Dave Portnoy: Barstool Founder’s Controversies & Memecoins

Dave Portnoy, the outspoken founder of Barstool Sports, is no stranger to making waves, whether in the world of media, stock trading, or, now, cryptocurrency. Known for his brash personality and unfiltered views, Portnoy first dipped his toes into Bitcoin in 2020, making a high-profile purchase after a meeting with the Winklevoss twins. While his initial foray was short-lived (he sold at a loss and famously declared, “I will never buy Bitcoin again”), his journey into the crypto space was far from over.

Since then, Portnoy has returned to Bitcoin multiple times, explored altcoins, and—true to his brand—embraced the chaotic world of meme coins. His involvement in these highly speculative assets has been entertaining and controversial, with massive gains, painful losses, and no shortage of viral moments along the way. Love him or hate him, Portnoy’s crypto journey is a testament to the industry’s rollercoaster nature and the mainstream appeal of digital assets in the age of social media.

Dave Portnoy: Summary of the Barstool Sports Founder

It may be fair to classify Dave Portnoy as the most famous, and one of the wealthiest, retail crypto traders. Portnoy has made many of the most basic retail trading mistakes, and like many in crypto, has also experienced some amazing wins. However, as an entrepreneur, he has been nothing short of ambitious and hard working. His motto is clear – “Promise big, deliver big” – Something that he has tried to do with his business ventures. According to Portnoy’s parents, Dave has always had a spirit to question everything around him. In his childhood days, he was exceptionally good at playing baseball. Later during his college years, his interest shifted more towards the gambling industry. Well, all this goes to say, Dave Portnoy’s path to discovering cryptocurrencies has been truly fascinating.

Who is Dave Portnoy?

Dave Portnoy is a businessman, media personality, and the larger-than-life founder of Barstool Sports, one of the most influential sports and pop culture brands in the United States. Known for his brash attitude, unfiltered opinions, and fearless marketing tactics, Portnoy has built a devoted following that stretches from die-hard sports fans to retail traders and crypto enthusiasts. His ability to entertain and stir controversy in equal measure has made him a polarizing yet undeniably impactful figure in modern media.

Beyond his sports media empire, Portnoy has ventured into various industries, including stock trading, pizza reviews, and most recently, cryptocurrency. His financial moves—often shared in real-time with millions of followers—have turned him into an accidental finance influencer, earning him a place at the intersection of traditional investing and internet culture. Whether he’s making bold claims about stocks, pumping memecoins, or challenging the financial establishment, Portnoy remains one of the most entertaining and unpredictable personalities in business today.

Early Career and the Founding of Barstool Sports

Before he became “El Presidente” of Barstool Sports, Dave Portnoy was just another guy with a dream and a passion for sports betting. The Barstool owner was born in 1977 in Swampscott, Massachusetts. He later studied at the University of Michigan, where he earned a degree in education. After a brief stint working in sales, Portnoy decided to take a risk and launch Barstool Sports in 2003 as a small, free sports newspaper catering to the Boston area. The publication focused on gambling picks, fantasy sports, and sports culture, with a humor-driven edge that quickly resonated with young audiences.

As the internet grew, so did Barstool. Portnoy took the brand digital, launching BarstoolSports.com and leveraging social media to build a fiercely loyal audience. By the late 2010s, Barstool had evolved from a niche sports blog into a multi-million-dollar media empire with viral content, podcasts, and partnerships spanning sports, entertainment, and betting. Portnoy’s aggressive, no-apologies style helped him stand out in an increasingly corporate media landscape, making Barstool a unique cultural force.

Dave Portnoy’s Entry into Crypto

Portnoy’s first serious encounter with cryptocurrency came in August 2020, when he invited the Winklevoss twins—early Bitcoin investors and founders of Gemini—to his house for a crash course on Bitcoin.

During the interview, the Winklevoss twins provided insights into Bitcoin’s potential as “digital gold” and its role in the future of finance. Portnoy, known for his candid demeanor, asked probing questions, expressing both skepticism and curiosity. This conversation not only highlighted the growing mainstream interest in cryptocurrency but also showcased the educational efforts by established crypto entrepreneurs to demystify the space for newcomers.

