My guest today is the host and author of How I Built This, Guy Raz. He started his career as an intern at NPR’s “All Things Considered”, then became a foreign correspondent before taking a two-year stint at CNN. Guy then returned to NPR, starting hit shows like the TED Radio Hour and the How I Built This podcast, where he interviews famous entrepreneurs from companies like Allbirds, Yelp, and Airbnb. Now Guy has turned his podcast into a book by the same name, which we discuss in this podcast episode. The 5 questions I ask in this episode: What lessons did you learn early on in your career when you were with NPR and CNN that helped you become an effective interviewer and storyteller today? I’ve interviewed about 2,300 people in my career and you’re at over 6,000. Which guest was most surprising to you and what was the most inspirational moment that had a lasting effect on you? It seems like so many entrepreneurs have a safety net, in the form of family money or a full-time job, that enables them to execute on a big idea. Do you believe there is such a thing as “rags to riches” and “self-made” or do all entrepreneurs have a financial advantage when they start? In two previous episodes I asked billionaire venture capitalists Ben Horowitz and Chamath Palihapitiya about the qualities all successful entrepreneurs have in common and they said they are original thinkers, have leadership skills, a learning mindset, and deep-seated insecurity. Do you agree with this list and would you add anything to it?What’s your best piece of career advice? Follow Guy’s journey: Website BookTwitterFacebookInstagramLinkedIn

My guest today is fashion designer, Betsey Johnson. Betsey has been rocking the fashion industry with her unique designs since the 1960s. She became known for her over-the-top fashion and doing cartwheels ending in a split at the end of fashion shows. Her journey from dancing in her childhood to filing for bankruptcy is captured in her new memoir titled “Betsey”, which we discuss in this podcast episode. The 5 questions I ask in this episode: In your book, you talk about fearing death as a child. How does your fear of death impact your decision making throughout your life? You admit that you inherited your father’s work ethic and your mom’s energy. How did both of these qualities help you as you build your career and brand? You’ve encountered many hardships in your life like cancer, divorce, and bankruptcy. How were you able to overcome these challenges and what life and business changes did you have to make? In a previous episode of this podcast, I spoke to Stuart Weitzman about how he’s kept his brand fresh and relevant for so long. How have you been able to sustain your brand and diverse customer base for multiple decades? What is your best piece of career advice? Follow Matthew’s journey: Book

My guest today is Academy Award–winning actor, Matthew McConaughey. You might know Matthew as the A-list actor that has appeared in over 40 feature films that have grossed over $1 billion like “Dazed and Confused” and Dallas Buyers Club”, but he’s also a deeper thinker, family man, and professor. After decades of keeping a journal, he captured much of his life experiences, quotes, and stories in his new book “Greenlights”, which we discuss in this podcast episode. The 5 questions I ask in this episode: How did journaling for 35 years help you better understand your life and career through both your hardships and successes? In your memoir, you use the analogy that on the highway of life we have red, yellow, and green lights. How did your father’s death eventually become a blessing for you, turning a red to a green light? I completely agree with you that the first step to knowing who you are is knowing who you aren’t. How did you use the process of elimination to discover yourself and choose the right career path? People around the world are suffering from stress, anxiety, and depression. What prescribes do you have to help others manage difficult situations and improve their mental health? I know you don’t consider yourself a preacher and this isn’t an advice book, but I ask every guest this one last question. What is your best piece of career advice? Follow Matthew’s journey: BookInstagramFacebookTwitter

My guest today is fashion designer and entrepreneur, Steve Madden. Steve started his first company back in 1990 with a mere $1,100 selling shoes out of the trunk of his car and today his company is worth over $3 billion. Along the way, he struggled with alcohol addiction and went to jail for over two years for stock fraud. Steve’s story of both failure and success is captured in his new book, “The Cobbler”, which we discuss in this podcast episode. The 5 questions I ask in this episode: After you dropped out of college you got a job as a traveling salesman for a shoe company but didn’t have a driver’s license because you had so many DUIs. This didn’t stop you from being successful at your job though. How did this early experience shape you as a business person and become the foundation for your future company? What motivated you when you were building your company from scratch and how were you able to grow the brand while simultaneously battling your alcohol and drug addiction? In your memoir, you talk openly about the high and low points in your life. One of your lowest points was when the FBI arrested you for participating in a “pump and dump” scheme that was orchestrated by Jordan Belfort and illustrated in The Wolf of Wall Street movie. What led you down that path and what lessons did you learn during your 2.5-year prison term that can be applied to business and life? You credit your team for many of your company’s achievements and I find in business that hiring is stressful and time-intensive. What are some of the unconventional hiring strategies that have allowed you to build a team that led to your success? What is your best piece of career advice? Follow Steve’s journey: BrandBook

