

5 Questions With Dan Schawbel
Dan Schawbel, #1 Bestselling Author, Speaker, Entrepreneur
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.
Episodes
Mentioned books

Apr 29, 2019 • 7min
Episode 28: Killer Mike
An interview with Killer Mike on what he would change about American politics, where his entrepreneurial spirit comes from, how he weaves political messages into his content, how he manages a company while being a good parent and his best career advice.
Welcome to the 28th 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 rapper and political activist Killer Mike. Born Michael Santiago Render in Atlanta Georgia, he was the son of a policeman father and florist mother. In 1995, while attending Morehouse College, he met the producers The Beat Bullies and Big Boi of OutKast. His music debut was on OutKast’s 2000 album Stankonia with the song “Snappin’ & Trappin” and later was part of their single collaboration “The Whole World”, which won the Grammy Award for “Best Rap Performance by a Duo or Group”. After being featured on Jay-Z’s album “The Blueprint 2”, he released his own album “Monster” with the hit single “A.D.I.D.A.S.” He has released other albums including two “I Pledge Allegiance to the Grind” albums, PL3DGE and R.A.P. Music. He’s been featured in films including Aqua Teen Hunger Force, Baby Driver, South Park and is the host of Trigger Warning with Killer Mike on Netflix. Killer Mike opened a barbershop called Graffitis SWAG Barbershop in Atlanta, with artwork honoring historical black leaders like Martin Luther King, Jr. He’s been a social and political activist on topics like social equality, police brutality and racism.
The 5 questions questions I ask in this episode:
If you could change only one thing about American politics, what would it be and why?
Where does your entrepreneurial spirit come from?
How do you weave in your social and political messages into your music and Netflix show?
How do you manage being a husband, father of 4 and business owner at once?
What’s your best piece of career advice?
Follow Mike’s journey:
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Netflix Show
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Apr 22, 2019 • 8min
Episode 27: Carly Fiorina
An interview with Carly Fiorina on why you should find a path instead of create a plan, how her childhood impacted her path, what to do if you’re stuck, what men can learn from women about leadership and her best career advice.
Welcome to the 27th 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 former CEO of HP and former U.S. Presidential Candidate, Carly Fiorina. Born in Austin, Texas to a mother who was an abstract painter and father who had a variety of jobs including professor, University dean, Deputy U.S. Attorney General and judge. She frequently moved in her childhood, living in London, Ghana and North Carolina. Carly studied philosophy and medieval history at Stanford University, while working as a secretary during the summers. While originally aspiring to be a pianist, she attended and eventually dropped out of law school. Carly ended up getting an MBA from the Robert H. Smith School of Business at the University of Maryland and a Masters at MIT’s Sloan School of Management. In 1980, she started as a AT&T management trainee and eventually became the company’s first female officer as SVP and then led its North American operations. In 1995, she led corporate operations for Lucent Technologies, playing a key role in an IPO, and then was named group President for their global service-provider business. In 1998, Fortune Magazine named Fiorina as “The Most Powerful Woman in American Business.” From 1999 to 2005, she was the CEO of HP. Since leaving HP, she has served as chairman of Good360, the world’s largest product philanthropy organization, as chairman of Opportunity International, a Christian-based organization that lifts millions out of poverty around the globe through microfinance and chair and CEO of the Fiorina Foundation that donates to a variety of important causes. Fiorina ran for the United States Senate in 2010 and the Republican presidential nomination in 2016. Her new book is called Find Your Way: Unleash Your Power and Highest Potential.
Video interview from New York City:
The 5 questions questions I ask in this episode:
Why should you find a path instead of stick to a plan?
How did moving around a lot growing up affect your path?
What’s the first thing you should do if you’re stuck?
What can men learn from women about leadership?
What’s your best piece of career advice?
Follow Carly’s journey:
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Apr 15, 2019 • 8min
Episode 26: Stuart Weitzman
An interview with Stuart Weitzman about why he decided to pursue his career, the process of developing a new shoe, how he stays relevant, stands out in his industry and his best career advice.
