How to Money — Friday Flight: Forever Mortgages, Ruining Reward Cards & Free Tax Filing Fail

Podcast: How to Money (iHeartPodcasts)
Hosts: Joel & Matt
Date: November 14, 2025
Episode: #1062

Episode Overview

Joel and Matt's latest Friday Flight tackles a week’s worth of hot personal finance headlines with their characteristic humor, skepticism, and practical advice. This episode covers the long-term impacts and pitfalls of the proposed 50-year mortgage, changes coming for credit card rewards thanks to a major Visa/Mastercard settlement, the government’s failed attempt at free tax filing, and more. Throughout, they advocate for transparency, long-term financial health, and keeping scams at bay—even if it means setting up a family code word à la Harry Potter.

Key Discussion Points & Insights

1. The 50-Year "Forever Mortgage" Proposal

(Starts ~03:33)

• Summary:
  The Trump administration has floated allowing Fannie and Freddie to back 50-year mortgages.
• Hosts’ Take:
  Matt is not a fan—comparing it to overly long car loans and calling it “a short-term fix to a long-term problem.” The reduced monthly payment is minor, while the lifetime interest cost and slow principal paydown are huge.
• Issues Highlighted:
  • Unlikely people will stay in a home for 50 years, so when you move, you will have paid off very little principal, risking being underwater or walking away with nothing.
  • Banks will likely charge higher rates due to increased risk.
  • Joel jokes, “Why stop at 50? Maybe 100-year mortgages. Why not?” (07:29)
• Memorable Quote:
  • Matt: “Making longer debt instruments is a short-term fix to a long-term problem that has the potential to create even more long term problems down the road.” (06:01)

2. Robinhood’s Entry into Mortgage Lending

(09:27)

• Summary:
  Robinhood is planning to offer mortgages, initially to Gold members.
• Hosts' Take:
  • Emphasize always getting at least three mortgage quotes.
  • A four-minute mortgage application may be “too easy”—some friction is healthy for big decisions.
• Memorable Quotes:
  • Matt: “There’s a part of me that says, you know what, I think the friction is actually a good thing in this case.” (10:18)
  • Joel: “Applying for a mortgage shouldn't be like buying sneakers online.” (11:19)

3. Holiday Gift Spending Concerns & Practical Advice

(11:30)

• Headline: 79% of Americans are concerned about affording holiday gifts this year.
• Hosts' Advice:
  • Start saving for holiday gifts in January via a sinking fund (e.g., $40/month).
  • Set realistic budgets and have honest conversations with friends/family to set expectations now.
• Memorable Quotes:
  • Joel: "Make a gift recipient list and attach a reasonable budget for what you’re willing to spend for each person." (12:13)
  • Matt: "Do it now, because the closer you get to Christmas, the harder it’s going to become." (13:52)

4. Food Insecurity & Community Support

(14:22)

• Trigger: Uptick in people using GoFundMe for food and SNAP delays.
• Hosts’ Take:
  • Promote looking out for neighbors, participating in food drives, and using/helping others find resources at findhelp.org.
  • Matt: “Making people aware of those resources can be a big help, too.” (16:48)

5. Congress & Obfuscating Investment Fees

(17:52)

• Headline: Legislation could allow certain funds (e.g., business development companies, BDCs) to hide fees.
• Hosts’ Take:
  • Even if this doesn't impact mainstream funds (yet), it’s a slippery slope.
  • Transparency in investing fees is critical.
• Memorable Quotes:
  • Joel: “Give me a slippery slope.” (19:25)
  • Matt: “Anytime Wall Street tries to obfuscate fees… that’s where we start getting a little bit nervous.” (19:04)

6. Vanguard’s Behavioral Nudges for Investors

(20:10)

• Summary:
  Vanguard will nudge investors to avoid mistakes like leaving rollover IRAs in cash.
• Take:
  • This “a la Betterment” approach can prevent loss of compounding.
  • 28% of rollover assets in 2015 sat in cash for seven years!
• Joel: “Seven years of staying in cash… those folks would miss out on a ton of returns.” (20:35)

