Rephonic
Artwork for Unbossing
Artificial Intelligence
Servicenow
1-800-Flowers
Fear
Failure
Branding
Leadership
Netflix
Brand
Data
Culture
Advertising
Nielsen
Diversity and Inclusion
Digital Media
Teaching and Mentoring

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.

PublishesTwice monthlyEpisodes7Founded4 months ago
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BusinessMarketingSociety & CulturePersonal Journals

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Artwork for Unbossing

Latest Episodes

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 ... more

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 ... more

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 ... more

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 Servi... more

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Recent Guests

Sarah Personette
CEO of Puck
Puck
Episode: Sarah Personette on Leading with Balance, Reframing Imposter Syndrome, and Building Media's Future
Jim McCann
Founder and current chairman of 1-800-Flowers
1-800-Flowers
Episode: Jim McCann on His First Flower Shop, 1-800-Flowers, and Firing Himself
David Kenny
Executive with a track record across Bain, Digitas, Weather/IBM, Nielsen
Nielsen; Teach for America; Best Buy (board)
Episode: David Kenny on Leading Through Uncertainty, Managing vs. Governance, and Why Curiosity Beats Expertise
Jim Lesser
Chief Brand Officer, ServiceNow
ServiceNow
Episode: Jim Lesser on Craft, Taste and Going From Fun Uncle to the Responsible Parent
Tariq Hassan
Former CMO of Petco and Chief Customer Experience Officer at McDonald's
McDonald's (former), Petco (former)
Episode: Tariq Hassan on Fear, Failure, and Brand Role in Culture
Reed Hastings
Former CEO of Netflix; executive chairman; real estate developer at Powder Mountain
Netflix, Powder Mountain, Anthropic (board)
Episode: Reed Hastings on Unlearning Leadership: From Netflix to the Mountain

Hosts

Rishad Tobaccowala
Host with a focus on unbossing leadership, corporate culture, and governance in AI-enabled organizations; associated with the podcast's themes of resilience, curiosity, and people-first strategies.
Drew Ianni
Co-host bringing practical perspectives on branding, craft, stakeholder management, and cross-functional collaboration; emphasizes the blend of human craft and data-driven rigor in leadership.

Chart Rankings

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Talking Points

Recent interactions between the hosts and their guests.

Jim McCann on His First Flower Shop, 1-800-Flowers, and Firing Himself
Q: What does unbossing mean to you in daily practice?
Unbossing means delegating and removing bottlenecks so you can focus on high-impact work like writing and future planning, while others with the right skills take over operational functions, enabling faster adaptation and innovation.
Jim McCann on His First Flower Shop, 1-800-Flowers, and Firing Himself
Q: What prompted you to replace yourself as CEO and how did you manage that transition?
It was incredibly difficult; he had previously stepped down once due to family illness, but ultimately brought in a strong successor with board support to accelerate the company's evolution and re-tune leadership to fit the next phase, particularly around technology and AI readiness.
Jim McCann on His First Flower Shop, 1-800-Flowers, and Firing Himself
Q: I know you've told this story a million times, but can you tell us a little bit about the founding of 1-800-Flowers?
Jim describes starting with one shop on the Upper East Side, bootstrapping without traditional capital, and gradually expanding through family-driven learning and a focus on relationship-building rather than just selling flowers.
David Kenny on Leading Through Uncertainty, Managing vs. Governance, and Why Curiosity Beats Expertise
Q: How do you navigate uncertainty and fear at different levels of an organization?
He stresses accepting fear as a practical motivator, anchoring decisions to true north values, and designing systems that empower the front line while maintaining a clear direction and rapid course correction when needed.
Tariq Hassan on Fear, Failure, and Brand Role in Culture
Q: How should brands engage with youth today while staying authentic?
Brands should unlearn some control and collaborate with creators, letting fans reinterpret the brand in their own authentic ways, and use data to surface cultural signals rather than forcing a top-down narrative.

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Frequently Asked Questions About Unbossing

What is Unbossing about and what kind of topics does it cover?

The show centers on reinventing leadership for chaotic times, hosting fearless executives from business and tech to discuss what they've unlearned to succeed in a rapidly changing world. Conversations frequently cover leadership philosophy, governance versus management, culture, and the human side of scaling—balancing curiosity, psychological safety, and values with rapid technological shifts such as AI. Notable throughlines include unbossing hierarchical norms, empowering frontline teams, and treating diversity and inclusion as strategic imperatives, all while exploring how brands and organizations stay relevant in a data-driven era. The format often features candid reflections on fear, failure, and courageous decision-making, with practic... more

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Which podcasts are similar to Unbossing?

These podcasts share a similar audience with Unbossing:

1. The Artificial Intelligence Show
2. Freakonomics Radio
3. Pivot
4. The Prof G Pod with Scott Galloway
5. David Senra

How many episodes of Unbossing are there?

Unbossing launched 4 months ago and published 7 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact Unbossing?

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What guests have appeared on Unbossing?

Recent guests on Unbossing include:

1. Sarah Personette
2. Jim McCann
3. David Kenny
4. Jim Lesser
5. Tariq Hassan
6. Reed Hastings

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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