Wisdom From The Top with Guy Raz

[A 'BEST OF' EPISODE] Combining business with social justice isn’t a path most companies choose, which is why Dan Schulman’s leadership as PayPal’s CEO captured so much attention. In 2016, he halted plans for an operations center in North Carolina in response to the state’s controversial “bathroom bill.” Schulman prioritizes an “employee-first” strategy, enhancing wages and benefits for PayPal employees. His leadership has demonstrated that activism doesn't takes anything away from the bottom line. In this 2020 conversation, Schulman reflects on the childhood that shaped his current values, and his journey from AT&T, Priceline, and eventually to CEO (now President) of PayPal.

[Encore release] General Stanley McChrystal was born into a military family: three generations of men in his family were officers in the armed forces. He followed the family tradition and eventually rose up the ranks to become a General in the Army. While serving as the commander of Allied Forces in Afghanistan in 2010, he was forced to resign after he was quoted making disparaging remarks about President Obama. It was in the wake of this moment that General McChrystal learned the full value of leadership. In this conversation from 2020, the General reflects on the very specific lessons of leadership he learned, and evolved, throughout his time of military service.

An encore episode, exploring the unconventional leadership journey of Carl Bass, a self-described renegade and reluctant executive who took the reins at Autodesk during turbulent times. Facing the global economic crisis of 2008, Bass led with conviction, balancing bold decision-making with the uncertainty of an evolving market. At one point, convinced the company might fail, he risked his own money to introduce a groundbreaking new business model. How Bass's steady hand and innovative thinking not only helped Autodesk survive but transformed it into a 21st-century success story. This conversation took place in 2019.

[Encore episode] In the 1980s, Stephen R. Covey revolutionized leadership thinking with The 7 Habits of Highly Effective People, introducing a leadership style centered on empathy, listening, and collaboration—far from the traditional table-pounding, charismatic approach. In this episode, Guy sits down with Stephen M.R. Covey, Covey’s son, who has not only been instrumental in spreading his father’s influential teachings globally but has also become a respected leadership expert in his own right. Stephen shares insights from his own bestselling leadership books and reflects on the lasting impact of his father’s groundbreaking work.

Author, and business executive Beth Comstock says to Guy Raz in this classic 2021 interview "I'm about change." In college, she wanted to be a doctor, but organic chemistry wasn’t her strong suit, so she shifted to journalism. When journalism didn’t work out, she started working in publicity. So, when GE bought NBC in 1986 right as Beth was starting her career in advertising, she was ready to adapt again. She worked her way to becoming CMO of GE, helping grow revenue, devise a successful green energy program, and more. Then, when NBC began to explore their approach to digital media, Beth couldn't resist returning to the storied network, where a new frontier in media was opening up (for reference: this was around the time Google bought YouTube). While there she helped seed what would become Hulu. Around the time of the 2008 financial crisis, Beth returned to GE as the company's first female Vice Chair of Business Innovations, which was also around the time she penned the inspiring and candid book Imagine it Forward: Courage, Creative, and the Power of Change .

General David Petraeus is one of those leaders who rose through the ranks to become one of the most well-known military figures of our time. Growing up in the shadow of West Point, General Petraeus defied the odds in a career where becoming a four-star general is nearly as unlikely as being struck by lightning.Petraeus’s rise to prominence began in 2003, but it was in 2007, as the commander of Multi-National Forces in Iraq, where he made his mark by leading the controversial but pivotal “surge.” He later commanded coalition forces in Afghanistan during one of the deadliest periods for U.S. troops, before transitioning to a new chapter as the Director of the CIA under President Obama.In this encore episode, General Petraeus shares his insights on leadership, revealing that the key to success lies in “getting the big ideas right,” refining them, and ensuring they’re communicated effectively across an entire organization.

Terry Lundgren, former CEO of Neiman Marcus and Macy’s, has been instrumental in shaping the American retail landscape. His believes leadership lies dormant in many until an event challenges you to grow. He also believes playing it safe is the biggest risk of all. Despite an entire career in retail, including taking on the role of president of a local department store when he was 35--succeeding a 67-year-old, the road he took to bringing two notoriously competitive retail giants together wasn’t easy. How he merged famous department rivals, double-downed on retail, and turned Macy’s into the first nationwide department store in the United States.

Jim Collins is one of the most influential business thinkers and writers of our time. Yet, Collins considers himself more of a researcher than an author.He has made a career of extracting the data embedded in the narrative arcs of companies and drawing lessons from them. With bestsellers like Good to Great, Built to Last, and BE 2.0, each of his books represents years of meticulous analysis, all before he even begins to write. What sets Collins apart aren't just his groundbreaking ideas but the unconventional choices that shaped his career. In this interview from 2021, Collins unpacks insights from his research, among them: the fact that ideas don't matter as much as people think they do. In fact, he found a negative correlation between starting a business with a great idea and creating a successful and enduring company. The key lies in "clock building" rather than "time telling," that is—creating a system and structure that transcend any one innovation or product. (He uses examples like Sony, which began with a failed rice cooker). Another side to this concept can be summed up with "preserve the core, stimulate progress." When leaders maintain what is core to the company, they can continually evolve their strategies and other aspects and build companies that last.

Can ancient philosophy be the key to modern success? Ryan Holiday, a leading thinker of his generation, believes so. From NFL quarterbacks to corporate CEOs, many credit Holiday's work with introducing them to the transformative power of Stoic philosophy. In this episode, Ryan talks to Guy about the teachings of the Stoics through the lens of Holiday's influential books, including The Obstacle Is The Way, Ego Is The Enemy, Stillness Is The Key, and, most recently Right Thing, Right Now. These aren't just bestsellers—they're respected works that have left a lasting impact on leaders and entrepreneurs around the world. But Ryan Holiday's journey wasn't always about philosophy. Before becoming a celebrated author and podcaster (The Daily Stoic) he started his career in marketing, a field that would shape his first book and inform parts of many others. This conversation was recorded in 2021.