

Unlearn
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
Mentioned books

Aug 13, 2025 • 48min
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 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 takes to confront humanity’s darkest realities and bring hope to the most vulnerable.This episode goes far beyond heroism. We explore the complexities and personal costs of Paul’s work—from how his background in private equity uniquely positioned him to negotiate with traffickers, to the emotional and psychological toll of seeing trauma up close. Paul also shares vital lessons on protecting your children, what really works in combating trafficking, and why healing—beyond extraction—is the ultimate rescue.Some stories are tough to face but impossible to turn away from. Paul’s journey is a powerful reminder of resilience, transformation, and what true leadership means when you dare to engage with the hardest truths.Key TakeawaysTrauma Often Hides in Plain Sight: Early exposure to peer counseling revealed the silent prevalence of abuse and shaped Paul’s lifelong compassion.Leverage Unique Skills for Impact: Paul’s financial expertise uniquely positioned him to negotiate with traffickers and execute high-stakes rescue missions.Healing Requires Vulnerability: Emerging therapies like psilocybin can accelerate breakthroughs when used intentionally and safely.Meditation and Gratitude as Daily Practices: Far from clichés, these tools quiet the mind and strengthen authentic connection.Impact Extends Beyond Rescue: True change is about rehabilitation, restoring humanity, and creating ripple effects of hope.Material Success Without Meaning is Hollow: Relationships, purpose, and self-awareness are the real measures of a life well lived.Additional InsightsRedefine Success on Your Own Terms: Society pushes for more—money, power, status—but real fulfillment comes from understanding what truly matters to you.Embrace Compassion as a Leadership Skill: Genuine empathy transforms how you influence and inspire others.Healing is a Collective Journey: Trauma and recovery ripple beyond the individual to impact families and communities.Courage Requires Vulnerability: Facing your own shadows opens the door to deeper connection and transformation.Episode Highlights00:18 – Episode RecapPaul Hutchinson’s journey from multi-billion dollar fund manager to undercover operative rescuing trafficked children reveals a profound transformation—one fueled by confronting trauma, embracing empathy, and discovering the healing power of vulnerability and plant-based therapies.02:06 – Guest Introduction: Paul HutchinsonBarry introduces Paul Hutchinson, former private equity executive turned human trafficking rescuer and author of The Sound of Freedom, sharing raw stories behind one of the largest rescue missions and the personal toll it took.03:53 – Early Compassion & Peer LeadershipPaul reflects on how his early role as a peer counselor exposed him to hidden childhood traumas, planting the seeds of compassion that would later define his mission.14:34 – First Undercover Mission & The Rescue of 124 ChildrenPaul recounts negotiating with traffickers in Colombia, orchestrating a risky sting operation that rescued over a hundred children in a single day.23:59 – Processing Trauma with Psychedelic HealingThe conversation explores the emotional toll of undercover missions and how Paul and his team used plant-based therapies, like psilocybin, to process PTSD and reclaim their lives.39:10 – Meditation, Gratitude, and Spiritual ConnectionPaul shares his daily practice of meditation and gratitude as foundational tools for lasting transformation and alignment beyond material success.44:53 – Advice for Deep Healing and Self-TransformationPaul offers guidance for listeners on beginning their own journey of healing trauma through meditation, breathwork, and embracing vulnerability.47:26 – Closing ReflectionsPaul emphasizes the power of storytelling and awareness to inspire change, thanking Barry for amplifying the voices fighting modern slavery.Useful ResourcesThe Sound of Freedom by Paul Hutchinson Amazon BestsellerThe Sound of Freedom movie (inspired by Paul’s missions)Gabriel Maté – Author of The Myth of Normal (https://drgabormate.com)Web del x – Plant-based therapy education platform (https://webdelx.com)Webdelics - https://www.webdelics.com/Resources from GuestGet the first 3 chapters of Paul’s book for free: www.soundoffreedombook.comLiberating Humanity website: liberating-humanity.comChild Liberation Website: childliberation.orgYoutube - youtube.com/@liberatinghumanityInstagram - instagram.com/liberating.humanityFacebook - facebook.com/liberating.humanityTikTok - tiktok.com/@liberating.humanityLinkedIn - linkedin.com/in/paulhutchX - x.com/paulhutchinsonFollow Barry O’ReillyLinkedIn: https://www.linkedin.com/in/barryoreillyWebsite: https://barryoreilly.comFacebook: https://www.facebook.com/barryoreillyauthor/Twitter (X): https://x.com/barryoreillyInstagram: https://www.instagram.com/barryoreilly/

