[3][5] Mother Jones reported in March 2020 that Joshua and his brother Jared owned the firm's parent company, Thrive Partners III, at the time of its incorporation in 2013.

[8] The firm expanded its operations to Tempe, Arizona, in August that year, where it decided to locate its Concierge teams, their name for their member services model.

[9] On August 23, Oscar announced it would be exiting the New Jersey Marketplace at the end of 2016, citing uncertainties in the market that would make it challenging "to operate effectively and continue to deliver access to quality healthcare.

"[10] Oscar also announced that it would halve the size of its provider network in New York amidst rising premiums in order to "gain more control over pricing and patient experience".

[14] On June 15, 2017, Oscar announced its partnership with Cleveland Clinic to offer individual health insurance plans to consumers in five counties in Northeastern Ohio.

[15] On June 21, 2017, Oscar announced its intention to expand to additional markets in 2018 in areas of Tennessee, Ohio, Texas, New Jersey and California.

[16] On July 12, 2017, Oscar announced that it would be selling small group insurance in the Nashville metro area to companies with up to 50 employees through a strategic partnership with Humana.

Despite Jared severing ties with Thrive Partners when he began working for the Trump administration, these coordinated visits raised questions about his ability to be impartial on Saudi affairs.

While Kushner does not hold a formal role in Oscar's daily operations, he remains a major shareholder and Schlosser confirmed (as of 2017) that he has "significant input in multiple aspects of the company like strategy, hiring, and marketing.

In 2015, AdWeek reported that Oscar was airing its first television campaign targeted at the demographics of "new parents who are too frazzled to shop for health insurance.

[29][30] During the 2016 Series C round, Oscar raised $400 million led by Fidelity Investments, with secondary participation from previous investors, with a reported valuation of $2.7 billion.

[2] Vox reported that in 2015, Oscar Health lost $92.4 million in New York as the firm's analytical models failed to accurately forecast "the people who signed up for coverage were sicker than the company had expected.

[38] In May 2017, Bloomberg reported that Oscar's first quarter loss had narrowed by nearly half, writing that the company was "beginning to get a handle on its medical costs.