Impressed by first MaxMyPoint hotel award alerts

A few weeks ago I read a post comparing various hotel award alert tools that concluded MaxMyPoint was the only one that did the job (since the internet is no longer searchable I can no longer find that post; if you wrote it, let me know and I’ll link to it!).

Years ago I used and recommended Seth Miller’s Hotel Hustle to find award availability optimized by point value, but the functionality of that tool died before too long and we were back to searching for award space manually.

Fortunately for me, I actually had a very specific need for an award alert, and to my shock, MaxMyPoint met it perfectly and saved me a few hundred dollars by swapping my paid reservations for award nights.

Two missing nights in Prague

The last time I visited Prague, World of Hyatt had finally secured a property in the city: the Lindner Hotel Prague Castle. To my genuine surprise and delight, it was a Category 1 property, costing between 3,500 and 6,500 points per night.

Compare this to the other obvious properties in Prague. The Hilton Prague and Hilton Prague Old Town, both great hotels I’ve stayed at many times, have standard pricing between 40,000 and 50,000 Hilton Honors points, or roughly $200-250 in value. The three centrally-located Marriott properties all cost 33,000 points and up. IHG starts in the same range: they’re non-starters.

So Hyatt giving away nights for $65 was pretty exciting. The property is located in the heart of Hřadčany flush up against Prague Castle, so while it is in a tourist area, it’s not actually an area where most tourists stay, which makes it remarkably quiet in the evening once they decamp to their hotels in the city center.

I had a simple problem: my first, third, and fifth nights were available on points, my second night was available with cash and points (for a premium room), and my fourth night was only available with cash. So that’s how I booked it: five reservations for five nights.

Then I set a MaxMyPoint alert for the entire 5-night stay, on May 17.

On May 27 at 3:22 am, I got my first alert (subject line “Your Hotel Alert Update”) saying the nights were available. Perhaps because the alert came while I was asleep, by the time I checked availability it was no longer there, if it had ever been.

On June 4, at the perfectly sensible hour of 12:08 pm, I got my second alert. This time, awake as I was, I immediately popped over to the Hyatt app and saw the alert was correct: all five nights were available. I canceled my existing 5 reservations (technically risky, but I didn’t want to transfer over another 26,500 Ultimate Rewards points if I didn’t have to) and was able to successfully complete the reservation.

Then, as if icing on the cake, MaxMyPoint sent another alert at 8:32 pm that the award space was no longer available, a charming free reminder that they had done their job for me.

Conclusion

As indicated by the history of Hotel Hustle, it’s not a great idea to let your own skill and intuition atrophy every time new tools come along to replace them, because that puts you at the mercy of the toolmaker. But it’s equally foolish to ignore when tools are introduced that you can integrate into your workflow to make your life easier, and MaxMyPoint gave me the information I needed just in time to take advantage of it. Kudos to them, and I’ll be a repeat (non-paying) customer as long as they keep it up.

Venti reads my blog and makes some big, immediate improvements

Back in February I wrote about Venti, a very-high-interest savings account with a gimmicky twist: the “interest” on your savings is credited to a separate “points” balance that can only be redeemed for travel through the Venti flight and hotel shopping portals.

Since I’m one of the biggest Venti deposit-holders, it’s perhaps unsurprising they stumbled over that blog post and held a few team meetings about solutions to some of the problems I identified (from an e-mail: “We understand that you’ve been quite critical of Venti in the past through your blog. However, it would be a mistake on our end not to learn from you how to improve”).

I politely disagree with them that I was “quite critical” (they should read what I say about Gary Leff) but I’m glad to see they’ve already annouced three big improvements for existing customers and a few unannounced changes for those who have not joined.

I’ll break down the three announced changes in the order they were listed in the announcement.

“Increased Points Redemption”

Here’s the first change:

“The number one request was to allow for more Points to be used per transaction. Venti is not currently supported by outside funding/venture capital (despite some assuming so). Thus, limitations are in place until we accomplish certain milestones. As of this email, any flight under $250 can be booked solely with Points. All other flights have a flat $250 off MSRP. Hotel orders under $120 remain fully bookable with Points. In the future, you can expect the redemption ratios to improve significantly as we grow and onboard more members.”

This is terrific. It means you can spend down your points balance (the part that’s locked into Venti’s reservation ecosystem) first, before having to spend any of your cash balance (the part that can be moved in and out of other banks).

Right now that only applies up to $250, but the point is, it’s the first $250 of each reservation. For airlines that price all flights as one-ways, you can book each leg as a separate ticket to spend down your point balance $250 at a time. This crystallizes the value proposition I identified in my original post: “Venti is a way to earn above-market interest on your savings if you sometimes pay cash for airfare.”

“Updated Points Disbursement Schedule”

Here’s the second announced change:

“The current model heavily favors wealthier members who often begin their Venti experience with thousands in deposit. For the average member, it takes too long to accumulate Points at a rate that unlocks free travel. Starting June 1, we're changing Points disbursement to weekly instead of Monthly. Our rewards APY will remain at 9% for all paid membership tiers for 2024. Buddy Pass holders cannot deposit funds.”

This is phrased a little confusingly but you can understand the general point: the more frequently they award points, the more likely smaller-deposit accounts will be to get redeemable quantities of points. Smaller, more frequent redemptions are more likely to keep smaller depositers invested in the program, since they won’t have to wait months or years to get enough points to redeem for a domestic flight or a single hotel night.

Since one of my primary concerns is with the viability of the company as a whole, my personal feeling is that this also gives larger depositors confidence that their weekly points disbursement reflects their running balance. If the number suddenly jumps or drops or skips a week, then it will be an early clue that all is not right in Venti-land.

