When CVS Health dropped a staggering $10.6 billion to swallow Oak Street Health back in 2023, the world caught a glimpse of what massive value-based healthcare looks like in dollars and cents. But for Mike Pykosz, the guy who co-founded the thing in a small Chicago office, it wasn't just a corporate merger. It was a payday that vaulted him into a completely different tax bracket. Honestly, tracking Mike Pykosz net worth is like looking at a masterclass in timing your exit from the public markets.
Most people assume these tech and health founders are billionaires overnight. It's rarely that simple. Pykosz didn't just wake up with a vault full of gold coins; he spent over a decade grinding through the "unprofitable" years of primary care before the math finally turned in his favor.
How much is Mike Pykosz worth right now?
As of early 2026, experts and insider trading trackers peg Mike Pykosz net worth at roughly $321 million.
This isn't a random guess. It’s based on the cold, hard numbers filed with the SEC. When the CVS deal went through at $39 per share in cash, Pykosz was sitting on a mountain of Oak Street Health (OSH) stock. We’re talking over 8.2 million shares. You do the math—actually, I’ll do it—and you’re looking at a cash-out north of $320 million just from that single transaction.
But wait. There’s more to the pile.
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Before the acquisition, Pykosz was pulling a total compensation package that would make most surgeons weep. In 2022 alone, his total compensation was listed at over $13.5 million. Most of that wasn't cash in a suitcase, though. It was a mix of stock awards and options designed to keep his skin in the game. His base salary? A relatively "modest" $561,000.
Breaking down the fortune
- The Big Cash-Out: The $39-per-share acquisition by CVS is the primary driver.
- Executive Salary: Millions earned during his tenure as CEO of Oak Street and later as an EVP at CVS.
- Historical Stock Sales: SEC Form 4 filings show a steady drumbeat of sales over the years—$2 million here, $4 million there—long before the final buyout.
- Investments: While he keeps his private portfolio quiet, someone with $300 million isn't just letting it sit in a savings account.
The CVS transition and the 2024 departure
Life inside a Fortune 500 company is different from the startup world. Pykosz stayed on after the merger to lead the healthcare delivery arm of CVS. He was the "President of Health Care Delivery," a title that sounds fancy because it is. He was tasked with scaling Oak Street from its 170 locations toward a goal of 300+ centers by 2026.
Then, in late 2024, things shifted.
CVS was going through some... let's call it "corporate turbulence." High-level ousters were happening left and right. Surprisingly, Pykosz wasn't one of the people pushed out. He left voluntarily. He basically told the top brass earlier that year that he was ready to move on. He officially stepped down in December 2024.
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When a founder leaves an 18-month post-merger gig, it usually means their "golden handcuffs" have finally unlocked. He’d done his time, integrated the company, and likely saw his final tranches of compensation vest.
Why Oak Street Health was worth so much
You might wonder why a chain of doctor's offices for seniors was worth $10.6 billion. It’s about the "value-based" model. Instead of getting paid for every test a doctor runs (fee-for-service), Oak Street gets a flat fee to keep patients healthy. If they stay out of the hospital, Oak Street keeps the savings.
Pykosz and his team (Geoff Price and Griffin Myers) bet big that they could manage chronic diseases better than the traditional system. They were right. Or at least, they were right enough for CVS to decide they couldn't live without that model to fuel their Aetna Medicare Advantage plans.
The "Hidden" Assets
Is $321 million the absolute ceiling? Probably not. That figure mostly tracks the publicly visible stock and reported salaries. It doesn't account for:
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- Real Estate: High-net-worth individuals in Chicago and beyond typically hold significant property.
- Private Equity: It’s common for founders of his caliber to reinvest in the next generation of health-tech startups.
- Taxes: Let’s be real, Uncle Sam took a massive bite out of that $321 million. Capital gains taxes on a $10 billion acquisition exit are no joke.
What’s next for the $300 million man?
Mike Pykosz is young. He’s got a JD from Harvard and a biochemistry degree from Notre Dame. He isn't the type to just sit on a beach for the next thirty years. Since leaving CVS in late 2024, he’s been popping up on podcasts like Heart of Healthcare, talking about the "unprofitable" care models and the future of American medicine.
Whether he starts a new venture or becomes a kingmaker in venture capital, his financial legacy is already cemented. He turned a risky idea about senior care into one of the biggest healthcare exits of the decade.
Actionable Insights for Investors and Founders
If you're looking at Pykosz's career to figure out how to build your own wealth, here are the takeaways:
- Focus on the Payer: Pykosz didn't just build clinics; he built a system that saved insurance companies money. That’s where the real "exit" value lives.
- Equity is Everything: The $561k salary was a distraction. The $320 million came from the 8.2 million shares. If you aren't getting equity, you aren't building real net worth.
- Timing the Market: Oak Street went public during the COVID-19 boom when healthcare valuations were soaring. They sold to CVS when the window for "standalone" value-based care companies began to tighten.
- The 18-Month Rule: If you sell your company, expect to stay for at least 18 to 24 months to ensure the "handover" works. That's usually when the final big checks clear.
Mike Pykosz net worth is a testament to the fact that in the 2020s, the biggest "gold mine" isn't in tech or crypto—it's in fixing the broken mechanics of how we pay for staying alive.