Category: Wisdom

EDITOR’S NOTE: I’m on an annual blogging vacation for the last two weeks of the year. To make sure you still have content, some of the smartest members of the community have stepped up with guest posts in my absence. Special thanks to today’s author, a churning-FIRE sage and podcaster extraordinaire, Kai from The Daily Churn Podcast, for writing this post while I’m on vacation. I’ll see you on January 1!

As the new year approaches and things slow down for the holidays, I’ve been reflecting a bit on the blessing and curse of being an optimizer. I think many of us, particularly churners, love to optimize. We optimize our travel, our miles earned, our points burned, for first class flights, five star hotels, and cashback at almost zero cost. What’s not to love?

Society also loves optimizers. Improve efficiency, get promoted. Launch a startup, get rich. Work smarter. Hustle harder. Eat healthier, live longer. Hack your workout, your morning routine, your relationship, your life.

Nothing builds a habit faster than an activity that produces tangible results. Encounter problem. Find optimal solution. Release dopamine. Rinse, repeat.

Do anything a thousand times, and it’s no longer an activity you do. It’s a part of who you are. There are worse things to be than being an optimizer. In fact, family and friends probably love your optimizing. You help them optimize their vacations, their finances, their diet. It feels good to help others.

Your partner, roommate, or cat might be the only one who sees the other side of the coin.

They see you spend three hours researching the best pillow for stomach sleepers, cross-referencing amazon reviews with Wirecutter recommendations, checking slickdeals and camelcamelcamel for historical lowest prices, cashbackmonitor for the highest portal rates, cardpointers for active credit card offers, retailmenot for coupon codes.

They see you spend days on the phone chatting with customer service to figure out the ins and outs of their award booking system, so you can secure first class tickets for you and your friends.

They see you spend weeks working on a bot to automate thousands of micro-transactions to take advantage of interchange arbitrage opportunities on a few niche fintech platforms (only to see it die before you could really scale it up, sadface).

They also see that year by year, despite everything in your life becoming more optimal, you still spend just as much (often more) time optimizing.

That is the optimizer’s curse.

There are an infinite number of things to optimize. There is no end. After all, stopping short of optimizing everything would be, well, sub-optimal.

Optimizers trend towards maximization. I mean, what kind of wildebeest would you have to be to quit halfway, to buy a pillow before reading the negative reviews, to manually perform a thousand micro-transactions, to leave award availability to pure chance?

But more and more, I see the value in satisficing. The idea of being satisfied with good enough. The middle ground between doing nothing and optimizing everything.

If you’ve ever had to suffer through corporate indoctrination (or took biology), there’s a principle you may be familiar with. It’s the Pareto Principle – 20% of the work often yields 80% of the results. Viewed another way – you spend 80% of your time squeezing out the last 20% of the juice.

My inner optimizer hates this rule. But there is no denying its truth. If I had just blindly bought the best pillow recommended by Wirecutter, it would have taken me ten minutes tops. I would have been perfectly satisfied. I would have saved myself almost three hours of research.

But in the moment, it felt good to maximally optimize all the way to 100. Optimizing puts me in flow state. Time slips away. One minute it’s morning and I’m at my desk sipping green tea. I blink and it’s the afternoon. I have four different browsers open, I’m thirty tabs deep into a reddit rabbithole, and I’m VPNing into Dallas for some reason.

And therein lies the true cost of being an optimizer. Lost time. Time you could have spent with family. With friends. Time you could have spent on your hobbies. On picking up a new hobby. Time spent hanging with your partner, your kids, your pets. Maybe time you could have spent finding a P2.

I’m the best at ignoring this cost. There’s so many ways to justify it. This is saving me money. This is making me money. We’re going on an amazing vacation. My partner loves nice hotels. I love flying first class. I’m helping a friend. I’m helping my parents. I don’t mind doing it. This is a buy-it-for-life [insert item].

Some days, my phone blows up not from texts or calls. But from reminders I set myself days, weeks, months, sometimes even years ago. Reminders for things I need to do to stay on top of my optimizations. Cards I need to cancel, offers I need to redeem, money I need to transfer, calls I need to make, deliveries I need to skip, subscriptions I need to pause, refunds I need to follow-up on, bonus deadlines I need to stay on top of, new opportunities I need to try.

Opening my Google Keep can feel like entering a warzone… duck, swipe, ignore, defer, reschedule for next week. Phew, made it out in one piece.

We optimize to improve our tomorrows, often at the cost of todays. How many vacations have you sat in your hot tub on the balcony of your top-floor oceanview suite, waves lapping at the beautiful beach below, laptop perched precariously on your knees to avoid water from the damn hot tub and glare from the damn sun, as you “quickly” check your email, scroll your blogs, post a pic of your suite to your group chat, while the latest episode of Huberman plays in the background?

