261. Save Money on Medical Bills and Navigate Health Insurance Like a Pro with Dan Weissmann

Summary of 261. Save Money on Medical Bills and Navigate Health Insurance Like a Pro with Dan Weissmann

by Her First $100K

1h 9m•November 11, 2025
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Overview of Financial Feminist — Episode 261: Save Money on Medical Bills and Navigate Health Insurance Like a Pro with Dan Weissmann

Tori Dunlap interviews journalist and host Dan Weissmann (An Arm and a Leg) about why U.S. healthcare feels rigged, how costs flow to insurers/pharma/hospital chains, and—most importantly—practical, concrete steps listeners can take to lower bills, choose better insurance, and challenge denials. The episode covers open enrollment tips, Medicare and Medicare Advantage realities, risks to Medicaid from new rules, how to dispute and negotiate medical bills, ways to save on prescriptions, and where to get free help (SHIP, charity care resources, community clinics).

Key takeaways

  • U.S. healthcare is highly profit-driven and consolidated; patients often enter an uneven playing field with insurance companies, pharma, and hospital systems that have legal/financial teams designed to maximize revenue.
  • Don’t choose a plan only by lowest monthly premium—calculate expected annual costs (normal-year use) vs worst-case scenarios and check provider/hospital networks and drug formularies.
  • Medicare is not “free.” It has premiums, deadlines (late-enrollment penalties), gaps (vision/dental), and trade-offs between traditional Medicare + Medigap vs Medicare Advantage (which can limit access and be hard to reverse).
  • Medicaid re-determinations and proposed work requirements increase administrative burdens and risk millions losing coverage; bureaucracy often knocks people off coverage over paperwork errors.
  • Many medical bills contain errors or weren’t billed to insurance—always verify and appeal. Nonprofit hospitals are required to offer charity care/financial assistance; many patients qualify.
  • There are multiple ways to lower prescription costs (GoodRx, Cost Plus Drugs, price shopping, generics, manufacturer coupons, appeals and samples). Building a simple comparison spreadsheet helps.
  • Use free counseling and advocacy resources: SHIP for Medicare, hospital charity care pages (and consolidated databases), community/federally qualified health centers, and patient-directed guides/newsletters.

Practical steps — what to do and ask

Choosing during open enrollment

  • Don’t default to the lowest premium. Make two quick calculations:
    1. “Normal-year” costs: expected doctor visits, prescriptions, mental health, planned procedures, and preferred providers (check network).
    2. “Worst-case” risk: deductibles, co-insurance %, and out-of-pocket maximums if you have a major event.
  • Check provider/hospital networks and verify your specialists are “in network.”
  • Check the drug formulary for each plan: use Control+F to find your meds and their tiers/copays.
  • Consider whether the plan’s out-of-pocket and coinsurance exposure is acceptable for your budget.

Medicare (preparing for 65+)

  • Medicare is not automatically free—premiums, deductibles, and gaps exist.
  • Decide between traditional Medicare + Medigap vs Medicare Advantage:
    • Traditional Medicare gives broader access but often needs a Medigap supplement and separate Part D for drugs.
    • Medicare Advantage can have low/no premiums and extra benefits but is run by private insurers, may restrict providers, and can be harder to switch away from later.
  • Use SHIP (State Health Insurance Assistance Program) for free, unbiased one-on-one counseling—very useful for navigating choices and annual drug-plan reviews.
  • Be aware of enrollment deadlines: late sign-ups can hit you with permanent penalties.

Medicaid & policy risks

  • Administrative burden (paperwork, missed notices) is a key reason people lose Medicaid.
  • Proposed work requirements and tightened re-determinations increase the risk of losing coverage; vulnerable populations may struggle to comply with new rules.

Evaluating a job’s insurance benefit

  • Ask HR for plan documents, the drug formulary, and the effective date for coverage.
  • Know how much the employer covers of premiums (e.g., 85% is generous) and when coverage begins.
  • Consider that employer-paid premiums are part of your total compensation—valuable, but also a component of employer budget.