Welcome to the 26th 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 fashion designer and founder of the Stuart Weitzman shoe company, Stuart Weitzman. Born in Haverhill, Massachusetts, he worked with his older brother at his fathers shoe factory called Seymour Shoes. Stuart designed shoes for his fathers business from the late 1950s to the early 1960s. In 1958, he graduated from George W. Hewlett High School and in 1963; he attended the University of Pennsylvania’s Wharton School. When his father died, he and his brother took charge of the business, sold it to a Spanish company and eventually purchased it back. Stuart was known for, and got attention from, the use of unconventional and unique materials like vinyl, cork, wallpaper and gold, as well as his objective to produce something flawless. He became famous for creating a “Million Dollar Shoe”, with 464 diamonds for Laura Harring who wore them to the 2002 Academy Awards. In 2015, Coach acquired the Stuart Weitzman Company for $574 million. Stuart stayed on as a shoe designer until retiring in 2017, but maintains his title as chairman emeritus. This year, the University of Pennsylvania announced that the School of Design will be renamed the University of Pennsylvania Stuart Weitzman School of design. I sat down with Stuart a few days before his keynote at the International Trademark Associations March Conference: The Business of Brands held in New York City on March 28th and 29th.
Video interview from New York City:
The 5 questions questions I ask in this episode:
Why did you decide to pursue this career?
What’s the process of developing a new shoe?
How do you stay on the latest trends and adapt to change?
How have you been able to stand out among other brands?
What’s your best piece of career advice?
Follow Stuart’s company:
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Apr 8, 2019 • 10min
Episode 25: Marianne Williamson
An interview with Marianne Williamson on how her spirituality influenced her to get into politics, overcoming insecurities, how to forgive someone, support mental illness and her best career advice.
Welcome to the 25th 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 spiritual leader, bestselling author, lecturer, activist and 2020 U.S. Presidential Candidate, Marianne Williamson. Born in Houston, Texas as the youngest of three children, she graduated from Houston’s Bellaire High School. She spent two years studying theater and philosophy at Pomona College in California. She dropped out of college during her junior year to move to New York City in pursuit of a career as a cabaret singer. After reading and being influenced by A Course in Miracles, a book about achieving spiritual transformation, she opened a bookstore and coffee shop back in Houston. Then, four years later she moved to LA to lecture on the book, eventually expanding to lecture internationally. Her first book, A Return to Love, was featured on The Oprah Winfrey Show, and has led to another dozen books, with millions of copies in print. Since then, she’s founded Project Angel Food, a food delivery program-serving people with AIDS and other illnesses and The Peace Alliance, that builds peace-building projects. Marianne continues to be a social and political activist as she campaigns to be the first female President of the United States in 2020. To go along with her campaign, she is releasing her new book, A Politics of Love.
The 5 questions questions I ask in this episode:
How has your spirituality, teaching and entrepreneurial spirit influenced you to get into politics?
How do we overcome our deepest fears and insecurities that get in the way of our fulfillment?
What’s the best way to forgive someone who has caused you pain?
What can we do to help support mental illness at work and at home?
What is your best piece of career advice?
Follow Marianne’s journey:
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Apr 2, 2019 • 10min
Episode 24: Marcus Buckingham
An interview with Marcus Buckingham on how to find your purpose, discover your strengths, why you should ask for helpful attention, the importance of a freethinking leader and his best career advice.
