Podcast Summary: How to Money

Episode: Ask HTM - Best Grocery Cashback Credit Cards, Risking it with Ultra Cheap Car Rentals, & Giving Up on Home Ownership #1039
Hosts: Joel and Matt
Date: September 22, 2025

Episode Overview

In this engaging Q&A episode, Joel and Matt tackle a slew of listener questions covering smart money moves with large cash windfalls, the ins and outs of grocery cashback credit cards, navigating the world of ultra-cheap car rentals, and how to handle Roth IRA contribution limits following marriage. True to their mission, they strike a balance between practical guidance and relatable, jargon-free conversation, providing actionable financial wisdom alongside real-life stories and humor.

Main Themes:

• Handling large lump sums after selling real estate, especially when opting out of homeownership.
• Maximizing grocery spending rewards with cashback credit cards, and coping with annual fees.
• Avoiding pitfalls with bargain-basement car rentals.
• Adapting investment strategies and Roth IRA contributions after a change in marital status.

Key Discussion Points & Insights

1. Should You Give Up on Home Ownership? (07:50–18:21)

Listener Hayden’s Situation:
Hayden and his wife sold their primary residence and are about to sell a duplex, netting ~$600k total. Both have strong retirement funding—including maxed-out work retirement plans and future NY state pensions. The question: What’s the smartest move for this sizable, unneeded cash?

Insights:

• Homeownership as Non-Essential:
  "I really appreciate... the fact that Hayden and his wife decided that owning a home just wasn’t for them." – Matt (08:47)
  The hosts validate renting as a viable and perhaps preferable lifestyle and financial choice for some, especially given flexibility and reduced stress.
• Renting Can Mean More Flexibility:
  Renting offers adaptability if life changes unexpectedly, and can be a cheaper option depending on market trends (10:24).
• Tax Implications of Selling:
  Gains on primary residences are tax-free, but large profits on investment property (like the duplex) will face a capital gains tax—plan to set aside ~15% (12:20).
• Possible Tax Strategies:
  Consider occupying the duplex before selling to avoid capital gains tax, if your lifestyle allows (13:13).
• What to Do With the Windfall:
  Prioritize reflection about family goals before acting. Consider options like a “mini retirement,” charitable giving (donor-advised funds), or investing in a taxable brokerage account for growth and flexibility.
  "You can essentially have your cake and eat it too." – Matt (15:03)
• Don’t Rush Decisions:
  Take time, discuss possibilities, and don't lock up your liquidity too quickly (15:48).
• Mini-Retirement, Philanthropy, or Investing:
  Choosing among these depends on your priorities and readiness for “audacious moves” without risk to long-term security (18:21).

2. Best Grocery Cashback Credit Cards (22:18–33:44)

Listener Roy’s Question:
Is it possible to repeatedly get annual fees waived on top-tier cashback cards, and at what point does requesting a waiver become "cheap" instead of frugal?

Insights:

• Savvy Use of Annual Fee Cards:
  If you spend at least $3,000–$6,000/year on groceries, the Amex Blue Cash Preferred’s $95 fee is more than offset by 6% back (28:20).
• No Shame in Asking for a Waiver—But Success is Rare:
  "There's no amount of charisma or justifiable evidence... they essentially say this is just how it works." – Matt (32:29)
  Credit card companies often won't grant repeated fee waivers when a no-fee product exists for downgrading.
• Optimize Your Cards:
  Use the Blue Cash Preferred up to the $6,000 annual grocery cap, then switch to the no-fee Everyday Blue Cash (33:18).
• Military Exception:
  Active duty military personnel often have annual fees automatically waived, even on very high-end cards (34:41).
• Frugal vs Cheap:
  Asking once is fine but expecting continuous waivers is unrealistic—leverage card downgrades smartly instead.

Notable Quote:
“There's no amount of charisma. There is no amount of justifiable evidence that I was able to provide...” – Matt (32:29)
"Ethical fatigue—I'm going to use that in the future." – Joel (24:55)

3. Ultra-Cheap Car Rentals—Deal or Disaster? (47:13–53:50)

Listener Matthew’s Question:
Should you trust car rental companies with bargain-basement prices when others charge hundreds more?

Insights:

• You Get What You Pay For:
  The lowest-priced companies often earn their reputation with poor service, hidden fees, and inconvenient locations.
  “You do, at times... get what you pay for. And those reviews, I think, are evidence.” – Joel (48:01)
• Review Quality Matters:
  Ignore bad reviews at your peril—even major brands can have bad local franchises (48:26).
• Paying More is Worth It—Sometimes:
  For travel, time, reliability, and peace of mind are often worth paying a bit extra (50:48).
• Book Smart:
  Use Costco Travel for reliable deals, and always reshop your booking as prices can drop before your trip (52:10).
• Alternatives:
  Turo and AutoSlash are mentioned for potential savings or better experiences.

