How to Money: Friday Flight – Moneyless Millionaires, Credit Card Churning & AI Goes E-Commerce (#1053)

Release Date: October 24, 2025
Hosts: Joel & Matt

Episode Overview

This Friday Flight edition of How to Money sees hosts Joel and Matt tackle the creeping costs of simple hobbies, the complexities facing modern millionaires, the growing prevalence of AI in our spending lives, and the pros and cons of credit card churning. The duo bring their signature blend of practical financial advice, personal anecdotes, and wry humor, all focused on helping everyday listeners navigate money decisions with more clarity. The show also features memorable segments on protein powder scandals, the subscription craze (from car washes to digital tools), and resources for managing medical costs.

Main Themes & Key Discussion Points

1. The “Running Industrial Complex”

(Start ~04:35, In-depth 05:30–11:22)

Key Idea:
Running is a pure and affordable way to engage in fitness, but it’s now embroiled in consumerism—high-end gear, pricey travel races, and targeted ads threaten to turn it into an expensive hobby.

Highlights:

• Joel’s Marathon Experience: Joel completed his first marathon with help from a long-time listener, Greg—on his 104th marathon!

  “I don’t think I would have done nearly as well if it wasn’t for Greg...it almost felt like one of those monkey backpacks where I’m holding onto the tail and he was dragging me all the way. But it was more of, like, verbal kindness that dragged me along.” —Joel (05:00)

• Affordability vs. Hype:

  “Running is this sport in its essence. It’s like the purest, one of the purest things you can do as a human…But it feels like running is starting to get hijacked by this American consumer mentality.” —Joel (06:08)

• Race Entry Fees & “Tour” Packages:
  Elite race entries like London’s marathon may cost as much as $4,000 through tour operators, sparking a debate about “bucket list spending” versus the purity of running.

  “If you have the money to do it...this needs to be your splurge. This needs to be your craft beer equivalent… But again, you can spend very, very little money on this activity, this hobby, this sport... or you can spend a ton of money and that guarantees your ability to visit London.” —Matt (10:11)

• Alternatives and Charity:
  Some marathons allow runners to enter by raising money for charity, which Joel advocates as a more meaningful route.

2. Protein Powders & Health Product Hype

(11:22–14:10)

• Lead in Protein Powders:
  A recent Consumer Reports article claims some plant-based and chocolate protein powders have high lead levels; context provided on regulatory differences (California’s Prop 65 vs. FDA).

  “My biggest takeaway was the fact that the proteins that were plant-based had significantly higher amounts of lead...And in addition, the chocolate versions also have much higher levels.” —Matt (13:10)

• Smart Shopping:
  Matt recommends whey-based, budget-friendly protein from Aldi—but cautions: always check ratings when possible.

3. Do We Get Worse With Money as We Get Richer?

(14:10–19:44)

• Wall Street Journal Insights:
  As income rises, people often abandon the budgeting habits that built their wealth, leading to a surprising rise in “cash-strapped millionaires.”

  “People become more adept at like guesstimating or assuming things about their finances than they are at paying attention to the specifics.” —Joel (15:00)

• Moneyless Millionaires Defined:
  Millionaires with wealth “locked up” in real estate or retirement accounts have little liquidity.

  “Those dollars are tied up in retirement accounts. It’s tied up in home equity...those things are--they don’t just sell for your money.” —Matt (17:04)

• Roth IRA Hack:
  Roth IRA contributions are accessible tax and penalty-free (not investment gains), so regular contributors have flexibility if truly needed.

  “There is the possibility to access those funds...if you feel like a cash-strapped millionaire, your Roth contributions might at least make you feel less so.” —Joel (19:36)

4. AI Goes E-Commerce: Opportunity or Risk?

(19:44–22:16)

• Walmart & OpenAI Partnership:
  Walmart will soon allow shopping via ChatGPT, with OpenAI’s AI browser on the horizon.

  “I’m a little wary of this…I was talking to someone who was using ChatGPT for a home remodel project and she’s like, it’s giving me the best suggestions about all these things to buy. …it also just speeds up the process and makes it easier to spend in ways that are maybe a little more frivolous.” —Joel (20:45)

• Potential Risks:
  AI-enabled “frictionless shopping” could increase unintentional or unnecessary consumer spending and further challenge customer loyalty.

5. The Subscription Tsunami – Car Washes as a Case Study

(22:16–24:12)

• Car Wash Subscriptions Proliferate:
  One chain, Mr. Carwash, now gets 75%+ of revenue from recurring memberships.

