Rich Dudes│Barstool's Dave Portnoy Line Drive to $100M Net Worth

Dave Portnoy is a media personality and entrepreneur who has made a name for himself as the founder of the wildly popular sports and pop culture blog Barstool Sports. What started as a hobby while working at a pizza shop in 2003 turned into a multimedia company with a devoted fan base and a strong online presence.

You might be wondering how a sports blogger managed to accumulate wealth totaling $100 million. Here's a play-by-play of how Portnoy became a millionaire.

David Portnoy was born in Swampscott, Massachusetts on March 22, 1977. After leaving Swampscott High School, he secured his college degree in education from the University of Michigan in 1999. He relocated to Boston upon graduation and began working for the IT market research firm Yankee Group.

In 2003, Dave started Barstool Sports as a print magazine for the Boston metropolitan area. The newspaper featured sports journalism, gambling advertisements, and fantasy sports predictions. Although Barstool Sports started in 2003, the website only launched in 2007. Over the next ten years, Barstool would become an unlikely sports media powerhouse.

Dave is known online as "El Presidente" or "Stool Presidente." The website features both hot women and caustic sports news. The company's image has been equated to the lovechild of ESPN and Playboy.

In 2017, Dave started a pizza review series called "One Bite with Davey Pageviews" which began by rating every pizzeria in Manhattan and later expanded to pizza joins across the country.

In January 2016, a controlling share in Barstool was reportedly purchased by Peter Chernin's The Chernin Group for $10 to $15 million. By the end of 2018, Chernin increased his interest to 60% by investing $20 to $25 million. Portnoy maintained complete ownership of the company and was running its day-to-day activities, TV series, souvenirs, gambling-related content, podcasts, and more.

Penn National Gaming (now called Penn Entertainment) purchased a 36% share in Barstool Sports in January 2020 at a $450 million valuation. The initial cash transactions totaled $163 million. Additionally, Penn National Gaming acquired the right to increase its ownership to 50% by spending an additional $62 million within three years.

The Chernin Group's 60% interest was then brought down to 36%, matching Penn's holding. Portnoy and a few other senior executives, including CEO Erika Nardini, together retained a 28%.

Now, here’s where it gets more interesting—shares of Penn Gaming soared to an all-time high of $38 in the days following the announcement and eventually fell during the global pandemic. By March 17, the stock had fallen 81% to $7 per share.

During the initial acquisition, about $23 million of the $163 million in cash was granted as convertible preferred stock, and $3 million was set aside for "forward arrangements" per a Penn Gaming SEC filing in Q1 of 2020. That means the stock may be converted into 883,000 Penn Gaming shares, or around 0.50% equity in Penn Gaming.

A 0.50% of Dave’s stake in Penn Gaming was worth $50 million when its market capitalization was $10 billion. According to reports, Dave owned a third of that investment, which came to about $16 million (at a market cap of $10 billion). When we combine this with his $90 million stake in Barstool, we can then conclude that Dave Portnoy's net worth is at least $100 million.

Eventually, Penn Gaming acquired an additional 14% of Barstool, growing its stake in the sports media company to 50%. Penn Entertainment then exercised its right to purchase the remaining shares of Barstool, according to an SEC filing made on Wednesday, August 17, 2022. 

To complete it's acquisition of Portnoy's brand, Penn spent another $338 million at the beginning of 2023. In total, Penn had spent over $550 million to acquire Barstool Sports.

Dave Portnoy bought back the rights to the Barstool sports brand for $1 according to an SEC filing dated June 30, 2023.

Barstool Sports founder and American social media personality Dave Portnoy boasts a diverse investment portfolio elevating his net worth to new heights. His real estate assets include a swanky Miami home, a quaint Nantucket island abode, and a luxurious Hamptons beach house. 

As a stakeholder in Penn Entertainment, he cleverly navigates the stock market and dabbles in cryptocurrency for good measure. From pizza reviews to savvy investments, El Prez sure knows how to score big.

Dave Portnoy has made some significant investments in real estate over the years. In 2021, he purchased a $14 million home in Miami, which has since appreciated by approximately 21% to a current value of around $17 million.

In addition to his Miami property, Portnoy also owns a home on Nantucket island, which he purchased for $2 million in 2015. Based on an assumed yearly growth rate of 21%, this property could be sold for around $7.6 million today.

More recently, in 2022, Portnoy invested in a Hamptons beach house, purchasing it for $9.75 million. As this property was purchased more recently, so it probably hasn't appreciated in value yet.

Investing in real estate can be a great way to diversify your portfolio and potentially earn passive income. According to the Case-Shiller national homeprice index, U.S. residential real estate was the best performing asset in 2022, outpacing both alts and traditional assets, alike.

Dave Portnoy is the founder of Barstool Sports and a former day trader. He has made significant investments in stocks, including Penn, a gambling company that is one of the majority owners of Barstool. In fact, Portnoy sold his stake in Barstool to Penn, which now owns 100% of the company, having purchased the remaining shares for $387 million.

According to Portnoy, his net worth is tied to this one stock, with the rest of his net worth estimated at around $42 million. This means that he likely has around $39 million invested in Penn.

Portnoy also succeeded as a day trader, with estimated profits of $2 million. He even made at least $1 million from a single trade. In the past, Portnoy has also owned stock in Spirit Airlines.

During the pandemic, Portnoy put $5 million into various investments, though it's assumed that he still has about that amount invested in various stocks. He has stated that he is "done" with day trading at the end of the pandemic.

Dave Portnoy recently launched a watch company, which has faced criticism and negative attention on the internet. As the company is less than a month old, it's difficult to determine its value. Starting a watch company typically requires an estimated $3 to $4 million, so it's assumed that Portnoy's company is on the lower end of this range.

It's unclear if Portnoy's has any past ventures or experience in the watch industry have been.

Davey Pageviews has dabbled in cryptocurrency, including a $40,000 investment in Memecoin SafeMoon, which is now worth around $2,300. Despite how SafeMoon turned out to be a huge crypto scam, Dave Portnoy's net worth didn't take a huge hit.

Portnoy was also a relatively early bitcoin investor, but lost an unknown amount to the FTX crash. It's known that he bought $15,000 to $20,000 worth of BTC at a price of around $7,000, but it's unclear what his Bitcoin holdings are worth today.