Josh Kushner stands to make a mint on Oscar Health’s much-awaited IPO, and has almost total control. Here are the venture investors who will also do well.

karlie kloss

Summary List Placement

Mario Schlosser and Josh Kushner created Oscar Health eight years ago as a tech-savvy health insurance company selling plans on the Affordable Care Act marketplace.

Now the company serves 529,000 customers across 18 states, mostly in the individual market, it says, where people often receive federal aid to buy insurance and shop for plans based on their price.

Oscar hopes its technology platform will drive a better customer experience which will cause users to flock to its offerings.

That unlocked potential is the backdrop behind Oscar’s debut on the public markets, expected to take place on Wednesday. It is expected to price shares between $36 to $38 apiece.

After its IPO, its venture capital investors — which include Google’s investment arm Alphabet Holdings, Peter Thiel’s Founder’s Fund, and Josh Kushner’s own Thrive Capital — will be sitting on some substantial nest eggs.

The company’s filing didn’t name all of the investors who have taken part in Oscar’s $1.6 billion in overall fundraising through the years but it did reveal its biggest shareholders.

While we don’t know how much profit each investor will make, we can calculate the total value of each major shareholder’s stake by pricing all of their shares at the midpoint of the expected range, $37 a share.

As is typical these days, Oscar Health is using a two-tier structure where it sells Class A shares to the public, with each of those shares offering one vote per share; and it has Class B shares — which are owned only by its founders, executives and key investors — that come with 20 votes per share. Venture capitalist Kushner, via his Thrive Capital firm, will have more than 75% of the company’s voting power.

Here’s who can cash out huge paydays once Oscar Health is public.

SEE ALSO: One giant question is swirling around the IPO of hot health insurer Oscar: Can the startup ever make money?

Thrive Capital (Joshua Kushner): $1.21 billion

A cofounder of Oscar Health, Kushner is now the company’s vice chairman.

In a sign of even more VC investments to come, Kushner’s firm, Thrive Capital, recently raised $2 billion for two early- and late-stage funds.

Kushner is the brother of Jared Kushner, the son-in-law of former President Donald Trump.

Thrive’s stake is:

  • 32.8 million Class B shares. (After the IPO, Thrive’s shares will represent a 76% voting power in the company.)

At $37 a share, those shares are worth $1.21 billion.

CEO Mario Schlosser: $267.5 million.

Before cofounding Oscar Health in 2012, Schlosser cofounded Latin American social gaming company Vostu, leading its analytics and game design practices. He also spent three years as a senior investment associate at Bridgewater Associates, where he developed analytical trading models. 

His stake is:

  • 146,514 Class A shares and 7.085 million Class B shares. (After the IPO, Schlosser will control 14.3% of Oscar’s voting power.) Schlosser is selling 366,000 Class A shares as part of the public offering.

At $37 a share, those combined shares are worth $267.5 million.

Alphabet Holdings: $889.5 million

Google parent Alphabet’s venture arm is one of several investors that bought shares in more than one of Oscar Health’s venture funding rounds. Most recently, Alphabet joined a $225 million round in June, 2020.

Its stake is:

  • 24.04 million Class A shares

At $37 a share, those shares are worth $889.5 million.

Founders Fund: $799.2 million

Many of the biggest tech names to recently go public have had a financial boost from Founders Fund, including Airbnb, Lyft, and Spotify.

Founders Fund led a $165 million funding round in 2018, and took part in a $140 million round last December.

Its stake is: 

  • 21.6 million Class A shares.

At $37 a share, those shares are worth $799.2 million.

General Catalyst: $535 million

General Catalyst is another firm that has stepped up more than once to take part in an Oscar Health funding round, most recently in a June 2020 round that netted the company $225 million.

Its stake is:

  • 14.46 million Class A shares

At $37 a share, those shares are worth $535 million.

Khosla Ventures: $432.9 million

Khosla has taken part in multiple funding rounds for Oscar Health as well, most recently joining the company’s $140 million raise last December.

Its stake is:

  • 11.7 million Class A shares.

At $37 a share, those shares are worth $432.9 million.

Formation8: $272.3 million

Oscar Health remains one of several legacy investments made by high-flying but short-lived VC firm Formation 8, which disbanded in 2015 with the three founding partners going their separate ways.

The firm’s investments also include Oculus, acquired by Facebook for $2 billion, and RelateIQ, the startup bought by Salesforce for $390 million.

Its Oscar Health stake is:

  • 7.36 million Class A shares.

At $37 a share, those shares are worth $272.3 million.

FMR LLC (Fidelity): $252 million

Fidelity made a big splash in February, 2016, by leading a $400 million investment that valued Oscar at $2.7 billion — that was $1 billion above its valuation when it raised funds just five months earlier, according to Bloomberg.

Its stake is:

  • 6.81 million Class A shares.

At $37 a share, those shares are worth $252 million.

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