  “Car wash locations are pricing their single washes...like a dollar less than the monthly subscription is, where it’s basically trying to tip you over into joining.” —Matt (21:34)

• Cautionary Note:

  “It’s in the best interest of that business, but not necessarily in yours. And so even if you don’t use the service, you’re still paying for it. So just pay attention to your finances and where your money is going.” —Matt (23:40)

6. Ludicrous Headline of the Week: “Wacky Labels Are Killing Craft Beer”

(27:42–33:33)

• Hosts’ Rebuttal:
  Joel and Matt refute a Times opinion blaming cartoonish branding for craft beer’s challenges, pointing instead to market oversupply, changing consumer habits, and shifting demand.

  • Quote:

    “We have this massive run up in craft breweries from essentially a handful to a handful in every city, and…consumer tastes have changed. So it’s not just that we’re drinking less craft beer, we’re drinking less in general.” —Joel (30:08)

• Parallel to Other Trends:
  Craft beer’s trajectory mirrors other fitness and consumer booms (e.g., CrossFit, boutique gyms), underscoring lessons about over-investing in trends.

7. Credit Card Churning: When Does It Make Sense?

(33:33–39:21)

• What is Churning?
  Opening multiple cards solely for sign-up bonuses; may yield thousands in rewards over time, but only for the hyper-organized.

  “This is like a 3000-level class…not Personal Finance 101.” —Matt (36:55)

• Risks & Rules:
  Major issuers like Chase implement “5/24” rules to block serial churners. The process demands careful attention to detail—otherwise, risk fees, lost points, or credit score dings.

  “It’s also important to note that churning can lead to a harmed credit score, especially in the short term. …if you’re trying to get credit soon, that can be a problem.” —Joel (37:45)

• Premium Card Inflation:
  The hosts remark on annual fees approaching $1,000 for “premium” cards—great for extroverted points-maximizers, but a peril for most people.

8. Health Savings Accounts (HSAs) & Prescription Savings

(39:21–43:11)

• HSA Eligibility Expands:
  High-deductible health plans now come with greater HSA access; hosts advise investing in an HSA if possible rather than cashing it out early.

  “HSAs are truly going mainstream. …if you are able, take full advantage by paying for health care costs out of pocket and then investing within the HSA.” —Matt (39:35)

• Prescription Vending Machines:
  Amazon’s new machines debut at OneMedical clinics for instant scripts, but hosts note Costco and Mark Cuban’s Cost Plus Drugs as cheapest prescription resources.

  “Maybe you get it and you pay a few dollars more because it’s so super duper convenient. But I think especially if you have a recurring prescription need, check those other guys out. Cost Plus Drugs being my favorite right now…” —Joel (42:06)

Notable Quotes & Fun Moments

• On Frugality in Running:

  “I do feel a special satisfaction when I’m passing someone in their $200 super shoes in my $30 Adidas shoes.” —Joel (07:52)

• On “Moneyless Millionaires”:

  “Those things [homes, 401ks] are…tied up in retirement accounts, it’s tied up in home equity. …those dollars are tied up. They don’t just sell for your money.” —Matt (17:04)

• On Subscription Logic:

  “Everybody wants you to have a subscription, but is that in your best interest? It’s worth thinking twice.” —Joel (23:56)

• On Credit Card Churning:

  “If you’re an accountant, you can probably pull this off. If you’re a baker…if you’re a coder…if you’re an influencer?...less so.” —Matt (36:45)

• On Over-Complication in Consumer Hobbies:

  “All you really need is a decent pair of shoes…and even just like a Kirkland Signature disposable water bottle…But now we’ve got super shoes, we’ve got high-end gels, we’ve got fancy watches, recovery tools…” —Joel (06:43)

Timestamps for Major Segments

• Running Industrial Complex: 05:30–11:22
• Protein Powder Controversy: 11:22–14:10
• Money Habits of Millionaires: 14:10–19:44
• AI & E-Commerce: 19:44–22:16
• Car Wash Subscriptions & Subscriptions Creep: 22:16–24:12
• Ludicrous Headline (Craft Beer): 27:42–33:33
• Credit Card Churning: 33:33–39:21
• HSAs & Prescription Vending Machines: 39:21–43:11

Conclusion

This episode encourages listeners to be intentional with money—regardless of income level—by resisting unnecessary spending pressures (from marathons to memberships), keeping healthy financial habits alive, and staying skeptical of one-size-fits-all consumer trends. Whether running a marathon, shopping through AI, or churning credit cards, Joel and Matt argue for clear-eyed self-assessment and relentless attention to where your dollars actually go. They close, as always, in friendship:

“Best friends out.”