Category: Wisdom

Introduction

I’m not a financial advisor and I’m definitely not your financial advisor, but I get questions almost every week about my investment strategies for reasons known only to Betty Badluck. My best advice: seek a low cost total market index fund and HODL. Of course this isn’t that kind of blog though, but there is a travel hacking angle here so: Hey, how you doin? Let’s chat!

My Strategy

My investments fit a simple allocation strategy, and I rebalance my portfolio every three or so months to make sure that the allocation stays proportional:

  • 45% VTI
  • 45% VEU
  • 10% MEAB special

What’s the MEAB special? It’s stocks that I pick individually for some particular reason, but proportionally allocated in a way such that a catastrophically bad pick won’t be able able to wipe out the majority of my holdings. Historically that 10% generally outperforms the rest, but I attribute that to luck moreso than skill and don’t expect that it’ll continue that way.

The Travel Hacking Angle

There’s always a travel hacking angle, right? Well, as frequent flyer hackers we get an inside view into the operations, rise, and fall of airlines in both a specific and general sense. For me, that means that I have an insider view into how an airline performs that goes above and beyond the information in a 10-Q, and if I’m going to be choosing an airline to hold in the 10% MEAB special, that information may or may not give me an edge.

To be clear: investing in airlines is a tough business and I don’t recommend it, but if you do it, augment the public filings with information you’ve got from your inside view.

Finally, to answer the question that exactly none of you asked: When I invest in the airline industry I short one airline stock and long another airline stock to try and earn based on relative performance while avoiding losses from general industry crapluence. Sometimes it works too, probably just like sometimes a broken analog clock is right.

MEAB’s investment skill.

In the last day there’s been a wave of Chase shutdowns that have swept through very specific parts of the community. All of the data-points I have suggest everyone shutdown has had two things conspiring against them in tandem:

  • An account on their credit report listed as “Closed by issuer”
  • A negative Ultimate Rewards balance (largely related to chargebacks)

From my perspective the likely timeline was: A negative Ultimate Rewards balance led to an analyst getting involved, the analyst soft-pulled a credit report and saw derogatory marks and applied a two-strikes rule, then the analyst queued the account for closure.

Some unsolicited advice when dealing with banks and rewards, Chase or otherwise:

  • Don’t let your points balance or card balance go negative at statement close
  • If one of those does go negative, transfer points and/or spend as necessary to get it non-negative
  • Dispute away any derogatory remarks from your account (persistence will eventually pay off)

If you’re shutdown, know that a shutdown at Chase is generally better than a shutdown at other banks because with a little luck and good timing, you’ve got a points machine.

Have a nice weekend!

Pictured: The Chase shutdown wave hitting some unlucky manufactured spenders.

We’ve talked before about getting out of the various American Express penalty boxes, which is when AmEx won’t give you referral links or gives you a pop-up telling you that you’re not eligible for a welcome bonus on new applications. Despite some noise to the contrary that keeps surfacing, the main way out still exists and it remains the same:

Spend a lot on your existing AmEx cards

What’s missing seems to be what “a lot” means, so let’s clarify based on what we know:

  • $30,000 – $40,000 a month for three months on a co-brand card almost always gets you out
  • $40,000 – $50,000 a month for three months on a Membership Rewards or cash-back earning card will probably get you out

Of course neither of these are fool-proof but based on data-points I’ve worked with, this volume of spend will work about 80% of the time. It’s also even worked even after a past bankruptcy write-off with AmEx.

What if you don’t have a co-brand card? Apply for one even if you get the pop-up with no bonus, then start spending. There are a few no-annual fee co-brand cards like the Delta Blue and the Hilton Honors card so you’ve got options.

Good luck!

Now we just need to have AmEx send these when someone spends their way out.

What defines a whale in the miles, points, and manufactured spend game? It’s hard to quantify exactly, but it’s easy to use a relative definition so let’s cheat and use one of those. For my purposes and for the purposes of this post, a whale is someone that’s spending 10x what I’m spending or more.

In my career as a manufactured spender, I’ve met dozens of whales, and the deeper I get into the hobby the more frequent my encounters become. I’ve learned something from each of them, and usually that boils down to a single lesson:

The limits aren’t usually what I thought they were.

That’s not to say that limits don’t exist, they most certainly do. Banks will shut you down when you go too hard, credit card companies often don’t tolerate heavy cycling, and too many wires or money orders can lead to the FBI, IRS, or postal inspector showing up at your doorstep (which will probably turn out to be a nothingburger, but not before you have a few sleepless nights stressed out about what might happen.)

If you’re like me though, limits are often quite a bit higher than you think, and whales can be your data-point for how much further you can push things. Whenever possible, seek out these whales and their data-points, learn from them, and step-up your game as appropriate.