“Allowing Credit Cards”

The third announced change is arguably a bigger deal than either of those:

“The greatest area of friction within our product was only allowing flights and hotels to be booked with cash savings (and Points) from your Boarding Pass. Our goal was to avoid credit card processing fees since Venti does not profit from the sale of flights. In June, we'll enable credit card payment options for all membership tiers, including Buddy Pass. You will be able to use Venti Points along with your favorite credit card at checkout for flights and hotels.”

In principle, if you pay your credit card balance in full each month, then you should be almost indifferent between paying with your Venti cash balance or a credit card. In reality, one of the things we pay for on many annual-fee credit cards is travel benefits that are triggered by paying for airline tickets (and rental cars) with that particular card. Most trips don’t have qualifying events (like missed connections or late or lost baggage), and most people who suffer qualifying events never claim the benefit, but being unable to pay for flights with credit cards meant that no Venti flights were eligible for them at all.

I believe as long as you keep good enough records to connect the Venti reservation to the credit card charge, you should now be eligible for those benefits as long as you charge at least $1 of your airfare to the credit card.

Unannounced positive changes

While I was fooling around on their website, I noticed Venti had made a few more changes I had not seen them previously announce.

The “Priority” tier, which was previously listed at $72 per year and earning 5% APY (in points) on up to $15,000 has been slimmed down: it now has no annual fee but earns 9% APY on up to $7,500 in cash deposits.

The “First Class” tier is still listed at $500 per year (remember that I signed up when the First Class price was just $9.99), but now offers 9% APY on up to $250,000 in deposits, up from $100,000.

These are both positive changes. Early adopters like me can decide next year whether to switch over to Priority and keep $7,500 in the account trundling along earning 9% APY (compounding discipline requires constantly finding new places to stash your compounded returns), while heavy hitters can stuff $250,000 into First Class accounts and earn (after the $500 annual fee) roughly 8.8% APY and cover $22,000 in paid travel per year.

The “Business Class” tier appears to never have been actually launched and isn’t available on the website for signup, so no great win or loss to report there.

"How do we scale this?"

One of my favorite questions travel hackers ask is “how do we scale this?” The implicit answer is, usually, “we don’t.” Contrary to what economists pretend to believe, the world is in fact chock-full of arbitrage opportunities. What is true is that most of those opportunities are difficult or impossible to scale.

Here’s my personal breakdown of techniques used to increase scale, and the obstacles to doing so.

Brute force and constant returns to scale

The most obvious scaling strategy is to multiply your own effort. If you have a technique that generates a known amount of value per hour you spend on it, then you can get twice as much value by spending twice as much time, usually up to some limit. In a simple example, if it takes you an hour to manufacture $10,000 in in-person spend at one grocery store, and you have identical access to five grocery stores, then you can spend 5 hours and manufacture $50,000.

Automation and transformations

A lot of high-volume travel hackers focus on automation as a way to scale their techniques, and automation is one of the many tools I put in the broad category of “transformations.” Transformations are when the design of programs can be understood differently by the customer than by the business in order to scale techniques, either to get a higher return from the same amount of time or money, or to reduce the time or money needed to get the maximum return.

To give a classic example from my own practice, for many years the US Bank Flexperks Travel Rewards Visa offered 3 points per dollar spent on charity, worth up to 6% when redeemed through their travel portal. They also coded Kiva, the microlending website, as charity. People were thus able to earn as much as 6% in travel on loans of as little as a few months, and many of us did, transforming a modest discount on charitable giving into an extremely high-yield investment vehicle.

A more contemporary example is the rewards (often branded as “Kasasa”) checking accounts that offer some of the highest-earning, most liquid savings vehicles. They typically require 12-15 debit card transactions along with a direct deposit in order to earn their advertised rates. Meeting these requirements as they intend would seem to require, as they intend, reorienting your entire financial life around doing so. But when you’ve broken down the requirements to their individual parts, you can transform meeting them into a matter of a few minutes per month.

American Express cards have acquired a reputation of being “coupon books,” but a lot of the pain of redeeming those coupons (and getting back the value of your annual fee) can be transformed into painless routines:

All these are transformations: the company wants them to dominate your thoughts, but a few simple calendar reminders can guarantee you maximize the value of each credit without having to keep track of any of them individually.

Teammates, comparative advantage, and the benefits of trade

I call teammates everyone you partner with in order to take advantage of different circumstances, what economists call your “comparative advantage.” These can take all sorts of forms: some people have access to grocery store manufactured spend while other people have access to gas stations. Some people have more Chase cards than they’ll ever be able to maximize the value of, while others pile into American Express cards and are blocked from signing up for new Chase cards.

A lot of bloggers have a kind of “view from nowhere,” where every person has access to every credit card and each can follow prescribed steps from scratch, but it takes almost no experience to know that’s absurd. Every individual travel hacker’s situation is different, and it takes only a little more experience to identify which parts of the game you’re interested in pursuing most intensively. Finding other people with complementary interests is a way to scale each of your efforts by getting the most value from the parts of the game you’re most interested in.

The most obvious candidates for teammates are family members, precisely because there’s usually not any need to “divide” effort or results at all: everyone gets to go on the family trip, regardless of whether they made a “fair” contribution to paying for it at all. Some bloggers have affected to call these teammates “Player 1,” “Player 2,” and so on.

Employees

One of the most common questions people ask when they find out about the existence of travel hacking is, “that sounds great, but I don’t want to do it, can I just pay you to do it for me?”

There are people and situations that make this possible, but fewer than people wish or expect. The main problem is that almost anything you can train people to do on your behalf, they can do on their own behalf. You are the middle man, and unless you have both knowledge and money that are impossible to steal, your employee will quickly get the drift and go to work for themself.

The Verge had a humorous story about this very phenomenon in my home state of Montana, where resellers would continuously set up drop-shipping warehouses only to find their employees, having mastered the skill of packing and unpacking Amazon shipments after a few months simply set up their own tax-free reselling businesses.

