Wisdom From The Top with Guy Raz

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.

Margaret Heffernan, an entrepreneur, CEO, executive leadership coach, and author of six books, delves into her often counter-intuitive insights on consensus-building, and decision-making. She and Guy discuss her book, Uncharted: How to Map the Future, where she explains why attempts to predict the future, even with today's AI and Big Data technologies, are often doomed to fail. Instead, Margaret offers alternative strategies for organizations facing an uncertain future—strategies rooted in human creativity and resilience. Plus, the importance of recognizing your inner super chicken. Known for challenging conventional business wisdom, Margaret’s perspective is a refreshing take on how to navigate the complexities of the modern world.

The former CEO of KFC and Popeye's doesn't love talking about success, of which she's had plenty. No, in fact she's more interested in life's stumbles, in the complexity of failures, and what they have to teach her and her team. Her leadership style is highly relational ("I must know you to grow you," she says). Bachelder became President of KFC years later, but a job that started as a major opportunity wound up being a massive failure. In this conversation with Guy Raz from 2020: How Bachelder learned from her failures and went on to turn Popeyes into one of the biggest success stories of the past decade.

The legendary CEOs of the 1990s included Jack Welch of GE and John Chambers of Cisco, who was on our show last season. Another dominant figure was Lou Gerstner of IBM, the first IBM CEO recruited from outside the company. When he became CEO in 1993, IBM was struggling against competitors like Microsoft, Dell, and Compaq. Gerstner famously declared, "The last thing IBM needs right now is a vision," and instead focused on breaking through internal bureaucracy and making tough decisions. His approach transformed IBM, boosting its market cap from 29 billion to 168 billion over nine years. In this 2020 conversation, Lou shares his journey to the CEO role and the principles behind IBM's turnaround.

Brad Smith, the former CEO and now Chairman of the Board at Intuit, knows first hand why vulnerability and failure are intrinsic to good leadership. At one point in his career he lost $40 million for a company and then...got promoted. Smith, heavily influenced by his father's wisdom (i.e. "put a chink in your own armor") leaned into the power of authenticity, humility, and vulnerability to inspire others. At Intuit, Smith led the company through one of its most significant transformations, reinventing it into a high-powered cloud-based platform and reigniting a startup culture within a decades-old software firm. In this 2019 conversation, leadership principles meet real-world application. The watchwords? Authenticity and vision.