5 Questions With Dan Schawbel

An interview with Gary Vaynerchuk, CEO of Vaynermedia, about what’s changed for him, what the fine line is between hustle and burnout, his responsibility as a leader, how people can be empathetic and how to find positive people to surround yourself with. Welcome to the eighteenth 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 Gary Vaynerchuk, the chairman of VaynerX, CEO of Vaynermedia, an angel investor and a bestselling author. Born in Belarus, Gary immigrated to the United States with his family in 1978 at the age of three. He lived in a studio apartment in Queens, New York with eight other family members, eventually moving to Edison New Jersey. There, he started his entrepreneurial journey by operating a lemonade-stand franchise, while selling baseball cards on weekends. At age 14, he joined his fathers wine business, renaming it Wine Library. Then in 1998, he launched Wine Library TV, a daily webcast covering wine, while growing the wine business from $3 to $60 million using email marketing, traditional advertising and Google AdWords. Then, in 2009 he launched VaynerMedia, a digital ad agency with clients including GE, Unilever, Chase and PepsiCo. Since then, he’s launched several other ventures, including The Gallery, which combines his acquisition of the media properties PureWow and ONE37pm, in addition to athlete representation company VaynerSports, and his latest serving small businesses, The Sasha Group, named after his father. Gary is the bestselling author of 6 books, including the classic Crush It!, and has invested in Facebook, Twitter, Tumblr and dozens of other startups. This is my 4th interview with Gary in the past decade and the first one to be featured on his daily documentary series on YouTube called #DailyVee (episode #504). Video interview from New York City: The 5 questions questions I ask in this episode: What’s changed for you and what’s remained the same? What is the fine line between hustle and burnout? What responsibility do you have as a leader with a platform? How can people be more empathetic at work and at home? How do you find positive people to surround yourself with? Follow Gary’s journey: Company Books Blog Podcast Instagram Facebook YouTube Twitter LinkedIn

An interview with Rachel Hollis, author of Girl, Wash Your Face, about how she has the courage to share her personal life publicly, how she lives fearlessly, how to take charge of your life, who motivates her and her best career advice. Welcome to the seventeenth 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: Rachel Hollis was born in Weedpatch, California and after graduating high school, moved to LA where an obsession with Matt Damon led her to apply for (and get) a job at Miramax. While there, she met her husband and founded an event-planning company, Chic Events. Then in 2015, Rachel had her breakthrough moment on social media when an Instagram photo of her celebrating her stretch marks went viral to over 10 million views. In 2018, her book Girl, Wash Your Face deputed and went onto being a #1 New York Times bestseller for twelve weeks selling more than 880,000 copies in the United States alone. Since the success of her book, Hollis, her husband Dave and four children have moved outside of Austin, Texas. Her follow up book is called Girl, Stop Apologizing. With her husband she is the co-host of the RISE Together podcast and co-founders of The Hollis Company. The company has media, products, inspiration and community to arm people with the tools they need to make positive and lasting change in their lives. For her hard work, dedication and business success, Rachel was named by Inc. Magazine as one of the “Top 30 Entrepreneurs under 30”. Both Rachel and I started out as bloggers before we were entrepreneurs and authors. I deeply respect her ability to talk about her biggest insecurities and flaws publicly. The 5 questions questions I ask in this episode: How did you originally get the courage to share your personal life publicly? What does it mean to live fearlessly? How can people stop feeling shame and start taking charge of their lives? Who do you look to for inspiration, motivation and emotional support? What is your best piece of career advice? Follow Rachel’s journey: Company Books Blog Podcast Instagram Facebook YouTube Twitter