Readers as force-multipliers

Another way to scale a technique is simply to share it. This has all the advantages of the techniques above.

Brute force techniques will have more people applying more brute force and yielding more benefits.

If you know how to transform a technique from difficult to hard, then more people will save more time and effort.

If you know how to trade personal or regional advantages with other people, then telling them how will result in more benefits for everyone in those situations.

And if you tell people how to hire employees to solve their problems, then more people will have their problems solved and more people will be employed.

The problem, of course, is that you don’t get a cut. What’s up to you is how big of a problem that is.

Robinhood Gold versus Bank of America Preferred Rewards Platinum Honors

[To the reader: since I think a lot of people will be using affiliate links to sell this product, I’m not including any links, including my own referral links, in this post]

Robinhood, the online brokerage founded and aggressively marketed back when money was free, and which used that perch to make fee-free stock trading the new normal, recently announced a 3% cashback credit card, available only to its brokerage customers that pay for their “Gold” tier, which seems to currently cost $5.99 per month.

This is the rare product release which immediately had people in my real-world ambit asking, “have you seen this? What’s the catch?”

So I want to start by saying that there is no catch, and this is one of the best all-in-one financial products out there. Virtually everyone should sign up, once it’s widely available.

But that’s not especially interesting. What’s interesting is how it stacks up against the next-best product on the market: the Bank of America Preferred Rewards program, which has been the gold standard for cashback credit card rewards until now.

So, let’s take a look.

Robinhood Gold is a perfectly-designed all-in-one financial product

If you sign up for Robinhood Gold and get approved for their new credit card, then you earn 5% APY on your uninvested Robinhood balances and 3% cashback on all your credit card purchases.

Since Robinhood Gold is sold as a bundle, a lot of people are going to misunderstand that these are two entirely different products. The 5% APY offered on balances up to a million or so dollars of insured deposits (depending on how many FDIC partners they have any given week) is competitive, but it’s not best-in-class; Vanguard is paying 5.28% on uninvested cash in their own brokerage’s sweep account as of today.

Meanwhile, the 3% cashback offered by their new credit card, whenever it becomes available, is genuinely higher than any other product on the market.

So before we go further, let me repeat: most people are better off signing up for this bundle than they are doing anything else in the world of credit cards or banking.

Bank of America Preferred Rewards

It sounds funny to call such a bizarre program “simple,” but until the latest Robinhood announcement, the simplest, highest-earning cashback program has been Bank of America’s Preferred Rewards, which offers a 75% bonus on all the cashback earned on their own, non-co-branded credit cards. Since the highest unbonused earning on those cards is 1.5%, with Preferred Rewards those cards are usually said to earn 2.625% cashback on unbonused spend.

2.625% is lower than 3%, which means the new Robinhood product will earn higher rewards than one of the Bank of America cards on all unbonused spend.

Unlike paying for access to Robinhood Gold, qualifying for Preferred Rewards is an ordeal. I’m currently several months into the process of raising my average monthly balance until I qualify for their Platinum Preferred tier, upon which occasion I’ll transfer all the money back out until my next requalification period.

Breakeven points and resiliency

To calculate a breakeven point between Robinhood Gold and Bank of America Preferred Rewards, or any other cashback product, just divide the roughly $72 annual fee of Robinhood against the next best alternative.

A fee-free 2% cashback card, like the Citi Double Cash, is better for annual unbonused spend below $7,200: at that point the additional 1% paid by Robinhood matches the $72 cost of the membership.

Likewise, if you’re earning less than 5% APY on the funds held in your Bank of America accounts, or anywhere else, then you can consider the higher interest paid on your Robinhood balance to be “offsetting” the cost of the monthly fee.

This exercise is probably worth doing even if you don’t break even, for an unrelated reason: resiliency. I use resiliency to mean minimizing the downside when misfortune strikes. It’s much easier to shift between cards earning similar — although not identical! — rewards when one or more cards gets shut down. Shifting from a hotel card to an airline card to a cashback card is a much easier transition to make than shifting from rewards-earning credit cards to nothing.

Conclusion

For most people, under most circumstances, the Robinhood Gold proposition is airtight, for now. They should sign up, throw as much of their money as possible into their cash savings account, and use the card for all their purchases.

Whether an experienced travel hacker who has a range of similar cards earning similar value, or an experienced saver earning higher interest rates on the same balances, should do so is an exercise left for the reader.

Venti, the too-clever-by-half subscription savings account and travel booking platform

What if I told you there was a way to earn 9% APY on up to $100,000 of liquid and federally-insured cash deposits? I hope your first response would be “tell me more,” because by the end of this post you’ll be begging me to tell you less.

Introduction

The company is called Venti (my personal referral link; we both get either $10 or $20 in “points” after you make a deposit — the site gives conflicting information on this and much else), and at first glance, the conceit is simple: pay an initiation fee of $9.99, and then select one of two paid tiers (the website lists a third intermediate tier in some places but not in others, because the company and website are hilariously amateurish):

  • The “Priority” tier costs $72 per year ($8.99 the first year) and earns 5% APY on up to $15,000;

  • The “First Class” tier costs $504 per year ($9.99 the first year) and earns 9% APY on up to $100,000.

Obviously, since for the first year there’s only a $1 difference in price and a 4-percentage-point difference in APY, you should sign up for First Class for your first year.

The most important catch in this program is that the “interest” you earn is not credited to your cash balance, but instead to your “points” balance, which is recorded separately. Your cash balance never changes except when you make deposits, withdrawals, or purchases. However, your points balance is included in your total balance (“spending power”) when calculating each month’s interest, so you still enjoy the benefits of compound interest.

