• Pre turkey day troubles and positive reflection

    Pre turkey day troubles and positive reflection

    We’re about to kick off the holiday season, and it’s got me feeling a bit reflective. I’m about to head off to a relaxing time in the Caribbean, powered by uncapped FNCs. Before I leave, I wanted to address the (rather consequential) MS news item du jour and share some things I’m grateful for this year.

    A large part of the churning world is collectively holding their breath right now, waiting to see what is going to shake out with a major issuer. I doubt anyone is too surprised by the situation – the clock started ticking on the lifetime of the play the second it was announced. 

    There are a lot of opinions out there on how best to deal with the situation. Play it conservatively and (maybe) live to see another day, throw caution to the wind and carry on, or somewhere in the middle. 

    Ultimately, you need to decide for yourself how you want to handle it, depending on your own personal circumstance. All of those opinions out there are just that – opinions. 

    But if I was weighing whose opinion was most valuable when making the decision, I’d trust the various people in the community who have a direct line to el jefe and not someone in a Facebook group that is LARPing as an insider. 

    And if you want my two cents, all I can do is shrug. I had my money on this lasting for six months, so I came up 33% short. This is why I like to bet on both sides when I gamble.

    For a classic #chasingcetaceanstherapythought, there’s no use worrying about things you can’t control. There is no takesies-backsies on whatever MS you did with this bank, so consider your situation, drown out the noise, and make the best decision for you. 

    Anyway, tomorrow is Thanksgiving for those of us in the states, so I’ll end this doom and gloom with some MS things I’ve been thankful for this year. It hasn’t been a year for the light-hearted, but that doesn’t mean the juice hasn’t been worth the squeeze.

    MS things I am grateful for this year, which may or may not be in chronological order:

    • Interchange fees (aka the engine of the whole thing, for better or worse)
    • Crypto shenanigans
    • Old school financial services companies
    • Hilton FNCs
    • Prediction markets
    • Citi’s IT
    • Baccarat
    • Scenic rides up and down
    • My probe group club
    • Everyone who has read, commented and been so receptive to this blog

    And some things I wish we could leave back in 2025:

    • Restrictive crypto charters
    • “Questionnaires”
    • Payment rail swaps
    • BIN blocks
    • Shutdown after shutdown after shutdown

    Happy Thanksgiving to my American readers, and to the handful of you elsewhere, enjoy us not bothering you for a couple of days. Good luck on your Black Friday shenanigans and fingers crossed you come out the other side unscathed. 

    ቺርስ! 


  • Folk advice part 3: (Don’t) wait so long

    Folk advice part 3: (Don’t) wait so long

    Companion song: Wait So Long – Trampled by Turtles this one is worth a listen if you haven’t heard it – about as cool as a song with banjos and fiddles gets

    Today concludes this goofy folk music-inspired series of timely MS advice. Part 1 and part 2 are here if you missed them.

    If you’ve found your way into this wild hobby, you probably have at least some level of personality traits that trend towards responsibility and measuredness. I think those can sometimes lend themselves towards hesitation as well, which isn’t necessarily a bad thing.

    Hesitation is your brain telling you to stop and think harder before making a decision, and in so many different scenarios, it is your friend. It’s also very natural to hesitate with financial decisions, especially since so many of us aspire to FIRE. 

    However, in this hobby, fortune favors the bold. It’s something that’s stressed from the very beginning. If you see a sign-up bonus you’re interested in, don’t wait for it to go away. If you see an award flight that fits your plans, don’t wait for your P2 to confirm they can take off work, book it before it’s gone. 

    This mantra carries over as you get deeper into MS as well. Some of the most profitable things are only around for days (or hours). In this day and age, you often don’t have the luxury of saying that you’ll “figure it out later” or waiting to apply on a different screen. Things come and go so quickly that you need to strike when the iron is hot.

    One historical example is the quasi-famous Aspire link. Way back when (somewhere around 2018-2019 I believe) somebody managed to get their hands on a link for the Hilton Aspire card without the annual fee. That card is already one one of the few cards that makes sense for many of us to keep even with the fee, so getting an uncapped FNC, Diamond status, and a handful of useful credits for free was quite the coup.

    As you’d imagine, that link didn’t last very long, and all the people wringing their hands over whether they were going to get in trouble or if the link was legit ended up empty handed. 

