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5 Questions With Dan Schawbel

Dan Schawbel, #1 Bestselling Author, Speaker, Entrepreneur

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New York Times bestselling author Dan Schawbel distills the most actionable and tangible advice from a variety of world-class humans including entrepreneurs, authors, Olympians, politicians, billionaires, Nobel Prize winners, TED speakers, celebrities, astronauts and more.
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Top 10 5 Questions With Dan Schawbel Episodes

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My guest today is singer, songwriter, and pianist, Tori Amos. Tori has composed songs that focus on a broad range of topics including politics and religion since the 1980s. She’s been listed as VH1’s “100 Greatest Women of Rock and Roll” and has received 5 MTV VMA and 8 Grammy Award nominations. I spoke to Tori about the times and tribulations of her career, as she wrote in her book “Resistance”, during this podcast episode.

The 5 questions I ask in this episode:

  1. Unlike your siblings, you didn’t need piano lessons growing up because it came naturally to you. When did you realize that you had musical talent and what motivated you to turn that talent into a career?
  2. In the 1980s you signed with Atlantic Records, moved to LA, and formed a band producing an album that wasn’t successful. What did you learn from this experience that proved to be useful later?
  3. How has your role as an artist changed since you first started your career and what obstacles do today’s artists have to overcome to sustain themselves?
  4. You have created decades worth of music influenced by social and political movements. Our world feels more divided than ever, yet issues like the coronavirus pandemic, climate change, and income inequality require all of us to band together. How do you think your music and this book can provide encouragement to people who want to make a difference?
  5. What’s your best piece of career advice?

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An interview with Morgan Spurlock about how he gets ideas for his projects, how documentaries get made, how he learned to be a storyteller, what his life purpose is and his best career advice.

Welcome to the 52nd episode of 5 Questions with Dan Schawbel. As your host, my goal is to curate the best advice from the world’s smartest and most interesting people by asking them just 5 questions.

This episodes guest:

My guest today is documentary filmmaker and producer, Morgan Spurlock. Born in Parkersburg, West Virginia, Morgan graduated from New York University’s Tisch School of the Arts in 1993. He started his career as a successful playwright before eventually producing Super Size Me, an Academy Award-nominated documentary that tracked his health as he ate three McDonalds meals each day for thirty days. I get sick to my stomach even thinking about it! This film completely changed my diet and led to my pursuit of a health lifestyle. Morgan has gone on to produce several other documentaries, including Where in the World is Osama Bin Laden?, Freakonomics and The Greatest Movie Ever Sold. More recently, he released his big follow up documentary, Super Size Me 2: Holy Chicken, which explores how the fast food industry has rebranded itself as healthier since the first film. The film isn’t what I expected at all. Morgan literally goes through the entire process of opening a fast food restaurant, called Holy Chicken, in order to expose the food industry. I had the opportunity to sit down with him the same week when he opened a pop-up restaurant in New York City.

Video interview from New York City:

The 5 questions questions I ask in this episode:

  1. How do you get the ideas for your documentaries and what are the first steps for producing them?
  2. What are some things that people don’t know about what it takes to create a documentary?
  3. When did you decide to be a storyteller and when did you know you were effective at it?
  4. All of your films make a huge impact and have changed the food industry. Do you feel like you have a sense of purpose? What mark do you want to leave on the world?
  5. What is your best piece of career advice?

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An interview with Gary Chapman about the most common relationship mistake people make, how our love languages can bring us closer together, the balance between self-care and caring for others, using technology to strengthen relationships and his best career advice.

Welcome to the 47th episode of 5 Questions with Dan Schawbel. As your host, my goal is to curate the best advice from the world’s smartest and most interesting people by asking them just 5 questions.

This episodes guest:

My guest today is the #1 New York Times bestselling author of The Five Love Languages, Gary Chapman. Born in China Grove, North Carolina, Gary graduated the Moody Bible Institute, received Bachelors and Masters degrees from Wheaton College and Wake Forest. He continued his education at the Southwestern Baptist Theological Seminary, receiving both a Master of Religious Education and a Doctor of Philosophy degree. In 1971, Gary joined the Calvary Baptist Church, in Winston-Salem, North Carolina, and now holds the title of senior associate pastor. In 1992, he published his first and his most notable book, The Five Love Languages, which has now sold over 11 million copies in 49 languages. Since then, he’s authored many other books in the Five Love Language book series, including his latest entitled, Love Language Minute for Couples. Currently, Gary travels the world presenting seminars about building health relationships between couples, families and teams.

