What I'm thinking about headed into 2017

Good morning from Portland, Oregon. If you're traveling for the holidays, I hope your flights are safe, comfortable, and on time and your roads are clear. As 2016 staggers towards a close it's natural for thoughts to turn to the new year. Here's what's on my mind.

Manufactured spend

Last week I read a post-mortem on 2016 that claimed manufactured spend was either dead or dying, and I assume there are parts of the country where that's more or less true. In other parts of the country the amount of spend you can manufacture is limited only by the time and attention you're willing to dedicate to the task.

As 2017 starts I'll be moving spend back to my Delta Platinum Business American Express to start running up the score on Medallion Qualifying Miles and towards a Medallion Qualifying Dollar waiver. I don't chase high-level Delta status anymore, but do enjoy the free checked bags and decent seat selection I get as a Delta Silver Medallion. The real reason I manufacture spend on that card, though, is the 1.4 SkyMiles per dollar I earn at the $25,000 and $50,000 spend levels. Since I value SkyMiles at more than 1.5 cents each, that's more valuable to me than putting the same spend on a 2.105% cash back card.

In the last couple months I loaded up on spend with my Chase Hyatt credit card in order to hit the $40,000 spend threshold, but my expectation is I won't be putting any spend on that card in 2017. The annual Category 1-4 free night award will still justify paying the annual fee, for now.

The biggest change to my manufactured spend practice is that thanks to some current opportunities I expect to spend much more time in drug stores and much less time in Walmarts in 2017.

Blogging

In the 2-and-change years I've been writing this blog, it's changed in a lot of ways. When I started I spent a lot of time documenting and describing the tips and tricks I was reading about on other blogs and FlyerTalk. As time went on I became more focused on exploring new opportunities and, as I put it, explaining "how things really work." Recently I've become more focused on optimizing strategies for particular goals, and I've become even more cynical (if that's possible) about the parasites who put their own interests above those of their readers.

I've lost some readers as my focus has shifted over the years, and I've also gained readers who appreciate my newer content more than the older. This blog will never be all things to all people, but it'll always be independent.

In 2017 I hope to write some more book and podcast reviews, since I read a lot and listen to a lot of podcasts, and I enjoy the opportunity to collect and distill my thoughts about them.

Subscribers-only Newsletters

In the last few months I've stepped up the tempo of the periodic Newsletters I send out to monthly blog subscribers. Partly that's because there's been a surge of new deals towards the end of this year, and partly it's because I enjoy the opportunity to write unconstrained from fear of "killing" somebody's favorite deal.

I'll always maintain this public blog because I think it's important to have as many unbiased voices available as possible as a counterweight to the mercenary affiliate bloggers flooding the internet. But deals and ideas that might be threatened by widespread exposure will continue to go in my Subscribers-only Newsletters.

And by the way, if you enjoy this blog I hope you'll consider supporting it with a monthly blog subscription in 2017!

Gambling

During the Great Financial Crisis, the federal government took the two main federal home loan insurers into conservatorship. For a range of technical and legal reasons, however, they did not force them into bankruptcy and did not wipe out the existing shareholders. And, strangely enough, those shares are still traded for just under $4 on the over-the-counter markets.

I think there's a non-trivial chance the new Administration will stop sweeping the GSE's profits into the Treasury, and those shares will become 10-100 times more valuable. So I bought some!

This isn't advice, just something I'm looking forward to in 2017.

Travel

2017 will be my year of Hyatt stays. After March 1, as a World of Hyatt Globalist I'll be eligible for suite upgrades on award stays. Plus, since I won't be trying to requalify as Globalist for 2018 I'll be free to redeem Hyatt points for all my stays and not be constrained by the availability of Points + Cash awards.

Already in the works are trips to Jamaica to stay at the Hyatt Zilara Rose Hall and to Lexington, Kentucky for the April races at Keeneland. Beyond that, the plan as always is to keep my eyes open for international travel opportunities, as well as shorter weekend trips domestically.

Things I have learned about booking Hyatt all-inclusive resorts

In the past few weeks I've gone from vaguely speculating about booking a winter weekend at a tropical all-inclusive resort to starting to plan an actual trip. Since, for good or ill, I'll be a Hyatt Gold Passport Diamond/World of Hyatt Globalist next year, I've been looking at Hyatt's all-inclusive properties. Here are a few things I've learned so far.

Standard award availability is very tight

At the Hyatt Zilara Rose Hall I happened to reserve the last standard room available over Presidents' Day Weekend, which is quite a few months from now.

At the Hyatt Zilara Rose Hall, the only room types bookable at the 25,000-point level are the "Hyatt Zilara King" and "Hyatt Zilara Double" room types.