In fact, I believe in principle your total balance should continue to compound even after it exceeds $100,000, since that’s supposedly only the maximum cash balance, not total balance, in your account, but I can’t speak to that from experience.

Using points (spending your “interest”)

Of course, money is only worth what you can spend it on, so you’re not earning any interest at all until you redeem your points.

To this end, Venti has implemented the most primitive booking website in history. You can book two things with Venti: airplane tickets and hotel stays, and each has its own portal, interface, and backend. The airfare portal is better than the hotel portal, and I haven’t had any trouble finding results that match the routes and prices available on any normal travel portal.

Hotel bookings, which only became available this month, are still not working great. As far as I can tell they pulled a static list of hotel rates when the site when live, so a lot of the search “results” they return are no longer available. Presumably that will eventually get sorted out, but it’s hard to know since communications from Venti are pretty inscrutable, to the point where my guess is that English is not the first language of any of their marketing employees.

Once you find a flight or hotel you want to book, you’re given the option to pay with a combination of cash (from your cash balance) and points (from your points balance). Importantly, however, you are not given the option to pay with any combination of cash and points.

The catch

Venti limits the number of points you can redeem for reservations to a percentage of the total cost.

In some cases that percentage is almost 100%. For example, they are currently promoting that “For 2024, any hotel quote with a total order MSRP of $120 or less can be booked for under $1 with Points.” When they say “with Points” they’re trying to convey that they will allow you to spend up to $119 of your points balance, so that you’ll owe less than $1 out of your cash balance. But that $119 is your interest on your money: they’re pretending to do you a favor by letting you spend your own money!

You can click around the airline and hotel booking portals yourself to get a sense of what the maximum points component of various reservations is.

For airfares, I’ve seen maximum redemptions of 15% and 25%. Oddly, like the old US Bank Flexperks Travel Rewards card, the maximum redemption seems to be based on the price of the ticket, with 25% redemptions for flights in the lower hundreds and 15% redemptions on more expensive flights, meaning you could redeem $100 in points and $300 in cash for a $400 flight, or $150 in points and $850 in cash for a $1,000 flight.

For hotel stays, there also appear to be price bands, starting at 20% for stays under $500, and then further bands of 17.5%, 15%, and so on down to 5% for the most expensive stay I found: just $1,724 in points for a $34,472, 7-night stay at The Dominick Hotel in New York City. Note that these bands are applied to stays, not nights, so you have the option to get a higher usage rate if you stay under a band threshold by breaking longer stays into shorter, cheaper ones.

The way I think about this is that you are not “saving money” when you redeem points. Instead, you are trying to maximize the amount of interest you are spending and minimize the amount of capital you are spending, since you can withdraw your capital at any time but your interest is locked in their ecosystem and subject to their rules.

What’s really going on here?

It took me a while to figure out what was going through their minds when the Venti gang concocted this scheme, but I think I finally wrapped my head around it: Venti is selling access to commission-free rates, and taking your interest instead.

Consider a normal commissioned transaction. It could be an insurance policy instead of a hotel room, but let’s stick with travel for simplicity: a hotel is selling rooms for $100. But hotels are in the hospitality business, not the marketing business, so they announce they’ll pay $20 to anyone who sells one of their hotel rooms. Not wanting to undercut their own feeble marketing efforts, they further insist that they’ll only pay the $20 to people who sell their rooms for $100.

This gives every tout a $20 budget to spend on marketing hotel rooms, and as professionals, they can make $20 go a lot further than a harried hotel manager can. What a lot of them ended up doing was creating loyalty and rebate programs. In this stylized story, Hotels.com takes that $20 per night and gives $5 of it to their own members, or at least the ones who accumulate enough rewards to ever redeem them for anything. They give another $1 to cash back portals to drive more traffic to their site so they can collect more of those $20 bills. The cash back portals give $0.25 of their dollar to bloggers when people sign up with their affiliate links.

Consider another, parallel ecosystem in the banking industry: brokered accounts. Ordinary people, if they encounter these at all, see them in the form of mortgage brokers and those ads in the back pages of the newspaper for brokered CD’s. You can think of a brokered CD as having some “true” rate of interest the bank is willing to pay to brokers for collecting deposits, such that they’ll make the profit they expect when lending the money out. The broker can then pay depositors whatever interest rate they’re willing to accept, and collect the difference as their “commission.”

At Venti, they seem to have looked at these two ecosystems, added a weekend of cocaine and ecstasy, and finally had the audacity to ask, “why not both?”

Here’s my crude version of their business model.

  • Venti’s custodian, Veridian Credit Union, has some “true” underlying rate of interest they will pay anyone who collects money for them. If I had to guess, that rate is somewhere between 4% and 6%, but there are doubtless different tiers and bonuses that affect it as well. It is, in any case, nowhere near the 9% APY Venti promotes.

  • As indicated above, Venti also charges customers account initiation and annual fees.

  • Finally, Venti is paid a commission for selling flights and hotels through their crude booking portals. Remember, you can book flights and hotels using only your cash balance, without using any points at all, and on those transactions you pay full price and Venti collects the merchant’s full commission. Together, I think these three sources make up virtually all the company’s hypothetical revenue.

  • Next, Venti credits customers’ points balance with whatever interest rate they’ve paid for, while capping the number of points you can use at their commission rate, or a formula more or less approximating it. Since the commission is not a main or even important source of income, they can afford to be generous with these redemptions, like the $119 redemptions for $120 hotel stays. Even if $119 is slightly more than the commission they earn on the stay, they’ve still been earning interest on your money for all the months it took you to accumulate $119 in points.

We can quibble about the details later, but take as given for a moment that this is an extremely profitable business model: they are selling something that costs them nothing, while collecting interest on other people’s money. It’s a kind of charming inversion of the free money dynamic that powered the careers of so many idiots during the last decade. Now that money is expensive again, they’ve changed gears from spending to collecting as much of it as possible!

