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?

Not considering the opportunity cost

When purchasing my house, I was very proud of how I used a 0% offer on a Chase Freedom Unlimited card and some credit limit transfers to get $43,000 loan for no cost. This was a fun act of financial engineering, and I calculated that it saved me about $654 in interest on a loan I’d taken against my assets. Putting that spend on my Chase Freedom, however, meant that I wasn’t using it to hit sign up bonuses. That $43,000 would have been enough for seven Chase Ink Cash/Unlimited sign up bonuses, at $750 each (or a mix of equivalently lucrative offers). That means I gave up a chance to make $5250, just to save $654.

My tactic to avoid repeating this failure is:

  • 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.

Not valuing my time

For a great take on this, which highly resonated with me, read Kai’s post from last year’s blogging vacation. For my concurring take, read on.

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.

Want more content like this?

If you’re interested in content like this, check out my blog. There’s a subscribe box at the bottom of every page, if you’re interested in seeing new posts as they come out. And if you think I’ve missed something, gotten something wrong, or should write future posts on a particular topic, please drop me a line.

– Graham

Other fails in no particular order.

The last week of November saw groups of shutdowns from three major banks: Discover, Wells Fargo, and Chase. If you were affected, sorry – that sucks. But even if you weren’t, we can learn from what happened. Let’s go bank by bank:

Discover

Summary: Repeated negative balances pushed the risk team over the edge.

Explanation: One of the tricks of the trade in high volume manufactured spend is to prepay your credit lines, creating a negative balance on your account in order to be able to spend more than your credit line. Some banks don’t care when you do this, but Discover isn’t one of those banks.

Lesson: Be cautious about overpaying credit lines. Discover isn’t the only bank that doesn’t like it.

Wells Fargo

Summary: Non-standard payment methods spooked the risk team.

Explanation: Sometimes paying a credit account directly via ACH isn’t the best way to pay; as a /r/OldSchoolCool inspired example, CheckFreePay at Walmart Money Centers used to be a great way to pay your Visa and Mastercard bills using Visa and Mastercard gift cards. In the case of recent shutdowns, a payment method that a regular customer wouldn’t normally use was advantageous, at least until Wells Fargo decided it wasn’t.

Lesson: Consider the source of payments to your credit accounts, often banks don’t like abnormal payment methods, and side note: that’s especially true with anonymous payment methods.

Chase

Summary: Prior chargebacks related to fitness club associations finally caught up to bag holders.

Explanation: There was a private manufactured spend group a few years ago that imploded, leaving hundreds of people with outstanding money that wouldn’t be paid back (no, this isn’t Synapse). Some people initiated chargebacks on that money, occasionally well into five figures or more, and Chase finally decided that those chargebacks made account holders personae non gratae.

Lesson: If you ever need to use chargebacks to bail yourself out, make sure the value of the chargebacks exceeds the value of your relationship with the bank.

Good luck out there, and happy Wednesday friends!

Another potential shutdown affecting all churners: Failed identity verification.
(Thanks to Vince for the unfortunately real screenshot)

About two weeks ago, several popular travel bloggers dropped hints about visiting a corporate sponsored affiliate meeting from a company named Mesa. Since then I’ve been expecting a deluge of articles about their newly launched card, but for the most part nothing has appeared. Why? I assume news is embargoed until Mesa says it’s ok to write about it, preferring to soft-launch in relative quiet with a waitlist and then go big at just the right time™. On the other hand though, you know what they say about assuming.

Anyhoodles, since I’m under no embargo and I guess I don’t care about soft versus full launch, let’s discuss the rewards system and the waitlist credit card in a no-quid-pro-quo kind of way. It’s a lot like Bilt in that there’s a way to earn points whether or not you have the card, but you can earn more with the card. It’s unlike Bilt in that its VP isn’t telling people how to game their own company, or seemingly lying about being an industry-first program to launch earning on mortgages.

Earning

Whether or not you get the card, you’ll earn a point for each dollar when you originate a new primary loan or a refinance an existing primary loan, as long as you use a “The Mesa Mortgage Marketplace Lender”, which I guess we’ll abbreviate as TMMML because reasons. You can do that up to five times per account too.

But, how good are those TMMMLs? Well, when I put in my address, I got a single option: Swift Home Loans Inc which is apparently a mortgage broker based out of Birmingham; but not that Birmingham, it’s the Michigan one. So I guess there’s exactly one TMMML (at least for my state) and they’re rated 2.8 out of 5 on Facebook. I dialed their main contact number to ask about which banks they work with and what sorts of mortgages they can handle, but it just rang for a good minute so I hung up. Looking pretty great guys!

How about the credit card? It’s a Visa issued by Celtic bank and carries no-annual fee. The earning structure:

  • 3x on HOA fees, contractors, homeowners insurance, property taxes, home decor, and other “home-related” charges
  • 2x on gas, groceries, EV charging, and utilities
  • 1x on a linked mortgage, but only on up to $100,000 in mortgage payments annually
  • 0x on other spend, as far as I can tell
  • Free Sam’s Club membership

Like with Bilt and rent, you don’t need to put your mortgage payment on a card to earn points on mortgage payments.