I mean, you can’t tell me that this whale teacher looks less weird than your high school english teacher, and you learned something from them too, right?

I’m sure you’ve heard that United “MASSIVELY” devalued its award ticket prices in a “disappointing“, “heartbreaking“, “major” way yesterday. Yes, it sucks, and yes you should be unhappy about the situation. But, events like this are unfortunately the most predictable occurrence in travel hacking, even more so than Frontier having another failed dartboard route or LHR imposing punitive premium cabin surcharges. We know that it’s going to happen.

One of the most interesting pieces of advice I got as an adolescent was from an investment banker with a brand new Jaguar. As 15 year old grocery clerk me loaded groceries into his trunk, he said “If you can’t make a profit when you absolutely know something is going to happen, then I don’t know what to tell you”. He was completely right and the advice is sound (he was talking about death by the way, you know, upbeat and stuff like all investment bankers).

For travel hacking, we might have to stretch the definition of profit a bit when we apply the logic to award bookings, but we can do it. Here’s how we “make a profit” when we know a devaluation is going to happen:

  • Book early, book often – if there’s a devaluation, already issued tickets don’t go up in price and most award tickets are refundable for no-fee or for a very small fee
  • Keep your points in a flexible program like Ultimate Rewards or Membership Rewards until the moment you need to book
  • Book with alliance partner miles when prices are lower
  • Don’t let your points balances grow into seven figures and beyond, and especially don’t let that happen in multiple programs (I failed here, big time)
  • Focus on cash back once you’ve got enough points for the current booking window’s trips (it turns out cash is fungible)

Happy Thursday!

Next up: Determine whether this is a devaluation. Actually never mind, I don’t care.

My physicist brain wants to turn everything into a simple model that may or may not map well to reality. For manufactured spend it usually does though, and analogues with the physical world help too.

To illustrate, let’s set your way back machine to your high school physics class (assuming you were cursed with one) and recall the basic, simplest formula for calculating the velocity when you’ve moved some distance in some other amount of time:

speed = distance / time

Now, translate that into a formula that we should live by:

profitability = earnings / time

The profitability of a play isn’t a simple milage count or a sum of cash, unless we’ve got unlimited time. Because we don’t, doing something that earns 1% but takes 30 seconds should beat something that earns 5% but takes 20 minutes assuming infinite scalability. Of course not everything is infinitely scalable, so perhaps you can do both with the time you’ve got. But, if you’re making a trade-off, do consider that a 1% play can beat a 5% play.

Happy Monday!

No, I never had this shirt. Yes, I always wanted to make one.

It’s easy to get buried in details in the hobby, and in fact the details are usually where we find outsized value. That said, having a macro view on the space also helps us play the game. I want to focus on two specific instances of major movements in the last couple of days to illustrate the point:

Keeping your eyes on the macro can help you with the micro. Bank takeovers and acquisitions matter friends!

Tuesday inspiration, I guess?

  1. Even though it started a few weeks ago, I think I only realized yesterday that we’ve apparently all agreed that there’s a new, fifth season of the year (“no-feepril”) in which office supply chains across the US take turns offering fee-free or below cost Visa or Mastercards every week throughout the season.

    Office Depot / OfficeMax drew the short straw this week and has a sale for $15 off of $300 or more in Visa gift cards through Saturday. To maximize the deal:

    – Link your cards to Dosh
    – Look for a Chase offer for 10% back at Office Depot / OfficeMax
    – Try for multiple transactions, back to back
    – Buy the grocery, fuel, or dining everywhere varieties for lower fees

    These are Pathward gift cards but there are still plenty of ways to liquidate them both online and in person. If you don’t have a few ways it’s time to get out there and look.
  2. A public link for the Chase Marriott Bonvoy Boundless card with a bonus of five free night certificates worth up to 50,000 points per night after $5,000 in spend in three months has surfaced. The card has an annual fee of $95, and is probably the best deal you’re going to find with Marriott. A few notes:

    – You’re still going to pay for parking and resort fees with these, because Marriott
    – If a property costs more than 50,000 points per night, you can use up to 15k award points too
    – The certificates expire after one year

    I’m famously a Marriott Bonvoy super-critic, but even I’d go for this offer if I was below 5/24.
  3. Finally, let me offer some unsolicited American Express advice for those of you with with big negative balances because reasons:

    Always keep your balances as close to $0 as possible at the end of every banking day to avoid financial reviews or problems with the risk department. This applies as equally to negative balances as it does to positive balances.

Good luck and happy Monday!

Obscure fact: Sometimes Bonvoy and Office Depot/OfficeMax team up. This is the result.