Frequent Miler on the Air - The 2026 Team Challenge: Wild Card! | Coffee Break Ep117 | 8-4-26

Episode Date: August 4, 2026

Every year, the FM team does a team challenge where we compete to see who can make their points & miles go farthest. We're calling this year's challenge "The Wild Card Challenge". In today's episode we'll give you the high-level overview of what it's about! (Don't worry, we'll give you even more granular details soon!)(00:41) - What are the FM team challengesLearn more about past challenges here: https://frequentmiler.com/annual-team-challenges/(01:24) - Why do we do these?(03:39) - Who's participating this year(04:41) - Introducing: The Wild Card Challenge(08:08) - High level about this challenge(10:48) - How do the contestants feel?Get 15% of ESIM from our sponsor SailyThis podcast episode is sponsored by Saily. Saily is an ESIM service app created by the security experts behind NordVPN. Instead of paying absurd daily rates to your home carrier or swapping SIM cards on arrival, Saily gives you flexible prepaid data plans in over 200 destinations worldwide. Download Saily from your app store and use our code FREQUENTMILER at checkout to get 15% off your first purchase. https://saily.com/frequentmilerSubscribe and FollowVisit https://frequentmiler.com/subscribe/ to get updated on in-depth points and miles content like this, and don’t forget to like and follow us on social media.Music Credit – “Ocean Deep” by Annie Yoder

This is a Voyescape podcast. You can find all of our travel podcasts from around the world atvoyescape.com. Today's coffee break, the 2026 team challenge, wild card. Welcome to Frequent Milers Coffee Break, where we focus on a single topic related to miles and points. Each coffee break is limited to 20 minutes or less or your money back. Hi, this is Greg, and on today's coffee break, we're doing something a little bit different. The entire entire Frequent Miler team is joining me today. Hi, this is Tim. And this is Carrie. And this is Stephen.

And this is Nick. And wherever you're watching or listening, you can leave your wallet in your pocket because we know we're going to go over 20 minutes today. There will be no refunds. We'll give you a pre-fund. We'll just make this one free right from the beginning, like it always says. Every year, the Frequent Miler team does a challenge where we compete to see who can make their points and miles go furthest.

It started years ago. 2019 we did a challenge we called 40K to far away, where we challenged each other to see who could go the furthest with just 40,000 points and $400. And we went extremely far. Nick found himself, ended up in the far reaches of Oceania. I went to the furthest steps of Africa and Stephen pittled around Europe for, it seemed like, months as far as I could tell. He made his points and cash goes so far. More recently, we've been doing them every year since then, and the most recent was 100K vacay, where we

challenged to see who could build the best vacation with 100,000 points and $1,000. And now we're back with the newest challenge. So why do we do these things? Well, first of all, it's fun. We really enjoy doing these. And we constantly, hear from listeners and blog readers how much they enjoy our team challenges too. It often pushes us to find incredible deals that weren't previously uncovered or to find more details about those deals. So, for instance, Greg wrote about using just 90,000 membership rewards points to book around the world trip a few years back. And while that sweet spot is gone and so is the one to Hawaii for 7,500 miles each way that I uncovered in the 2019 challenge, those are things that

readers were able to take advantage of and blog or and podcast listeners rather were able to take advantage of so it pushes us to find those kinds of things and when we practice doing the things that we write about it makes us all better at the things that we do we also learn a lot of the gotches the things that go wrong the times when we try something and it doesn't work out like when I tried to transfer points to life miles at the last minute and it got held up and I couldn't book the trip or tim and I got stifled by some switch phantom space during our flying by the seat of our points challenge. And so it gives us some experience with those things that we can warn readers and listeners about. We find tools and get used to

using them that'll give us an edge over everybody else by helping us find available award space or rooms and that sort of thing. And we build up our knowledge so that we can recognize great deals when they happen. One of the best tools you'll develop over time in this hobby is the ability to recognize when a particular deal is really outstanding and you need to drop everything and jump on it. And the best way to get better at that is to continue chasing and finding new deals. So it helps us kind of determine that sort of thing and recognize patterns that hopefully help you, the listener and the blog reader, travel more and travel more comfortably or however it is that you hope to travel.

And so the time has come again for us to talk about the annual challenge for this year. In, well, effectively, we've built up a system where the champion of the last year's challenge is able to sit in judgment on the contestants of this year's challenge. And the judgeer in chief this year will be 100K vacate champion Stephen Pepper. And Stephen Pepper will be joined by Kerry because Kerry is the wisest of all of us. And so between them, they will parse which of Nick. Greg or I is most able to, with style and Savoy Fair, complete the challenges that they have set up for us this year, which we are about to learn. Nick and Greg and I do not know the details of this challenge. We're about ready to find out from Carrie and Stephen. So, Carrie, why don't you tell us about it?

