Every-Bro David Portnoy’s Hapless Tale of Crypto Foolery


Who hasn’t wondered about cryptocurrency? What is it? How does it work? The questions are typical and pervasive. If you are one of the few who has informed themselves and obtained crypto knowledge, friends and family members might treat you like a guru or magic human who has somehow beaten finance’s final boss.

In 2017, Every-bro David Portnoy was tired of the crypto questions being lobbed at his mind with nothing there to hit them. Portnoy was running a successful website at the time, Barstool Sports, and in 2020 he would become wealthy by selling it. The sale apparently got him $163 million in cash and stock. Dude knows how to make money…in some ways but not in crypto. Three years before the sale he was feeling left out of that bitcoin thing he kept hearing about. His frustration was the beginning of his crypto journey. He had a decent online following so he made a video asking what crypto is, in the hope of ending his confusion and becoming part of this club that sounded so awesome. In January, he took a small break from cheering for bad sports teams and doing pizza reviews to make a video and give everyone an update. He called it, “I Keep Getting Face Fucked By Bitcoin”. The video perfectly encapsulates how frustrating investing can be in general and crypto in particular. 

Portnoy Meets the Winklevoss Twins

He begins by providing context. When he made his 2017 video, it just so happened that the ultimate outside-looking-in-bros the Winklevoss Twins were in the Hamptons at the same time as him. The Twins know bitcoin. As Portnoy says, “They own like 10% of Bitcoin or something crazy. I dunno. They own bitcoin…or something.” They saw the video and ended up coming over in shorts and matching scarves to tell him everything. After their talk, Portnoy decides to buy Bitcoin. He buys $500,000 of it at $11,000 on the Winklevoss platform Gemini, but he is bothered by his interaction with twins, deciding they are “cookoo,” he pulls his money out.  Shortly after bitcoin goes to all-time highs hitting over $60,000 and once again Portnoy is on the outside looking in.

He continues to break down his journey. None of it is winning. He loses $50,000 on another crypto offering and then decides to commit to Bitcoin and educate himself, buying over a million at $32,000 with a diamond hands approach. Then FTX crashes because of “that loony tune fuck” and takes the market down with them.  He hears rumblings that Gemini will be next so he goes into his account to make sure it is still working.  Without realizing it, he turns all of his Bitcoin into cash, leaving him a little over $400,000. This mistake goes unnoticed until Bitcoin goes up over $42,000 and he goes to check his account where he doesn’t see earnings but a significant loss. 

He ends by asking, “What am I supposed to do now, buy it at 44? I bought it at 32. I fucking cashed out at 20 by accident”. There hasn’t been a new update but hopefully, he did because Bitcoin has gone on to a new all-time high since, almost reaching $74,000. But it seems unlikely. Some might say he doesn’t have the right psychology to be trading, he gets too distracted and can’t focus on the fundamentals to the point where he turns all of his holdings into cash without realizing it. Or maybe, he just has bad juju when it comes to crypto and the best thing he can do is recognize it and accept that some things just aren’t for him. His journey began with the frustration of not understanding and being on the outside and it has only compounded frustrations as he’s tried to get in on the game. For many people, the market represents freedom and possibility but in Portnoy’s case, it looks like it represents fate. Sometimes, effort and belief are not rewarded or they are not enough to overcome fate and Portnoy seems to be fated to frustration, to always be looking in, to being close but not close enough. Who hasn’t been there? In that sense, Portnoy really is every bro.

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