Dave Portnoy's Pivot to Stocks from Sports

(Bloomberg Opinion) -- It only took Dave Portnoy 17 years to become an overnight sensation. The web entrepreneur, pizza reviewer and day trader – and founder of Barstool Sports – began as a “one man band,” doing everything himself. As this week's guest on Masters in Business, Portnoy wrote copy, sold ads and headed twice a day to Boston's financial district to hand out the four-page “fanzine” in person starting in 2003. Earlier this year, publicly traded Penn National Gaming Inc. took a 36% stake in Barstool Sports, valuing the company at $450 million.

After selling a 51% stake to private equity firm The Chernin Group LLC in 2016, Portnoy relocated Barstool Sports to New York. The company added new writers, podcasts and videos. It is known for not only sports betting but for pop culture content, including Portnoy's attempt to review every pizza place in New York City (“One Bite With Davey Pageviews).” Once live sporting events and gambling were cancelled due to the pandemic, Portnoy pivoted, becoming “Davey Day Trader,” inspiring an “an army of 1.8 million Twitter day traders” who track his every trade.

A transcript of our conversation is available here.

You can stream and download our full conversation, including the podcast extras on iTunes, Spotify, Overcast, Google, Bloomberg, Stitcher and Acast. All of our earlier podcasts on your favorite pod hosts can be found here.

Be sure to check out our Masters in Business next week with Joel Greenblatt, whose Gotham Capital presided over an annualized return of 50% for a decade. His firm Gotham Asset Management manages a variety of funds that have beaten market indexes. He is an adjunct professor at Columbia Business School on value and special situation investing. His latest book is Common Sense: The Investor's Guide to Equality, Opportunity, and Growth.

This column does not necessarily reflect the opinion of the editorial board or Bloomberg LP and its owners.

Barry Ritholtz is a Bloomberg Opinion columnist. He is chairman and chief investment officer of Ritholtz Wealth Management, and was previously chief market strategist at Maxim Group. He is the author of “Bailout Nation.”

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