How Did Dave Portnoy Get Donald Trump to Admit a Mistake?

TL;DR

Dave Portnoy got Donald Trump to admit that he sometimes regretted his tweets by asking whether he ever woke up wishing he had not posted something. Portnoy says a remark involving his father first disarmed Trump and changed his demeanor. He also explains the interview’s less-than-24-hour notice, last-minute restrictions, and unusual setting. Read on for the full story behind the exchange.

Transcript

i i actually got him to admit he made a mistake with tweeting do you ever just wake up the next day be like man i wish he's like yeah i do what's up everybody welcome to flagrant and today we have the man the myth the legend bar stools own dave porter hey everybody thanks so much matt i have uh i have a bone to pick with you dave because you did th... Read More

Key Insights

• 👨 Dave Portnoy's interview with Donald Trump was a memorable moment where he disarmed Trump by bringing up a personal story about his father.
• ❓ Portnoy navigated controversies and backlash by remaining true to his brand and defending the authenticity of Barstool.
• 🌥️ The success of regional tours and events like Stoolapalooza and the Blackout tour helped Barstool gain a larger fan base and attract advertisers.
• 🌍 Portnoy emphasizes the importance of being quick and nimble in the ever-changing world of media and content creation.

Questions & Answers

Q: How did Dave Portnoy get Donald Trump to admit he made a mistake?

Portnoy asked Trump whether he ever woke up the next day wishing he had not posted something on Twitter. Trump answered that he did, which Portnoy viewed as an admission that some of his tweeting had been a mistake.

Q: How did Dave Portnoy disarm Donald Trump during their interview?

Portnoy brought up a story involving his father, who disliked Trump. He says the exchange made Trump view the conversation as friendly, changed his demeanor, and prompted him to explain himself.

Q: What unexpected question did Dave Portnoy ask Donald Trump?

After the friendly opening, Portnoy asked Trump why people could not take a knee. The hosts described it as a strikingly abrupt follow-up to the complimentary exchange.

Q: How much notice did Dave Portnoy have before interviewing Donald Trump?

Portnoy says he learned about the interview less than 24 hours beforehand while he was on vacation. A member of his team told him that Trump wanted him to conduct the interview in the Rose Garden.

Q: Was Donald Trump Dave Portnoy’s first interview?

Portnoy says this was the first time he had ever interviewed anyone. He also says Trump did not really know who he was, although Donald Trump Jr. and other people around Trump were Barstool fans.

Q: Was Dave Portnoy allowed to ask Donald Trump anything?

Portnoy’s team was initially told repeatedly that he could ask anything. Immediately before the interview, however, Trump’s staff surrounded them and listed subjects he should not ask about; Portnoy says he ignored the warning and got most of his questions out.

Q: Why did Dave Portnoy try to keep Barstool out of politics?

Portnoy says political coverage risks angering part of the audience. He framed Barstool’s goal as making money rather than taking a political side and acknowledged that supporters and critics of Trump judged the interview differently.

Q: Why did Dave Portnoy start creating TikTok content?

Portnoy says Barstool had existed for 20 years, but people on TikTok did not know the brand. Although he disliked having another social platform to manage, he saw it as something Barstool needed to address to stay relevant.

Summary & Key Takeaways

• Dave Portnoy shares his experience interviewing Donald Trump and how he disarmed him by bringing up a personal story about his father.

• He talks about the wild questions he asked Trump, including why people can't take a knee.

• Portnoy discusses his early days at Barstool, including the success of the Barstool Blackout tour and the challenges of expanding the brand.