PODCAST · business
Unlearn
by Barry O'Reilly
The way to think differently is to act differently and get comfortable with being uncomfortable. For business leaders, entrepreneurs, managers and anyone who wants to improve how they work and live: Welcome to the Unlearn Podcast. Host Barry O’Reilly, author of Unlearn and Lean Enterprise seeks to synthesize the superpowers of extraordinary individuals into actionable strategies you can use—to Think BIG, start small and learn fast, and find your edge with excellence.
Episodes
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Why AI Adoption Is No Longer Enough to Create Business Value with John Marcante
Making technology faster does not automatically make the business better. John Marcante spent 28 years at Vanguard, including serving as Global CIO and leading its high-net-worth and advice business. As Deloitte’s U.S. CIO-in-Residence, he works with senior technology leaders navigating change.…
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When AI Makes Development Faster, What Should You Build with Ciaran Cosgrave
When building gets easier, choosing what to build becomes even more important. Ciaran Cosgrave is CEO of Nearform, a global AI-native engineering company for the enterprise. Before moving into entrepreneurship and technology, he spent the first decade of his career running refugee camps across...
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From SaaS Scale to AI Startups: What We Had to Unlearn to Build Again with Sam Kroonenburg
Building AI startups can make past success a liability when it convinces you that the way you built before is the way you should build next. Sam Kroonenburg knows what it feels like to build at scale. He co-founded A Cloud Guru, helped grow it into a business serving millions of learners, and...
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Building Better Products Through Better Product Operations with Denise Tilles
AI can accelerate a strong operating model, but when decision rights, incentives, or data are already unclear, it can make the mess spread faster. In this episode, I sit down with Denise Tilles, a leading voice in product operations, to unpack how her career moved from editorial work at Condé…
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Redesigning Leadership for the Age of AI Agents with Tatyana Mamut
AI is forcing us to rethink a question most organizations have avoided for years: what is uniquely valuable about human work when intelligence itself is no longer scarce? Tatyana Mamut, CEO of Wayfound and former CPO of Nextdoor, joins me to explore AI adoption through a lens that goes beyond...
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Exclusive Audiobook Preview for Artificial Organizations
Before leaders can redesign their organizations with AI, they have to reconsider how they personally think, work, and make decisions. In this special episode of Unlearn, Barry O’Reilly shares the opening chapter of the audiobook edition of Artificial Organizations, narrated in his own voice.…
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Why AI Makes Great Systems Matter Even More with Eric Baxley
AI is making it easier than ever to build products, automate work, and scale ideas. The challenge is no longer access to technology. It's designing the systems, stories, and customer understanding that turn AI into real business outcomes. In this episode of Unlearn, I'm joined by Eric Baxley…
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Judgment in the Age of AI with John Cutler
AI is changing how leaders think, decide, and work with their teams. But as John Cutler points out in this conversation, the real shift is not simply about faster answers or more productivity. It is about becoming more aware of the judgment systems we already use, often without noticing. In this...
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Unlearning Executive Judgment: Building Decision-Making Muscles in the Age of AI with Jim Highsmith
Jim Highsmith has been thinking about decision-making for a long time. When he wrote Agile Project Management in 2004, he went looking for practical guidance on decision-making in the project management literature and found very little. That gap matters even more now. In this episode, Jim and I...
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The Frequency Era with Chris Walker
AI is changing how work gets done — but more importantly, it’s changing how people understand their value, identity, and ability to navigate uncertainty. That’s one of the reasons I wanted Chris Walker on the show. Chris has spent years helping companies rethink growth, systems, and…
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Incorruptible with Eric Ries
Incorruptible with Eric Ries What if the companies that last the longest are the ones building enough trust that people want to keep participating in them? That’s the idea behind this conversation with Eric Ries — entrepreneur, author of The Lean Startup, and now Incorruptible. Through stories…
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Do Less, Win More: How Niche Focus Cuts Through the Noise with Tas Bober
Most people think growth comes from doing more—more services, more offers, more complexity. But in this episode, I sit down with Tas Bober, who did the exact opposite. She stripped everything back, focused on one problem, and built a business so clear people can describe it in a single sentence....
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Solve Business Problem with People with Melanie Steinbach
Most leaders think AI is a technology shift. It’s not. It’s a behavior shift. In this episode, I sit down with Melanie Steinbach—former Chief HR Officer at McDonald’s, Cameo, and MasterClass—to unpack what’s actually changing inside organizations as AI becomes embedded in how we work. Melanie has...
