Chapter

Our AI-powered Medicare platform is improving how seniors choose health coverage.

[Chapter @askchapter]

Just raised our Series E, announcement below. We're just getting started.

[The Information @theinformation]

Is Anthropic altering model performance to force costly upgrades? Chapter Co-Founder and CEO @CobiBGantz outlines a shift his team recently noticed:

"Anthropic has kind of taken a page out of the Apple playbook, where they have...decreased the quality of the prior models right before they launched the new model, so that the new model feels better."

[Chapter @askchapter]

Many thanks to Don Lemon and @alexrkonrad for participating in our inaugural event at the @CherryLnTheatre and reception at Wild Cherry. Enjoyed the very candid conversation about tech and media!

[Alex Konrad @alexrkonrad]

"It's way better to have no one, than the wrong person."
- @askchapter CEO Cobi Blumenfeld-Gantz (@CobiBGantz)

Blumenfeld-Gantz is one of a number of high-growth startup founders to have spent formative years at Palantir.

His biggest lesson from the controversial tech giant: talent density can get you through anything.

"There was a period of 3 or 4 years when Palantir actually didn't grow much," he tells @UpstartsMediaCo. "That's a death knell for a company today."

Palantir engineered its way out, he argues. "Keeping the talent bar very high, and being willing to eat the pain... that's a continuously learned lesson."

Catch the full interview on The Upstarts Podcast.

[Chapter @askchapter]

@alexrkonrad @UpstartsMediaCo Watch the entire interview here: https://t.co/YW3zcgqXcV

[Chapter @askchapter]

Great questions from @alexrkonrad, thanks for having us on @UpstartsMediaCo

[K @kahnfessions]

great show @CobiBGantz and @askchapter !

[Alex Konrad @alexrkonrad]

“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 🫡

https://t.co/zj7DxLNvNS

[Suffiyan Malik @suffiyanmalikk]

“There's absolutely no incentive for an insurance carrier to invest dollars into making me healthy today.”

Cobi Blumenfeld-Gantz (@CobiBGantz) explains the structural flaw in healthcare: why carriers choose reactive care over long-term wellness when patients might switch providers in less than a year.

“I may or may not be covered by that insurance carrier in 9 months. And so why would they invest anything other than relatively reactive care?”

@askchapter @HillValleyForum

[Chapter @askchapter]

Can’t stop, won’t stop

[Suffiyan Malik @suffiyanmalikk]

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!!

[Chapter @askchapter]

Appreciate the shout out, @NYSE

[Chapter @askchapter]

We are trying to solve one of the most significant problems in healthcare today: the fact that millions of American seniors are on the wrong Medicare plan for their specific needs. They are either overpaying for coverage they could receive for far less, or they are underinsured and face serious obstacles to care when they get sick.

Appreciate the great questions from @CarolineHydeTV and @EdLudlow at @Bloomberg.

[Chapter @askchapter]

Thanks again for having us on. The additional $100M will allow us to serve more seniors in more ways.

[TBPN @tbpn]

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.

[Chapter @askchapter]

@johnpalmer We’ll cover the cost of the cookies

[Suffiyan Malik @suffiyanmalikk]

The Information (@theinformation) reported yesterday that @askchapter is now backed by two Vice Presidents. @JDVance (through @NaryaVC) and @algore after their latest $100m round valuing them at $3B. 2x their last valuation.

Having spent some time together, I can attest that @CobiBGantz is one of the sharpest operating minds out there, I would not want to compete with him in the retirement category which I believe Chapter is winning.

The episode we recorded in Q4 2025 was one of the best performing conversations on @WeThe_Builders, highly recommend checking it out. We discuss the Chapter masterplan and talk about lessons from @PalantirTech days among a wide range of topics.

Backed by @8vc, @NaryaVC, @SusaVentures, @peterthiel, Al Gore, @xyz_vc, @fubini, Addition (@leefixel), Generation Investment Management, @stripesco_

[Chapter @askchapter]

@MollySOShea Going forward we'll be referring to this round as "A Convenient Investment"

[Chapter @askchapter]

❤️

[Molly O’Shea @MollySOShea]

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

[Chapter @askchapter]

@nypost Clankers beware, Philly is Raqqa for your kind

[Chad Byers @chadbyers]

Susa co @askchapter raised $100m at ~$3B.

We have ~15% of Susa III dollars invested in Chapter. 3x-5x more than a typical fund would have in a single company.

It's very easy for investors to claim they have high conviction in a company, but the truth is always in the data. How concentrated are they in that single name?

We led the seed and have invested in every round. When you work with founders like Cobi and the team he's built around him, you go all in.

h/t @SethGB

https://t.co/k497tW0viC

[The Information @theinformation]

An AI-driven startup with 90% gross margins is scaling fast while keeping staffing lean, challenging how traditional Medicare brokers operate.

Read more in today's AI Agenda newsletter: https://t.co/1m18DlH7Va

[Chapter @askchapter]

https://t.co/SfO0flUZt1

[Chapter @askchapter]

Just raised our Series E, announcement below. We're just getting started.