The 5 questions questions I ask in this episode:

  1. You’ve spent decades as a counselor and pastor. What is the most common mistake people make that hurts their relationships and how do they stop making it?
  2. How can knowing our love languages help bring us closer together at work and at home?
  3. What is the delicate balance between self-care and care for others?
  4. How has technology impacted relationships and what’s the best way to use it to get closer to others without letting it get in the way?
  5. What is your best piece of career advice?

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An interview with Elvis Duran about how he overcame mistakes in his childhood, how losing 100 pounds changed his life, coming out as gay, how do build a personal brand and his best career advice.

Welcome to the 50th episode of 5 Questions with Dan Schawbel. As your host, my goal is to curate the best advice from the world’s smartest and most interesting people by asking them just 5 questions.

This episodes guest:

My guest today is nationally syndicated radio host, Elvis Duran. Born in McKinney, Texas, Elvis started his career as an on-air personality at WIOQ, Philadelphia’s top music radio station, and eventually became the program director before getting fired back in 1990. A year later, he became the program director and morning show host of KGSR in Austin, Texas. From there, he had a stint at Z-93 in Atlanta and 104 in Houston, before finally landing at Z100 in New York City. As the daily host of the Elvis Duran and the Morning Show, he and his team grew to thirty stations in a single year. Today, the show is America’s most-listened-to Top 40 morning show and one of the 10 most-listened-to programs in all of radio, heard live by nearly 10 million people in more than 80 markets across the country. Like me, Elvis has interviewed many successful people, but is rarely the one being interviewed. That’s why I was excited to talk to him about his new memoir “Where Do I Begin?” at his legendary studio here in New York City.

Video interview from iHeart Radio in New York City:

The 5 questions questions I ask in this episode:

  1. Looking back when you were a teenager, what were some of the biggest mistakes you made and how did you overcome them?
  2. What is your several years ago you underwent a surgery where you lost over 100 pounds. How did that experience change your life?
  3. You came out as gay many years ago. Was it hard coming out on air as gay?
  4. What do you recommend to people who want to build and elevate their personal brand?
  5. What is your best piece of career advice?

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An interview with Chase Jarvis about the fine line between being a creative and entrepreneur, how he had the courage to pursue his career, what inspires him, how he decides whom to collaborate with and his best career advice.

Welcome to the 49th episode of 5 Questions with Dan Schawbel. As your host, my goal is to curate the best advice from the world’s smartest and most interesting people by asking them just 5 questions.

This episodes guest:

My guest today is photographer and CEO of CreativeLive, Chase Jarvis. Born in Seattle, Washington, Chase attended San Diego State University on a football scholarship. While his original goal after graduating was to attend medical school, his plans changed after his grandfather died and Chase inherited his photography equipment. He instead went on a trip to Europe to follow his passion to be a photographer, leading to an extremely successful career. He was hired by the likes of Volvo, Nike, Apple and Pepsi to shoot lifestyle, sports and landscape photography and has won numerous awards for his work. In 2010, Chase co-founded CreativeLive, an online education platform, with millions of students globally and three billion hours of education consumed. A year later he started his podcast, Chase Jarvis Live, and you can listen to my episode on it called “Less Phone, More Human.” I’ve known Chase since the early part of my career, which is why it’s a pleasure to have him on my podcast to talk about his book, Creative Calling. As a fellow creative and entrepreneur, I was interested in learning more about how he sees himself and how his creative pursuits ended up turning into a business.

The 5 questions questions I ask in this episode:

  1. Is there a fine line between being a creative and an entrepreneur?
  2. What gave you the courage to pursue your dream instead of living someone else’s?
  3. Who or what inspires your creative urges?
  4. How do you decide whom to collaborate with?
  5. What is your best piece of career advice?

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An interview with Brian Grazer about how face-to-face conversations have impacted him, how having dyslexia impacted his career, how he recovered from a poor connection, how technology can be a bridge to human connection and his best career advice.

Welcome to the 48th episode of 5 Questions with Dan Schawbel. As your host, my goal is to curate the best advice from the world’s smartest and most interesting people by asking them just 5 questions.

