An interview with Debra Messing about how her parents supported her career, how she’s challenged the status quo, staying positive in the face of adversity, the global health crisis, and her best career advice. Welcome to the 88th 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 star of Will & Grace, Debra Messing. Born in Brooklyn, New York, her family moved to Rhode Island to attend high school, where she acted and sang in musicals. Before pursuing her acting career, she was urged by her parents to attend college at Brandeis University. Upon graduating with honors, she attended New York University’s Tisch School of the Arts. After appearing in the film A Walk in the Clouds, she was chosen as a co-star for the TV sitcom Ned & Stacey, which led to roles in other shows like Seinfeld and Prey. In 1998, she co-starred as Grace Adler in mega TV hit show Will & Grace. The success of the show led to other roles in movies like Along Came Polly, The Wedding Date, and the remake of Dirty Dancing. More recently, Debra reprised her role in the revival of Will & Grace with a ninth Golden Globe nomination and is the co-host of The Dissenters Podcast. I had the pleasure of speaking with her about the impact of Will & Grace on the gay community, which is timely since the Supreme Court just ruled that workers can’ be fired for being gay or transgender. The 5 questions I ask in this episode: Part of why I was able to pursue my career path as an author, podcaster, and researcher was the support of my parents. How important were your parents encouraged you to pursue your dream of becoming an actress and what advice did they give you during your pursuit? Your new podcast The Dissenters features nonconformists like Glennon Doyle who was recently on this podcast. In what way have you challenged the status quo and what inspires you about others who have done the same? You said that acting is 90% confidence. As both a social activist and actress, you’ve faced criticism, rejection, and obstacles. How do you stay positive, confident, and motivated in the face of adversity? How has your involvement and activism around HIV and Aids in Africa shaped your understanding of the global health crisis we are dealing with today? What is your best piece of career advice? Follow Debra’s journey: PodcastTwitterFacebookInstagram

An interview with Patrick McGinnis about starting a side business while working full-time, how to start a business, prevent FOMO from affecting our daily lives and his best career advice. Welcome to the 87th 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 author and venture capitalist, Patrick McGinnis. Born in Sanford, Maine, Patrick coined the term FOMO, or “fear of missing out”, while studying at Harvard Business School back in 2004. Six years later, he founded Dirigo Advisors working with investors and fast-growing companies in Latin America, Europe, Africa, Asia and America. Then, went on to work at AIG Capital Partners before writing his first book entitled “The 10% Entrepreneur”. In 2018, Patrick released the first episode of the FOMO Sapiens Podcast, and I was recently featured this April to talk about working from home and corporate culture. The success of the podcast led to his TEDx talk in 2019 and his new book, “Fear of Missing Out”. As a fellow entrepreneur, I was curious to hear about Patrick’s perspectives on what we should all be mindful of before we start a business. The 5 questions I ask in this episode: I was a part-time entrepreneur from 2006 to 2010, sacrificing nights and weekends outside of my big corporate job to work on projects that I was passionate about. I had no idea that eventually those passions, and the hard work, would turn into a full-time job. How do you know if you can make it on your own versus staying at your company? If you do start a business outside of your full-time job, what’s the best way to meet the demands of both without being burned out? Can you share some tips for people who have great business ideas, but don’t know how to start them and fear failure? How can we prevent FOMO from affecting our daily decisions and instead focus on activities that bring us meaning and purpose? What is your best piece of career advice? Follow Meg’s journey: WebsiteBooksTwitterFacebookLinkedInInstagram

An interview with Meg Whitman about the difference between leading a Fortune 500 company and a startup, how to decide what risks are worth taking, what she learned from politics, how to manage during a crisis, and her best career advice. Welcome to the 86th 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 CEO of Quibi, Meg Whitman. Born in Cold Spring Harbor, New York, Meg graduated high school in three years in the top ten of her class. She originally wanted to be a doctor but ended up studying math and science at Princeton University, but later changed paths after spending a summer selling magazine advertisements. Meg went on to obtain her MBA from Harvard Business School and starting her professional career at Proctor & Gamble. From there, she worked as a consultant at Bain & Company eventually becoming a Senior Vice President before leaving to become an executive at Disney, Stride Right, and Hasbro. From 1998 to 2008, Meg was the CEO of eBay growing the company from 30 employees and $4 million in revenue to more than 15,000 employees and $8 million in revenue. Then in 2009 she ran for Governor of California later dropping out in 2010. A year later, Meg went back into the corporate world as the CEO of HP before stepping down in 2017. Then in 2018, she became the CEO of Quibi, a short-form original mobile-only platform. I’ve wanted to speak with Meg for years because of her breadth of experience, both in politics and at different companies, has fascinated me. The 5 questions I ask in this episode: You’ve been the CEO of two Fortune 500 companies and are now the CEO of a startup. What do you find are the differences, similarities, opportunities, and obstacles between being a CEO at a large versus a small company and how did your prior positions prepare you for this new role?You’re a believer in the importance of risk-taking and while you’ve received a lot of support for Quibi, most startups don’t succeed. How do you decide what risks are worth taking? What did you learn from the experience of running for Governor of California that helped you become a better business leader and what did you learn from your business career that made you a better politician? The workplace has changed so much since you started your career and is currently going through another transformation amidst the Covid-19 pandemic. What should leaders do to effectively manage their workforce during this crisis and how do you think the workplace will be transformed in the aftermath? What is your best piece of career advice? Follow Meg’s journey: CompanyTwitterFacebookLinkedIn

