My guest today is NBA Hall of Famer and author, Chris Bosh. Chris fell in love with basketball at an early age and earned the prestigious “Mr. Basketball” title while in high school. After getting dra

My guest today is fashion designer, Sir Paul Smith. Paul’s fashion company was founded back in 1970 and has expanded into 70 countries since. He was made a Royal Designer for Industry in 1991. More recently he released “Paul Smith”,

My returning guest today is the CEO and founder of SERHANT, Ryan Serhant. Ryan first appeared on the second episode of 5 Questions a few years ago and now he’s back after having started his new real estate company SERHANT and authoring a new book calle...

My guest today is NYU Stern Professor, author, and serial entrepreneur, Scott Galloway. Scott founded nine companies, including Prophet, Red Envelope, and L2. He is the bestselling author of The Four and The Algebra of Happiness and has served on the b...

My guest today is host of Ridiculousness, professional skateboarder, and serial entrepreneur, Rob Dyrdek. Rob began skateboarding at age 11 and just a few years later he turned pro while landing his first board sponsor.

My guest today is Emmy Award-winning actress and voice of Lisa Simpson, Yeardley Smith. Yeardley has been the voice of Lisa Simpson on The Simpsons for 32 seasons since 1987. She’s appeared in movies including As Good As it Gets, City Slickers,

My guest today is CNN host and author, Jake Tapper. Jake started his career as a Campaign Press Secretary before transitioning to journalism and is now the host of Take the Lead with Jake Tapper on CNN. Aside from hosting a weekly TV show,

My guest today is *NSYNC member and host of Common Knowledge on the Game Show Network, Joey Fatone. Joey is best known for being a member of the multi-platinum selling music group *NSYNC and for his appearances on multiple TV shows and movies like Danc...

My guest today is actress, podcaster and entrepreneur, Sophia Bush. You may know Sophia as a co-star of One Tree Hill alongside past 5 Questions guest Hilarie Burton, but she’s also starred in movies like John Tucker Must Die and Incredibles 2.

My guest today is writer and author, Malcolm Gladwell. Throughout his career, Malcolm has written six popular books including Talking to Strangers, David and Goliath, Outliers, Blink, and The Tipping Point.