Keith Gill (Roaring Kitty/DeepFuckingValue) made significant wealth primarily through his deeply bullish, long-term investment in GameStop (GME), starting with a $53,000 stake in 2019 and growing it as his analyses, shared on Reddit and YouTube, convinced many others, leading to massive price surges (short squeezes) and turning his initial investment into tens of millions, and eventually hundreds of millions, by holding shares and exercising call options, making him a legendary figure in the retail investing movement.
Hedge fund managers make so much because they attract massive capital by selling exclusivity, unique strategies, and the promise of high returns. While most funds don't beat the market, a few do, and investors chase those winners.
Gill caused a spike in Chewy's stock price, along with that of rival Petco Health and Wellness (WOOF), in June when he posted a comic picture of a dog on his X site. They rose again in July when it was revealed Gill held a 6.6% position in Chewy, owning 9 million shares worth about $245 million at the time.
How Much is Roaring Kitty Worth? Gill's belief in GameStop didn't just make him famous—it made him incredibly wealthy. After exercising his call options, Gill still holds 9,001,000 shares of GameStop. At today's price of $29.70 per share, those shares are worth about $267 million.
In January 2020, a tax lien for $11,795 was filed against Portnoy by the U.S. Securities and Exchange Commission. In 2019, Portnoy said his net worth was around $100 million, which was before he received his payout from Penn Entertainment.
The founders who famously turned down a $30 million offer on Shark Tank were the sisters behind the dating app Coffee Meets Bagel (Dawoon, Arum, and Soo Kang) in 2015, with Mark Cuban offering to buy the whole company, the biggest in the show's history, but they declined to keep control and grow it themselves. As of 2025, their company's net worth was estimated at $150 million, with annual revenue around $36 million, showing they made a successful decision.
A 2019 study by Harvard Business Review found either Vanguard, BlackRock or State Street is the largest listed owner of 88% of S&P 500 companies. There is a perception that a few select companies own a vast majority of the stock market.
The richest hedge fund managers consistently include Ken Griffin (Citadel), leading with fortunes estimated over $50 billion, followed by major figures like Ray Dalio (Bridgewater Associates), Steve Cohen (Point72), and David Tepper (Appaloosa Management), with recent reports from Forbes showing their combined wealth growing substantially, highlighting massive gains in the hedge fund industry.
The "24-year-old trader making $8 million" refers primarily to Jack Kellogg, a successful day trader who reported over $8 million in gains from trading in 2020 and 2021, starting with just $7,500 and leveraging key indicators like VWAP, support/resistance, volume, and linear regression for simple, adaptable strategies. His story highlights achieving significant returns by weathering different market conditions, learning from losses, and sticking to core principles rather than overcomplicating things.
Even the stories of some of the traders Dumb Money was based on, and who I talked to for this story, are far from cut and dried. Some big names lost money on GameStop, but others made a bundle. The same goes for everyday investors — some won, some lost, and plenty were just in it for the casino-like ride.
During an appearance on The Sage Steele Show in November 2024, Portnoy shared for the first time that Renee still has access to his bank accounts, explaining that they are still legally married. "We met when Barstool was nothing, so she rode the grind up with us," he said.
Netflix is paying Barstool Sports an eight-figure sum annually, reportedly over $10 million per year, for exclusive video streaming rights to popular podcasts like Pardon My Take, Spittin' Chiclets, and The Ryen Russillo Show, as part of a multiyear deal to expand its sports podcast content.
As of June 13, 2024, Gill's net worth includes more than 9 million GameStop shares valued at $262 million, and about $6.3 million in cash. He owns 6.6% of online retailer, Chewy, stock. Gill stepped away from his online accounts in 2021 before returning in May 2024.
#7: Gill's Sister Passed Away
Keith and Kevin lost their sister Sara Gill on June 25, 2020, at age 43. The movie mentions that her death was unexpected, but it doesn't delve into how Sara died.
While the short squeeze was initially reported as being driven by retail investors, it later emerged that a substantial part of the market activity surrounding GameStop and the related securities was conducted by hedge funds, who had made substantial profits from the short squeeze.
Investing $10,000 in Apple (AAPL) stock in 1990 would have yielded an astronomical return, making you a multimillionaire many times over by today, with calculations suggesting it would be worth tens of millions of dollars (or potentially over $100 million with dividends reinvested) due to incredible growth, stock splits, and the success of products like the iPhone, though exact figures vary slightly based on calculation dates and dividend reinvestment, Yahoo Finance.
Investing $100 in Bitcoin about 10 years ago (around late 2015/early 2016) would have turned that initial amount into tens of thousands of dollars, potentially over $30,000, given Bitcoin's massive growth from roughly $300-$400 per coin to over $100,000 by late 2025/early 2026, though exact value depends on the specific purchase price and current market fluctuations, representing an astronomical return but also highlighting Bitcoin's extreme volatility.