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.
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Marian Goodell on Leading Burning Man and Why Collaboration and Consensus Are Not the Same Thing
In 1995, a project manager at a San Francisco software company drove twelve miles into a Nevada dry lakebed because a man in a bed sheet holding a plastic flamingo told her to. She never went back. That woman was Marian Goodell. Nearly thirty years later, she is the first and only CEO of Burning Man Project. In this episode of Unbossing, hosts Rishad Tobaccowala and Drew Ianni talk with Marian Goodell about what it means to lead an organization built on radical decentralization and no bosses — when you are, in fact, the boss. Marian arrived as a command-and-control project manager, learned to let it go, and built something genuinely collective. Then her co-founder passed away. Then the pandemic came. Then the rain nearly broke the event. Then the tickets stopped selling. Each challenge demanded something different — and each time, she had to decide whether to take the tiller herself or trust the community to sail the boat. Her lesson: collaborative decision-making and consensus are not the same thing. Knowing the difference might be the most important skill in leadership today.
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21 Jul 2026
Ann Mukherjee on Crashing the Super Bowl, Embracing Your Weaknesses, and Why the CEO of Today Has to Be All Learning
When Ann Mukherjee joined Doritos in 2006, the brand was in freefall. It had gotten so bad that Frito-Lay's own truck drivers refused to stock it. She turned it around by crashing the Super Bowl with a $5 million budget—against Anheuser-Busch's $100 million—by handing the ads to consumers and trusting them to do it better.
In this episode of Unbossing, hosts Rishad Tobaccowala and Drew Ianni talk with Ann Mukherjee—former Chairman and CEO of Pernod Ricard North America—about thirty years of walking away from what she'd just mastered to learn something entirely new. From Kraft to Frito-Lay to SC Johnson to Pernod Ricard, Ann's rule was simple: when you stop learning, you're done. Each move meant unlearning the previous company's system before her old instincts could become the wrong answer in a new place. She also challenges the conventional wisdom on weakness. Don't try to fix them. Understand them, compensate for them, and use them to find what you're actually built for. Perfection, she says, is a sickness. Her last lesson: the CEO of the past was expected to be all-knowing. The CEO of today has to be all learning.
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23 Jun 2026
Janet Foutty on Knowing When to Leave, Separating Who You Are From What You Do, and the Beginner's Mindset
For 33 years, Janet Foutty helped the world's largest companies reinvent themselves. Then she had to do it herself. When she stepped down as Executive Chair of Deloitte US, she didn't walk into a plan. She walked into a blank page she didn't know how to fill.
In this episode of Unbossing, hosts Rishad Tobaccowala and Drew Ianni talk with Janet Foutty, former CEO of Deloitte Consulting and former Chair of Deloitte US, about what it means to unlearn the thing you were best at.
Janet spent three decades at one firm. She knew every hallway, every decision, every person to call. Then she left and quickly discovered that map didn't work anywhere else. Her lesson: the beginner's mindset doesn't kick in until you no longer have an organization to cover for you. We're all leaders in training, including the ones who've already led everything.
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9 Jun 2026
Sarah Personette on Leading with Balance, Reframing Imposter Syndrome, and Building Media's Future
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.
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26 May 2026
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.
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12 May 2026
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.
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28 Apr 2026
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.
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14 Apr 2026
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.
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1 Apr 2026
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.
2 Feb 2026
Unbossing ... Coming Soon!
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.
See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
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