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 business incubator Dyrdek Machine and hosts the “Build With Rob” podcast. We talk about his journey from being a skateboarder to building his businesses in this podcast episode. The 5 questions I ask in this episode: In your early 20s, you gained fame as a professional skateboarder and were able to travel the world. Despite your newfound success, why wasn’t skateboarding giving you the purpose and fulfillment you were seeking? You’re part skater, part TV personality, and part entrepreneur. How were you able to turn your success as a skater into a series of TV shows and into multiple businesses and partnerships? You’ve brought your family and friends with you much as we saw in HBO’s Entourage series. How has involving your best friend and cousins in your projects deepened your relationship with them and what have you taught them that has improved their careers?With so many businesses and projects happening simultaneously, how do you manage your time and decide what projects to invest or divest in? What’s your best piece of career advice? Video interview Follow Rob’s journey: Website PodcastFacebookTwitterInstagram

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 the Paperclip Production company and co-costs and co-produces the Small Town Dicks podcast. We talk about her life growing up and her experience in Hollywood during this podcast episode. The 5 questions I ask in this episode: How did coming from a family who worked in the arts inspire you to become an actress and what keeps you motivated to develop new projects? You were teased for your “unusual voice” in your childhood yet that voice is now part of TV history and has amounted to wealth and fame. How did you handle this teasing during childhood and start to appreciate your unique voice as you aged?How are you like Lisa Simpson and why do you think she has resonated with people for the past 30 years? An analysis of 2,000 movies by Polygraph found that women get less dialogue in Hollywood films the older they get. In your experience why do you believe older women are still underrepresented and what can we do to change that? What’s your best piece of career advice? Video interview Follow Yeardley’s journey: Podcast YouTubeTwitterInstagram

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 Dance”. We discuss everything from the book to his time management strategies and early career in this podcast episode. The 5 questions I ask in this episode: What experience did you gain as a press secretary early in your career that helped you transition to becoming a successful journalist?How do you manage your time between covering politics on CNN and writing fiction books?In what ways does The Hellfire Club and The Devil May Dance reflect our current political system, the media world, and the issues we face as a society? What was the process of turning factual events from the 1960s into setting or plot points for a fiction book? What’s your best piece of career advice? Video interview Follow Jake’s journey: Books FacebookTwitterInstagram

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 Dancing with the Stars and My Big Fat Greek Wedding. Today, he’s the host of Common Knowledge on the Game Show Network that has its Season 3 premiere this evening. We discuss his career influences and life lessons during this podcast episode. The 5 questions I ask in this episode: How did your father influence you to become a singer and entertainer growing up and what advice did he offer you? *NSYNC creator Lou Pearlman was convicted of fraud over a decade ago. What lessons did you learn from working with him that have shaped how you manage your career today? Your show is called “Common Knowledge”, but a lot of common knowledge is not common and that’s what makes the show educational and entertaining. What is one piece of common knowledge that you expect your fans to know about your career and one piece of uncommon knowledge? How has being in a music group, and appearing in TV shows and movies, prepare you to host your own show? What is your best piece of career advice? Video interview Follow Joey’s journey: TV show TwitterFacebookInstagram

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 sustainable luxury fashion company. We talk about both her acting and entrepreneurial career during this podcast episode. The 5 questions I ask in this episode: Even though you wanted to play for your school’s volleyball team, you were required to do theatre. How did your experience on stage make you realize that you were meant to be an actress? You co-founded the luxury fashion company Fashionkind. When did you originally connect with your co-founder Nina Farran and how do you both complement each other? As an accomplished actress and co-founder of FashionKind. What skills and experience have you applied from your acting career to your business and vice versa? More than ever before, people want to work for, or spend money with, companies that address societal needs. The fashion industry uses 1.5 trillion liters of water a year and the apparel industry accounts for 10% of global carbon emissions. Why did you originally become an environmental justice advocate and how does FashionKind address these issues? What’s your best piece of career advice? Video interview Follow Sophia’s journey: Company PodcastTwitterFacebookInstagram