Suite award availability may be a bit better

While there are no more standard room awards over Presidents' Day Weekend at the Hyatt Zilara Rose Hall, there are still suite night awards available.

According to the phone representative I spoke with, at the 40,000-point level I could still book the "Junior Suite King" room type.

The point is that even if you don't have any reason to book a suite, if you're willing to spend the additional points you should ask anyway, since you may have access to additional award space you wouldn't have if you insisted on booking a "standard" room award.

Since during peak times those rooms can be phenomenally expensive, you may still save money even when "overpaying" for suite night awards.

Cancellation policies are brutal

My award reservation at the Hyatt Zilara Rose Hall has a 45 day cancellation policy. That means in the first couple days of January I've got to decide whether I'll really make it to Jamaica in late February.

Feel free to book these awards speculatively, but also keep track of their cancellation policies and don't get caught paying some preposterous cancellation penalty for missing it by a day.

Hyatt Gold Passport Diamond point loans still apply

On a final note, it is possible for Hyatt Gold Passport Diamonds to book award nights without sufficient points in their account. This is a pretty cool feature which can be used for domestic and international award stays, and can also be used for all-inclusive award stays.

I am not ready to be seduced by Southwest

Now that I'm finally a short commuter train ride, rather than an inconvenient bus ride, away from a Southwest hub I assumed I'd be flying Southwest a lot more. After all, they offer a variety of nonstop flights around the country, Mexico, and the Caribbean, and when "Wanna Get Away" fares are available Ultimate Rewards points are worth more transferred to Southwest than when redeemed for paid flights on other carriers.

But it turns out I still don't fly Southwest, for excruciatingly simple reasons.

Southwest doesn't participate in — or have their own — decent search engines

ITA Matrix is kind of primitive, and I understand that Google is trying to encourage people to use Google Flights instead. But both search engines are great! You can use ITA Matrix to produce a list of flights that correspond to criteria you specify in advance, and you can use Google Flights to alter your search on-the-fly to dial in the airlines, dates, and airports you want to search. Two great tastes that taste great together.

By forcing you to use their own garbage search engine every time you want to find a Southwest flight, Southwest increases by 50-100% the amount of work necessary to compare all the relevant flight options.

Why do I say the search engine is garbage? Here are a few things you can't do using Southwest's search engine:

  • Specify non-stop flights;
  • Specify flexible dates;
  • Specify specific fare classes.

Each of one these requires you to wait for search results to load, and reload, and reload, and reload, while they can all be specified in advance using ITA Matrix or specified on-the-fly with Google Flights.

Southwest is not a low-cost carrier, it's just inconvenient

The reason I've got Southwest on the brain is that I'm trying to plan a Caribbean getaway for early next year and I keep thinking, "I should check Southwest flights." Then I check Southwest flights and get frustrated that I'm wasting my time.

Here's Southwest's one daily non-stop flight from Baltimore to Montego Bay, Jamaica, over Presidents' Day weekend:

And here are two perfectly good American flights (with a connection):

The question to me isn't whether the Southwest flight is "better" or "worse" than the American flights, it's whether the Southwest flight is going to be better by enough, often enough, to justify jumping through their hoops in addition to the ordinary searches I do for paid tickets and awards on real airlines.

Booking Southwest flights can be worth it, but you've got to commit to shenanigans

I don't want to cast aspersions on the judgment of readers who decide that Southwest is the right airline for them. But if you do decide to make Southwest part of your life, there are two important things to keep in mind.

First, always book tickets out of funds in your Southwest account. Most fixed-value rewards currencies can be used to book Southwest tickets in every fare class except "Wanna Get Away" fares. But since Southwest tickets can be freely redeposited into your account and reused, you can apply the credit from your high-value ticket redemptions to cheap Wanna Get Away fares. That means 20,000 Flexpoints can be redeemed for any $399 Anytime fare and that $399 fare can be used to book 2 $200 Wanna Get Away Fares. This is one of the key benefits of Southwest and if you're not using it you're likely leaving money on the table.

Second, consider chasing a Companion Pass. While plenty of affiliate bloggers will tell you how easy it is to earn with Chase credit card signup bonuses, it's also easy to earn through every other method of travel hacking: shopping portals, reselling, manufactured spend, and of course actually booking paid tickets. By doubling the value of your Rapid Rewards points and doubling the value of the funds in your Southwest account, a companion pass can legitimately bring down the cost of Southwest tickets enough to offset the inconvenience of being seated in a cattle car (not that I'm biased).