For those interested in viewing this engaging discussion, the full interview is available below:

Impressed by their pitch, Portnoy invested $250,000 into Bitcoin and Chainlink (LINK). However, after a volatile week and some losses, he quickly sold everything and dramatically declared he was “out” of crypto for good.

But as with many who get their first taste of crypto, Portnoy couldn’t stay away. Over time, he found himself drawn back into the space, dabbling in memecoins like SafeMoon and openly discussing Bitcoin as a legitimate store of value. Though he still jokes about his lack of technical knowledge, his stance on Bitcoin has evolved, and he now acknowledges its staying power.

His rollercoaster relationship with crypto has made him a relatable figure for many retail investors—someone who dives in headfirst, learns through trial and error, and isn’t afraid to admit when he’s wrong (or double down when he’s right). The fact that he isn’t a crypto native or an industry insider help to make him a fan favorite. He doesn’t have any real edge against other retail investors (other than capital). If Dave can have success trading crypto than so can the average crypto retail investor.

Pro Tip: Now, if as an average retail investor you don’t know what cryptocurrencies to buy, consider checking out our article on Top 20 Best Crypto to Buy Now in March 2025

Dave Portnoy’s Biggest Wins and Losses in Crypto

Dave Portnoy’s crypto journey has been anything but boring, filled with big swings, viral moments, and some expensive lessons. Like many retail investors, he’s had both notable wins and frustrating losses, often playing out in real-time for his millions of followers.

One of Portnoy’s most infamous crypto blunders came in 2020 when he bought Bitcoin and Chainlink at the peak of a market rally—only to panic-sell shortly after when prices dipped. That beginner mistake of paper handing Bitcoin and selling for a loss, earned him the title of dumb money Dave Portnoy to some, but that’s only part of his story.

He later admitted that selling so soon was a mistake, especially as Bitcoin continued to climb to new all-time highs. Another misstep was his involvement with SafeMoon, a highly speculative memecoin. After publicly endorsing it and investing $40,000, he later claimed he lost nearly all of it, calling himself the “unofficial leader of SafeMoon” before eventually disowning it when its price tanked.

Despite these losses, Portnoy has had some victories in crypto as well. In 2021, he finally re-entered Bitcoin, purchasing one full BTC at around $48,000 and holding onto it through market turbulence. He’s also expressed a growing appreciation for the long-term potential of Bitcoin as a store of value, stating that he now understands the appeal of holding onto it rather than day-trading. His ability to laugh at his own mistakes, while still diving back in, has made him one of crypto’s most entertaining personalities—someone who embodies the highs and lows of the retail investor experience.

Dave Portnoy’s Controversies

While Dave has been a huge crypto supporter, his actions and words have always been questioned by crypto community. So much so that some crypto analysts accuse him of constantly supporting pump-and-dump schemes. Surprisingly, many in the industry are even questioning if ‘Dave will go to jail in 2025’. But according to the Polymarket bet, there was only 9% chance of him being imprisoned, at the time of writing.

Dave Portnoy And His Jailstool Controversy

In early February 2025, Dave Portnoy, founder of Barstool Sports, became entangled with a memecoin named Jailstool ($JAILSTOOL), inspired by an inside joke about him potentially facing jail time. Portnoy’s promotion of the token led to a meteoric rise, with its market capitalization surging by 119,000% in less than five hours. However, the token’s value later plummeted by 80% due to market volatility and concerns over large investors offloading their holdings. Despite the downturn, Portnoy remained committed, stating,

The Libra Confusion

Dave Portnoy’s foray into crypto took another turn with the launch of Libra ($LIBRA), a meme coin inspired by his astrological sign. Portnoy promoted the token to his followers, leading to a significant price surge, as is common with influencer-driven crypto projects. However, the token quickly became the subject of controversy when Portnoy returned 6 million Libra tokens to the project’s founder, Hayden Davis, claiming he had been advised not to disclose his compensation for promoting the token. He later put out a tweet highlighting the risks of investing in memecoins.

