MEABNOTE: I’ll be going on a blogging vacation at the end of the year and there won’t be any daily posts between December 18 and December 31. After that, we’ll ring in the new year on January 1, 2025 with the 2024 version of Travel Hacking as Told by GIFs though, so no need to be up in arms, but I guess it’s ok if you’re up in legs.

By popular demand we’ll have at least a few guest posts during the break. If you’d like to write one, please reach out, I’d like to find guest posts for the whole break!

Introduction

We’ve talked several times about the Pepper Rewards gift card selling platform, which seems to have been explicitly designed to transfer money from Venture Capitalist bank accounts to our wallets at lighting speed. In the most recent MEAB post on the subject, I included a toy model based prediction that there’s a 50/50 chance that the company fails by the end of 2024. I’m now updating the timeline for the 50/50 failure scenario to be March 23, we’ll see why later.

Recent Changes

First, let’s discuss how Pepper has changed in the last month:

  • Bonus offers are now targeted to specific accounts
  • Many of the best offers are now limited to one per account per day
  • New accounts get low bonus offers until they spend five-ish figures
  • Account limits are either $5,500, $7,000, or $10,500 spend per rolling 24 hours
  • Most of the rebates are now floated for 14 days
  • Pepper has effectively stopped responding to most support requests
  • Pepper is moving merchant accounts from Stripe to PayArc

The first two bullets seem to be Pepper’s attempt at preventing a few whales from taking all of the best deals’ capacity through botting. The third and fourth bullets seem to attempt to separate gift card resellers from regular users and to separate resellers into tiers. The last two bullets are almost certainly about saving money and lowering reserve capital requirements.

Recent Deals

As degenerate churners are well aware, Pepper has pushed the resale market for high value gift cards down to decades-long lows by offering almost daily:

  • 17-20% discounts on Kohls gift cards
  • 12-16% discounts on Amazon gift cards
  • 12-16% discounts on Walmart and Sam’s Club gift cards
  • 15-18% discounts on Nike gift cards

Let’s get something out of the way about these deals: There’s no world in which Amazon or Walmart are giving gift card sellers a discount in the double digit percentages on millions of dollars of inventory. There’s also no world in which Pepper isn’t paying merchant processing fees of at minimum 2.7%, but more realistically 3%+ on each of these transactions too. Pepper is losing on each of these bulk gift card transactions, period.

Pepper’s Vision

Pepper has started a new funding round a month or two later than I expected based on the toy model, but still within the general time frame. Fortunately for us, their pitch deck and story is on YouTube so it’s easy to see what they’re telling investors. My favorite bits from the video:

  • Pepper is going to be a single shopping portal and remove the need for all the others
  • “Pepper earns a 6% commission on every transaction”
  • Pepper somehow will know your favorite color and shoe size with AI, and this isn’t MEAB snark
  • Their Chief Revenue Officer was a DoorDash sales executive
  • Pepper believes that their total addressable market is $6 trillion (almost 23% of the US GDP, seems legit)

There’s definitely a fair amount of slippery language in the video, but I want to call out the most slippery statement, that “Pepper earns a 6% commission on every transaction”. Look, I actually believe they earn an average of 6% commission on every transaction, but the slippery language is undoubtedly that their 6% is a gross commission on the face value of gift cards, not a profit margin. (I think Pepper is lucky if their current profit margin is -6%; it’s definitely not +6%.)

Side note: I think that 6% number is realistically the discount that they earn on face value for the aggregate of all the gift cards that they sell, making it a really interesting number for any future models.

The Pepper Future

Alright, we’ve buried the lede. Based on my toy model I expected a 50/50 failure by the end of 2024, but I’ve revised that to 50/50 by March 20. Why that date? It’s silly, but there’s a metric that’s more accurate than any toy model in my mind: Almost all high-growth, high-spend VC backed companies start raising their next round of funding 3-4 months before they run out of the cash from their last round; it’s almost universal for companies like this.

Given the above and that Pepper posted their investor presentation on December 8, three months is March 8, and four months is April 8, the expectation value for running out of money is March 23. If they haven’t run out of money by then, it’s probably for one or both of two reasons:

  • They’ve raised more cash successfully
  • They’ve restructured their expenses, including employee and boost costs

I’m sure Youtube is the way to most investors hearts though, right?