This episodes guest:

My guest today is film and TV producer and screenwriter, Brian Grazer. Born in Los Angeles, California, Brian graduated USC’s School of Cinema-Television in 1975 as a psychology major. After quitting USC’s Law School after one year, he pursued a career as a producer focused on TV projects for Paramount Pictures in the early 80s. There, he met friend and business partner Ron Howard, embarking on one of the longest running partnerships in Hollywood history. Together, their films and TV shows have been nominated for 43 Oscars and 195 Emmys and he won the Best Picture Oscar for A Beautiful Mind. In addition, Grazer produced hit films like American Gangster, Apollo 13, The Nutty Professor, 8 Mile, and Liar Liar. His films have generated more than $13.5 billion in worldwide theatrical, music, and video sales. His endless honors include having a star on the Hollywood Walk of Fame, being named one of TIME Magazine’s most influential people and a cameo on The Simpsons. His more recent projects include the Wu-Tang: An American Saga TV series and his new book Face to Face: The Art of Human Connection.

The 5 questions questions I ask in this episode:

  1. Why did you decide to write your book and how have face-to-face conversations impacting you personally and professionally?
  2. How did having dyslexia as a child affect you and put you on a new path to forming meaningful human connections?
  3. Can you give us an example of a poor interaction you’ve had and how you corrected it using the power of a face-to-face conversation?
  4. I always say, “Use technology as a bridge to human connection instead of letting it be a barrier between you and the relationships you seek.” How can we use technology to create more human relationships?
  5. What is your best piece of career advice?

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An interview with Ryan Holiday about his life philosophies, how to disconnect from technology to be more present, achieving stillness, stoicism’s affect on his parenting and his best career advice.

Welcome to the 51st episode of 5 Questions with Dan Schawbel. As your host, my goal is to curate the best advice from the world’s smartest and most interesting people by asking them just 5 questions.

This episodes guest:

My guest today is bestselling author, marketer and entrepreneur, Ryan Holiday. Born in Sacramento, California, Ryan dropped out of college at age 19 to apprentice under notable authors including Tucker Max, Tim Ferriss and Robert Greene, supporting their book marketing campaigns. After helping launch The 50th Law, Robert connected Ryan to American Apparel founder Dov Charney. Ryan served as the Director of Marketing for the company from 2009 until 2014, where he was responsible for many notable media stunts, which became the inspiration for his first book Trust Me, I’m Lying. Since then, he’s written several other books, including The Obstacle Is The Way, Ego Is the Enemy and his latest, Stillness Is the Key. I’ve known Ryan for many years and have always been impressed by his dedication to writing a book each year, how he supports the author community and his unique lifestyle, living on a farm outside of Austin, Texas. I was especially excited to have a discussion with Ryan about his new book because it’s relevant to my book, further emphasizing the importance of taking time away from technology to be present.

Video interview from New York City:

The 5 questions questions I ask in this episode:

  1. It’s been seven years of knowing you and this is our fourth interview. So after all of this time, what’s most changed for you and what’s remained the same in terms of your philosophy and how you live your life?
  2. People feel like they need to constantly be connected. How can people start to disconnect so they can be more present?
  3. How do you define stillness, what’s the feeling like when you’re achieved stillness and why should people try to do that?
  4. How will raise your kid differently after studying stoicism and other ancient philosophies?
  5. What’s your best piece of career advice?

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An interview with Sophia Amoruso about how her mental health issues affected her childhood, how she recovered from the lowest point in her career, why we need to promote our personalities, how women can break the glass ceiling and her best career advice.

Welcome to the 46th episode of 5 Questions with Dan Schawbel. As your host, my goal is to curate the best advice from the world’s smartest and most interesting people by asking them just 5 questions.

This episodes guest:

My guest today is the Founder of Girlboss Media and author of #GIRLBOSS, Sophia Amoruso. Born in San Diego, California, Sophia was raised in the Greek Orthodox church and later dropped out of school and began homeschooling after being diagnosed with ADHD and depression. Her first few jobs were working at a Subway restaurant, a bookstore and a record shop. After she graduated from high school her parents got divorced, which led to her living a nomadic lifestyle, including hitchhiking, dumpster diving and stealing. At age 22, she opened an eBay store called Nasty Gal Vintage, which then led to launching a Nasty Gal retail store of her own. Nasty Gal grew to a $23 million dollar company in just three years. She then wrote the bestseller, #GIRLBOSS, which was later adapted into a Netflix series. Then, between 2015 and 2016 she stepped down as CEO of Nasty Gal, filed chapter 11, until the company was bought in 2017. Then, she launched Girlboss Media, with content geared to a female audience, which recently turned into a networking platform. Our last interview was four years ago so it was great to catch up with Sophia to better understand what she’s been through and how she’s overcome obstacles to push forward in her life.