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Stop Chasing Productivity—Start Thinking Better with AI with Misty Shafer Sterne
AI isn’t changing the game—it’s exposing how you think. In this episode, I sit down with Misty Shafer Sterne, Vice President of Commercial Technology at American Airlines, to explore what it really takes to lead with AI inside a complex, high-stakes organization. We go beyond the usual…
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Capital Evolution: The Future of Business and AI
What role should businesses play in society today? In this episode of the Unlearn Podcast, I sit down with investor, ecosystem builder, and Foundry Group co-founder Seth Levine to explore how capitalism itself may be evolving. Seth’s latest book, Capital Evolution, examines a fundamental…
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Frictionless, Artificial Organizations: Measuring What Matters in the Age of AI
AI can now generate code in seconds. Deployment pipelines are faster than ever. And yet, many teams still feel slow. In this episode, I sit down with Nicole Forsgren, world-renowned researcher, co-author of Accelerate, and Senior Director of Developer Intelligence at Google. We explore why speed...
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Artificial Organizations: Judgment at Speed in the Age of AI
AI isn’t about productivity. It’s about presence. In this special episode, the tables turn and I’m interviewed by Sham Colegado about my new book, Artificial Organizations. We explore why 95% of AI projects fail, why executives don’t want more tools — they want their life back — and how the real...
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Unlearning Perfectionism While Building Products That Last with Gerry Khouri
What if success isn’t about scaling faster, shipping more, or chasing perfection — but about building something so honest it can last for generations? In this episode, I sit down with Gerry Khouri, Founder & Managing Director of Bufori, one of the world’s longest-running handcrafted automobile...
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AI Productivity for Executives: Skyscanner CTO Andrew Phillips
From graduate engineer to CTO, Andrew Phillips’ 16-year journey at Skyscanner is a story of continuous reinvention. He didn’t chase titles—he chased growth, deliberately stepping out of his comfort zone and unlearning the habits that no longer served him. What’s kept him at the company for over a...
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How Is Visual Intelligence Redefining Human-AI Interaction with Sherry Chang
What if machines could truly see and understand how we move? In this episode, I sit down with Sherry Shang, CEO and co-founder of Neural Lab, a company reimagining how we interact with technology through visual intelligence AI and gesture-based interfaces. Sherry’s journey from Intel technologist...
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Investing In Space with Maureen Haverty
Today’s guest is someone I first came across on the Irish People in VC list—and I’m really glad I reached out. Because it turns out Maureen Haverty has one of the most fascinating jobs you can imagine: helping build the future of space. As a Principal at Seraphim Space, the world’s leading...
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The Octopus Organization with Jana Werner & Phil Le-Brun
Back when I first worked with Jana Werner at Tesco Bank, I saw firsthand how a crisis could be a crucible for innovation and transformation. Her ability to unlock potential in even the most challenged teams was unforgettable. Now, teaming up with Phil Le-Brun—a transformational leader I came to...
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What Truly Decisive, Agentic Organizations Are Doing? – Steve Elliott
In this episode of The Unlearn Podcast, Barry O’Reilly is joined by Steve Elliott, a serial entrepreneur, product leader, and investor with two decades of experience advising high-growth companies. Steve is the founder of Dotwork, an AI-driven platform that connects strategy to execution, and...
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The Human Side of AI: How HR Can Lead the Transformation with Cass Pratt
In this episode of the Unlearn Podcast, I sit down with Cass Pratt, Chief Human Resources Officer at Progyny, to explore how HR is evolving into a design discipline that blends human connection with AI-powered productivity. From building bots to boost employee experience to reshaping how we think...
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How to Create Irresistible Change for Business Transformation with Phil Gilbert
When most leaders think about transformation, they reach for tools and tactics. But real, lasting change doesn’t start with new methods—it starts with culture. In this episode, I sit down with Phil Gilbert, the former General Manager of Design at IBM, who led one of the boldest reinventions in...
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How to Clearly Position What You Do with Anthony Pierri
When it comes to product positioning, clarity isn’t just a communication tool—it’s a strategic advantage. In this episode, I sit down with Anthony Pierri, co-founder of FletchPMM, a product marketing consultancy that’s helped over 400 B2B software startups discover and sharpen their positioning.…
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Why Brains Need Friends with Dr. Ben Rein
In today’s hyper-connected world, many of us are experiencing a paradox—more digital interactions, but deeper loneliness. In this episode of Unlearn, I sit down with Dr. Ben Rein, neuroscientist and author of Why Brains Need Friends, to unpack why human connection isn’t just emotional—it’s...