Yes. Okay. So some pieces that you guys already know, you guys are. contestants, not the listeners. We are calling this the Wild Card Challenge because we've created wildcard decks. Our contestants will pick from a deck of cards to select hotel, airline, and transferable point credit cards. They'll be allowed to resource those for their dream trip, and then they'll select travel destinations from another deck of cards. We'll find out if they can build amazing trips from these randomly selected cards for destinations, and then additionally, challenges and perks. So just like a real card game,

they're going to have to pick some cards they don't want. They're going to have to pick some cards that make their life harder and then some cards that make their life easier. So I'll re-sumorize those decks. Again, we've got destination deck.

This tells our contestants the first two destinations they're going to, and then, of course, Stephen and I love doing this. We'll surprise them with a third destination they have to get to at the end.

And then they'll draw from credit card bonus decks to tell them where their hotel, and airline and general points budgets are coming from based on those cards. And then they'll also have obstacle decks, which we're going to need your help with at some point, to create challenges that make their booking just a little bit harder. And we want these challenges to kind of represent challenges you've told us about over the years. Things like maybe you travel with a family, so we might make them book only hotel rooms that allow up to four guests.

or maybe they can't book a flight unless it has two award seats available. Maybe you guys are always traveling with a partner. So we're trying to emulate that with our obstacle decks. Then we also feel bad for our contestants. So we need to give them power up decks too. So these will be things like get out of surcharges free or pick a 30% transfer bonus, things like that to just help them out a little bit. We think our contestants need a little help.

Then for scoring, this is Stephen in my favorite part. We get to judge what they do. During the challenge period, they will have to use their budget based on the cards they've picked to travel to three destinations. The two they've picked from their decks and the one that we assign them. And they must arrive at each destination in time for a pre-scheduled live stream check-in. So they can't just go willy-nilly around Europe for three months like Stephen did. then we'll assign points to each leg of their travel according to we love our acronyms this time it's wild wallet friendliness ingenuity luxury and duplicability so are they acting in a money savvy way

that's not just spending their way to a great trip with cash are they practicing ingenuity in the points tricks that they are hopefully drawing from their years of experience, are they traveling in some kind of luxury? And then duplicability, are they doing things that could be done by somebody else? They're not doing something that's so niche that it's only something that they could do. All right. I think that's as much summary as we'll give for now, and we'll give you more details as time goes on. We'll be right back after this with more about the Wild Card Challenge. And we're back.

Stephen, so far we've heard high level about the challenge. Can you give us more specifics? I want you to drill down to the next level here. Absolutely. So the first step of any of our challenges is to announce the challenge, and that's exactly what this coffee break episode is. We're letting you know about the World Carhart Challenge. So the next step in the next few days,

Carrie's going to be publishing a post where she's going to kind of recap a little bit about what our challenges. and also ask for your help because we want some suggestions for the power up and the obstacle cards. So she'll be giving more details about that and the kind of things that we're going to be looking for. But we would love your input because that's going to help us make the most interesting and potentially frustrating challenge for our contestants. But it should make it a lot of fun. We're then following that up with a live stream on September the 9th.

And so that's when the guys are going to be picking their cards. So they're going to be picking a couple of destination cards initially. They're going to pick the different credit card bonuses. They're going to be picking their obstacle cards. And they're going to be picking their power-up cards. And so at the end of that live stream as well, Carrie and I are going to be revealing their third destination, which, just to wet the appetites of the guys,

we had something in mind for a long time. But we actually changed it recently because we thought that we might come up with a slightly better idea. But they didn't even know what the original destination. was, but we have changed things. So we're really looking forward to what they come up with during this challenge. And then travel will begin a few weeks after that. So towards the end of September, all three of them will be setting off.

And then two days after that, they have to be ready for a live stream in their first destination. So we're going to be catching up with them, finding out how they got to their location, where they're staying, what they've gotten up to. in the meantime doing some travel-related things. And then a couple of days after that, they've got to be in their next destination for another live stream. And then a couple of days after that,

they've got to be at their third destination, once again, telling us all about how they got there. They can let us know about the hotel that they're going to be staying in, which is going to be a common hotel for all three of them, because the third destination is where they're all going to meet up, because the first and second destination, they're going to completely different places. And at that point, along the way,

Carrie and I are going to be judging them based on the wild card criteria. So yeah, that's what we're up to. That sounds great. I think it sounds like so much fun. You know, usually as a contestant, usually once we have the rules of the game nailed down, it's a ton of work because we're spending all our time, looking up award availability, trying to figure out what route we're going to take to do whatever the game entails.