Burning

There are two options for redeeming Mesa points: booking travel through their portal, and gift cards. The cash value of each, based on my sampled searching:

  • Travel: 1.0 cents per point, but also a fixed 400 point extra surcharge per flight
  • Gift cards: 0.7 cents per point

Everything Else

Here’s how I’d look at this card, considering that if you’re booking travel through a portal you’re not going to use Mesa because Chase and AmEx have much better value propositions:

Gift card options include popular bulk brands like BestBuy and Apple, and assuming a resale rate of 93%, that means you can cash-out your points through gift cards at 0.65 cents per point 🤏. So:

  • You earn 0.65-0.70% back on mortgage payments just by holding the card
  • You get a 0.65-0.70% rebate on new mortgages, but those are probably baked into the fees of the one member of the TMMML
  • You’ll do better for other spend, manufactured or real, with other credit cards.

Finally, I extracted the full terms and conditions of the rewards program from the mobile app in case you’re curious, and it’s just this webpage.

tl;dr: It’s ok I guess, but you can probably skip the dozens hundreds thousands of affiliate articles when they come out in (probably) the next couple of weeks.

Happy Wednesday!

Kick-off party for current members of TMMML.

  1. There’s a new public link on the front page of Delta.com for increased sign-up bonuses on American Express cobranded cards. There’s a second link buried at creditcard.delta.com too, so try both if one doesn’t work. Unlike most times when the blog-o-sphere is saying “more people targeted” because someone said so on reddit, this time it actually appears to be true; No, I’m not bitter, you’re bitter! Anyway:

    – Reserve: 100,000 miles after $5,000 spend in six months
    – Platinum: 90,000 miles after $3,000 spend in six months
    – Gold: 70,000 miles after $2,000 spend in six months
    – Reserve Business: 110,000 miles after $10,000 spend in six months
    – Platinum Business: 100,000 miles after $6,000 spend in six months
    – Gold Business: 80,000 miles after 4 $4,00 spend in six months, waived annual fee

    If you get the popup, try the other link which often has different popup criteria.
  2. If you have money locked up with Yotta or Juno thanks to the Synapse FinTech collapse, check your email for a payout link from one of the underlying banks that was servicing accounts, Evolve. There are multiple reports of payments being correct and several where people are short, at least one by over $94,000, though it’s not clear whether that money was put at Evolve by Synapse or put somewhere else. To find the email, look for one of:

    – Email: [email protected]
    – Subject: Return of Synapse Brokerage’s End User Funds

    Don’t forget to add “in:anywhere” to your search to look through spam and other folders in your inbox. If you don’t have your email yet, there’s a completely unverified rumor that it may take until the 16th to send all emails.

    In related news, apparently Evolve’s CTO and CEO/President have been terminated. I’m not saying that’s unjustified especially after Evolve leaked customer information in a data-breach, but it’s strange to see everyone going after Evolve leadership instead of Synapse leadership.
  3. Capital One has a 20% transfer bonus to British Airways Avios, and by extension all airlines that use Avios through December 1. (Thanks to jtevy)
  4. The American Express Centurion Business card will have a cap on its 50% airfare booking rebate at 3 Million rebated points annually starting on February 1.

You can’t hold someone accountable if they can’t account I guess?

Let’s focus on news from a few banks today:

  1. Bank of America’s Preferred Rewards status was removed from many business accounts on September 6, and it seems related to early enrollment during new account setup. If you’re affected, there are two action items:

    – Consider whether you want to pause spending on Bank of America cards until it’s fixed
    – Consider contacting Bank of America and opening a case

    Generally speaking, calling a bank as a manufactured spender about missing rewards isn’t the best idea, it’s kind of up there with betting in Vegas on John McCain winning the 2024 Presidential Election; but in this case I think the team you’ll be working with (Preferred Rewards) is sufficiently distant from the rest of banking that the risk is low and reward is potentially high. You’re all adults, so make your own judgement call.
  2. If you’ve given full, non-Bank of America card numbers to Bank of America representatives recently, consider locking or replacing those cards; there are multiple correlated reports of fraudulent charges that surfaced yesterday stemming from Bank of America.
  3. Bloomberg reports that Barclays is nearing completion of a deal to purchase the Marcus GM portfolio of credit cards in a few months. If you’re banned from Barlcays, getting a GM card now could be a way back in. UPDATE: This didn’t work for people banned by Barclays when they acquired the Banana Republic card, so adjust your calculus as necessary.

Have a nice Thursday!

Bank of America’s vault mirrors the rest of their technology stack.

Background

Behind most FinTechs is one of a handful of partner banks, common ones include: Evolve, Stearns, Sutton, Cross River, and Celtic, but there are others. Somewhere between an average FinTech and a partner bank you’ll sometimes also find a Banking-as-a-Service player, and there are even fewer of those. Common BaaS names that you may have heard of are Solaris Bank, Green Dot, and Solid.

NOTE: In case you’re wondering, Banking-as-a-Service is nicknamed BaaS because the finance industry often lacks creativity and tries to hide it with focus group generated names designed by committee to appeal to millennials on paper, but the names they arrive at don’t actually appeal to millennials in practice.

