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.

What do you hold onto when almost everything is changing? David Kenny &mdash; co-founder of Digitas, former CEO of Nielsen, and one of the most sought-after board members in tech and media &mdash; 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 &mdash; and shares what the 38 CEOs he's developed have taught him about resilience, failure, and what it actually takes to lead.

Hosts Rishad Tobaccowala and Drew Ianni are Reinventing Leadership in Chaotic Times and will feature conversations with the most fearless leaders in business and tech about what they’ve had to unlearn to succeed again in a world where the future no longer fits old rules.

Hosts Rishad Tobaccowala and Drew Ianni are Reinventing Leadership in Chaotic Times and will feature conversations with the most fearless leaders in business and tech about what they&rsquo;ve had to unlearn to succeed again in a world where the future no longer fits old rules.

Unbossing

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

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/00c7a33a-09eb-42ab-9898-b448001f6bee/transcript

At seven years old, Sarah Personette told a stranger she wanted to be a CEO. She spent the next three decades making it happen.

Days after Elon Musk closed his $44 billion acquisition of Twitter, she resigned — walking away from a role she'd spent four years building, and stock she hadn't fully vested, to protect what she stood for.

In this episode of Unbossing, hosts Rishad Tobaccowala and Drew Ianni talk with Sarah Personette — CEO of Puck, the media startup the New York Times called "Vanity Fair for the Substack era."

Sarah's career ran through advertising agencies, Facebook, and Twitter. She took a demotion to join a startup called Facebook because she could see where the industry was heading. At 26, she managed a 90-person team through the 2008 financial crisis. At 33, she was U.S. President of Universal McCann.

The lesson she carries through all of it: the leaders who survive disruption aren't the ones who avoid fear. They're the ones who name it, move through it, and bring their teams with them.

She also makes the case that kindness isn't a soft idea, it's the thing that makes organizations actually perform when it matters most.

At seven years old, Sarah Personette told a stranger she wanted to be a CEO. She spent the next three decades making it happen.
Days after Elon Musk closed his $44 billion acquisition of Twitter, she resigned &mdash; walking away from a role she'd spent four years building, and stock she hadn't fully vested, to protect what she stood for.
In this episode of Unbossing, hosts Rishad Tobaccowala and Drew Ianni talk with Sarah Personette &mdash; CEO of Puck, the media startup the New York Times called "Vanity Fair for the Substack era."
Sarah's career ran through advertising agencies, Facebook, and Twitter. She took a demotion to join a startup called Facebook because she could see where the industry was heading. At 26, she managed a 90-person team through the 2008 financial crisis. At 33, she was U.S. President of Universal McCann.
The lesson she carries through all of it: the leaders who survive disruption aren't the ones who avoid fear. They're the ones who name it, move through it, and bring their teams with them.
She also makes the case that kindness isn't a soft idea, it's the thing that makes organizations actually perform when it matters most.

Sarah Personette on Leading with Balance, Reframing Imposter Syndrome, and Building Media's Future

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/531a9def-99da-42dc-bd49-b463013f5563/transcript

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.

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&rsquo;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.

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

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/3c9b304f-d917-4c69-b910-b455001955ac/transcript

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.

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 &mdash; 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&nbsp; 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.

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

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/43bedaa7-bf46-46b9-bb4b-b43900d311a6/transcript

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

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