Points & Miles in 2026: What's New, What's Dying & What's Next with Brian M

Summary

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All the Hacks: Money, Points & Life

"Points & Miles in 2026: What's New, What's Dying & What's Next" with Brian M

Host: Chris Hutchins
Guest: Brian M
Date: January 21, 2026

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Overview

In this first conversational-style episode of the year, Chris Hutchins sits down with points and travel enthusiast Brian M to discuss major changes and trends in the points and miles world heading into 2026. They break down Bilt's major credit card shakeup, the sudden demise of the Mesa card, practical tips for maximizing points, and ways to plan more flexible, rewarding travel. The episode also includes predictions for the coming year, systematized trip-planning advice, and rapid-fire Q&A.

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Key Discussion Points & Insights

1. Major Changes in the Points and Miles Landscape (00:00–14:59, 19:58–46:48)

Bilt Card Revamp

• Background: Bilt, previously known for letting users pay rent and earn points with a unique multiplier structure, completely overhauled its credit cards, moving away from Wells Fargo to Cardless as the issuing partner ([01:27]).
• New Offerings:
  • Three new cards:
    • No annual fee card: 1x on everything
    • $95 annual fee ("Obsidian"): 3x on dining or groceries (must choose one, groceries capped at $25k/year), 2x travel, 1x everything else
    • Palladium ($500 annual fee): 2x on all "everyday spend" (not all categories), $200 yearly Bilt cash bonus ([02:35]-[08:10]).
• Built Cash Concept:
  • To earn points on rent and mortgage payments, users must earn and use 'Bilt Cash' – spending $30 Bilt Cash unlocks 1,000 points ([08:10]).
  • This replaces the old "5 transactions" rule and essentially functions as a 3% cost to earning rent/mortgage points (offset through other earnings).
• Transfer Partners & Bonuses:
  • Bilt stands out for unique and frequent transfer bonuses (to Alaska, Hyatt, Japan Airlines, etc.) ([02:35]).
• Complexity & Value Calculation:
  • Increased complexity in the new system; cardholders must weigh opportunity costs, category caps, and actual values for multipliers and benefits ([09:30]-[11:22]).
• Sign-up Bonus Uncertainty:
  • Early questions about whether existing cardholders will get new sign-up bonuses; later clarified that they will ([76:16]).
• Sustainability:
  • Both agree Bilt’s changes make the program sustainable, avoiding the fate of unsustainable startups like Mesa ([12:26]).

“They’re adding complexity and complications with this Build Cash concept... Probably mostly just because of the ratios they chose to use.” – Brian ([01:59])

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Mesa Card Shutdown

• Overview: Mesa, a startup card promising lucrative rewards (including 3x across rare categories and mortgage rewards, no annual fee), abruptly shut down its credit card product with zero notice ([20:07]).
• Risks of Startups:
  • Mesa's quick demise illustrates the risks of engaging with points startups, especially when they run unsustainable models ([20:52]).
• What Happened to Points:
  • Cardholders panicked but Mesa eventually honored points as statement credits (not transferable, but better than nothing) ([21:54]).
• Future Trends:
  • The ease of spinning up points programs using third-party providers like Ascenda means more such startups—and more risk—are likely ahead ([22:44]).
  • New brokerage Silo and others now offering transferable points (raises questions about value, sustainability, and risk) ([23:47]).

“Mesa may just be the first of a similar line of opportunities and learning lessons as we go...” – Brian ([25:51])

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2. Predictions & Trends for 2026 (29:48–46:48)

• More Flexible Points Startups:
  • Ascenda and others are enabling more small financial companies and startups to offer transferable points ([30:06]).
• Debit Card Innovations:
  • Co-branded debit cards (e.g., Wyndham, Southwest, United) are picking up steam ([30:06]).
• Elite Benefits Shifting:
  • Airlines/hotels are moving away from traditional travel benefits to more broad-ranging perks (e.g., milestone choices, ability to use points beyond upgrades) ([30:38]).
• Southwest Airlines:
  • Major changes: assigned seating, bags policy, expanded ‘premium economy’ demand ([31:47]).
  • Companion Pass’s long-term future is questionable—likely to become harder to earn before being eliminated ([32:28]-[35:22]).
• Potential Legislation:
  • Proposed (but unlikely) U.S. cap on credit card interest rates could impact availability of points but likely not devalue existing points ([35:22]-[36:07]).
• Coupons & Credits:
  • Growing trend for valuable cards to include more ‘coupon’ benefits—making it hard to use all credits, which may decrease their felt value ([40:35]-[41:35]).
• Personal Deduction:
  • Points/credit management tools are getting more powerful and AI-enabled ([36:07]); Chris is building a custom tool for evaluating card value.

“The most exciting opportunities for people like us are the ones that get outsized value. So we have a selection bias... If someone launches a 1x everything card with transferable points... I should feel good parking a balance there. But I’m like, why don’t I use that card?” – Chris ([26:08])

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3. Keeping, Downgrading, or Canceling Credit Cards (43:22–51:28)

• Annual Fee Analysis:
  • Only keep cards if the real-world value from their benefits exceeds the annual fee (adjusting for “breakage” and how much you would pay out-of-pocket) ([43:22]).
• Old Accounts Matter:
  • Importance of credit age; consider downgrading to keep long-term accounts open ([47:57]).
• Impact of Canceling:
  • Consider effect on transferable points currencies, whether points are tied to the card, and if downgrades are possible ([47:57]-[50:35]).
• Retention Offers:
  • Retention bonuses/offers from issuers now less common and less lucrative than in past years ([47:56]-[51:28]).

“If a friend came to me and said, ‘hey, could you book a hotel room with your Amex FHR credit and get me $300 off a night and I’ll give you $50?’ I’d probably say yes. So, like, that credit is not worth $300 to me.” – Chris ([41:35])

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4. Planning Your Points-Optimized Trip (51:28–72:28)

Trip Planning Strategy

• Systematic Approach:
  • Define travel party (who/why/when/where/how); consider requirements (e.g., specific hotels, number of beds/rooms, air conditioning, elite status, etc.) ([52:13]).
  • Focus on booking flexibility (award bookings now far more flexible than pre-pandemic) ([52:13]).
  • Book at the ‘leading edge’ (11–13 months out) for the best award availability—especially for large families ([57:59]).
• Handling Too Much Flexibility:
  • Use constraints (dates, destinations, anchor hotels or specific flights) to narrow options ([56:47]-[58:48]).
• Elite Status and Award Strategies:
  • Weigh importance of booking direct with preferred airlines versus partners ([61:01]); sometimes status won’t matter if booking premium cabins anyway.
  • Leverage elite status quirks (partner award calendars, cardholder discounts, etc.), which sometimes require manual searches ([63:23], [63:59]).
• Tools They Use:
  • Points Path for domestic; Seats Aero and manual searches for international ([63:23]).
  • Use (and set) alerts for fare drops, better availability, etc. ([72:28]).

Hotels & Accommodations

• Connecting Rooms & Family Plans:
  • Hyatt’s Family Plan (second room up to half off, often can guarantee connecting rooms through phone booking—may vary by hotel/brand) ([67:02]-[68:20]).
• Suites and Timeshare Options:
  • Use certificates and programs that allow booking suites or large timeshare units—especially valuable for families and groups ([69:24]-[70:20]).
• Monitor and Rebook:
  • Bookings should be seen as dynamic; monitor for improvements or changing trip requirements ([70:20]).

“The flights may have been booked long before the hotel or the hotel long before the flights. And as time goes on, I’m consistently monitoring the reservations and looking at alternatives...” – Brian ([70:20])

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5. Listener Q&A and Tactical Moves (73:41–80:13)

• Business vs. Personal Card Spending:
  • No major risk or known penalties for using business cards for personal expenses (or vice versa)—actual practices are “commonplace,” but check card issuers’ rules especially regarding rewards on "business" spend with personal cards ([75:33]-[76:16]).
• Approval Fatigue:
  • If card approvals dry up, look at alternate issuers, consider reducing extended credit, and know some banks require pre-emptive limit reductions ([77:29]-[79:39]).
• Mitigating Approval Issues:
  • Transfer/reallocate credit limits between cards; some issuers require you do so in advance ([78:53]).
• General Recommendation:
  • Always check and understand individual bank rules for approvals, credit handling, and rewards eligibility.

