Sh**’s wild’: Scaling up, doubling down, and buckling in

Hey there—

Our plan for today’s new podcast episode was simple: Check in with the founder of a scrappy organization that’s been inspiring us for five years to hear about their 2025 triumphs and their plans for 2026.

That organization would be Dollar For, a nonprofit that helps people crush medical bills by connecting them with charity care — financial assistance that hospitals are legally obligated to offer some patients (but often don’t).

In 2021, Dollar For’s recognition blew up — instantly transforming from a local organization serving Portland, Oregon, to a national force — when founder Jared Walker went viral on TikTok, reaching millions of people with (a) the news that charity care is a thing, and (b) an offer to help folks apply.

“I’m excited,” Jared told me a few weeks in. “We’re gonna help a lot of people, and hopefully we can get some funding to scale what we’re doing because: shit’s wild.”

Ever since, it’s been inspiring and eye-opening to watch Jared and his colleagues go at it — quickly expanding their impact and ambition, and learning as they go. Which is why we’ve followed up with them so many times.

So this seemed like a great time to check in. After all, 2026 is going to be a challenging year: With Obamacare premiums skyrocketing, lots of folks will end up without insurance, or with worse insurance, or with more-expensive insurance that may also be worse.

It’s a good moment to grab some inspiration.

How they forged ahead through rocky terrain

And I already knew about some of Dollar For’s recent triumphs: They helped people wipe out $55 million in medical bills last year — a $22 million increase from the year before.

But as Jared told me, 2025 had also been a tough, tumultuous year for Dollar For.

Early on, two major donors pulled out — prompted by what they saw as greater needs internationally, when the Trump administration abruptly canceled most U.S. foreign aid, and yanked away about a third of Dollar For’s budget.

And the scale of Dollar For’s direct impact in 2025 — the huge increase in medical bills they helped crush — was partly the result of a pivot, or maybe a compromise, forced by another big federal shift:

Cuts to Medicaid baked into 2025’s “Big Beautiful Bill” led Jared and Dollar For to scale back plans to focus on advocating for big policy changes and double down on direct service.

So our episode turns out to be more complicated, and richer, than I’d anticipated — and even more appropriate as we gird ourselves for challenging times.

It’s bracing to hear from Jared as he wrestles with how to keep Dollar For’s work moving forward at a time when “Shit’s wild” is truer than ever.

And because Jared and his colleagues have always had their eye on the big picture, it’s an opportunity for the rest of us to reflect on how we can maintain hope — partly by doing the “little things” that are right in front of us — things that can build our capacity, and the capacity of those around us, to push for bigger change.

I hope you’ll enjoy today’s episode, and that you’ll share what thoughts it brings up for you — you can just hit reply on this email, or tag us on Instagram, Bluesky, Facebook, or LinkedIn.

Till next time, take care of yourself!

— Dan