7. Visa/Mastercard Settlement: The Changing Face of Rewards Cards

(30:13)

• Headline: Visa & Mastercard agree to settlement allowing businesses to decline high-fee (high-reward) credit cards.
• Implications:
  • Small businesses may now refuse the priciest reward cards, affecting consumers who chase points.
  • Could lead to price surcharges for premium cards—or just flat-out refusal.
• Hosts’ Take:
  • Good for merchants’ margins, potentially awkward for cashiers and customers.
  • Could signal the era of “bougie travel” cards losing some perks or acceptance.
• Memorable Quotes:
  • Joel: “Your super high-end fancy credit card, I’m not taking that one because it costs me more money.” (32:01)
  • Matt: “Why should I have to pay for your access to the [airport] lounge when I don’t have that card?” (33:22)

8. IRS’ Free Tax Filing Experiment – A Fail

(34:24)

• Headline: IRS’s “Direct File” free tax filing system is shuttered after minimal adoption and high costs.
• Hosts’ Advice:
  • Recommend alternatives like Cash App Taxes for genuinely free federal/state filings.
  • Warn about tax scams and impersonation calls as tax season nears.
• Memorable Quotes:
  • Joel: “If someone calls pretending that they are the IRS… it’s totally fake, it’s totally bogus.” (37:48)

9. New Age Scams: Family Code Words

(37:55)

• Context:
  Rise of phone/voice scams and deepfakes—especially “grandparent” scams.
• Advice:
  • Set up a unique family code word for emergencies.
  • Reference to “Mollywobbles” from Harry Potter as a code word example.
• Joel: “A family code word is a very small, easy thing to do that could prevent you from a lot of heartache or getting scammed out of a bunch of money.” (40:41)

Notable Quotes & Moments

• On 50-Year Mortgages:
  • Matt (06:01): “Making longer debt instruments is a short-term fix to a long-term problem that has the potential to create even more long term problems down the road.”
• On Easy Mortgage Applications:
  • Matt (10:18): “There’s a part of me that says…the friction is actually a good thing in this case.”
• On Saving for Christmas:
  • Joel (12:13): "…attach a reasonable budget for what you’re willing to spend for each person you want to buy for."
• On Investment Fee Transparency:
  • Joel (19:25): “Give me a slippery slope.”
• On High-End Credit Card Fees:
  • Matt (33:22): “Why should I have to pay for your access to the lounge when I don’t have that card?”
• On Tax Scams:
  • Joel (37:44): “…it’s totally fake, it’s totally bogus. But it’s gonna hook a lot of people.”

Important Timestamps

• 03:33 – 50-Year Mortgages: Pros and (mostly) Cons
• 09:27 – Robinhood Enters Mortgage Market
• 11:30 – Holiday Gift Guilt & Budgeting
• 14:22 – Food Insecurity & GoFundMe
• 17:52 – Congress, Investments & Hiding Fees
• 20:10 – Vanguard’s Behavioral Nudges
• 30:13 – Major Credit Card Settlement: Rewards Cards’ Future
• 34:24 – IRS Direct File Tax Program Fails
• 37:55 – Scams & Family Code Words

Episode Tone & Highlights

• Language/Tone: Candid, witty, self-deprecating, and practical; supportive and community-oriented.
• Memorable Moments:
  • Joel’s joke about longer and longer mortgages.
  • Matt’s reluctance about mortgage applications being “too easy.”
  • Harry Potter reference for family code words.
  • Banter about beating the Stacking Benjamins in a charity challenge.

Actionable Tips & Advice

• Be wary of “solutions” that promise cheaper payments (e.g., 50-year mortgages): always crunch the total cost and know your exit plan.
• Always shop for rates—especially for major products like mortgages.
• Build holiday gift funds year-round and communicate spending limits early.
• Lead or participate in community support, especially in tough times.
• When investing, demand transparency in fee disclosures.
• Consider which credit card rewards actually serve you—change may be coming!
• For tax filing, stick with genuinely free services and be vigilant for scams.
• Set up a family code word to defend against evolving scams—no one is too smart to be targeted.

For more, visit How to Money.