MiB: Pivoting During Lockdown

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: He wrote copy, sold ads, distributed the paper, heading twice a day to the Boston financial district to hand out the 4-page fanzine in person. Earlier this year, publicly traded Penn National Gaming took a 36% stake in Barstool Sports in cash and stock, valuing the company at $450 million.

Barstool Sports began life in 2003 as print edition, handed out at the Boston Garden and Fenway Park. In 2016, after selling a 51% stake to private equity firm The Chernin Group, he relocated the firm to NYC. The company expanded, adding 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 NYC (“One Bite With Davey Pageviews).” Pre-lockdown, he became a known on the streets of NYC, inviting celebrities and strangers on the street to join his reviews.

Once live sporting events and gambling got cancelled during the pandemic, Portnoy again pivoted, becoming “Davey Day Trader,” inspiring 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 iTunesSpotifyOvercastGoogleBloombergStitcher 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 indices . 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.


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