    To add insult to injury, many people had years of not being charged the annual fee via that link. Again, not a home run play. But it was one free night a year at the Waldorf in the Maldives and (at the time) $250 to spend there – aka enough for the famous cheeseburger. 

    However, there are some other instances where the play is a home run and hesitating on it is seriously detrimental to your bottom line. I can think of a very recent instance where the window to take advantage of the play’s full value was short (and is now closed). In addition, one extremely easy way to meet the requirements amidst a dearth of other options died the same week. 

    Back in that Aspire example, I hesitated and only got the zero fee Aspire on P2’s account (“sorry babe, you’re Amex shutdown now”), which was a mistake. But learning from that mistake led to me not hesitating on a myriad of other plays, many of which were markedly more exciting than a Maldivian cheeseburger.  

    The usual disclaimers apply – assess your own risk tolerance, go at your own pace, etc. etc. But if you can clearly understand the value proposition when something new inevitably pops up and you’re stuck on a company all hands, consider taking the initiative right away. Never put off until tomorrow what you can do today, at least if it involves churning. Good luck hitting those unicorns.

    Živjeli!


  • Folk advice part 2: Don’t think twice, it’s alright

    Folk advice part 2: Don’t think twice, it’s alright

    Companion Song: Don’t Think Twice, It’s Alright – Bob Dylan

    Time for part 2 of churning and MS advice pulled from folk music. In part one, I posited that diversifying your lineup of plays and not overlooking opportunities with limited profit ceilings was both a good way to scale up, but also a way to hedge against shutdowns. This time, I’m going to talk more about what to do in the latter situation.

    A limited profit ceiling generally means tight caps. That could be something like the Chase Freedom capping quarterly 5x at $1500, but that isn’t a good example for my thesis. That (extremely) tight cap is the reason a mainstream fee free card with valuable transfer partners has 5x categories in the first place. 

    Other times, tight caps are instituted by a fintech or smaller bank that is at least peripherally aware of rewards arbitrage and wants to nip that in the bud. While those caps stop them from hemorrhaging bonus and/or interchange payouts, it doesn’t stop savvy customers from getting some level of value out of them.

    Nobody ever gets shutdown by Chase for maxing the Freedom cap, for a couple of reasons. The first is that $300/year is peanuts. But the second is that I’d imagine there was some level of financial modeling performed down at 270 Park Ave that determined the caps placed on certain cards were within acceptable risk and they were ok with a certain percentage of advantage players maximizing the cap. 

    You know who probably doesn’t have the ability to do this (besides Citi)? A lot of the platforms that fit the mold of a play I described in the first installment. They’ll have limits in place, but they aren’t quite as scientific as a big bank like Chase could do (and they may be a direct reaction to an uncapped launch). 

    Chase might be fine paying out on $6k/yr of Freedom spend or $25k/yr of CIC spend, because it’s a beyond miniscule part of their P&L. For your average series B fintech, paying interchange fees or bonus points is a more important part of the overall equation.

    As a result, it’s not super hard to get shutdown even when you are playing fully within the rules. I encourage everyone to be ok with this outcome – you aren’t a profitable customer by any stretch of the imagination, so why would they want to retain you? It’s not like you’re suddenly going to start carrying a bunch of debt or using their pointless debit for everyday purchases. 

    Talking about it theoretically is nice, but I always find it easier to illustrate with a real-world, recent example. A relatively large group of the community got axed by a fintech in the last week or so, even though they had fairly strict limits. This fintech wasn’t actually special, but it was one of a few somewhat well-known cogs in a much more well-known loop. 

    Since this is 2025, I sympathize with those that are upset about losing something easy. But I’ve seen way too much thought and time devoted to these shutdowns and what the next step is. For 99% of us, the profit ceiling was somewhere between $300-$420/mo. I’m not minimizing that amount, especially since the hourly return on the time it took was fantastic. But ultimately, it’s not the home run play that is going to buy that orange Evora. 

    The whole reason I advocated for finding and understanding as many $300-$500/mo plays as you can in the previous post is to reduce your exposure to a play dying – and to be able to shrug and say “oh well” when it does, because you have eggs in other baskets. 