Conclusion

My older brother is a Southwest enthusiast. He got into travel hacking for the sole and exclusive purpose of getting a Southwest Companion Pass, and he took full advantage of it for 4 years as he got married and had kids. He was sure to check in 24 hours before each flight to get the lowest boarding number. And now that his last year with a Companion Pass has lapsed he's always complaining about how much flights cost.

And that's basically my point: Southwest isn't a low-cost carrier, and it doesn't have any particular advantage in convenience or comfort. It's a lifestyle, and there are a lot of people who are enthusiastic about that lifestyle.

I just don't think I'm ready to become one of them.

Liquidating tiny-denomination prepaid debit cards

If you read yesterday's post and rushed out to buy up a slew of 5% Back Visa Simon Giftcards, and then triggered 5% cash back on each of them, you are probably feeling pretty good about yourself.

You're also probably realizing that you've got a drawer full of $25 Visa debit cards, and may need some suggestions for liquidating them. I'm here to help.

Buy gift credit

If there's a particular world-swallowing online merchant you do a lot of shopping with, you can simply use your $25 debit cards to reload your gift card balance.

This goes for any merchant where you have a consolidated or well-organized method of keeping track of gift credit — Uber and Starbucks spring to mind, with their beloved smartphone apps.

If you are buying gift credit at a merchant where you already reliably spend money, this is a good way to convert prepaid debit cards into cash savings, as long as your swollen gift card balance doesn't make you spend more money than you otherwise would have.

Pay bills

I don't personally have very many bills, but I'm assured by experts that most people have a great many bills. They might be:

  • Phone;
  • Internet;
  • Cable;
  • Walker (dog, cat);
  • Insurance (homeowner's, renter's, car, health, dental, long-term care, yacht, RV, flood, drought);
  • Utilities (electric, gas, hot water, cold water, lukewarm water, elevator, heating oil, cooling oil).

Some of them may accept debit card payments at face value. Even if you usually make these payments quarterly or annually, you may be able to prepay them and have the balance roll over from one billing cycle to another.

This is a basically excellent idea, but like buying gift credit, you will quickly run into problems when you're producing more $25 Visa debit cards than you need to cover even your most speculative bill payments.

Liquidate as usual

Of course, these are PIN-enabled Visa prepaid debit cards, so it's also perfectly possible to liquidate their (small) balances as usual: by buying money orders or making bill payments at any merchant that allows those services to be paid for with PIN-enabled debit cards.

The problem with this approach is that while it's likely to be the cheapest in out-of-pocket cost, it's likely to be the most expensive in opportunity cost, because the same trips could be used to liquidate higher-denomination (and more profitable) PIN-enabled debit cards instead. This is the issue I've referred to in the past as "liquidation bandwidth."

If your local merchants don't throttle payments, that may not be an issue for you: you can liquidate these tiny-denomination cards side-by-side with higher-denomination cards. But if you're limited to 4 debit card swipes, or a single swipe, then you'll likely be better off swiping a higher-denomination, rather than lower-denomination, card.

Pay up

It's not nearly as sexy as loading up a Starbucks card or settling a decade's worth of car insurance payments, but there are also ways to simply pay to liquidate small-denomination debit cards. You can pay many kinds of bills online using Plastiq at a cost of 2.5% (61 cents on a $24.39 payment).

If you enroll using my personal referral link you also earn "Fee-free dollars" which allow you to make eligible bill payments without paying any fees at all — I get 400 fee-free dollars (16 $25 cards!) and you get 200 fee-free dollars (8 $25 cards!).

Plastiq has one key advantage over other bill payment services for liquidating these tiny-denomination cards: it doesn't have a minimum fee. When liquidating high-denomination cards the objective is to have a low, flat fee. That's one reason online quarterly tax payments are popular — at least among self-employed bloggers who have to make online quarterly tax payments anyway!

On the other hand, when liquidating low- or tiny-denomination cards, it's much preferable to have a fixed percentage fee no matter how high it is.

Conclusion

The good news is that 5% Back gift cards are capable of producing almost pure profit, no matter how much you have to pay to liquidate their residual balances.

The bad news is that once you have a stack of cards with residual balances, you really should put in a little bit of time to figure out the cheapest, most efficient way of liquidating those balances back to cold hard cash.

My experience with free 5% Back Visa Simon Giftcards

A number of bloggers have mentioned some current promotions going on related to 5% Back Visa gift cards. One potential money-making approach is to buy $500 cards through GiftCardMall for $480.95 each. That is unfortunately limited by GiftCardMall's frequent and inexplicable flagging of large gift card orders.

Another current opportunity is purchasing 5% Back Visa Simon Giftcards in-person at Simon Malls locations. The cards are currently being sold with no activation fees at many, if not most, Simon Malls in the United States.

