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.

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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.

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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.

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