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Notable Quotes & Memorable Moments

• On Bilt’s Overhaul:

  “The biggest confusing thing... is that these cards now earn points and built cash and that Built Cash can be used in ways that has not been clearly defined yet.” – Chris ([08:10])

• On Startup Risk:

  “Mesa may just be the first of a similar line of opportunities and learning lessons as we go will be really useful.” – Brian ([25:51])

• On Coupons & Credits Trend:

  “The value of the credits is going down the more I have. I let many hotel credits just go unused.” – Chris ([41:30])

• On Travel Planning:

  “If the destination is the thing, you’re going to find flights around that. But maybe you found a unicorn saver availability... and you have to book the rest of the trip around that.” – Brian ([55:31])

• On Persistently Monitoring Bookings:

  “Once everything’s booked, I’m not done. This is just the beginning of the process... I’m consistently monitoring the reservations and looking at alternatives.” – Brian ([70:20])

• On Family Travel & Flexibility:

  “Book the best you can and then wait to hopefully find something better. We’re always going to book something we would take.” – Chris ([72:28])

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Timestamps for Important Segments

• Bilt Overhaul Deep Dive: [01:27]–[14:59], [19:58]–[28:54]
• Mesa Card Demise & Risk of Startups: [19:58]–[27:17]
• Predictions for 2026: [29:48]–[36:07]
• Evaluating Annual Fees, Credits, and Retention Tactics: [43:22]–[51:28]
• Travel Planning: Optimizing Points, Family Travel, Booking Strategy: [51:28]–[72:28]
• Listener Q&A Rapid Fire: [73:41]–[80:13]

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Tone & Language

The conversation is friendly, candid, and practical, with the hosts sharing personal experiences, opinions, and humor along with actionable advice. Chris is methodical yet enthusiastic, Brian brings a nerdy, systematized perspective, and together they create an engaging, info-rich deep dive through the latest developments and best practices in the points and miles space.

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Transcript

[A]

There's been some changes in the Points and Miles space and surely more ahead in 2026. So today I'm sitting down with my friend Brian M for a conversation about credit cards, points and travel. We'll get into the recent Bilt and Mesa changes and shakeups, how to plan more flexible trips, ways to decide whether to keep or cancel your cards, and how we're thinking about points, programs and tools in the year ahead. I'm Chris Hutchins. If you enjoyed this episode, please leave a comment or share it with a friend. If like you, and if you want to keep upgrading your money points in life, click follow or subscribe.

[B]

Brian, I'm excited to do this. Thanks for being here.

[C]

Yeah, thanks for having me, Chris. Me too. I'm excited.

[B]

Yeah. So I'm kicking 2026 off with this new concept of a bit more conversational focused episodes with people I know or I've gotten to know about various topics. So this is kind of the first experiment in conversational style conversation about points, travel, miles, what's going on in credit cards. And so I thought we'd start hit on a couple things that happened recently in the news. One as recently as a few minutes ago, which is no coincidence. And then jump into some of how you think about planning trips because I feel like I've learned a lot from you. And then we might take some listener questions on credit cards that I thought you'd be good to help with. And if anyone listening, if you're not interested in the build card and the launch, even though you know it might be relevant to lots of people, feel free to skip ahead in the show notes because we're going to cover a lot of other stuff in this episode.

[C]

That sounds great. Yeah, let's get to it.

[B]

So the first news that I think is topical and the reason we scheduled this episode right now is that Bilt kind of revamped the entirety of their card lineup. How it works, how you earn points on rent, and as of I guess 40 minutes ago, they announced the news. The site didn't actually work at that time, but there was a post from the Bilt team on Reddit. So we have all the final details. I think you and I both have a Bilt card. I am curious how you receive this news, how you're thinking about it as a cardholder, what your reaction was high level.

[C]

They're adding complexity and complications with this Build Cash concept. I understand why they're doing it and I think it will probably be fine in the long term. They're attempting to offset the transaction costs for paying rent and mortgage in a way that makes sense to drive spending to the cards. Because no more. As the joke is right, buy five bananas over five transactions to get your ability to pay your rent using the card for free. So I get it, it makes sense. But it is. It's more complicated, probably mostly just because of the ratios they chose to use.

[B]

Yeah. So for people who aren't familiar, I should clarify two things. One, built a sponsor of the podcast, but they're not going to influence what I say today. I'm just going to be honest and you should as well. And I don't believe they're going to be a sponsor of this episode. So you won't hear a Bilt ad in this episode. I've had my bill card for a while. I enjoy the bill card. I really like the rewards points. Right. I think the reason why you and I probably enjoyed Bilt so far is that they have some great transfer partners. Right. Transfer partners you can't get elsewhere. Alaska, Hyatt, Japan Airlines. And then they regularly do these huge transfer bonuses for people with Bilt status and sometimes even people without it where you might have thought, oh, well, I was just earning 5,000 points, but now they can be 10,000 points. And sometimes it was more than that. And so that's the thing to love. The history, as I understand it, is that the previous build card is issued by Wells Fargo. Wells Fargo was losing a lot of money, effectively kind of subsidizing the cost of rent payments, earning points for free. And that's just not sustainable. And so Bilt kind of said, we're moving off of Wells Fargo, we're moving to Cardless. I'm actually in either one or two weeks, going to just do a full deep dive episode on Cardless and built and the rewards program. So we don't have to go into that in as much detail. I'll walk through all the cards and the kind of nuance of how they earn. But today I just wanted to high level talk about one, how you're thinking about the transition. Right. We have to pick a new card. We have to decide whether we want to let our old card stay open, that moves back to Wells Fargo and kind of high level what the new cards are. So they're now launching three cards. I'll run through the highest level, which is a no annual fee card that just earns 1x on everything. A $95 annual fee card that earns 3x on dining or groceries, 2x on travel, 1x on everything, which is very similar to the existing earnings structure. And then this palladium card that's going to earn 2x on everything, or at least I'll say 2x on everyday spend, which, similar to Robin Hood and US bank, may exclude lots of categories. It might exclude tax payments, it might exclude business transactions. We don't really know the answer to that question yet.

[C]

Yeah, the 25k of cap on the $95 fee for the 3x category seems surprising to me.

[B]

Is it on groceries only or groceries and dining?

[C]

Well, you have to choose one or the other.

[B]

For some reason. I was thinking the cap only applied to groceries, but maybe not.

[C]

Oh, you're right. I think you're right. Yeah. If you choose dining, it's on cap. Groceries is 25k a year. That's right. But regardless, the $95 City Strata Premier, both of those uncapped 3x.

[B]

Yeah, you have both the categories and uncapped on both of them. Yeah, for sure. And I'm just looking at the BILT website. Just refresh. You can get the full terms of all of these things. You know, I'm not going to interrupt the entire episode to go read through 16 pages of terms, but I think there's a lot of things that over the course of the next, I don't know, week or two, we'll probably understand in more detail. And at that point, for sure, I'll want to make sure I cover them in that next episode. So I'm not going to hit on all the details. I know the build team's doing an AMA this afternoon. One question I have is how are you thinking about this requirement of, okay, well, now you get to choose. Do you go to Wells Fargo with your existing card and get a built card? Do you not get a built card and then apply for it fresh so you can get the signup bonus?

[C]

I think that's a tough decision and probably varies person to person on their estimated likelihood of being approved by Cardless, which hasn't had the easiest approvals for some folks in the past. Maybe that'll be different this time around. I don't know. I'm going to take the path of least resistance, most likely, and have my card convert. But I could see it makes sense for others to not follow that path.

[B]

If you have the card, it's going to roll back into a Wells Fargo card and then you're going to get a new BILT card. I don't see a lot of downside to letting it roll to a Wells Fargo card other than precluding getting what I think is like a 20 or 30,000 point signup bonus on the Wells Fargo card it rolls into. Are you just going to let that roll in?

[C]

Yeah, I agree with that. That's the path I intend to follow.

[B]

As for which card to choose, when I'm looking at the lineup of these bill cards, it feels like I might go all the way for the palladium card because 2x on everyday spend seems like the thing that might be the most possible to spend on. Especially when I know built status is something that requires spending on. And that status has often for me been the reason I got these outsized transfer bonuses. Have you thought much about which of the Built cards would make the most sense?

[C]

I have and I think the Built Travel Portal bonus coupons are frustrating. Chris, do you spend a lot of time in $25 a night hotels?

[B]

I do not spend a lot of time.