My local mall finally restocked today, so I headed down to find out whatever I could.

5% Back Visa Simon Giftcards really are free this week

You never know when this kind of promotion comes around what kind of limits or restrictions will be placed on purchases. At my Simon Mall, the guest services manager was happy to ring up my order exactly as usual, while waiving the activation fee. Most Simon Malls limit gift card purchases to a total order amount of $10,000, including activation fees. Since activation fees are waived I assume that means you would be able to purchase twenty 5% Back Visa Simon Giftcards for a total of $10,000.

The promotion runs through Sunday, December 11, 2016.

5% Back Visa Simon Giftcards are PIN-enabled as usual

The Visa gift cards sold at Simon Malls are issued by Metabank, with a default PIN of the last four digits of the card number. 5% Back Visa Simon Giftcards are no exception, and are fully functional Metabank PIN-enabled debit cards. My firm expectation is that merchants which don't accept Metabank PIN-enabled debit cards will not accept these either.

Debit purchases at CVS don't require the last four digits of the card number

There are a lot of CVS store locations in the United States. While the CVS point-of-sale terminals do not instruct cashiers to compare customers' identification with the name on their credit card, there are no doubt particular cashiers who, out of an abundance of caution, will try to compare the name on your card with the name on your identification documents.

However, when making a PIN-based purchase at CVS, the system does not prompt cashiers to enter the last four digits of the debit card's number, so there's no occasion for them to notice that your debit card doesn't have any name embossed on it, let alone your name.

Conclusion

I'm sure most of my readers with convenient access to Simon Mall locations have already begun experimenting with these cards, so won't find anything too groundbreaking here. On the other hand if you've been waiting to dive in until you were more confident that 5% Back Visa Simon Giftcards were as easy to liquidate as whichever products you're currently using, I hope this post is reassuring.

Even if you don't take advantage of the 5% Back feature of these cards (which can be cumbersome), this deal is just about as close to free as manufactured spend gets these days, and I have every intention of making the most of it.

"The Black Swan" is not a very good book

This is a review of "The Black Swan" by Nassim Nicholas Taleb. You can find all my previous book reviews here. If you're interested in buying a copy, I hope you'll consider using my Amazon Associates referral link.

"The Black Swan" captured the imagination of the reading, writing, and investing public the moment it was published in 2007, and sprang to even greater prominence as the global financial crisis ran its course over the following years. While I'd been looking forward to reading the book for some time, last month I finally found the time to plow through it.

I was disappointed.

"The Black Swan" is a book about one interesting and true observation

Taleb has one main point, which he approaches from a variety of angles: the impulse to apply Gaussian (bell curve) statistical distribution models to real-world phenomena is based on the ease of applying them, and not on their accuracy in describing those phenomena.

I took introductory statistics in college, and in my experience this is precisely correct: introductory statistics professors teach statistics as if the goal of the science is to acquire a large enough sample to discover the correct Gaussian distribution. If your sample doesn't follow a bell curve distribution, then you need to collect more samples until you discover the true, underlying bell curve.

Taleb argues convincingly that there is no reason to believe "social" phenomena have bell curve distributions. Wealth and income are not physical phenomena which become increasingly rare the further you move from the average; on the contrary, an arbitrarily large amount of income or wealth can be concentrated among an arbitrarily small number of people.

Nassim Taleb is not entirely hinged

Once you realize that Gaussian distributions are not entirely, or even not particularly, applicable to the real world, then it's natural to draw unusual conclusions.

If stock market performance is random but not Gaussian then "unusually" large stock market moves will occur far more often than would be predicted by models based on the bell curve (see: 2000 and 2008).

If success in business is random but not Gaussian then risky bets will produce extreme wins and losses more often than a bell curve would predict, so exposing yourself to those extreme wins while protecting yourself from extreme losses (Taleb's so-called "barbell" approach) will produce higher returns than a consistently mediocre portfolio.

Unfortunately, Nassim Taleb does not confine himself to his area of obvious expertise: trying to profit from large advantageous market moves while protecting himself from large, irrecoverable losses.

Taleb thinks black swans are everywhere

Taleb accidentally makes an interesting point about the difference between predicting the behavior of individual subatomic particles (completely impossible) and predicting the behavior of large grouping of subatomic particles, i.e., physical objects. He asks why, if his coffee mug is composed of subatomic particles moving in unpredictable ways, his mug doesn't leap off the desk into the air. The answer, of course, is that subatomic particles in large groups behave according to extremely predictable rules. Mugs don't jump off desks.

What Taleb gets wrong is that more human institutions are like coffee mugs than like subatomic particles.