Welcome to the 24th 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 New York Times bestselling author and the leader of the strengths movement, Marcus Buckingham. Born in London, he grew up with a stutter leaving him unable to speak until age 13. He overcame it by pretending to speak to one person, instead of 300, when addressing boys at his prep school. He was educated at Pembroke College in Cambridge, graduating with a degree in Social and Political Sciences in 1987. In school, he was recruited by professor Donald Clifton, the founder of SRI, which was later acquired The Gallup Organization. There, Buckingham was part of a team that worked on a survey measuring factors that contribute to employee engagement. Based on this research, he wrote his first book, First , Break All the Rules, which went on to sell over a million copies. He followed up with Now, Discover Your Strengths and The One Thing You Need to Know before launching his own company, The Marcus Buckingham Company in 2006. Fast-forward to 2017 when ADP acquired the company and Buckingham became their Co-Head and Talent Expert. His latest book, that he co-authored with Cisco SVP Ashley Goodall, is called Nine Lies About Work: A Freethinking Leader’s Guide to the Real World.
I’ve known Marcus since the beginning of my career and this is my fourth interview with him since 2010. He was generous enough to write the foreword for my book, Promote Yourself, and his co-author Ashley is a client of mine who I’ve known since his days with Deloitte. It’s an honor to support them, this book and I value their advice.
The 5 questions questions I ask in this episode:
What’s the best way to find your purpose and align it to the right leaders and companies?
How can people discover their strengths and then use them to advance their careers and lives?
Why do you think we should give helpful attention instead of constant feedback?
What is a freethinking leader and why are they important in today’s workplace?
What is your best piece of career advice?
Follow Marcus’s journey:
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Mar 25, 2019 • 10min
Episode 23: Chris Hadfield
An interview with Chris Hadfield on why he became an astronaut, why he used social media in space, what it’s like being in space, what the most common astronaut myth is and his best advice.
Welcome to the 23rd 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 first Canadian astronaut to walk in space, Chris Hadfield. Born in Sarnia, Ontario, Hadfield was raised on a corn farm and became interested in flying at a young age and in being an astronaut at age nine when he saw the Apollo 11 Moon landing on television. He attended White Oaks Secondary School in Ontario until his senior year and then graduated as an Ontario Scholar from Milton District High School in 1977. After graduating from high school in 1978, he joined the Canadian Armed Forces and spent two years at Royal Roads Military College followed by two years at the Royal Military College. In 1983, he took honors as the top graduate from Basic Jet Training at CFB Moose Jaw and then went on to train as a tactical fighter pilot with 410 Tactical Fighter Operational Training Squadron. After completing his fighter training, Hadfield flew CF-18 Hornets with 425 Tactical Fighter Squadron, flying intercept missions for NORAD. In the late 1980s, Hadfield attended the US Air Force Test Pilot School at Edwards Air Force Base and served as an exchange officer with the US Navy at Strike Test Directorate. In May 1992, Hadfield graduated with a master’s degree in aviation systems from the University of Tennessee Space Institute. In total, Hadfield has flown over 70 different types of aircraft. Hadfield was selected to become one of four new Canadian astronauts from a field of 5,330 applicants in June 1992. Hadfield is a civilian CSA astronaut, having retired as a colonel from the Canadian Armed Forces in 2003 after 25 years of military service. He was Chief of Robotics for the NASA Astronaut Office at the Johnson Space Center in Houston, Texas from 2003–2006 and was Chief of International Space Station Operations from 2006–2008. NASA announced in 2010 that Hadfield would become the first Canadian commander of the International Space Station, leading Expedition 35 after its launch on December 19, 2012. In June 2013, he retired and wrote his autobiography entitled “An Astronaut’s Guide to Life on Earth”.
The 5 questions questions I ask in this episode:
Why did you become an astronaut in the first place, and what did you originally want to accomplish by doing that?
You’re known for your use of Twitter and Facebook in space. What made you decide to use these tools, and how did it affect your life and the people around you?
What is it like being in space?
What is one thing that people don’t know about you and astronauts in general that would surprise them?
What are your top three tips for anyone who wants to achieve extraordinary goals like you?
Follow Chris’s journey:
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Mar 18, 2019 • 10min
Episode 22: Tom Peters
An interview with Tom Peters why listening is an important leadership quality, how he’s been impacted by his parents, how leaders can support mental health, his legacy and best career advice.
