How to Money, Episode #1102: Listener Questions — Student Loans in Forbearance, Gaming Medical Debt Collections, and Financial Infidelity

Hosts: Joel & Matt (iHeartPodcasts)
Date: February 16, 2026

Episode Overview

In this engaging listener Q&A episode, best friends and hosts Joel and Matt tackle real-life money dilemmas sent in by How to Money listeners. They dive deep on:

• Strategies for handling medical bills, including using collections to negotiate better discounts
• Navigating student loan forbearance (especially for public service loan forgiveness) during uncertain times
• Maximizing the benefits of HSAs for future reimbursement of family medical expenses
• Financial infidelity in marriage—how to respond when a spouse racks up secret debt
• A Money Gear 7 listener expecting a first baby seeking advice on preparing for parenthood

Throughout, Joel and Matt stick to their signature jargon-free, approachable style, mixing practical advice with relatable humor and just a bit of geeking out over cloud photo storage.
Skip straight to the segments with timestamps and find the most useful takeaways and memorable quotes below.

Key Discussion Points & Insights

[01:07] Main Q&A Kick-off and Casual Chat

• Joel and Matt open the show answering listener questions ranging from healthcare costs to financial infidelity.
• The duo riff on cloud photo storage, discussing thriftiness vs. convenience—a light intro into the value-driven mindset they apply to money as well.

[09:51] Frugal or Cheap? Gaming the Hospital Collections System

Listener: Daniel from Salt Lake City

The Situation

• Daniel is facing $10,000+ in recent medical bills.
• After being denied financial assistance, he is offered only a 10% discount from the hospital.
• The internal billing agent suggests waiting until the debt moves to internal collections, where discounts may reach 30–70%, as the debt is not reported to credit bureaus in the first year.

Advice & Analysis

• Joel & Matt highlight the 12-month grace period before medical debt can hit one's credit, emphasizing the power patients have to negotiate during that window.
• Key Point: It’s not “cheap” but “savvy” to use this period strategically—doing so won’t hurt your credit as long as you stay within the year.
• They warn of aggressive collection letters and stress not to let fear force an early, larger payment.
• Negotiation Tactics:
  • Let the account age to maximize leverage.
  • Target a 30–50% discount in internal collections; 10% is “junk” (Matt, 11:14).
  • Prepare to play “game of chicken” with billing — patience pays here.

Notable Quotes

• Matt (13:38): “It’s like a game of chicken… the closer you get to the end of that, they’re thinking: ‘Oh my gosh, this guy may not actually be able to pay, so we’re willing to take less.’”
• Joel (14:51): “Wait a second, you charged me how much for that aspirin?... You can push back on that.”

[Summary Guidance]

• Wait out the process (up to a year) to maximize reduction.
• Don’t pay out of fear; know your rights and deadlines.
• Use the extra time to comb through bills for errors or overcharges.
• Consider the potential for 30–50% (sometimes more) off the original bill.

[21:18] Student Loans Still in Forbearance? PSLF & Payment Strategy in Limbo

Listener: Adam from Chicago

The Situation

• Adam’s student loans are in administrative forbearance (no payments required).
• He qualifies for Public Service Loan Forgiveness (PSLF) and is using the payment pause to aggressively pay off a 0% credit card balance transfer.
• Unsure if/when to resume student loan payments, or whether he should switch repayment plans to stay PSLF-eligible.

Advice & Analysis

• Big Win: Smartly using the pause to clear high-interest debt—not inflating lifestyle or spending.
• Don’t worry about a growing loan balance if you’re on track for full PSLF; the forgiven balance is what matters, not interim interest.
• PSLF Unlikely to Disappear: Existing participants are protected; “you’re not going to get kicked out of something you’re already in." (Matt, 25:20)
• Practical Steps:
  • Stay in your current SAVE plan for now.
  • Don’t rush to make payments before you must, especially while paying off 0% debt.
  • Build a cash buffer for when payments restart.
• Bonus Tip:
  • Check out the PSLF Buyback Program if you’re close to the 120 qualifying payments; you can retroactively “buy back” missed months with calculated payments.

Notable Quotes

• Joel (23:28): “As payments have restarted… it has put so many people in an even worse financial predicament because they got used to incorporating that student loan payment back into their budget.”
• Matt (26:25): "There's no point in moving to a different repayment plan earlier than is necessary, especially with potential for some of these months in forbearance to count."

[Summary Guidance]

• Prioritize eradicating high-interest credit card debt during forbearance.
• Don't stress about PSLF changes—the program is secure for existing borrowers.
• Sit tight in your current plan; transitions will be announced, and you won't be penalized for optimizing your cash flow in the meantime.

[29:48] Maximizing HSA Reimbursements—Does Coverage for Kids Stick Once They’re Grown?

Listener: Abby from Iowa

The Situation

• Abby and her husband are in their late 30s, maxing out their HSA and stockpiling medical receipts for future tax-free withdrawals in retirement.
• She wants to ensure she can still reimburse herself for her kids’ medical expenses (e.g., braces at age 8) even when they are long past age 26 and no longer on her insurance.