For example, in chapter 11 Taleb advances his idea of "academic libertarianism:"

"[T]he problem with organized knowledge is that there is an occasional divergence of interests between academic guilds and knowledge itself. So I cannot for the life of me understand why today's libertarians do not go after tenured faculty (except perhaps because many libertarians are academics). We saw that companies can go bust, while governments remain. But while governments remain, civil servants can be demoted and congressmen and senators can be eventually voted out of office. In academia a tenured faculty is permanent — the business of knowledge has permanent 'owners.' Simply, the charlatan is more the product of control than the result of freedom and lack of structure."

Academia, of course, is an educational system much more like a coffee mug than a subatomic particle: the objective of higher education is to educate at a level as consistently high as possible. When people don't have control over the quality of education they receive, making it as consistent as possible is a perfectly reasonable goal.

Taleb has nothing to say about the large, functional systems we depend on

The subtitle of Taleb's book is "the impact of the highly improbable." The tendency since the book's release is to refer to any unforeseen event as a "black swan." This tendency is largely Taleb's fault, because while he has since become extremely protective of the term, in the actual text of the book it's barely defined at all. Taleb says a black swan must be "rare, impactful, and predictable in retrospect but not prospectively."

What event does that not apply to?

The fact is that vast majority of the systems actual people rely on are extremely resilient against "black swans," and virtually impossible to "hedge" against the failure of.

  • Social Security is a system virtually all American workers pay into and which pays out checks to the retired and disabled.
  • Medicare is a system virtually all American workers pay into and which pays out checks to doctors, hospitals, and pharmacies.
  • The Department of Education's Direct Loan Program collects information on students and disburses funds to their institutions of higher education.

We can break these systems by electing politicians dedicated to destroying them. But that is not a "black swan," that's the unfortunate outcome of a process of collective decision making.

Conclusion

The solution to Gaussian, bell curve fantasies is not this sprawling 400-page tome of artistic criticism and intellectual wankery. It's reality.

Don't take out an interest-only mortgage with a teaser rate and balloon payment — the domestic housing market isn't Gaussian.

Don't invest money you can't afford to lose in a single car company, bank, or oil company — disasters are unpredictable.

And don't ask more out of your investments than they're capable of giving you. Buying a low-cost total stock market mutual fund from Vanguard will give you exposure to the total stock market. Buying a bond fund will give you a stream of income. Buying a bunch of Beanie Babies will give you exposure to the 90's hobbyist market.

But there's no added value to thinking of a collapse in the US stock market, a rise in interest rates, and people realizing Beanie Babies aren't worth anything as "black swans," outside "the normal distribution." They're all guaranteed to happen eventually.

Trying to develop resilience against these events is worthwhile, but doesn't require any additional intellectual framework beyond:

  1. Don't risk more than you can afford to lose;
  2. Don't take risks you don't understand;
  3. Diversify what you can afford to lose among risks you understand.

Gut-checking the latest and greatest opportunities

Starting today, it should in principle be possible to sign up for the Popular Credit Service Avianca LifeMiles credit cards. Signup bonuses are constantly fluctuating up and down, but it's not every day that we get a brand new credit card to evaluate. With that in mind I thought I'd share my simple framework for looking at new offers like this when they come around.

What do I already know, and what do I need to know?

A quick glance at my airline alliances page shows that Avianca is a Star Alliance member. I already know that I hate flying United, so Avianca won't be useful for domestic itineraries, but it might be useful for international itineraries.

On Star Alliance partner airlines, there are no obvious sweet spots. Economy awards to Europe, for example on Lufthansa or Turkish Airways, cost 60,000 LifeMiles roundtrip, the same as United MileagePlus miles. In Business class on a Star Alliance partner you'll pay 126,000 LifeMiles roundtrip, somewhat better than the 140,000 MileagePlus miles United would charge.

To North Asia, LifeMiles will charge the same 70,000 miles roundtrip as United, but 10,000 miles fewer (150,000 LifeMiles versus 160,000 MileagePlus miles) for Business class. So in terms of redemption value, LifeMiles are certainly competitive with MileagePlus miles for travel on Star Alliance partners.

This is the sort of simple calculation you can glance at to anchor the valuation of a new currency compared to ones you're already familiar with. LifeMiles seem to be a pretty good Star Alliance rewards currency, at least competitive with MileagePlus miles.

Do I have a redemption plan?

Some readers seem to think that I'm some kind of maniac who insists there's no point in earning a mile you don't already have budgeted for a specific trip, on a specific flight, on a specific day, with a specific co-pilot leaving from a specific gate.

That's baloney! All I've ever said is that the least valuable point is the one you don't redeem, and that the point of travel hacking is to pay as little as possible for the trips you want to take.

