Oscar Health – A Mosaic That’s Starting to Come Together

Lately, I’ve been spending more time looking into a company that I find increasingly compelling: Oscar Health. I don’t own any shares yet, but if my thesis continues to develop in a positive direction, Oscar could very well become my second core position, alongside Hims & Hers.

So why Oscar?

What draws me in is the company’s clarity of focus. Oscar isn’t trying to be everything to everyone — and I like that. Instead, they’re tackling one of the most broken systems in the U.S. economy: health insurance. Their approach is tech-first, member-centric, and data-driven — three qualities that, in my view, give them a real chance at building long-term structural advantage.

One data point that stood out to me is their high Net Promoter Scores, which suggest that people genuinely like being Oscar customers. In a space typically defined by frustration and bureaucracy, that kind of customer sentiment matters — a lot. It’s not just a brand story; it’s a signal of product-market fit in a notoriously difficult vertical.

Still in research mode

I’m still in the process of doing deep research — trying to better understand the unit economics, the regulatory landscape, the competitive environment, and how sustainable their current growth really is. But based on what I’ve seen so far, Oscar Health looks like one of the most interesting long-term bets in the healthcare space.

The risks

This is still a young company. Profitability is in sight, but it hasn’t been achieved yet, and the insurance industry is notoriously difficult to navigate — with political risk, margin compression, and capital intensity always looming. Execution will matter more than vision. But I’m open to risk — as long as the reward potential justifies it.

Right now, I’m not rushing into a position. I want to understand the company on a deeper level before committing real capital. But I could absolutely see a scenario where Oscar becomes my second concentrated position, next to Hims. There’s something here — and I plan to keep digging.