5 Questions With Dan Schawbel

My guest today is author and global health advocate, Chelsea Clinton. Chelsea is the Vice-Chair of the Clinton Foundation, and the author of “She Persisted in Science”. We talk about the book, defining moments in her life, and time management during this podcast episode. This episode is proudly sponsored by isolved, a complete workforce management solution. Go to https://www.isolvedhcm.com/ for more information. The 5 questions I ask in this episode: What defining moments and experiences in your childhood made you the person you are today? How do you divide your time between being a parent, wife, sitting on boards, podcasting, being a global health advocate, and writing books and how do they each complement one another? Women made up 40% of the nation’s scientists in 2019, which is up only 1% point since 2016. What’s holding women back from pursuing a STEM-focused career and what can we do to encourage them? As a mom, how have you encouraged your daughter to pursue a career where she’s making a difference? What’s your best piece of career advice? Video interview Follow Chelsea’s journey: BookFacebookTwitter

My guest today is the founder and CEO of Spartan, Joe De Sena. Joe’s company Spartan is the world’s leading endurance sports company with brands including Tough Mudder and Spartan Trail. He is also the bestselling author of Spartan Up, Spartan Fit, and The Spartan Way. More recently, he’s the host of the new CNBC primetime show, “No Retreat: Business Bootcamp”, which premiered Tuesday, March 8th. We talk about the show, and his entrepreneurial story, during this podcast episode. The 5 questions I ask in this episode: As a teenager, you had a pool cleaning business servicing 750 customers. What did this experience teach you about operating a business that has helped you in your current endeavors? How were you able to combine your love for intense outdoor activities and entrepreneurship into Spartan and the Death Race? How can physical and mentally challenging activities outside of the office build better leaders and teams? During the first episode of your CNBC Show “No Retreat Business Bootcamp”, what unorthodox approaches did you use to help a privately owned cleaning business? What’s your best piece of career advice? Video interview Follow Joe’s journey: WebsiteShowFacebookInstagramTwitter

My guest today is founding member of Run-DMC, Darryl McDaniels. Darryl changed music and made history when he broke down cultural barriers with his legendary band Run-DMC. Today, he’s the publisher of Darryl Makes Comics, the author of the children’s book “Darryl’s Dream” and co-founder of the Felix Organization. We talk about his career, comics, and everything he’s doing to support children, during this podcast episode. The 5 questions I ask in this episode: What influence did both Grandmaster Flash and comic books have on you growing up? How did the success you had with Run-D.M.C lead to depression and alcoholism and what did you do to recover? You co-founded a non-profit and wrote a book that supports children. How have you used these platforms to help children gain self-awareness and build self-confidence? We both love comics. As a kid, I collected DC but now with the Marvel Universe I’ve been collecting Marvel comics and their NFT counterparts on VeVe. How has Darryl Makes Comics allowed you to tell stories in a unique way as opposed to your music and books? Back in 2013, I asked Rev Run for his best piece of career advice and he said “you have to be able to do things that you know will work”. What is your best piece of career advice? Video interview Follow Darryl’s journey: WebsiteBookFacebookInstagramTwitter

My guest today is actor, comedian, and writer, Randall Park. Randall gained popularity with his appearance in NBC’s The Office, then went on to appear in ABC’s Fresh Off the Boat. He’s also appeared in movies such as The Interview, Ant-Man and the Wasp, and Aquaman. More recently, he stars alongside Ed Helms in True Story on Peacock. We discuss the show and his career, during this episode. The 5 questions I ask in this episode: How did your experiences founding the LCC Theatre Company in college spark your desire to become an actor? What are some of the ways you incorporated your Asian American heritage in your projects? How did you overcome both not having an agent, and your parents not being fully bought into your acting career when you were starting out? What did you learn about the world we live in while listening to and reenacting people’s stories in your show “True Story”? What’s your best piece of career advice? Video interview Follow Randall’s journey: Show

