My guest today is Shark Tank and Money Court star, Kevin O’Leary. Kevin has been an investor on ABC’s Shark Tank for 12 seasons and is the host of the new CNBC show Money Court. He made his fortune by founding SoftKey Software Products, which he sold to Mattel. Kevin is the Chairman of O’Shares Investment Advisers and Beanstox. We talk about his new show, and investing advice, during this podcast episode. The 5 questions I ask in this episode: What financial advice did you receive from your mother growing up that’s influenced your investment decisions today? Why is having a money dispute the worst thing that can happen in a business and what’s the first step to solving it? What lessons have you learned as a Shark Tank investor that have helped you solve disputes between business owners? You have a variety of hobbies like collecting watches, photography, wine, and guitar. How do you find the time to indulge in these hobbies, while being on multiple TV shows, advising startups, and running your fund? What is your best piece of career advice? Video interview Follow Kevin’s journey: Website InstagramFacebookYouTubeTwitter

My guest today is actor, TV host, former NFL football player and author, Terry Crews. Terry played as a defensive end and linebacker for the Los Angeles Rams, San Diego Chargers, and Washington Redskins. After retiring in 1997, he starred in films including White Chicks, The Longest Yard, and The Expendables. Currently, he’s starring in the final season of Brooklyn Nine-Nine and hosting America’s Got Talent. We talk about how he reinvented himself, from feeling like a victim to being accountable for his life, during this podcast episode. The 5 questions I ask in this episode: What was the process of reinventing yourself from being an NFL football player to an actor and how are those careers related? When did you make the shift from leading a life that you thought your parents expected from you to the one you always wanted? You’ve openly talked about the mistakes you’ve made as a parent and husband. What did it take for you to confront these mistakes and make amends with your family? In your books, you talk about money, relationships, and religion. How are these areas in your life interconnected? What is your best piece of career advice? Video interview Follow Terry’s journey: Website BookInstagramFacebookTwitter

My guest today is actress and author Mena Suvari. Mena is best known for her iconic acting roles in American Beauty and American Pie. Even though these roles made her famous, she was also dealing with abusive relationships and drugs, which she writes about in her memoir “The Great Peace”. We discuss Mena’s double life, how she’s overcome trauma, and the lessons she’s learned in this podcast episode. The 5 questions I ask in this episode: With the breakout releases of American Beauty and American Pie, you were living a double life being a Hollywood star, while dealing with an abusive relationship at home. How did you manage those two different realities? In your memoir, you talk about an accident you had while horseback riding. How did that moment lead you down this road of facing your trauma and accepting yourself? Your book is called “The Great Peace”. What does it mean to you to make peace with everything you’ve been through over multiple decades? With a history of toxic relationships, how have you made your marriage work and what values will you instill in your child? What’s your best piece of career advice? Video interview Follow Mena’s journey: BookInstagram

My guest today is actress, neuroscientist and author, Mayim Bialik. Mayim is best known as the star of the sitcom Blossom and The Big Bang Theory. She won the Critics Choice Television Award for Best Supporting Actress in a Comedy Series in 2015 and 2017. More recently, she’s the host of the Mayim Bialik’s Breakdown podcast and star of “Call Me Kat”. We talk about these projects, her childhood, and her career in this podcast episode. The 5 questions I ask in this episode: What qualities did you have at age 11 that indicated to your parents that you could be an actress and how did they support you? In college, you majored in neuroscience and minored in Hebrew and Jewish studies. How have you incorporated your education into your acting roles, projects, and non-profit ventures? In your podcast, you use your Ph.D. in Neuroscience, personal experience, and special guests to break down mental health. What have been some of your own mental health struggles and how has the show helped you better cope with them? What can we learn from the character you play in your show “Call Me Kat” about being happy despite having many life struggles? What is your best piece of career advice? Video interview Follow Mayim’s journey: PodcastFacebookTwitterYouTubeInstagram

My guest today is Grammy Award-winning DJ and producer, Mark Ronson. Mark was born in London and raised in New York City, where he became known as a DJ. He has collaborated with artists including Amy Winehouse, Bruno Mars, Lady Gaga, and Miley Cyrus. Mark produced “Uptown Funk” with Bruno Mars that spent 14 weeks at number one on the Billboard Hot 100 list. Currently, he’s the host of “The FADER Uncovered Podcast”. We talk about his early childhood, collaborations, and creativity during this podcast episode. The 5 questions I ask in this episode: How did your parents encourage you to get into music in your childhood and then support you as you build your career? You’ve collaborated with well-known artists including Bruno Mars and Miley Cyrus. What’s the process of tracking these artists down and convincing them to work with you on a new track or album?When you’re in the studio, why is listening such an important part of your creative process? You interview a variety of artists for your podcast The FADER Uncovered. What types of creative struggles do your guests have in common and how did they break through them to achieve success? What is your best piece of career advice? Video interview Follow Mark’s journey: WebsitePodcastFacebookTwitterYouTubeInstagram

