Unlearn

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 beginning: finding customers, testi...

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 learning to work with revenue data, ...

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 leadership, Tatyana explains ...

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 studio bringing its ideas and stor...

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 program on an Atari 800 sp...

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, and Head of Product at Dotwork. W...

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 take on repeatable tasks, but it can ...

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 new book The Freq...

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 competitors, and Mary ...

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 it sounds.

Tas didn...

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 p...

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 better questions, and...

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?

Our conversation ranges from d...

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-making quietly holds teams bac...

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 ...

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 — choosing craftsmans...

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 the wor...

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 project in her living room became N...

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...