Welcome to the 22nd 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 legendary business author, Tom Peters. Born in Baltimore, Maryland, Tom went to high school at Severn, attended college at Cornell University with a degree in civil engineering and then graduated with his masters in 1966. Between 1966 and 1970, he served in the U.S. Navy, making two deployments in Vietnam. After leaving the Navy, he studied business at the Stanford Business School for his MBA, followed by a PhD in organizational behavior in 1977. The title of his dissertation was “Patterns of Winning and Losing: Effects on Approach and Avoidance by Friends and Enemies.” While enrolled in the PhD, he also worked as a management consultant at McKinsey & Company, eventually becoming a partner and Organization Effectiveness practice leader in 1979. Two years later he left McKinsey and became an independent consultant. It was then, when he wrote In Search of Excellence, which has been said to have created the business book industry, selling over 3 million copies from 1982 to 1986, and was followed up with a series of PBS specials based on it and hosted by Tom. Over the last 38 years Peters calculates that he has made 2,500 speeches in 50 American states and 67 countries to over 5 million people. Along the way he has made 7,500 flights covering 5 million miles. In 2017, the Thinkers50 awarded Peters with its Lifetime Achievement Award for his paving the way for the ‘thought leadership’ and ‘business book industries’. His 17 books have sold more than 10 million copies. Last year, he released his latest book, The Excellence Dividend: Meeting the Tech Tide with Work That Wows and Jobs That Last.
The 5 questions questions I ask in this episode:
Why is “listening” such an important leadership quality?
How have you been impacted by those closest to you?
What can leaders do to support mental health at work?
What do you want your legacy to be?
What is your best piece of career advice?
Follow Gretchen’s journey:
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Blog
Books
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LinkedIn

Mar 5, 2019 • 10min
Episode 21: Gretchen Rubin
An interview with Gretchen Rubin about what’s changed for her over the years, how she invests her time, how to stand out in today’s noisy world, how outer order affects inner calm and her best career advice.
Welcome to the 21st 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 #1 New York Times bestselling author, podcast host and speaker, Gretchen Rubin. Born in Kansas City, Missouri to a father who was a lawyer. She decided to pursue the same career, receiving both her undergraduate and law degrees from Yale University. At Yale, she was the editor-in-chief of the Yale Law Journal and won the Edgar M. Cullen Prize. After graduating, she clerked for Judge Pierre N. Leval of the U.S. Court of Appeals for the Second Circuit, and then on the U.S. Supreme Court for Justice Sandra Day O’Connor. After her clerkships, she served as a chief adviser to Federal Communications Commission Chairman Reed Hundt. Then, she went on to write two biographies, Forty Ways to Look at Winston Churchill and Forty Ways to Look at JFK. Then, she wrote Power Money Fame Sex: A User’s Guide, which parodied self-help books by analyzing and exposing the techniques used to exploit those who strive for those worldly ambitions. She then went on to write a series of self-help books focusing on happiness, habits and human nature, including The Happiness Project, Better Than Before, The Four Tendencies and her latest, Outer Order, Inner Calm. Combined, her books have sold more than 3.5 million copies and have been translated into more than 30 languages. Gretchen teamed up with her sister, who is also a writer, to co-host the Happier with Gretchen Rubin podcast and Gretchen continues to write on her personal blog at GretchenRubin.com. I’ve known Gretchen for over a decade, right before her book, The Happiness Project, became a global phenomenon. We’ve kept in touch and shared insights into the publishing and media world and I’ve continued to be impressed by her openness to learning new strategies and her generosity towards up-and-coming authors.
Video interview from New York City:
The 5 questions questions I ask in this episode:
We’ve known each other for at decade. What’s changed about your work and how you see the world and what’s remained the same?
How do you know where to invest your time?
How do you stand out as a professional in today’s world?
How does outer order affect inner calm?
What is your best piece of career advice?
Follow Gretchen’s journey:
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Feb 19, 2019 • 8min
Episode 20: General Stanley McChrystal
An interview with General Stanley McChrystal about the biggest leadership myth, how leadership has changed, the most common leadership traits, why environment matters and his best piece of career advice.
