Author: matt

Let’s discuss a fictitious small town, Lubbockito USA, and use it to illustrate a point:

There are six restaurants in Lubbockito:

  • Subway
  • SideShowSubs #233
  • McDonalds
  • Burger King
  • Carls Jr
  • Rob’s Special Burger

Let’s say you’re a restauranteur and want to bring Lubbockito a new option, hoping to cash in on the Lubbockitizen’s wallet share. There are two right answers for what new restaurant to open:

  1. A sub or a burger joint, because that’s obviously working and people seem to like those
  2. Anything other than a sub or burger joint, because that “obviously working” market is well done

In churning, there are parallels for credit cards, bank accounts, bonuses, loyalty programs, and plenty more. If you find yourself uninspired with the Chase Banks, Walmarts, Wells Fargos, and Hyatts of your world, take a look at the options that you aren’t hitting. There’s plenty there.

Happy Monday!

Did you know? Rob’s serves hotdog shaped cheeseburgers in Lubbockito.

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 who needs no introduction for following up on the Early Warning Service warning (under duress). Have a nice weekend!

Everyone loved my Early Warning System (EWS) post last year, and by everyone I mean at least 2-3 people, so Matt asked me to post a bit more on the topic. I said no, but he threatened that he’d force me to load more money into Juno if I didn’t so here comes my update.

Image of the conversation of MEAB threatening me

You’re thinking to yourself “SideShowBob233 what else do you have to add here” (and this time you didn’t say the 33 out loud but kind of trailed off like someone who just got his Pepper account locked by buying too much Best Buy). Well, I will tell you. In the most rambling way possible.

I advised everyone to use a business account if at all possible, but it turns out not all business accounts are excluded from EWS reporting. Several victims reached out to me to let me know that BOA biz checking for sole proprietors does report to EWS. I don’t know if that applies to all sole proprietors or only some (I don’t have a sole proprietor account at BOA because the voices told me not to). It’s possible that other banks also report biz checking for sole proprietors, feel free to reach out on Telegram, WhatsApp, passenger pigeon, or via telepathy to send me your DPs.

But Bob you’re saying (maybe you’re getting a little too familiar with me considering we only met once and that was in a dream, albeit one where there were no clothes) why should I care if all my transfers are tracked by EWS? Who really cares? Well I’ll tell you who cares. Your mom. Also bank compliance officers (which may or may not include your mom, I haven’t tracked her career since we broke up) who when they get nervous about shenanigans we just pulled will then grab your EWS report to try and get more info on you. If they can’t find much information they may still shut you down, but if they get a 500 page report showing tons of money going everywhere you can bet they will be shutting you down faster than you can yell for your mommy.

To summarize, don’t step on a rake, instead use a business checking that does not report to EWS.

– SideShowBob233

Your punishment for not listening to me last year.

  1. American Express has a targeted link for 20,000 bonus points for turning on Pay Over Time. After enrolling, set a reminder in your phone to turn it back off in 121 days to be ready for the next round.

    If you get the bonus offer on multiple charge cards, consider activating them in separate tabs as close together as possible because reasons.
  2. The Chase United Business cards have increased bonuses:

    – Business: 100,000 points after $5,000 spend in three months
    – Club Business: 75,000 points + 1,000 PQP after $5,000 spend in three months

    I’d choose an Ink Preferred card over these unless you’re chasing status or want United Club access, because where else can you get unlimited cheap cheese cubes under a sneeze guard?
  3. Wyndham has a points sale running through February 16 for 0.8125 cents per point after bonus. You’re still unfortunately limited to buying 100,000 points per calendar year on these, but if you have the right booking it can be effectively 50%+ off of the cash rate, especially with hidden value in the Vacasa program. (Thanks to lenin1991)
  4. American Express offers has an offer for $150 off of $1,000+ at Emirates through April 30. In theory, the flights have to originate in the US too.

    Yes gamers gonna game, but Emirates First award fees for US originating flights tend to be slightly over $1,000 so luxers gonna luxe too.
  5. Pepper had sales for gift cards yesterday with 25x at Southwest, 22x at Delta, 22x at Sam’s Club or Walmart, 18x at Home Depot, and 20x at Amazon.

    If you’re not already neck deep in the Pepper in the game I think now is a terrible time to jump in, but if you want to take advantage of those deals at small scale, I’d suggest reaching out to the other churners in the community to buy some inventory at a couple of percentage points above those rates. You’ll probably find plenty of sellers and won’t need to worry about Pepper risk.

Have a nice weekend!

More luxing it up, shut-in weekend style.

