Capitalist Letters

Capitalist Letters

Oscar Health Revisited: A 10-Bagger In Making Or Doomed To Fail?

An asymmetric opportunity with substantial risks.

Oguz Erkan's avatar
Oguz Erkan
Nov 26, 2025
∙ Paid

Up and down, up and down, up and down… My nine months of holding Oscar can be summarized by these two words.

It would go from a “generational opportunity” to a “shitco” overnight, and repeat this every month.

It’s been a total rollercoaster:

I am not going to lie, it’s psychologically a hard stock to hold. Last time I felt this way, it was for Hims & Her…

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