Oh you’ve never done that? Cool cool, me neither.

There is always a tomorrow to optimize for. Until one day, there isn’t. You’ll lay on your deathbed, and if you’re lucky, be coherent enough to reflect on your life. Will that time you won 25 stars playing the starbucks game flash before your eyes? Or that free award flight to Lubbock? How about those pillows?

What will flash before your eyes? Maybe we could spend more time doing that.

So this holiday season, I’m advocating for being a little less optimal. To put in 20% of the effort for 80% of the results. To let go of opportunities that aren’t worth your time. To maximize less. To do less. To free yourself from your reminders, your calendar, your self-imposed mind palace of deadlines and commitments. To break the optimizer’s curse through satisficication. Satisfition. Satisfiction? Whatever, good enough.

– Kai from The Daily Churn

This dog is, uh, satisficed with the pillow.

EDITOR’S NOTE: I’m on an annual blogging vacation for the last two weeks of the year. To make sure you still have content, some of the smartest members of the community have stepped up with guest posts in my absence. Special thanks to today’s author, the always helpful and funny SideShowBob233, for writing this post while I’m on vacation. I’ll see you on January 1!

EWS, or Early Warning Systems LLC, is a credit reporting agency co-owned by some of our favorite banks: Bank of America, Truist, Capital One, JPMorgan Chase, PNC Bank, U.S. Bank and Wells Fargo.  I used to think of them as similar to ChexSystems (which anyone who’s been denied a bank account before knows and thoroughly loves in a non-platonic way) but they’re actually less similar to ChexSystems and more like a colonoscopy for your bank accounts, but without anesthesia (or a lollipop at the end).  You can request your consumer EWS report once a year using instructions here.  Once you send them the request they will email you within a few weeks, or tell you they will mail it to you.  It’s quite eye opening, I liken it to opening your trunk and finding 69,420 Airtags inside.  And remember after you request it what the late Tom Petty said (no not Here Comes My Girl – what is wrong with you anyway – the waiting is the hardest part).

Once the suspense has been lifted and EWS has deigned to give you your report the real fun begins.  You’ll get a nice report (164 pages in my case) full of every single freaking thing you’ve done in nearly every bank account you own (some bank accounts do not report to EWS thankfully, but most do).  You will see:

  • Every check written on every account
  • Every ACH transfer made (with destination shown for many of them)
  • Daily bank balances for a few months (and monthly for a few years) for some banks
  • Accounts you closed within the last 3-4 years
  • Accounts you opened in the last 3-4 years
  • Tears streaming down your face when you see how much info about you in tracked
  • In my case a rake between the eyes

In short, it’s an all you can eat buffet of tracking information for a bank that wants to see if you are a churner or not.  Or a money launderer.  Or if you have a strange sexual fetish that involves sending ACH transfers back and forth.   Regardless of the actual reason for the transfers, any bank looking at this kind of thing is not going to be happy.  Now some may shrug, some may open four new bank accounts without telling you (Wells Fargo is a co-owner after all) but some will see the kind of transfers a heavy MSer does and will kick you to the curb.   It’s not a coincidence that about a week before my shutdown letters from Chase arrived, they pulled my report twice.

Well that’s great SideShowBob233 you say (with the heavy emphasis on the “2” in “233” because you’re a bit psycho sometimes – don’t blame the messenger) but what the hell can I do about this? It’s not like you’re going back to your old second job waxing those wrestler’s backs – so is there any hope?   Yes, yes there is. 

You may note on your report that some bank accounts do not show up.  Your first step (after cleaning up the waxed back hair from the wrestlers – I can’t believe you left that on your floor since you quit 3 years ago and starting MSing) is noting all the accounts that DO NOT show on EWS.  Some credit unions do not report to EWS, but some do.  However zero business bank accounts showed on my report, and I’m willing to bet 69% of that back hair you just cleaned up that none will show on your report either.   So you want to move your transfers to business checking accounts whenever possible, as those will not be tracked.  Business checking accounts especially have an added advantage that banks generally do not care how you use them or how much money you run through them (not counting money orders – sooner or later those get noticed and you get shutdown). 