[C]

So the middle card, the Obsidian, right. It's $50 semi annually with a two night minimum. So that's $25 a night off and that just doesn't move the needle much for me. And the fact that I think the City Strata Premier offers a better overall value. Assuming your one is going to want a Built card, I'm probably looking at either the Blue or the Palladium. And just like you were Talking about the 2x on everyday spend seems enticing. The extra other benefits may or may not be that relevant to me, except for if I'm going to get that Built card because I want to have built cash, the $200 a year annually that comes with the Palladium card is actually a meaningful benefit.

[B]

Yeah, the biggest confusing thing I think my two outstanding questions, which I couldn't get answered before this episode, is that these cards now earn points and built gash and that Built Cash can be used in ways that has not been clearly defined yet. They've said this morning that Built Cash can be used for monthly credits at restaurants, hotels, rideshare and more. What that doesn't mean is if you have $300 of built cash, that doesn't mean you could just book a $300 hotel room and make it free. Does that $300 built cash, can it be used for a $50 off coupon if you spend a thousand or more dollars a night? Or can it truly be used like cash? I don't know the answer. I don't think we do know the answer yet. What we do know is that you will need Built Cash to earn points on rent and mortgage. They're not going to charge a fee to pay for your rent on the bill card. They're not going to charge a fee to pay for your mortgage on the bill card. But in order to earn points, you need to have built cash. At the rate of $30 of built cash earns you a thousand points. Like you started this off, it just seems like everything's a little more complicated than it was before. And so effectively, there's kind of a 3% fee that can be offset by some additional earnings you get with the cards, but there's not actually a fee. But it's definitely a little confusing to me.

[C]

Agreed.

[B]

And I think at this point it's unclear whether as a current cardholder, are they going to give me the same welcome bonus a new cardholder would get? I don't know.

[C]

Yeah. I think that's an important open question in deciding whether one transitions or tries to cancel and reapply in the future. Are you leaning towards one or the other of which looks most interesting? Is it the 2X?

[B]

The thing that I like about BILT is that the transfer partners are great and the transfer bonuses are great. And so in order to keep those up, you need BILT status. And if I think about this from an opportunity cost standpoint, in order to earn status, I'm going to have to spend money on the card and earn points. And if I get a 1x card, there's a huge opportunity cost. There is for sure not a category where I can't do better than 1x with my existing cards. So the problem with the blue card is it will be almost impossible to earn status on built with the blue card without giving up opportunity cost on the Obsidian. Like you said, it's pretty similar to a lot of other cards. So it will be at best kind of break even maybe. And then the Palladium the same. Right. Like I have 3x dining, grocery, or travel cards, but I actually have 4x dining and 4x grocery cards and I have 3x travel cards. So again, I'm. I'm like, there's an opportunity cost to using the Obsidian card. I don't have a card that earns points at a rate higher than 2x on everything.

[A]

Right.

[B]

You could argue there's cash back cards that are better, but I don't have that. And so I think the Palladium card seems like the card that will have the least opportunity cost. And as I understand a handful of factors, like how much is this built credit cash going to be worth, how difficult will be to use these hotel credits Will I get the signup bonus? Can I downgrade the card in the future? I think like those open questions will kind of decide whether I'm not interested in paying $500 a year because then there's a real opportunity cost of $500 I like.

[C]

Right.

[B]

So I think that all kind of plays out and when I cover the episode in a couple of weeks, hopefully or maybe next week, I can kind of walk through some more refined thinking. But off the cuff, my reaction is it's a little more complicated, but I understand why they're doing it because it's just not economical for them to give you up to a hundred thousand points a year for free if you make five transactions. And I want to transition and let you say anything else you want on Bilt to what recently happened with the MESA card, which shows what happens potentially we don't have the story, but when a startup launches a product that is not sustainable and I would rather built given the rewards program they have that I enjoy the ability to use points in different ways, even book flights in the travel portal now that show up as kind of true bookings from the airline, like those things I all love. I don't want that to go away. And so if they need to transition to a less lucrative card so so that the program is sustainable, I'm okay with that.

[A]

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[B]

This in from a few hours after I finished talking to Brian because something just clicked in my head about the new built cards that I thought was worth explaining and that is how this kind of earning your points on your mortgage structure works and why I actually think it's better than I had originally thought. So yes, if you look at the.

[A]

Old built card, you used to earn up to 100,000 points a year on.

[B]

Your rent payments, but you needed to make five transactions a month so it could be five small transactions. So yes, that was awesome. And if you operate in the world where how do you make that continue to be true? That's tough. Now if you flip that and say let's evaluate these cards as cards and see how the return is and I'll pick. You know, it doesn't matter which card actually for this argument or this example, because they're all going to be about the same because of the way this program works.

[A]

So how it works is on any.

[B]

Of these cards you get 4% back on your spending in the form of built cash. And that built cash can unlock Points on all your rent and mortgage payments at a rate of $30 of built cash earns 1,000 points. So, for a simple example, let's say you spend $10,000 on mortgage and rent a year. Okay? So in order to get your 10,000 points, to get 1x points on that spend, you would need to unlock $300 of built cash. Well, how do you earn $300 of built cash? Well, you would have to spend $7,500 because you earn 4%. So in order to get the full 10,000 points on your mortgage and rent. And I'm guessing most people's mortgage and rent aren't $10,000 a year. Wouldn't that be nice? Definitely not in the Bay Area. So, in order to get 1x points on your $10,000 of rent, you need to spend $7,500 a year on the card. But let's inverse this and focus just on the card. And let's look at any of the cards, because the way it works is that $7,500 unlocks 10,000 points, which means you're getting 1.3x points or 1.33 additional points in the value you get from being able to earn points on your mortgage and rent. So if you look at the blue card, you earn 1x points on your spend. So if you spend $7,500, you get 7,500 points, but you would also earn enough built cash to earn up to another 10,000 points on your rent or mortgage. So now you've spent $7,500, but you've actually got 1750 points. So the built blue card is actually going to get you 2.33x points, even though it's marketed as 1x points up to the amount of your mortgage. So if you have a really low mortgage, you're going to get like 2.33x points on that blue card, but only up to the amount of your mortgage. Once that, built cash no longer offsets those fees and only earns you, you know, whatever those rewards are. I have no idea how to value that. I haven't found a description there, but if you jump all the way to the Palladium card, you're looking at a card that earns 2x points plus 4% built cash. And if that 4% built cash unlocks 1.33x points up to the size of your rent and mortgage payments, and if you have multiple properties, it sounds like you can do multiple payments, then you're effectively at a 3.33x card up to that amount. So if you have $100,000 worth of mortgage and rent to use the a large example from the previous card, you're going to need $3,000 of built cash to be able to earn those full number of points, which means you're going to need to spend $75,000 on the card. So if you compare this to the previous card, there is a higher hurdle. However, on the Palladium card, that $75,000 of spend would get 2x points. So 150,000 points plus the 100,000 points from your mortgage or rent, making it a 3.33x card up to $75,000 of spending. So the quick formula in my mind is however much your mortgage or your rent is, multiply it by 0.75 and annualize it to a year. So let's just assume for the sake of the previous cards cap, if your annual mortgage and rent payments is a hundred thousand dollars, then on up to $75,000 of spend on any of the built cards, you earn an extra 1.33x points. So if that's the built Obsidian card, now instead of earning 2x on travel and 3x on dining or groceries, though, the groceries is capped. So if it's 3x on dining, it would actually be 4.33x on dining up to $75,000 to spend on the card. So when I look at it from that lens, the cards look a lot more interesting than I thought. If I look at it from the lens of the old built card would let me get points on rent up to 100,000 for free forever, every year. By comparison, it's not that compelling. But now if I just forget that and look at it directly, it's a lot more interesting. Okay, back to the episode with Brian M. Let's talk about Mesa.

[C]

I think that's a great transition to talk about Mesa, because I agree the built cards are set up for sustainability now and Mesa wasn't.

[B]

Yeah. So for those who aren't familiar, Mesa was a card that led you earn points on your mortgage, you didn't even have to pay your mortgage through the card. And they had a bunch of 3x categories that other cards didn't have, like insurance and daycare. And so it was kind of exciting to be able to earn 3x points on categories and 1x points on mortgage, all for a no annual fee card that even had quarterly and monthly credits on things. So it was great. What wasn't great is that for reasons that they still haven't explained, they went out of business or at least shut down the cards program in a matter of hours with no notice. And so I don't think you had one. So I'm curious what your reaction to this was and then I'll share mine. As a Mesa cardholder.