My guest today is singer and former Fifth Harmony member, Ally Brooke. Ally rose to fame as part of the multiplatinum music group Fifth Harmony before launching her solo career last year. She competed in ABC’s Dancing With The Stars then embarked on her Time To Shine Tour at the start of this year. After receiving billions of streams for her music through the course of her career, she wrote her memoir “Finding Your Harmony”. I spoke to Ally about her early struggles and insecurities, music influences, and her uplifting advice, which is especially important in these turbulent times, for this podcast episode. The 5 questions I ask in this episode: Even though you are of Mexican-American descent, you didn’t know Spanish as a child because your parents wanted to protect you from discrimination at school. How do you think their decision impacted your childhood and how have you embraced your heritage ever since?Since you’re the only entertainer in your family, who did you look up to how they did they influence you as an artist and your career choices? You said that you struggled with self-confidence growing up and that insecurity was heightened while you were part of Fifth Harmony, where you were compared to the other members and bullied. How has your experience with Dancing with the Stars and breaking out as a solo artist helped you gain self-confidence, feel empowered, and be fulfilled? I believe the hardest moments in our lives shape who we become. What was your greatest challenge, how did you overcome it and what did you learn about yourself in the process? What is your best piece of career advice? Follow Arthur’s journey: WebsiteBookInstagramFacebookTwitterYouTube

My guest today is the co-founder of The Home Depot, and owner of The Atlanta Falcons, Arthur Blank. Arthur built The Home Depot from an idea back in 1987 to a $50 billion-dollar company with 2,285 locations and is the leading home improvement retailer in the world. In this episode, we delve into what makes a “Good Company”, based on his new book, and discuss the importance of both building, and working for, a values-based organization that supports society, while making a profit. The 5 questions I ask in this episode: Many prominent leaders I’ve spoken to during this pandemic, like Reed Hastings, John Mackey, Jon Taffer, and Former General Martin Dempsey, have said that trust is the most important asset leaders can build right now. How were you able to create a culture of trust at Home Depot that led to both a positive work environment and higher financial returns? I’ve always believed that values give us a framework that guides our decision-making process. How did you decide on Home Depot’s values of giving back, building strong relationships, and doing the right thing and how do these values reflect your own? 3) Last year the Business Roundtable defined the purpose of a corporation to focus on all stakeholders instead of just making a profit, even though we are in a capitalistic society. In what ways can companies support society, while also turning a profit? One of the trends I’ve been studying over the past year is stakeholder activism. Today’s employees and consumers expect companies to take a stance on social and political issues, but it can be very tricky to do so. What do you recommend to leaders on how to manage stakeholder activism? What is your best piece of career advice? Follow Arthur’s journey: CompanyBookInstagramFacebookTwitterLinkedIn

My guest today is the chef and founder of Momofuku and the star of Netflix’s Ugly Delicious, David Chang. Since opening Momofuku Noodle Bar in New York City back in 2004, he’s been honored with six James Beard Awards and has been recognized as a TIME 100 honoree. In this episode, David opens up about his many life struggles as he illustrates in his new memoir, “Eat a Peach”. The 5 questions I ask in this episode: You had a lot of insecurities in your childhood, such as not being a great chef and feeling like an outsider as a Korean when most chefs were white. How were you able to cope during that dark period in your life and what did you learn about yourself in the process? You are extremely self-aware through the pages of this book. You said that “working so hard was a side effect of depression” and I felt like that during my 20s working over 100 hours a week. The work was my outlet. How did your mental health issues motivate you to become a successful chef? In the book, you explain that despite your success you feel like you’ve created your own prison because you’re a workaholic with numerous responsibilities between the book, your show, restaurants, and your kid. Plus, you’ve had to close restaurants due to the pandemic. Now that you’ve reached the top of your profession, what are some ways you can escape the prison you created for yourself? Your father was a pivotal player in helping you break into the restaurant industry by getting you a $100,000 loan. Can you describe the complicated relationship you had with your dad, what you learned from him, and his impact on your life? What is your best piece of career advice? Follow David’s journey: BookPodcastInstagramFacebookTwitter