Don’t take my word for it – try it.  I’ve had several banks tell me that my transactions look like business activity and that I needed to stop it.  I’ve yet to have a bank tell me that for a business checking for example, although I like to imagine it going something like this:

Bank: SSB233, is that business activity we’re seeing in your business checking account?
SSB233: Why yes it is business activity

Bank: We’d like you to stop the business activity and move it to a business account
SSB233: But it is a business account

Bank: OK our bad, we’ll just charge you this $50 fee, make you come in branch for no reason,  and you’ll be good to go
SSB233: [steps on a rake]

So there you have it, EWS (which also owns Zelle – because who doesn’t want the people who managed to screw up money transfers so badly also holding all their bank data).  Thanks for listening to my rant, and if it doesn’t make sense to you I say go step on a rake. 

Pictured: SideShowBob233’s EWS report smacks him in the face.

EDITOR’S NOTE: I’m on an annual blogging vacation for the last two weeks of the year. To make sure you still have content, some of the smartest members of the community have stepped up with guest posts in my absence. Special thanks to today’s author, my original churning buddy and longest friend in hobby, Tyler, for writing this post while I’m on vacation. I’ll see you on January 1!

I’m not interesting. At least I don’t think. It wasn’t until Matt (MEAB) encouraged me to do a guest post that I realized I may be slightly more interesting than a layover in Lubbock. I asked “why me?” and he responded “you have a unique and interesting view on the world”. Coming from him, that is an amazing compliment. Although, Matt encourages us to read between the lines so perhaps that’s not a compliment. So I’ll share what I’ve learned this year. Just consider today’s blog post like going to a restaurant to get a Coke, yet they bring you an RC Cola. Just hang your head in shame and take it.

I took algebra twice, so I’m pretty good at math and I’ve calculated I pulled in over six figures from various MS activities this year (eight figures if I count the two numbers after the decimal point). It’s happened with effort, luck, stupidity, diligence, and tips from others.

I scaled hard this year. Matt told us “if you’re not getting shut down, you’re not pushing hard enough”. I learned this the fun way in a shutdown by a local credit union. I first was a bit frustrated, and even scared as I was grilled by the fraud team while they froze thousands of dollars. The financial proctology exam included every question except my blood type and my favorite karaoke song (that award goes to Gangsta’s Paradise – RIP Coolio). The CU shutdown turned out to be great, as it forced me to look at every CU in my state where I opened as many accounts as I could. I discovered one that allowed cc funding for new accounts/CDs. There are 5,000 credit unions in the US. Frankly, if you haven’t found one that allows CC funding on your own, you aren’t looking hard enough. And it’s not just credit unions. There are even banks that pay you to wire money in.

I better defined my goals, primarily shifting from points/status/miles to max profit. I travel less now, and I previously found myself racking up points and status for airlines I didn’t use. This year I sold a lot of points/status/gift cards on various markets and while it may not have a high cpp value had I used them myself, the mental aspect of having profit vs points was well worth it.

Diversification has been a core part of my investing strategy. This has been a catalyst for turning my miles earn and burn practice into profit earn and burn.  I had a goal to find one profitable activity from each of the MEAB slack channels, I read all channels from cradle to grave where I have been able to find a profitable activity in more than half – the others are there I just haven’t had time to get to them yet. If I just did one from each channel, that is 30+ different opportunities. And each channel as we know has multiple opportunities, even dozens.  Diversification is critical to not just churning, but to your own financial well-being. You need a job, stocks, retirement accounts, multiple small businesses, real estate, etc. For me, churning has turned into a similar thing – although I need to find a balance of being a jack of all trades, master of none and specializing in one thing. Having stocks, retirement accounts, businesses, real estate, multiple players has opened a ton of doors for activities to legitimize my practices.

This year I’ve probed and challenged conventional wisdom at retailers and discovered a few nuisances in my territory that paid off well. I even showed MEAB once how to get free Dominos. He tried it but was not impressed – apparently he has ‘standards’ when it comes to food… What a snob. I discovered even in my Kroger footprint there are different limits based on the technology of the registers in the same store. I’ve found this out with other chains and retailers too. Coupon codes maybe don’t have limits, or discovering you can create plenty of other accounts to score a deal, or promos that apply to things beyond the T&C. The sky can be the limit with some of these – but I gotta put in the time to try them.

As I go into next year and think about ‘what’s next’, I’ve learned spending is easy, liquidation is hard. Liquidation is my main struggle from payment processors, overzealous clerks, account freezes, and more. I’m frequently looking for liquidation channels to help scale so I plan to really invest in this area. I’ve been lucky to be able to float a bunch, though this is an area I need to invest more in. I think I’m going to adopt “WWMD” (What Would Matt Do) into my practice, though that might result in a more upscale taste to my liking. I’ll be selective when I apply this new way of thinking.

– Tyler

Matt MEAB reacting to his free pizza.

