How To Money – Episode #1066: Filing a Claim for a New Roof, Rebalancing Away from Tech/AI, & Taking Advantage of a Health Reimbursement Arrangement

Date: November 24, 2025
Hosts: Joel & Matt
Podcast: How to Money (iHeartPodcasts)

Episode Overview

In this “Ask HTM” episode, best friends and co-hosts Joel and Matt tackle a new round of listener questions. They focus on three main topics:

• The ethics and financial implications of getting a “free” roof through insurance
• Rebalancing investment portfolios away from tech/AI in light of industry trends and personal risk
• Understanding and maximizing Health Reimbursement Arrangements (HRAs) versus HSAs

The episode blends practical financial guidance, ethical considerations, and a healthy dose of the hosts’ characteristic banter—plus, impromptu discussions about mustaches and bourbon barrel–aged beer for good measure.

Key Discussion Points & Insights

1. The “Free” Roof via Insurance Claim — Ethics & Consequences

Listener Question

Tim from Illinois asks about companies offering “free roofs” after storms—should you take advantage since everyone’s rates go up anyway, or is it unethical?

Discussion Highlights

• Pervasiveness of Offers: Both hosts receive frequent unsolicited texts/flyers from roofing companies promising insurance-funded replacements.
• Ethical Dilemma:
  • Filing a dubious claim is likened to taking shampoo bottles from hotels: just because you can, doesn't mean you should.
  • Joel: “Would you feel OK knowing you got a new roof even though you didn’t have real damage? It feels like cheating.” [13:10]
  • Matt: “If everyone does it, it leads to higher rates for all. It's why we can't have nice things.” [14:28]
• Quality Risks:
  • Many companies are “fly by night” operations chasing insurance payouts with little accountability.
  • These companies may provide shoddy work—less incentive for quality since they don’t rely on long-term local reputation.
• Financial Consequences:
  • Filing a claim you don’t really need will increase both deductibles and future premiums (affecting your Clue Report and ability to shop insurers).
  • “If you truly experienced hail damage and you need to file a claim, do it. But if it’s a bogus claim just to get a new roof, don’t.” – Joel [14:10]
• Personal Responsibility & Collective Action:
  • The tendency toward “lawfare” and gaming the system is contrasted with simply doing the right thing.
• Big Takeaway:
  • Only file an insurance claim for genuine damage—financial and ethical consequences make “gaming” the system a losing proposition.

Key Quotes

• “This is why we can’t have nice things.” — Matt [14:28]
• “Just because everyone else is jumping off a bridge, doesn’t mean you should do it too.” — Joel [12:15]

2. Investing: Rebalancing Away from Tech/AI & International Diversification

Listener Question

Steve is in “Coast FI” and wonders about shifting new investments away from tech/AI-heavy funds (e.g., VTSAX/US markets). Is he overthinking the AI bubble, or is it smart risk management?

Discussion Highlights

• Current Situation:
  • Steve and wife maximize their retirement contributions early each year. He’s concerned about forced, early retirement if AI wipes out his business and is wary of an “AI bubble” in market performance.
• Not Market Timing:
  • Matt clarifies: “This isn’t knee-jerk market timing. Steve’s risk profile is genuinely changing as he gets nearer to wealth preservation.” [38:31]
• Diversification Strategies:
  • Recommends gradually shifting new investment dollars (not selling everything at once) into value or international funds to balance tech/AI exposure.
  • “Slowly, gently moving the rudder as opposed to jerking the wheel.” — Matt [39:23]
• Emotional Clarity:
  • Visualize your portfolio after a 30% drop or gain to assess your risk tolerance.
  • “Doing these thought exercises could be really beneficial… not just imagining the win, but the loss.” — Joel [43:02]
• Cash Reserves:
  • As retirement approaches (planned or unplanned), holding extra cash is wise to avoid drawing on your portfolio in a downturn.
• Bottom Line:
  • Given Steve's risk of earlier-than-expected retirement and tech concentration, it is sensible to rebalance toward less tech-centric, more international and value funds over time.

Key Quotes & Moments

• “Your goal isn’t to maximize returns as much as possible; it’s to be prepared for upcoming changes.” — Joel [41:12]
• “The risk tolerance part is super important, and this is why it’s such a personal decision.” — Matt [41:28]
• “If things go poorly, you might be in business longer. If things go well, you’re ready for early retirement.” — Matt [37:12]

3. Rothification & Retirement Account Strategies

Listener Question

Vicki from Ohio, making ~$69K/year, maxes out her HSA & Roth IRA. She wants to know about converting a 401(k) to Roth to further “Rothify” her savings.

Discussion Highlights

• Kudos:
  • Both hosts celebrate how much Vicki sets aside: “You are a total boss!” — Joel [21:58]
• 401(k) Roth Conversion:
  • Check for Roth 401(k) Option First: ~90% of employers now offer it—use this if available.
  • If Not: May be eligible to roll over traditional 401(k) funds to a Roth, depending on plan rules (look up “in-service rollovers”). Be mindful of the tax hit!
• Tax Consequences & Timing:
  • Carefully plan Roth conversions to manage the tax bill, possibly spread conversions over several years.
  • Consider waiting until income drops (e.g. after retiring) for more favorable conversion rates.
• Taxable Brokerage Accounts:
  • If all tax-advantaged accounts are maxed, investing via a taxable account is still worthwhile.
• Catch-Up Contributions:
  • Reminder for older listeners: additional contributions allowed after age 50.