My Action

I still use Pepper, and I have pending rebates well into the thousands of dollars floated with them too. My goal is to scale that back gradually as March approaches to limit my exposure in case of a Pepper failure. If this was a public company, you can be completely sure I’d be buying out of the money puts. I also expect that I’ll end up losing some money when they eventually fail, but I can more-or-less control how much and take profits in the mean time.

Good luck and happy Tuesday friends!

The Pepper Chief Revenue Officer’s prior work gives a glimpse into Pepper.

MEABNOTE: I’ll be going on a blogging vacation at the end of the year and there won’t be any daily posts between December 18 and December 31. After that, we’ll ring in the new year on January 1, 2025 with the 2024 version of Travel Hacking as Told by GIFs though, so no need to be up in arms, but I guess it’s ok if you’re up in legs.

By popular demand we’ll have at least a few guest posts during the break. If you’d like to write one, please reach out, I’d like to find guest posts for the whole break!

  1. Do this now: Register for 5x categories on quarterly cards:

    Chase Freedom and Freedom Flex: Grocery, fitness, gyms, hair, nails, spas, and Norwegian Cruises (welcome to the world of sponsored 5x categories friends)
    Discover IT: Restaurants, home improvement, and some streaming
    Citi Dividend: Amazon and some streaming
    US Bank Cash+: I choose utilities and electronics stores

    I try and knock these out on the first day or two of the quarter so I don’t have to think about them after.
  2. The Citi Shop Your Way Rewards card sent new mid-month targeted spending offers for online spend through January 14, 2025. We’ve seen:

    – 250,000 Shop Your Way Rewards points with $1,000+
    – 200,000 Shop Your Way Rewards points with $750+
    – $70 statement credit with $1,000+
    – $50 statement credit with $750+

    As usual, these stack with other offers. (Thanks to birt, Adam, Lindsay, and Tyler)
  3. Giftcards.com has 10% off of its own gift cards through December21. These cards can be used to buy other, third-party fee-free gift cards on the site with promo code EPICGIFT. These probably won’t track on shopping portals when you buy them, but when you use them on another purchase that’ll probably track. There are several credit cards that earn 3x on giftcards.com.
  4. Answering a few of the questions we asked on Friday with American Express’s new Business Platinum $50 quarterly Hilton credit:

    – Will this work with HiltonGiftCards.com? Yes
    – Will this work buying gift cards at a hotel? Yes
    – Will this work at Hilton restaurant? Usually, watch for a 15% extra hold for tip
    – Will this work for a regular hotel to pay your bill? Yes, depending on the front desk’s skillset
    – Who is John Galt? I dunno; or if I do, I don’t want to talk about it here, why do you ask?

    Also, orange-you glad I didn’t say banana? (That’s called a “long con” friends, at least on internet time scales.)

Yes, I know I deserve this.

MEABNOTE: I’ll be going on a blogging vacation at the end of the year and there won’t be any daily posts between December 18 and December 31. After that, we’ll ring in the new year on January 1, 2025 with the 2024 version of Travel Hacking as Told by GIFs though, so no need to be up in arms, but I guess it’s ok if you’re up in legs.

By popular demand, we’ll have at least a couple of guest posts during the break. If you’d like to write one, please reach out!

  1. H-E-B Stores have a $20 H-E-B gift card with the purchase of a $100 Home Depot, Lowe’s, and some other, stupider brands through Tuesday. Scale with multiple H-E-B accounts. Side note: H-E-B is one of the most annoying things that I have to type somewhat regularly.
  2. Chase Offers has 10% back on Frontier Airlines on up to $420 in spend through January 23. Watch for refund policies on Frontier. Side note: Frontier is one of the most annoying airlines that I never have to fly.
  3. The Bank of America Alaska card’s 75,000 miles after $3,000 spend in 90 days bonus is still around. Side note: Yesterday, some bloggers started pushing a 70,000 mile Alaska sign-up bonus instead because it pays them affiliate revenue, and based on the coordinated timing, it’s likely a higher than usual payout too; caveat emptor.
  4. Breeze has a 50% off fare sale with promo code GOALS for flights booked by tonight. Evidently, they saw that the other second tier US airlines had a fare sale yesterday and didn’t want to be left out.

Happy Thursday!

Even this brand of soda is easier to type than H-E-B.

MEABNOTE: I’ll be going on a blogging vacation at the end of the year and there won’t be any daily posts between December 18 and December 31. After that, we’ll ring in the new year on January 1, 2025 with the 2024 version of Travel Hacking as Told by GIFs though, so no need to be up in arms, but I guess it’s ok if you’re up in legs.