EDITOR’S NOTE: I’m on an annual blogging vacation for the last two weeks of the year. To make sure you still have content, some of the smartest members of the community have stepped up with guest posts in my absence. Special thanks to today’s author, the always helpful and funny SideShowBob233, for writing this post while I’m on vacation. I’ll see you on January 1!

Chase has some of the best checking and savings accounts bonuses, often $500 or $900, and people often jump at the chance to churn these every 2 years.  It sounds great, but when mixed with MS this can be a recipe for a Chase shutdown. 

Chase got in trouble with the feds over their lack of anti-money laundering (AML) compliance a few years ago and as a result has enhanced their AML analysis to a ridiculous level to avoid getting slammed again.  As a result innocent churners and MSers who use Chase are at risk of shutdown by this team.  I know what you’re saying “But SideShowBob233 (you’re saying the 233 part too) I won’t get shutdown I’m not stupid enough to do something to get on their radar” and you’re right – you’re not that stupid but it doesn’t mean you’re safe either.

Many things can get you on their radar that you have no control over:

  • Fraud on a debit card linked to the account
  • Another financial institution having a glitch and pulling a payment multiple times (looking at you Barclays)
  • A fraudulent ACH
  • SideShowBob233 going in your local branch and stepping on a rake while filling out a deposit form and accidentally putting your account number on the deposit slip
  • Some other thing happens that neither of us (and not even your mom!) warned you about

Once one of these things happens, your account will be flagged for review by the AML team, and once they see your activity on your credit cards (and potentially pull your EWS report – more on that later) they will decide you are not worth the risk and shut you down.  OK, so my cards are closed, not the end of the world – but it won’t be just your cards.  It will be the cards of anyone who was an AU on your account, possibly anyone who lives at your address, and also possibly anyone who was ever linked to you via an AU or employee.  And those people will be banned from Chase for at least 7 years, maybe longer although getting back into Chase is YMMV. 

So how do you avoid this?  Simple, don’t have a deposit account (personal checking, biz checking, savings, CD, etc.) at Chase.  Without funds on deposit their AML team doesn’t get to look over your profile.  Their credit card team can still shut you down for rewards abuse or other reasons, but those shutdown for those reasons tend to be whales (although you never know). 

Yes, you are missing out on the potential for multiple checking bonuses but is your Chase relationship worth it (the answer is NO!).  Don’t be like SideShowBob233 (you read the 233 part aloud again because that’s how you roll) and get shutdown because you think it won’t happen to you.  I was in the it won’t happen to me boat, I barely used it other than a direct deposit to keep it free, then I accidentally over-drafted it on a Saturday night paying my credit card after a rake party. 

And finally, if you are going to do it anyway, please tag me when you do get shutdown so I can say I told you so.  But seriously if you do want to get the checking because you are cool enough to avoid the AML team, at least slow your Chase MS when the account is open. 

Stay tuned for my next rant sometime soon on the bane of churning existence (your EWS report). 

Even Canada is listening to SideShowBob233, going as far as naming bills after him.

NOTE: I’ll be going on a blogging vacation between Monday and December 31, during which there will be at least some guest posts. I’ve already gotten a few queued up from readers smarter than me, and I’m soliciting for more to complete the holiday. Posts should be non-sponsored, non-promotional, non-political, and at least travel hacking or churning adjacent. Please reach out to me if you’re interested, it’ll be the third easiest gig you’ve ever gotten!

Introduction

Between 2011 and 2013, it was possible to earn miles for any Amazon purchase through the US Airways and Hawaiian shopping portals. In 2011 I was relatively new to the game and I made a common mistake: I had earned a chunk of US Airways miles through promotions and a credit card bonus, so I decided that I’d earn Hawaiian miles instead whenever I shopped at Amazon, even though had exactly no clear use case. I was sure that at some point I’d use them, just like Southwest CEO Bob Jordan is (incorrectly) sure that Southwest will never have a holiday meltdown again.

Piles of Miles

Now, please join me in 2023 and let’s peek at my current Hawaiian Airlines balance, keeping in mind that I’ve redeemed exactly as many Hawaiian miles as the number of good menu items at Chik-Fil-A, or the number of times that Southwest CEO Bob Jordan has correctly predicted the meltdown future [drumroll]:

Zero (0)

By 2013 I’d earned 40,000 Hawaiian miles through the Amazon shopping portal, but eventually they expired – partially because I was inexperienced and partially because I didn’t ever have a redemption plan in mind. This is a common mistake, especially when you’re stating out. In the last couple of weeks for example, I’ve heard from churners who:

  • Have mid-six figures of IHG points and have never stayed in an IHG hotel
  • Signed up for two Southwest credit cards without even having a Rapid Rewards number
  • Lost 500,000 ThankYou Points after a Citi shutdown, never having used a single point

Obviously some of these are more catastrophic than others, but they all illustrate a common theme: A point isn’t worth anything if it’s never redeemed, and if you have no loose plan, there’s a good chance you’ll never redeem.