My guest today is Olympic athlete and author, Apolo Ohno. Apolo earned eight Olympic medals in speed skating and became the most decorated US Winter Olympian of all time. Today, he is as a cross-industry entrepreneur, successful sports broadcaster, and TV personality. I speak to him about his latest book “Hard Pivot” during this podcast episode. The 5 questions I ask in this episode: How instrumental was your father in helping you start your athletic career at such an early age?What internal and external pressures did you have as you were moving up the speed skating ranks, and competing for championships and how did you deal with them? Can you share some of your strategies for overcoming challenging times that you capture in your book “Hard Pivot”? Why was it so difficult to retire from speed skating and how were you able to transition to this next phase of your career as an entrepreneur, broadcaster, and author? What is your best piece of career advice? Video interview Follow Apolo’s journey: Website BookInstagramFacebookTwitter

My guest today is founder and Executive Chairman of ClassPass and author of LifePass, Payal Kadakia. Payal built ClassPass into the decades first billion-dollar company while being pregnant back in 2020 and recently sold it to Mindbody. She’s been named one of Fortune’s 40 under 40 and Fast Company’s 100 Most Creative People. Payal is also the founder of The Sa Dance Company, a contemporary Indian dance company. We talk about her new book, LifePass, as well as her entrepreneurial journey, during this podcast episode. The 5 questions I ask in this episode: Why did you only allocate 14 days to come up with the original idea for your company? Can you describe the unique goal-setting method that you wrote about in “Life Pass”? After the acquisition of your company by Mindbody last year, how did you decide what to focus on next? What were some of the lessons you learned during your time leading ClassPass that will help you throughout the rest of your career? What’s your best piece of career advice? Video interview Follow Payal’s journey: Website BookInstagramLinkedInTwitter

My guest today is former NBA player turned coach, author, and entrepreneur, Charles Oakley. Charles played nineteen seasons in the NBA, including his time with the Chicago Bulls, the New York Knicks, and the Toronto Raptors. Throughout his basketball career, he played with some of the all-time greats including Michael Jordan and Patrick Ewing. More recently, he wrote his memoir “The Last Enforcer”, which we discuss in this podcast episode. The 5 questions I ask in this episode: What inspired you to become a basketball player in your youth and how did you pursue that career? What about your personality, and life experiences, made you the enforcer on the court? In your book “The Last Enforcer” you discuss your relationship with George Floyd. Can you talk about what he meant to you and the lasting impact you think he will leave on the world? Which of your teammates or opponents did you learn the most from and why? What’s your best piece of career advice? Video interview Follow Charles’s journey: BookInstagram FacebookTwitter

My guest today is Linkin Park co-founder, Mike Shinoda. Mike co-founded Linkin Park in 1996 and is the band’s lead vocalist, as well as rhythm guitarist, keyboardist, primary songwriter, and producer. More recently, he released the solo hybrid mixtape and NFT project Ziggurats and has been Twitch streaming regularly on his channel. We talk about all his latest projects during this podcast episode. The 5 questions I ask in this episode: What influence did your mother have on your music career? After forming LinkedIn Park with your high school friends, how did overcome the challenge of landing your first record deal? As a musician, producer, Twitch streamer, gamer, and graphic designer, how do you decide what projects to work on now and which ones to save for the future? You recently released your music/NFT hybrid project Ziggurats. How do you see NFTs transforming the music industry and what do they mean for artists moving forward? What is your best piece of career advice? Video interview Follow Mike’s journey: WebsiteInstagram FacebookTwitchYouTube

My guest today is filmmaker and social media content producer, Zach King. Zach is known for his clever magic tricks and has amassed over 100 million followers. His company, King Studio, has partnered with brands such as Disney, Apple, Sony, Nike, and Coca-Cola. We talk about how he’s built his film and social media career during this podcast episode. The 5 questions I ask in this episode: How did a rejection letter from film school motivate you to build a career in film? You made your first film at age seven that had a small audience and today your content is viewed by a mass audience. How has your creative process evolved, and how do you continue to keep yourself relevant? As a content creator, you’re also a storyteller. What do you think are the elements of a story that captures people’s hearts and minds? Companies, leaders, and influencers are all feeling the social pressure to speak out right now against racial inequality and injustice. What do you feel is your responsibility to your audience when it comes to social and political issues? What’s your best piece of career advice? Video interview Follow Zack’s journey: WebsiteInstagram FacebookTik TokTwitter

