Quick hit: mobile balance loads trigger refreshed Amex personal Gold credits

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I applied for an American Express Gold card back in April so have been following especially closely the recently announced changes to the card: a $325 annual fee, $50 semiannual Resy credit, and $7 monthly credit at Dunkin Donuts.

I already knew that purchases at any Resy restaurant would trigger the semiannual statement credit because of my experiments with my American Express Delta Business Platinum card, but I wasn’t sure whether the $7 monthly credit could be triggered without going into a Dunkin location.

So, I bought $7 of credit in the Dunkin Donuts app on Monday, July 29. On Wednesday, July 31, I received an e-mail alerting me that I’d received a $7 statement credit for the purchase.

I’m not a great consumer of either fast food coffee or fast food donuts, but as the saying goes, I’ll take any bank’s money as long as they’re giving it away. This benefit is already live, so start using it today.

What I learned attending the Karlovy Vary International Film Festival (twice)

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I’ve been out of the country for a few weeks visiting the Czech Republic, building the trip around attending the 58th Karlovy Vary International Film Festival. This was my second time at KVIFF; we had such a great time attending just a few days of the festival back in 2018 that we decided to spend a full week this time. That’s not ultimately how it worked out, for reasons that had (almost) nothing to do with the festival itself.

Since I knew nothing about international film festivals until I started going to Karlovy Vary, I want to share some lessons that I’ve learned. I hope some of these will be even be applicable to other major film festivals, since I think they’re all more or less run by the same people.

Scheduling and transportation

Film festivals are great to plan travel around, because they’re scheduled long in advance and they’re always in the same locations, so you can start looking for award flights and hotel stays far in advance. Next year’s KVIFF is July 4-12.

I did not start looking very far in advance, but was still able to book economy award seats to Prague on Icelandair using 35,000 Alaska Airlines Mileage Plan miles and $228.15 in cash, and return flights from Prague in Aer Lingus business class for 55,000 Mileage Plan miles and $57.90.

Since we were flying in the first day of the festival, we walked to the public bus stop at Prague’s Ruzyně and took the 100 bus to the Zličin metro stop about 20 minutes away, then got on the 305 bus to Karlovy Vary’s Tržnice bus station, which took a little over 2 hours. You can tap to pay on both busses (and indeed, every form of transit we took), so we didn’t need to futz with the ticket machines. There’s a zone-based system outside of Prague proper, and Karlovy Vary is in zone 13, so the bus from Zličin cost 140 CZK, or about $6.

I know Europeans love taking busses everywhere, but we’re not Europeans, so we took the train back, departing from Karlovy Vary’s Horní train station (the Dolní station closer to the center of town runs a service train up to the Horní station but we just took a 5 minute bus ride from the city center). The train takes a much more circuitous path than the bus, so the return trip took about 3 hours and 15 minutes, and cost 498 CZK, or $21.31. If you’re going straight back to the airport from Karlovy Vary, then taking the reverse of our bus route would almost certainly be more convenient.

Where to stay

Our first trip to Karlovy Vary in 2018 was a bit spur of the moment, so finding decent hotels was a struggle. We ended up staying at a kind of quaint converted mansion or palace some ways up one of the hills surrounding the festival area. The hill ended up being an annoyance, since every trip back to the room would leave us soaked in sweat (KVIFF is in July, after all).

So this time, I focused on hotels directly along the river Teplá, which runs through the festival area. I found what seemed like a terrific deal at the Park Spa Hotel Sirius (you can read my 2/10 review there): $1422.78 for 7 nights, with full board and a spa package. The rate was so low I assumed they didn’t realize the film festival was taking place or they would have hiked the rate, since the front door practically opens onto the main festival grounds, with a great view from the windows.

Well, it turns out this was a huge mistake. Not because of anything the hotel did or didn’t do, but because every single night of the festival there was a DJ spinning in the center of the main festival grounds until 3 am. The ones right outside the windows of our room. We tolerated this for 5 nights, but at that point had slept so little and seen so many movies we decided to pack it in and head to Prague.

In short, my solemn recommendation is to not stay at any hotel or apartment facing the river during the festival. Either go a little up the hill from the river like we did on our first trip, or stay outside the resort area in the more commercial or residential parts of town a block or two from the river.