4. Married & Exceeding Roth Income Limits—What Now? (35:44–43:40)

Listener Chelsea’s Question:
After getting married and filing jointly, Chelsea’s household income exceeded Roth IRA limits. What now, and what to do with earlier 2025 Roth contributions?

Insights:

• Celebrate Earning More—but Adapt Strategy:
  Exceeding Roth limits is a "good problem," signaling financial success (37:02).
• Backdoor Roth IRA:
  If you don't have a traditional IRA, consider non-deductible IRA contributions, then convert immediately to Roth. Watch out for the pro-rata rule if you have existing traditional IRA funds (39:41).
• Handling Ineligible Contributions:
  You must “recharacterize” excess Roth contributions—convert them to a traditional IRA and file IRS Form 8606 (41:09).
• Don’t Withdraw Contributions:
  Withdrawing can mean taxes and penalties; instead, fix the issue with proper paperwork.
• Why Not a Universal Roth?
  The hosts lament income restrictions and wish everyone could contribute regardless of income (43:21).

Notable Quote:
"Wishing everyone could contribute to a Roth IRA, no matter what their income." – Joel (43:25)

5. Debt Snowball vs. Avalanche (54:20–57:07)

Anonymous Poster:
Pay off cards with highest interest rates ("avalanche"), or start with the lowest balance for more motivation ("snowball")?

Insights:

• Avalanche = Lower Interest Paid:
  Mathematically optimal: pay off highest-rate debts first.
• Snowball = Emotional Wins:
  Paying off the smallest balances first fosters momentum and higher likelihood of staying motivated (55:25).
• Choose What Works for You:
  Most credit cards have similar high APRs, making snowball wins more psychologically compelling with little extra cost.
• Debt Consolidation:
  Options exist, but self-discipline and a clear plan trump most mechanical reshuffling strategies.

Other Notable Moments

The “Frugal or Cheap” Opener (03:06–06:42)

Fun banter on getting tattoos or ear piercings at deep discounts, with a lesson: only jump at a deal if it was already a thoughtful purchase.

Beer of the Week: Fat Pug Oatmeal Stout (07:55, 58:26–61:13)

The hosts share their opinions on the featured craft beer, debating whether it’s deliciously mellow or not noteworthy, using their characteristic blend of sincerity and levity.

Notable Quote:
"Beer is good for your heart. Just like Cheerios." – Joel (58:44)

Timestamps for Key Segments

• 07:50 – Hayden's homeownership windfall strategy
• 12:20 – Capital gains tax on duplex sale
• 15:48 – Why not to rush your big financial decisions
• 22:18 – Grocery cashback card strategy and annual fees
• 28:20 – Amex Blue Cash math & usage tips
• 32:29 – Reality of annual fee waivers: Matt's direct experience
• 34:41 – Military and annual credit card fees
• 35:44 – Married and over the Roth IRA limit: Next steps
• 39:41 – Backdoor Roth IRA & the pro-rata rule
• 41:09 – Recharacterizing excess Roth contributions (Form 8606)
• 47:13 – Evaluating ultra-cheap car rental companies
• 50:48 – Why paying more can be worth it for car rentals
• 52:10 – Using Costco Travel and reshop strategies for rental car savings
• 54:20 – Debt snowball vs. avalanche breakdown
• 58:26 – Fat Pug Oatmeal Stout beer review

Memorable Quotes

• "You can essentially have your cake and eat it too." – Matt (15:03)
• "There's no amount of charisma... there's absolutely nothing that we can do." – Matt, on trying to talk Amex out of an annual fee (32:29)
• “You do, at times... get what you pay for. And those reviews, I think, are evidence.” – Joel, on cheap car rental companies (48:01)
• "Celebrate earning more—but adapt your strategy." – Joel (37:02)
• "It's really a question of math versus your brain." – Joel, on debt paydown strategies (54:20)
• "Beer is good for your heart. Just like Cheerios." – Joel (58:44)

Tone and Language

• Conversational, friendly, humorous, and encouraging
• Non-judgmental, practical, and realistic about money decisions
• Occasional gentle sarcasm, especially about financial myths and societal expectations

Conclusion

A lively, information-packed Ask HTM episode that proves even complex financial moves—handling windfalls, optimizing credit cards, strategic renting, and navigating retirement account rules—are approachable with the right mindset and clear advice. Joel and Matt mix actionable tips with thoughtful guidance that centers lifestyle happiness, flexibility, and doing what's right for your own situation.

Show notes and resources available at howtomoney.com — including calculators, articles about backdoor Roth IRAs, and more.

Best Friends Out!