[C]

Yeah, I would have loved to have one, except for the ending, obviously. It seemed like it was too good to be true, and maybe it was. But I think watching it as an outsider, the most obvious risk was, you know, this is a startup and where could things go? And the lesson learned is what do you do based on that risk that was perceived? And the obvious option is, well, don't interact with them. But I just said I would have loved to have the card, right? So that's not the option I'm going to go with. And I'm going to, in the future take the lesson of being cautious with startups and new to market opportunities. And in Mesa's case, just kind of dissecting postmortem. Maybe the answer was we'll transfer out points as immediately as they come in. But of course that reduces the value in having a flexible points currency because you want to strike when the opportunity is there and let the balance wait for that opportunity.

[B]

Yeah. One, the experience as a cardholder and as someone who shared it, you know, I thought it was great. I didn't have any investment in the company. I had someone at the company that responded to my emails until they didn't. And what I experienced though is I was driving to a holiday party and I got, I think it was an email that was like. Or a post somewhere that was like, MESA cards, like, just not working right. And for the week before, various transactions were getting declined, but everyone was told it was part of this banking transition. And I'd gotten an email from them saying, yeah, we're transitioning banks in January, as early as two days before they shut down, I was getting emails from the Mesa team about like, oh, we're transitioning, things are going to be great, we should do something fun. And like. And then boom, overnight it went under. Or at least they shut the card down. The experience as a cardholder was stressful because it was like, what do I do with the points I'd earned? It felt like there was like a ticking time bomb of what do you do? And if all of this is not a forever problem and they're just declining cards temporarily, I'll leave my points in here and some people transfer them out immediately and some people didn't. And I will only say that while it's not the best option. The fact that Mesa made good on cashing everyone's points out as statement credits, even if it resulted in a negative balance that they said. And I don't know if it's happened yet, but they said they would pay out those negative balances. I think everyone thought that the points were just gone, right? Like everyone thought if you had 500,000 Meza points, you went, you're going to end up with zero. You know, if you had 20,000 zero. But they cashed everyone out, not as good as if you could transfer them to partners, but better than if you went to zero. And so that was nice, but it kind of gives you a lot of apprehension about, do I want to sign up for this new card from this new company that could go out of business in less than a year and what do you do with the points? And I think we're going to see a lot more of this because what I haven't heard a lot of people talk about is that the way Mesa worked is that they partnered with this company called Ascenda. And Ascenda is like a third party that makes it easy to fulfill points transfers. And so ascenda has like 50 plus airlines and hotel groups. So it makes it really easy for companies to just spin up transferable points programs. And that means that startups could make really exciting, compelling credit cards for people that are enthusiasts like you and I, because they can turn on transfers to all these programs instantly. And we've seen it with Rove Miles. There's a new brokerage firm, I don't know if you've even seen this yet, called Silo, and they basically pay an ongoing brokerage bonus in points that they're saying will be transferable to other airlines and hotel groups. There's a fee, and I think the fee is $80 a month to earn up to half a million points a year on a balance of half a million dollars. So 1x points on your balances. So if you valued them at a cent and you had half a million dollars, you'd earn five grand and you'd pay $800 times 12. So it's basically like a $4,000 of profit if you could put 500,000 there. And I was like, oh, gosh. Brokerages are now offering transferable points on their. Like, it's kind of wild. And this Silo thing, you know, and then I'll come back to Mesa. But the Silo thing, that was interesting. So I signed up for this account. I don't know anything about the company. But it's built on top of Interactive Brokers. And so I'm not worried that my assets, especially if they're under the SIPIC, like SIPC limits, like I'm not worried that if I buy some Vanguard ETFs at a brokerage firm like Interactive Brokers that something's going to happen to my savings. There might be like a few day delay and accessing them if the company goes out of business. But the points thing is interesting and the ongoing brokerage bonus is interesting. So I'll come back to Silo another day. I'll put a link in the show notes. I think there is like a referral bonus to earn extra points. So I'll put a link in there. But the idea of more and more transferable points programs from startups I think is going to be good, but with some apprehension of like what happens to these programs.

[C]

Yeah, I think that's great. And the details of the setup behind is really important to understand that MESA may just be the first of a similar line of opportunities and learning lessons as we go will be really useful.

[B]

Yeah, I think the hardest thing is the most exciting opportunities for people like us are the ones that get outsized value. So we have a selection bias where if Someone launches a 1x everything card with transferable points, where like on one hand it's like, that's really sustainable. I should feel good parking a balance there. But I'm like, why don't I use that card? It only earns 1x points and it's hard for me to transfer points speculatively. And what I ended up doing with MESA was I dumped all my points into SAS or SaaS. It was totally irrational, but it was like it was the only transfer partner they had that no one else had. And I was like, if I ever want to use sas, this is my only shot. And I dumped all these points there. And then I later after that was like, oh man, these points expire. Like, Like I don't think that was a good decision. But I kind of panicked and so now I got a lot of, I guess we're going to Copenhagen or something.

[C]

Like, hey, sometimes that's the best reason to plan a trip. Yeah.

[B]

So any other thoughts there? And then if not, we can talk about planning a trip.

[C]

No, it was very interesting to watch as an outsider. That's really the most input I have because I was not lucky enough to have a MESA card.

[A]

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[B]

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[B]

Hacks I do want to talk about planning trips. I've learned a lot from you, but real quick if you think about like what's coming in the year ahead with cards, with programs, with new offerings, is there anything in your mind about what we might see this year or in the days ahead in the loyalty space, point space?

[C]

I think there are a few things. I think you touched on it with your reference to Ascenda and the opportunities for startups to have transferable programs. I think there'll be more of those angles in 2026. Mesa, Rove, the Rakuten built lineup, those are all kind of different ways to go about it, but all interesting to those of us who play in the miles and point space. I think similarly co branded debit cards, Wyndham, Southwest, United have all come out and that will be continuing is my best guess. I do think that airline and hotel elite benefits continue to be less about the benefits having to do with the travel or the stay and more about other non direct benefits, whether that is through partnerships like the Hyatt and American Airlines milestone options or or through United plus points being usable for things other than the obvious upgrades. And then I've flown Southwest a lot. You've flown Southwest a lot. Southwest had major changes actually as we record, the final major change of assigned seating is not even in place. But I think the transition has happened. So it will be an interesting year to Watch Southwest in 2026, how they are doing in the market. We know how they've positioned themselves. But will their strategy be successful? I think it will be. I think there are folks who would not have flown Southwest but will now despite not having a true first class, they have that extra legroom seating option that many people are looking for these days.

[B]

I can't remember, I think it was Delta just announced that revenue for economy is down a billion dollars. But the airline's making more money than ever before because people want premium economy. I mean, I think Delta is one of the few that actually has domestic premium economy and charges for it versus you know, economy plus and other things. They kind of charge for it, but they give it away for free. If you have status and Delta no, you know, you might get upgraded to it at boarding, but you don't actually get it for free when you're selecting seats if you book far in advance. And so there's clearly a demand. Everyone loves Southwest for the companion pass. Do you think that sustains all these transitions they're making?

[C]

That's a tough question. Until they eliminated bags fly free. I would have said the companion pass is definitely staying, but I would have thought the companion pass would go before Bags Fly Free went. So I don't know that I'm the best predictor, but I still think it is such a unique opportunity. And I don't think it costs the airlines as much as it may seem at first blush because many planes are not going out 100% full. So the cost to the airline of that seat may not be the cost of the fare that it was sold at any point. And the benefit may be that folks are flying Southwest that may have chosen a competitor instead of flying Southwest. So I think on the net side, it is not necessarily that costly. And I'd be really curious to understand whether it's break even or better.

[B]

I also think as someone who has Companion Pass right now, I was doing the math like, oh, for 2026, should I spend enough either with Southwest or on their cards or open new cards to get Companion Pass? And you know, I think a lot of us in this space, at least myself, have some weird obsessive compulsive problem with trying to earn status even if we don't need it. And I looked like we only flew Southwest a couple times and I should have taken note, but I don't think every time we took it it was necessarily the cheapest option. Now, it probably was not more expensive enough that it would have been cheaper without one ticket free. You know, like it wasn't so much more expensive that I wouldn't get more value because we got one seat free. But my annual savings from having the Companion Pass is not tens of thousands of dollars. For me, it's probably measured in hundreds of dollars. And the amount I spent to try to earn it is certainly valuable to Southwest. It's not like their credit cards are the most lucrative earning credit cards out there. So the spend that you would put on them or the referrals you would make to other people or the flights you would take, like those are all value to them. So I don't know. I hope it is there for a while. We'll talk in travel about potentially leveling up and earning two of them and then it make it even more lucrative for the family. But I don't know, I hope it stays because I think it's such a unique benefit. But gosh, I feel like if the changes they've made so far don't have a financial impact on the company, I just wonder how hard they're willing to cut towards all the things they offer.