An interview with Andrew Yang about how he created a political movement, how Universal Basic Income can enable people to follow their passion, how to prepare for the future of work, his decision making on the campaign trail, and his best career advice. Welcome to the 85th 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 U.S. Presidential candidate, Andrew Yang. Born in Schenectady, New York, Yang was bullied growing up as one of the few Asians in his hometown of Westchester. He was a gifted child skipping a grade, attending the Center for Talented Youth at Johns Hopkins University, and then attended elite boarding school. Yang majored in economics and political science at Brown University and has a law degree from Columbia. His first job was as a corporate attorney, but eventually quit to launch his first startup, Stargiving that eventually failed during the dot-com bubble. From there, he became the CEO of Manhattan Prep, a test prep company, which was acquired in 2009. Yang then started the non-profit fellowship program Venture for America. In 2017, he launched his presidential campaign but later dropped out to endorse Joe Biden. Yang’s new non-profit is called Humanity Forward, which is dedicated to continuing his UBI and data security movements. More recently, he launched his podcast “Yang Speakers” and a few UBI experiments. Since I focus on employment topics and issues, I was excited to hear Yang’s perspectives on the future of work and careers. The 5 questions I ask in this episode: You started off as a political unknown, yet you were able to create and grow a movement with legions of supporters who call themselves “the yang gang”. What do you think were the key elements in your ability to start the movement, rapidly scale it, and sustain it for so long?You’re credited with raising awareness for Universal Basic Income (UBI) and are now suggesting that all American’s should receive $2,000 each month during the pandemic. One of the hidden benefits of UBI that isn’t talked about is the leverage it gives citizens to make better career-related decisions. For instance, if you have a toxic manager, you’re more likely to leave that job if you have a UBI safety net. Can you please explain how UBI can be a game-changer for a citizen’s career prospects?While many people think that companies are less likely to invest in automation during a crisis, the opposite is true. When revenues decline the cost of labor increases and a study by EY found that over 40% of companies are spending up plans to automate their businesses. You say the economy is going to become more “inhuman”. What can people do right now to prepare for the future of jobs and work?You’ve made some difficult decisions during your campaign. How did you evaluate when it was time to keep pushing forward, change paths, or quit while continuing to motivate your supporters? What would you have done differently if you ran again?What is your best piece of career advice? Follow Andrew’s journey: CompanyPodcastBooksTwitterInstagramFacebookYouTube

An interview with Jon Taffer about how entrepreneurs can build trust during a crisis, how his first job as a bartender made him empathetic, what successful relationships have in common, how he’s addressed his own excuses, and his best career advice. Welcome to the 84th 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 star of Bar Rescue, Jon Taffer. Born in Great Neck, New York, Jon first entered the restaurant industry in 1973 as a bartender in West Hollywood, California, while performing as a drummer in a band. From there, he held his first management position at a nightclub, eventually leaving to open his first bar in 1989. Over the next two decades, he rose to prominence in his industry as the President of the Nightclub and Bar Media Group and is recognized in the Nightclub Hall of Fame. In 2011, Jon’s hit reality TV show “Bar Rescue” premiered on Spike TV and is now in its seventh season. The show’s success led to the spinoff show “Marriage Rescue”, two bestselling books, a podcast called “No Excuses” and a new restaurant chain called “Taffers Tavern”. I’ve been meaning to get together with Jon for a while now and was especially interested in his business views during this pandemic. The 5 questions I ask in this episode: Jon, your industry has been greatly affected in this pandemic with many restaurants and bars that may never recover. You’ve said that the most important asset that people in any industry can build right now is trust and I agree. How can restaurant owners, or anyone else in business, build the trust that will put them in a better position in the aftermath of the pandemic? Even though you are a prominent figure in your industry, you started as a bartender in your youth, which is why I think you’re able to empathize with workers more than most. I also believe everyone should have a service job. I was a caterer for my temple! How did your first job as a bartender prepare you for your future in the industry? While your Bar Rescue and Marriage Rescue TV shows are different, both focus on relationships. Can you explain why most relationships fail and what all successful ones have in common? Over the course of your career, you’ve heard all kinds of excuses from people who are afraid to address their underlying issues. What is one excuse that you’ve made, how did you address it and what did you learn about yourself in the process? What is your best piece of career advice? Follow Steve’s journey: WebsitePodcastBooksTwitterInstagramFacebook

