From HIMS to Oscar: Why I’m Making Oscar Health My Largest Position

There are moments in investing when clarity cuts through the noise. For me, it started with HIMS. A bold, consumer-first business tackling stigma, expanding access, and building a strong brand in a broken healthcare landscape. I entered when the stock was depressed, when sentiment was exhausted, and when the narrative around DTC medicine was still met with skepticism. That was the beginning of my ultra-concentrated journey.

But something changed as I kept going deeper into this space. The more I studied the healthcare system from within, the more I learned about Oscar Health. And the more I compared HIMS and Oscar, the clearer it became. HIMS is a great business. But Oscar is something else entirely. It is not a front-end consumer brand. It is the infrastructure layer. The system. The backbone of a new healthcare model in America.

And today, I can say this with full conviction: Oscar Health will become the largest position in my portfolio. HIMS was the start. Oscar is the core.

The Two-Stock Portfolio

I currently hold only two companies in my portfolio: HIMS and Oscar Health. I’ve studied dozens of others. I’ve explored fintech, energy, small caps, platform businesses, even global conglomerates. But nothing has matched the asymmetric upside and durable business model I see in these two.

But even within my concentrated portfolio, there is now a clear internal ranking. And Oscar Health is pulling ahead. Stronger leadership. Higher IQ in execution. A far deeper moat. And a business model that will grow more durable as it scales, not less.

Understanding the Difference

Let’s be honest. HIMS is a marketing machine. It’s a front-end business built around trust, packaging, and repeat purchase behavior. The company needs to continuously sell, convince, and convert customers. It lives and dies by CAC, LTV, and performance marketing. There’s nothing wrong with that. It’s an efficient growth engine. But it is also vulnerable. If sentiment shifts, if customer acquisition slows, or if consumer preferences change, the entire business is exposed.

Oscar is the opposite. Oscar is infrastructure. It is not selling a product. It is building a system. It is integrating itself into one of the most regulated and complex industries in the United States: health insurance. Oscar is not trying to be sleek. It’s trying to be essential.

They are rebuilding the backend of how health coverage is delivered, managed, and experienced. It is not about ads. It is about code. APIs. Data networks. Long-term contracts. Trust from regulators. Alignment with providers. That’s a different game.

A Broken Industry

Let’s take a step back and remember what industry we’re talking about.

Health insurance in the United States is fundamentally broken. Customers hate it. Denial rates are outrageous. Processes are opaque. Interfaces are outdated. There is no trust. No love. No loyalty.

Ask almost anyone in America how they feel about their health insurer. The answer is some mix of frustration, resentment, and fatigue. Now compare that with Oscar Health.

Oscar’s Net Promoter Score is among the highest in the industry. Their denial rates are dramatically lower. Their customer experience is not just better, it’s fundamentally different. People like being members. They recommend it. They stay. They engage. That doesn’t happen in health insurance by accident. It happens when you rethink the system.

And this is exactly what Oscar is doing.

Category-Defining Tech

Oscar is not a DTC brand with a tech stack. It is a software company with a full-stack healthcare infrastructure layer. They are rebuilding everything from claims processing to member onboarding to clinical insights.

And here’s the real unlock: artificial intelligence.

Oscar is one of the very few healthcare companies in the world with real access to foundational AI advantages. Not just from vendors. But from real strategic partnerships.

Josh Kushner, Oscar’s co-founder, was one of the earliest investors in OpenAI. This relationship is not for show. It is deep. Strategic. Technical. Oscar is now working closely with OpenAI to bring large language models into healthcare operations in ways no one has done before.

Think about what that means.

This is not about chatbots. This is about transforming clinical pathways, customer service, data analysis, cost prediction, and care navigation—all powered by AI. And all built into Oscar’s platform.

This is the Palantir moment of healthcare. What Palantir became for defense, Oscar will become for health insurance. A misunderstood, infrastructure-based, high-margin, category-defining software and data company.

And right now, the market is sleeping on it.

Valuation Disconnect

Oscar’s market cap is still below $4 billion. That is absurd for what they are building.

They are not a health startup anymore. They are a scaled insurer with durable premium revenue, low churn, high member satisfaction, and an expanding footprint in the ACA marketplace. They are winning market share in a growing sector.

Their platform is not a cost center. It is a competitive advantage. They have built a technology foundation that enables lower costs, better margins, and faster scale. And now, with AI integration, they are moving into a phase of exponential leverage.

This is not a hope-based 10x story. This is a mispriced 3x in the short term, with long-term optionality that could lead to 10x returns over the next decade.

Let’s be specific.

Oscar’s new CEO publicly stated that without any wild assumptions, the stock should trade between $45 and $55 by 2027. That’s a 3x from here, without needing a multiple expansion. This is not fantasy. It is the base case. No miracles required. Just continued execution.

Compare that to most tech or growth stocks where 3x requires heroic assumptions. With Oscar, it’s just about time and scale.

Institutional and Insider Alignment

Oscar is not just a high-IQ company operationally. It’s also high-IQ from a shareholder alignment perspective.

Look at the board. Look at the cap table. Thrive Capital is still in. Josh Kushner is still a major shareholder. Insider ownership is strong. The short interest is low. There is no wall of distrust. No signal of internal weakness. The team is confident and aligned.

This is the kind of setup that value investors look for. High insider skin in the game. Deep institutional backing. Long runway. Misunderstood model. Real execution. And a valuation that compresses downside risk.

From a value perspective, this is a rare opportunity.

HIMS vs. Oscar: Final Thoughts

Let me be clear.

I still believe in HIMS. It is a strong brand. It serves an unmet need. It has shown resilience in a competitive space. But when I stack it up next to Oscar Health, the comparison is no longer close.

HIMS is a great marketing engine. It is a consumer brand. A DTC story that needs constant momentum.

Oscar is the opposite. It does not sell products. It sells trust. It scales not through advertising, but through excellence in service, deep integration, and durable backend systems. It is not dependent on trend cycles. It is building something foundational.

There has not been a health insurer like Oscar since the 1970s. This is a once-in-a-generation rebuild of how Americans experience coverage. And it’s working.

Customers don’t just tolerate Oscar. They love it. It’s not push. It’s pull. People come because the alternative is broken. And Oscar is not just slightly better. It is dramatically better.

This is the kind of business that compounds quietly. That grows through scale and infrastructure, not hype. That eventually becomes a dividend-paying float machine. Think Geico. But with better technology, better margins, and fewer capital requirements.

My Move

I’m increasing my Oscar position now. I will keep buying. Month after month. Quarter after quarter. As long as the valuation remains disconnected from the value.

I believe this is the most durable, misunderstood, and asymmetric investment in healthcare today. It’s not speculative. It’s inevitable. And at these prices, the risk is low and the reward is extraordinary.

This is not just a great stock. It’s a category-defining company. It is the kind of company you can own for life.