The problem with airfare

There’s an obvious reason why cashback portals don’t pay out on flight reservations: there’s no money in the commissions. Airlines aren’t like hotels or car rental agencies that are desperate to get the word out: they can afford marketing departments and they go to a lot of trouble to differentiate themselves. Whether you think airfare is or should be treated as an interchangeable commodity is beside the point: I do not believe airlines are going around paying 25% sales commissions on $500 flights.

I am sure that Venti is aware of this problem, and I am sure that they consider selling airline tickets as well as hotel rooms to be a necessary cost of doing business. No one would buy into this crazy ecosystem just to get very slightly discounted hotel rooms (eventually, maybe, if they leave their money long enough without Venti going bankrupt).

Their survival as a going concern, therefore, relies on a favorable balance between airline and hotel points redemptions: enough customers have to redeem their points for hotel stays, which cost Venti nothing, to make up for customers redeeming for flights, which Venti has to pay near-market rates for.

But Venti has no control over that ratio, and any heavy-handed attempt to push customers away from flights towards hotels will simply drive them and their money away.

And this is, indeed, the story of so many companies that blip into existence, trundle along uneventfully until travel hackers discover them, and are then wiped out in a few weeks or months of extreme usage.

Conclusion

I do not think Venti is long for this world, at least in its current form, but once you understand how it works, it does offer a pretty clear value proposition: you can earn 9% APY in value that can be redeemed for up to 25% of the cost of paid airfare.

That’s not earth-shattering, but earth-shattering is a high bar to hold a 21st century travel or finance start-up to. Notwithstanding the enthusiasm of affiliate bloggers, most of what we do isn’t earth-shattering. Venti is a way to earn above-market interest on your savings if you sometimes pay cash for airfare.

If all of your travel needs are already met with points and miles, then you certainly shouldn’t lock any money into their system, but a lot of us pay cash from time to time, particularly for the cheap domestic flights where Venti lets you spend down your points balance most aggressively. Since I have a First Class membership (these were free back in December, although I still had to pay the $8.99 initiation fee), I’ll probably leave a few thousand dollars in my account earning 9% APY and clean out my points balance every few months when I book domestic travel.

Successfully liquidating 3rd-party gift cards with CardCash

Gift card reselling is a manufactured spend technique that sees periodic surges in interest. At its base, it’s is as simple as any technique: buy gift cards at a big enough discount, or with enough of an earning bonus, and sell them at a small enough discount to make the points you walk away with worth the difference.

Players cycle in and out of this space with some regularity, and then are inevitably washed out by the inherent precarity of this line of business: a single batch of compromised gift cards can wipe out the usually-slim margins and cause an entire enterprise to tip into insolvency.

Revisiting CardCash

Checking back through my e-mail, it looks like I first used CardCash to liquidate Hewlett Packard gift cards back in 2016 when it was possible to generate unlimited points and cash by recycling them. I hadn’t used CardCash since, and while I didn’t remember having any problems with them back then, I didn’t even know if the site was still around.

Fortunately, it still is, and I was able to successfully use them to liquidate some Adidas gift cards I purchased during a recent promotion.

Bonus Safeway 4 U points on Adidas gift cards

Most weeks, the grocery stores around me run promotions for discounts or bonus points on gift card purchases. The promotions are usually for third-party gift cards, although last week Giant ran a formerly-common, now-rare promotion for bonus points on Visa prepaid debit cards.

Last week, Safeway ran a global promotion for 10 bonus Safeway for U points per dollar spent on Adidas gift cards. Since third-party gift cards usually earn one Safeway for U point per dollar, this meant you could earn 5500 points (55 Rewards) for each $500 Adidas gift card you purchased, plus any credit card rewards you earned on the purchase.

This was a nice combination of a big mainstream retailer (rather than a niche merchant like Top Golf) and a substantial bonus, so I decided to pencil out whether it made sense as a gift card reselling play.

Putting CardCash through its paces

Since it had been so long since I used CardCash, and the promotion lasted all week, I decided to run a few experiments before going all in. Fortunately, CardCash offers the same payout rate on all card denominations, so I first bought two $75 Adidas gift cards (the minimum to trigger the Safeway promotion), and submitted one to CardCash on Wednesday requesting a PayPal payout, and one on Thursday requesting an ACH payout. Both orders were immediately “confirmed” by e-mail, and both were “accepted” on Friday. I received the PayPal payment Friday afternoon and the ACH payment on Monday. The cash payout rate was identical at 80.5%, or $60.38.

With those experiments successfully completed, I was then confident enough to buy three more Adidas gift cards for $500 each.

Alternative redemption options

While CardCash will pay out cash, they also allow you to exchange third-party gift cards for other cards at a higher value. The highest redemption rate available was (and still is as of this writing) Hotels.com gift cards at $446.78, or 89.36% of face value.

I don’t have any special love for Hotels.com, but I do use them periodically when they have competitive rates or cancellation conditions for stays I don’t want to use points on. In fact, I have already booked two upcoming trips that added up to almost exactly the $1340.34 I’d get from swapping out Adidas gift cards. In my case, the Hotels.com gift cards were literally as good as cash to me.

Request for Proof of Purchase/Origin

I submitted my first two $500 cards on Friday and Sunday, and on Monday received an e-mail with the subject line “Request for Proof of Purchase/Origin” and the order number for my Friday order. The e-mail read:

“Thank you for choosing CardCash to sell your gift cards.

“To ensure secure transactions, please reply to this email with proof of purchase/origin for the gift cards you intend to sell. Please choose from the suggested examples or attach any other applicable documentation when replying to this email:

  1. “Purchase receipts or invoices with transaction details.

  2. “Documentation supporting their legitimacy, such as proof of employee incentives, loyalty rewards, or other valid sources.