Last minute update: The AA5342 collision with a helicopter hits hard, condolences to all and forgive today’s jovial tone, it was written before the accident.

  1. Do this now: Register for IHG’s Q1 targeted promotion for a bonus elite night for all nights stayed, up to 10 bonus elite nights through April 28. If the site asks, the promotion code is 63666.
  2. Do this now: Register for Best Western Q1 promotion for 2,000 bonus points per night, up to a total of 20,000 points through May 11.
  3. Kroger has a promotion for 4x fuel points on third party gift cards and fixed value Visa and Mastercard gift cards excluding Amazon on Friday only.

    Thanks to Pepper, the brands that work for a reseller are largely limited to BestBuy and Lululemon.
  4. Rakuten in-store’s card linked program has two new promotions:

    – 1% bonus or 1x Membership Rewards at Food Lion stores
    – 1% bonus or 1x Membership Rewards at Stop & Stop stores

    Both are good through March 31, both require re-adding the offer an hour after its first use to continue using, and both have a bonus cap of $10 or 1,000 Membership Rewards per transaction. Fortunately, we’ve developed the technology to run transactions back-to-back though.

Happy Thursday!

What is this, and is it good? I’m not sure, but it’s slightly more interesting than the new JetBlue card.

  1. Do this now: Register for Marriott’s Q1 promotion for 1,000 bonus points and a bonus elite night credit for every paid night stayed between February 11 and April 28.
  2. Do this now: Register for Accor ALL’s promotion for 4x points earning on all 2+ night stays booked by March 16 and completed by July 13. Edit: this is only “new” hotels, not all hotels.
  3. Delta has an award ticket sale for round-trip flights booked by Friday for travel through the end of the year the, as long as the first flight happens by March 31. Rough pricing:

    – East coast to Europe in economy: 36,000-45,000 miles round-trip
    – West coast to Europe in economy: 50,000-65,000 miles round-trip
    – East coast to Europe in business: 220,000 miles round-trip
    – West coast to Europe in business: 290,000 miles round-trip

    Delta cut its daytime flights to Europe last fall which is the only way I’d do this in from the west coast in economy, but I could probably be talked into it from the east coast if I had imbibed a bit too much.
  4. Frequent Miler notes that Alaska MileagePlan Shopping awards elite qualifying miles on both regular spend and on portal bonuses, so prepare for a swole rank of 100k MVPs in 2026.

Coming soon: Alaska gate when MVP Group A boarding is called.

  1. Simon Malls will stop selling gift cards in-store on Friday. The glory days of Simon gift cards have passed, but because we like to study the past to learn for the future, there was a time when:

    – They carried $1,000 GCs in-store
    – Some malls coded as restaurants with some issuers
    – The cards could be easily liquidated at Safeway, Kroger, or Walmart

    None of those things are true any more.
  2. Regarding the elephant in the room: I think Pepper manufactured spenders are largely informed about the current risks involved with the platform. If and when it fails, I think the probable outcome is:

    – Gift cards issued more than a week prior are probably safe
    – Gift cards issued in the last days of the platform may be zeroed by BlackHawk
    – Floated coins will be lost

    Why bring this up today? Yesterday Pepper offered effectively unlimited quantities of Amazon gift cards at 22% cash back. Most of that 22% won’t post for a few weeks. So, I guess I’m reading the room which I’m good at about 50% of the time. I still have floated coins with Pepper, but I’ve been scaling way back. I actively chose not to buy yesterday.
  3. In a move surprising only the ghost of Spiro Agnew, Marriott devalued its award chart for higher end properties. A few notes:

    – High end property redemptions increased by as much as 80%
    – Don’t trust a blogger’s valuation of points, use your own redemptions as a guide
    – My valuation of Marriott points was already low at ~ 0.5 cents each, this doesn’t help

    New valuation? Still 0.5 cents, but a low 0.5 cents.
  4. Bilt’s rent day promotion for Saturday is a 20%-100% transfer bonus to Avianca LifeMiles, depending on your status in the program. You’ve still got time to earn points that’ll post by Saturday. I’m certain there’s going to be a limit on the bonus, but I can’t find it published and I’m of course not part of Bilt’s marketing campaigns because reasons.

    Avianca has strange loopholes that lead to great redemptions, but availability often isn’t great.
  5. Staples stores have $200 fee-free Mastercards in store through Saturday, limit nine per transaction.

    These are Pathward gift cards.

More Bonvoy math.

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!

Happy Monday!™

Adventures in learning how to bury the lede.

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.

– @mforch

More lessons on opposites.