Oscar Health: Unstuck (Ticker: OSCR)

The stock is up 104% since the end of March. What now?

Well, that was quite the week to take a vacation. It seemed like every stock in the Emerging Moats portfolio went up or down 20% while I was gone. Expect the same when I take another vacation six months from now. The market is getting increasingly manic, with any hint of being an AI “loser” crushing share prices, trying to distract you from focusing on what matters (fundamentals). The stock price will take care of itself. Volatility is the price of doing business when you run a concentrated portfolio that is uncorrelated with the indices…which is the point of buying individual stocks.

The largest winner for Emerging Moats has been Oscar Health. Up 104% since the end of March, the health insurance disruptor posted its earnings on May 6th, keeping its stock moving up and to the right in a trance-like line. Whatever Wall Street and the short-term pod shops were looking for, Oscar Health delivered.

Here is what I wrote on Oscar back in late 2025:

“My thesis is simple: 2025 is a temporary blip for Oscar Health’s MLR. Over the next decade, it has a clear path to MLR stability, improved operating leverage, and market share gains, which should provide the stock with upside in 2026 and the potential for ten-bagger returns over the next decade.”

The company is beginning to show us that it is executing on this thesis (scale, operating leverage) at a much faster pace than I assumed. Fears about the destruction of the health insurance market have proven overblown, providing management the opportunity to shift from defense to offense. The growth runway in the individual payor market is massive. Oscar Health remains the clear candidate to steal share.

A classic Peter Lynch stock.

In this update, I will cover:

• Why the stock finally got unstuck

• Remaining growth tailwinds

• Is there still an emerging moat?

• My investment decision

• Portfolio Update + addendum on Gambling.com Group

Why the stock finally got unstuck