Dave Portnoy sold Barstool Sports for $551M — then got it back for $1 — what to learn from this ‘great trade’
October 4, 2025 | by ltcinsuranceshopper
Club Shay Shay/YouTube
Moneywise and Yahoo Finance LLC may earn commission or revenue through links in the content below.
Shortly after selling his sports media company Barstool Sports to Penn Entertainment for $551 million in 2023, founder Dave Portnoy turned around and repurchased 100% of the company for just $1, according to Business Insider. (1)
“It’s one of the [greatest] trades of all time,” he told Shannon Sharpe in a recent interview on the Club Shay Shay podcast. (2) Sharpe then joked that the deal was “better than the Louisiana Purchase,” referring to the U.S. acquisition of around 828,000 square miles of land near the Mississippi River, then owned by France, for $15 million in 1803.
Portnoy says a combination of unique factors gave him the opportunity to pull off the sale.
Here’s why Penn let Portnoy buy back the company, and what it taught him about getting rich in America.
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. (3)
“Being part of a publicly held, highly regulated, licensed gaming company, it became clear that we were an unnatural owner [for Barstool Sports],” Snowden told shareholders.
According to Variety, the ultimate trigger for the sale was Penn’s megadeal with ESPN to rebrand its sports betting service from Barstool Sportsbook to ESPN Bet. Portnoy also admitted that Barstool Sports was losing money at the time.
As part of the deal, Portnoy agreed to repurchase Barstool and abide by specific non-compete restrictions. Penn also retained the right to claim 50% of the gross proceeds from any subsequent sale of the company.
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.
Unless you’re already in elite industries like finance or private equity, Portnoy believes entrepreneurship offers a real, achievable path to becoming very 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. (4)
Even a successful business might not make you rich. In the first quarter of 2025, roughly 2,368 private businesses were acquired for a median valuation of $349,000, according to BizBuySell. (5) That’s far from generational wealth.
To unlock life-changing wealth, you need to start a business that is not only profitable but also one that can be successfully scaled up.
Simply put, entrepreneurship can be a great way to build a fortune. However, the path is narrower and more treacherous than most people assume.
Luckily, there are plenty of other ways to build your wealth aside from starting your own business and becoming an entrepreneur.
For many, this journey starts with investing — whether in a traditional mix of stocks and bonds or with a dose of alternative assets. But figuring out where to start can be overwhelming at first.
That’s where robo-advisors like Acorns can help you build your wealth through your everyday purchases. Every time you buy something on a linked credit or debit card, Acorns automatically rounds up the price to the nearest dollar and places the excess — coins that would wind up in your pocket if you were paying cash — into a smart investment portfolio.
Acorns also give you room to grow. Once you’ve become comfortable squirrelling away a little bit of each purchase, you could set up recurring deposits to supercharge your savings.
The best part?If you sign up now, you can get a $20 bonus investment after making your first successful recurring investment of at least $5.
If you’d prefer to spend the time finding investments yourself, you could instead put your uninvested cash into a high-yield account to generate interest while picking your stocks, which is where a Wealthfront Cash Account could come in. This can also be a good place to put aside some money for an emergency fund due to the highly-liquid nature of the account.
The Wealthfront Cash Account can provide a base variable APY of 3.75%, but Moneywise readers can get an exclusive 0.50% boost over their first three months for a total APY of 4.25% provided by program banks. That’s over ten times the national deposit savings rate, according to the FDIC’s September report.
With no minimum balances or account fees, as well as 24/7 withdrawals and free domestic wire transfers, you can ensure your funds remain accessible at all times. Plus, Wealthfront Cash Account balances of up to $16 million are insured by the FDIC through program banks.
Another long-term way to grow your wealth is by investing in property.
For many Americans, this typically means getting the money together for a down payment on a house. However, there are more and more options that allow you to tap into this asset class without the trials and tribulations of managing a mortgage or becoming a landlord.
For example, you could access the rental property market by investing in shares of vacation homes or rental properties through Arrived.
Backed by world-class investors, including Jeff Bezos, Arrived allows you to invest in shares of vacation and rental properties, potentially earning a passive income stream without having to manage touchy tenants and midnight maintenance calls.
To get started, simply browse through their selection of vetted properties, each hand-picked for their potential for appreciation and income generation.