My guest today is bestselling author and speaker, Dan Pink. Dan is the author of several books including the New York Times bestsellers When, Drive, To Sell Is Human, and A Whole New Mind. His books have won multiple awards and have been translated into more than 40 languages. We discuss his latest book, The Power of Regret: How Looking Backward Moves Us Forward, during this podcast episode. The 5 questions I ask in this episode: How did you transition from being a political speechwriter to an author? What new research did you uncover about having regrets that most surprised you? Why do you suggest that we stop trying to live life without regrets? How can our regrets improve our work-life decisions? What’s your best piece of career advice? Video interview Follow Dan’s journey: WebsiteBook FacebookLinkedInTwitter

My guest today is documentarian, journalist, and co-host of Everyday Wealth, Soledad O’Brien. Soledad has anchored shows on CNN, MSNBC, and NBC, and hosted projects for Fox and A&E. She is the CEO of Soledad O’Brien Productions, a multiplatform media production company, and co-hosts the Everyday Wealth radio show with Jean Chatzky, presented by Edelman Financial Engines, where they help people achieve their financial goals. We talk about her inspiring career journey and commitment to helping others manage their finances during this podcast episode. The 5 questions I ask in this episode: What did you learn from your parents that allowed you to persevere and make a name for yourself? While many people make new year’s resolutions, only 9% keep them by the end of the year. What are some of your resolutions and how are you committed to seeing them through? Aside from being a journalist and documentarian, you are involved in other projects that focus on empowering people with the right financial tools they need to succeed. How did you overcome your own financial challenges and what did you learn in the process that can help others? How are you tackling societal issues like education and gender inequality and why are they so important to you? What is your best piece of career advice? Video interview Follow Soledad’s journey: WebsiteEveryday Wealth, presented by Edelman Financial EnginesFacebookInstagramTwitter

My guest today is the cofounder and co-executive chairman of The Carlyle Group, David Rubenstein. David’s The Carlyle Group is one of the world’s largest and most successful private equity firms. He is the Chairman of the Boards of Trustees of the John F. Kennedy Center for the Performing Arts and the Council on Foreign Relations. He is an original signer of The Giving Pledge and a recipient of the Carnegie Medal of Philanthropy and the MoMA’s David Rockefeller Award. We discuss his book “How to Lead” during this podcast episode. The 5 questions I ask in this episode: David, I’ve spoken with a variety of leaders about how they are navigating this crisis and they are all in agreement that trust is the most important asset right now. What did you learn from all of your interviews on how to build and cultivate trust? How has collecting stories of successful people affected you personally, changed your outlook on life, and made you a better leader? What do you find are the common qualities all successful leaders have in common and what are some of the unique qualities you’ve discovered that separate them? You’ve amassed a fortune in private equity and have also taken the giving pledge to donate half of your wealth to charities of your choosing. What would you say to persuade other prominent people to be more philanthropic and how do you decide which causes to donate to? What’s your best piece of career advice? Video interview Follow David’s journey: WebsiteBookTwitter

My guest today is TED speaker and bestselling author, Amy Cuddy. Amy is a social psychologist that rose to fame after her TED Talk “Your Body Language May Shape Who You Are” became a worldwide sensation with over 62 million views and growing. She wrote the book, Presence, which became a New York Times bestseller, and was a professor at Harvard Business School. We talk about her mentor, body language, and overcoming uncertainty during this podcast episode. The 5 questions I ask in this episode: What role did your mentor Susan Fiske play in helping you shape your career? Your TED Talk and research focuses on body language. How does our body language shape how people perceive us when we’re connecting and working remotely instead of in person? What types of struggles did you endure over the past year during the pandemic and how did you overcome them? What is Pandemic Flux syndrome and how do we get through it? What’s your best piece of career advice? Video interview Follow Amy’s journey: TED TalkBookInstagramTwitterLinkedIn