    Losing this one is a mild bummer. But that’s really all the brainpower you need to spend on it – it’s not exactly surprising that a company doesn’t want a bunch of users that load money in with a payment method they lose money on, and get the money out in a way they also don’t earn on, regardless of if it was within their limits. Ironically, we were the exact opposite of the customer persona they’re targeting. 

    Onwards and upwards, my friends.

    Cảm ơn!


  • Folk advice part 1: One trick ponies

    Folk advice part 1: One trick ponies

    Companion song: One Trick Ponies – Kurt Vile

    When I’m working at my 9-5 or couch MSing, I usually listen to high-tempo music like early phonk or the seminal metalcore album Jane Doe as the perfect background to focus. 

    As a result of losing plays over the last few weeks, I’ve spent way more time driving around town returning to the ‘ol street MS grind. But hardcore screaming isn’t exactly the perfect soundtrack for a monotonous road trip, so I’ve been listening to some old folk-adjacent favorites. 

    In revisiting some of those songs, there were some lyrical themes that are good advice for the state of the hobby right now – here’s part one of a three part series.  

    For a long time in MS, being a one trick pony was more than enough. Plays lasted so long and networks of information were so disparate that you could find your golden goose and be all set. Whether you’re talking about old school stuff that lasted for years or the new(er) school plays that have died this year, it was possible to sustain a healthy margin on one play alone. 

    For many, there wasn’t a compelling reason to learn the quirks and nuances of a new system, platform, or bank. Why bother when it was just taking attention away from the play you know like the back of your hand? I don’t think I need to write a paragraph explaining why we need to bother now, as frustrating as that may be.

    Over the last couple of years, a lot of us got complacent because of how easy it was. A big part of the MS world was content to have the MS equivalent of an “email job” (not that I blame anyone for that). 

    A small population saw the writing on the wall, rolled up their sleeves, and laid the groundwork for the MS equivalent of a blue collar job. That group is much less concerned about any of the shutdowns going on now, because they weren’t shutdown in the first place.

    I’m feeling some of this pain myself because of an unrelated shutdown, hence the rolling around listening to Kurt Vile. It has been years since I spent a day awkwardly staring at the back wall of the Staples register as the cashier passive-aggressively fumbles with the security tape of fee-free gift cards. But much like a FIREd person taking a job as a barista for human interaction, it feels strangely good.

    I’m a huge proponent of streamlining your time spent on MS lest it shift from a highly profitable hobby to a low-wage full time job. But in the spirit of continuous education and staying curious, paying more attention to signal you’re seeing out there is going to become more and more important.  

    MS home runs are going to get harder and harder to hit going forward as things like uncapped bonus categories and unlimited debit pay go largely the way of the dinosaurs. This does not mean there aren’t still valuable opportunities. While a lot of these plays will cap out in the $500-$1000/mo range, when you add multiple plays and players, they add up fast.

    So next time you see someone extolling the virtues of the latest vowel-less fintech, take a few minutes to evaluate and understand the possible value. Chances are it’s something you can spend a maximum of 5-10 minutes a week on. AKA, the average amount of time it takes to spend $1,800 at a Staples. 

    เชียร์!


  • Friday crossword hijinks

    Friday crossword hijinks

    It was yet another tough week in churningland, punctuated by (fairly inconsequential in the grand scheme of things) fintech shutdowns and some ominous A/B testing.

    Instead of worrying about things we can’t control, let’s start the weekend early with another churning and MS mini crossword. I’m linking out again because embedding it directly starts the timer as soon as you open this post or email and that’s just not fair.

    Good luck with the crossword, let me know how fast you complete it, and have a good weekend.

    Manuia!


  • Playing devil’s advocate: speculative transfer edition

    Playing devil’s advocate: speculative transfer edition

    Throughout each year, there is a (somewhat) predictable flow of transfer bonuses from both banks and loyalty programs enticing you to move your flexible and somewhat liquid bank points to rigid and somewhat less liquid program-specific points. 

    The value proposition is often compelling – reducing an already appealing saver award rate by up to 30-40% is the kind of cents per point fodder that the affiliate blogs love to share en masse. However, unless you get extra lucky, a transfer bonus won’t line up with a booking window for upcoming plans.

