Oscar Health: The Infrastructure Layer Set to Disrupt a Broken System

There are moments in investing where you come across a company that feels inevitable. Not because it is big and safe and dull, but because it sits at the center of a system that is completely broken, where the incumbents are bloated, outdated, and profit from inefficiencies. A company that offers a credible solution to real pain. Oscar Health is that company. In this report, I will show you why.

I only own two stocks. Hims and Hers and Oscar Health. This is not diversification. This is conviction. My goal is not to match the market. My goal is to find asymmetric opportunities, stocks that can 5x or 10x over time, with a foundation of logic, need, and market dysfunction on their side.

Oscar Health is the infrastructure layer for one of the most dysfunctional industries in America. Healthcare is a 4.5 trillion dollar behemoth, and it is failing. We pay more than any other developed country and life expectancy is falling. You do not need a PhD in policy to know that something is deeply wrong.

Let us break this down.

The American Healthcare Crisis

Let us call the system what it is. A cash grab, disguised as care. In the US, you do not just have doctors and patients. You have layers. Brokers. Pharmacy Benefit Managers. Hospital systems. Billing software. Insurance giants. Claims processors. Regulatory consultants. Tech vendors. All fighting for a cut of your monthly premium and each medical transaction.

Every step you take in the healthcare journey, someone is making money, often without adding value. A typical American may need to navigate dozens of opaque entities just to get one prescription. The incentives are misaligned. Patients want care. Middlemen want margin.

The result is that we have the highest per-capita healthcare spend in the world and some of the worst outcomes among developed nations. Chronic diseases are rising. Mental health is worsening. Administrative costs eat up over 30 percent of total healthcare spending. And health insurance is still a mystery for most people.

This is not just unsustainable. It is immoral.

Oscar Health’s Core Bet: Rebuild from the Inside Out

Oscar Health is not just trying to put a new face on insurance. It is rebuilding the back end. While Hims and Hers focuses on the front, customer experience, brand trust, direct to consumer medicine, Oscar is the operating system. The pipes, the rails, the logic layer.

Oscar has built a fully integrated, tech driven insurance stack that includes claims processing, risk scoring, provider networks, member engagement tools, and more, all driven by software and increasingly by AI.

This is not a white labeled third party system. This is Oscar’s core competency. Their infrastructure is already used not only to support their own insurance plans but also as a platform for others. That is important. It creates leverage. Scale. And a long term path to becoming the AWS of health insurance.

Oscar does not sell buzzwords. It sells clean infrastructure in a messy industry.

The ACA Opportunity: A Land Grab in Plain Sight

The Affordable Care Act marketplace was designed to provide access to affordable insurance for Americans who do not receive coverage through their employer. While often thought of as a tool for low income households, that is no longer the full picture.

Thanks to legislative updates, including subsidies expanded under the American Rescue Plan and extended through the Inflation Reduction Act, ACA plans now cover a much broader demographic. Millions of middle income Americans qualify for subsidized premiums. The middle class is now in play.

And here is the kicker. Many legacy insurers are exiting the ACA marketplace. Why? Because it is complex. It requires member engagement, precise risk scoring, and proactive care, things the old system does not do well. It also requires low admin costs, tech flexibility, and the ability to navigate changing policy. In short, it requires what Oscar has built.

As of today, Oscar is live in 20 states. And it is growing. With competitors pulling back, Oscar is in pole position to dominate this space over the next decade. This is a secular tailwind with structural winners. Oscar is one of them.

What the Market Still Does Not See

Oscar’s stock price is still below its IPO. To some, that is a red flag. To me, it is a setup.

The same team that brought Oscar public is still here. Josh Kushner, backed by Thrive Capital, remains intimately involved. Thrive is one of the most respected investment firms in the world, with early investments in Instagram, Stripe, Robinhood, Nubank, and OpenAI.

These are not spray and pray investors. These are top tier, long horizon thinkers. Thrive Capital and its LPs do not back flukes. They back systems, infrastructure, platforms. And Oscar fits that mold perfectly.

There is no world in which Thrive and Josh Kushner are content with Oscar sitting at a fraction of its original value. They will move mountains to make this work. And they are not alone.

To continue reading and access the full report, including Oscar’s AI strategy, its connection to OpenAI, and why I believe this is one of the most asymmetric opportunities in healthcare today, become a paying subscriber. This is where the real thesis begins.