The Meg and Amy Show
Join best friends Meg Bear and Amy Wilson on The Meg and Amy Show – a podcast for big-picture thinkers who are ready to challenge the status quo. As former tech executives and seasoned business leaders, Meg and Amy have spent decades leading through change. Now, they’re joining forces to break down the trends they’ve lived and helped shape.
Episodes
December 5, 2025 • 68 mins
Finland – Universal Basic Income Pilot🚀 THE CASE FOR GIVING PEOPLE MONEY: UBI expert Scott Santens reveals why the most radical idea in economics might be the simplest - just give people cash. Discover how Alaska has proven this works for 40+ years, why his crowdfunded basic income changed everything he thought about work, and what happens when we shift from survival mode to abundance thinking.
⏰ TIMESTAMPS:
00:00 Introduction:...
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November 21, 2025 • 58 mins
🔄 What happens when two leaders with completely different upbringings join forces? In this deeply personal episode, Amy and Meg explore how their vastly different childhoods - one marked by stability and support, the other by constant change and scarcity - shaped their leadership styles, decision-making approaches, and the way they navigate challenges today.
⏰ TIMESTAMPS:
00:00 Introduction & Banter including Meg's Vietnam trav...
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November 20, 2025 • 60 mins
What would you build if you were creating a product organization from scratch in 2030? SugarCRM Chief Product Officer Maksim Ovsyannikov joins Amy and Meg to explore how AI is fundamentally reshaping product development, design thinking, and organizational structures.
From "very little user experience" as a value proposition to why QA is more critical than ever in probabilistic systems, this conversation challenges everything yo...
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November 7, 2025 • 57 mins
🚀 After 24 episodes and conversations with 20+ transformation leaders, Amy reveals the AI Transformation Maturity Model that synthesizes everything we've learned. Discover how to get ahead of AI transformation instead of being a victim of change, why this moment offers the biggest career opportunity in decades, and how to build the change agility that separates thriving organizations from struggling ones.
This episode weaves toge...
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October 31, 2025 • 71 mins
🚀 INVENTING THE AI-FIRST OPERATING MODEL: HubSpot CEO Yamini Rangan reveals how she completely scrapped her $40B company's roadmap and rebuilt it AI-first. Learn how to pivot from volume to conversion, navigate the decline of SEO, and lead transformation when no one has the answers.
⏰ TIMESTAMPS:
00:00 Introduction: From Reading Every Book in the Library to CEO
05:00 Moving to the US: The Airport Story and Finding Her Voice
15:...
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October 17, 2025 • 62 mins
🚀 Why "I Don't Know Yet" Is the Most Valuable Leadership Skill in the AI Age: Dr. Kirstin Ferguson reveals how expertise becomes your biggest enemy and why intellectual humility beats certainty every time.
⏰ TIMESTAMPS:
00:00 Introduction & Antarctica Adventures
02:06 Welcome to Dr. Kirstin Ferguson
04:38 Why Travel Reduces Blindspots
05:49 The UK Post Office Scandal: When "The Computer Is Always Right"
08:44 How Success Becomes ...
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October 10, 2025 • 55 mins
🚀 BREAKING OUT OF THE DEFAULT MALE WORLD: Meg and Amy reveal the hidden challenges of female leadership in a world designed by and for men. Learn how to navigate bias, own your power, and redefine what leadership looks like in the AI era in this raw and empowering conversation.
⏰ TIMESTAMPS:
00:00 Introduction to Female Leadership Challenges
05:55 WNBA Success and Equal Pay Movement
07:06 Fiji Simo's Historic OpenAI Appointment
0...
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October 3, 2025 • 60 mins
Angela Le Mathon reveals how HR leaders can move beyond the "skills data trap" to drive real business outcomes with AI. Learn how to speak the language of business, avoid the employee experience trap, and design AI-native organizations in this thought-provoking conversation on business transformation and leadership.
**🔑 KEY INSIGHTS:**
Skills data works for talent marketplaces but doesn't drive business outcomes
HR must ...
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September 26, 2025 • 55 mins
🌐 Most companies are approaching AI adoption backwards. While executives push top-down strategies, the real innovation is happening in the trenches.
Seth Wylie reveals why successful AI transformation starts with the people already experimenting - not training programs or executive mandates.
**🔑 KEY INSIGHTS:**
- Why mandatory AI training kills experimentation before it starts
- The one question that gets everyone talking: ...
