The American Express Platinum and Business Platinum cards (side note: Am I supposed to ™/® those 14 times? everyone else does) famously have $200™ annual incidental airline credits®. There’s no trophy for being the first data point on what works for gaming the credits, so often waiting a few weeks to learn what works is the right play. As an aside, here’s what that looks like in 2025:
United: Buy TravelBank credit directly. It expires in five years and can be used to pay for United flights. You can usually sell this for 85%+ too, and with a little trickery you can turn them into flexible credits good for other people and on other airlines [more info]
Delta: Buy airfare and pay partially with a gift card or travel credit, pay for the remainder with your card (don’t go over the incidental credit amount though). Alternatively if you have a co-branded American Express Delta card and are eligible for Pay with Miles™, pay partially with miles and the remainder will be credited™ [more info]
Alaska: Buy a seat upgrade after booking (*cough* but call it a seat selection fee®) or buy a flight paid partially with Alaska wallet funds and partially with your AmEx (less than $100), then refund to your wallet after 24 hours [more info]
Southwest: Buy a flight less than $109, or book an international flight with taxes under $109 per ticket, then refund to a travel credit. Combine with Wanna Get Away+ to get around name-locking [more info]
American: Buy cheap airfare, then change it to a flight that you really want that costs more and pay with your credit card (don’t go over the credit amount though). If you want to gamble, you’ve got roughly even odds that award taxes and fees will count [more info]
JetBlue: Buy a flight less than $137 then cancel the flight after 24 hours and refund to your JetBlue wallet. Side note, whomever figured out that $137+ wouldn’t work but < $137 would is my hero [more info]
Spirit: Buying a Big Front Seat upgrade works, and airfare below approximately $60 also works [more info]
We’ve buried the lede though, January is special with American Express because you can change your selected airline once online this month only, even if you’ve already received your incidental credit on a different airline. You’ve got five days left to do that, don’t dally!
EDITOR’S NOTE:Some of the smartest members of the community have stepped up with guest posts during the holiday break in 2024 and now on Saturdays in early 2025. Special thanks to today’s author mforch for reflections on the hobby. Have a nice weekend!
We are in a golden age of opportunity. We can gamble on the outcomes of a game, presidential election or digital money. New platforms pop up almost weekly, but the strategies that worked last year, last month, last week- don’t always work today. That’s the nature of the game designed to keep you chasing, not winning. But sometimes it isn’t about beating the game—it’s in learning to adapt, redefine, and turn what looks risky into the next big play.
Gambling to me isn’t about the game; it is The Game. Gambling has always been a tool. At the start, the game was simple: win. Win big, win often, and stay ahead of the curve and then hello millions (well, maybe more like thousands). But if you’ve been in the game long enough, you know that the rules change. Arbitrage opportunities disappear. Phone armies get found, fake mustaches no longer work and casinos no longer will taek us. The tricks that worked so well yesterday dry up overnight. But maybe, it’s not only about winning—it’s about not losing. It’s about figuring out a way to just be in the game where you have an edge. If you’re following me this far then high5! And while low margin plays may not sound sexy, that’s what built Vegas.
Here’s the dirty secret: casinos, loyalty programs, rewards schemes are all designed to encourage you to make sub optimal decisions. Maybe it’s redeeming points for gift cards or Amazon purchases, their game is praying on human nature to take the easy way out. But if you learn to harness some basic strategy—like leveraging venture capital to offset losses, using a credit card signup bonus to scale your points game, or simply figuring out how to play long enough without getting burned—you can flip the script.
This is where gambling and travel hacking converge. They’re both about understanding the system and finding leverage points. Sometimes, that means knowing how to lose strategically to set up a win. Sometimes, it’s as simple as knowing when the odds have flipped. Other times, it’s just 4x Entertainment. The tools may change, but the principles stay the same.
Knowing that their game is to take advantage of human nature, playing the long game is a superpower. Small edges can become large rewards over time with consistency. The people chasing flashy wins are the ones funding your business-class seats or your five-star hotel suite. And the people designing these systems know that 99.9% of people will never stop to think about how the game works. That’s what keeps the game going. But if you’re in the 0.1% of people who can adapt, scale, and stay ahead—you’re playing a different game entirely.
Ultimately, the goal isn’t just to win (well it kinda is). It’s to stay in the game long enough to see opportunities others miss. Long enough to realize that sometimes losing isn’t losing- fake money can be real money. As long as you’re still playing, you haven’t lost. What’s old is new again. Because here’s the thing: losing isn’t the opposite of winning.
