Unlearn

AI investment can give people new tools without changing the way the business performs. Leaders need to explain what should improve, help teams develop new ways of working, and ensure their goals and incentives support that change. In this episode, Melanie Steinbach , whose people leadership experience spans McDonald’s, Cameo, and MasterClass, joins me to explore how organizations turn AI investme...

AI capabilities are advancing quickly, but changing how people work takes time. Leaders need to give teams the confidence to experiment while protecting sensitive information and keeping responsibility clear. How they manage that balance shapes whether AI leads to better business outcomes. In this episode, Cassandra Pratt , CHRO at Progyny , and John Marcante , former Global CIO of Vanguard , join...

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. In our conversation, John and I explore why AI investment needs to change how work gets done. John shar...

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 Africa and Central America. Those experiences shaped how he thinks about resilience, problem-solving, and...

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 eventually sold the company to Pluralsight. Now, as CEO and co-founder of Cuttable, he’s back at the begin...

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 Nast into product management, commercial leadership, and eventually product operations. Denise shares how...

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 software. Drawing on her background in anthropology, economics, organizational design, and product leader...

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. After hearing from readers who wanted another way to experience the book, Barry spent four days in the st...

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 , Chief Marketing Officer at Nobody Studios . Eric shares how a seventh-grade summer teaching himself to p...

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 episode of the Unlearn Podcast , I’m joined again by John Cutler , product thinker, systems explorer, a...

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 talk about why AI raises the stakes for executive judgment. AI can remove friction, speed up work, and t...

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 organizational performance, but this conversation goes far beyond marketing or AI tactics. Drawing on ideas from his...

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 such as Volvo giving away the seatbelt patent, Tony’s Chocolonely opening its ethical supply chain to c...

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. This conversation is about the courage to simplify—and why that’s far harder (and more powerful) than i...

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 spent her career solving business problems through people. But she challenges a core assumption: that...

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 productivity narrative and dig into something far more powerful: how AI can sharpen decision-making, surface bett...

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 question: can modern capitalism create broader opportunity, stronger communities, and more inclusive ownership...

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 alone doesn’t create performance — and how hidden friction inside systems, culture, and decision-makin...

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 competitive edge isn’t automation, but judgment at speed. If you’ve been overwhelmed by the explosion...

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 companies. For nearly 40 years, Gerry has gone against almost every rule of modern business — choos...

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 decade isn’t status, but challenge: new teams, unfamiliar problems, and the chance to stay close to th...

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 to startup founder began with a pivotal moment during the pandemic. What started as a side pro...

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 space-focused VC firm, she invests globally in technologies pushing the boundaries of what’s possible —and s...

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 know through his work at McDonald’s—they’ve co-authored The Octopus Organization , a guide for thriving...

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 co-founder of The Uncertainty Project , a community for product leaders focused on better decision-maki...