Jul 30, 2025 • 47min
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 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 in return.In this episode, he shares the mindset shifts that fueled Techstars’ global influence, how mentorship evolves from hierarchy to peer learning, and why sustainable success stems from playing the long game. A conversation full of clarity, candor, and challenge—for anyone rethinking what it means to lead, contribute, and create.Key TakeawaysGenerosity Fuels Growth: Giving without expectation of return builds stronger relationships, ecosystems, and companies.Mentorship is a Two-Way Street: The most impactful mentoring happens when both sides learn, grow, and give.Play the Long Game: Positive-sum, multi-turn thinking creates more meaningful and lasting impact than transactional wins.Know Yourself First: Deep self-awareness—not external success metrics—is the foundation of better leadership.Additional InsightsRedefine Success on Your Own Terms: Society pushes for more—money, power, status—but real fulfillment comes from understanding what truly matters to you.Build a Network of Givers: Shared values transcend geography. A global community built on generosity leads to collective resilience.Let Go of the Need for Control: Great mentors—and leaders—create space for co-creation, not dictation.Disconnect to Reconnect: Time away from constant input helps surface your clearest thinking and truest desires.Episode Highlights:00:00 – Episode RecapBrad Feld reframes mentorship as a shift from a one-way hierarchy to a peer-based relationship.01:48 – Barry Introduces Brad FeldBarry introduces Brad's influential work on startup communities and his philosophy of "Give First."03:12 – Startup Community OriginsBrad shares how the idea of startup communities became a global movement—challenging the belief that tech startups must be in Silicon Valley.12:54 – The Give First PhilosophyBrad explains why generosity, long-term thinking, and non-transactional relationships are foundational to resilient startup ecosystems.21:33 – Mentorship as Mutual GrowthA powerful story with mentor Len Fast reveals how Brad came to see mentorship as co-learning rather than knowledge transfer.27:27 – Knowing YourselfBrad emphasizes how self-awareness and personal growth are essential to leadership, especially in a world driven by reactive norms.34:48 – Creating Space for What MattersA candid discussion on disconnecting from external pressures, valuing inner reflection, and how time off helped Brad refocus on his values.41:47 – Redesigning RelationshipsBrad shares how he and his wife created structure and rules to prioritize their relationship—offering insight into the intersection of discipline and intimacy.45:41 – Final ReflectionsBrad closes with a message on leading through generosity, not transactions—and why playing the long game builds stronger companies and communities.Episode ResourcesBrad Feld on LinkedIn: Brad FeldFoundry Group on LinkedIn: Foundry GroupFoundry Group website: foundrygroup.comTechstars website: techstars.com

Jul 16, 2025 • 49min
Why AI-First Digital Product Consultancies Will Win Big with David Tuck
David Tuck, Chief Executive of Waracle, brings over 15 years of leadership experience in agile transformation and organizational design. He discusses the evolution from expert to inquirer, emphasizing the power of asking better questions as a leader. David shares insights on crafting supportive company cultures, particularly in hybrid environments. He underscores the importance of human relationships amidst AI advancements and explains how leaders should adapt to remain relevant in a tech-driven world.

22 snips
Jul 2, 2025 • 45min
Bold Go-To-Market Tactics: Just Evil Enough to Win with Alistair Croll
In this engaging discussion, Alistair Croll, a technologist and bestselling author, reveals bold insights on product development and marketing. He emphasizes the importance of proving demand before perfecting features. Alistair introduces the 'fluency equation,' highlighting how consumer desire can be influenced by reducing complexity. Using clever examples like Burger King's marketing tactics, he encourages subversive creativity in strategy. He also addresses the challenges leaders face in leveraging AI, urging a shift in mindset for growth in a rapidly changing landscape.

Jun 18, 2025 • 37min
Visionaries, Rebels, and Machines: Getting the Best of All with Jamie Dobson (Explicit)
Jamie Dobson, a technologist and former CEO of Container Solutions, navigates a compelling journey from software engineering to conscientious leadership. He shares insights on transforming challenges into opportunities for growth. Key topics include the emotional toll of leadership, the fine line between ambition and failure, and the ethics of making tough decisions, especially during redundancies. Jamie emphasizes the importance of self-reflection and supportive environments to empower teams in a tech-driven world while maintaining a commitment to integrity.