Advice & Analysis

• Eligibility is Locked at Time of Expense:
  • As long as your child was your dependent when the bill was incurred, you can reimburse decades later—even if she’s 38, not 8!
• Critical Recordkeeping:
  • Keep digital receipts and documentation showing the relationship (tax returns, etc.) for future audits.
  • A spreadsheet or using AI to track dates, descriptions, amounts makes handling this in 20+ years easier.
• Why This Rocks:
  • Grown HSA balances can be tapped tax-free, decades after the fact, for any eligible expense incurred while you/your spouse/dependents were covered.

Notable Quotes

• Joel (33:08): “It's a really cool account if you use it like a health savings account, like as prescribed... but it's super duper extra cool if you invest and you're like growing a stockpile of money that never gets taxed.”
• Matt (35:40): “Regardless of what the future holds… Absolutely. 100% yes, those [old] expenses qualify.”

[Summary Guidance]

• Yes, keep those braces receipts—you can cash them in tax-free decades later!
• File receipts securely, log details, and maintain proofs of dependency.
• The HSA is “retirement account on stealth mode” when handled this way.

[43:03] Tips for Expecting Parents Already in Money Gear 7

Listener: Tara (Facebook Q)

The Situation

• Tara and her husband are expecting their first baby, already in excellent financial shape (Money Gear 7) and have a hospital bill savings bucket established.

Advice & Analysis

• Estimate hospital costs with your insurer and save accordingly.
• Consider starting a 529 plan (education fund), but don’t go overboard—starter contributions get the tax clock rolling.
• Leverage your earned financial flexibility: take (and savor) time with your child—memory-making has more long-term impact than piling up more money.
• Don’t chase more financial goals at expense of being present with your new family.

Notable Quotes

• Matt (45:25): “Give yourself permission to spend as much time with that baby as you want... It's your presence, not presents.”
• Joel (47:34): "Act like you're in Money Gear 7 ... don't waste that optionality when these are precious times."

[47:35] Facing Financial Infidelity: When a Spouse Racks Up Hidden Credit Card Debt

Listener: Anonymous

The Situation

• Over the holidays, Anonymous's wife secretly accumulated $6,000 in debt (not her first time); she’s in therapy, and now they’re restricting new credit card use to joint agreement.
• Husband feels frustrated after months building an emergency fund, now wiped out.

Advice & Analysis

• Addiction is Real: Don’t ignore the compulsive/dopamine “hit” nature of online shopping—similar to gambling/addictions made easier by tech and frictionless purchases.
• Immediate Practical Steps (if spouse is willing):
  • Remove saved billing info from browsers, phone, websites (e.g., Amazon one-click).
  • Consider freezing credit with all bureaus to prevent new card openings. “Make sure that junk’s frozen.” (Matt, 53:04)
• Emotional Dynamics: Shame is not an effective motivator—scorn will likely entrench behavior.
  • Seek shared counseling (not just therapy for the shopper).
  • Remember, “You’re on the same team”—work the problem together.
• Analogy:
  • Matt (54:18): “If he always got drunk and then drove somewhere... you'd ask your wife to take the keys from you.”

Notable Quotes

• Joel (54:41): “The more you make her feel ashamed… the pattern is going to repeat, right. Because shame is cyclical in that way.”
• Matt (53:02): “If your credit is frozen, she cannot open...”

[Summary Guidance]

• Address the spending with empathy and cooperation, not blame.
• Tactically, make access to impulsive credit harder (with their buy-in).
• Counseling together may be the best (and only) way to break the cycle—finances are deeply intertwined with emotions and relationship health.

Memorable Quotes

• Matt, on medical bills: "The entire healthcare system is a bit sketchy. And in this case, we’re going to side with the patients, not the hospitals." ([13:48])
• Joel, on HSA magic: “That completely avoids the tax, man. That’s what makes it, like on steroids, superpower, supercharged.” ([33:08])
• Matt, on PSLF stress: “You’re not going to get kicked out of something you’re already in.” ([25:20])
• Joel, on presence vs. presents: "It’s really easy to think I gotta do more, I can keep doing more... [but] you have a lot of optionality—don’t waste that." ([47:34])
• Joel, on financial infidelity: "Working through it together with the help of a third party could save your marriage and could save your finances." ([55:49])

Episode Timestamps & Segments

• [01:07] Episode start: Listener question intro, hosts banter on cloud photo storage
• [09:51] Frugal vs. Cheap: Using collections to lower hospital bills
• [21:18] Student loans in forbearance & PSLF strategy in uncertain times
• [29:48] HSA account deep dive—using receipts decades later for kids’ medical expenses
• [43:03] Financial tips for expecting parents in strong financial shape
• [47:35] Financial infidelity: How to respond to a spouse’s hidden spending

Final Notes

Joel and Matt deliver actionable advice on tricky money dilemmas, all while keeping it authentic, accessible, and often funny. Whether you’re trying to outsmart hospital billing departments, maximize your HSA’s superpowers, or dealing with tough relationship challenges around money, their guidance bridges practical tactics and underlying emotional realities.

Contact: Got your own money question? Record a voice memo and send it to howtomoneypodmail@gmail.com – you might be featured on a future show!

Best friends out.