Unlearn

Barry O'Reilly
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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
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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.
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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.
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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.
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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.
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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
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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.
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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.
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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
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Mar 26, 2025 • 39min

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 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 The Contentment Foundation has helped leaders and teams boost performance and teamwork. She is also the Board Advisory Member of Equalture. Tune in for an insightful talk on unlocking human abilities and building creative workplace cultures!She is a respected neuroscientist who is dedicated to guiding young professionals and bringing fresh ideas into different industries. Dr. Marcia’s work is a valuable resource for anyone aiming to make a big impact in technology and business.Dr. Marcia Goddard, a neuroscience expert with over 10+ years of experience, applies brain science to boost workplace performance and culture. She has consulted with high-performance teams, including Formula 1 and Fortune 500 companies, optimizing team dynamics. Her thought leadership focuses on psychological safety and inclusion, guiding organizations toward innovation and growth.Key Takeaways:