Paid tickets

It is possible to just show up to the festival and buy movie tickets, and I suspect that there are people who take day trips from Prague just to experience the atmosphere and see whichever movie they can get tickets to. I’m not sure how far in advance paid tickets can be purchased, since we’ve never gotten tickets that way. Paid tickets can be purchsaed from box offices scattered around the festival grounds.

Festival passes (1)

For both of our trips, we bought festival passes, which give you a little more control over which films you get to see, although not all that much more.

Festival passes can only be purchased in-person once you arrive in Karlovy Vary. There’s no way to buy them online or in advance. We arrived in the early afternoon and bought our passes immediately, although I had them activated for the day after we arrived, so we did not end up seeing any movies on the day of arrival. This was revealed to be a minor error, because of the way passes are used to reserve tickets.

Once you have one or more active passes, you can load them into the KVIFF smartphone app. I recommend downloading the app in advance and creating your account, but my partner and I both had to delete and reinstall the app for it to function properly (a belated realization that led to another missed half-day). Importantly, you can load more than one pass into the app, so you can reserve multiple seats for the same movie. For showings with assigned seating, I believe the app tries to find seats together when you do this.

Each day at 7 am, reservations become available for films showing the following day. It’s worth describing the rhythm of how this works: before you go to bed on Monday, you look at the schedule for Wednesday for every movie you’d even slightly be interested in seeing. Then you set an alarm for 6:55 am. At 7 am Tuesday morning, you open the app and request 3 reservations for those Wednesday movies. Then, you wait, because everyone else in Karlovy Vary is doing the exact same thing. As the server resolves each request, you’ll be told whether your reservation was successful. If not, you can put in another request, although by 7:30 or so most in-demand reservations will have been taken.

Each pass allows you to hold 3 successful reservations per day, and you can make as many requests as you want until you reach that limit. It was unclear to me from the instructions whether a canceled reservation would “free up” that slot or if once a request was successful that slot was permanently used up.

Let me be clear: you will not get your top three choices every day. If you are lucky, you’ll get one of your top three choices every day. More people want to see each film than there are reservations available, and this is the way those reservations are rationed.

Once you’ve successfully made a reservation, you can pick up the paper tickets from any box office using your physical festival pass.

Festival passes (2)

A second way to get tickets using your festival pass is to go to the box office and see what they have available for sale. Your pass gets you unlimited free tickets from the box offices for showings each day and the following day. Lines are often very, very long when the box offices open at 7 am, but if you’re up at 6:55 anyway in order to make reservations, you may as well be standing in line too. We did not try to get tickets this way at 7 am, but after the lines died down we did check whether there were any more tickets available, and there always were, although again, not to the most in-demand showings.

Festival passes (3)

Finally, there is yet another way to use festival passes to see films (and attend other events, like press conferences): outside each theater and event space there is a roped off line or holding area, where passholders who don’t have tickets can wait until 5-10 minutes before the event starts, when enough people are admitted to fill the empty seats.

For major movie premiers, this is likely the only way you will be able to attend, so if there’s one movie you absolutely have to see during the festival, plan on staking out a place in line at least an hour or so before it’s scheduled to begin.

Disneyworld for adults

Those are the logistics. What is the festival actually like? It’s an amusement park built into a fully functioning city. The main attractions are the rides — the films being shown all around town. There are screenings in huge corporate auditoriums, stately imperial opera houses, hotel ballrooms, and medium-sized side rooms (the main building of the festival is a hotel and conference center the rest of the year).

Besides the rides, there are also meet-and-greets: press briefings and panel discussions about the films being screened.

There’s a fair amount of amusement park food being sold from kiosks around the festival, all of which I tasted was excellent. There are also beer and cocktail kiosks. Everything was reasonably priced, presumably because the rest of the city was operating as usual so there weren’t any obvious price-gouging opportunities, except the gift shop, where we happily spent money restocking our dated KVIFF gear.

This analogy kept returning to me over the 5 days we were there, spurred by something I remember a Disney hacker saying years ago: people who go to Disneyworld without putting in the work to plan their stay get frustrated, but what other trip would you spend $10,000 on and just show up for a week hoping everything will work out?

There were some genuine pain points at KVIFF. The fact that the app needed to be reinstalled wasn’t something we could have predicted in advance and put a real cramp on our first 24 hours in town. The fact that our hotel was so incompatible with sleep that we had to leave early is something we can account for in the future by staying further from the main drag.