    So, what is one to do when an award program you’re fond of is offering a bonus when you have no immediate need to book? The general wisdom is to completely ignore the bonus – after all, “don’t speculatively transfer” is an axiom that is probably only a few pegs below “don’t call the bank” in churning lore.

    For most churners, this logic is sound. However, I’ll offer the contrarian opinion that there are a handful of reasons to speculatively transfer when you’re hitting plays hard and aren’t relying on sign up bonuses as your main source of points and miles. 

    A psychological push

    I’ve written about why I think MSers should treat themselves occasionally and a speculative transfer during a bonus period is the perfect opportunity to do so. Over time and experience gained, the average “rainy day fund” of points for a MSer will grow smaller and smaller. Once you start to see points as an asset with a market value tied to them, it’s less than ideal to have them sitting around earning nothing.

    The team cashback people can probably ignore this advice, but I believe there’s something to be said for keeping a (relatively) small stash of points in your favorite loyalty program as a form of withholding to remind you to do something fun with them. 

    It gets a bit more difficult psychologically as time goes on to redeem for flights (especially in premium cabins) when you can no longer pretend it’s free and can assign an accurate opportunity cost on the redemption. It’s a bit easier if the points are already locked into a program, especially if said program frowns on third party bookings. 

    Ironically, flexibility

    As we all know, churning and award travel are no longer niche hobbies confined to FlyerTalk forum posts. While I know we all have a good laugh at the NYT comment section whenever they post an article about churning, there will always be a handful of people who read that article the same week they see an “influencer” posting a TikTok about ANA F and put two and two together.

    To support this growing demand for “free” travel, a cottage industry of tools has popped up to make finding an ideal award flight easier than ever. Between search tools that make ExpertFlyer look like COBOL in comparison and an array of monitoring services that are constantly looking for big award drops, it’s never been easier (or more competitive) to book a bucket list flight.

    And just in case Trey, Tiffany, Jared or anyone else in said industry is reading this – I’m not hating at all (and I pay for a bunch of them). That being said, this new landscape necessitates being ready to book something in hours (if not minutes), compared to the relative lifetime you had back when ExpertFlyer was the primary game in town. Having miles in a loyalty program removes at worst a few minutes of processing time, and at best a glitch or error that kills your chances of getting the space completely. 

    A unicorn like JAL releasing multiple F seats a few months ago doesn’t last long – if I hadn’t already speculatively transferred Avios during transfer bonuses, I’m not sure I would have succeeded at booking it. Having your “rainy day fund” in a loyalty program allows you to jump on a bucket list flight as soon as the Thrifty Traveler alert hits.

    A hedge against adverse action

    It’s probably fair to accuse me of burying the lede in this post because this last reason is much more tangible than the first two and is likely the most relevant for this audience. It’s possible to get largely neutered from earning points in a given program if you’re shutdown by that program’s issuing partner. Is this the end of the world? Probably not, but it can hurt, especially if you live in certain geographic areas. 

    For example – let’s say you accidentally had a couple of returned payments with Amex, and they decided to shut you down. That would be quite tricky if you were a Delta loyalist – you’d no longer be able to transfer Membership Rewards to Delta, and you’d lose the ability to earn on the Delta co-branded cards as well. Delta isn’t always the easiest to book on partners, either. What are you going to do – actually pay for flights to earn miles? Come on now. I sure hope you don’t live in Atlanta or Minneapolis.

    If you’re into shenanigans and hijinks on a certain bank and they are the issuing partner or a transfer partner (or both) of a loyalty program that is valuable to you, consider preemptively transferring, especially during a bonus period. Getting shutdown sucks, but it sucks a little less when not all is lost. 

    Frequent Miler has a helpful database of transfer bonuses – take a look every once in awhile and see if there is a match between a bank you may be on borrowed time with and a loyalty program that you like using. 

    Anyway, that’s my spiel for today. It’s probably an unpopular opinion, but I think it’s a minor behavioral adjustment that can pay dividends. Whether that means booking a unicorn first class flight or just saying “f it” to a long weekend to cross another ballpark of your list, having that extra 20-40% helps. Happy travels, and good luck with the shutdowns.

    Առողջություն!


Sign up to be notified about new posts

Your email address will not be sold and will only be used to send you notifications about new blog posts – read our privacy policy for more info.

Archives