April Showers

Synapse, a somewhat popular BaaS platform, filed for bankruptcy in April and for the most part no-one noticed because everything seemed ok for FinTech platforms built using Synapse, because TabaPay (yet another BaaS) struck a deal immediately to buy Synapse’s assets and assume its business operations.

May Gray

A few days ago though, TabaPay announced that it was terminating its purchase agreement of Synapse because of issues with TabaPay’s partner bank, Evolve, funding accounts related to the transaction. Of course, just like a reality TV show, Evolve says that it’s not true because of course they did. Then, Evolve froze the assets of multiple FinTechs built on the Synapse platform because of course they also did that.

After the agreement was called off on Tuesday, a bankruptcy judge went on record to say that up to 20 million FinTech depositors are at risk due to Synapse’s bankruptcy and the failed deal. What does at risk here mean? It’s not fully clear, because typically a BaaS’s partner bank holds custodial accounts for customers and those are FDIC insured, but if they’re frozen and you can’t withdraw them, then FDIC insurance doesn’t mean anything for access to your cash. Additionally, depending on the financial structure of the custodial account, FDIC insurance may be insufficient too.

The Effect on FinTechs

Since Evolve froze FinTech accounts worth $114,000,000 related to Synapse this week, we’ve seen ripples through multiple FinTechs including Juno and Yotta, each of which have had their customers’ accounts frozen by Evolve. My personal, uninformed opinion after watching the Silicon Valley Bank drama is that the federal government won’t let FinTech users lose this money, but of course my opinion tends to have no bearing on reality.

The Advice you didn’t Ask For

Juno had been an interesting tool for manufactured spend at multiple points in the past, but that’s changed recently even without the Synapse drama. Some manufactured spenders still have significant funds on deposit that’s no longer accessible though, and there are indications of issues at other FinTechs too, including but not limited to Yotta. So, while the Miles Earn and Burn way is “always be probing”, I’d sit back on probing any FinTechs that might be involved with Synapse for the time being.

Good luck out there friends!

The finance community’s premier product and industry name committee.

  1. Albertsons, Safeway, and Vons stores have a promotion for $10 off of a future purchase good for seven days with a $50 purchase in several third party gift card brands through October 10. Lowe’s is the best one for resale rates, currently averaging somewhere around 89%.

    It’s possible that this is a regional only deal so double check your ads, though I suspect it’ll work everywhere. (Thanks to GCG)
  2. Shoprite stores have $10 in grocery credits $150 or more in Mastercards through Saturday, limit one per account. The credit is valid starting Saturday and running for a week, and recent reports suggest Shoprite stores putting $7.95 fee cards on the rack, because of course they are. (Thanks to DoC)
  3. Do this now: Sign-up for the waitlist for the future TAP Portugal American Express card. Getting on the waitlist means you’ll get a bigger bonus if you decide to apply for it when it launches, but doesn’t obligate you to anything.
  4. Do this now: Check chase.com/mybonus for targeted offer of 5x-10x on spend on grocery, utilities, fitness, internet, and/or phone services on your personal co-branded cards.
  5. In a move that should surprise no-one, Delta devalued partner awards to and from Mexico, the Caribbean, Central, and South America. Award prices for business class have risen by approximately 40%, and economy prices have risen more modestly by approximately 15%. When asked to comment on this change, Delta again used a single word response: “Budgeting”, but this time they played the wah-wah trombones while speaking.

    As of this devaluation, the rule of thumb for non-expert travel hackers is that Delta SkyMiles are mostly only good for US economy awards. There is slight value to be had outside of that paradigm, but it diminishes regularly.

Delta’s PR team discussing the most recent award ticket redemptions.

We’re in an extended period of Chase shutdowns that started a week ago, and while we don’t know the complete causes, related factors might be:

  • Heavy use at a manufactured spender fitness club
  • Earning a sign-up bonus at a manufactured spender fitness club or popular rebate site, even with light spending
  • Using Chase Ink card links that bypassed backend business approval logic

If you’re caught up in shutdowns, there are options to squeeze Chase back, not all is lost:

  • Call or write the Chase Executive office and open a case
    This is only likely to be fruitful if you’re shutdown for rewards abuse and don’t have heavy manufactured spend, or if you’re shutdown due to bust-out risk. For body builders, I don’t expect a ton of success here
  • Exercise the arbitration clause in your account agreements
    I’m not an attorney and I’m definitely not your attorney, so don’t take this as legal advice. I imagine that having a manufactured spend friendly attorney on your side couldn’t hurt though
  • Wait seven to ten years and you may find yourself back in
    Yes it’s a long time, but it’s not forever
  • Find new players
    Isolate addresses to avoid any contagion spread through
  • Try and open a Chase Private Client account in branch
    Wait six months to do it, and you’ll need $100,000 or more in assets typically
  • Pivot to other banks for cash, United, and Hyatt
    Bilt is an option. You weren’t using Ultimate Rewards for much else, I assume?

Fortunately there are thousands of banks and credit unions out there that offer credit cards that still want your business. Always be probing!

Squeezing Chase if Chase were a GM car.