[C]

Today, the easiest road for them is to increase the requirements for the qualification or to limit its use. Instead of unlimited, it's limited to a certain number of times or instead of upping it to 150,000 Companion Pass qualifying or 200,000 Companion Pass qualifying.

[B]

And then the only other big points and miles news that's kind of circulating the Internet right now is this current proposal that we cap interest rates on credit cards at 10% for I think it's just for one year. So this is not a politics show. I don't want to talk about the politics of it, but any thoughts on what might happen if that happens or whether it would happen?

[C]

I don't think I'm particularly qualified, but I've seen a lot of proposals in the space that would impact credit card rewards or debt related to credit cards come along and the majority of them don't result in law. And I suspect this will be similar. But I'm no expert. What about you on that and other 2026 forecasts?

[B]

I just looked at Kalshi. The current betting market on whether the credit card rates will be capped is at 31%. And so I would say it sounds like the market doesn't think it's going to happen, but that's not zero. I think one of the biggest challenges is that there are a lot of things that get proposed that the second and third order effects don't get considered. I don't think that the reason that credit card interest rates are so high is entirely that banks are greedy. I think there are people for whom those rates are commensurate with the risk they take. Is the system perfect? Do I think, given that I have never missed a payment, at least not intentionally and not by any significant margin, am I so risky that I would need a super high interest rate? Maybe not. But you know, I think there are people that have access to credit now that will not. If the banks are forced to drop those interest rates, I think people's limits will get slashed. I think cards might get closed. I think there'll be a lot of effects that aren't all rosy and perfect as it sounds like. It sounds as a suggestion that, oh, everyone's just going to have less interest and it's going to be cheaper. But the reality is there are a lot of people who, even though I would say this isn't the cheapest form of debt for most people, for some people it's the only option. And I think that's not great. But again, I think it's unlikely to happen. It just would cause so many problems. I don't actually think it would result in as much of a devaluation of Points and miles. I got a lot of questions from people like, are our points going to be worth nothing? I think it might devalue how we earn the points if it were to happen, but I'm not sure it would devalue what the points are worth themselves. I like you think it's unlikely to happen. It seems like the betting markets would agree, though. The amount of volume on that was, you know, $10,000. It's not a huge betting market on it. So I don't know how much to rely on on the betting markets for this. As for other stuff, it seems like there's a few other platforms, I think, that also enable these point transfers. So we're going to see a lot more flexible points all over the place. The idea that a random brokerage account would pay you transferable points to airlines is kind of wild. So I think that's a big thing. And I'm a little biased here because I'm in the middle of building something in this space. But I think historically the tools around points and miles, everything from tracking and managing to award searching, the tools have been getting better and better. And I just see that continuing with everything that different language models and AI software tools have enabled. You know, I've been annoyed that no one has built a good points management card management tool tool for the specific use cases I had. I've used a Ward wallet for a while to track balances. And it's like, it's painful and it's not their fault necessarily, but I was able to build an entire product that does everything I want for me in a matter of days. That feels like the kind of software I would need years and millions of dollars and multiple employees to build as little as five or ten years ago. And so different tools in this space that allow you to kind of calculate anything, search anything, book anything, are just going to get better and better and better. And I think that's good for everyone. It's maybe slightly worse for the people who, you know, love to find the unique things that'll now be easier for everyone to find, but we'll just take advantage of the more advanced tools that do more interesting, crazy things. And so I think that it's not specific to points and miles, but I think the impact of all this customizable software that can be done and agents that can go do things on your own. Like, I would love to have a piece of software that manages all my bookings and I could just say, go cancel this booking and something goes to the Southwest website, knows my preferences of, you know, I want, you know, a credit or a refund and could just go do everything. So I think that's kind of cool. What else? I think less change on the credit card front. I don't think we're going to see anything wild like, oh, sign up bonuses are going to 5x or go away or anything like that. So I think probably not a lot of major things happening, but maybe a continuation of any card that is in your wallet that is issued by Chase or Amex that isn't filled with coupons, probably will be. So if you've long loved, you know, the Hyatt card or something that feels like, oh, it doesn't have a bunch of coupons yet, maybe when it relaunches, which is supposed to happen, maybe it will. Yeah.

[C]

Built one that way, too.

[B]

Yes. Yeah. I mean, it seems like everyone's going the way of the coupons to the point that I think when Amex first launched hotel FHR and hotel collection credits, it was like, okay, like you, maybe once or twice a year I could use this. Maybe I'll go to Vegas where, like, you can actually make it work because the hotels are cheap enough that you don't have to spend fifteen hundred dollars a night to get your two hundred now, three hundred dollars of credit. But now I look, and if you have as many credit cards as I think you and I do, there are just so many credit. I would have to stay at a hotel like 30 nights to use up every single credit and free night certificate and kind of travel credit and et cetera, across all the cards in my wallet. Now, that's a personal problem, having too many cards. But it just feels like the value of the credits is going down the more I have. I let many hotel credits just go unused because it was like, I just, I'm not gonna stay in a hotel that often.

[C]

Yeah, same. I also had credits expire unused and just move forward.

[B]

Yeah. But I think you have to take a hard look at what you really value these things at. And that's one of the things I was trying to build into this tool that I was working on. Is, is this card worth it? Well, AMEX will tell you. Yes, you've got. I think I have one of these mailers here. It's like, there's nothing like platinum with over $3,500 in business and travel value. That is what they're telling you. But what you really value that at needs to be calibrated. Because if a friend came to me and said, hey, could you book Me a hotel room with your Amex FHR credit and get me $300 off a night and I'll give you 50 bucks? I'd probably say yes. So, like, that credit is not worth $300 to me. And so if you calibrate for what all these credits are actually worth at some point, the annual fees approaching $1,000 don't make sense. Now, in some cases they do. In some cases, you're really able to buy your OURA rings, flip them on ebay, and do all this stuff. But how much work is that really? I think I'm losing patience for trying to cash out credits for tens of 20, 30, 40, $50. And I'm just going to start not using them, which means they're worth zero, which makes me look at, you know, a near $1,000 annual fee slightly differently than I would have in the past. And mostly because I feel like my time is just not worth trying to buy an aura ring to get $200 off and sell it on eBay and drive to the UPS store to ship it out and all to make $60 of profit. It's like, that just seems like too much work. So if a friend wants me to buy him an OURA ring, great. But otherwise, I think that credit's got to be worth zero unless you want the thing. And so I'm going to take a hard look at annual fees as they come up this year. But I guess one question I'll ask, I'll kind of interject listener questions a little bit here. When you get an annual fee coming up. You know, I get this question all the time. How do you approach annual fees coming up on a card? What do I do?

[C]

For me, the number one rule is not to cancel during the first year. But if the annual fee is coming up, it means you're probably out of that. Right? So I think about whether the value I get from the benefits exceeds the annual fee. And that sounds simple enough. But go back to our discussion about valuing a $300 credit at only $50. That gets really granular. I mean, to that end, this week I canceled my business platinum because even with the $300 added to it, it wasn't valuable for me. And so it is important to decide whether the annual value. But that can get tough in measuring, right? Because some of those benefits are non obvious and might be just the ability to earn certain things that you might not otherwise. If one is really into American Airline, having the card to spend on can give them the opportunity. It can also be a card that's no longer available to new applicants. Right. A lot of folks into miles and points have the Ritz Carlton card. If you cancel that, it's pretty difficult to get that again if one wants. And then there are other cards that you really can't get anymore, like the City Prestige. Then there are cards that I had trouble getting in the first place. The Atmos Summit, Infinite Visa. It took a couple tries before bank of America was willing to give me that card. So I think as I look at it, it's am I getting the value from the annual fee? If I'm nowhere near it, it's probably getting cut, canceled. If I am close, I might look at what are the intangible or non obvious benefits that I'm getting by having this card. And obviously if it is exceeding the benefit, I'm probably keeping it. However, even then keeping it might be an opportunity cost against the ability to get a different card because it might be too much credit extended at that bank. And the bank doesn't reallocate. Right. Thinking Citi there. So I think this is often a more complicated question for me than it seems at first blush.

[A]

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[C]

Are there other factors you think about when you're analyzing this on a card by card basis, two, three, four years.