But this time, there's literally nothing we can do, I think, until we actually pick the card so we know where we're going to have to go and what kind of points we have to work with and all of that stuff. So for me personally, as a contestant, this is pretty fun because I don't have to do any work yet. But it seems like a ton of work for the judges. Well, the good thing is we can outsource a lot of it to the readers by having them come up with a lot of the ideas for the obstacles and the power.

True story. Thank you in advance for your assistance. Greg, if you haven't been doing any work, evidently Kerry and Stephen didn't send you the bribes.judges at frequentmiler.com email address yet. So that makes me feel a lot better about my chances. I think that, you know, there's going to be a couple of what I really like about this challenge is I think it gives sort of Nick and Greg and I sort of we can't really do anything about the raw materials that we're starting with. And I think that's kind of fun because we effectively have to take things that we have to take currencies and cards that we're being given.

And then within a fairly short amount of time, we're only going to have a couple of weeks. We're going to find out the cards and then a couple weeks later we're going to be taken off. But we have to be creative with those things, which I think will be a lot of fun, as opposed to sort of sort of being able to strategize about which currencies or which cards we want to start with. And, you know, I do think it's fun. It will be, I'm a little, it's fun and it's also a little nervous. Stephen and Kerry were judges on a previous challenge together. It was flying by the seat of our points. And that ended with Nick almost being exiled in Morocco. So they may, they look for those who are actually looking at them, they look friendly and

unassuming, but really, they're fairly devious. So I'm also, I have a little bit of a hitched breath waiting to see what they're going to come up with in terms of curveballs and obstacles as they put them. Yeah. Yeah. You know, one thing I wanted to add on, Tim, to your earlier comment about how it's like we've got a bunch of, we'll have a bunch of stuff to work with that's not of our choosing, but we have to make it work with that pile of stuff. And it reminds me of the Apollo 13 movie where they have to figure out how to get the spaceship back home safe. And they dump a bunch of stuff on a table and say, all right, this is what they have to work with. You know, make it happen.

Obviously, the stakes are much, much lower here. But it just reminded me of that fun moment in that movie. Yeah, I think it's definitely going to be a challenge that forces us to think outside of the box a little. bit. And, you know, with it being the case that we get our raw materials, so to speak, our cards and our destinations close to travel, by some token, it seems like a bit of a last minute challenge, right, where we don't have a lot of time to prepare and we have to come up with something. But I think actually the way I'm looking at this is a little bit different than that. There was a line recently in a post I read at one mile at a time where Ben was

talking about the current state of miles and points. And the one statement he was, he made that really stood out to me was, if you want to get the best deals, you need to be ready to book travel at any time. And so you need to be ready when the deal is there to drop everything and book it. And I think that this is going to give us the opportunity to showcase the fact that that that is something that always exists. That, you know, you might think that it's only when you see on a blog that there's a glut of award availability. That's the only time you're going to find something. But really, if you're looking in different parts of the world, different destinations, with different currencies, you can almost always find something of interest. And so I look forward to

kind of taking the opportunity to do that, to kind of drop everything and just figure out how we're going to book a trip in a couple of weeks. So I think that'll be an interesting challenge. And I think the fact that we don't know what we're going to get is going to force us into some of those interesting fines because there are, I think, things that we're each particularly strong with, the currencies that we frequently book with or the sweet spots that we frequently use. But I think that there are definitely kind of, I'm not going to call them weaknesses, but maybe blind spots for all of us in programs that we don't frequently use. And we're just as likely to end up with something that we know well as we are to end up with something that we know less well. And either way, I think we're all going to

kind of take the bull by the horn, so to speak, and try to use those things. to the maximum advantage. So I look forward to seeing what we come up with and what we do and what Stephen and Kerry have cooked up because, as they said, we don't know which the first two destinations are going to be. We don't know where we're all going to be meeting up. And so I'm pretty excited to find out how that all shakes out. All right. That should give you guys kind of a high level summary of what we've got going on, but I'm sure we've got a bunch of questions. I can see, I can see Nick with a question. I can see a question just like happening in Greg's brain. So don't worry.

We're going to be writing a post here in a few days, introducing way more details about this. And there you'll have a chance to ask questions at the comments, and we'll try to address a lot of them ahead of time, too. So check that out. Watch the blog at Frequentmyler.com for a lot more details soon. This episode was produced and edited by Carrie Yoder, music by Annie Yoder.

If you've enjoyed what you've heard today and you'd like to get more of this in your email inbox each day or each week, go to frequentmiler.com slash subscribe to join our email list. Follow us on all the various social media. Join our Frequent Myler Insiders Facebook group. And wherever you're watching or listening, don't forget to like this or give it a thumbs up. If you have a question that you'd like to be considered for a future question of the week or a piece of feedback that you'd like to be considered for our giant mailbag, you can send that to send it to mailbag at frequentmiler.com. Hi, I'm Mike Siegel comedian and since 2011,

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