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The Pomp Podcast

Dave Portnoy GOES OFF On Bitcoin, AI, Socialism & Being Fired From Barstool

The Pomp Podcast

Anthony Pompliano

Investing, Business

4.62K Ratings

🗓️ 30 June 2026

⏱️ 58 minutes

🧾️ Download transcript

Summary

Dave Portnoy is the founder of Barstool Sports and author of Cancel Me If You Can. In this conversation, we break down how ESPN tried to force him out of his own company and how he engineered the legendary $1 buyback, his days as "Davey Day Trader" during Covid and the GameStop saga, his history with Bitcoin and crypto, and why he's considering running for mayor of New York City.

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  • 0:00 - Intro
  • 0:52 - How ESPN tried to fire Dave from his own company & the $1 buyback
  • 12:47 - How Pomp and Dave first met & the Barstool Finance deal
  • 14:55 - Davey Day Trader, Covid, & going to war with Wall Street
  • 18:33 - GameStop & Steve Cohen
  • 23:30 - Barstool's content model & talent machine
  • 29:45 - The Business Insider hit piece
  • 34:05 - Running for mayor of New York City
  • 37:36 - How many houses does Dave have?
  • 39:26 - AI and the future of content
  • 41:51 - His ex-wife & the bank account story
  • 44:12 - Bitcoin — bad trades, losses, & where he stands now
  • 47:32 - Crazy Barstool moments
  • 54:35 - The new book "Cancel Me If You Can"

Transcript

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0:00.0

This episode is brought to you by Coca-Cola Zero, official partner of the FIFA World Cup 2026.

0:06.9

Coca-Cola has also partnered with Panini to bring fans closer to the tournament.

0:11.7

Selected Coca-Cola bottles will feature exclusive Panini FIFA World Cup 2026 stickers under labels.

0:19.2

Collect 12 exclusive stickers for the dedicated Coca-Cola double-page spread.

0:24.1

Pick up a Coca-Cola zero sugar and start collecting.

0:27.8

Peel, sip, collect.

0:30.6

When the world keeps shifting, we're there to help you act with confidence.

0:35.8

At HSBC, we bring together the people, ideas, and capital that drive growth,

0:40.9

backing your ambitions at every stage.

0:43.4

So when you're preparing for the next generation,

0:45.9

strengthening your portfolio, or you're entering new markets,

0:49.2

we're there, bringing 160 years of experience to help you move forward.

0:54.5

HSBC, opening up a world of opportunity.

0:59.9

I walked out of that meeting, called Renee, my ex.

1:02.8

I go, I just got fired from Barcelona.

1:04.8

I couldn't believe it.

1:05.6

And we're changing.

1:06.3

It's changing from Barcel's Sportsbook to ESPN bet.

1:09.8

And they did this gigantic deal. I think it was 10 years, two billion is what this deal ended up being. And ESPN would market everything. I talked to Erica. I talked to Dan. And we all kind of regrouped. What do we want to do here? All right, guys, today we got a conversation with Dave Portnoy. He's founder of Barstool Sports. and he wrote a great book, Cancel me if you can. It is absolutely hilarious. In this conversation, we talk about how we almost got fired from Barstool, or he did get fired. We talk about his investments, how much money he's got, how much money he spends on a monthly basis. Talk about AI, what stocks he likes, what stocks he doesn't like Bitcoin. Is he a fan? Is he not? How much does he hold? There's incredible amount of detail in here. And he does it all in his own style. He just tells you the truth. It's pretty entertaining. Enjoy. Here's my conversation with Dave. All right, Dave, you got a new book out. Everyone is worried about all these little anecdotes. But the craziest story to me is that Penn, the company that had bought Barstool, fired you from Barstool Sports. How's that happened? Yeah, so I thought that would be the number one story in the book. It hasn't been so far, but essentially what happened, and I tell this story, we're in New York, and I had a great relationship with Jay Snowden. Like, we were... The CEO of Penn. Yep,-Pen. Like, we were lockstep. I trusted him totally. He trusted me. We hadn't met in a bit. Is I going to be in New York City? Can you meet me for lunch? Of course, sure. And hand to God, walking into the restaurant. It's a little Italian place empty. I go, this looks like where somebody would get whacked, like in a mob movie. I literally said it.

2:37.5

To him.

3:07.6

To him. To him. As we're walking, we sat in the back table in the corner, nobody around. And he starts telling me updates, like updates in the business. He's like, we are doing a huge deal with ESPN, which is shocking to me, but great. I didn't know in my head. I'm like, all right, so is ESPN going to promote Barstall's sportsbook? Are we like, what's going on? Because you guys were kind of competitive a little bit in terms of you had a sports book and ESPN wanted to have a sports book and now the company was going to essentially do a deal. Yeah, ESPN was basically a hired gun at that point. Like they could advertise that they may have been advertising Draft Kings, Fandul,

3:11.6

whoever. They didn't have a specific company that they're advertising with. We were branded. So when

...

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