An interview with Simon Sinek, author of Start With Why, about what’s changed for him since he started, the skills that are important in the machine age, who he would give voice to, how he remains optimistic and his best career advice. Welcome to the sixteenth 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:   Simon Sinek is the author of Start With Why, The Infinite Game and other bestsellers. Born in Wimbledon, London, Sinek grew up in Johannesburg, South Africa, London, and Hong Kong before settling in the United States. He graduating from Northern Valley Regional High School at Demarest in 1991, studied law at London’s City University, and then graduated Brandeis University with a Bachelor of Arts (BA) in cultural anthropology. Simon began his career at two well-known New York ad agencies: Euro RSCG and Ogilvy. Simon went on to speak at a TEDx Puget Sound in South Dakota back in 2009. The video went on to generate over 40 million views, subtitled in 47 languages, and is the third most watched TED Talk ever. With the success of the TEDx Talk, he went on to write the million-copy bestseller Start With Why, and then followed up with other bestsellers including Leaders Eat Last, Together Is Better and Find Your Why. His upcoming book is called The Infinite Game. This is my fourth interview with Simon since 2010 and I always enjoy his thoughts on all aspects of leadership, the workplace and culture. Video interview from New York City: The 5 questions questions I ask in this episode: This is our 4th conversation since your first book, Start with Why, came out. What’s most changed in how you view the world and what’s remained the same? What skills do you think will become more important in the coming age of machines? Who would you give voice to that has impacted your life? How do you remain optimistic despite the negativity around you? What is your best piece of career advice? Follow Simon’s journey: TED Profile Website Instagram Twitter Facebook LinkedIn YouTube

An interview with Chris Anderson, the head of TED, about how he keeps the TED brand fresh, what keeps him motivated, how he selects people and ideas, and which TED ideas have changed society the most. Welcome to the fifteenth 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: Chris Anderson was born in Pakistan. He studied at Woodstock School in India before moving to Monkton Combe School in England. At the University of Oxford, he studied physics, then changed to philosophy, politics and economics, graduating in 1978. Then in 1984, he was captivated by the home-computer revolution and became an editor at two of the UK’s early computer magazines, Personal Computer Games and Zzap! A year later he founded Future Publishing with a $25,000 bank loan. In 1994, Anderson moved to the United States where he built Imagine Media, publisher of Business 2.0 magazine and creator of the popular video game users website IGN, which expanded to publishing 150 magazines and websites with 2,000 employees. This success allowed Anderson to create a private nonprofit organization, the Sapling Foundation, which eventually acquired the TED Conference in 2001. Since then, the TED Conference has become one of the most prestigious stages in the world, and through the TEDx initiative over 100,000 TED Talks have been published online generating billions of views. Chris is the New York Times bestselling author of TED Talks and host of “The TED Interview”, a podcast where he speaks with some of the world’s most interesting people to dig into the provocative and powerful ideas of our time. Video interview from New York City: The 5 questions questions I ask in this episode: Over 100,000 TED and TEDx talks have been published. How do you keep the brand fresh and continue to get people interested in watching and spreading ideas? What keeps you motivated and inspired to continue to help spread ideas through the TED platform? What does the future hold? Has your process for selecting people, and their ideas changed over the years? What’s remained consistent? Which TED ideas have changed the way you work and live and why? Have any ideas shared on the TED stage turned into real life changes in society or companies? Follow Chris’s journey: The TED Interview Podcast TED Profile Twitter

An interview with Ana Kasparian, co-host of The Young Turks, about how she found her voice before entering the media world, how she deals with criticism, staying positive, preventing burnout and her responsibility as a leader. Welcome to the fourteenth 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: Ana Kasparian was born in Los Angeles California. She is the daughter of Armenian immigrant parents and learned how to speak English as a second language after watching Sesame Street. Ana was a performer in her childhood dancing ballet from 3 to 19 years old. She completed her Bachelor of Arts Degree in Journalism and a Masters Degree in Political Science at California State University Northridge. After graduating, she became an assistant producer with CBS Radio news stations in Los Angeles. In 2007, after stints at AOL News, YouTube, TidalTv and On Point, Ana became the producer and co-host with Cenk Uygur of The Young Turks, a progressive news and commentary program on YouTube with over 4 million subscribers and over 34,000 videos. She’s been recognized on the Forbes 30 Under 30 list and has won several awards including a Webby for Best Web Personality and Host, and a Streamy Award for Best News and Culture Show. She’s been teaching broadcast journalism at her alma mater and speaks at many universities, conferences and political events. The 5 questions questions I ask in this episode: Where did you originally find your voice before entering the media world? How do you have the courage to put yourself out there despite criticism? How do you stay positive despite all the negativity around you? How do you prevent yourself from being burned out? What is your responsibility as a leader for our generation? Follow Ana’s journey: The Young Turks Twitter Instagram Facebook