My guest today is Destiny’s Child member and author, Michelle Williams. Michelle rose to fame as a member of the R&B group Destiny’s child, one of the best-selling female groups of all time with over 60 million records sold. After the group disbanded in 2006, she went on to release solo albums, appeared in Broadway shows, and acted in several sitcom series like Chicago and The Color Purple. More recently, she wrote Checking In and The Daily Check-In, which we discuss in this podcast episode. The 5 questions I ask in this episode: After graduating from high school, why did you doubt your ability to make a career as a professional singer and pursue a criminal justice degree? After meeting Beyonce and Kelly Rowland in the lobby of an Atlanta hotel, how did you know that you could make it as a music group? When you were rising to fame, a lot of people were dishing you advice. What’s the balance between getting counsel from others and listening to your inner voice when making big career decisions? You talk about your anxiety and depression in your book “Checking in”. What did you learn during your process of healing that can be useful to anyone looking to better manage their mental health? What is your best piece of career advice? Video interview Follow Michelle’s journey: WebsiteBookInstagramTwitter

My guest today is McFarlane Toys CEO, Spawn creator, and Venom co-creator, Todd McFarlane. Todd has established himself as a force in the entertainment world with 1 Grammy Award, 2 Grammy nominations, 2 Emmy Awards, 2 MTV Video Music Awards, 1 Canadian MuchMusic Award, and more than 150 International awards in the fields of action figures, comic books, and publishing. Aside from creating Spawn, and co-creating Venom, he’s the co-founder and president of Image Comics, has launched an NFT marketplace with Steve Aoki called OddKey, and two new premium TV series “McFarland” and “Thumbs”. We talk about his history with comics, and all of these new projects, during this podcast episode. The 5 questions I ask in this episode: How did you originally develop your interest in comics and when did you know it could become a career? What was your creative process like for creating generational characters like Venom and Spawn? Aside from being a comic book icon, you’re also an NFT icon with VeVe’s first NFT of your #100 Batman Todd McFarlane statue and your new NFT marketplace with Steve Aoki who was a previous podcast guest. As someone who has worked in both the physical and NFT worlds, do you think both will complement each other or will one replace the other? You have so many different projects happening simultaneously between your TV shows, comics, toys and NFTs. How do you decide which characters you use in different mediums at different times, while ensuring there’s no oversaturation? What’s your best piece of career advice? Video interview Follow Todd’s journey: WebsiteInstagramTwitterFacebook

My guest today is Wu-Tang Clan founding member, Raekwon. Raekwon achieved success with Enter the Wu-Tang (36 Chambers) in 1993 and followed it up with his platinum solo debut, Only Built 4 Cuban Linx, and countless classic collaborations. He is also an entrepreneur and the founder of his own label, ICE H2O Records. We talk about his life story, and Wu-Tang, as captured in his book “From Staircase to Stage”, during this podcast episode. The 5 questions I ask in this episode: How did you deal with both rivalries and racism in your childhood growing up in Staten Island New York? What aspects of the relationship between the Wu-Tang Clan members made the group both very successful but also lead to breakups and arguments? How did your recovery after 4 gunshot wounds lead to you honing your creative process? How did spirituality, your fans, being a father, and idols like Run-D.M.C. inspire your work? What is your best piece of career advice? Video interview Follow Raekwon’s journey: BookInstagramTwitterYouTubeFacebook

My guest today is NBA All-Star and author, Dwyane Wade. Dwyane is a three-time NBA champion, businessman, TV analyst, producer, activist, and philanthropist. He played in the NBA from 2003 to 2019, primarily for the Miami Heat. He won three NBA championships, was a 13-time NBA All-Star, an 8-time member of the All-NBA Team, and a 3-time member of the All-Defensive Team. We talk about his life and career, as captured in his memoir “Dwyane”, during this podcast episode. The 5 questions I ask in this episode: What were some of your biggest challenges growing up in the South Side of Chicago and how did facing them help you become the person you are today? How did Michael Jordan’s career inspire you to become a professional basketball player? After having your own line of shoes with Converse and Nike’s Jordan Brand, why did you decide to work with Li-Ning on building your own brand? In what ways do you see yourself as a leader of the trans rights movement? What is your best piece of career advice? Video interview Follow Dwayne’s journey: BookInstagramTwitterFacebook

