Dave Portnoy of Barstool Sports pulls up to the This Past Weekend podcast with Theo Von in episode #429. For those who may not know, Portnoy is basically an internet celebrity. The company he founded, Barstool Sports, is a blog covering sports and pop culture.
The episode kicks off and, early on, dives into Dave Portnoy’s upbringing. He is Jewish. Theo Von wanted to know what influence that had on him becoming successful. That’s because many of Von’s Jewish friends are successful and work in media. Portnoy explains that his parents never pressured him to become successful. They wanted him to do well in academics and were sorta overprotective. They would have been happy seeing Portnoy live out his initial dream of becoming a gym teacher. He became vice president in high school to bulk up his resume. He chose not to go for president because that’d be too much work. Dave Portnoy played sports and got by on being funny rather than his looks. This prompts Theo Von to recall his younger days.
“I’ve always been like an 8,” Von says. “An 8? Out of a 10?” Portnoy says, shocked. “That’s like a super high score.” You can tell Portnoy thinks Von is overshooting, but he lets him slide.
Next, Theo Von asks Portnoy if he had a lady in high school. Dave responds that he had little if any, success. He credits a chunky stage as part of the influence. I can relate because I, too, went through a chunky period when I was younger. In fact, I was pretty bad with the ladies myself, lol. I remember one time growing up. My friend and I went to this place called Robinwood Lake. It was a wild place. It was like a swimming hole, except the owners built this insane 3 story diving platform out of metal and concrete. Honestly, I have no clue how this place was ever open. But anyway, you would climb up a ladder and jump off the top platform roughly 30 feet into the water.
Since I was chunky, I was self-conscious and insecure. To make it worse, I had a case of the bologna nipples/man boob combo. One of the worse combos a lad fears when it comes to his body at a young age. My friend knew this. So to cheer me up, he asked two girls a dreaded question as we stood atop the platform, waiting to jump. All I could think about were my man titties flapping in the wind as I fell through the air on my way down into the water. Just before my turn, my friend asked the two girls, “Hey, do you think he is fat?” My heart sank. The moment had come. I was exposed. All my fears and insecurities at that moment were on the table, so to speak. She looks over at me. Her eyes lock with mine. Then she looks down. Then back up again. And says, “well, he ain’t skinny.” I felt a piece of me inside perish. I was blown away. My friend obviously thought she would be a decent human being and not say something rude. But that? That was next level. I turned and jumped off the platform as fast as I could. I thought about how much of a b-word that girl was with every foot I descended. And they watched my cosmic brownie-filled body rage in the wind until a glorious splash snapped them out of a trance. Over 15 years later, he still brings it up. Still feels bad. Me? I feel better. Because honestly? If you don’t like cosmic brownies, you’re suspect.
Picking up with This Past Weekend #429, Theo Von asks Dave Portnoy if he remembers his first kiss. The answer? No. However, Theo remembers. And, of course, it’s a hilarious story from left field. Check out the funny video and share the laughs with someone!