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Scaling HR For Growth with Grace with Theresa Cantwell
What happens when you stop treating HR as a back-office function and start designing it as a competitive advantage? Theresa Cantwell, Strategic HR Consultant and Director at GSD HR Consulting, believes scaling a company shouldn't mean burning out your team—or yourself. With nearly two decades...
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How Family Offices Are Disrupting Venture Capital and Private Equity with Ron Diamond
What happens when you stop chasing returns and start investing in purpose? Ron Diamond, Founder and Chairman of Diamond Wealth, believes the future of finance isn’t just about building wealth—it’s about what that wealth can do. As a trusted advisor to over 100 family offices ranging from $250...
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The Power of Real Conversations with David Homan
What if networking wasn’t about schmoozing but about being seen? David Homan joins me to unlearn the myths of traditional networking and share how vulnerability, deep listening, and small group connection can foster truly meaningful relationships. As a master connector, classical composer, and...
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The Sound of Freedom and Healing Trauma with Paul Hutchinson
Paul Hutchinson’s life story reads like a thriller, but his mission is deeply real and urgent. Once a multi-billion dollar fund manager, Paul transformed his life to become an undercover operative, leading more than 70 rescue missions across 15 countries to free thousands of children trapped in…
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Give First and the Ripple Effect of Generosity with Brad Feld
What if generosity—not hustle—is your greatest competitive advantage? Brad Feld—co-founder of Foundry Group, Mobius Venture Capital, and startup accelerator Techstars—joins Barry to explore the transformative philosophy of “Give First,” a mindset that’s reshaped how founders, investors, and…
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Why AI-First Digital Product Consultancies Will Win Big with David Tuck
What if becoming a better leader meant letting go of being the expert? In this Unlearn episode, I’m joined by David Tuck, Chief Executive of Waracle, for a thoughtful and human-centered conversation on the mindset shifts required to lead high-performing teams in complex, fast-changing…
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Bold Go-To-Market Tactics: Just Evil Enough to Win with Alistair Croll
What if the biggest risk in your business isn’t building the product but realizing no one wants it? In this Unlearn episode, I’m joined by Alistair Croll, technologist, entrepreneur, and bestselling author of Lean Analytics, for a candid and clever conversation on rethinking product development,...
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Visionaries, Rebels, and Machines: Getting the Best of All with Jamie Dobson (Explicit)
Today on the Unlearn podcast, we welcome Jamie Dobson, technologist, entrepreneur, and a leader known for building systems that connect innovation with purpose. He joins us to share a deeply reflective journey: spanning childhood curiosity, extreme programming, leadership challenges, and the hard...
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What Happens When You Go All-In in Work and Life on AI with Jeremy Shankle
Today on the podcast, we welcome Jeremy Shankle, full-stack engineer, AI strategist, and early adopter of automation tools across work and life at Nobody Studios. With decades of experience in web development, startup leadership, and product strategy, Jeremy shares how going all-in on artificial...
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The Future of Housing and Modular Home Building with John Avrett
Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast. Contact here: https://bit.ly/contact-barryoreilly ____________________________________________________________ Welcome to UNLEARN, the podcast where we talk about bold ideas, fresh thinking, and the…
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The New Science of Self-Actualization for Founders to Reinvent Identity & Find Meaning - Faisal Hoque
Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast. Contact here: https://bit.ly/contact-barryoreilly ____________________________________________________________ Today on the podcast, we welcome Faisal Hoque, author, entrepreneur, and thinker behind...
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Unlearning Legacy Systems to Build Antifragile AI Operating Models with Ja-Naé Duane
Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast. Contact here: https://bit.ly/contact-barryoreilly ____________________________________________________________ Today on the podcast, we welcome Ja-Naé Duane, systems thinker, innovator, and author of Super...
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From Fashion to Real Estate, Unlearning to Realign Purpose and Scale with Francesca Cortesi
Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast. Contact here: https://bit.ly/contact-barryoreilly ____________________________________________________________ Today on the Unlearn Podcast, I’m thrilled to be joined by Francesca Cortesi, CPO and Founder…
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The Neuroscience of High-Performing Teams for Leaders to Achieve Workplace Success | Dr. Marcia Goddard
Welcome back to the Unlearn podcast! Today, we're exploring neuroscience with Dr. Marcia Goddard, a top neuroscientist and high-performance expert. As the founder of Brain Matters, a LinkedIn Top Voice, TEDx speaker, and a Neuroscientist. She's known for making science practical for business...
