Unbossing
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Podcast Overview
<p>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.</p>
Language
🇺🇲
Publishing Since
2/2/2026
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Recent Episodes
June 23, 2026
Janet Foutty on Knowing When to Leave, Separating Who You Are From What You Do, and the Beginner's Mindset
<p>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.</p> <p>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.</p> <p>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.</p><p>See <a href="https://omnystudio.com/listener">omnystudio.com/listener</a> for privacy information.</p>
June 9, 2026
Sarah Personette on Leading with Balance, Reframing Imposter Syndrome, and Building Media's Future
<p>At seven years old, Sarah Personette told a stranger she wanted to be a CEO. She spent the next three decades making it happen.</p> <p>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.</p> <p>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."</p> <p>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.</p> <p>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.</p> <p>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.</p><p>See <a href="https://omnystudio.com/listener">omnystudio.com/listener</a> for privacy information.</p>
May 26, 2026
Jim McCann on His First Flower Shop, 1-800-Flowers, and Firing Himself
<p>Everything changes - except your brand and your story.</p> <p>Fifty years after buying his first flower shop, Jim McCann did something almost no founder does voluntarily: he fired himself.</p> <p>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.</p> <p>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.</p> <p>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.</p> <p>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.</p><p>See <a href="https://omnystudio.com/listener">omnystudio.com/listener</a> for privacy information.</p>
8 total episodes available
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Frequently asked questions
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- What is Unbossing?
<p>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.</p> - How often does this podcast release new episodes?
This podcast updates daily.
- Where can I listen to this podcast?
This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
Yes, this podcast regularly features guests.
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