If the trip you want to take is "Lufthansa First class to Europe," then having a slew of reasonably-priced Star Alliance miles lying around is a natural solution — a perfect solution! On the other hand, if the trip you want to take is "summer in Europe" then you may well have been better off waiting for a fare sale like the ones we saw last week where roundtrip economy fares were in the low 3-figures.

Knowing the kinds of trips you're likely to take, whether you're likely to pay for them with cash or with miles and points, and knowing which miles and points are well-suited for the job is a simple way of calibrating whether a brand new deal is spectacular or a dud.

Is it scalable?

There are two kinds of offers: one-of-a-kind opportunities like a 100,000-point signup bonus from a bank with good risk controls, and opportunities with potentially unlimited upside. Into the second category fall things like churnable credit cards, unappreciated reselling opportunities, or gift card liquidation mechanisms no one else has thought of.

A scalable opportunity is worth more than a one-off opportunity because once the background research has been done each iteration produces close to pure profit for as long as the deal lasts.

For example, while the US Bank Club Carlson credit cards offered the last night free on award stays, there was no limit to the number of 2-night stays you could book at half price. Along with a partner you could book any integer multiple of 2 nights at a top-tier 70,000-point property for 35,000 points per night, or $7,000 in otherwise-unbonused credit card spend per night.

In the case of the Avianca Vuela credit card, which is supposed to offer 2 LifeMiles per dollar spent at gas stations and grocery stores, the question is whether you'll be willing to earn 2 LifeMiles per dollar at the expense of other rewards currencies. There's no obvious answer to that question — it'll depend on your own circumstances. At grocery stores, 2 LifeMiles per dollar spent may be worth more than 6 HHonors points, or more than 2 Flexpoints, or more than 2 Membership Rewards points, or it may not.

In short: a lucrative bonus category can turn a so-so credit card, or a decent signup bonus, into a scalable opportunity — but whether it does or not will depend on your own circumstances.

What will I do with the remaining points?

After signing up for a Avianca Vuela card, and meeting the spending requirement, you'll be the proud owner of 60,000 LifeMiles. Say you jump on a 50,000-LifeMile First class award from North America to Hawaii. Now you're the proud owner of 10,000 LifeMiles.

You can either accept that you got a 50,000-mile signup bonus, instead of a 60,000-mile one, or you can start conniving and contriving to redeem your remaining 10,000 LifeMiles, or start doing your utmost to earn more until you get to another redemption threshold.

I don't give advice, and don't care which response you have.

But knowing which response you're likely to have before you get there is a key to long-term mental health and regret-minimization in this game.

Conclusion

Let me stress again that there's no reason that "maximizing" the cash value you get from each travel hacking technique should be the only goal of your practice. But it does provide a general framework that at least lets you calculate, within general parameters, what the tradeoff is between fixed-value and flexible rewards points, between hotel points and airline miles, and between manufactured spend and signup bonuses.

Shutdowns, devaluations, and resiliency

One travel hacking blogger who never disappoints is Vinh at Miles per Day (his Twitter account is a must-follow as well). Vinh attracts shutdowns like an office supply store promotion attracts Ink Plus cards. He's been shutdown by PayPal, eBay, Best Buy (huh?), Chase, and that's just in the last two months.

On the other hand, Vinh is incredibly resilient, judging by the fact that he seems to buy a new car every 6 months or so.

That got me thinking about different ways to approach shutdowns and devaluations. In other words, how to become as resilient as Vinh.

Shutdowns are another kind of devaluation

If, like me, you think the point of travel hacking is to pay as little as possible for the trips you want to take, then there's no conceptual difference between a shutdown and a devaluation.

When American Express Membership Rewards points changed their transfer ratio to British Airways Avios from 1000:1000 to 1000:800 in October, 2015, that was a 20% devaluation. If you have both a flexible Chase Ultimate Rewards account and a Membership Rewards account, losing the Ultimate Rewards account with its 1000:1000 transfer ratio is also a 20% devaluation, since you'll have to pay 25% more Membership Rewards points than you previously paid in Ultimate Rewards points.

You can adjust the numbers depending on how you value Ultimate Rewards points relative to Membership Rewards points, but the point is that an account closure makes trips more expensive, just like a change to an award chart or the elimination of a credit card bonus category does.

I don't think there's any one right answer to how to think about shutdowns and devaluations, but here are three different approaches, each of which suggests a different way to build a travel hacking practice.

Approach #1: Pretend you're safe

This is by far the most popular approach advocated on mainstream blogs and in fact practiced by many travel hackers. When someone tells you to buy American AAdvantage miles at their lowest price ever, they're not just telling you the price you can buy them at, they're also telling you to pretend they'll maintain their value until you redeem them, or at least to factor in only a small risk of a short-term devaluation.

