Why Every Broker Needs A Fiduciary Co-Pilot | with Charlie Gragg

"I relate it to one of the Wizard of Oz characters... I've seen behind the curtain. I know how it's all put together." What happens when a man who spent nearly five decades inside every corner of the self-funded industry decides his final act is to give the playbook away?My guest this week is Charlie Gragg, a true first-generation veteran of self-funding. Charlie started in the late 1970s underwriting stop-loss cases on napkins from payphone booths, went on to run his own TPA, and has now semi-

"Employers have the right to expect much more from their benefit consultants than ever before. This isn't just about managing the fully insured renewal anymore." In this week’s special bonus episode, I’m joined by Dr. Dena Bravata, physician, healthcare entrepreneur, and Clinical Advisor for ParetoHealth, to break down the findings from Pareto’s inaugural 2026 State of Healthcare Spend Report. Based on responses from nearly 1,600 CEOs, finance, and HR leaders, Dena and I unpacked why employers

"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

"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

"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 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,