Notable Quotes

• “If you can do a Roth 401k, that’s the simplest path forward.” — Matt [25:28]
• “Just know you are not getting a deduction for your 401k contributions if you convert.” — Matt [27:09]

4. Understanding Health Reimbursement Arrangements (HRAs)

Listener Question

Angela asks why HRAs aren’t discussed more on the show, and how they compare to HSAs.

Discussion Highlights

• Scarcity: HRAs are less common than HSAs or 401(k)s, so rarely mentioned.
• How HRAs Work:
  • Fully funded by the employer for employee healthcare expenses; employees submit receipts for reimbursement.
  • Money belongs to employer and may not be portable if you leave or unused by year-end.
• Can You Combine with HSA?
  • Sometimes, but depends on HRA version (“limited purpose” HRAs work with HSAs; standard HRAs generally don’t).
• Maximize the Perk:
  • Use up available HRA dollars before year-end or prior to leaving a job.
  • If both options are available, weigh employer generosity and your personal/family needs.

Notable Quotes

• “If you have a really generous employer offering a substantial reimbursement for you every year, that's a pretty sweet perk that I'd want to take full advantage of.” — Joel [55:43]

5. Bank Switching for Higher Yield Savings

Listener Question

Jordan wonders about chasing higher yields by moving money between online banks as rates change.

Discussion Highlights

• Host Experience:
  • Matt has been with Ally for nearly 20 years; both appreciate great customer service and features.
• Soft-Switching as a Middle Ground:
  • Moving a portion of your savings (not all your banking) to a higher-rate account can make sense (“soft-switching”) rather than going through the hassle of a full switch for marginal gains.
• Consider the Actual Benefit:
  • For a difference of 0.5% APY on $20k, the upside is limited; balance the hassle with the real reward.
• Pro-Tip:
  • “Not an irreversible decision. Give it a shot, see if it feels worth it. If not—you can undo it.” — Matt [50:54]

Fun & Notable Moments

• Banter on Facial Hair:
  • The duo spent the first few minutes riffing on growing (or not growing) mustaches and receiving compliments—or spousal pushback. [02:00–03:30]
• Beer Review:
  • Shared a “Bourbon Barrel Aged Imperial Stout Vintage Ale” by Kirkland Signature/Deschutes. Both were surprised by its quality, calling it “high-quality, with unique holiday spices, perfect for Thanksgiving.” [57:38–59:44]
• Pop Culture & LOTR:
  • Jokes about AI companies naming themselves after Tolkien fantasy objects (“Palantir, Anduril”) and whether they understood the original message. [05:10–05:42]
• Good-Humored Age References:
  • “You made yourself sound old yet again, Joel.” — Matt [24:40]
• Celebrity Nicknames:
  • Listener Jordan refers to the hosts as “Mole” and “Jat,” to their amusement. [48:24–48:39]

Important Timestamps

• 06:54 – Introduction to listener questions
• 07:52–17:10 – Roof insurance claims: Ethics and consequences
• 20:54–30:42 – Rothification of retirement savings
• 31:04–43:39 – Portfolio rebalancing away from tech/AI, hedging, and diversification
• 52:15–56:10 – Health Reimbursement Arrangements (HRAs) explained and compared to HSAs
• 57:38–59:44 – Kirkland Signature Vintage Ale Beer Review

Summary Table: Pros & Cons of Key Topics

| Topic | Pros | Cons | |-----------------|---------------------------------------------------------|-------------------------------------------------------------| | "Free" Roof Claim | Save money on roof, common industry practice | Unethical if not warranted, raises rates, affects insurability | | Rebalancing Portfolio | Reduces risk, aligns with real-life changes | May miss out on tech gains, more complicated than "set and forget" | | HRAs | Employer-funded, tax-free, low-effort for employee | Not portable, less flexible vs. HSAs, less common/offered | | Bank Hopping | Higher yield possible | Time-consuming, often small gains unless a lot of cash | | Roth Conversions| Tax-free retirement withdrawals | Tax implications in conversion year, must plan timing carefully |

Final Thoughts

This episode is a classic “How to Money” showcase—straightforward, practical money advice filtered through both financial and ethical lenses, always encouraging listeners to take the responsible, long view. The hosts combine real-life anecdotes, transparent opinions, and guest references to give their answers texture and relatability, with lots of humor throughout.

Hosts’ Core Message:
Make financial choices that serve your whole self—not just your wallet, but your community, your conscience, your future security, and your sense of peace.

Further Resources:

• EconTalk episode on the ethics of frugality: Shampoo bottles at hotels ([09:02–10:33])
• Interview with Joe Davis (Vanguard): The impact of AI and risk tolerance ([34:13–35:43]; see show notes for link)
• Visualizing risk tolerance technique: “Imagine your portfolio down 30%” — [41:28–43:39]