President Trump sat down with daytrader Dave Portnoy on Thursday after the White House reached out for an interview.
The two covered a broad range of topics, from sports figures kneeling in support of Black Lives Matter, to Trump's tweeting habits - which the President admitted occasional regrets over.
"It used to be, in the old days, you'd write a letter, and you'd say, 'This letter's really big.' You'd put it on your desk, and then you go back tomorrow and you say, 'Oh, I'm glad I didn't send it.' Right? But we don't do that with Twitter. Right? We put it out instantaneously, we feel great, and then you start getting phone calls: 'Did you really say this?'" -President Trump
The two then discussed Trump's decision to leave his cushy life in the private sector and enter politics - driving many on the left to abandon support for the billionaire.
"You're the most famous person in the world. My guess is nobody ever said 'Hey, I don't like Donald Trump' before he became president. Now everyone has an opinion, and your life has changed forever when - seemingly, you had the dream life beforehand," said Portnoy.
To which Trump replied: "I was in so many rap songs, like 79. This is before I did this," adding "The best day in my life in terms of business and life and everything was the day before I announced I'm running for president."