(NewsNation) — Barstool Sports owner Dave Portnoy has made a name for himself in the sports media space, having amassed millions of fans through his colorful sports commentary and brand.
The 48-year-old businessman and internet personality is worth $250 million, according to Celebrity Net Worth.
Portnoy’s net worth not only stems from his massively successful business, but stocks and real estate holdings, according to Celebrity Net Worth.
Who is Dave Portnoy?
The Massachusetts-born Portnoy, who, despite earning a bachelor’s degree in education at the University of Michigan, ended up working for Yankee Group, an IT market research company in Boston, after college.
However, while at college, Portnoy, a lifelong gambler, founded the website thegamblingman.com to publish his sports picks.
Dave Portnoy filed for bankruptcy
At 26 years old, Portnoy filed for bankruptcy protection in 2004 after he lost $30,000 gambling in one year, according to the New York Times.
He reportedly owed $59,000 to credit card companies and $18,000 to his father, Mike Portnoy, who has called him a “degenerate” over his gambling issues.
Dave Portnoy looks on prior to Game 4 of the 2024 NBA Finals between the Dallas Mavericks and the Boston Celtics at American Airlines Center in Dallas on June 14, 2024. 
The Barstool Sports logo on a laptop arranged in New York, US, on Tuesday, Jan. 23, 2024. A partnership with Dave Portnoy’s Barstool Sports is powering shares of video platform Rumble Inc. higher. Photographer: Gabby Jones/Bloomberg via Getty Images 
In an image taken from Monday, July 15, 2024, video, provided by Dave Portnoy, Portnoy speaks about his rescue at sea by the U.S. Coast Guard off the coast of the island of Nantucket, Mass. The Coast Guard confirms it rescued the founder of the Barstool Sports website after a boating accident off of Nantucket. (Dave Portnoy via AP)
“Anybody who thinks that my son is exaggerating his gambling issues, I wish he was,” he said in 2019 on Barstool Radio. “Believe me, he is a legitimate degenerate.”
Dave Portnoy finds success in media
Portnoy founded Barstool Sports, a sports newspaper, in 2003, which he would hand out to Boston commuters.
The paper provided readers with sports predictions, gaming ads and sports coverage, per Celebrity Net Worth.
In 2007, he launched the Barstool website, and within a decade, it became a well-known brand in sports media.
Portnoy sold a stake in Barstool Sports to the investment company Chernin Group in 2016, valuing it at up to $15 million, the New York Times reported. Within two years, the firm invested between $20 million and $25 million to own 60% of Portnoy’s company.
According to Celebrity Net Worth, the Barstool Sports founder retained complete control of the company content, which grew into podcasting, gambling content, merchandise, alcohol brands and TV shows.
Penn National Gaming acquired a 36% stake in the company in January 2020, valuing it at $450 million.
Within three years, Portnoy regained 100% ownership of Barstool Sports amid market fluctuations.
Dave Portnoy’s real estate portfolio
As of October 2025, Portnoy owns $100 million in real estate, having recently purchased a $28 million mansion in Florida, Celebrity Net Worth reports.
He bought a home in Nantucket for $2 million in 2015. In 2023, he spent an eye-watering $42 million on a six-bedroom, 8,600 square foot waterfront mansion in Nantucket’s Monomoy area.
He’s bought other property in recent years, including a 1930s-era mansion in Miami for nearly $14 million, a $9.75 million home in Montauk, New York and a $1.4 million home in New York’s Saratoga Springs.