  3. “Additional details or explanations that provide clarity on how the gift cards were obtained.

“Upon receiving the requested information, our team will review it promptly.

“Providing this information is crucial in maintaining our commitment to a safe and trustworthy platform.”

I e-mail a photo of the card packaging, the back of the gift card, and the Safeway receipt showing the purchase details a little before noon and a little before 1 pm I received both a polite e-mail back and two e-mails with links to my newly-minted Hotels.com gift cards.

My third order was accepted without any additional verification.

Doing the math

I value Safeway Rewards in volume at about $2.39 each. They are only worth this much in volume, because more expensive awards also give better value. A single Reward is worth at most a dollar or two, while 7 Rewards are worth around $19.50. The 55 Rewards earned on a $500 Adidas gift card were therefore worth about $131.45 to me.

Selling Adidas gift cards for 80.5% of face value ($402.50) would still be slightly profitable, especially if you have a particularly high-value redemption in mind. But if you value Hotels.com gift cards the same as cash, as I did, then the value proposition becomes much more attractive, as I paid just $53.22 for what I conservatively value at $131.45 in Alaska Airlines miles.

"Transfer" timeline for Just 4 U Alaska Airlines Mileage Plan redemptions

Last month I wrote about the option of redeeming Albertsons (and their subsidiaries) Just 4 U rewards for Alaska Airline Mileage Plan miles. The option of redeeming, for example, 7 Just 4 U rewards for 1,300 Mileage Plan miles instead of a $10 grocery reward is the functional equivalent of buying Mileage Plan miles for 0.77 cents each.

If you can generate (or have stockpiled; more on that below) more Just 4 U points than you can use for actual groceries, that's a perfectly sensible redemption, especially if you’re saving up miles for a premium award on one of Alaska’s partners.

My April Alaska Airlines redemptions posted in one batch on May 1

What I could not answer in that earlier post is how long it takes miles to appear in your Mileage Plan account after you’ve ordered a redemption. That’s because one or both of the programs backdates your miles to the date of the Just 4 U redemption, not the date they become available for Alaska Airlines awards.

In April I could see that I had placed an order for 100 Mileage Plan miles on January 27, and I could see 100 Mileage Plan miles dated January 27, but I could not see when the miles actually became available.

[Note: I say I could see the order “in April” because Just 4 U only shows your order history for 90 days, so when I wrote that post on April 6 I could still see my January 27 order, but I cannot see it in my Just 4 U order history any more.]

That being the case, over the course of April I made four additional Just 4 U redemptions, on the 6th, 14th, 19th, and 29th, and made it a point to check my Mileage Plan account every morning to see if anything had posted. That way, while I might not catch the exact moment the miles became available, I would know within a pretty narrow window.

That’s how I found out that all four of my Just 4 U redemptions (three for 100 miles and one for 250 miles) all posted on May 1, 2023.

Obviously one datapoint is neither dispositive nor permanent. For all I know they post miles every 45 days and May 1 just happened to be 45 days after the last batch posted in March. But that seems less likely than all of each month’s mile redemptions posting sometime on or around the first day of the following month.

There’s no point redeeming aggressively but there’s no point waiting

Batched posting like this means, on the one hand, you don’t need to immediately redeem each reward as you earn it (as a reminder, you earn one reward for every 100 points you earn in the Just 4 U program, and larger redemptions give better value) since if you get your redemption in by (near) the end of the month you’ll receive the miles on the same day as you would have, had you redeemed earlier in the month.

On the other hand, each Just 4 U account’s redemption inventory resets every week so if you are earning more rewards than you know what to do with, you don’t want to miss a redemption opportunity by sitting on your hands either.

About that stockpiling strategy

Normally, “rump” Just 4 U points expire at the end of the month they’re earned and rewards expire at the end of the month after they’re earned. Back when it was trivial to amass unlimited Just 4 U points alongside credit card rewards a number of people pointed out that these rewards could be extended indefinitely by signing up for a paid FreshPass subscription. I’m sure there are plenty of people still eating for free on the rewards they earned back then!

This naturally raises the question: if another opportunity for unlimited Just 4 U points comes along, should you pay for a FreshPass subscription in order to redeem 22 rewards per week for Alaska Airlines miles? How many subscriptions? One for every member of your family? One for your dog?

This is not, fortunately, a question I can answer for you because it goes to the heart of how you choose to play the game. I chose not to get a FreshPass subscription and stockpile rewards back then simply because that’s who I am: after I’d filled up my fridge, and my freezer, and my cupboards, and my linen closet, and my local free pantry, I just stopped. Paying $99 per year to buy groceries I didn’t want or need for the rest of my life or until the program was devalued simply didn’t have any appeal for me. I wrote it up for my Subscribers-Only Newsletter and moved on.

On the other hand, I know lots of people who stockpile every currency under the sun on the off chance they find an opportunity to score the perfect luxury redemption. The thrill of finding first class award availability or consecutive exotic award nights with one currency is simply more exciting than seeing the value of another hoard whittled away by devaluations, mergers, or bankruptcies is discouraging.

And if you’re one of those people, then why not add Just 4 U into the mix? Of course, I don’t need to tell you that: you probably already have!

Just 4 U Alaska Airlines redemptions work, for what it's worth

A few months back a number of bloggers reported that Just 4 U rewards (the rewards program of Albertsons grocery stores and its countless sub-brands) could be redeemed for Alaska Airlines Mileage Plan miles.

How it works

The basic mechanism is simple. When a Just 4 U account has a store in Alaska designated as your “preferred store,” then you’ll see the following redemption options:

  • 1 Reward: 100 Mileage Plan miles.

  • 2 Rewards: 250 miles.

  • 3 Rewards: 400 miles.

  • 4 Rewards: 600 miles.

