April19 , 2025

    Chapter, a Medicare startup with links to Vance, Thiel and Ramaswamy, just raised a round at $1.5B valuation | TechCrunch

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    Chapter, a Medicare advisory startup co-founded by former Republican presidential hopeful Vivek Ramaswamy, has closed a $75 million funding round at a valuation of $1.5 billion led by private equity and venture firm Stripes.

    The startup helps seniors choose Medicare health plans analyzing doctors, hospitals, and prescription drug coverage. Unlike many other Medicare insurance brokers, Chapter claims to prioritize client needs over insurer profits.

    Naraya, the VC firm founded by Vice President JD Vance, led Chapter’s Series A round in 2020. Peter Thiel, who also invested in the company, assumed Vance’s board seat when Vance resigned to run for Senate in 2021.

    While Thiel has since resigned from the Chapter’s board, Democrat Donna Shalala, who served as a Secretary of Health and Human Services during the Clinton administration and later as U.S. Congresswoman, has filled the vacancy. Shalala told Bloomberg that Ramaswamy’s role and investments from Republicans Vance and Thiel were not an issue. “I don’t think of the company as political.”



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