  1. Do this now: Register for the upcoming Alaska Airlines premium card’s waitlist and earn 500 miles instantly. You’ll also earn a bonus 5,000 miles if you apply for the card when it comes out using your waitlisted link. Apparently the premium card will have an annual fee of $395 and:

    – Earn 3x on foreign currency transactions and foreign USD transactions
    – Earn 3x on dining
    – Have a “Global Companion” pass for award tickets
    – Have free WiFi vouchers and reduced award ticketing fees

    The card arrives this summer. (Thanks to Esteban)
  2. Many US Airlines are running a holiday fare sale:

    Alaska award and paid through Monday
    JetBlue paid through tonight, 25% off with promo HELLO25
    Southwest award and paid through tomorrow night
    Avelo $40 off round-trip paid travel through tomorrow night with promo FLY40

    My tea leaves suggest it’s going to be a rough Q1 for second tier airlines, especially Spirit which couldn’t even afford to run a sale.
  3. Two of the three main Incomm gift card sites have new promos (the third one’s promo is still in effect):

    VanillaGift.com: No purchase fees on $150+ with promo code VGHOLIDAY24
    TheGiftCardShop.com: No purchase fees on $200+ with promo code HOLIDAY24

    Ok fine, the third one is MasterCardGiftCard.com with promo code NOFEES24. I don’t like repeating a deal, but I guess I can’t leave you hanging.
  4. American Express has a targeting offer for 75,000 Membership Rewards after $6,00 spend in four months on Blue Business Plus no annual fee card, available via your dashboard if targeted.

Happy Wednesday!

A typical MEAB reader left hanging, probably.

MEABNOTE: I’ll be going on a blogging vacation at the end of the year and there won’t be any daily posts between December 18 and December 31. After that, we’ll ring in the new year on January 1, 2025 with the 2024 version of Travel Hacking as Told by GIFs though, so no need to be up in arms, but I guess it’s ok if you’re up in legs.

  1. Do this now: Register for Hilton’s Q1 promotion for double points for stays between January 1, 2025 and April 30, 2025.
  2. The Barclays Frontier Mastercard has a sign-up bonus of 100,000 miles after $3,000 spend, Gold elite status, and a $100 flight voucher. You have to have another airline’s co-branded card to be eligible, and you have to spend in either 90 or 180 days, depending on how you interpret the terms and conditions, or more accurately how Barclays interprets the terms and conditions. You can verify your reading comprehension and that your other airline co-branded card is eligible here.

    Make sure to put a reminder in your phone to go verify the other airline co-branded card in Barclays’ systems after you receive the Frontier card. (Thanks to FM)
  3. American Express’s referral bonuses are currently at a relative maximum, and in the last week or so more people have been able to generate the heightened offers. The referrer will get between 15,000 and 30,000 Membership Rewards, and the referred offers are:

    – Business Gold: 200,000 Membership Rewards after $20,000 spend in three months
    – Business Platinum: 250,000 Membership Rewards after $15,000 spend in three months

    It’s ok for P1 to use P2’s referral and vice-versa, and if you don’t have one of those, ask around for a heightened referral offer and make a new churning friend; it’s a great way to network too.
  4. The Daily Churn podcast’s most recent episode discusses two interesting plays combined together that are below surface level but sort-of out in the open, starting at 28:00 minutes in:

    – Gift of College Cards at giftcards.com
    – The Kudos quasi-portal card-linked bonus program (use a friend’s referral code)

    The quick summary is that they’re working well together.
  5. American Express has a new Membership Rewards to JetBlue 25% transfer bonus through December 31, which makes the transfer ratio 1:1. You’ll often do better booking with a Business Platinum though.
  6. A PSA and warning: American Express links that were put together artificially by combining multiple offer components in an unintended way keep finding their way onto public blogs, which is ok, but they’re not labeled or explained as manufactured artificial links. My suggestion: Always know the provenance of no-lifetime language links that you’re using. DDG has appropriately labeled this recently, but not all bloggers are doing so. What’s the link? This time it’s a 100,000 Membership Rewards personal Gold link with a $6,000 spend in six months requirement, but others have surfaced over the last couple of months for Business Golds and Business Platinums too.