Likewise when someone tells you to earn Ultimate Rewards points "because they're so valuable," they're also implicitly telling you "and ignore the risk of your Chase accounts being shutdown and you being forced to liquidate your points on 30 days' notice."

There's nothing inherently wrong with this approach, as long as you know that's what you're doing. Acting as if you're safe from devaluations and shutdowns would lend itself towards running up big balances in just a few programs where you get the most value. Someone pretending they're safe might use just two or three credit cards issued by a single bank.

A combination of a Chase Freedom Unlimited, Chase Ink Plus, and Chase Sapphire Reserve would give you easy access to bonused spend with the Ink Plus, unbonused spend with the Freedom Unlimited, and high-value redemptions with the Sapphire Reserve, all without setting foot outside of Chase's ecosystem.

After those cards are closed and your Ultimate Rewards points have been liquidated, you could switch to an American Express Business Platinum card combined with an Amex EveryDay Preferred and/or Preferred Rewards Gold card.

The point is that pretending you're safe creates a permission structure to focus as heavily as possible on the very most valuable rewards currencies. Ironically, this approach of ignoring the risks of shutdown and devaluations is best suited for someone who is convinced that travel hacking is dying as a hobby!

The reason is obvious: the more certain you are that travel hacking will no longer be possible in the near future, the less you have to lose by risking shutdown, and therefore the more value you can extract from the most valuable programs by ignoring the risk of shutdown and devaluation.

Approach #2: Equal-weight the value of your rewards

Another approach might be to admit that there is an unknown risk of shutdown and devaluation across all your rewards currencies. If the risk were known, you would be able to weight your earning rates by value and risk: if Delta SkyMiles were twice as valuable as United Mileage Plus miles today, but were certain to be worth half as much a year from today, you could earn and burn them in the precise ratio such that your remaining, post-devaluation balances have the same value in one year.

Since the risk of shutdown and devaluation is unknown, you can't make that precise calculation. Instead, you can assume that more valuable currencies are more likely to devalue than less valuable ones, and more lucrative credit cards are more likely to shutdown heavy hitters than less lucrative ones.

This approach lends itself to the counterintuitive practice of earning fewer of more valuable rewards and more of less valuable rewards. If one card earns 5% cash back and another earns 2% cash back, you could earn 2.5 times more rewards on the second, less-lucrative card. This would theoretically raise the risk of shutdown on the less-lucrative card (which would hurt less to lose) and lower the risk of shutdown on the more-lucrative card (which would hurt more to lose).

While it sounds slightly bizarre when I frame it this way, a version of this approach is actually practiced by those of my readers who leave comments on my posts about manufacturing spend with a Chase Ink Plus card. They'll frequently say, "I value my relationship with Chase too much to manufacture spend aggressively on my Ink cards." In other words, the more valuable they find a rewards program, the less risk of a shutdown they're willing to run.

Approach #3: Set earning and burning goals, and change course as necessary

If you asked a representative sample of travel hackers, I suspect a slight plurality would say this is their general approach to the game: combine a broad awareness of as many opportunities as possible with a realistic view of your own travel goals and time constraints, and do your best to earn and burn the "right" miles and points.

When framed this way, the approach has a lot to recommend it: by earning the miles and points you need for the trips you want to take, you can keep your balances low enough that you're unlikely to be devastated by a single shutdown or devaluation. There's no way to "protect" yourself from an overnight devaluation like the one inflicted on Emirates awards booked with Alaska Airlines Mileage Plan miles back in March, 2016, but under most circumstances if you restrict yourself to planning 6-12 months in advance, you're likely to be able to redeem your miles under roughly the same terms as you earned them.

While this is certainly the approach I take, it's also far more difficult to implement successfully than the previous two approaches. We call rewards currencies "loyalty programs" because they are designed to cloud precisely the judgment needed to make good decisions about them. While devaluations reduce the value of your rewards currencies for future redemptions, months or years in the future, they don't affect the value of rewards you've already redeemed — and you're more likely to judge a program based on your past success using it than prospectively based on its current and future earning and redemption structure.

The annual free night certificates offered by hotel credit cards are a great example of this. The Marriott Rewards Premier credit card currently has an 80,000-point signup bonus. Even in Marriott's miserly program, that's enough for 2 nights at a Category 8 property. After the first year, you receive a free night certificate good at a Category 1-5 property. During that second year you may find a Category 5 property that fits your needs, and still feel like you're getting a good value for your $85 annual fee. Now your third year rolls around and your annual fee is due: you're likely to look at your past success redeeming your free night certificate than look at your future plans when deciding whether to pay the annual fee or not. And as more and more properties migrate up and out of Category 5, you'll find it harder and harder to use that free night certificate each year.