My guest today is chairman of VaynerX and author, Gary Vaynerchuk. Gary is one of the world’s leading marketing experts, the CEO of global creative and media agency VaynerMedia, and an investor in companies like Facebook, Twitter, Venmo, and Uber. He’s also the creator of VeeFriends, an NFT collection, and has millions of followers on social media. We first connected back in 2007 when we were showing the world the power of personal branding using social media and this is our 6th interview. We talk about his new book “Twelve And A Half”, as well as his views on NFTs, during this podcast episode. The 5 questions I ask in this episode: While you cover the 12 essential emotional skills in the book, there’s also a half. Which skill do you feel weakest in and how are you trying to improve it so you can be more effective in every area of your life?How have you tailored your soft skills to different people, environments, and situations? I love how you included “curiosity” as one of your top skills because most people wouldn’t think of it as a skill. How has your curiosity led you to experiment, and have breakthroughs, in your businesses?You’ve said that 98% of NFTs projects will “go to Zero” and called for an “NFT Winter”. What do you think will be the 2% that appreciate in value long-term? What’s your best piece of career advice? Video interview Follow Gary’s journey: WebsiteAmazonYouTube InstagramTwitterFacebook

My guest today is actress, singer, and TV personality, Lucy Hale. Lucy first became known for her roles in the series Bionic Woman and Privileged, then had her breakthrough starring role in Pretty Little Liars. She’s also starred in films such as Scream 4, Dude, and Fantasy Island. Lucy ventured into music releasing her album Road Between back in 2014. More recently, she stars as the lead in Ragdoll, a crime drama series for AMC and Alibi based on the novel by Daniel Cole. We talk about her new series, acting career, and more during this podcast episode. The 5 questions I ask in this episode: In your childhood, how did you balance the time between taking acting and singing lessons while being homeschooled? You’ve had multiple shows that have been canceled. Even if you felt good about your performance, how do you both continue to persevere and make decisions about the next projects? Even though you are a successful actress you had to fight for the starring role of AMC’s Ragdoll. Why was it such a challenge for you to land the role and how did you eventually get it? What inspired you to support eco-friendly products, like Karma’s plant-first dog food? What’s your best piece of career advice? Video interview Follow Lucy’s journey: Show InstagramTwitterFacebook

My guest today is actor and former White House staff member, Kal Penn. Kal has played leading roles in some of the world’s most-watched television shows, including How I Met Your Mother, 24, House, and more. He currently stars in the CBS series Clarice, a sequel to The Silence of the Lambs, and the Disney Junior animated series Mira, Royal Detective. He has starred in movies that have collectively grossed more than a billion dollars, including the Harold and Kumar franchise. Kal has worked at the very highest levels of politics, as an Associate Director of the White House Office of Public Engagement. We discuss both his acting and political careers, as captured in his book “You Can’t Be Serious”, during this podcast episode. The 5 questions I ask in this episode: Why did you reject the advice of your family and guidance counselors to become a doctor and instead pursue a career in acting? What stories did you hear about your grandparents that influenced you to get into politics? What did you learn in your acting career that made you a more effective politician? How did you overcome the struggles of trying to make it in Hollywood like racism and the feeling of not fitting in? What’s your best piece of career advice? Video interview Follow Kal’s journey: Book InstagramTwitterFacebook

My guest today is magician and entertainer, David Copperfield. David is one of the greatest illusionists and most commercially successful magicians in history. He’s won 21 Emmy Awards, 11 Guinness World Records, sold over 33 million tickets, and has been named a Living Legend by the U.S. Library of Congress. We talk about the history of magic as captured in his new book, “David Copperfield’s History of Magic”, during this podcast episode. The 5 questions I ask in this episode: What was it about the magic store you went to when you were a kid that inspired you to become a magician instead of a ventriloquist? You’re known for your tricks like making the statue of liberty disappear and escape from death. What goes through your mind when you perform these tricks, knowing that they could go wrong or be exposed? You’ve profiled the best magicians in your book “David Copperfield’s History of Magic”. Which ones have had the most influence on your career and why? Looking back at the history of magic, what do you think were the pivotal milestones that brought the art, tricks, and shows forward? What is your best piece of career advice? Video interview Follow David’s journey: WebsiteBook InstagramTwitterFacebook