Welcome to the twentieth 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 former four-star U.S. Army General Stanley McChrystal. Born in Fort Leavenworth, Kansas, Stanley came from a line of military leaders, including his father who was a Major General and a grandfather who was a Colonel. He graduated from the United States Military Academy at West Point in 1976 and was commissioned a second lieutenant in the U.S. Army. That year, his initial assignment was to C Company, 1st Battalion, 504th Parachute Infantry Regiment, 82nd Airborne Division, serving as a weapons platoon leader. Two years later, he enrolled as a student in the Special Forces Officer Course at the Special Forces School at Fort Bragg, North Carolina. Then in 1981, he moved to South Korea as intelligence and operations officer for the United Nations Command Support Group and then became battalion operations officer. In 1990, he became action officer for Army Special Operations, working in Joint Special Operations Command, then a year later he saw action in the Desert Shield and Desert Storm tours. He was commander of the Joint Special Operations Command from 2003 to 2008 and became the top commander in Afghanistan in 2009, eventually resigning in 2010. McChrystal was awarded the Distinguished Service Medal and the Defense Distinguished Service Medal. Since his resignation, he has taught courses in international relations at Yale University, started his own company called The McChrystal Group, an elite advisory services & leadership development firm, and authored of multiple bestsellers including Team of Teams and Leaders: Myth and Reality. Stanley is on both Jet Blue and Navistar International’s board of directors and Chairman of the Board of Siemens Government Technologies.
The 5 questions questions I ask in this episode:
What is the biggest leadership myth?
How do you believe leadership has changed over the years and what’s stayed the same?
What common leadership traits do YOU share with those you interviewed for the book?
Why do different leaders require different environments?
What is your best piece of career advice?
Follow Stanley’s journey:
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Feb 10, 2019 • 7min
Episode 19: Diane von Furstenberg
An interview with Diane von Furstenberg about being a woman in today’s workplace, how she overcame early career obstacles, who influenced her, how she’s expanded her business and what she’s looking for when hiring.
Welcome to the nineteenth 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 Belgian fashion designer and founder of DVF, Diane von Furstenberg. Born in Brussels in 1946, she initially rose to prominence after marrying German Catholic Prince Egon von Fürstenberg. Following their separation in 1973 and subsequent divorce in 1983, she continued to use his family name. After moving to New York, she met Vogue editor Diana Vreeland, who admired her clothing designs, giving her the confidence to be listed in New York Fashion Week, which launched her business. A year later, she introduced the knitted jersey “wrap dress”, which became popular and had a big influence on women’s fashion. After the success of the wrap dress, Furstenberg was featured on the cover of Newsweek magazine in 1976 and her annual retail sales grew to $150 million. Then in 1985, she moved to Paris, where she founded Salvy, a French-language publishing house. There she started a number of other businesses including a line of cosmetics and a home-shopping business. In 2006, she was elected as president of the Council of Fashion Designers of America, a position she still holds. Since then, she’s expanded DVF to over 70 countries, 45 shops worldwide and over $500 million in annual sales. Her clothes have been worn by many celebrities including, Gwyneth Paltrow, Madonna, Jessica Alba and Jennifer Lopez. In 2014, she was listed as the 68th most powerful woman in the world by Forbes and in 2015, she was included in the TIME 100. She’s the author of Diane and The Woman I Wanted to Be. I caught up with Diane back in 2015, where we both spoke at the first annual Lead On Watermark Silicon Valley Conference for Women.
The 5 questions questions I ask in this episode:
What do most men not understand about being a woman in today’s workplace?
What were some of your early career struggles and how did you overcome them?
Who were some of your greatest influences growing up and what did you learn from them?
What new challenges and opportunities are created as you’ve expanded your business?
What hard and soft skills are you looking for when you hire and how can an employee impress you after they get the job?
Follow Diane’s journey:
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