The 5 questions questions I ask in this episode:

  1. Mental health is one of the most important yet misunderstood topics in our culture. How did being diagnosed with depression and ADHD in your childhood affect you?
  2. You’ve had ups and downs as an entrepreneur. What was your lowest point and how did you recover from it?
  3. Why do you believe that we need to promote our personalities, not just our resumes, when searching for a job? How can we do this?
  4. Part of my commitment with this podcast is to interview women. Women have always been underrepresented in leadership roles. How can women break the glass ceiling and what can men do to help?
  5. What is your best piece of career advice?

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An interview with Sanjay Gupta about what influenced him to get into the healthcare profession, how traveling the world covering healthcare changed his life, how we can combat the loneliness epidemic, his predictions for the future of healthcare and his best career advice.

Welcome to the 45th episode of 5 Questions with Dan Schawbel. As your host, my goal is to curate the best advice from the world’s smartest and most interesting people by asking them just 5 questions.

This episodes guest:

My guest today is neurosurgeon and Chief Medical Correspondent for CNN, Sanjay Gupta. Born in Novi, Michigan, Sanjay earned his degree in biomedical sciences at the University of Michigan in Ann Arbor, his M.D. from the University of Michigan Medical School and completed his residency in neurological surgery in the University of Michigan Health System. Today, Sanjay is an Emory Healthcare general neurosurgeon at Grady Memorial Hospital. Parallel to his medical career, he is a multiple Emmy-award winning correspondent for CNN and is the host of “Vital Signs”, where he travels the world to examine the most important medical stories like the future of food. Throughout his career, he’s famously covered the medical aspects of the Iraq war, the medical benefits of marijuana and social media’s impact on teens’ mental health. In this podcast, Sanjay talks about his career in the medical field, the future of our health and how we can overcome loneliness.

The 5 questions questions I ask in this episode:

  1. What were your childhood influences that inspired you to go into healthcare and media as an adult?
  2. How has traveling the world covering the biggest health topics of our time changed how you live your life?
  3. We have a loneliness epidemic that is affected about half of American adults. What can we do to make people feel less lonely?
  4. What are you most hopeful for, and most concerned about, when it comes to the future of our health?
  5. What is your best piece of career advice?

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An interview with Marc Randolph how his family influenced him growing up, how to craft a compelling business pitch, how to overcome rejection, his relationship with his Netflix partner Reid Hastings and his best career advice.

Welcome to the 53rd episode of 5 Questions with Dan Schawbel. As your host, my goal is to curate the best advice from the world’s smartest and most interesting people by asking them just 5 questions.

This episodes guest:

My guest today is the co-founder and first CEO of Netflix, Marc Randolph. Born in Chappaqua, New York, Marc’s father was a nuclear engineer, his paternal great-granduncle was psychoanalysis pioneer Sigmund Freud and his paternal great-uncle was PR legend Edward Bernays. After he graduated college in 1981, he began working at Cherry Lane Music Company based in New York and was in charge of the small mail-order operation. It was there where he learned marketing techniques, how to sell music directly to customers and used technology to track buying behavior. Marc continued to gain experience building direct-to-consumer marketing operations at Borland, then at various Silicon Valley start-ups, before becoming a founder of Integrity QA. A year later, Pura Atria acquired his startup and CEO Reed Hastings retained Marc as VP of Corporate Marketing. Later that year, Rational Software acquired Pura Atria for $850 million. Marc and Reed decided to join forces to launch Netflix in 1998, with Marc as the first CEO. Today, Netflix has over 150 million paid subscribers worldwide watching over a billion hours of video content each week with $15.8 billion in revenue annually. I sat down with Marc to learn more about his fascinating background, hear stories from his new book “That Will Never Work” and get advice on everything from pitching an idea to overcoming criticism.

Video interview from New York City:

The 5 questions questions I ask in this episode:

  1. You come from a family of overachievers and pioneers. How did they influence you growing up?
  2. What makes a good pitch to influence others to buy into you as a person or your business idea?
  3. Early in my career, a lot of people said, “that will never work”. People didn’t believe in me early on. What does it take to overcome that resistance and continue to follow your path?
  4. Different from your business partner Reid Hastings, you’ve been more behind the scenes. Where does your humility come from?
  5. What is your best piece of career advice?

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