David Kenny on Leading Through Uncertainty, Managing vs. Governance, and Why Curiosity Beats Expertise

Jim McCann on His First Flower Shop, 1-800-Flowers, and Firing Himself

Everything changes - except your brand and your story. Fifty years after buying his first flower shop, Jim McCann did something almost no founder does voluntarily: he fired himself. In this episode of Unbossing, hosts Rishad Tobaccowala and Drew Ianni talk with Jim McCann - founder and Executive Chairman of 1-800-Flowers - about what five decades of building, adapting, and letting go actually teach you. In 1986, Jim heard a radio ad for a struggling flower shop in Texas. He bought their telephone number, rebranded his company around it, and turned a 14-store flower shop chain into one of the most recognised brands in American retail. Since then, 1-800-Flowers has moved through six technology waves - from the 800 number to the internet to AI. But Jim’s lesson is clear: the real competitive advantage was never the technology. It was the relationship. He also opens up about stepping down as CEO and the advice that shaped his leadership philosophy: fire yourself from every function, so you can focus on the things only you can do. See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

David Kenny on Leading Through Uncertainty, Managing vs. Governance, and Why Curiosity Beats Expertise

What do you hold onto when almost everything is changing? David Kenny — co-founder of Digitas, former CEO of Nielsen, and one of the most sought-after board members in tech and media — has a simple answer: find your true north and don't deviate from it. In this episode of Unbossing, hosts Rishad Tobaccowala and Drew Ianni go deep with David on the leadership questions that are defining this moment: how to manage fear within teams, why AI makes curiosity more valuable than expertise, and the difference between managing and governance as a member of a board. He also makes a data-backed case for diversity as a winning business strategy — and shares what the 38 CEOs he's developed have taught him about resilience, failure, and what it actually takes to lead. See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

Jim Lesser on Craft, Taste and Going From Fun Uncle to the Responsible Parent

Jim Lesser started his career as a receptionist at a New York ad agency. His last role in that same industry was CEO of BBDO San Francisco — one of the few creative directors in advertising to ever make that leap. Now, as Chief Brand Officer at ServiceNow, he's doing something nobody expected: turning a B2B enterprise software company into a brand people actually know and feel something about. This week on Unbossing Jim Lesser talks with Rishad and Drew  about what he had to unlearn to go from receptionist to CCO, from CEO to CMO. Jim opens up about the unlearning that comes with every major career transition and how he went from the fun uncle to the responsible parent, from focusing on his team to focusing on every team. He makes the case that craft and taste is more important in the world of AI than ever before and that micro managing and attention to detail is a very different thing. See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

Tariq Hassan on Fear, Failure, and Brand Role in Culture

What if the fear of failure is the biggest thing standing between your team and greatness? Tariq Hassan — former CMO and Chief Customer Experience Officer of McDonald's and former CMO of Petco — has spent his career contemplating this question. In this episode of “Unbossing,” hosts Rishad Tobaccowala and Drew Ianni sit down with Tariq for a candid conversation about the leadership lessons hiding inside failure, the importance of psychological safety, and how the Grimace shake TikTok craze became a masterclass in knowing when to get out of the way of the consumer.  Tariq opens up about his late discovery of dyslexia — and how unlearning to hide it became one of his most powerful leadership tools. And he shares his framework for rooting out the "ghosts of culture past" that haunt organizations long after the people who created them are gone. Plus, hear Tariq’s career advice for everyone—no matter which career stage you’re at.   See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

Reed Hastings on Unlearning Leadership: From Netflix to the Mountain

Reed Hastings built Netflix from a DVD-by-mail startup into a global entertainment empire — and then did something most founders never do: he walked away. In this first episode of Unbossing, hosts Rishad Tobaccowala and Drew Ianni sit down with Reed for a candid conversation about the leadership principles he'd keep, the ones he'd rewrite, and what he's learned building something entirely new. Reed opens up about the famous Netflix Culture Memo — what it got right, what it got wrong, and why, if he could do it again, he'd lead with the heart. Now on the board of Anthropic and developing Powder Mountain into a private ski community in Utah, Reed reflects on the shift from the digital to the very physical — and what that's taught him about culture, community, and starting over. This is a conversation about unlearning the rules that made you successful, so you can build something even better.   See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.