An interview with Seth Godin, bestselling author and speaker, about what he’s learned in his career, the importance of empathy, where his ideas come from, how to build connection and his best career advice. Welcome to the thirteenth 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: Seth Godin was born in Mount Vernon, New York, where he worked at Spinnaker Software until 1986. Using the $20,000 in savings from that job, he founded Seth Godin Productions, a book packaging company out of his studio apartment in New York City. From there, he met entrepreneur Mark Hurst to create Yoyodyne, which used contests, online games and scavenger hunts to market companies to users. After selling his packaging business, and focusing on Yoyodyne full-time until it was acquired for about $30 million by Yahoo! in 1998. Godin continued his entrepreneurial journey with Squidoo in 2006. It became one of the 500 most viewed sites in the world and Godin sold it in 2014 to HubPages. Over the course of his career, he’s written 18 books, thousands of blog posts and countless keynote speeches around the world. Some of his most famous books include Permission Marketing, Purple Cow, Tribes and Linchpin. His new book is called This is Marketing: You Can’t Be Seen Until You Learn to See. After years of winning the hearts and minds of the entire marketing industry, he was inducted into the American Marketing Association’s Marketing Hall of Fame. This is my fourth interview with Godin over the past eight years and I continue to be impressed by his perspectives, his approach to storytelling and he stays on-brand. The 5 questions questions I ask in this episode: What has 25 years of experience in marketing taught you about yourself, other people and the world we live in? In today’s society, why is empathy an important quality for leaders and marketers alike? As someone who has published thousands of blog posts, and written numerous books, where do your new ideas come from? How do we use technology as a bridge to human connection instead of a barrier? What is your best career advice? Follow Seth’s journey: Blog Books Podcast Facebook

An interview with Rachael Ray, the Daytime Emmy Award Winning TV show host of Rachael Ray, about her biggest influences, her business, being self-made, her first job and her best career advice. Welcome to the twelfth 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: Rachael Ray is a Daytime Emmy Award Winning TV show host. Raised in Glens Falls, New York, Rachael witnessed her mother managing restaurants. In 1995, she moved to New York City to work her first job at the Macy’s Marketplace candy counter. She left Macy’s to work at Agata & Valentina, a specialty foods store, and then eventually moved back to upstate New York to manage Mister Brown’s Pub in a hotel. Then, she became a buyer at Cowan & Lobel, a gourmet market, which inspired her 30 Minute Meals. The success of her 30 Minute Meals classes led to a weekly local TV segment, then a public radio broadcast and her first book. From there, she was on NBC’s The Today Show, which led to her first Food Network contract in 2001. Today, she hosts the syndicated daily talk and lifestyle program Rachael Ray, and the Food Network series 30 Minute Meals, Rachael Ray’s Tasty Travels and $40 a Day. She also founded the Every Day with Rachael Ray magazine and has written countless cookbooks, including Everyone is Italian on Sunday, Comfort Foods, Week in a Day and My Year in Meals. The 5 questions questions I ask in this episode: Who has most influenced your career and why? What do people not know about you and your business? What has surprised you the most about being successful? What did you learn from your first job at Macy’s? What is your best career advice? Follow Rachael’s journey: Facebook Instagram Twitter Books TV Show Magazine