Jun 3, 2025 • 45min
What Happens When You Go All-In in Work and Life on AI with Jeremy Shankle
In this engaging discussion, Jeremy Shankle, a full-stack engineer and AI strategist at Nobody Studios, shares how embracing AI has transformed his work and personal life. He explores the drastic improvements in productivity by using AI tools like GPT-4 for coding and daily tasks. Jeremy emphasizes unlearning multitasking, which helps reduce context switching and enhances focus. He also touches on navigating time zone challenges in software development and the exciting future of specialized AI tools, showcasing their innovative potential for workplace efficiency.

May 21, 2025 • 39min
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 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. Air Force, U.S. Navy, and Department of State, John is leading a new wave of modular home building in the Philippines, tackling the global housing crisis with factory-made homes and smart design.John isn’t just a builder; he also loves solving big problems and making homes better for everyone. His journey from engineering and diplomacy to modular homes shows how thinking differently can help fix housing issues in new ways, especially by building smarter and faster in places that need it most.John has worked across engineering and global trade before starting his company to build homes in a new way. At his factory in the Philippines, his team makes modular houses using a process like a car factory, helping build faster and cheaper. He focuses on smart design and shipping, bringing homes to places that need them, while using skills from aerospace and diplomacy to guide his work.Key Takeaways:Fixing Housing Problems: John shares how factory-made homes can help more people.Starting a Business: What he learned from taking a big risk to follow his dream.Thinking Differently: Why new ways of thinking are key to solving old problems.Global Experience: How living and working abroad shaped his big ideas.Smart Building: How using a car-like factory process makes building homes faster.Additional Insights:Mixing Tech and Building: John shows how factory skills can improve home building.Working in New Markets: What it takes to build homes in places with big needs.Learning from the Past: How John’s old jobs help him find smart new ways to build.Solving Real Problems: How he uses design to make homes faster and cheaper.Adapting to Change: Why being open to new ideas helped grow his company.Join John Avrett as he shares how bold ideas, smart building, and global thinking can help solve housing needs and spark new ways to grow in today’s world.Episode Highlights:[00:10] - Episode Recap"John Avrett joins to talk about solving housing issues with modular homes and lessons from past careers."[01:38] - Guest Introduction: John Avrett"John is an ex-aerospace engineer and U.S. diplomat now building smart, factory-made homes in the Philippines."[04:48] - Museum Visit Sparks a Big Idea"A prefab home exhibit opened John’s eyes to a better way of building and inspired his mission."[07:25] - From Engineer to Diplomat to Builder"John shares how his global work helped him spot the housing crisis as a real problem to fix."[10:09] - Why Housing Innovation Fell Behind"Homes take longer and cost more today than in the 1960s, John explains why change is overdue."[13:07] - Rethinking Risk to Start a Company"Leaving a stable job was tough, but learning to see risk in a new way helped John take the leap."[14:53] - Turning Homes Into a Factory Process"John explains how car-style production lines and steel frames help build better, faster homes."[19:42] - Blending Standard Design with Custom Feel"Standard frames and flexible layouts allow homes to feel unique while staying easy to build."[22:24] - Labor and Logistics in Home Building"Even in a factory, homes take skilled work, and every site brings its own tricky challenges."[27:02] - Strategy, Scaling, and a Life-Changing Book"John explains how scaling isn’t about more small homes but bigger impact and how a book by Annie Duke helped shape his thinking."[33:18] - Global Momentum and What’s Next"John shares why support from countries like Canada and Australia shows prefab housing is gaining ground and how rising costs may push the U.S. to follow soon."FOLLOW THE GUEST:LinkedIn Accounts: John Avrett: https://www.linkedin.com/in/john-avrett-26891944/ Hive Modular: https://www.linkedin.com/company/hivemodular/ US Department of State: https://www.linkedin.com/company/doscareers/US Navy: https://www.linkedin.com/company/us-navy/ United States Air Force: https://www.linkedin.com/company/united-states-air-force/ Websites: Hive Modular: https://www.hive-modular.com/ US Department of State: https://www.state.gov/ US Navy: https://www.navy.mil/ United States Air Force: https://www.airforce.com/ FOLLOW THE HOST:LinkedIn: https://www.linkedin.com/in/barryoreilly Personal site: https://barryoreilly.com Facebook: https://www.facebook.com/barryoreillyauthor/ Twitter: https://x.com/barryoreilly Instagram: https://www.instagram.com/barryoreilly/ Email: hello@barryoreilly.com

May 7, 2025 • 35min
The New Science of Self-Actualization for Founders to Reinvent Identity & Find Meaning - Faisal Hoque
Faisal Hoque, a prolific author and entrepreneur, shares his insights on blending Eastern wisdom with modern leadership. He discusses how unlearning past beliefs can foster personal and professional growth. The importance of collaboration over competition in entrepreneurship is highlighted, showcasing a venture studio's unique approach to launching companies. Faisal emphasizes the need to rethink efficiency by focusing on human effectiveness and suggests tools like meditation and AI for continuous self-improvement.

