Wisdom From The Top with Guy Raz

Note: This is the first in a series of episodes of The Way Up, a new video series from Square highlighting the real stories of grit, vision, growth, and heart behind some of America’s most innovative local businesses.

What happens when you can’t find a place to watch women’s sports? You build one. Jenny Nguyen is the founder of The Sports Bra, a first-of-its-kind sports bar in Portland, Oregon, that only plays women’s sport...

Ken Coleman, known as “America’s Career Coach,” shares his wisdom on finding meaningful work and building connections to achieve your career goals. Drawing from his own journey—spanning a decade of diverse jobs before discovering his true passion in broadcasting—Ken offers practical advice from his books, The Proximity Principle and One Question. In this encore episode, he challenges listeners with one thought-provoking qu...

As a child growing up in Ibadan, Nigeria, Dara Treseder was often reminded to keep her feet on the ground. But her mother urged her to dream big and pursue her ambitions—especially if they brought her fulfillment. That encouragement propelled Dara across the world, where she attended both Harvard and Stanford, charting a path defined by her desire to make a positive impact.

Dara’s journey into marketing began after what she...

ENCORE EPISODE. Joe Keohane, a seasoned journalist and editor, believes that conversations with strangers can boost happiness, empathy, and even improve the world around us. In his book The Power of Strangers: The Benefits of Connecting in a Suspicious World, Joe dives into research with psychologists, anthropologists, and real-life encounters to uncover the profound impact of these connections. In this encore episode, Guy...

What drives lasting personal change? BJ Fogg, founder of Stanford’s Behavior Design Lab, challenges conventional wisdom with insights from his groundbreaking book Tiny Habits: The Small Changes That Change Everything. Drawing from real-life experiments and research, Fogg reveals a practical system for building positive habits and breaking free from negative ones. In this episode, first aired in 2021, discover transformativ...

When Ken Hicks took the helm as CEO of Foot Locker in 2009, the company was on the brink: the economy was in shambles, sales had cratered by nearly a billion dollars, and the decline of indoor malls spelled further doom. But within three years, Hicks led Foot Locker to a stunning $2 billion rebound. His strategy? A renewed focus on storytelling—connecting the brand to customers in a way that transcended price tags and prod...

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...

"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 di...

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 e...

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 leader...

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 stepp...

"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 explor...

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 ...

[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...

[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 ...

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 groundbre...

[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 g...

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 w...

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 ...