At the doctor / before procedures

  • Come prepared with a written list of questions.
  • Ask about alternatives, risks, success rates, and how many times the provider has performed a procedure.
  • Don’t sign up for major procedures in the first conversation—get second opinions for big decisions.
  • Ask upfront about likely costs and whether the service is in-network.

How to fight, reduce, or negotiate medical bills

  • Get an itemized bill (super bill) and reality-check each code and charge. Common errors include services never performed or not being billed to insurance.
  • Ask whether the provider billed your insurance. If not, ask them to bill it.
  • Apply for charity care/financial assistance (nonprofit hospitals are required to offer it). Use hospital policy pages or aggregated resources to find thresholds and application steps.
  • If eligible, apply for charity care before or soon after treatment to limit collections.
  • Appeal insurance denials—many people win appeals but most don’t bother to try.
  • If you can pay a lump sum, offer full payment in exchange for a discount (billing departments often prefer a sure payment).
  • Tell your story—if you’re in financial distress, billing offices often have hardship programs; advocacy and persistence work.

How to save on prescriptions

  • At the pharmacy counter, check:
    • Cash price vs insurance price (sometimes paying cash + coupon is cheaper).
    • GoodRx and similar coupon sites (and competitors).
    • Mark Cuban’s Cost Plus Drugs for low-priced generics.
    • Legit Canadian pharmacies vetted by PharmacyChecker (be cautious—use verified sources).
  • Ask your doctor about therapeutically equivalent, cheaper alternatives.
  • Ask your provider for samples to bridge time while appealing insurance denials.
  • Build a simple spreadsheet comparing prices across local pharmacies and coupon sites for recurring meds.

Options if you’re uninsured or underinsured

  • Apply for hospital charity care/financial assistance (and try to do it before care if possible).
  • Federally Qualified Health Centers / community clinics provide sliding-scale care and accept uninsured patients—search for nearby centers.
  • Negotiate payment plans or hardship discounts with hospitals and providers.
  • Use aggregated resources (see below) and local legal/patient-advocacy groups for help.

Notable quotes & metaphors

  • Dan Weissmann: “We’re not just playing against the house. We’re kind of being ushered straight to the table where the World Series of Poker is being played… We are the sucker at the table.”
  • Core insight: the system is engineered to prioritize investors and shareholders; many structures (formularies, PBMs, clinical trial funding models) incentivize very high prices.

Action checklist (quick)

  • During open enrollment: compare total expected annual cost (premiums + expected out-of-pocket), verify providers are in-network, check drug formulary.
  • If you get a bill: request an itemized/super bill, confirm insurance was billed, ask about charity care, appeal denials, request discounts for lump-sum payment.
  • Prescription issues: check GoodRx / Cost Plus / local pharmacies, ask providers for alternatives or samples, build a price comparison spreadsheet.
  • Approaching Medicare: schedule a SHIP appointment, learn deadlines, weigh traditional Medicare + Medigap vs Medicare Advantage.
  • If uninsured: find community clinics or apply for charity care at hospitals ahead of time.

Resources mentioned

  • Dan Weissmann’s podcast and site: An Arm and a Leg (armandalegshow.com) — newsletter: First Aid Kit
  • SHIP (State Health Insurance Assistance Program) — free local Medicare counseling
  • GoodRx (price comparison / coupons)
  • Mark Cuban’s Cost Plus Drugs (Cost Plus Drugs)
  • PharmacyChecker (verifies international pharmacies and price comparisons)
  • Hospital charity care pages / Dollar Four (resource referenced for charity-care policy aggregation)
  • Her First $100K / Financial Feminist show notes: herfirst100k.com/ffpod (episode resources, guides)

For people facing a confusing bill or coverage decision: verify the charges, don’t accept “no” without appeal, use charity-care programs if eligible, and lean on free counseling (SHIP) or community clinics. Dan’s reporting and "An Arm and a Leg" newsletter offer many starter packs and templates for common problems like “I got a giant bill” or “insurance denied my claim.”