The point here is simple: it's not enough to draw up a strategy to earn and burn the points you need for the trips you want to take. To use this approach successfully you also have to periodically revisit your plans and programs to decide whether the techniques you're using still offer the straightest path towards your goals, or whether it's time to add a new program, cut out an old program, or change your strategy entirely.

Conclusion

Every travel hacking practice is ultimately a hybrid of calculation, opportunism, and habit. My own relentless focus is on those currencies I'm most likely to redeem as soon as possible. I start with cash back, then build on that with fixed value currencies like US Bank Flexpoints and Ultimate Rewards points, then add Delta and Hilton points thanks to their combination of accelerated earning and ease of redemptions — Delta SkyMiles and Hilton HHonors points are both relatively easy to redeem as long as you are willing to redeem them at "break even" rates instead of swinging for the fences with each redemption.

For example, an upcoming Hilton redemption over the holidays yielded 0.5 cents per point — nothing out of this world, but the equivalent of 3% cash back on my grocery store manufactured spend, and 57% off retail, after accounting for fees.

But my strategy only works for me because I'm willing to keep my rewards balances as low as possible. If you're the kind of person who likes seeing 7 or 8 digits in their loyalty accounts, you may want to consider figuring out whether you actually have a travel hacking strategy at all.

Why I'm gunning for Globalist

After I wrote last month that Hyatt's new loyalty program "made the decision easy" to requalify as a Hyatt Gold Passport Diamond in 2016, Joe Cheung at As the Joe Flies suggested it might be useful to explain my thinking in more detail.

The fact is, I take a pretty brute force approach to travel hacking, so the calculus for me is equally straightforward: I calculate my projected benefits, subtract my projected costs, and figure out whether I'll come out ahead or not. I'm happy to spell that calculus out in more detail.

The cash value of 2017 Diamond status

There are exactly three benefits of the World of Hyatt program which have any concrete value to me:

  • A free night at any Category 1-7 property worldwide. This is worth up to $300, the cash value of 30,000 Ultimate Rewards points transferred to Hyatt Gold Passport or World of Hyatt.
  • Breakfast and club access. This is worth perhaps $20-30 per night stayed at Hyatt properties between March 1, 2017, and February 28, 2018.
  • 4 confirmed suite upgrades, subject to availability. This is worth perhaps $100 total — suites are nice, while being subject to availability sucks.

In other words, given a minimum of 4 Hyatt stays in the 2017 membership year, Hyatt Gold Passport Diamond status requalification can be assigned a starting value of $480: $300 in transferred Ultimate Rewards points, $80 in breakfast, and another $100 in suite upgrades.

The cash cost of 2017 Diamond status

After meeting the $40,000 spend threshold on my Chase Hyatt credit card, and earning a total of 5 elite-qualifying stay credits, I'll be 5 stays away from requalifying for Diamond status in 2016. Earning those 5 elite-qualifying stay credits only needs to cost me $96 per stay to "break even" with my projected value of Globalist elite status

I'm always anxious to remind people that "breaking even" isn't the point of travel hacking: we're supposed to come out so far ahead that all the crazy antics we commit ourselves to end up paying for themselves! If spending $480 in cash only got me $480 in value, there'd be no point in using Hyatt Gold Passport as an intermediary — I'd just pay $480 for things I valued at $480.

I can, in fact, achieve my remaining 5 elite-qualifying stays for a total price of $455. Putting those charges, at Hyatt Regency properties, on my Chase Hyatt credit card will reduce the price by another $50. One of these "mattress runs" will trigger another 10,000 Hyatt Gold Passport-point payout from the current "More Points. More Play." promotion, and all 5 will trigger 500-point payouts from the current mobile-booking promotion. Earning 6.5 points per dollar adds up to another 2,600 points on the room charges, plus up to 5,000 more points if I choose the points amenity on all 5 stays.

Valuing those earned points at their cash opportunity cost to me — one cent each — means I can pay $204 for $480 in value. That puts me squarely in the range of savings that travel hackers should take seriously.

This calculation requires no fantasies

If you're paying attention, the value I place on Hyatt Gold Passport Diamond status and World of Hyatt Globalist status requires just four stays of one night each in the 2017 membership year.

If I stay four separate nights, and apply four suite upgrade awards, and a single one of my nights is at a Category 7 property, I'm certain to get $480 in value.

I plan to get much, much more value from Globalist status in 2017. The key point is that the more realistic your assessment of the value of elite status, the easier it is to calculate the return on your travel hacking investment.