Adding to the confusion, another token named Libra made headlines in Argentina after it was publicly endorsed by President Javier Milei. Unlike Portnoy’s memecoin, this Argentine Libra token was positioned as a cryptocurrency aimed at revitalizing the country’s struggling economy. However, it quickly collapsed, leading to massive losses for investors and sparking political controversy, with Milei facing accusations of fraud and impeachment calls. The two Libra tokens were completely unrelated, but the coincidence led to widespread confusion in crypto circles, with some mistakenly associating Portnoy’s memecoin with the Argentine scandal.

Despite the turbulence, Portnoy’s Libra ($LIBRA) remains active, with the Barstool founder continuing to engage with the crypto community—albeit with a more cautious approach following the controversy.

Pure Greed

Dave Portnoy’s involvement in memecoins took another twist in February 2024 with $GREED, a cryptocurrency project that quickly stirred up controversy. Known for his bombastic personality and unapologetic approach to business, Portnoy embraced $GREED as yet another high-risk, high-reward play in the crypto space. The token, which launched with the usual social media hype, positioned itself as a community-driven asset, but it wasn’t long before accusations of insider dealings and potential manipulation surfaced.

Critics pointed out that Portnoy had received a large allocation of $GREED tokens, which he initially denied planning to dump. However, as price volatility increased and concerns about the token’s legitimacy spread, some investors accused Portnoy of using his influence to artificially pump the price. In response to the backlash, Portnoy attempted to clear the air on February 5, 2024, stating,

Despite Portnoy’s insistence that his involvement was genuine, $GREED quickly lost momentum in the days following his endorsement, with many early investors selling off their holdings as trust in the project dwindled. The controversy further fueled debates about the ethics of celebrity-backed cryptocurrencies, with some arguing that figures like Portnoy wield too much influence over speculative assets. While Portnoy remains undeterred, the $GREED saga serves as yet another cautionary tale about the volatile and often unpredictable nature of memecoins.

Is Dave Portnoy Good For Crypto?

Dave Portnoy’s presence in the crypto world has been nothing short of polarizing. While some see him as a charismatic figure bringing mainstream attention to Bitcoin and altcoins, others argue that his erratic investment style, frequent flip-flopping, and involvement in questionable memecoins do more harm than good. His high-profile endorsements have drawn both excitement and skepticism, with critics accusing him of chasing hype rather than fostering genuine adoption or education in the space.

One of the biggest concerns surrounding Portnoy’s crypto involvement is his lack of consistency. After first entering Bitcoin in 2020, he famously sold his holdings after a short-lived price drop, only to return months later with renewed enthusiasm. Similarly, his forays into memecoins—most notably SafeMoon, $GREED, and Libra—have often ended with rapid declines in token value and accusations of pump-and-dump schemes. While Portnoy denies any wrongdoing, many in the crypto community question whether his influence attracts long-term investors or simply fuels short-term speculation. Consider this one tweet, for instance –

On the other hand, Portnoy’s massive audience and ability to spark viral interest in financial markets have undeniably introduced more people to crypto. His raw, unfiltered approach to investing resonates with retail traders who might otherwise feel alienated by traditional finance. He represents a gambler’s mentality—high risk, high reward—that aligns with the culture of memecoins and speculative trading. Some argue that this kind of exposure, even if chaotic, ultimately benefits the industry by drawing more eyes to the space.

So, is Dave Portnoy good or bad for crypto? The answer depends on perspective. For those who see crypto as a long-term technological revolution, his antics may be a distraction that reinforces the stereotype of digital assets as speculative gambling tools. But for those who embrace the wild, unregulated, and meme-fueled nature of crypto, Portnoy is simply playing the game as it was meant to be played. Love him or hate him, his impact on the space is undeniable.

