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.
Key Takeaways
Medicare covers roughly 70 million Americans, with about 25,000 plan permutations across the country—seniors typically choose from 100 to 200 options in their zip code with no HR department to guide them
Chapter takes a radical approach to being a Medicare brokerage that decouples plan recommendations from economics—advisors don’t know what plans pay the company, and Chapter enrolls people in plans on which it earns nothing every day
The company built the best provider directory in the country for Medicare using data integrations, ML models, and AI-powered automations—it’s the only company that can tell you the exact benefits in each plan and what a prescription will cost at a given pharmacy on a given plan.
Counterintuitively, Seniors use phones more than people in their 30s and 40s, but for communication, not transactions—this shapes Chapter’s product strategy toward phone and text-based engagement over web apps.
Voice AI has massive potential for seniors but is only effective today for narrow, well-scoped tasks like checking a specific benefit—open-ended Medicare guidance still requires human advisors.
How Chapter tested paid ads for direct to consumer but ultimately landed on a B2B2C where health systems refer patients
Why Cobi has no hiring targets and how he still finds amazing people and remains quite lean for a company with Chapter’s level of traction
How Chapter earned the right to testify before Congress without lobbyists or PR firms
Chapter’s broader vision for seniors beyond Medicare involves reverse engineering the use-money vs. earn-money life phase to find optimal solutions.
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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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You can connect with Cobi Blumenfeld-Gantz through the following platforms:
LinkedIn: https://www.linkedin.com/in/cobibgantz/
Website: https://askchapter.org/
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You can connect with Adam through the following platforms:
Substack: https://www.emergentproduct.com
Website: www.firstprinciples.la
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Website: https://www.emergentproduct.com
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For inquiries about sponsoring the podcast or becoming a guest, email adam@firstprinciples.la.
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