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Why Playing Too Small Is Stopping Your Finance Career Growth with Kristie Edling-Day
Welcome to UNLEARN, the podcast where we will discuss the transformative journeys, innovative tactics, and the pivotal mindset shifts necessary for authentic progress and development. Today, I'm thrilled to welcome Kristie Edling-Day, the current Executive Vice President and Chief Information...
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How to Build a Viral App by Finding Untapped Niches for Explosive Growth | Crystal Gonzalez
Welcome to UNLEARN, the podcast where we explore the transformative experiences, strategies, and mindset shifts essential for true innovation and growth. Today, I’m honored to host Crystal Lee Gonzalez, a trailblazer in strategic growth and innovation across Southeast Asia. Born and raised in the...
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How AI is Changing Product Management Forever with Diana Stepner
Welcome to UNLEARN, the podcast where we explore the stories, strategies, and mindset shifts that drive real innovation and growth. Today, I’m glad to be joined by Diana Stepner, a true trailblazer in the world of product management and people-centered leadership. A Silicon Valley native, Diana…
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How the Attention Economy is Redefining Traditional Marketing with Emily Ross
Welcome to the UNLEARN Podcast! Today, we’re joined by Emily Ross, co-author of Just Evil Enough and a leader in brand strategy and creativity. With a career spanning tech innovation, marketing, and even circus performance, Emily approaches challenges from unconventional angles. As Director of...
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How Product Managers Can Avoid Startup Failures and Drive Growth with John Cutler
Welcome to the UNLEARN Podcast! Today, we’re joined by a thought leader and prolific voice in product management and organizational design, John Cutler. With a unique ability to navigate the “beautiful mess” of product development, John has spent his career exploring the complex overlaps of...
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Proven Strategies to Create Accountability Without Agency with Lee Vorthman
Welcome to the UNLEARN Podcast! Today, we’re joined by Lee Vorthman, Vice President of Strategic Security Initiatives at Oracle. Lee leads a global team to protect and strengthen Oracle's operations. He is also a Global CISO Advisory Board Member at HMG Strategy and an Advisory Board Member for...
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Why Unlearning Cultural Norms Is Essential for Thriving in Global Leadership with Ani Filipova
Welcome to the UNLEARN Podcast! Today, we’re joined by an inspiring leader in global banking and transformation, Ani Filipova. With over two decades of experience, Ani has made her mark as a former international banking executive, setting up and managing three banks, including Citibank Bulgaria....
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Personalized: Customer Strategy in the Age of AI with David C. Edelman
Welcome to the UNLEARN Podcast! Today, we’re joined by a true pioneer in digital transformation and customer strategy, David C. Edelman. With over three decades at the forefront of marketing and digital transformation, David most recently served as Chief Marketing Officer at Aetna/CVS, where he…
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Ethical Strategies for Startup Leaders to Avoid Growth Hacking with Andy Budd
Mastering venture capital and ethical growth is essential for startup success. Today’s guest, Andy Budd, shares insights from his journey as Founder and CEO of Clearleft, Venture Partner at SeedCamp, and Founding Member of Adobe’s Design Circle. Andy has evolved from a designer to an investor and...
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ABOUT THIS SHOW
The way to think differently is to act differently and get comfortable with being uncomfortable. For business leaders, entrepreneurs, managers and anyone who wants to improve how they work and live: Welcome to the Unlearn Podcast. Host Barry O’Reilly, author of Unlearn and Lean Enterprise seeks to synthesize the superpowers of extraordinary individuals into actionable strategies you can use—to Think BIG, start small and learn fast, and find your edge with excellence.
HOSTED BY
Barry O'Reilly
CATEGORIES
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Frequently Asked Questions
How many episodes does Unlearn have?
Unlearn currently has 190 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Unlearn about?
The way to think differently is to act differently and get comfortable with being uncomfortable. For business leaders, entrepreneurs, managers and anyone who wants to improve how they work and live: Welcome to the Unlearn Podcast. Host Barry O’Reilly, author of Unlearn and Lean Enterprise seeks to...
How often does Unlearn release new episodes?
Unlearn publishes regularly with 190 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Unlearn?
You can listen to Unlearn on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Unlearn?
Unlearn is created and hosted by Barry O'Reilly.
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