But a lot of the annoyances are just how the festival works, and if you want to see any films at the festival, you have to adjust to the requirements, primarily waking up in time to put in your reservation requests, and having an open mind about which films you’re willing to watch. Once we got the hang of it, we didn’t have any trouble seeing 2-3 films each remaining day we were in town.

Conclusion

I think part of the glamour of the film festival circuit is the overwhelming feeling that it’s not about you, the public, and the festival does a good job playing up this feeling. Before each film there’s a brief spot highlighting an event from the previous day, like a movie premier or a gala event, lifetime achievement awards, things of that nature, and all the footage is shot right where you’re sitting, or where you’ll be sitting tomorrow, which gives a sense of proximity to fame and power.

These festivals are, after all, basically trade shows where venders show off their latest projects hoping for bids from investors and distributors, but the venders and investors are household names, at least to people who follow the film industry enough to go to a film festival. The fact that they let the public in at all is a kind of cross-subsidy to get the movers and shakers in the same place, while the real action takes place in the suites upstairs.

Like if Disney’s corporate headquarters were underneath Splash Mountain and they used ticket revenue to pay their power bill.

Quick hit: no, Freedom family product changes don't reset your quarterly bonus spend

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One of my favorite techniques is requesting product changes from Chase personal credit cards where I received a signup bonus to Freedom cards that earn 5 Ultimate Rewards points per dollar in their quarterly bonus categories, on up to $1,500 in spend per account.

This technique doesn’t get written about as much as it used to because most travel hackers prefer to chase signup bonuses, which quickly puts them over Chase’s rules for approving personal credit cards.

As a reminder, you usually can’t get a Chase signup bonus if you already have a specific card, or have received a signup bonus for it in the last 24 or 48 months, depending on the card. One way to start that clock ticking again is to request a product change to another card. My current preference is for the Freedom Flex card, since it combines the quarterly bonus categories of the Freedom (not available for new signups) and the uncapped 3 Ultimate Rewards points per dollar spent at drugstores of the Freedom Unlimited.

I had done this a number of times in the past, so I was sitting on 3 Freedom cards on which I had already reached the quarterly cap when I applied for and completed the minimum spend requirement on my new Freedom Flex. Once that signup bonus posted, I called in and requested product changes from my Freedom cards to Freedom Flex cards. Note that when doing this a new card and card number will be issued, so be sure to keep an eye on any recurring bills that are charged to your cards.

What I was unsure of was whether these product changes would reset my quarterly bonus earning cap, because I had never changed products within the Freedom quarterly bonus family; I had only moved to and from quarterly bonus cards, not between them. If product changes reset the quarterly bonus counter, then during promising quarters you could max out each card twice, as a kind of backdoor “upgrade bonus.”

But, regrettably, the quarterly bonus counter was not reset by my product change, so even though the Freedom Flex cards have new numbers, it appears everything else about the old Freedoms was saved and ported over to the new accounts.

Impressed by first MaxMyPoint hotel award alerts

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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.

Quick hit: two more free options for manufacturing debit transactions

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I wrote recently about some tools I use to manufacture debit card transactions in order to trigger the highest rates on rewards checking accounts (often but not exclusively marketed under the “Kasasa” brand).

Doctor of Credit then joined in the fun, noting that one of the easiest options, adding credit to your Amazon balance, has become onerous to the point of uselessness as they raised the minimum balance reload amount to $5 from the previous $1 minimum. Unless you’re a big Amazon spender, you’ll quickly end up with more money in Amazon credit than in interest.

With that in mind, I ran a few more experiments and found two more possibilities that are working for me for now. Note that individual banks and credit unions may code transactions differently so you’ll need to verify for yourself whether these meet the transaction requirements for your accounts.

Robinhood

Robinhood, the free stock- and crypto-trading app I write about occasionally, allows you to fund your cash balance using a debit card with no fee and a minimum deposit of $1. The money is immediately available in your account to withdraw or invest, as far as I can tell, and Robinhood does support fractional share ownership so you could even use this technique to drip some of your interest into the stock market, one of many ways to exercise compounding discipline.

