Wisdom From The Top with Guy Raz

Etsy was on the brink of collapse in 2017—its stock plummeting, cash reserves dwindling, and analysts predicting its demise. Enter Josh Silverman, a turnaround expert with a track record from Evite, eBay, and Skype. As Etsy’s CEO, Josh focused the team on one key metric, sparking a stunning recovery. How did he transform a failing creative marketplace into a thriving powerhouse? In this conversation from 2020, Guy and Josh dive into the success factors of the Etsy turnaround, as well as the key moments in Josh's leadership journey.

"How do you build a team, inspire individuals to pursue their dreams, and scale that impact beyond just one group?" Kim Scott has wrestline with, and answering that question for the majority of her career. After navigating roles from a diamond business in Moscow to Silicon Valley startups and then leadership at Google, she developed 'radical candor'—a transformative management philosophy that balances personal care with direct challenge. In this episode, we revisit a conversation originally recorded in 2021, where Kim shares insights from her groundbreaking book Radical Candor. She explores the importance of honesty, humanity, and fostering healthier power dynamics in the workplace. Whether you're a manager, a CEO, or simply someone passionate about leadership, Kim’s wisdom is as relevant today as ever.

What makes someone excel—whether in sports, science, or life? David Epstein, author of The Sports Gene and Range: Why Generalists Triumph in a Specialized World, makes a compelling case for the power of breadth over early specialization. From his time as a walk-on track athlete at Columbia University to his time as a science writer and investigative reporter (at Sports Illustrated and ProPublica, among others), David has explored the hidden patterns that lead to success. In this encore episode, recorded in 2021, Guy asks David about his journey from geology student and star athlete to bestselling author. Why a diverse set of skills and experiences often leads to better outcomes, and why embracing range could be the key to your next breakthrough.

What does it take to rebuild a company from the brink of failure? In this conversation from 2020, Guy sits down with Peter Cuneo, the former CEO who famously guided Marvel Entertainment out of bankruptcy and onto a path that ultimately led to its $4.5 billion acquisition by Disney. They explore the career trajectory that got him, as he puts it “offically addicted to turn around challenges." And unpack some of the 32 leadership principles he has developed over the years. How Cuneo’s turnaround philosophy, born from his experiences in the Navy and Vietnam, helped him identify Marvel’s untapped potential, shift its focus toward intellectual property, and pave the way for its cinematic universe.

In 2012, Best Buy was in deep trouble—a crisis so severe that Forbes declared, “Why Best Buy is Going Out of Business.” By March, the company reported a staggering $1.7 billion loss, and by April, its CEO had stepped down amid scandal. Enter Hubert Joly, a leader whose career had shaped him into essentially an elite relief pitcher of the business world. Armed with calm focus and a knack for navigating adversity, Joly stepped up to the plate just as the future of big-box retail hung in the balance. In this classic 2019 episode, discover how Joly took the helm at Best Buy during one of the most tumultuous moments in its history.

"You can't analyze your way into something new," says today's guest. Over the course of a career spanning four decades, Roger Martin has been a management consultant, an influential business strategy thinker and author, as well as the Dean of the Rotman School of Management at University of Toronto. He advises CEOs of global companies such as Ford, Proctor & Gamble, and Lego. He is well known for developing and exploring the concept of "integrative thinking" in management problem solving and for troubling conventional management wisdom as he does in his book, A New Way to Think: Your Guide to Superior Management Effectiveness. In this episode, recorded in 2021, Martin challenges the relentless drive for efficiency and advocates for a re-think in approach.

When Arnold Donald took the helm at the Carnival Corporation, a public relations crisis of multiple layers threatened its future. Donald prioritized building a diverse and dynamic leadership team, appointing new heads for seven of the company's nine cruise lines, including more women and minorities. in this 2019 conversation, Donald shares his philosophy that "diversity of thinking is a business imperative and a powerful advantage," explaining how fresh perspectives lead to innovative ideas and drive growth. How his strategies helped him rebuild Carnival into one of the industry’s most valuable brands.

[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.

In a world where scale is, for many, their north star, Graeter's Ice Cream stands out by doing things the old-fashioned way. Richard Graeter, the fourth-generation leader of this iconic family business, talks to Guy about the century-old process that makes their ice cream so special—and why they refuse to give it up. Unlike the huge companies that share their Cincinnati roots (i.e. Kroger and Proctor & Gamble), Graeter’s has chosen to stay small, valuing quality and sustainability over rapid expansion. In this conversation from 2020, Richard shares his journey from aspiring veterinarian to helming a company that prioritizes legacy and craftsmanship, strength and sustainability. Sometimes less really is more.

What does it take to create a winning culture in the workplace? For Ajay Banga, who transformed Mastercard, success is built on more than intelligence and emotional awareness. For him, it's the "Decency Quotient" that is an essential factor in fostering an environment where people feel supported, respected, and empowered to succeed. And, as he tells Guy in this 2019 conversation, it's not only about being kind. How Ajay Banga ran one of the worlds largest companies with an unusual leadership philosophy. And how he turned Mastercard from a credit card company into a company that's known for technology and innovation and data and analytics and A.I. 

In today's fast-paced corporate world, the pressure to specialize is immense. But what if focusing on one expertise isn't the key to success? Cliff Hudson, author of Master of None, challenges this very notion, arguing that versatility, not specialization, is the real path to leadership. Hudson's own life story is a testament to this belief. Growing up amidst the instability caused by his father's failed roofing business, Cliff was determined to find a secure career. He began his professional journey as a lawyer, but by 1995, he had risen to become the CEO of Sonic Drive-In, one of America's most iconic fast-food chains. In this conversation that took place between Guy and Cliff in 2020: How a young lawyer transitioned from the courtroom to the boardroom, redefining what it means to be a leader in today's world. Learn what embracing a broader skill set can lead to.

For George Scangos, the art of decisive leadership is part of his biology, you could say. Scangos is a former lab researcher who rose to the top of the biotech world. Transitioning from a biology researcher at Yale to a pharmaceutical executive, his journey is a testament to the power of interpersonal skills and strategic thinking. As the CEO of Biogen, he transformed the company's performance, leading it to become one of the top performers in the S&P 500 within his first year. In this 2019 conversation, Scangos unveils his approach to tough decision-making and the culture-shaping strategies that drive success. Chief among those strategies: creating space for people to feel comfortable to fail.