Oscar Health

Oscar is a public company, so major strategic and capital-allocation decisions rest with the CEO and the board. Mark Bertolini, named CEO in 2023, sets the operational direction with his deep legacy-carrier experience from his tenure as chairman and CEO of Aetna. Co-founder Mario Schlosser, as CTO, oversees the technology and analytics infrastructure that the company considers its core competitive asset. The company does not run a traditional family-office portfolio; it invests its surplus cash into fixed-income securities as disclosed in public filings.

Legally and operationally, Oscar is an insurance company. It holds insurance licenses, bears full underwriting risk on its policies, and earns revenue primarily from premiums. Its technology platform — used to adjudicate claims, manage member experiences, and guide care routing — is the internal operating model, not a separately sold software product. The distinction matters because its financial performance follows insurance economics: it must manage medical-loss ratios, administrative costs, and risk-adjusted capital requirements.

Josh Kushner co-founded both Oscar and Thrive Capital. Thrive was an early and repeat investor in Oscar through its venture funds, though after Oscar’s 2021 IPO, Thrive’s influence shifted to that of a significant public-market shareholder rather than a private-backer. Kushner remains active on Oscar’s board, and the relationship represents a long-term personal and institutional commitment, but the firms are governed separately.

Since early 2023 Oscar has pivoted explicitly toward profitability and away from membership growth for its own sake. The company exited several state markets where it could not achieve sufficient scale, consolidated around its strongest geographies, and focused relentlessly on its medical-loss ratio. Bertolini’s appointment as CEO accelerated this posture. The pivot paid off when Oscar reported its first full-year GAAP profit for 2023, signaling that the board’s patience with the growth narrative had a clear limit.

No. Oscar does not operate as a family office, an investment adviser, or an asset manager. Its corporate treasury function invests surplus cash conservatively, as disclosed in quarterly and annual SEC filings. The firm does not run a venture arm or maintain a portfolio of external private companies beyond any passive instruments it holds. Allocators looking for a diversified investment platform will not find one here.

Oscar operates in three principal coverage segments: individual and family plans sold through the Affordable Care Act exchanges, small-group health plans, and a smaller Medicare Advantage book. The ACA individual market now dominates its revenue, with Florida, Texas, and New York serving as its core states. The company has exited the large-employer segment and the Cigna + Oscar co-branded small-group venture.

In 2016, a subsidiary of Berkshire Hathaway entered a reinsurance agreement to share claims risk with Oscar in exchange for premium. That deal helped Oscar stabilize its balance sheet during high-growth years when its medical-loss ratios were volatile. More recent filings describe quota-share arrangements with other reinsurers, indicating the Berkshire structure has largely run off or been replaced. For an allocator, the broader point is that reinsurance has been a recurring capital-management tool rather than a permanent structural advantage.