Mason Hawkins is a prominent American investor, known for being the founder and chairman of Southeastern Asset Management. Hawkins holds a Bachelor of Arts in Finance from the University of Florida and later did his MBA in Finance from the University of Georgia. Before founding Southeastern Asset Management, the billionaire gained experience as a Director of Research at Atlantic National Bank and First Tennessee Investment Management. There he developed his value investment strategy and has since been known for his discipline in value investing. His fund Southeastern Asset Management also holds the same reputation, which can be witnessed through his concentrated portfolio of around 40 to 50 stocks. Southeastern Asset Management services 47 clients at the moment, with $5,271,901,660 as assets under management as of March 2024.
Value investment is an investment strategy that employs buying stocks of well-managed and quality companies at prices significantly below their intrinsic value. The core of Hawkins’ strategy is to purchase equities when their market price is no more than 60% of the firm’s appraisal of their intrinsic value. Value investors believe that the market overreacts to economic news, which leads to movement in stock prices, however, this news does not affect the long-term fundamentals of a company. Therefore, investors like Mason Hawkins do not follow the herd and use financial research and analysis to find quality companies. Value investors are also known for holding companies for a long term, but also actively ferret out stock that the market is underestimating.
Hawkins’ disciplined and research-based investment strategy has earned him widespread recognition. He achieved Investor’s Lifetime Achievement Award in 2005 and was also named Domestic Equity Fund Manager of the Year by Morningstar in 2006.
Under the current market condition, Hawkins’ value investment strategy has led Southeastern Asset Management’s attention towards small-cap stocks. While the small-cap stocks have largely underperformed the market when compared to their large-cap counterparts. However, according to Francis Gannon, Co-Chief Investment Officer at Royce Investment Partners, small-caps are attractively priced for long-term investment opportunities. Gannon’s investment advice aligns with Hawkins’s strategy, as he suggests investing in quality small-cap companies with strong fundamentals, low debt, established long-term earnings, and significant upside potential.
To compile the list of billionaire Mason Hawkins’ 10 small-cap stocks with huge upside potential, we sifted through 13F filings of Southeastern Asset Management, from Insider Monkey. From these filings, we checked each stock’s upside potential from CNN and ranked the stocks in ascending order of the upside potential. We have also added the stake Southeastern Asset Management holds in each company and the hedge fund sentiment around each stock. Please note that the data was recorded on April 28, 2025. Also note that for this article we have defined small-cap companies as those with a market capitalization between $1 billion to $10 billion.
Why are we interested in the stocks that hedge funds pile into? The reason is simple: our research has shown that we can outperform the market by imitating the top stock picks of the best hedge funds. Our quarterly newsletter’s strategy selects 14 small-cap and large-cap stocks every quarter and has returned 373.4% since May 2014, beating its benchmark by 218 percentage points (see more details here).
Oscar Health, Inc. (OSCR): Among Billionaire Mason Hawkins’ Small-Cap Stocks with Huge Upside Potential
Mason Hawkins of Southeastern Asset Management
Market Capitalization: $3.06 billion
Number of Hedge Fund Holders: 43
Southeastern Asset Management Stake: $42,081,769
Analyst Upside Potential: 51.27%
Oscar Health, Inc. (NYSE:OSCR) is a health insurance company that leverages a proprietary full-stack technology platform to deliver and manage insurance. It operates through key activities and services including health insurance plans, +Oscar (Technology platform), and member services. It operates in multiple states across the United States.
During fiscal year 2024, Oscar Health, Inc. (NYSE:OSCR) achieved record ACA marketplace enrollment of 37% membership as compared to the market average of 13%. This took the total number of members to 1.8 million as of February 2025. The year was also significant because it marked the first year of annual profit. The net income of the company came in at $25.4M net income, against a $270 million loss last year.
Looking ahead, Oscar Health, Inc. (NYSE:OSCR) anticipates earnings from operations of around $225 million to $275 million. Management believes that its technology platform will enable further growth in memberships. It is one of the billionaire Mason Hawkins’ 10 small-cap stocks with huge upside potential.
Longleaf Partners Small-Cap Fund stated the following regarding Oscar Health, Inc. (NYSE:OSCR) in its Q4 2024 investor letter:
“Oscar Health, Inc. (NYSE:OSCR) – Health insurance and software company Oscar was a top detractor for the quarter while remaining a top contributor for the year. The company delivered another strong quarter operationally, achieving over 60% year-over-year revenue and membership growth, while advancing toward its publicly stated goal of 5% operating income margins. Despite the operational progress, the Trump presidential win weighed on the stock price in the quarter due to added uncertainty around the future of the enhanced ACA subsidies set to expire at the end of 2025 and broader implications for the ACA itself. Oscar still has underappreciated non-earning assets in various regions at different stages of ramp-up, transitioning from investment mode in some areas to higher-margin operations in others. We view this as a long-term positive, highlighting the embedded long-term growth potential at Oscar. While election-related news contributed to stock volatility in the second half of the year, we capitalized on the volatility by strategically trimming and adding to our position. It was powerful to see both co-founder Josh Kushner and CEO Mark Bertolini (via his foundation) each purchase more than $10 million worth of stock in the wake of the election selloff.”
Overall, OSCR ranks 5th on our list of billionaire Mason Hawkins’ small-cap stocks with huge upside potential. While we acknowledge the potential of OSCR as an investment, our conviction lies in the belief that AI stocks hold greater promise for delivering higher returns and doing so within a shorter time frame. There is an AI stock that went up since the beginning of 2025, while popular AI stocks lost around 25%. If you are looking for an AI stock that is more promising than OSCR but that trades at less than 5 times its earnings, check out our report about this cheapest AI stock.
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