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’t plan to become an entrepreneur. After layoffs, burnout, and a side experiment o...
Apr 29, 2026•41 min•Ep. 180
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 performance problems are solved by replacing people. Instead, the real leverage comes from coaching,...
Apr 15, 2026•45 min•Ep. 179
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 help leaders operate with greater clarity and intent. Misty shares her journey fro...
Apr 01, 2026•40 min•Ep. 178
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 declining economic mobility and generational uncertainty to the role ...
Mar 18, 2026•46 min•Ep. 177
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 back. Nicole breaks down the SPACE framework, explains why activity metrics cr...
Mar 04, 2026•33 min•Ep. 176
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 of AI tools or unsure where to start, this episode will help you reframe the conversation. This isn’...
Feb 18, 2026•30 min•Ep. 175
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 craftsmanship over scale, long-term thinking over short-term returns, and integrity over imitati...
Feb 04, 2026•44 min•Ep. 174
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 work, even as his scope of leadership expanded. In this episode, we explore how Andrew is now appl...
Jan 21, 2026•47 min•Ep. 173
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 Neural Lab—a platform that turns basic webcams into powerful tools for gest...
Jan 14, 2026•36 min•Ep. 172
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 shaping the future of space startup investment. Maureen began her career in nuclear engineering, earn...
Dec 30, 2025•40 min•Ep. 171
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 an age of continuous transformation. In this episode, we go behind the scenes of their book and e...
Dec 17, 2025•37 min•Ep. 170
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-making. He previously served as Head of Product at Atlassian, where he helped scale Jira Align after sel...
Dec 03, 2025•47 min•Ep. 169
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 about roles in an automated world, Cass shares an honest look at how she’s bringing people along on a transformation journey—with curiosity, experimentation, and heart. We discuss her pivotal decision t...
Nov 19, 2025•46 min•Ep. 168
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 corporate history. After selling his third startup to IBM in 2010, Phil was asked to transform how IBM’s teams worked using design thinking and agile. That effort reshaped the experience of over 400,000 em...
Nov 05, 2025•43 min•Ep. 167
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. We explore how founders can unlearn generic marketing advice, clarify their message, and activate their strategy through one often-overlooked asset: their homepage. Anthony brings practical frameworks, ...
Oct 22, 2025•50 min•Ep. 166
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 biological. From the neuroscience of loneliness to surprising acts of generosity in mice and minnows, we explore how your brain interprets social disconnection as a threat, and why a full calendar of Zoom ca...
Oct 08, 2025•40 min•Ep. 165
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 leading people strategy at companies like Microsoft, ThoughtWorks, and Equal Experts, Theresa has helped organizations across Europe and Asia grow not just fast, but gracefully. In this episode, we dive int...
Sep 24, 2025•40 min•Ep. 164
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 million to $30 billion, Ron has spent more than two decades helping ultra-wealthy families align their capital with causes that matter. In this episode, Ron shares how the collapse of Drexel Burnham shaped ...
Sep 10, 2025•50 min•Ep. 163
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 co-author of Orchestrating Connection , David breaks down the silent skills that build trust, activate communities, and transform the way we gather. David Homan is the founder and CEO of Orchestrated Conne...
Aug 27, 2025•42 min•Ep. 162
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 sex trafficking. He is the true-life inspiration behind the Sound of Freedom movie and the author of The Sound of Freedom: True Stories That Inspired the Film , offering a raw, unfiltered look at what it ...
Aug 13, 2025•48 min•Ep. 161
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 mentors build lasting companies and vibrant startup ecosystems. Brad has spent over three decades cultivating startup communities by putting people before profit and helping others without expecting anything ...
Jul 30, 2025•47 min•Ep. 160
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 environments. David’s leadership journey spans over 15 years of agile transformation, commercial growth, and organizational design. He’s held executive roles at Kin + Carta, The App Business, ThoughtWorks, and Scot...
Jul 16, 2025•49 min•Ep. 159
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, marketing, and demand generation. Alistair’s work focuses on data-driven innovation and human behavior. He co-authored Just Evil Enough: The Subversive Marketing Handbook , a playbook for bending the r...
Jul 02, 2025•45 min•Ep. 158
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 truths of building a company with intention. Jamie Dobson is the co-founder and former CEO of Container Solutions , a consultancy helping organizations adopt cloud-native technologies. A self-proclaime...
Jun 18, 2025•37 min•Ep. 157
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 intelligence has transformed how he works, lives, and thinks. From debugging code to managing projects and planning weekends with his son, Jeremy has embraced AI as a true co-pilot. His story isn’t about...
Jun 03, 2025•45 min•Ep. 156
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 mindset shifts needed for real change. Today, I’m excited to welcome John Avrett , former U.S. diplomat, aerospace and electrical engineer, and now Founder and CEO of Hive Modular. With past roles in the U.S. ...
May 21, 2025•39 min•Ep. 155
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 Transcend. With over 10 books and years of business leadership, Faisal shares how life, purpose, and challenges have shaped his journey of learning, growth, and helping others. Known for books like Everything...
May 07, 2025•35 min•Ep. 154
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 Shifts . With over 20 years as a behavioral scientist and 4-time entrepreneur, Ja-Naé has guided organizations, governments, and communities through future-focused transformation. Recognized by outlets...
Apr 23, 2025•46 min•Ep. 153
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 of Prodotto Collective, a product visionary, transformational leader, and someone who truly understands what it takes to build beloved products and high-performing teams. Francesca was the Chief Product ...
Apr 09, 2025•44 min•Ep. 152
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 success. Her work with Formula 1 , where she studied behavior and culture within teams to develop comprehensive strategies that enhance performance, along with her contributions to Leiden University , and ...
Mar 26, 2025•39 min•Ep. 151