Status is most useful for free checked bags, economy plus seating, and lounge access on international itineraries. In theory you can only match every five years, but also in theory: (1) communism works, and (2) the colors of gummy bears are evenly distributed. (Thanks to FM)
The Chase Marriott cards have increased sign up bonuses:
– Boundless: $150 statement credit + 100,000 Bonvoy points after $3,000 spend in three months, $99 annual fee – Bold: A free night certificate for up to 50,000 points plus 60,000 Bonvoy points after $2,000 spend in three months, no annual fee
They’ve also introduced Pay Yourself Back on the cards at a rate of 0.8 cents per point, which is more than the market value of a Bonvoy point so actually pretty good. The bad news though? You’re limited to $750 in total redemptions annually. But at $750 + $150, you could turn the Boundless into a $900 sign-up bonus and convert it to a Ritz Carlton card after a year (a move we call the reverse Bonvoy).
– Premier: 170,000 points after $4,000 spend in three months, $99 annual fee – Rewards: 100,000 points after $2,000 spend in three months, no annual fee
I prefer points offers to capped free-night certificates approximately 122% of the time, but not everyone thinks like I do.
40,000 points in the IHG program is good for average, mid-tier hotels, and if you stack the free night certificates with fourth night free, you can make this effectively a six night free sign-up bonus.
Qantas will devalue its points program on August 5, raising redemption costs between 5% and 20%. Redemption fees will increase too, because duh. (Yes, some short haul Qantas metal redemptions will decrease in cost; no, that doesn’t make it any better.)
No blackout dates are listed unless you’re traveling to Hawaii or Puerto Rico, then black out days are longer than an entire month.
Breeze Airways has 50% off of base fares with promo code GONOW for travel through May 22, sort of. They took a page from Southwest’s book and added a blackout periods of over an entire month, but decided it’d be funner to apply it to all destinations and not just non-continental US destinations.
– $50 back on $250+ at Grand Hyatt through April 15 – $250 back on $1,000+ at Marriott Homes & Villas through April 13 – $150 back on $750+ at Hiltons in Mexico, the Caribbean, and Latin America through March 31 – $30 back on $150+ at Turo
There are games everywhere with these, starting with being able to use a single offer multiple times by thinking differently about saving offers. (Thanks to Tom)
In case you’re not seeing the heightened referral, there are also two modified, unintentional links for the same offer with no-lifetime language (NLL). There’s (probably minimal) risk in using modified links that American Express didn’t build, so do your own risk / value judgement. The first link is here, and the second is here. (Thanks to DDG)
More helpful notes for people that think differently.
There are questions that need a different answer though, so let me present today’s phrase: “My boss makes me”
Examples:
Q: Why do you want to split this large gas transaction into two weird payment amounts? A: My boss makes me
Q: Why do you need 18 different email addresses? A: My boss makes me
Q: Why do you want to expedite this request? A: My boss makes me
Q: why are you using four different loyalty accounts? A: My boss makes me
Q: Why do you want to apply the upgrade after booking instead of at booking? A: My boss makes me
Q: Why are you flying from IAH-LAX via JAX and IAD? A: My boss makes me
Q: Why don’t you just drop that box in our self-service drop over there? A: (While carrying a box full of $28,000 in gold) My boss makes me hand it to a person
Q: Why do you waste time reading MEAB? A: My boss makes me
Have a nice Tuesday!
Why are you wearing denim on denim? My boss made me.
– +7x on gas, grocery, and dining (IHG) – +5x on gas, grocery, and dining (Hyatt, Aeroplan, United, Southwest, and Marriott co-brands) – +2%-5% bonus cash back for physical card transactions (Instacart) – +5% back on gas, grocery, and dining (Amazon)
The caps on these are historically $1,500 in spend, but this round it’s been reduced to $1,000. If you get an error while checking, open an incognito browser tab.
Do this now: Check for your targeted United Mile Play bonus offer. I wasn’t targeted this round, but there are offers as high as 40,000-50,000 miles for things like taking three trips of $500+ or flying in a premium seat four times.
EDITOR’S NOTE:Some of the smartest members of the community have stepped up with guest posts during the holiday break in 2024 and now on Saturdays in early 2025. Special thanks to today’s author, Graham from TC Tailwind, for his enumeration of failures in the hobby. Have a nice weekend!