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Episode 18 | Sangeet Paul Choudary: The Winning AI Strategy – Reshuffling Systems, Not Adding Smarts
September 19, 2025 • 65 mins
Meg and Amy welcome Sangeet Paul Choudary, author of Reshuffle. Their discussion explores how companies must evolve beyond traditional operating models to embrace structural change. Sangeet highlights the often-overlooked role of coordination costs in organizations, how AI can help manage these costs, and why rethinking business models is central to AI transformation. He also shares insights on creating structural optionality and r...
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September 12, 2025 • 62 mins
This week on The Meg & Amy Show, Meg and Amy welcome fitness expert and wellness coach Angie Mercado. Angie shares her decades of experience helping women find joy in movement, balance demanding lives, and stay consistent with their health goals even when work, travel, and family make it difficult.The conversation explores breaking free from the “one-hour workout” mindset, strategies for staying fit while traveling, the importance ...
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September 5, 2025 • 62 mins
In the business of software, how you charge is just as important as what you build. In this episode of The Meg & Amy Show, Meg and Amy sit down with Kyle Poyar, creator of Growth Unhinged and one of the leading voices in SaaS pricing and monetization. Kyle coined the term Product-Led Growth, and in this conversation he unpacks the seismic shifts happening in pricing – from the rise of hybrid and usage-based pricing to the new front...
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August 28, 2025 • 57 mins
This week, Meg and Amy sit down with John Wookey, a legend in the enterprise software world, to explore the power of mission and values in organizations, why transparency is essential for strong leadership, and how AI is reshaping the way we work. John also reflects on the importance of unlearning outdated structures to foster innovation, and shares advice for first-time people managers.
John's Strategy 101 Paper: https://www.link...
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August 22, 2025 • 63 mins
In this episode of The Meg and Amy Show, Meg and Amy get personal, opening up about their individual health journeys and what inspired them to make wellness a priority. They share the turning points that pushed them to take action, what they discovered through their initial health scans, and the lifestyle changes they’ve embraced — from fitness routines to nutrition to smart supplementation.
Submit questions for future Leadership ...
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August 21, 2025 • 62 mins
Join Meg, Amy, and Gustavo Alba as they dive into the new rules of executive search, the evolution of talent profiles in the AI economy, and the new characteristics required for transformational leadership. Listen in to learn more about the challenges of navigating AI transformations in legacy companies, the need for bravery and vision in leadership, and survival tips for CEOs in the AI era.
Heidrick and Struggles | https://www.h...
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August 8, 2025 • 60 mins
In this episode of The Meg and Amy Show, Meg and Amy are joined by Usman Sheikh for an insightful conversation on the transformation of business models — from legacy organizations to the rise of new players. They explore the critical role of leadership in guiding organizations through disruption, the human impact of large-scale change, and why building personal agency is essential for thriving in today’s rapidly evolving world of w...
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August 1, 2025 • 48 mins
In this episode, Meg and Amy discuss the evolving landscape of organizational design and business models. They explore the complexity of communication in growing organizations, the need for redesigning structures to adapt to new technologies, and so much more. The conversation emphasizes the importance of curiosity, flexibility, and understanding the core principles of business as organizations navigate these changes.
Submit quest...
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July 25, 2025 • 55 mins
In this episode, Meg and Amy sit down with Kieran Snyder for a candid, high-impact conversation about leadership, life, and what it really means to be an AI-first company. They discuss why data storytelling matters more than ever, what authentic allyship looks like beyond performative gestures, and how to lead in the age of AI.
Submit questions for future Leadership Corner segments to: amywilsonadvisor@gmail.com
Resources & Ment...
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July 18, 2025 • 60 mins
In this episode, Amy takes center stage to dive into a topic we all need to talk more about – financial independence. Meg and Amy unpack how your upbringing and early money messages shape your relationship with finances, why your financial state is deeply tied to your mental well-being, and how to shift your mindset from survival to intention.
Submit questions for future Leadership Corner segments to: amywilsonadvisor@gmail.com
R...
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July 11, 2025 • 57 mins
In today’s episode, Meg and Amy welcome Jen Morrow to the show! Jen shares practical tips for building a board ready business case with a powerful story, aligning stakeholders around a shared vision, and how to move forward when the answer is "no".
Submit questions for future Leadership Corner segments to: amywilsonadvisor@gmail.com
Connect with Meg, Amy, and Jen
Jen's LinkedIn: https://www.linkedin.com/in/jenmorr/
Instagram:...
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