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.