PayPal

PayPal also allows you to add money to your balance with debit cards, again with a minimum of $1. PayPal in principle supports multiple cards per account, so you could use a single PayPal account to meet the debit requirements on more than one high-interest accounts. However, since PayPal also doesn’t have much in the way of identity verification, if you’re considering this I would personally suggest using a new PayPal account for each debit card you plan to use, so that if one account is frozen or closed it won’t necessarily impact the others you’re using.

Conclusion

Two final quick points. First, on the account I’m currently experimenting with, both Robinhood and PayPal transactions post as “signature” transactions so should count towards my qualification requirements, but that’s something that you’ll need to monitor for each of your accounts and each of your methods. No one else can do it for you and datapoints age fast in this game.

Finally, as hinted at above, with any service you’re experimenting with to manufacture transactions you need to keep in mind two parameters: how many accounts can you have, and how many cards can you link to each account? Venmo works great for my round-up savings account because it allows transactions under $1, but I can’t link additional debit cards. The Cash app and Robinhood (with their $1 minima) only allow one debit card to be linked at a time. PayPal is more flexible on the number of cards you can have linked, but many of us have horror stories about past account closures (even though mine ultimately ended with a fat settlement check).

Venti reads my blog and makes some big, immediate improvements

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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 I'm thinking about money these days

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Personal finance and travel hacking in the United States are almost always linked through the intermediary of credit cards, which unlike in most civilized countries are allowed to charge lightly-regulated fees which they rebate to customers in the form of cash, cash-equivalents, or alternative loyalty currencies.

These schemes are usually devised with the concept of “stickiness” in mind: you can offer almost anything to customers in the short term if it’s so hard to switch financial providers that they continue to give you business for years or decades after the initial “acquisition cost” has vanished off your balance sheet.

What travel hackers know is that nothing is as sticky as people think it is, so in fact they don’t need to change their spending habits at all in order to trigger many of the benefits financial providers think will lock in their business in perpetuity.

With all that said, here’s how I’m thinking about investment options these days, keeping in mind just how low those barriers really are in practice.

Rewards checking accounts

Rewards checking accounts typically offer above-market interest rates on balances up to a certain limit, as long as direct deposit and monthly transaction requirements are met. I usually search for the highest-earning accounts on depositaccounts.com, but here are the three I’m currently using:

I primarily use Consumers Credit Union as a current account to manage payments and for ATM withdrawals, since it has a lower limit on the maximum interest rate but also rebates third-party ATM fees; I don’t mind if my balance falls below $10,000 on any given day, in other words.

Two other options I’ve looked at closely are the FitnessBank and Orion Federal Credit Union accounts, which offer 6% APY on up to $25,000 and $10,000, respectively. The FitnessBank requirement of linking a step-tracking device and walking an average of 10,000 steps per day feels too fidgety for me, although if you’re already tracking your steps and know you’ll easily meet the requirement then it seems like a fine option. The Orion FCU requirement for both $500 in deposits and $500 in debit card purchases would be easy to automate, but with such a low limit on the 6% APY balance it hasn’t been a priority for me to set up an account there yet.

Round-up savings

Blog subscribers knows about my long-standing affection for round-up savings accounts. Unfortunately, my 10% APY round-up savings account is no longer available to new members; in fact, the credit union that offered it no longer exists, although I was grandfathered into the old account structure during the aquisition.

I have experimented at length with this account, and as far as I can tell, I can make exactly 29 deposits per day in round-up transactions, which I plan to until the account reaches the $250,000 insurance limit or is closed for deliberate and flagrant abuse — whichever comes first.

Peer-to-peer installment lending

Peer-to-peer lending emerged in the 2000’s during the first wave of what today we’d call “distributed finance.” The idea was that instead of borrowing from the big banks you’d borrow from your fellow citizens; instead of putting your money in the anonymous stock market or a local savings account, you’d invest in individual home improvement projects or weddings or hospital bills. At the time, the two most prominent platforms were Lending Club and Prosper, joined by a few minor platforms like Fundrise and Kickfurther (and, I’m sure, many others I’ve forgotten or never heard about).

Lending Club and Fundrise have both pivoted into more straightforward banking and investment operations, but much to my surprise, Prosper is still chugging along letting you buy shares of individual promissory notes in increments as low as $25.