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 more about Malcolm as he explores the themes from his new book, The Bomber Mafia, in this podcast episode. The 5 questions I ask in this episode: Even though you never set out to be a writer, what life experiences made you pursue this career path? Why were you so captivated by the story of The Bomber Mafia and how do you decide what topics and stories to tell? Back in 2013, when I interviewed you for your book David and Goliath you said “you learn more from difficult times than from good times”. How was The Bomber Mafia’s failure a lasting contribution to society even though it led to mass death? One of the themes you explore in the book is the collision between morality and technology. How can we promote more humane projects while preventing unethical ones from harming us? What is your best piece of career advice? Video interview Follow Malcolm’s journey: Website BookPodcastTwitterFacebookInstagram

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 wrote a book by that name, which we discuss in-depth during this podcast episode. The 5 questions I ask in this episode: Growing up, your father defined being a man as providing for your family instead of being tough and strong. How is your view of masculinity similar to his and what you have done to make it your own? Over the past several years, gender roles have changed substantially from when our parents grew up with female breadwinners and stay-at-home fathers. What is your hope for how male and female relationships will evolve in the future and how masculinity and femininity will be redefined? How have you been raising a compassionate feminist son and what role has your daughter played in his growth as a human? What are some ways that men can start having more deep and vulnerable conversations instead of staying surface-level talking about things like sports? What is your best piece of career advice? Video interview Follow Justin’s journey: BookTwitterFacebookInstagram

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 covered racism, the failure of government, and the global pandemic over the past year. After examining the deep roots of racism in America, he wrote “This is The Fire”, which we explore in this podcast episode. The 5 questions I ask in this episode: During your childhood, how did you decide you wanted to be a news anchor and what obstacles did you encounter as you ascended the media hierarchy from local to prime-time TV? You are a public figure representing both the gay and African American minority communities. What do you believe your role and responsibility is to support both groups on and off the air? Your experience combating and covering racism is covered in your book This Is The Fire. How do you think we can start to end racism in America despite its deep-rooted history? How have you been able to handle the mental and emotional toll from covering deeply personal topics like racism and who do you rely on for support? What’s your best piece of career advice? Video interview Follow Don’s journey: BookTwitterFacebookInstagram

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 CNN to focus on her new book “Huddle”, which encourages women to lean on one another, which we discuss in this podcast episode. The 5 questions I ask in this episode: Who in your life is most responsible for making you the woman you are today and why? What were some of your struggles growing up in the south while trying to make it in a male-dominated industry and how did you overcome them? In your book, you discuss this concept of “huddling” as a way to bring women closer together. Can you give an example of when you huddled with one or more women in your career and how you supported each other? We are in a “shecession” right now with a few million women dropping out of the workforce in the past year during Covid, reversing women’s workplace gains, mostly due to childcare. What can we do to help women recover from economic setbacks? What is your best piece of career advice? Video interview Follow Brooke’s journey: BookTwitterFacebookInstagram

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 biggest success stories in his entire generation, Brian is down-to-earth and shared some valuable insights from his life during this podcast episode. The 5 questions I ask in this episode: Both of your parents were social workers. What values did they instill in you that has made you the leader you are today? The hospitality industry was one of the biggest victims of the pandemic. You and Airbnb reacted to Covid by creating online experiences, offering a $250 million support package to hosts, and more. But, can you talk about how you managed the mental and emotional hardship of navigating the crisis while overseeing thousands of employees, and millions of hosts and customers worldwide? Airbnb has come a long way since you co-founded it back in 2008. I recently stayed at an Airbnb in Miami, but if I said that to my parents a decade ago, they would have reacted stating “what’s that?” or “just stay at a hotel it’s safer”. What do you think originally led to the acceptance of Airbnb and how has its growth affected how you live and relate to other people in your life? In my last book, Back to Human, which was published just before Covid, I tell people to “use technology as a bridge to human connection instead of letting it be a barrier that isolates them from others.” In the foreword for Airbnb’s “Travel Report,” you emphasize this by saying that “technology has provided a means of digital connection, but this is more synthetic and less fulfilling than real human connection”. I think only robots would disagree with our perspectives. How have you used technology as a bridge to real human connection with your family, friends, and team? What is your best piece of career advice? Video interview Follow Brian’s journey: CompanyTwitterFacebookInstagramLinkedIn