My guest today is actor and author, Danny Trejo. Danny is one of Hollywood’s most recognizable, prolific, and beloved character actors. He’s starred in AMC’s Breaking Bad, FX’s Sons of AnarchyDesperado, Machete, and Spy Kids. Danny owns restaurants including Trejo’s Tacos, Trejo’s Cantina, and Trejo’s Coffee & Donuts in the Los Angeles area. We discuss his remarkable journey from prison to blockbuster movies, which is captured in his new memoir “TREJO”, during this podcast episode. The 5 questions I ask in this episode: Why were you originally drawn into the systems of crime and violence and how were you able to transition into a new life as a Hollywood actor? How did your struggles with addiction, crime, and an abusive childhood inspire your acting roles and serve as motivation for your career? In your long career spanning hundreds of acting credits, how have you been able to separate the person people see in movies from who you are as a person? Why has it been difficult for you to help your children with the struggles they’re experiencing when you’ve already been through them? What’s your best piece of career advice? Video interview Follow Danny’s journey: WebsiteBookFacebookTwitterInstagram

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 winning two NBA championships. More recently, he wrote his first book, “Letters to a Young Athlete”. We discuss the book, as well as the obstacles he overcame throughout his career, during this podcast episode. The 5 questions I ask in this episode: How did watching basketball with your father, and playing with your friends, inspire you to pursue a career playing professionally? How did you deal with the pressure after losing to the Dallas Mavericks during the 2011 NBA Finals and how did it motivate you to win both the 2012 and 2013 championships? Early in your career, you had health issues that forced your retirement. How did you cope with the inability to continue playing basketball and then reinvent yourself? What did you learn during your time playing basketball that has helped you with this phase of your career? What’s your best piece of career advice? Video interview Follow Chris’s journey: WebsiteBooksFacebookYouTubeTwitterInstagram

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 podcast episode. The 5 questions I ask in this episode: While your early childhood ambition was to become a cyclist, your fate changed after a horrible accident and with encouragement from friends, you pursued a fashion career instead. What gave you the reassurance that fashion was right for you and what were the first steps to break into the industry? I’ve interviewed many designers for this podcast including Betsey Johnson, Steve Madden, and Diane von Furstenberg who have successfully built and sustained their companies. How has your brand stayed relevant for so long and what aspects of your personality and style make your brand unique in the ultra-competitive retail world?Your monograph book captures your creativity and unique spirit. Even though you’ve said that “the key thing to creativity is that you just have to go with it”, what are your sources of inspiration and the obstacles that get in the way of your creative thinking? As a customer of yours, full disclosure, I remember trying to order a sweater during the start of the pandemic but was unable to because you had suspended your eCommerce sales. You’ve said that Covid is the most devastating challenge you’ve faced in 50 years. What were the hardest decisions you made to keep your company afloat and your workers safe? What is your best piece of career advice? Video interview Follow Paul’s journey: CompanyBooksFacebookTwitterInstagram

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 for his new projects and lessons learned during this podcast episode. The 5 questions I ask in this episode: During our last conversation for this podcast two years ago, you shared your vision for the future of real estate, which you recently brought to life with your company “Serhant”. What was your process for turning your vision into a reality?In your book, you describe “Big Money Energy” as having self-confidence. How can someone overcome the self-doubt that is preventing them from realizing their true potential? Who are some of your idols or mentors that have the energy that has inspired you to think bigger and work harder? Part of what I think has made you successful is your personal and intentional approach to connecting with others. Two examples are when you send me a book with a note and when you showed up to my NYC book launch. Can you share a story about how one of your small gestures has led to a big breakthrough for you in your career or life?What’s your best piece of career advice? Video interview Follow Ryan’s journey: CompanyBooksLinkedInFacebookTwitterYouTubeInstagram

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 his career and his latest book, “Post Corona: From Crisis to Opportunity” during this podcast episode. The 5 questions I ask in this episode: You’ve started and sold companies, while also serving on the board of directors of major brands. What have these experiences over the past 29 years taught you about building, growing, and sustaining a successful business? Speaking of heartbreaking, the Covid-19 pandemic has exacerbating economic inequality. The World Bank estimates that as many as 150 million Americans will be in “extreme poverty” this year as we continue to face business closures, a recession, and a global health crisis. What do you recommend to people who have been most harmed under these conditions and to companies and policy makers on how to solve this problem?We both agree that Covid has accelerated change for better or worse. What do you predict will be the lasting impact on our lives post-Covid and how can we prepare for it?People are told to follow their passion but not every passion turns into a career, most should remain as hobbies. And, you’ve said to follow your interest, not passion. How does someone decide whether to turn their passion or interest into a career or not?What is your best piece of career advice? Video interview Follow Scott’s journey: Website BooksLinkedInFacebookTwitter