Unlike the high-interest accounts described above, lending through sites like Prosper comes with risk. Even worse, it comes with unknown risk. At the individual note level, there’s individual risk, but this is negligible: if you buy thousands of $25 loans, some of them will default simply because you’re exposed to the individual life histories of thousands of people, and shit happens even to healthy, employed, home-owning borrowers.

At the institutional level, Prosper’s credit-rating system might be fundamentally flawed: you might expect a 5% default rate from “AA” borrowers (Prosper’s highest rating), but the true number is 15% because some unaccounted-for variable skewed Prosper’s ratings too high.

Your borrowers may be also be exposed to an economy-wide risk, like a nationwide fall in housing prices, or a shooting war with a rival power, which eliminates the advantages of diversification: all of your borrowers might default at once if they’re drafted to go save Taiwan, whether they live in California or Oklahoma.

But these peer-to-peer platform loans have another risk, the financial solvency of the platform itself. In the case of Prosper, you are not actually lending any money to borrowers. You are buying a repayment-contingent note from Prosper, which originates and owns the actual loan to the borrower. As long as the borrower makes their payments, and Prosper pays its bills, then Prosper will transmit the borrower’s payments to the owners of those repayment-contingent notes. But if Prosper itself files for bankruptcy, the value of the loans will be assets of the bankruptcy estate, and lenders will be left with unsecured claims against that estate.

I personally used to consider this the main risk of lending through Prosper. I thought people would happily lend through them until the first economic calamity came along, then Prosper would be wiped out, the notes would be worthless, and the whole peer-to-peer lending experiment would come to an end.

That isn’t what ended up happening, and Prosper has survived and continued to both issue loans to borrowers and sell notes to investors. The website remains very primitive and it still takes me several clicks to find the simplest settings, so automating investments is essential.

I’ve found the easiest way to invest with the platform is not to use their “Auto Invest” feature, but the confusingly- and similarly-named “Recurring Order” function. The recurring order function allows you to specify loan characteristics to filter for (I chose “AA” and “A” graded loans, with yields above 10% APY) and then as those loans are added to the platform it will automatically buy them in the increment you specify (I chose the minimum, $25).

The platform seems to have a lot of loans, so the recurring order function hasn’t had any trouble finding qualifying loans for me to buy, but at some volume there presumably is a trade-off between loan quality, interest rate, and purchase size: if you are fixed on quality and rate, then you might have to buy more than $25 per loan in order to meet your demand for volume. I doubt I will ever hit that point and I don’t spend any time worrying about it.

Stocks, flows, risk, and compounding discipline

To the best of my knowledge, I coined the term “compounding discipline” to refer to the need to make sure that if you rely on your interest compounding over time, then you have to put in the work to make sure it actually is.

A $25,000 balance at Andrews FCU will earn about $120 per month at the Kasasa Cash rate of 6% APY. But a balance of $25,120 will also earn about $120 per month, because the last $120 earns only 0.5% APY. You can earn $120 per month forever, but if you want your savings to compound, then you have to exercise compounding discipline and move that $120 each month into the next vehicle you have available.

The way I’ve formalized this discipline is to split my savings into two broad categories: I invest bigger and faster in safe assets and lower and slower in risky assets; the returns generated by the safe assets pay for the investments in the risky assets. I’ve used the example of Prosper peer-to-peer lending, but I don’t think they’re better or worse or more or less risky than bitcoin or real estate or reselling on Amazon. If one of those is more attractive then you should do it instead. The point is simply to make sure you have somewhere to put the next interest payment so your assets keep compounding at the right mix of risk and return for your situation.

Conclusion

Sharp readers may have noticed I’ve left out the only savings vehicles most Americans have: their individual retirement accounts and workplace-based 401(k) and 403(b) savings accounts. I’ve also ignored the tax implications of the various investment vehicles available. The omission is deliberate: I don’t think about these at all.

If you maximize your annual contribution to your IRA and workplace retirement accounts, and select a low-cost, stock-heavy mutual fund, and make sure your dividends and capital gains are set to reinvest, then you’ll die a millionaire. There’s nothing to think about and it’s not especially interesting to talk about. Once you’ve got all the settings configured right in your payroll software (not always easy!) it shouldn’t take more than 15 minutes a year to make sure everything’s on track.

"How do we scale this?"

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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.