MEAB, Get to the Point!

Before you earn any loyalty currency, have at least a rough idea of how you’ll use that currency. Otherwise, you’re almost certainly better off earning cash because at least that doesn’t expire and can be used effectively anywhere, for any travel, as long as your airline isn’t melting down.

Happy Holidays friends!

The easiest gig you’ve ever gotten.

Historically American Express takes just a couple of days to post sign-up bonuses on Membership Rewards earning cards, statement credits, card-linked offer awards, retention bonuses, and employee spending bonuses after the terms are met. Perhaps due to cold weather, or maybe due to the launch of a new Membership Rewards program in India without enough infrastructure to handle it, those credits and bonuses that used to post in a few business days are taking longer and longer to post. Typical posting timeframes:

  • August: 1 – 3 business days
  • September: 2 – 4 business days
  • October: 3 – 5 business days
  • November: 5 – 7 business days
  • December: 7 – 12 business days

Beyond the obvious delayed dopamine hit, why should we care? Easy. For some statement credits tied to the calendar, your credit often counts in the month that it posts even if the charge was in the prior month (though even that’s not completely consistent).

So, I’d consider this week your last week to use your airline credits, wireless credits, garbage credits (Dell, Adobe, Clear, etc), food credits, and other coupons to guarantee that they post before the month’s and the year’s end. Don’t be #bonvoyed!

Good luck, and happy Tuesday!

Pictured: American Express’s messaging system between the charge department and credit department.

NOTE: I’ll be going on a blogging vacation between December 18 and 31, during which there may or may not be any posts. But, we’ll ring in the new year on January 1, 2024 with the 2023 version of Travel Hacking as Told by GIFs though, so no need to be up in arms. What’s this “may”, you ask? I’m soliciting for guest posts and I’ll use those during the regularly scheduled newsletter. They should be non-sponsored, non-promotional, non-political, and at least travel hacking or churning adjacent. Please reach out to me if you’re interested, it’ll be the third easiest gig you’ve ever gotten!

In person manufactured spend has multiple potential points of failure, but the most silently insidious is buying a Visa, Mastercard, or third party gift card and discovering that it’s been tampered with after you’ve bought it. Time isn’t on your said when that happens because it gives the scammer more opportunity to drain the card before you’re able to act.

Most tampering scams require the scammers to check cards at least daily to see if they’ve been activated, so you’ve got an expectation value of a few hours time between when you buy the card and the moment that a scammer discovers it’s been activated. That means a stack of gift cards on your desk waiting to be liquidated has an increasing likelihood of issues, and a decreased expected net value over time.

The obvious takeaway? Open and inspect cards you buy immediately and liquidate as soon as possible (whether or not you’ve been scammed, but obviously especially if you’ve been scammed.)

Stay safe out there!

The rule also applies to this, err desert, the longer you wait between eating and the food exiting your system, the higher the risk to your digestive health.

Card issuers like American Express and Chase famously have cards with:

  • Statement credits that reset every calendar year
  • An annual fee that posts on the 12th statement
  • The ability to cancel a card and refund the fee for 30 days after it posts

Taken as a whole, these three bullets mean that late November and December are the ideal times to get a credit card with annual credits. For example, the American Express Business Platinum card has:

  • $200 airline incidental credit every calendar year
  • $200 Dell credit every six months
  • $189 Clear credit every calendar year

If you get the card on December 1, 2023, then your 12th statement won’t generate until (at the earliest), December 15, 2024, and thus you can get an annual fee refund through January 14, 2025. That means as long as you hit spend early and cancel the card before January 14th, 2025 you’ll get:

  • $600 in airline incidental credits (2023, 2024, and 2025)
  • $800 in Dell credits (2H2023, 1H2024, 2H2024, 1H2025)
  • $450 in Adobe credits (2023, 2024, and 2025)
  • $567 in Clear credits (2023, 2024, and 2025)
    (though you should discount those Adobe and Clear credits significantly)

There are a few gotchas to watch for, such as how Bank of America’s annual fee refund after an annual fee posts isn’t guaranteed, or how the Chase Sapphire Reserve’s travel credit is tied to cardmember year, not calendar year. But, you’re enterprising people, right?

Good luck!

The triple dip visualized as jello. From top to bottom, red (2023), white (2024), and confused (2025).