22 snips
Apr 23, 2025 • 46min
Unlearning Legacy Systems to Build Antifragile AI Operating Models with Ja-Naé Duane
Ja-Naé Duane, a systems thinker and behavioral scientist, dives into unlearning outdated practices to build resilient AI models. She discusses how the pandemic prompted a shift from centralized systems to decentralized resilience. Ja-Naé emphasizes reconnecting with primal skills in a technologically advanced world. The conversation also highlights the importance of self-awareness and adopting transformative mindsets for personal growth. Finally, she explores the role of Generative AI in boosting productivity and innovation in the business landscape.

Apr 9, 2025 • 44min
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 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 Officer at Hemnet, Sweden’s leading property platform, where she played a pivotal role in scaling the product organization and driving the company through a successful IPO in 2021. Under her leadership, Hemnet achieved consistent double-digit growth, became one of Sweden’s most appreciated apps, and stood out as a top performer on the Swedish stock exchange.But her story goes far beyond business metrics. Francesca led cultural shifts too, transitioning the company language to English and increasing female representation in tech, proving that growth and inclusion can go hand in hand.In this episode, we explore how Francesca thinks about unlearning as a tool for personal and organizational growth, building product excellence at scale, and creating environments where diverse teams thrive.Key Takeaways:Changing careers: Francesca switched from fashion in Milan to tech in Sweden after many rejections, showing strong resilience.Product Management: Asking many questions helped her shift from project management to product management.Asking for Help: Great leaders don't need to know everything; asking for help builds stronger teams.Idea company size: Francesca thrives best in scale-up companies (40–400 people), not large corporations.Unlearning and Growth: Every new role required Francesca to "unlearn" old ways to adapt to new challenges.Additional Insights:Changing Roles: Your job changes when your company grows, so be ready for change.Know your strength: Understand clearly what you’re good at and where you fit best.Start Fresh: Always approach new tasks like you're learning for the first time.Get ready for a powerful conversation with Francesca Cortesi on embracing change, scaling with intention, and building inclusive, high-performing product teams that thrive through continuous unlearning and growth.Episode Highlights: [01:00] - Episode Recap "Welcome to the Unlearn Podcast, Exploring career shifts, new leadership styles, and how to build strong product teams."[02:03] - Guest Introduction: Francesca Cortesi "Francesca, former Chief Product Officer at Hemnet, helped scale the product and led the company to a successful 2021 IPO."[03:22] - From Milan Fashion to Stockholm: The First Career Pivot "I worked in fashion, got a translator job in Sweden, and decided to move."[07:10] - Facing Rejection and Redefining Identity "I tried returning to fashion, but it wasn’t working, time to move on."[10:13] - Discovering Product Management Through Curiosity and Questioning "I kept asking questions, turns out, that curiosity led me into product management."[15:20] - What Francesca Had to Unlearn"As a product manager, I had to leave behind what worked before, it’s always contextual."[19:56] - Transition from Individual Contributor to Product Leader "My first leadership role taught me to stop copying others and find my own style."[24:54] - Why Role Expectations Must Be Rewritten During Scaling "Too many questions about roles and success? That’s your sign to pause and redefine expectations."[27:52] - Realizing Where She Thrives: The Scaleup Stage "My sweet spot? Companies ready to scale after finding product-market fit."[37:24] - From Operator to Advisor: Unlearning and Redefining Impact"New roles come with new expectations, especially the ones you set for yourself."Follow Our Guest:LinkedIn Accounts: Francesca Cortesi: https://www.linkedin.com/in/francesca-cortesi/Prodotto Collective: https://www.linkedin.com/company/prodotto-collective/ Hemnet: https://www.linkedin.com/company/hemnet/ Websites: Prodotto Collective (Francesca’s Personal Site): https://www.francescacortesi.com/ FOLLOW THE HOST:LinkedIn: https://www.linkedin.com/in/barryoreilly Personal site: https://barryoreilly.com Facebook: https://www.facebook.com/barryoreillyauthor/ Twitter: https://x.com/barryoreilly Instagram: https://www.instagram.com/barryoreilly/ Email: hello@barryoreilly.com