Category: Wisdom

If you search Perplexity for “What are American Airlines miles worth?”, you may get a range of numbers from 1.0 cents each to 2.5 cents each and a lot of hallucinated reasoning behind those numbers too. If you repeat the search, you’ll probably get a different result. Valuing miles is hard, even for AI. So, often we revert to one of the hobby’s normal methods:

  • A mile is worth the value of selling it on the grey market
  • A mileage redemption is worth the cash that you would have paid without the miles
  • A mileage redemption is worth the cash price that the ticket or property is listed for
  • A mile is worth 1.0 cents, because most programs let you redeem at that level
    A mile is worth your opportunity cost for acquiring it

Those are all fine and good, but sometimes you need a legally defensible valuation for a mile as part of a settlement, tax action, corporate valuation, or similar rigorous process, and the above answers typically won’t cut it because of logical holes big enough to fly an A380 through. Also, judges in particular hate it when you’ve got a hand-waivey answer with variability left up to the eye of the beholder. So, let’s reintroduce a mileage valuation that’s easily defensible:

  • A mile is worth what the program will sell it to you for

Right now, I can buy 10,000 AA miles for $338.63, so for the purposes of a legally defensible valuation for miles, AA miles are worth 3.3863 cents each.

Happy Wednesday!

Yes, there’s another common way to determine mileage value.

An often overlooked technique for dealing with sludge in churning is sending a Certified Letter via USPS. Since the friction of sending one involves typing something, printing something, stuffing something, licking something, driving to something, paying for something, and then waiting days for something, it doesn’t happen very often.

But when a company gets a Certified Letter, you’ve effectively guaranteed that a human with some decision making power will read it and decide what do do about it because Certified Letters are often precursors to lawsuits, and it turns out companies don’t like lawsuits (probably because they don’t fit as nicely as tailored suits.)

Certified Letters have helped me after customer service failed repeatedly, in just the last year, they’ve helped me fix:

  • Credit card disputes
  • Credit report disputes
  • Locked gift cards
  • Missing bank bonuses

Remember, the value of fixing something is often worth the value of a good churn.

Happy Thursday!

More stuffing, because apparently people want shirts like this?

The CFPB is effectively non-existent 🪦, which means that when a bank holds your money and shouldn’t, doesn’t award a bonus when they should, changes credit card terms in an illegal manner, or sends all of your personal details to an adult website owner, you don’t have an easy, central resource for fixing it. You still have tools at your disposal to help though (ordered by of likely ease of use):

  • Your state banking regulator and charter administration
  • The BBB
  • Your state banking commission
  • The FDIC for banks or the NCUA for credit unions
  • State small claims court
  • The OCC (ya down with OCC? yeah you know me!)
  • FTC
  • Arbitration (most banks have these clauses in their paperwork, and they’re almost always obligated to pay for the arbitration too)

Don’t shy away from the arbitration option when the numbers get into five digits, if the bank obviously behaved incorrectly your odds are probably great.

Happy Wednesday!

OCC’s current official coffee mug.

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.

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.

We once discussed how “budgeting” is a magic phrase in our hobby because it’s a simple response to many financial questions that doesn’t illicit any follow up.

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.

Yesterday’s Change

Yesterday, AirFrance and KLM’s FlyingBlue program devalued its low level awards (again). Long haul prices on KLM or AirFrance:

  • Economy: 25,000 miles each way, up from 20,000 miles
  • Premium economy: 40,000 miles each way, up from 35,000 miles
  • Business: 60,000 miles each way, up from 50,000 miles
  • La Premiere: 165,000 miles each way, up from 150,000 miles

Partner award prices went up somewhat too. The change was intentional, and in theory will also bring increased award availability on first party metal.

Devaluations Will Happen

Unfortunately, devaluations will continue over time in all programs because:

  • Inflation in consumer prices means more points earned for buying the same things with a credit card
  • Inflation in hotel and airfare prices means more points are awarded for revenue bookings
  • For airlines, CASM inflates over time, and providing an award seat costs more over time
  • For hotels, CPOR inflates over time, so providing free nights costs more over time
  • Decreasing the value of issued points lowers liabilities on a company’s balance sheet

The only way devaluations won’t happen is with regulation, but (a) that’s unlikely to come, and (b) would just cause a different type of devaluation, such as no award space released.

Protecting Yourself

To effectively shield yourself from devaluations to the extent that such a thing is possible:

  • Book awards as early as possible: Points on average are worth more now than they will be in the future, so lock in current pricing when you can
  • Book speculative awards with spare points: As long as a program offers free cancelations, you can lock in current pricing and cancel if the trip won’t work out (or if a lower price comes along)
  • Don’t save more points than you can reasonably burn in the next n months: Saving points that will decrease in value probably isn’t fiscally sound, just like eating a tub of lard probably isn’t nutritionally sound. Ok, but what value should you use for n? It’s hard to say, but I think the half-life of devaluations is around 24 months with some medium variance
  • (A corollary to the prior item) Cash out excess points, especially those you can’t burn in the next n months: Cashed out points turn into cash, which: earns interest, can be invested, and can be used to buy more miles if you cashed out too many. It turns out, money is fungible

Good luck out there!

Next time on Tuesday Wisdom: Elmo’s airplane explains RASM.