Oscar Health (2013–2021)
Oscar launched as a tech-first individual health insurer, raising over a billion dollars before its 2021 IPO. It spent heavily on marketing and customer experience but posted persistent underwriting losses.
Shares sagged after the IPO as losses continued.
It showed that consumer-friendly technology alone doesn't control medical costs.
Angle's AI navigation is the same bet on technology lowering claims — Oscar proved it's hard.