  • 5 Rewards: 850 miles.

  • 7 Rewards: 1300 miles.

Thus, you can redeem a total of up to 22 Rewards per week per Just 4 U account for a total of up to 3,500 Mileage Plan miles.

As a reminder, you earn 1 Reward each time you earn 100 Just 4 U points. Just 4 U points expire at the end of each month, but Rewards expire at the end of the month after they’re earned. Paid FreshPass membership keeps your Rewards from expiring indefinitely.

Mileage Plan Miles Versus Grocery Rewards

If you have access to unlimited Just 4 U points, then the “grocery rewards” double dip is the most valuable option because it allows you to stack multiple grocery rewards redemptions on a single purchase, even to the point of generating a negative balance (although since this will invariably raise suspicion, I recommend spending the negative balance instead, for example by buying a prepaid debit card).

That technique lets you redeem 44 Rewards for $64 off your bill when you buy $20 in groceries (leaving you with $44 to spend on dairy, alcohol, gift cards, or anything else that isn’t usually eligible for Rewards).

Note that the grocery rewards option is only more valuable because of the double dip. If you could not double dip grocery rewards, then redeeming 7 Rewards for 1,300 Mileage Plan miles instead of a $10 grocery reward looks a lot more attractive. Lots of people would be willing to buy Mileage Plan miles for 0.77 cents each, at least at the margin.

What this means is that while double dipping grocery rewards may be the best combination of Just 4 U redemptions, single dipping Mileage Plan redemptions at the 7-Reward level is a solid alternative after you’ve redeemed those and have Rewards left over each week. And this is, in fact, more common than you might think.

Leftover Just 4 U Rewards

Take, for example, last week’s offer for 10 Just 4 U points per dollar spent on Google Play cards. Since you can buy cards up to $500 in value, the maximum earning per card is 5,000 Just 4 U points, or 50 Rewards. After redeeming 44 Rewards through the grocery rewards double dip, you’re left with 6 Rewards. By earning a single additional Reward (or using a leftover Reward from a previous week), you can also redeem for the highest-value Mileage Plan reward the same week, before repeating the process the next week.

I don’t engage in much gift card reselling anymore, but when very high earning rates are offered on high-value cards (or even cards you plan to use yourself), you may be able to break even or turn a profit on Just 4 U rewards in addition to the credit card rewards you earn on the original purchase.

Comparing IHG's 4th-night-free with Marriott and Hilton's 5th-night-free

I was reading Danny the Deal Guru’s write-up of the latest Chase IHG Rewards signup offers and something jumped out at me: the 4th-night-free benefit offered to cardholders, including those who hold the no-annual-fee IHG Rewards Traveler card. To be clear, this isn’t a new benefit, it’s just one I haven’t had a chance to think about in depth.

Generally speaking, I don’t rate IHG or their rewards program very highly, because while they have an enormous global footprint, they’re rarely competitive compared with the main hotel programs I rely on, Hilton and Hyatt. For example, I regularly visit Portland, OR, which on a sample search turned up two downtown Hyatt properties priced at 12,000 World of Hyatt points, a Hilton priced at 37,000 Hilton Honors points, a Marriott priced at 30,000 Bonvoy points, and a Kimpton priced at 25,000 IHG Rewards Club points (plus a nightly “amenity fee”). For a one-night stay, it would be ridiculous to choose the IHG property unless you’d built up a large orphaned balance through various shenanigans.

Since my framework is manufactured spend, not signup bonuses, it’s easy to make a direct comparison between the options:

  • 12,000 World of Hyatt points transferred from Chase Ultimate Rewards is worth $120 in cash.

  • 37,000 Hilton Honors points earned at 6 points per dollar with the American Express Surpass co-branded card is between $123 (if the same $6,200 in spend had been put on a 2% cashback card) and $185 if the points were purchased for 0.5 cents each, an offer which is regularly available, including now through March 7, 2023.

  • 30,000 Marriott Bonvoy points are worth between $240 (if you bought the points during one of their periodic promotions) and $300 (if you transferred the points from Chase Ultimate Rewards.

  • 25,000 IHG Rewards points are worth between $150 and $175 if you buy them using the “points and cash” trick (purchasing points while making an award reservation, then cancelling the reservation and having the points refunded to your account).

This makes comparing the four sample reservation options, and indeed comparing all reservation options at the four chains, easy, if on average:

  • World of Hyatt points cost 1 cent each;

  • Hilton Honors points cost 0.42 cents each;

  • Marriott Bonvoy points cost 0.9 cents each;

  • and IHG Rewards points cost 0.65 cents each;

then on a one-night stay you can convert the points cost of any property into the cash cost of manufacturing, transferring, or purchasing the required points. In the concrete example above, we saw that Hyatt and Hilton were quite competitive, while Marriott and IHG Rewards were significantly more expensive options.

On four-night stays, the equation changes, but only for IHG Rewards points. On four-night stays at the other three chains, the cost per point remains the same, while the 4th-night-free benefit offered by the IHG Rewards credit cards increases their value by 33% or decreases their cost by 25% to 0.49 cents each — same difference. The four-night IHG Rewards stay now costs just $122 per night, putting it squarely in the middle of the “competitive” pack of Hyatt and Hilton, or even on the cheaper end (ignoring that pesky Kimpton amenity fee, which you obviously shouldn’t in practice).

Moving to a five-night stay, the equation shifts again, but this time against IHG Rewards, since Hilton and Marriott both offer the fifth night free on award stays. The cost per night on the sample five-night stays with Hilton is $123 per night, with Marriott is $216, and with IHG $130. Hyatt doesn’t offer free nights on longer stays so their cost per night remains flat at $120.

Reference Card

I wanted to use a specific example to explain why I personally don’t care for IHG Rewards, but in case you want to bookmark this post or paste the values into your notes app, here are the shortcuts when calculating the cost of stays of various lengths.