An interview with Steve Aoki how he monetized his passion, his reflections from being in isolation, how Avicii’s death impacted him, how he recovered from failure, and his best career advice. Welcome to the 83rd 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 DJ, record producer, and music executive, Steve Aoki. Born in Miami, Florida, Steve is the son of Rocky Aoki, the legendary owner of the Japanese restaurant chain Benihana. During college at the University of California, Santa Barbara, he produced do-it-yourself records and ran underground concerts and eventually launched his own record label called Dim Mak back in 1996. Steve’s label released music from a variety of electro house artists like Felix Cartal and Bloc Party while remixing songs from a variety of artists like Kanye West, Eminem, and Drake. He rose to international fame for his surfing stunts, cake throwing, champagne spraying, and riding rafts during his hundreds of performances each year. Steve’s first solo album, Wonderland, was nominated for a Grammy in 2013, which is the same year he was ranked in the top ten best DJ’s in America. Since then, he’s released four other hit albums, Neon Future I, II, III, and IV, launched his own comic book titled “Neon Future” and his memoir titled “Blue”. I first interviewed Steve eight years ago for a series I wrote for Forbes called “The World’s Greatest DJ’s” and out of everyone I interviewed, he was the most authentic and vulnerable. That’s why I was excited to catch up with him again for this podcast episode. The 5 questions I ask in this episode: Steve, we are constantly told to “follow our passion” and you’ve not only found your passion but turned it into a thriving career. What do you recommend to others who have either not found their passion or haven’t been able to monetize it? As someone who has toured the world many times over you’ve witnessed how your music has impacted different cultures. Now that you’re in isolation in your home, how have you reflected on your life journey and what will you do differently when your life gets back to normal? This month marks the two-year anniversary of Avicii’s death, one of the most celebrated DJ’s ever that I interviewed and you collaborated with. How did his passing affect you personally and made you think about the life you want to live and the legacy you want to leave behind? When you first started your label you were signing big acts, while simultaneously losing money. What steps did you take to become profitable again and how did this time in your career prepare you for the future? What is your best piece of career advice? Follow Steve’s journey: FoundationBookTwitterInstagramFacebookYouTube

An interview with Martin Dempsey about how to lead during a crisis, how conflicts in his career shaped his life perspectives, the common expectations that form relationships, the military figures that have influenced him, and his best career advice. Welcome to the 82nd 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 retired U.S. General and the 18th Chairman of the Joint Chiefs of Staff, Martin Dempsey. Born in Jersey City, New Jersey, Martin attended the U.S. Military Academy at West Point. After graduating he served as a company-grade officer, then went on to become an executive officer during Operation Desert Storm. He rose up the military ranks during the war in Iraq eventually becoming a General in 2008 and the Chairman of the Joint Chiefs of Staff under President Barack Obama in 2011. Four years later, Martin retired and was named to TIME Magazine’s 100 Most Influential People in the World. After over forty years of military service, he now teaches leadership and public policy as a Rubenstein Fellow at Duke University and serves as Chairman of USA Basketball. More recently, Martin authored the new book, “No Time For Spectators”, which is the basis for today’s podcast episode. The 5 questions I ask in this episode: Leaders in every institution are being tested right now with how they’re dealing with the Coronavirus pandemic. Based on your experience as a General in the U.S. army, what are your recommendations to leaders on how to manage this crisis or any crisis?As someone with over 40 years of military service, how have major conflicts impacted your leadership, perspectives on the world and how you live your life?In your book “No Time for Spectators” you examine the common expectations that forge the strongest relationships. What are the key mutual expectations that make any relationship successful?Over the course of my career, I’ve interviewed major military figures like Colin Powell and Stanley McChrystal. What military figures have influenced your leadership style and what did you learn from them?   What is your best piece of career advice? Follow Martin’s journey: WebsiteBookTwitterLinkedIn

