Chapter

“I am one of the most hated people in the industry." Chapter CEO Cobi Blumenfeld-Gantz (@CobiBGantz) is on a mission to save seniors thousands on their Medicare. That makes him a target for legacy Medicare providers, he says. "I'm bad for business." That business is booming, with @askchapter recently reaching $100M in ARR and a $3B valuation 📈 It's a bipartisan mission, too. @VivekGRamaswamy is a co-founder, and Chapter is one of the only startups to count VPs on both sides of the aisle as investors in @JDVance and @algore 🤝 On The Upstarts Podcast, Blumenfeld-Gantz shares: ▪️lessons from working as a forward deployed engineer at Palantir (and its controversies) ▪️how going national from day one was a worthwhile gamble ▪️ why his most important metric is a twist on a classic startup one: product-market-channel fit Plus, his Upstart Moment: when last year’s government shutdown cut off Chapter’s data during Medicare’s busiest enrollment window, and his team had one week to reverse-engineer their way out. Thanks to our partner @mercury for supporting Upstart stories like this 🫡 youtu.be/Ff64VfasdzU

Special edition of We The Builders at @HillValleyForum with Cobi Blumenfeld-Gantz (@CobiBGantz) who cofounded @askchapter with @VivekGRamaswamy. Since then they have announced $100m in a new Series E funding round valuing the company at $3B. They have 2x-ed since in valuation our last conversation in November. I would make the case that if you were a listener or subscriber of We The Builders, you would have and should have known of Cobi & Chapter. Maybe you could have tried to get into that round of what is going to be the category winner in the future of retirement. The company is backed by @NaryaVC, @SusaVentures, @xyz_vc, Addition, Generation Investment Management, Peter Thiel, Lee Fixel, @8vc, @stripesco_ and more. Congrats to friends of the show @ColinGreenspon, @falondonohue, @SethGB, @SebastianCaliri!!

Special edition of We The Builders at @HillValleyForum with Cobi Blumenfeld-Gantz (@CobiBGantz) who cofounded @askchapter with @VivekGRamaswamy. Since then they have announced $100m in a new Series E funding round valuing the company at $3B. They have 2x-ed since in valuation our last conversation in November. I would make the case that if you were a listener or subscriber of We The Builders, you would have and should have known of Cobi & Chapter. Maybe you could have tried to get into that round of what is going to be the category winner in the future of retirement. The company is backed by @NaryaVC, @SusaVentures, @xyz_vc, Addition, Generation Investment Management, Peter Thiel, Lee Fixel, @8vc, @stripesco_ and more. Congrats to friends of the show @ColinGreenspon, @falondonohue, @SethGB, @SebastianCaliri!!

Happy Thursday. On today's show: - @cz_binance (Binance) - @esaagar (Breaking Points) - @TheStalwart (Odd Lots) - @AndrewDai (Elorian) - @kesava_kirupa (Luminai) - @CobiBGantz (Chapter) - @talhof8 (Enclave) - Brian Manning (Xona Space) See you on the stream.

Around 11,000 Americans are retiring every single day for the next 10 years. 60m people in the US are retired. Medicare is one of the biggest problems among this community, there are 100s of providers and choosing the wrong one could either mean losing thousands of dollars or your life (I think Cobi quoted a report citing ~20% fatality on choosing the wrong provider). If your parents are not in that age group yet, you probably haven’t started thinking about this but it is one of the biggest and most underserved markets in the US. The opportunity is not to just help senior citizens with Medicare, the opportunity is to redefine what retirement means for people over the age of 65. My maternal grandfather retired at the age of 82 and was one of the healthiest and fittest people up until then. Your health cannot be wholly defined by your diet and exercise routine, purpose in life plays an equal if not one might argue a bigger role. In my day job I work with Tim Draper, his dad Bill Draper who I met a couple of years ago was going to office twice a week at 95 years of age. Charlie Munger did the Berkshire Annual Shareholder meeting with Warren Buffett at 99. If you can figure out a way to give purpose to people over 65 and activate them that is ~23% of the US population by 2050. What impact could that have on the GDP? I will leave that for you to imagine. You probably have an uncle, grandparents or parents where you can see the difference between the ones who hang up their boots and the ones who never retire. There is something about the keeping your brain active which is more meaningful in many ways then even your diet or gym routine. In our last episode we had Colin Greenspon on the show who started Narya Capital. Narya is an early investor in Chapter, cofounded by Cobi Blumenfeld-Gantz and Vivek Ramaswamy. JD Vance and Peter Thiel were on the board of the company and maybe that is why the company is widely misunderstood or MAGA labelled, hear from the CEO Cobi on the masterplan of Chapter. My conversation with Cobi is his first long form podcast and it is one of the best ones I have recorded so far. He was incredibly candid and insightful as we got to dive into his time at Palantir where he spent 5 years, why he chose to go after the ~60m seniors (aged above 65) in the US to make Medicare easier for them, utility of AI in its current state, recruiting talent and some common myths in business. @CobiBGantz @askchapter @VivekGRamaswamy @NaryaVC @ColinGreenspon

ICYMI: Chapter (@askchapter) Raised $100M Series E at a $3B Valuation Led By Al Gore’s Generation Investment Management - 2X valuation <1 year - Total funding ~$285M - 3x revenue growth in 2025, surpassing $100M in ARR - "Past 4 rounds have been preempted" Founded by @CobiBGantz, Chapter is building the leading AI retirement platform. New investors: Fifth Down Capital & @8vc Existing investors: Stripes, XYZ VC (@fubini), Addition, Narya Capital (@JDVance), @SusaVentures, & Maverick Ventures. PS - Cobi also shares key lessons from Palantir about talent density.. including @ssankar's “hamburger rule.” 00:00 Big Funding Announcement 00:18 How Al Gore Joined 01:01 Bipartisan Backing 01:19 JD Vance Investor Era 01:48 Total Raised & Valuation 02:00 Vision for Retirees 02:53 What Makes Chapter Different 04:16 Hot Take: Healthcare > Defense 04:59 LA Medicare Fraud Explained 06:13 Cutting Waste in Medicare 07:05 Palantir Talent Lessons 08:10 Hamburger Rule Wisdom 09:19 Looking Ahead This Year