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 drafted by the Toronto Raptors, he went on to become a five-time NBA All-Star before joining the Miami Heat and […]

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”, a monograph book that captures his unique spirit and creativity, which we discuss in this […]

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 called Big Money Energy”. I ask Ryan about the inspiration […]

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 boards of directors of the New York Times Company and Urban Outfitters. We discuss […]

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. He’s best known for hosting hit TV shows including Rob & Big, Ridiculousness, and Rob Dyrdek’s Fantasy Factory. Rob founded […]

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, and TV shows like The Big Bang Theory and Mad Men. Yeardley co-founded […]

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, he’s authored several books, including his latest novel “The Devil May […]

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. She’s been a long-time environmentalist, especially now as the co-founder of Fashionkind, a […]

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. He was a Staff Writer at The New Yorker for many years and is now the host of the Revisionist History podcast. We learn […]

My guest today is actor and author, Justin Baldoni. While you may know him from acting in Jane the Virgin or his films Five Feet Apart and Clouds, Justin has spent his life on a journey to understand what it means to be a man. After giving a TED Talk about being “man enough”, he […]

My guest today is the anchor of CNN Tonight, Don Lemon. Over the course of his longtime media career, Don went from anchoring local news stations to being an NBC News correspondent to hosting CNN Tonight weeknights at 10 PM eastern time. As America’s only African American prime-time anchor, who is openly gay, he has […]

My guest today is former CNN anchor and author, Brooke Baldwin. Brooke is a veteran journalist and Peabody Award finalist, who covered both the Obama and Trump administrations and reported on global news stories. She created and hosted CNN’s digital series American Woman, which promoted trailblazing women in politics and culture. This year she left […]

My guest today is the co-founder and CEO of Airbnb, Brian Chesky. Brian is the epidemy of rags-to-riches having gone from not afford rent with his co-founder to founding the multibillion-dollar hospitality company Airbnb. Through his leadership, the company is used by more than 500 million customers in 191 countries. Despite being one of the […]

My guest today is the founder and CEO of Thrive Global, Arianna Huffington. Throughout the past decades, Arianna has become a prominent voice focused on media, politics, and well-being as the founder of both The Huffington Post and Thrive Global. She’s written 15 books, most recently Thrive, The Sleep Revolution, and Your Time to Thrive, […]

My guest today is actor, producer, comedian, and Founder of Crystal Head Vodka, Dan Aykroyd. Even though Dan intended on becoming a priest, he dropped out of college and worked as a comedian in Canadian nightclubs. He rose to fame as a cast member for Saturday Night Live and eventually starred in hit movies like […]