Why I Finally Bought Oscar Health (OSCR)
My second position. My second conviction. And I plan to hold it forever.
Yesterday, I made a move I’ve been preparing for a long time.
I bought shares of Oscar Health at $11.20.
If you’ve been following me for a while, you know this isn’t a snap decision. I wrote about Oscar some time ago — I laid out why I find the business compelling, why I think the U.S. healthcare system is one of the most broken but also one of the most investable categories in the world, and why Oscar stood out to me as a digital-first disruptor. I said I was watching closely. And yesterday, I finally pulled the trigger.
Oscar Health is now my second portfolio position.
The only other stock I hold is Hims & Hers.
Two companies. Two core human needs: health and insurance.
And I believe both have 10x potential.
Why now?
Simple: the risk-reward setup has never looked better.
Oscar Health has spent the last few years in the trenches. Tech hype inflated expectations early on, and then the harsh realities of regulated insurance markets brought the company down to earth. But now we’re at a turning point.
The new CEO, Mark Bertolini, is not a tech-bro figurehead — he’s the real deal. Former CEO of Aetna. Deep operational experience. And he’s come in with a real gameplan, one that’s focused, structured, and pragmatic. Everything I’ve seen from him so far gives me the impression that he knows exactly what he’s doing. This is not a visionary guessing his way forward. This is an operator.
Oscar’s leadership, now with Mark and still deeply connected to the founding DNA, is laser-focused on execution. That’s what I want to see at this stage.
The Founders: Skin in the Game
Let’s talk about Joshua Kushner and Mario Schlosser.
These two didn’t just start a company — they committed to building something enduring. Kushner, in particular, has gone beyond the usual symbolic insider buy. He’s invested privately, and through his firm Thrive Capital, which continues to hold a major stake.
And Thrive Capital is no ordinary VC. They were early in Instagram, early in OpenAI, early in Robinhood, early in Hims & Hers. This is a firm that bets selectively, not like traditional VCs who spray and pray across dozens of startups. Thrive picks a few names and dives deep. They back founders, they understand markets, and they stay in the game.
That matters to me. A lot.
Bending the Cost Curve
The U.S. healthcare system is a mess. Everyone knows it. Everyone hates it. But very few companies are genuinely positioned to fix any part of it.
Oscar is one of them.
They’ve built a tech-first, member-first experience that actually works. Their Net Promoter Score is well above the industry average — and this is health insurance we’re talking about. That alone is a red flag for incumbents.
Add to that their lead in AI-driven claims handling, digital onboarding, and member engagement, and it becomes obvious: they are years ahead of legacy players.
The health insurance industry is dusty, heavily regulated, and painfully slow to change.
Which makes it ripe for disruption.
And Oscar is positioned — finally — to capitalize on that.
What About Michael Burry?
Yes, Michael Burry has taken a position in Oscar Health.
Do I care? A little.
But let’s be clear: Burry is a trader, not an investor. He might be out tomorrow.
Still, it’s worth noting that even deep value players are spotting the asymmetry in Oscar’s setup right now. That says something.
Final Thoughts: I’m In. Long Term.
Oscar Health now sits beside Hims & Hers in my ultra-concentrated portfolio.
And I plan to hold it for years — ideally, forever.
This is my approach:
Find wonderful businesses.
Buy them when the asymmetry is on your side.
And then hold, and let compounding do the heavy lifting.
I believe Oscar Health is about to complete its turnaround. The market is not yet pricing in the upside.
This is the window. And I took it.
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