Dave Portnoy’s Net Worth and Crypto Holdings

Dave Portnoy’s net worth is estimated to be around $100 million, largely stemming from his role as the founder of Barstool Sports. His financial success skyrocketed after he sold a majority stake in Barstool to Penn Entertainment in 2020 for $450 million, though he later repurchased the company. Beyond Barstool, Portnoy has built a reputation as a stock market trader and social media influencer, leveraging his massive following to generate revenue through brand deals, merchandise, and personal investments.

Now, how much does crypto contribute to his net worth? To put it short, most likely crypto does not make up a large percentage of Dave’s overall net worth.

In 2020, he famously bought $1.25 million worth of Bitcoin, only to panic-sell shortly after. Since then, he has dabbled in various crypto projects, including Bitcoin, memecoins like SafeMoon and $GREED, and more recently, the controversial Libra token. While the exact value of his crypto holdings remains unknown, in early 2024 he reportedly owned more than $1 million in Bitcoin and another $1 million in XRP. That is in addition to his memecoin holdings. Given his ongoing interest in the space, his crypto portfolio likely fluctuates as he engages in new projects and trends.

Conclusion: Who is Dave Portnoy?

Dave Portnoy’s journey through the world of Bitcoin, crypto, and memecoins has been anything but conventional. From his initial dive into Bitcoin in 2020 to his high-profile involvement in projects like SafeMoon, Libra, and $GREED, Portnoy has remained a loud and unpredictable voice in the space. His presence has brought mainstream attention to crypto, introducing new audiences to the market, but has also fueled controversy due to his impulsive investment decisions and involvement in speculative tokens.

Portnoy has embodied the retail crypto buyer throughout his entire foray into digital assets. From buying market tops and selling into fearful markets, to slowly learning the benefits of dollar cost averaging, retail users of all types can relate something about Dave. Portnoy has continued to grow more crypto savvy over time just as retail traders continue to grow more familiar with the industry.

Whether seen as a crypto champion or a reckless gambler, Portnoy’s impact on the industry is undeniable. His influence underscores the ongoing clash between traditional finance, meme culture, and the decentralized future of money. As crypto continues to evolve, figures like Portnoy will likely remain part of the conversation, serving as both an entertainer and a cautionary tale in the ever-volatile world of digital assets.

See Also:

• Vitalik Buterin: Net Worth, Crypto Portfolio, and More
• Who is ZachXBT? Scams Exposed and Crypto Holdings
• Who is Raoul Pal? Net Worth, Crypto Holdings, and More

Frequently Asked Questions

References

• Bloomberg. “Dave Portnoy Buys Back Barstool Sports for $1 After Selling It for Millions.” Bloomberg, https://www.bloomberg.com/news/articles/2023-08-08/dave-portnoy-buys-barstool-sports-back-for-1-from-penn.
• CoinDesk. “Dave Portnoy Dives into Bitcoin Again, This Time for Good.” CoinDesk, https://www.coindesk.com/markets/2023/06/06/dave-portnoy-buys-bitcoin-again.
• Decrypt. “Dave Portnoy’s Libra Token Sparks Confusion Amid Argentina’s Crypto Efforts.” Decrypt, https://www.decrypt.co/2024/02/12/dave-portnoy-libra-token-confusion-argentina.
• Fox Business. “Dave Portnoy Says He Lost $700K in SafeMoon, Calls Crypto a ‘Scam’.” Fox Business, https://www.foxbusiness.com/markets/dave-portnoy-lost-700k-safemoon-crypto.
• The Block. “Dave Portnoy and the $GREED Token: Another Crypto Controversy.” The Block, https://www.theblock.co/post/2024/02/14/dave-portnoy-greed-token-controversy.
• Business Insider. “Barstool’s Dave Portnoy Launches Jailstool NFT Collection Amid Legal Scrutiny.” Business Insider, https://www.businessinsider.com/dave-portnoy-jailstool-nft-controversy-2024.
• Forbes. “Dave Portnoy on Crypto, Bitcoin, and His Love-Hate Relationship with Digital Assets.” Forbes, https://www.forbes.com/sites/2024/02/10/dave-portnoy-bitcoin-crypto.