[B]

Ago, I would more heavily weigh the likelihood of getting some kind of retention offer with a way to kick the can down the road. I agree with the first sentiment you said. I try not to cancel a card in the first year. And that doesn't mean that I try to pay the annual fee twice. It just means I would never consider canceling it before 365 days. But when that annual fee posts, I might cancel it after the annual fee is posted, after it's been a year, but before I can no longer get a refund on that annual fee, which I'm sure is your approach as well. And so if you're going to cancel it, I would wait and I would weigh two other things in there. One is, I feel like five years ago I would message Amex anytime an annual fee came up, and they'd be like, here's some great lucrative bonus to keep the card open. I feel like that happens less now than it used to. And I'm curious if you have different luck. And so that's one thing is if you're looking at a card and you're like, gosh, I'm going to spend $900, but I'm getting $600 of value. And you message Amex and they're like, well, we'll just waive the fee for the year.

[A]

I'll probably keep that card open.

[B]

If they're going to knock off $100, maybe you won't. And so that's a data point that I try to get. However, in the past, at least you could chat with a rep one day and get a good offer and not take it and chat with the rep the next day and get a worse offer and regret not taking it. So I like to do my calculus of like, how close am I before I ask if there are any offers which can be as easy as a live chat or a phone call and just say, like, the fee is really high. I understand all the benefits. I could consider keeping it open. Are there any, any offers that might make that decision easier for me? Whatever script you want to use for that conversation, that's one. And then the other is kind of, what are any effects of closing the card? And are there other ways to mitigate them, like downgrading a card? So I have cards that I've had open for 20 plus years. And so they're like, if you look at one of the factors of your credit score, it's like your Average age of accounts. You know, I have a strong bias for not closing a card that I've had on my credit for 20 years. So in some cases, you could downgrade, you know, a Chase Sapphire Reserve to a Chase Freedom Unlimited with no annual fee and keep that part of your credit with that long extended history. In some cases, if you have an AMEX card and it's your only Amex, let's say you only have an AMEX Platinum card, canceling that card is going to mean that you forfeit your balance of Membership Rewards points. And so you either need to figure out what to do with them, or you could transfer that card to a lower annual fee card like the Green card or the Gold card. Or if you had a second one, it would be a different calculus, right? If you already had the one no fee card, the Blue Business plus, that lets you have Membership Rewards points for no fee, well, then canceling your Platinum card wouldn't have that effect. So it's like it's not only complicated to calculate the value, but it's complicated to think about the impact. But I think the simple order of operations for me is, is this card worth having? And if so, it's pretty easy. If not, can I get a better offer? And if I can from amex, that makes it worth it. Kick the can down the road a year. If I can't, then is there something I can do that, you know, makes the canceling better? Downgrading, maybe reallocating my credit line before I cancel or anything like that. But if it's a card I've only had for two years, like if Mesa, instead of coming out and saying, hey, we're shutting down overnight, they said, hey, we're now a 1x everything card. You can't earn points on your mortgage. And the annual fee, $700. Well, it's not really having an impact on my credit because I've had it for a year. I would just cancel it. I'm not too worried about it if it's that case. But for some of these cards that have been there for 20 years, I appreciate the impact it has on my credit score.

[C]

Yeah, that's a great order of operations to think about the process and decision making.

[B]

Have you been getting retention offers lately? Like, is it. Does it feel to you like that used to be a great way to subsidize your annual fee and now it feels less like a great way to.

[C]

Very similar to you. I have also reassessed the effort that it takes to call or chat depending and try to solicit a retention offer against the likelihood of success. And I think that second part is what you were getting at. It has been less likely to be successful with certain banks, Amex in particular, lately. And I have felt the same way. It's been a little bit since I've received a retention offer that made or broke the decision about whether I was going to keep the card or cancel the card or downgrade the card.

[B]

Yeah, I mean, there was a window. I remember I was in Hawaii at the time, and I called amex and I will just waive the fee. And I was like, well, that makes it easy. Like, I haven't heard that happening a lot. So we'll see. Now, we talked a lot about points and earning them. Let's talk a little bit about spending them. Because I think you have, you know, a pretty systematized approach in how you think about this. And I think one of the most frequent questions I get from people is like, how do you think about actually planning your trip? I am not as good at this, so I'd love to hear you just kind of share or walk through your process of how do you try to get the most out of planning a trip and how do you think about it so that you not only get value, but you preserve some flexibility?

[C]

Generally, I value booking flexibility higher than most, I would say. And I think that booking flexible options gives me the ability to change and cancel reservations in a way that just wasn't available pre pandemic. The change in cancellation policies, especially on award bookings these days and flights in particular hotels were always a little bit more cancelable and especially rental cars were. It has made the way I approach this a bit different. The available options that I book may change, whether they are impacted by a schedule change or a new option may become available. I book the best available one connection itinerary because every connection, every itinerary was connecting. And then later a carrier decides they're going to announce and fly a nonstop service. So I garden those over time by monitoring them and making a decision whether kind of like keep cancel or downgrade, whether I'm going to change them, keep them where they are, modify them in some way to efficiently make the best available booking for me at that time. This is optimization talk, which is very important in this space. When I'm thinking about a particular trip, my first consideration is, what's my travel party? Who are they? Where are we going? When are we going? Why are we going? And how are we going? So how many travelers are coming? The who? What Number of seats. Who are these travelers? What do they look like? What are their needs? Is kind of the. What do they have requirements or components? I've flown with folks who really need an aisle seat because they need to visit the lavatory. That's fine. But it can be a consideration when booking. If we're going to Europe in the summer, it can be hard to find places with air conditioning. But you may be traveling with folks who air conditioning is important. Where are we going? Is the destination the thing or is it more important that we're all together? How important is that destination? Is it something where the very specific hotel like a Leela Ventana Big Sur or something like that is a place you want to go, or is it, well, hey, we really want to go to a beach destination and are more flexible with the where, the when. I mean, especially with kids. Those date restrictions on travel due to children's school and other activities can be really impactful to the trip planning process. Why are we going? Is this a chance to get outdoors in nature? Is this a chance to go visit grandma? What is the purpose of the trip? And then how are we going? Are we driving? Those aren't many of my trips these days. It's usually flying. And is it nonstop flights? Are those available? Is it practical to book those nonstops? Right. I'm looking at some travel to Europe. Where from Chicago, where I'm based, there are nonstop flights, but there's definitely no award availability for those nonstop flights that happen, you know, three to seven times a week. And that kind of gets me started thinking about the trip. And then I pivot into thinking about the travel party's limitations and flexibility. As I narrow the scope of the specific bookings I'm going to start looking at, then I include the resources that are available. You know, if it's just my nuclear family of husband, wife and kids, we know what we have. Well, I know what we have and we can get access to that and make those bookings. But if, as I've done, planned multi generational trips, it's important to think about what do the other travelers bring to the table? What are they looking to use to book and how are they looking to book those things? And then for the specific trip, is there any sort of limiting factor, whether it's the flights like, you know, the Lila Ventana Big Sur, the destination is the thing. So you're going to find flights around that. But maybe you found a unicorn saver availability flying to New Zealand and you're flying on that date because that was the hard thing to get. And then you have to book the rest of the trip around that. Is it dates of spring break? Is it. You have to be back because there's a wedding of a relative you have to attend, or that's why you're going. So that's all before I really get to booking. Is thinking a lot about the booking itself. Who's going, why are we going? All those factors.

[B]

I probably don't spend as much time thinking through some of those things, but we recently got this massive calendar that I talked about in this episode last week, I think, where it's basically a full year and it's like 4 by 6ft. And we started planning the year and then we started to do some of this. It was like, why are we wanting to go? Is this just. We want to break up the summer where it's like, literally, it's not even about where or like you. We want to sometimes take a specific trip to visit family or to go skiing or something. And so, you know, it's like, how much flexibility does the trip offer? And I usually fail the hardest when there's unlimited flexibility. When it's like, we want to go somewhere in August, that's nice. In Europe, it's like, great. The number of routes times the number of days we could fly, times the number of hotels we could stay at, even the countries we could go to and the cities within them. It almost feels like I don't know where to stay start. And it's kind of a funny one, because I know you're planning a similar trip to a similar place in a similar month. And so I've struggled the most with, like, gosh, what's the thing that I use to start narrowing it down? Is it the award availability? Is it I find a hotel and just say, okay, this is the anchor part of the trip that lets me rein it in. Is it something else? I don't know.