    How risky are these links? It’s been over 6 years since there were reports of adverse action for using unintended links, so the risk is probably low, but I don’t like when you’re not told that you’re taking a risk with a manufactured link, even if it’s low. One day of course American Express may decide that it doesn’t like people making links themselves in ways never intended to work. Since no one asked my opinion: The risk isn’t worth it at 100,000 points, but if it were 80*270,000 points we’d be having a serious conversation.
  7. Spirit Airlines has a status match to either Silver or Gold that lasts 90 days, and a there’s a fast-track challenge to hold it for longer (I imagine the challenge won’t make sense for any of you unless your name starts with an “S” and ends with a “hay”). Status doesn’t let you pick a big front seat for free, but it does waive plenty of other fees.

Breakage from failed reading comprehension illustrated.

MEABNOTE: I’ll be going on a blogging vacation at the end of the year and there won’t be any daily posts between December 18 and December 31. After that, we’ll ring in the new year on January 1, 2025 with the 2024 version of Travel Hacking as Told by GIFs though, so no need to be up in arms, but I guess it’s ok if you’re up in legs.

  1. Do this now: Register for Chase’s giveaway of one million Ultimate Rewards. You can bot enter once per day through the end of January. There will be 10 winners in March, and they might as well be you guys.
  2. Target has its annual 10% off of Target gift cards sale tomorrow and Sunday, limit $500 per Target Circle account. A few notes about this deal:

    – You’re now limited to one per Target Circle account, so I guess get more of those?
    – Pepper has pushed the resale value of $500 Target cards to about 90-91%
    – Target RedCard 5% discounts won’t work
    – DiscoverIT cards have Target at 5% in Q4

    This deal scales somewhat easily in store, but historically Target gift card resale prices dip after this sale in December and don’t recover until mid-January.
  3. Chase Ultimate Rewards has a few transfer bonuses through January 15, 2025. Ordered by longest transfer partner program name to shortest because sometimes aesthetics matter:

    – AirFrance / KLM FlyingBlue: 20% bonus
    – Air Canada Aeroplan: 20% bonus
    – IHG One Rewards: 70% bonus

    It’s easy to get great value out of the top two programs, but hard for the third.
  4. Staples stores have fee-free $200 Visa gift cards starting Sunday and running for two weeks through December 21.

    These are Pathward gift cards.
  5. The Shop Your Way Rewards portal has a 5% discount when redeeming points for Visa gift cards through December 31. You’ve probably earned these points from a Citi Shop Your Way card, but it is technically possible to earn them by buying stuff at Sears.com too.
  6. Chase Offers has an offer for 10% back on AirCanada purchases of $100 or more, limit $40 cash back. Game? Yes, game.
  7. GiantGiant FoodsMartins, and Stop & Shop stores  stores have 3x points on Visa gift card purchases through Thursday, December 12, limit $2,000 per account except at Giant, where the limit is $1,500 per household, because they also ordered their limits by name length presumably for aesthetic reasons.

    These are Vanilla gift cards.
  8. VanillaGift.com has a promotion for a bonus $10 Visa gift card with the purchase of $100+ in Visa gift cards. Side note: Yes this is a nice return in absolute percentages, but have you ever tried to drain a $10 Vanilla Visa card?

    These are (obviously) Vanilla gift cards.

Have a nice weekend friends!

Even tool manufactures arrange for aesthetics, don’t judge.

MEABNOTE: I’ll be going on a blogging vacation at the end of the year and there won’t be any daily posts between December 18 and December 31. After that, we’ll ring in the new year on January 1, 2025 with the 2024 version of Travel Hacking as Told by GIFs though, so no need to be up in arms, but I guess it’s ok if you’re up in legs.

  1. Meijer stores have 50,000 MPerks Points with the purchase of a $500 third party gift card, including bulk brands like Apple and BestBuy, through December 14. There’s a limit of 50,000 points per account, but what’s the limit on accounts? The limit does not exist.
  2. Meijer stores also have $10 off of $100 or more in Visa or Mastercard gift cards through December 21. This one requires that you clip a digital coupon, but seems to be the variety that you can reclip after each purchase, meaning again, the limit does not exist but different.
  3. Alaska Airlines has a paid and award fare sale through this evening. I’m seeing:

    – Transcons at 9,000 miles each way
    – Mainland to Hawaii 9,000 miles each way
    – Mexico at 15,000 miles each way

    These continue to be the best award sales for medium-haul flights that no-one talks about because something something, apathy is real, something something.
  4. Costco has $100 in Uber Gift Cards for $75 through tonight. There are multiple reports that Uber charges more when you have credits on your account, so apply them retroactively to a ride instead of adding them to your account ahead of time, or just use Uber Eats to order a private taxi for your burrito.
  5. The Citi Shop Your Way Rewards card, the card that would probably be driving the private taxi for your burrito if it was human, has new beginning of month offers that reset monthly for December, January, and February:

    – $50 statement credit for 5 purchases of $75 or more each, up to $150 for all three months
    – $60 statement credit for $450+ spend, up to $180 for all three months

    (Thanks to Dave M and birt)
  6. The Chase Southwest Rapid Rewards Plus card has an increased sign-up bonus of 40,000 Rapid Rewards points and a $400 statement credit with $3,000 in purchases in four months for applications through December 16.

