Thirty-six hours before his wife was scheduled for a major surgery, New York Times personal finance columnist Ron Lieber got a letter in the mail that sent him reeling.

Insurance was denying prior authorization for the surgery. The only way forward would be to appeal the decision. But it was Saturday night, and the surgery was Monday morning. There wouldn’t be any time. Should they even go to the hospital?

They decided to bet on being able to reverse the denial later on, but the last minute coverage questions left Ron’s wife, New York Times reporter Jodi Kantor, going into surgery that Monday with a brand new sense of stress and anxiety.

And along with worrying how his wife's surgery would go (spoiler: it was successful), and whether they’d end up on the hook for a bajillion dollars, it left Ron to wonder why no one had given them a heads-up earlier.

He set out to find answers — and whether there might be a way to prevent these last-minute denials from sneaking up on other people.

Ron turned to his "Your Money" newsletter subscribers for ideas, and eventually published a draft letter in his New York Times column that doctors and other health care providers could give their patients to better prepare them for insurance curveballs.

Check out the column here – and consider passing it along to any health care workers whose patients you think might benefit.

Here’s a transcript of this episode.

Send your stories and questions. Or call 724 ARM-N-LEG.

Of course we’d love for you to support this show.

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For five years, we’ve been following the work of Dollar For and its founder Jared Walker, watching them quickly scale up their efforts to help people crush medical debt by tapping into “charity care” — the financial assistance that hospitals are legally required to offer some patients.

Their work represents what a small, scrappy, thoughtful group of people can do. Last year, their tiny staff helped wipe out more than $55 million in medical bills.

As we kick off 2026, we thought it was time to check in again. After all, this will be a year when millions more people will have trouble covering their medical bills — when Dollar For’s work may become more important to more people, and when we’re hungry for more ways to help each other.

As Jared tells it, 2025 proved to be a pivotal – yet rocky – period in the organization’s story. Both their successes and their challenges put into stark relief exactly what we’re all up against.

So we go deep with Jared on what they achieved while they weathered the chaos, and what it might mean for their – and our collective – next moves.

Here's a transcript of this episode.

Check out our Starter Pack: How to wipe out your bill with charity care.

And our previous coverage of Dollar For:

• Could billions in medical debt get zapped by the legal strategy from this 60-second video? (2021)
  We talked to Jared just weeks after Dollar For first went viral. The group’s early history — they’d been working locally for years — is fascinating.
• Badass volunteers help Jared level up, in the fight to crush medical debt (2021)
  Within six months, they’d recruited volunteers and built systems.
• The Medical Bill “Negotiation Lab” (2022)
  In an experiment aimed at scaling up impact, Dollar For tried a different approach in 2022. We sat in.
• One last tip before 2024 (2023)
  Why Jared thinks you should ask for “charity care” by name -- even though, let’s face it, asking for “charity” does not feel good to most of us.
• New lessons from the fight for charity care (2024)
  Dollar For spent 2024 focusing on the big picture and starting to focus on policy advocacy.

Check out our history of charity care series (from 2021):

• A legendary lawyer sued hospitals for price-gouging their patients. And got his butt handed to him.
  Dickie Scruggs is the guy who beat Big Tobacco. But when he took on hospitals, he lost.
• The wild backstory of a tiny but crucial Obamacare provision (ft. David Axelrod)
  Charity care wasn’t part of federal law until the Affordable Care Act passed. A Republican senator made sure it was part of the ACA — before deciding he wouldn’t vote for the law.
• “We just kept right on pushing” … and laws changed
  In New York, a grieving family’s story made headlines and helped advocates catch lawmakers’ attention.
• Wait, that was legal until now?!
  In 2021, Maryland barred hospitals from suing patients who qualified for charity care.

Send your stories and questions. Or call 724 ARM-N-LEG.

Of course we’d love for you to support this show.

See omnystudio.com/listener for privacy information.

Hey, first! If you value what we do, we need your support to keep it going in 2026.

We have SO much work ahead, and we can’t do it without you.

Every little bit counts. Here’s where you can chip in. Thank you SO much!

Our listeners have been teaming up on an incredible project – kicked off earlier this year by a med student named Thomas Sanford.

The idea: create a list of reliable resources to help with medical expenses and avoid debt, and circulate it where people might find it useful, like hospital waiting rooms.

In this episode, we hear how that project is ready to level up – and how you can bring it to people in your community.

Here’s how to help:

Send this link to anyone you think might need it: armandalegshow.com/help

Or go here to print it out, post it, pass it around, customize it for your community, or join with other volunteers: armandalegshow.com/helpers

See omnystudio.com/listener for privacy information.