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 […]

My guest today is former NASA astronaut Scott Kelly. Scott is best known for spending a record-breaking year in space. He is a former US Navy fighter pilot, test pilot, and veteran of four spaceflights. After retiring in 2016, Scott has written a series of books including his latest one for children called “Goodnight, Astronaut”. […]

My guest today is co-host of The Talk on CBS, Sharon Osbourne. Throughout Sharon’s remarkable life, she was raised by a violent and manipulative father, married a rock star and helped launch his career, starred in a reality TV show with her family, and survived cancer. We discuss how she’s persevered despite her many life […]