    If you’re not going for a Companion Pass, which you probably shouldn’t chase if you don’t fly Southwest more than 3-4x annually, then this might be a better option than a pure points bonus.
  7. Preferred Hotels has a promotion for 35,000 bonus points for paid three night stays booked by Wednesday night for travel through March 31, 2025.
  8. Giftcards.com is currently 3x at most airline shopping portals and 4x at Chase portals. AA and Southwest points earned through portals count toward status too.

    These are Pathward gift cards.
  9. The Incomm gift card sites have new deals:

    MasterCardGiftCard.com: No fees through December 31, code NOFEES24
    VanillaGift.com: No fees through tonight, code VGCYBER24
    TheGiftCardShop.com: $10 Zillions with $100+ in Visa cards through tonight, code BF24

    These are (obviously) Incomm gift cards. None of these earn points on first party American Express cards.
  10. Typically Citi offers 20% off of many ThankYou point gift card redemptions on Cyber Monday and today is (maybe? I dunno, I’m not getting up that early in the morning to verify #sorrynotsorry) traditional. With Apple cards reselling at about 91% of face value, you can use this promotion to cash out ThankYou points indirectly at ~1.1 cents each, or even better if you have the Rewards+ card.

Have a nice Monday!

Seatbelts are required in private taxis too.

We’ll try and keep it quick today, but there’s still a lot:

  1. Do this now: Register for Best Western’s promotion for 5,000 bonus points for every two nights stayed between December 2 and February 2, 2025 at most North American properties. You can earn the bonus up to four times which sounds like way too much Best Western for my taste, but you do you.
  2. US Bank has double cash back on all card linked offers and shopping portal bonuses through tomorrow night, and all the tips from last time still apply too.
  3. The American Express Delta Gold personal card has a heightened bonus of 50,000 SkyMiles and a $500 statement credit after $3,000 in purchases and making a single purchase at Delta.com within six months. You can find the offer by going through a flight booking on the checkout page, whether or not you actually buy a ticket.

    The annual fee is waived the first year, making this probably worth burning a 5/24 slot. (Thanks to DDG)
  4. Bilt Rewards has some promotions this week:

    – 3x earning on non-bonuses spend up to $500 spend through the end of November
    – Earning 0.5x on new mortgages (although they’re not truthful about being first, see Mesa)
    – Points are worth 1.4 cents each on December 1 at Amazon for Platinum members

    In churning, there’s always a pariah in a group (cf. gift card buying group A, buyers club B, and bank C), and Bilt is probably that for credit cards.
  5. American Express Offers has new travel related card offers:

    – $300 statement credit with $2,000 or more at Virgin Atlantic by December 30
    – $30 statement credit with $150 or more at Turo by April 3, 2025

    (Thanks to DoC)
  6. Office Depot / OfficeMax stores have $15 off of $300 or more in Visa gift card purchases through Saturday. For best results:

    – Link your cards to Dosh
    – Buy in even multiples of $300

    These are Pathward gift cards.
  7. GiantGiant FoodsMartins, and Stop & Shop stores have new gift card deals starting tomorrow for:

    – 12x points on Zillions gift cards
    – 10x points on Home Depot and Uber gift cards

    There’s likely a limit of $2,000 per account, but the fine print in preview ads is too low resolution to read. UPDATE: There is a $2,000 limit, and Giant Foods doesn’t currently show the promo. It will probably still work but may earn less than other affiliates based on historical patterns.
  8. Breeze has $29 fares for travel booked tomorrow through Sunday with travel through May 22, 2025. There are a few blackouts around days that you’d expect.
  9. Giftcards.com is currently earning 2.5 miles per dollar through the AA shopping portal, which is great for manufacturing Loyalty Points.

    These are Pathward gift cards.

Happy Thanksgiving!

Never forget the AA First turkey sandwich, which unfortunately is real. Happy Thanksgiving!