My guest today is the co-founder and CEO of Whole Foods, John Mackey. John grew Whole Foods from founding it in 1980 to becoming a $13 billion Fortune 500 company, with over 80,000 employees, which he eventually sold to Amazon in 2017. I first interviewed him back in 2013 when he was starting to evangelize the conscious capitalism movement, then caught up with him in 2017 when he released his first cookbook. That’s why I was overjoyed that I got to catch up with him again to talk about his new book “Conscious Leadership” for this podcast episode. The 5 questions I ask in this episode: Your father was a role model for you in your childhood and even an investor in your company. What life lessons did you learn from him that has helped you become the leader you are today? Business values are at the core of Conscious Capitalism and Leadership. How did you originally identify your personal values and then embody them through your company for so many years? In today’s society, people work for and buy from companies that have a clear purpose not just make a profit. Employee and consumer activism have been heightened by recent political and social events like the killing of George Floyd. How can leaders focus on operating their businesses while also being sensitive to the global issue’s stakeholders care about? I’ve spoken to a lot of business leaders about what it takes to lead during a crisis such as the pandemic we’re living through right now and they say that trust is critical to sustainability. How have you been able to build trust with your workforce during this time? What is your best piece of career advice? Follow Reed’s journey: BookNon-profitLinkedIn

My guest today is the Co-Founder, Co-CEO, and Chairman of Netflix, Reed Hastings. After speaking to the other Netflix Co-Founder, Marc Randolph, for episode 53, I was delighted at the opportunity to speak with Reed to get the other side of the Netflix story, as well as learn from his experiences building the company and their workplace culture. Since Co-Founding Netflix back in 1997, Reed has revolutionized the entertainment industry, growing the company to over 183 million subscribers in 190 countries. He captures his journey, and lessons learned in his new book “No Rules Rules”, which we discuss in this episode. The 5 questions I ask in this episode: When you were the CEO of Pure Software you learned that tightly controlled management policies stifle creativity, which is why at Netflix you created a flexible work culture. Today’s professionals desire flexibility and that’s been made even more clear during this pandemic, where remote work has been normalized. How does a flexible work culture enable companies to adapt to changes and innovate faster? By promoting employee freedom, and eliminating rigid policies, you built organizational trust. How does giving employees the freedom to build the trust that leads to a healthier and more productive workforce? In the book, you said that hiring talented, creative, and diverse people was the “most critical dot for the foundation of the whole Netflix story”. What’s your approach to competing for and retaining the best talent, while promoting diversity and inclusion? In your childhood, you concealed your emotions from your family, which eventually became an issue for you as a leader and husband. What did your marriage counselor teach you about sharing your feelings, being honest, and giving transparent feedback and how did you apply that advice to your work relationships? What is your best piece of career advice? Follow Reed’s journey: BookTwitterLinkedIn

My guest today is a former monk turned social media phenomenon and author of Think Like a Monk, Jay Shetty. I first met Jay several years ago in New York City and right away, I knew he was someone very special with a bright future. In one of our early conversations, he mentioned his interest in writing a book called “Think Like a Monk” and that book was just published today! This is our fourth interview and he’s my only return guest! I caught up with Jay to dive deep into the major themes and ideas in the book for this podcast episode. The 5 questions I ask in this episode: You start your book talking about values. How do you figure out what your values are and then start to notice them in other people? So many things are competing for our time now, especially with social media, the fear of missing out, and we are bombarded with news, even fake news. How do we what to listen to and get into a headspace so that we can do what we’re meant to do and not what others expect of us? Values follow intentions. Can you talk about setting those intentions and then following through on them? You talk about getting to the root of the problem and the importance of asking why. How did you do this in your own life? What’s your best piece of career advice? Video interview from New York City: Follow Jay’s journey: WebsiteBookTwitterLinkedInFacebookInstagram