see how many great options they have for earning aeroplane points. I mean, obviously, I knew they could, but I had no idea how big the point earnings could be. So, yeah, I found it fascinating. And to his point that our audience is U.S., I mean, that's not really intentional so much as that we do cover... U.S. credit cards. So, you know, when we're covering things like Hyatt or Marriott, sort of in general, I don't think of us as like, you know, focusing on a U.S. audience necessarily. But it is true that we talk about U.S.-based credit cards. That's what we know. So that's what we discuss. That's also where most of the big opportunities are at. But as Josh showed, there's some big opportunities that we're not focused on. Speaker 1 (7:05) Let me follow up with a question here, though. So, all right, Josh mentions Amazon and Black Friday and 10 to 15 X multipliers. But let's take that idea and transfer it over to our U.S. based audience now. So if you could earn 10 to 15 arrow plan points per dollar, which. You very frequently can when you're clicking through Rakuten. If you're earning transferable points, they could transfer to Aeroplan. I mean, would you consider then transferring those to Hyatt? Probably not because you have other access to Hyatt, right? Right. I mean, yeah, if you want Hyatt points. You know, especially if you have built lead status, you're you'd be earning through Rakuten, getting the points over to built and then transferring to Hyatt as needed. So, yeah, wouldn't make any sense for us to convert Aeroplan. Yeah. All right. We'll be back right after this with our main event. Speaker 1 (8:02) We hope you're enjoying the Frequent Miler on the Air podcast. Did you know that Frequent Miler is also a website? At frequentmiler.com, you'll find all the latest deals, news about points, miles, and rewarding credit cards, the single best, best credit cards page on the web, guides to all popular rewards programs, and many other terrific resources. If you'd like to get our posts sent to your email, go to frequentmiler.com forward slash subscribe and sign up for free. And we're back with today's main event, our biggest point gambles. Today, we're going to be reminiscing, basically, about times when we've taken big risks in order to earn big rewards. Let's start by going all the way back to 2012 when, all right, so this is a story. I think this is just a me story, not a next story. Yes, no, this is definitely before I was. Speaker 1 (8:58) In the game. I don't even think I had – I knew that this world existed in 2012. So this one was all you. All right. All right. So 2012, I had started the blog in 2011. So it's fairly new to me. But one of the things that happened was British Airways Shopping Portal was running a promotion where they were offering a multiplier on rewards. And Nordstrom – was offering a promo through the British Airways shopping portal at the same time. And those things combined to mean that you could get 36 points per dollar shopping at Nordstrom. And that was unheard of huge at that time. So I, you know, look through Nordstrom's online shopping to see, you know. Speaker 1 (9:50) What could I possibly want to buy a lot of from Nordstrom? And particularly, I want to see, was there anything I could maybe resell so that I can basically buy points at a very cheap rate by buying stuff from Nordstrom and reselling it at somewhere close to the value I bought it at? And I found that they had GPS watches available. Each watch was about $400. I bought 10 of them. So I spent $4,000 with this gamble. And based on earning 36 points per dollar, that would be 144,000 British Airways points is what I could earn. Now, there were two parts of this gamble. There was, would the shopping portal track correctly? Would both of those promos I mentioned that were happening at once? Speaker 1 (10:45) Would they actually stack the way they were supposed to? And, you know, would it all pay out correct? Right. That's one one gamble. The other one was, could I resell these at anywhere close to the amount I bought them at? So my idea was that if I sold on Amazon, so I was going to use fulfillment by Amazon, send the watches in there. and sell them. And I would lose some money with each one because Amazon keeps a little bit. And I made some assumptions about how much less I'd have to charge than Nordstrom in order to sell them. And so I had figured out that I would be basically buying points for half a cent per point, which is a great deal if you could buy points that cheaply. But there were all kinds of risks involved in doing that. Speaker 1 (11:40) So I mentioned earlier I had bought 10 of these $400 watches. I sent all 10 to fulfillment by Amazon. They actually sold very quickly and very close to retail values. So the loss would have been less than I had estimated. So it would have cost me considerably less than half a cent per point. But it actually got better than that. Of those 10 watches I sent in, Amazon somehow sold 24 of them. And they paid me for all 24 of them. Yeah. So before like all 24 were sold, I actually submitted a case to Amazon because I felt bad about this. Like, you know, I don't know what was happening. I submitted a support incident to them. Speaker 1 (12:31) and they wrote back saying, Greetings. Having researched your account, I could see that you have sent 10 units, but total order shipped for this is 17 at that time. And I could see that all the items are shipped and the payment is already posted to your account. As all the orders have been fulfilled and there's no fulfillable quantity in your account, we would not be able to further investigate on this issue. You would... you will be receiving the payment for all 17 orders. Thank you for selling on Amazon. What does that make? They were basically saying, I'm out of luck. There's no way to not get paid for those extra. Nothing they can do to help you. Right. Nothing they can do to help me. You have to accept the money we're sending you. And as I said, they ended up selling 24 of them. Bizarrely, about a year later, they sold some more. Wow. Speaker 1 (13:27) Yeah. Wow. So I made out like a bandit on this thing. I, you know, I earned thousands of dollars. That time I submitted a sport incident again and they actually did stop it from happening, but they never clawed back any of the money they had sent me. Really, really crazy, crazy stuff. That's wild. That's wild. I gambled and won really big there. Yeah, you did. My goodness, that worked out really. I think maybe we glossed over the fact that you earned 144,000 British Airways points in the process. So not only did you make a lot of money, you also made a whole bunch of miles up here. That actually reminds me of what I was doing for a long time with Neiman Marcus because for a while, I don't know, I was buying and reselling stuff. And Neiman Marcus used to run these promotions where if you spent $2,000, you would get a $600 Neiman Marcus gift card. Speaker 1 (14:17) In addition to the 2000 bucks. So I found a pair of headphones that they sold for exactly $400. No, no pennies. It was just $400 a pop. So I could buy five of those and it would be exactly $2,000. And I found that I could resell those on Amazon for a net $372 each is what I ended up with because I was able to sell them for the same 400. So, so I was losing, let's call it $25 per. per headset for the sake of simple math here. Let's call it 30 because there's probably tax that I pay, I assume. So 30 it pops. So about 150 I would lose on the first $2,000, but then I'd get a $600 gift card and buy another $400 set that I'd sell for the $372. So I was making money, but then at the time, back then, there used to be what Greg turned me on to as the double dip, which I didn't even realize when I first started reselling products. At the time, and this... Speaker 1 (15:12) occasionally it could still work. It's not common, but I always try in case when I'm in this situation. Back in the day, you