Building Revolutionary Technology for Seniors
In this episode, we sit down with Cobi Blumenfeld-Gantz, founder and CEO of Chapter, a technology company transforming how seniors navigate Medicare and retirement through data-driven plan selection and AI-enabled advisory services. A former member of Palantir’s U.S. government team, Cobi started Chapter after watching his own parents receive poor guidance from a local Medicare broker.
We dive into how Chapter has built the best provider directory and prescription pricing engine in the country to match seniors with the right plan across 25,000+ Medicare permutations—without the conflicts of interest that plague the rest of the industry. Cobi shares why he chose to keep the team lean, how Chapter’s B2B2C model unlocked enterprise health system partnerships, what it took to testify before Congress and catalyze regulatory reform, and how he thinks about building a full retirement platform beyond Medicare.
If you’ve ever wondered how Medicare actually works, why the brokerage industry is under DOJ investigation, or what it takes to build a product-plus-service company with real defensibility, this episode is for you.
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In this episode, we cover:
Introduction (00:00:42)
What Medicare actually is and the different plan types (00:03:52)
What happens when you turn 65 and have to figure out Medicare (00:05:19)
What Chapter builds: the data engine behind plan matching (00:07:37)
The perverse incentive structure of Medicare brokerages (00:11:33)
Chapter’s unbiased model and why they enroll people in plans they earn nothing for (00:14:22)
Why there are 25,000 Medicare plan permutations across the country (00:15:46)
Building tech for seniors: misconceptions and design principles (00:17:28)
Voice AI for seniors: where it works and where it doesn’t (00:21:46)
From Palantir to consumer: learning the B2B2C model (00:24:01)
How Chapter’s enterprise partnerships actually work (00:26:50)
Keeping the team lean: hiring philosophy and ruthless prioritization (00:30:16)
Testifying before Congress without lobbyists or PR firms (00:36:02)
The service-plus-product hybrid: advisors as an asset, not a seasonal hiring problem (00:41:40)
Beyond Medicare: building the retirement platform of the future (00:47:53)
What was obvious at the start and what the company got wrong initially (00:51:41)
Where to find Cobi and Chapter (00:55:26)
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