An interview with Jocko Willink, a former U.S. Navy Seal, the host of the Jocko Podcast and author of multiple #1 New York Times bestsellers, about the biggest leadership lesson he learned, how to lead in change, why leaders have to be followers, the dichotomy of leadership and his best advice. Welcome to the eleventh 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: Jocko Willink is a Former U.S. Navy Seal, the Host of the Jocko Podcast and author of multiple #1 New York Times bestsellers. Born and raised in New England, Jocko enlisted in the U.S. Navy in 1990. He served eight years on active duty, as an enlisted Navy SEAL with SEAL Team ONE and SEAL Team TWO. Willink was part of the SEAL team that seized Russian Tanker Volga-Neft-147 in the Gulf of Oman which was carrying Iraqi oil in violation of a U.N. economic embargo. Willink earned his commission at the Officer Candidate School and eventually served as a platoon commander. He completed multiple deployments to Asia, the Middle East and Europe. During Operation Iraqi Freedom he deployed to the Iraqi town of Ramadi in 2006 with SEAL Team THREE as commander of Task Unit Bruiser. Willink also served as a Navy SEAL instructor during his career. He retired in October 2010 after 20 years of service. Today, he is the host of the Jocko Podcast, which receives two million downloads per episode and is the author of multiple bestsellers, including Extreme Ownership, Discipline Equals Freedom and his latest book The Dichotomy of Leadership. The 5 questions questions I ask in this episode: What is the biggest leadership lesson you learned as a U.S. Navy Seal? How can leaders best prepare their teams for change? Why do good leaders have to also be good followers? How can a leader be aggressive yet prudent and empathetic? What is your best piece of career advice? Follow Jocko’s journey: Facebook YouTube Instagram Twitter Books Podcast

An interview with Steve Harvey, host of the syndicated talk show “Steve”, the morning radio show “The Steve Harvey Morning Show” and Family Feud, about how he overcame his biggest struggle, how to handle fear, his daily routines, letting go of negative people and what’s most important to him in life. Welcome to the tenth 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: Steve Harvey was raised in Welch, West Virginia. Some of his original jobs growing up were a boxer, an autoworker, an insurance salesman, a carpet cleaner and a mailman. In 1990, he was a finalist in the Second Annual Johnnie Walker National Comedy Search, which led him to being the host of “Showtime at the Apollo”. In 1994, his success as a stand-up comedian led to a starring role on ABC Show “Me and the Boys”. From 1996 to 2002 he stared in The Steve Harvey Show on the WB Network. At the same time, he worked as a stand-up comedian performing on the King of Comedy Tour with Bernie Mac, Cedric the Entertainer and D.L. Hughley. In 2010, he become the host of his morning radio show and at the same time began hosting Family Feud and then Celebrity Family Feud. More recently, he became the host of Steve. In the past several years, he’s written multiple bestselling books including Straight Talk, No Chaser, Act Like a Success, Think Like a Success, Act Like a Lady, Think Like a Man and Jump. He is a six-time Daytime Emmy Award winner, two-time Marconi Award winner, and a 14-time NAACP Image Award winner in various categories. The 5 questions questions I ask in this episode: Tell us the story of a major obstacle in your life, how you overcame it, and how it’s helped you become who you are today. How do people not let the fear of failure get in their own way of a successful life? What are some of your daily routines that have made you more energized and happy? How do we let go of the people in our lives that are doing us harm instead of supporting our ambitions? But what role does faith, religion and family play in pushing through you know some of life’s greatest challenges? Follow Steve’s journey: Facebook YouTube Twitter Website Books

An interview with Tony Hawk, a legendary skateboarder and entrepreneur, about what keeps him motivated, how he makes time for his children, when he recognized his potential, the legacy he wants to leave and his best career advice. Welcome to the ninth 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: Tony Hawk was raised in San Diego, California. He was described as hyperactive growing up, which is how I was also described. He was gifted with a high IQ and took advanced classes in school. At age 14 he became a professional skateboarder and eventually went on to be the National Skateboard Association world champion for twelve consecutive years. Aside from his career as a pro skateboarder, he’s known for his hit video game series “Tony Hawk’s Pro Skater”, which debuted in 1999 and has produced 18 titles to date. Throughout his career, Hawk has made numerous appearances in films like Jackass: The Movie, Escape from L.A. and The New Guy. He is the founder of the Tony Hawk Foundation, which has given away over $5.8 billion for the development of almost 600 skate parks in low-income areas in the US. Hawk is also the owner of 900 Films and the RIDE Channel on YouTube. He’s been instrumental in getting skateboarding into the 2020 Olympics, which was a big deal for the sport. The 5 questions questions I ask in this episode: What keeps you motivated after your multi-decade career? How have you been able to live your dream career, while still making time for your family? At what point in your life did you recognize your potential? What legacy do you want to leave in both the skating and business world? What is your best piece of career advice? Follow Tony’s journey: RIDE Channel on YouTube 900 Films Tony Hawk Foundation Facebook Instagram Twitter Website