Stays of 1-3 nights:

  • World of Hyatt: 1 cent per point

  • Hilton Honors: 0.42 cents per point

  • Marriott Bonvoy: 0.9 cents per point

  • IHG Rewards: 0.65 cents per point

Stays of exactly 4 nights:

  • IHG Rewards: 0.49 cents per point

Stays of exactly 5 nights:

  • World of Haytt: 1 cent per point

  • IHG Rewards: 0.52 cents per point

  • Hilton Honors: 0.34 cents per point

  • Marriott Rewards: 0.72 cents per point

Now you can easily calculate the cost of reward stays of up to 5 nights in length in every city in the world — not just in Portland, Oregon!

When should you optimize for spontaneous, planned, or predictable expenses?

I like to generalize travel hackers into three broad categories, although none describes any individual perfectly.

Roughly speaking, I think of opportunistic travel hackers as people who keep an eye on signup, referral, and manufactured spending opportunities in order to maximize the value of their earnings throughout the year. I doubt this is the largest category, although it receives the most attention from mainstream blogs, so in some ways it’s the easiest to get involved in. Frequent Miler, for instance, hosts a simple page indicating what current signup bonuses are available and how they compare to previous offers.

The flip side of opportunism is that because it’s opportunistic, it’s unlikely to directly or even closely correspond to your needs. For example, take a look at how Gary Leff is currently promoting the Citi American Airlines business credit card right now: “70,000 by the way is what it costs from the US to the Mideast, India or Maldives on Qatar. You can even fly Qatar’s Qsuites, which may be the best business class in the world.” Fair enough, but what does that have to do with me? The message delivered by and for opportunists is “apply now, earn now, figure out what to do with the miles later.”

The second bucket is tactical travel hacking, which is roughly what I did for our stay at the Grand Wailea: I had a plan for the Aspire signup bonus, a plan for the resort credit, and a plan for the Amex Offer for $70 off $350 in spend at Waldorf Astoria resorts, and as soon as I’d used them all, the card was closed.

Just like opportunism, tactical travel hacking has tradeoffs. By focusing on individual awards, you’re more likely to earn the miles and points you actually want to spend, reducing the chances of orphaned miles in random accounts. On the other hand, if you’re concentrated on a specific award, you’re subject to award availability for that precise award space. This comes up most frequently when looking for premium-cabin airline award space, but limited hotel award space is an increasing problem, especially at premium properties that play games with blackout dates, variable pricing, and of course what qualifies as a “standard” room; while writing up this post I couldn’t find a single date with standard award nights available at the Grand Wailea!

Lately I’ve been thinking a lot more about what I think of as logistical travel hacking. Rather than focusing on the highest signup bonuses (which I may never redeem, or redeem at a fraction of their supposed value), or individual high-value trips which may or may not have award availability when I need it, I’ve been focusing on rewards that I am highly confident I’m going to be able to redeem, even if I don’t know when or where.

This has resulted in a subtle transformation in how I go about earning and redeeming miles and points. For example, I’ve written extensively about how companion tickets like those offered by the American Express Delta credit cards and the Bank of America Alaska Airlines credit cards didn’t offer significant savings when compared to manufacturing spend on higher-earning credit cards. And I still think that’s true, as far as it goes. But the higher your confidence that you’ll be able to redeem your companion tickets at something close to face value, the smaller that trade-off becomes.

Take, for example, the Alaska Airlines companion fare. For roughly $121, plus a $75 annual fee, you can book a second passenger on any Alaska-operated economy ticket, including destinations in Mexico, Alaska, and Hawaii, and including some pretty zany routing rules. The same $196 spent on, for example, office supply store prepaid debit card activation and liquidation fees might earn 100,000 Ultimate Rewards points on a Chase Ink Preferred card, worth $1,250 or $1,500 in airfare, depending on your local opportunities and the frequency of in-store and online in any given year.

From an opportunistic perspective, the companion fare makes no sense, since it would be trivial to get more than $196 in value from 100,000 Ultimate Rewards points. From a tactical perspective, you can imagine signing up for the card when you have a specific, expensive Alaska-operated ticket in mind. But the logistical perspective is different: if you always buy Alaska-operated tickets with your companion fare, then you have the opportunity to optimize the rest of your earning and redemptions around the remainder of your travel needs.

Conclusion

I’ve always said, the point of travel hacking is to spend as little as possible on the trips you want to take, and the least valuable point is the one you don’t redeem. That’s still true, but a few years of travel restrictions have managed to convince me that it’s at least partially incomplete. From the opportunistic perspective, if availability suddenly opens up on a premium carrier or at a prestige property, you need to have the points available to redeem immediately. From the tactical perspective, you grind out the points, miles, and status you need to book the trip you want. But from the logistical perspective, you might choose to cover predictable, recurring expenses with tools like annual free night certificates and companion fares even if you might have short-term opportunities to spend less for the same night or flight. As the joke goes, the Pentagon overpays for toilets but they get a great deal on F-35’s.

Like a lot of people getting started in travel hacking, I first dabbled in opportunistic strategies but found I just didn’t care that much about stockpiling points it would take me years to eventually redeem, at uncertain value. Over the course of a few years, I shifted over to tactically earning bonused points in the currencies I was planning to redeem for specific trips: Chase Ultimate Rewards, Hilton Honors, and US Bank Flexpoints, in particular. And in the last few years I’ve increasingly been focused on logistics: if I know I’m going to book a ticket for two on Alaska Airlines or Delta, or stay at a Hyatt or Hilton, then what those companion tickets and free night certificates do is take those redemptions off my mind, letting me focus on the rest of the pieces of a trip, like deciding when to book through Hotels.com and when to book directly.