Dave Portnoy Trades And Entertains, But Whitney Tilson Says He's Reminiscent Of The 'Proverbial Shoeshine Boy'

Dave Portnoy, the founder of the hugely popular sports and pop culture website Barstool Sports, has turned his attention to the stock market since the cancellation of major sporting events. Portnoy has had success up to this point with his somewhat tongue-in-cheek daily “Davey Day Trader Global” stock trading streams.

But Whitney Tilson said this week that Portnoy’s exploits remind him of the 1999 dot-com bubble and of a story JFK’s father Joe Kennedy once told about a shoeshine boy.

Shoeshine Boy Picking Stocks: Kennedy famously told the story of getting his shoes shined one day back in 1929 when the boy shining his shoes began to give him tips on which stocks to buy. Kennedy then knew it was time to exit the market ahead of the stock market crash.

Portnoy has recently been trolling legendary Wall Street icon Warren Buffett, who sold airline stocks near the market bottom.

Portnoy has made a killing off of buying the airline stocks, which first got Tilson’s attention.

“I'm sure a lot – if not all – of this is satire in the service of personal promotion. But I have no doubt Portnoy is actually making these trades (and these are clearly trades, not investments),” Tilson wrote in his email newsletter.

“When I saw that clip of Portnoy claiming superiority over Buffett, I first thought of Pets.com – the online retailer famous for its sock puppet mascot.”

Pets.com famously went bankrupt just nine months after its incredibly hyped IPO when the dot-com bubble burst.

“When the proverbial shoeshine boy gives you stock tips, it's time to watch out…” Tilson said.

Tilson is particularly skeptical of cruise line operators Carnival Corp CCL, Norwegian Cruise Line Holdings Ltd NCLH and Royal Caribbean Cruises Ltd RCL. He also said airline stocks, which have been among Portnoy’s top picks, are very high-risk trades.

Tilson founded and managed Kase Capital from 1999-2017. The fund closed after underperforming the market for years. He launched Empire Financial Research, an investment newsletter business, in 2019.

Regardless of his profit margins, Portnoy’s venture into Wall Street has been an excellent promotion for Barstool Sports during the sports shutdown.

“I’m not a financial advisor. Don’t trust anything I say about stocks,” Portnoy recently tweeted.

Benzinga’s Take: It seems Tilson recognizes to some extent that Portnoy’s streams and market commentary blur the lines between satire and reality. However, the potential danger lies with his followers who don’t fully understand the complexity of the market and the fact that high-beta stocks will often outperform a bull market but will be among the worst performers if and when the tide eventually turns bearish.

Do you agree with this take? Email feedback@benzinga.com with your thoughts.

Related Links:

Bartstool's Dave Portnoy Breaks Down About The Importance Of Diversification

Trump To Buffett: 'Should Have Kept The Airline Stocks'