My guest today is actress and podcaster, Gabby Sidibe. Gabby made her acting debut in the 2009 film Precious, where she was nominated for both a Golden Globe and Academy Award for Best Actress. She’s also appeared in the Fox show Empire, multiple American Horror Story TV series, and Tower Heist. More recently, she stars in the original Realm thriller podcast, If I go Missing the Witches Did It.” We talk about the podcast, her acting career, and more during this podcast episode. The 5 questions I ask in this episode: How did you handle family members bullying you about your weight as a child and then how did losing 100 pounds during surgery impact your self-esteem? After starting your career with a breakout role starring in Precious, how did you choose your next project? How is your new podcast “If I Go Missing the Witches Did It” different from your prior work and what have you learned during the production process? In what ways have you addressed the issues of race, class, and capitalism in your show? What’s your best piece of career advice? Video interview Follow Gabourey’s journey: PodcastInstagramTwitter

My guest today is actor, writer and producer, Stanley Tucci. Stanley has directed five films and appeared over seventy, including The Devil Wears Prada and Road to Perdition, as well as more than a dozen plays, on and off-Broadway. He starred in Julie & Julia, opposite Meryl Streep, and The Lovely Bones, for which he earned his first Academy Award nomination, for Best Supporting Actor. He is the winner of two Golden Globes and two Emmys. His foody TV show, Stanley Tucci: Searching for Italy, recently aired on CBS and is Emmy nominated. We talk about his life journey, overcoming setbacks, and his new book “Taste: My Life Through Food” during this podcast episode. The 5 questions I ask in this episode: What role did your family play in your pursuit as an actor? Even after you received an Emmy nomination for your breakout role in Murder One, how were you able to recover from the show being canceled? 3Where did your passion for food originally come from and how were you able to incorporate it into your TV career? How have your recent health struggles impacted your life and career trajectory? What’s your best piece of career advice? Follow Stanley’s journey: Book InstagramFacebook

My guest today is the chairman and CEO of Dell Technologies, Michael Dell. Michael started Dell in his dorm room at the University of Texas and today it’s become of the most successful technologies companies in the world. He is one of the 25 richest people in the world with a net worth of $51.7 billion and Dell Technologies made over 90 billion in revenue this year. We talk about his entrepreneurial journey, which he covers in his memoir “Play Nice But win”, during this podcast episode. The 5 questions I ask in this episode: How did both selling newspaper subscriptions and playing with technology as a teenager lead you to start your company? You’ve had many failures over decades of running DELL. What have you learned from these experiences that helped you make better business decisions? How do you evaluate talent when making hiring decisions? Billionaire CEOs like Jeff Bezos, Jack Dorsey, and Elon Musk have started multiple companies or have ventured into space. Do you have any plans for your next act and how do you intend to spend the rest of your life? What is your best piece of career advice? Video interview Follow Michael’s journey: Book InstagramFacebookTwitter

My guest today is singer, songwriter, and actor, Jesse McCartney. Jesse’s first three albums made the Top 15 of the Billboard Top 200 and is most known for his singles “Beautiful Soul” and “Leavin”. He’s performed and collaborated with T-Pain, New Kids on the Block, and Backstreet Boys. He’s appeared in Fear The Walking Dead and Alvin and the Chipmunks. Jesse’s first album in seven years is called “Next Stage”. We talk about everything from the inspiration for the album to growing up as a pop star during this podcast episode. The 5 questions I ask in this episode: What were some of the negative implications of being a big pop star at such a young age? What obstacles did you encounter as you transitioned from being in a boy band to your solo career and how did you overcome them? How has your creative process changed from when you were a teenager to right now? You are releasing your first album in 7 years. How did the time you spent reflecting on your life inspire your new music? What is your best piece of career advice? Video interview Follow Jesse’s journey: Website InstagramFacebookYouTubeTwitter