[C]

One thing I do when I have unlimited flexibility, and this has definitely changed over time for me and really didn't come about until we had kids, was I'm booking at the leading edge of the schedule much of the time. And so that's usually 11 to 13 months in advance. Well, that's about this time of year as a mental exercise. What I do is think about where would I want to go on a trip right now? No constraints. Where would I want to be right now? I'm in Chicago today, in January, it's snowing. I would rather go somewhere warm. So as I'm thinking about booking at the leading edges of the schedule. That helps me narrow down from a unlimited flexible world to some specific options.

[B]

And I assume the reason you're doing that is that the award availability is often easier if you're booking right when the schedule opens.

[C]

Absolutely, yes. That is exactly why I've pivoted to that. When I have four travelers, are there.

[B]

Destinations where you find that's easier rather than harder? I know for us, we have only ever successfully done this once for a trip in a few months to Japan, we booked right at the schedule open. Even then, I would say for a family, we could not find four seats together. Like, I knew the flights I wanted, I knew they weren't even going to have four seats together. So like it wasn't like a surprise. But I think for that particular route, even schedule open doesn't matter. But now, you know, I'm kind of kicking myself for the idea of going to Europe this summer, having not done that seven months ago, but had I done that? Is Europe a place where finding those seats at schedule open can be a lot easier?

[C]

That is what I found. Yeah. We were able to get four seats in business class on the nonstop to and from the airport. We were looking for. For one of the ways, not for the other way. Having, as I do monitor space ever since booking, it's not there. It will pop up periodically, but usually not for four travelers.

[B]

Yeah.

[C]

So speaking of flights, as I think about booking flights, I often think about what are the elite benefits that travelers may have? Do I need that status benefit? Does it apply to multiple passengers? How many passengers are there? Lounge access considerations, especially if I'm connecting. So if you have a family of four, but the two adults have one world emerald and you're connecting through a one world hub, you're going to be able to bring in one guest with you to the first class lounges, not just the business class. And that may or may not be important to different folks for different reasons. But those elite benefits, even on a domestic flight, if that means you're going to get extra legroom seating for your party, well, how many. And does that impact whether you're going to book a single reservation or whether you're going to split the reservation in order to maximize the extension of the elite benefits, depending on who's in your.

[B]

Party, I will only say that one thing I've seen some people email me about that I want to push back on is I'll get an email from someone. They're like, I'm a huge Delta loyalist. I have all these AMEX points also, and I want to take a trip and I'm trying to do it on Delta in business class because I have Delta status. And I say, well, just hold on one second. Like if you already have Delta status, you're not going to earn any status from the award travel. You're telling me you want to book in business class. So I just caution people sometimes to say, does the status matter? Because if you have Delta status and you're going to book with points and you're going to book in business, is there fundamental difference between flying Delta or United or Lufthansa or Japan Air, like does it even matter? Because you might be narrowing your set of options by saying you want to fly on Delta, when in reality, if you're already going to pay for business, the elite benefits you might get, like you're going to get a free check bag, you're going to get a lounge access, you're going to get the flight. So ask yourself, in some cases it really does matter, but in some cases it might not matter at all.

[C]

Yeah, absolutely. And when it comes to talking about different airlines, that's where partner availability is really important, right? Is the flight I'm looking at available only because I have a card member discount benefit on United or is this a partner award availability through a Star alliance partner that is bookable through a different means where either I already have currency whether I transferred it to SAS as one may need to do from time to time, or is it a option to transfer at that time to book for either fewer miles or through some way that will lower the taxes and fees that are applicable on that? Or is it important to maintain the flexibility of that reservation? So I want to transfer it or use a issuing carrier that will have the flexible nature to cancel or change in the future if something better comes along or if it's impacted by a schedule change or simply kids get sick, Right? That happens.

[B]

There have definitely been trips where we're like days before we're like, we should just bail on this trip. And when you booked it with points, you're like, oh well we can. And when you can't, that really sucks. What tools are you most often using.

[C]

To do a lot of this searching for domestic travel? I really enjoy points path. I think the seamless integration with Google flights makes it really good. And the support for the domestic programs is excellent. For international long haul, I primarily use seats Aero, but I also brute force search engine by search engine because there are things like the United card member discount even on international business class for United fares that can come about and afford opportunities that those search engines are not going to show me.

[B]

Yeah, that is one where I think this kind of personal software where I can log into United and have something do searches on my behalf might be really interesting, but it's one that I often forgot and for the purpose of summer, you reminded me of and I was like, oh my gosh, I was just using Award tool or Seats Arrow and I wasn't finding anything but I forgot. Oh, if you do have a United card or United status, sometimes something better shows up and some carriers are really good about it. We were talking about how if you have Air France platinum status, it's like a whole different calendar. Like I was looking at flights for SF to Europe and it was like the cheapest fare I found was like 200,000 points and someone with Air France platinum status, it was like half the month was available at 50,000 points. And so add that to the bucket list of statuses that I would like to try to achieve to make a trip I take once every three years cheaper. But you know, I can't stop playing that game.

[C]

Yeah, absolutely. And flights aren't the only consideration. We're obviously going to stay somewhere when we travel. So looking at hotel bookings, I think it's helpful to understand what one's needs are for the trip before booking or at least as booking. There are some places where the trip is to go to an all inclusive and not leave. And then you're limited to looking at certain types of redemptions and needing to understand whether there's going to be a cash copay or whether it's included in the points or certificate instrument you use to book. Is it something where you need space? So you're looking at like a vacation rental or at least connecting rooms in a hotel. And the options for vacation rentals are varied and sometimes they may appear in those bank travel portal search engines, sometimes they may not. Is it a strict hotel that you're looking to go to and whether you need more space? Is that a suite or is that a connecting room? How are you going to get those right? Is there an instrument or can you book into suites directly like with leading hotels of the world or Choice or for a subset of the type of hotels? Right. Hilton, you can book at a standard award into suites in some of the brands that aren't necessarily the most luxurious. But Embassy suites, they're all suites and maybe that space is what's important. Residence Inn with Marriott, you know, sometimes you can book into a one bedroom with the certificates, the upgrade instruments that are available to you. A lot of people enjoy Hyatt Suite Upgrade Awards because you can confirm and do a suite at the time of booking, which is extremely useful if you need that certainty when you're traveling with a group or a family. When it comes to connecting rooms, I think that's a much tougher thing to guarantee in advance. Hilton has the confirmed connecting room for some hotels when booking online, which is good. Hyatt can be done as well with things like the family plan rate.

[B]

Can you remind people how that works? Because for some reason I've heard it like three times and I forget, but it's like the second room is half off or something.

[C]

So the first room can be booked on any eligible rate, which can be points, I believe, certificate that isn't one I've done, but or a paid stay. And then the second room, which is intended for minors, is kind of quirky. It's kind of attached to the same reservation, but the pricing of it is up to 50% off of the standard rate that prevails at that time is not always 50% and it's obviously the before taxes and fees 50%. When I've booked these, it's usually through calling Hyatt, because when I am looking for it, I'm almost always looking for a connecting room. And the phone agent is either able to see in their system which are the room types that connect and thus guarantee it either on their own for some hotels or by reaching out to the hotel and having the hotel block specific rooms for the dates of stay in connection with making that reservation.

[B]

But is that all Hyatt brands?

[C]

I don't know that it's available at all Hyatt brands. It is available domestically and internationally at a lot of brands.

[B]

Yeah. It might not work at like Mr.

[C]

And Mrs. Smith, but I would suspect it does not. If it's a Hyatt Regency, I would think it most likely is available for some periods of time because there are also blackout dates that you just have no idea what they are. So the same hotel may offer it at some point in time, but not other points in time. I mean, I've been able to do it on peak travel days and I've also been told it's not available on peak travel days. So it's very much a. Your mileage may vary.

[B]

It's a little bit in conflict at some times where you're like, well, if it's an incredible points value. Right. Like if I'm getting this fifteen hundred dollar room for, you know, 25,000 Hyatt points, I feel like I won the lottery. And then I call to add a room, it's like, well, that room is now going to be $750. So it's like, you know, you don't want it to be the best ever points redemption, otherwise you're going to pay a lot for the second room. But it's definitely, as our kids are getting a little older, I think for whatever reason, it's like the crib next to the bed, like we need beds. Connecting rooms is often the way to do it and we haven't done a lot of that, but I think that's in our future.

