The Barstool boomerang
According to Portnoy, the brash image he had cultivated for himself online while building the Barstool Sports business quickly collided with the heavily-regulated gambling and casino industry Penn Entertainment operates within.
“Gambling [is] super regulated, you need licenses,” he told Sharpe. “If a state regulator in Indiana doesn't like you, you're in trouble. I'm a controversial guy [and] it was definitely creating issues for Penn getting licenses.”
Penn Entertainment CEO Jay Snowden hinted at these struggles during an earnings call in 2023, Variety reported.
“Being part of a publicly held, highly regulated, licensed gaming company, it became clear that we were an unnatural owner” for Barstool Sports, he told shareholders.
Portnoy also admitted that Barstool Sports was losing money at the time. However, the ultimate trigger for the sale was Penn’s megadeal with ESPN to rebrand its sports betting service from Barstool Sportsbook to ESPN Bet, according to Variety.
As part of the deal, Portnoy agreed to repurchase Barstool and abide by specific non-compete restrictions. Penn also retains the rights to claim 50% of the gross proceeds from any subsequent sale of the company.
As of 2025, Portnoy is still the sole owner of Barstool Sports. But he claims the company’s boomerang journey taught him a key lesson about how to get rich in America.
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Learn MoreGetting rich in America
Portnoy’s roughly $550 million windfall from selling his company underscored a key lesson — building and selling a business can be one of the most powerful wealth-building tools in the U.S. economy.
Unless you're already in elite industries like finance or private equity, Portnoy believes entrepreneurship offers a real, achievable path to becoming super rich.
To be fair, entrepreneurship is just as risky as it is accessible. Anyone can start a business, but 65% of them fail within the first 10 years, according to the U.S. Chamber of Commerce.
Even a successful business might not make you super rich. In the first quarter of 2025, roughly 2,368 private businesses were acquired for a median valuation of $349,000, according to BizBuySell. That’s far from generational wealth.
To unlock tremendous, life-changing wealth, you need to start a business that is not only profitable and successful, but also scaled up in size.
A typical mid-size company’s enterprise value was $166.8 million in 2024, according to Capstone Partners and only 5% of all businesses in America are large enough to fit in this category, according to JP Morgan.
Simply put, entrepreneurship is a great way to build a fortune, but the path is much narrower and more treacherous than most people assume.
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