An interview with Hilarie Burton about how she transitioned from Hollywood to a farm, how her life has changed, the most challenging skill she learned on the farm, the power of human connection, and her best career advice. Welcome to the 81st 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 One Tree Hill actress turned farmer and author, Hilarie Burton. Born in Sterling, Virginia, Hilarie was very active in high school as the captain of the cheerleading squad, the student council president, and homecoming queen. She started her career as a VJ on MTV’s Total Request Live then made an appearance on Dawson’s Creek before getting cast for her breakout role on One Tree Hill. Since then, she’s played lead roles in films such as Our Very Own, Solstice, and The List, and TV shows like Grey’s Anatomy, Forever and Lethal Weapon. More recently, Hilarie wrote her memoir “The Rural Diaries” and became a co-host, with her husband, of AMC’s “Friday Night In with The Morgans”. In this episode, Hilarie introduces us to her life on the farm and what she’s learned from her experience. The 5 questions I ask in this episode: How were you able to transition from being a bi-coastal Hollywood actress to raising a family on a farm and what were the hardest sacrifices you had to make?How have your views on life and work changed from the time you spent living in big cities to a small town? Reading your book reminded me of the reality show “The Simple Life” in that you’ve had to learn new skills to survive and thrive in your new environment like raising animals and running a candy store. What was the most challenging skill you had to learn and how did you learn it? While the coronavirus pandemic has resulted in isolation, job loss, and death, the silver lining is that many of us are getting closer even from a distance. What has this crisis, and your new life, taught you about the power of human connection?  What’s your best piece of career advice? Follow Hilarie’s journey: BookInstagramTwitter

An interview with Jim Kwik about how his childhood brain injury serves as his motivation, what his superpower and kryptonite are, what he’s learned from Will Smith, how to accelerate our learning, and his best career advice. Welcome to the 80th 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 CEO of Kwik Learning, Jim Kwik. Born in Westchester, New York, Jim suffered a brain injury when he was five, which hurt his brain performance and motivated him to study the power of the brain. He’s spent the past few decades training his brain for speed-reading and memory improvement. Jim has used his talents to coach clients including Google, Virgin, Nike, Harvard, and some of the most celebrated entertainers of our time like Will Smith and Hugh Jackman. He hosts the “Kwik Brain” podcast and his online training courses have impacted students in over 180 different countries. His advice and experiences have been captured in his new book “Limitless”, which teaches us how to learn so we can dramatically improve our performance. I first connected with Jim through Instagram, have since met him in person and I was excited to speak with him for this podcast episode. The 5 questions I ask in this episode: How did your childhood brain injury motivate you to master your own brain and then help others do the same? You and I both love superheroes and you talk a lot about superpowers when you communicate to audiences or through your content. What would you say your superpower is and what is your kryptonite? What’s fascinating about your life story is that you actually work with the actors behind the most beloved superheroes, helping them speed read their scripts so they can perform better. While it’s clear that you helped them become better actors, what did you learn from spending time with them that has furthered your education and brain performance? We both believe in lifelong learning. We aren’t students for 4-years, we are students for life. Can you tell me the most effective technique that can accelerate our learning so that we can become smarter as we age? What is your best piece of career advice? Follow Jim’s journey: WebsiteCompanyBookPodcastLinkedInFacebookYouTubeTwitterInstagram

An interview with Erika Nardini about being the CEO of Barstool Sports, how to stay relevant, handling pressure, her biggest challenges and best career advice. Welcome to the 79th 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 CEO of Barstool Sports, Erika Nardini. Born in New Hampshire, Erika studied sociology and philosophy at Colby College. While at first, she aspired to be a lawyer, she eventually decided to go into advertising and marketing. Early in her career, she was a Media Manager at Fidelity, where she learned first-hand the potential of the Internet for media purposes. Erika went on to hold executive positions at Arnold Worldwide, Modelina, Yahoo!, Demand Media and eventually became the Chief Marketing Officer at AOL. In 2016, she stepped into her role as the CEO of Barstool Sports, a satirical sports and lifestyle culture brand, which has grown to become the tenth largest distributed media company in America with 66 million unique visitors each month. Under Erika’s leadership, the company has grown from 15 to 201 employees, with revenues approaching $100 million and with a valuation of $450 million after an investment by Penn National Gaming this past January. As one of Fast Company’s Most Creative People, I was excited to speak to Erika about how she stays relevant, handles the rapid business growth and what it’s really like being a CEO. The 5 questions I ask in this episode: What does your daily schedule look like that enables you to manage a well-known brand like Barstool? I believe the biggest challenge for a company, product and human today is staying relevant in a world, industry, category and profession that’s constantly changing. How do you keep yourself and your company relevant?How have you been able to handle the pressure to exceed expectations with all of your stakeholders and continue to be a leader in the market?Can you talk about your biggest challenges and how you’ve navigated through them?What is your best piece of career advice? Follow Erika’s journey: CompanyTwitterLinkedInInstagram