Introduction
We are, almost as a rule, optimizers in this hobby. Optimizing is supposed to pay off (for some definition of “pay off”), but it doesn’t always. I’ve failed in a lot of interesting ways when optimizing, and I console myself in those failures by telling myself I’ve learned something from them. For your benefit –or at least entertainment– I’ll enumerate some of my failures, and the tactics that I’ve developed to avoid repeating them.
My Failures
Taking on more complexity than I could understand
As a Canadian student earning internship money in the US, I had a brilliant idea to stash that money in a TFSA (the Canadian equivalent of a Roth IRA). I was planning to (and did) return to the US to work full time, and I knew the US didn’t respect the tax free nature of TFSAs. But I was also smart, and knew that the US doesn’t charge you tax on your investments if you don’t sell them, so I figured I could safely stash the money there tax free until I returned to Canada eventually.
It turns out I wasn’t smart enough. I did not know that the US has a special designation for money you invest in passive investments outside the country, and that it applied to Canadian ETFs. Nor did I know that they had an extra special tax treatment for them. I also didn’t know they had a handy little 4 page form that you have to fill out per ETF you own, and which no tax software I know of supports. In the end, this little stunt saved me nothing, and cost two rounds for foreign exchange fees on the money, and burned through countless hours of my time across multiple years of tax filings.
My tactic to avoid repeating this failure is:
If you have a clever idea, validate it with some experts first: I could have saved a ton of pain if I’d talked to an accountant. The churning world doesn’t have certified professionals you can go to, and it isn’t exactly known for its openness, but I’ve always found folks in the chat groups I’m in to be willing to call bullshit on a bad plan. Turns out people like correcting you when you’re wrong on the internet, who knew?
Consider the opportunity cost of your plan: Any time you undertake an optimization, think whether it precludes you from doing something else (especially if that’s something else you’d normally be doing, like I would have been in this case). Calculate the value of the alternative, and make sure it’s less than the value of your plan.
Being too early
I’ve always been the type of person to try and get things done early, and boy have I found a million ways in which that can burn you. Closing a credit card with lounge access? Of course I end up with a last minute flight and no other lounge options in that airport. Burning my Dell credits on something frivolous on Jan 1? Of course I end up needing a new router that I could have gotten for free with those credits. In each case, my desire to get things done early meant I gave up optionality that I could have used later.
My tactic to avoid repeating this failure is:
Wait until the last minute, if there’s no benefit to being early and little risk of losing the opportunity: Credit cards have well known annual fee refund rules. If a bank will refund your money 30 days after the fee posts, there’s no benefit to cancelling it the day the fee posts. Set a reminder for a few days before tha last possible day instead. Similarly, if you have an annual benefit you’re clearly entitled to, there’s no reason to blow it early on something you don’t want at the beginning of the year, when you might want it for something else later in the year.
There are some huge caveats here. If something is too good to be true and might get nerfed, or it is less than above-board that might get patched, you should absolutely continue to get on that ASAP.
I love Doctor of Credit, and I was hooked on getting their deal alerts after I got a free phone out of one. But one day, I caught myself responding to one of those alerts by spending 10 minutes punching my personal information into a random website to get a free cookie dough bar. In retrospect, I view saving a dollar or two on a thing I didn’t even want as a failure (and it’s indicative of dozens of other micro-optimizations I’ve done, like the time I’ve wasted going through 1% back shopping portals on ~$20 purchases).
My tactics to avoid repeating this failure are:
Set a minimum dollar value on your time: I have a hard $200 / hour rule for my time now. Obviously I don’t spend every hour focused on making / saving money, but if I’m doing something to make / save money, it better meet that bar.
Remember free can still be too expensive: Just because something is free, doesn’t mean it’s worth taking. There are extra costs in terms of time, the environment, your health, etc., even on free items. If you don’t actually want it, don’t waste your time on it.
Not valuing my comfort
I recently flew home from Tanzania, and booked the cheapest business class ticket that I could using points. The problem? It involved an awkward 6 hour overnight stay at Cairo airport (a completely wonderful airport with no faults at all). Even finding a soft place to hole up in a lounge, I barely slept and I was a miserable traveller for the rest of my trip. In retrospect, not paying the extra ~50k points for a better flight was a failure to value my comfort appropriately.
My tactic to avoid repeating this failure is:
Set hard rules for your comfort: I can’t put a dollar value on comfort as easily as I can on time, so instead I make strict rules for myself. I already had a hard line that I don’t do red eyes in economy. Now I have a new rule that I don’t do overnights in an airport. These hard and fast rules help me feel mentally compelled to take the options that I know are better for me, even if they’re more expensive.
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