Chapter, a fast-growing startup focused on helping seniors navigate Medicare, has raised a new funding round that reportedly values the company at $1.5 billion. What makes this funding round particularly noteworthy is the network of high-profile conservative figures—including J.D. Vance, Blake Masters, and Vivek Ramaswamy—linked to its financial and strategic backing.
A Politically Connected Healthtech
According to TechCrunch, the startup’s latest round includes capital from Founders Fund (where Masters is a partner), Thiel Capital, and investors close to Strive Asset Management, which was co-founded by Ramaswamy. While none of the politicians or their associates sit on Chapter’s board, the presence of these names reflects a broader trend of conservative-aligned capital flowing into healthcare tech and aging-focused ventures.
What Chapter Does
Chapter operates a platform designed to optimize Medicare plan selection for seniors by offering software-assisted advisors and personalized comparisons. Unlike traditional Medicare brokers who are often incentivized to push specific plans, Chapter claims to operate with full-plan access across providers, aiming to serve the individual’s best interests.
The company says its platform improves customer satisfaction and reduces overspending on unnecessary coverage. This positioning has helped it attract funding even amid a cautious VC environment.
A Market Worth Billions
The Medicare market is worth over $800 billion, and as more Americans reach retirement age—especially during the “Peak 65” demographic wave—companies like Chapter are poised for significant growth. The startup plans to use the funding to scale operations, expand its tech stack, and grow its licensed advisor network.
With over 60 million Americans currently enrolled in Medicare, the need for clear, unbiased plan guidance has never been more urgent.
Political Echoes in Healthcare
While Chapter presents itself as nonpartisan, its ties to conservative power players come as Republicans increasingly push for privatized innovation in federal healthcare programs. This adds a political undertone to its growth strategy—especially as 2025 policymaking battles around Medicare intensify.
Still, the startup’s leadership has emphasized that its mission is “to serve seniors first,” regardless of political leanings.