My guest today is rapper and entrepreneur, Rick Ross. Rick’s breakout single “Hustlin” back in 2006 made him an international sensation overnight. Today, he’s the founder of the Maybach Music group, has ten albums that have made the Billboard 200 list, and received four Grammy Award nominations. Rick’s new book is called “The Perfect Day to Boss Up”, which we discuss in this podcast episode. The 5 questions I ask in this episode: What were some early childhood experiences that helped you learn how to be a businessman and eventually launch successful ventures?During the grind of building your brand and career, what was the daily motivation that helped you persevere through the stress and failures?What are some of your “Boss Commandments” that people can implement to improve their lives?Over the past year, you cut your own grass instead of paying someone else to do it for you and flew commercial over private. Why did you choose to do these activities even though you don’t have to?What is your best piece of career advice? Video interview Follow Rick’s journey: Book YouTubeInstagramFacebookTwitter

My guest today is rapper and record producer, Bobby Hall. Known professionally as Logic, Bobby has released six studio albums and received two Grammy Award nominations. He recently retired from music to be a father and write his latest book “This Bright Future”. We discuss his life transformation, overcoming trauma, and lessons learned during this podcast episode. The 5 questions I ask in this episode: Can you talk about how you see your life transformation from being born Sir Robert Bryson Hall II to Bobby Hall and now Logic? How did retiring from music to focus on being a father change how you want to work and live moving forward? What was the most traumatic situation you experienced that had the most impact on your personal and professional growth? One of the similarities I’ve noticed in my interviews is that someone’s weakness can be a strength in disguise. There are silver linings that come from pain. How do you think your mental health struggles have been a driver of your success? What’s your best piece of career advice? Video interview Follow Bobby’s journey: YouTube InstagramFacebookTwitter

My guest today is singer, songwriter, and guitarist, Melissa Etheridge. Melissa rose to fame with her mainstream breakthrough album, “Yes I Am”, with singles including “I’m the Only One” and “Come to My Window”. Throughout her career, she’s received 15 Grammy Award nominations and won two of them. More recently, Melissa released her new album “One Way Out” which has unreleased songs from the 1980s and early 90s. We talk about the album, her childhood, dealing with loss, and more during this podcast episode. The 5 questions I ask in this episode: Growing up in Kansas, when did you realize that you could turn your music into a career? You were discovered in a gay bar, yet the record label asked in a meeting, “what are we going to do about this gay thing?” How did they eventually come around to accept you for who you are? You recently lost your son to opioid addiction and beat cancer several years ago. How have these experiences changed how you think about your life and career? Why did you decide to release songs you recorded decades ago this year? What is your best piece of career advice? Video interview Follow Melissa’s journey: Website YouTube InstagramFacebookTwitter

My guest today is the lead vocalist of OneRepublic, Ryan Tedder. Ryan started played music at age three and since then has become one of the most successful songwriters and producers of his generation. He’s worked with everyone from Adele to Beyonce to The Jonas Brothers. I talk to Ryan about his early career, relationship with money, time management, and collaborations during this podcast episode. The 5 questions I ask in this episode: How did your parents encourage you to play music and sing starting at age 3 and what role do they play in your career today? You didn’t grow up with money and graduate college fully in debt. How have these life circumstances affected your relationship with money now that you’re wealthy? Aside from being the lead singer in OneRepublic, you’re also a top producer. How do you manage your time between both, while pursuing other projects and social life? When you’re writing and producing a new song how do you integrate the artist’s personality into the music? What is your best piece of career advice? Video interview Follow Ryan’s journey: Website InstagramFacebookTwitter

My guest today is the Two-time Emmy Award-Winning Anchor of Inside Edition, Deborah Norville. Deborah is currently the longest-serving anchor on American television and an inductee into the Broadcasting & Cable Hall of Fame. She is the former co-host of NBC’s “Today” and current anchor of Inside Edition, with over 5 million daily viewers. She’s also on the Board of Directors of Viacom. We talk about her longtime career, and overcoming obstacles, during this podcast episode. The 5 questions I ask in this episode: What did you learn about TV production in high school when you were in the Junior Miss beauty contest? You’re one of the longest-running anchors on TV. What do you think has led to your longevity in such a competitive industry? You’ve encountered major obstacles like a jail sentence, being overweight and corporate politics. What is it about you that lets you persevere, and triumph, through these obstacles? As someone who also speaks to many luminaries, what are some of your best interview tips? What’s your best piece of career advice? Video interview Follow Deborah’s journey: Website InstagramFacebookTwitter

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

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