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The Philosophy of U.S. Healthcare (And Why It Resists Change) | with Tom Stein

"This is why insurance is such a beautiful problem... there is no solution. There are only psychological or philosophical answers to it."

What if the rising cost of health insurance is a deeply ingrained philosophical problem?

My guest this week is Tom Stein, CEO of American Trust Administrators (ATA). But this episode isn’t just a tactical breakdown of stop-loss and aggregate underwriting; it is a masterclass in the history, psychology, and economics of the U.S. healthcare system.

Tom and…

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The Philosophy of U.S. Healthcare (And Why It Resists Change) | with Tom Stein
257
July 14, 2026

The Philosophy of U.S. Healthcare (And Why It Resists Change) | with Tom Stein

"This is why insurance is such a beautiful problem... there is no solution. There are only psychological or philosophical answers to it."What if the rising cost of health insurance is a deeply ingrained philosophical problem?My guest this week is Tom Stein, CEO of American Trust Administrators (ATA). But this episode isn’t just a tactical breakdown of stop-loss and aggregate underwriting; it is a masterclass in the history, psychology, and economics of the U.S. healthcare system.Tom and I
$6.5B DOJ Crackdown, Medicare GLP-1 Shifts, Hospital Price Tags | with Sid Sinha
July 10, 2026

$6.5B DOJ Crackdown, Medicare GLP-1 Shifts, Hospital Price Tags | with Sid Sinha

"When you see $6.5 billion in healthcare fraud, we all end up absorbing that in the commercial market."In this episode of Last Month in Healthcare, Producer Nathaniel and I sat down with Sid Sinha, founder and CEO of Avant/Nara Health, to break down the biggest healthcare news stories of June 2026.We started by looking at the DOJ's massive $6.5 billion healthcare fraud crackdown and what 1,400 revoked provider privileges actually means for the commercial market.We also tackled the stark re
How One App Could Save U.S. Healthcare | with Matt Taylor
256
July 7, 2026

How One App Could Save U.S. Healthcare | with Matt Taylor

"Fee-for-service has led to transactional primary care where providers have 10 or 15 minutes to code as much as they can just to keep the doors open. We’ve moved away from the idea of primary care as the quarterback of the entire health ecosystem."My guest this week is Matt Taylor, VP of Sales at Castlight. Having spent his career navigating the complex landscape of health plans, telehealth, and enterprise analytics, Matt has a unique vantage point on why our current approach to "sick care" is
The 2026 Employer Health Plan Playbook | with Mark Cuban
255
June 30, 2026

The 2026 Employer Health Plan Playbook | with Mark Cuban

"The most unused cash in the country right now is the money you're wasting on healthcare... If you save a million dollars a year, that's $20 million in market cap."Is your company treating its healthcare spend like a business strategy, or are you just writing a blank check to the major insurance carriers every year?In this episode, I was (finally) joined by Mark Cuban, Ann Lewandowski, and Matt Miron.After answering how he would approach healthcare for a hypothetical company on Shark Tank,
Managing the Exploding Costs of Specialty Drugs | with Jake Velie
254
June 23, 2026

Managing the Exploding Costs of Specialty Drugs | with Jake Velie

"There's no reason why I should be able to do an infusion for 50% of the cost of what it's currently being allowed at. We've seen allowed amounts between $57,000 and $80,000 for Keytruda. I typically can have that in the home at $29,000."My guest this week is Jake Velie, CEO and co-founder of National Integrative Health (NIH). After spending the first half of his career in the clinical "meat grinder" of value-based care on the provider side, Jake realized the only way to truly fix the system w
You’re Probably Wrong About Reference-Based Pricing | with Jeff Bak
253
June 16, 2026

You’re Probably Wrong About Reference-Based Pricing | with Jeff Bak

"We did this survey with a third-party consulting group who talked to 2,000 brokers. Their perception was that 25% of bills are going to be balance bills; it's actually 3%."Is Reference-Based Pricing (RBP) still something that just creates endless problems for HR?My guest this week is Jeff Bak, CEO of Imagine360. Jeff brings 30 years of healthcare and private equity experience to the table, and he's leading the charge to rebrand and evolve RBP from a defensive "pay and defend" model into a c