[C]

Yeah, well, the other thing that connecting rooms always gets you, that suites don't always get you is a second bathroom. As kids get older, that can be very, very useful. Another aspect that is kind of the in between of vacation rentals and hotels is the timeshares. And I feel like there is a point in time where that was talked about a lot in the points and miles community. And it's not as much anymore. But there are a lot of Marriott, Hilton, Hyatt, IHG and Wyndham, for example, timeshares out there that can be booked for points or certificates that can be really useful because they're often larger units. And it's that kind of hybrid where you might get a kitchen and feel kind of like a vacation rental but still be on a resort type property where there are amenities in a restaurant and activities for folks to do.

[B]

Yeah, I did look at a couple of those recently because we were. This year was our like winter of skiing and there's a. I think there's a Hilton timeshare one up in Tahoe that we looked at doing and it didn't work out for the dates. But I was surprised that the points rate was pretty decent for a large place.

[C]

Yeah, they can afford really good opportunities and we've gotten some really good values, especially when we've showed up and there's like activities, free activities every day they have a calendar and it's like, wow, this, this is pretty great. I mean, I know resorts often have those, but we go into it kind of thinking it's more along the lines of a vacation rental than a hotel. So that's always nice to find. And then once everything's booked, I'm not done. Right. This is, I'm not Billy Mays. This isn't set it and forget it. This is just the beginning of the process. And I'm not necessarily booking all of these things at the same time. Right. The flights may have been booked long before the hotel or the hotel long before the flights. And as time goes on, I'm consistently monitoring the reservations and looking at alternatives to decide whether I'm going to change or modify, cancel, rebook, whatever may be available to more efficiently make it a optimized trip or a better trip. Right. Sometimes we change where we're going to stay because the plan has changed and what we're looking for out of the trip has changed and it just continues. And you know, as far as tools, there are some great tool alerts out there. And whether it's CST Air or pointpath that I mentioned earlier or others that will alert you if you know what you're looking for and can set it so whether that's a drop in the fare or a reduction in the room rate of the hotel, or a availability on a partner award for a non stop flight that wasn't there when one first booked, that now gives you the ability to make that trip much more pleasant because you're not spending six hours connecting in some airport that you didn't want to go to anyway.

[B]

I set a lot of alerts and for our trip this summer, we're planning on going to Europe in August. It's like, okay, well there isn't what we want now. We didn't plan like you did. So it's just all the alerts coming in as things pop up and booking flexibly because, you know, we're willing to change planes or we're willing to fly direct into a city that we're not planning to go to and just buy a ticket from there or use another program from there, but I'd rather fly direct. And so we'll book the best we can and then we'll wait to hopefully find something better. We're always going to book something we would take, like it has to be a thing we're willing to do. And the one constraint I've come up with that I think I'm curious if you know, the answer to is if I'm trying to book a flight, if I find the availability to, I don't know, Frankfurt, but I don't even know where I'm going in Europe yet, could I book the flight to Frankfurt and then change it to connect in Frankfurt and go to, I don't know, Paris or Zurich later. Right now we're not sure where we're going in Europe. And even if I find a flight to Munich or Frankfurt, I could book it, but I Don't know where to like, oftentimes if I connect, it would be free, but I don't know yet and I don't want to wait on it.

[C]

So the short answer is, theoretically it's possible depending on the program, but it's going to vary on a lot of factors. Not all programs are going to allow you to change the destination on an award ticket. And some may not allow it unless you're impacted by a schedule change. And then they may allow it to a geographical limitation. I think it was United that allowed within 90 miles and great circle miles when I've had changes in the past and that was interesting, that was one to Hawaii. So now it's like, oh, well, I could go to a different Hawaiian island, change the trip entirely. And then there are just programs where there's no real change or cancellation available anyway. So the answer is probably no. But again, if it's impacted by some sort of schedule change or other outside factor, travel waiver or something, maybe the answer becomes yes because there gets more flexibility in the program rules when those outside factors impact the reservation.

[B]

I got a lot of work to do on this trip that we're planning because right now we have like four countries in mind and a month of dates. So I don't have a lot, a lot ready there. I think we're almost at time. I had this idea of getting your take on a couple of questions. I'm quickly running through them just to see are any of them ones that I think that, you know, I'd be remiss to not get your quick take on and maybe I'm going to rapid fire a couple of them. And you don't have to speak from the perspective of terms and conditions on this one. But I got like five questions from people asking about, oh, I got a business card. I'm not going to hit the minimum spend with all my business expenses. Could I put a personal expense on it? Has that ever been a problem for anyone or vice versa? I have a big business expense. Can I put it on my personal card without speaking to the terms? Are you familiar with, you know, any issues with people having done this in the past?

[C]

I am not familiar with too many issues. I think it is really commonplace for employers to reimburse employees for expenses. So I don't know that I would have too much heartburn over using a personal card for a business expense that the business then reimburses it. There are lots of folks just limited to the travel space where they're excited when their employer tells them to book their own travel and the employer reimburses it because then they get both the spend and the awards. And for the inverse I think yes, the terms probably say a notice and disclaimer that cards should be used only for business related expenses. But what are business related expenses? May not always be that obvious.

[B]

That makes sense. I will say some personal cards have call outs about business expenses not earning rewards. I actually asked ChatGPT to tell me where in the built terms to understand this. Things like gift cards, person to person payments, tax payments, online marketplaces, cryptocurrency, lottery tickets, there are a lot of things they don't include as eligible. So the bill card does not say business purchases but I know there are some I think Robinhood or U.S. bank excludes like business transactions from earning rewards. So while it might be allowed to use the card for those things, you might not earn any rewards. So I would look into that. Also on the note of built, I just saw someone post that new built 2.0 cardholders, even if they were built 1.0 cardholders will get the signup bonuses. And so that was clarified. So that's interesting. One question I think you might have a good take on as we wrap. Have you been at a point in your credit card points and miles journey where you kind of just stopped getting approved? I got a handful of people email and they're like hey I'm trying to to apply for cards and I have good credit but everybody keeps saying no I'm not and they're not necessarily over 524 and running into application rules, they're just running into denials.

[C]

I definitely have run into that mostly with specific issuers. Like my first take on the question would be well look for other card issuers, as silly as that may sound. Right. And that's because there are a lot out there and they all have different approval standards. And I understand that is a bit of an end around to the question because the crux is well hey I really want this one card but I can't get it generally speaking right. Or I want this set of cards, you know, the cards that lots of folks are interested in. And so for those I have taken some measures to try to improve the chances that I would get approved. But I also try to think about for approvals particular issuers will allow reallocation of credit in connection with an approval whether they tell you they're going to do that or not. Sometimes I've had approvals where then I noticed this other card had the credit limit reduced and others I may get denied but then call for reconsideration. But even then, reconsideration isn't always successful. So thinking about what the rules are for that particular issuer and whether I may have too much credit extended and maybe reducing credit limit or closing older cards that I'm not no longer getting value for from that credit card company or issuer.

[B]

Yeah, some issuers I've found are okay with, hey, I want this card, can we reduce the limit here and move it over and approve it? And some aren't. And so if you have a lot of credit extended by one issuer, you might have to do it in advance. Right? You might have to slash your limit and say, hey, can I reduce the limit from 20,000 to 10,000 and then go apply? And you might get more likely to be approved. But I would, I would do some homework as to whether you have to do it in advance because, you know, for some issuers you do and some you don't and then some it doesn't work between business and personal. I can't remember which issuer this was, but I think I wanted to get a credit line increase on a business card, I think with Chase, and so I reduced my personal credit so that I could ask for it on the business side. Because you can't transfer between.

[C]

Yeah, those are nuances that vary and are important to consider when trying to increase chances of approval.

[B]

Awesome. I probably have a dozen other questions. I'm going to save them and answer them another week. I feel like I ran through the ones where I was like, Brian would have a good perspective here. You probably have a good perspective on all of them, but you also have a life and time to get back to things. So any other thoughts on any of what we discussed that you want to share before we wrap up?

[C]

No, I think it was a wide ranging and interesting discussion, so hopefully it's useful and I appreciate coming on and chatting with you, Chris. It's always fun.

[B]

And for anyone listening, I'm very curious what you think of this style of episode because you know it could extend well beyond points I could have other people on and talk about health things or personal finance in a more casual setting, layering in some questions people have asked as opposed to necessarily a full tactical Deep Dive masterclass episode, which is a lot of what we've done in the past. So for anyone listening, feedback definitely welcome. Send questions for a future episode feedback about what you thought of this to [e-mail] that is it for this week I will see you next week.