Membership Shay Shay/YouTube Moneywise and Yahoo Finance LLC might earn fee or income by way of hyperlinks within the content material under. Shortly after promoting his sports activities media firm Barstool Sports activities to Penn Leisure for $551 million in 2023, founder Dave Portnoy circled and repurchased 100% of the corporate for simply $1, in accordance with Enterprise Insider. (1) “It’s one of the [greatest] trades of all time,” he advised Shannon Sharpe in a latest interview on the Membership Shay Shay podcast. (2) Sharpe then joked that the deal was “better than the Louisiana Purchase,” referring to the U.S. acquisition of round 828,000 sq. miles of land close to the Mississippi River, then owned by France, for $15 million in 1803. Portnoy says a mixture of distinctive components gave him the chance to tug off the sale. Right here’s why Penn let Portnoy purchase again the corporate, and what it taught him about getting wealthy in America. Based on Portnoy, the brash picture he had cultivated for himself on-line whereas constructing the Barstool Sports activities enterprise shortly collided with the heavily-regulated playing and on line casino trade Penn Leisure operates inside. “Gambling [is] super regulated, you need licenses,” he advised 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 Leisure CEO Jay Snowden hinted at these struggles throughout an earnings name in 2023, Selection 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 advised shareholders. Based on Selection, the last word set off for the sale was Penn’s megadeal with ESPN to rebrand its sports activities betting service from Barstool Sportsbook to ESPN Guess. Portnoy additionally admitted that Barstool Sports activities was shedding cash on the time. As a part of the deal, Portnoy agreed to repurchase Barstool and abide by particular non-compete restrictions. Penn additionally retained the proper to assert 50% of the gross proceeds from any subsequent sale of the corporate. Learn extra: Listed here are 5 easy methods to develop wealthy with actual property — whether or not you’ve got $10 or $100,000 to speculate Portnoy’s roughly $550 million windfall from promoting his firm underscored a key lesson: Constructing and promoting a enterprise may be probably the most highly effective wealth-building instruments within the U.S. Story Continues Except you are already in elite industries like finance or non-public fairness, Portnoy believes entrepreneurship presents an actual, achievable path to turning into very wealthy. To be truthful, entrepreneurship is simply as dangerous as it’s accessible. Anybody can begin a enterprise, however 65% of them fail inside the first 10 years, in accordance with the U.S. Chamber of Commerce. (4) Even a profitable enterprise may not make you wealthy. Within the first quarter of 2025, roughly 2,368 non-public companies had been acquired for a median valuation of $349,000, in accordance with BizBuySell. (5) That’s removed from generational wealth. To unlock life-changing wealth, it’s essential to begin a enterprise that’s not solely worthwhile but additionally one that may be efficiently scaled up. Merely put, entrepreneurship may be a good way to construct a fortune. Nonetheless, the trail is narrower and extra treacherous than most individuals assume. Fortunately, there are many different methods to construct your wealth apart from beginning your personal enterprise and turning into an entrepreneur. For a lot of, this journey begins with investing — whether or not in a standard mixture of shares and bonds or with a dose of other property. However determining the place to start out may be overwhelming at first. That’s the place robo-advisors like Acorns will help you construct your wealth by way of your on a regular basis purchases. Each time you purchase one thing on a linked credit score or debit card, Acorns robotically rounds up the worth to the closest greenback and locations the surplus — cash that may wind up in your pocket for those who had been paying money — into a wise funding portfolio. Acorns additionally offer you room to develop. When you’ve grow to be snug squirrelling away somewhat bit of every buy, you possibly can arrange recurring deposits to supercharge your financial savings. The very best half?Should you enroll now, you may get a $20 bonus funding after making your first profitable recurring funding of not less than $5. Should you’d choose to spend the time discovering investments your self, you possibly can as an alternative put your uninvested money right into a high-yield account to generate curiosity whereas choosing your shares, which is the place a Wealthfront Money Account may are available in. This may also be an excellent place to place apart some cash for an emergency fund because of the highly-liquid nature of the account. The Wealthfront Money Account can present a base variable APY of three.75%, however Moneywise readers can get an unique 0.50% enhance over their first three months for a complete APY of 4.25% offered by program banks. That’s over ten instances the nationwide deposit financial savings fee, in accordance with the FDIC’s September report. With no minimal balances or account charges, in addition to 24/7 withdrawals and free home wire transfers, you may guarantee your funds stay accessible always. Plus, Wealthfront Money Account balances of as much as $16 million are insured by the FDIC by way of program banks. One other long-term option to develop your wealth is by investing in property. For a lot of People, this sometimes means getting the cash collectively for a down cost on a home. Nonetheless, there are increasingly more choices that mean you can faucet into this asset class with out the trials and tribulations of managing a mortgage or turning into a landlord. For instance, you possibly can entry the rental property market by investing in shares of trip houses or rental properties by way of Arrived. Backed by world-class buyers, together with Jeff Bezos, Arrived permits you to spend money on shares of trip and rental properties, probably incomes a passive revenue stream with out having to handle sensitive tenants and midnight upkeep calls. To get began, merely flick through their number of vetted properties, every hand-picked for his or her potential for appreciation and revenue era. When you select a property, you can begin investing with as little as $100, probably incomes quarterly dividends. Be part of 200,000+ readers and get Moneywise’s greatest tales and unique interviews first — clear insights curated and delivered weekly. Subscribe now. We rely solely on vetted sources and credible third-party reporting. For particulars, see our editorial ethics and pointers. Enterprise Insider (1); Membership Shay Shay(2); Selection(3); Chamber of Commerce (4); BizBuySell (5) This text gives data solely and shouldn’t be construed as recommendation. It’s offered with out guarantee of any sort.
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Dave Portnoy offered Barstool Sports activities for $551M — then bought it again for $1 — what to study from this ‘great trade’
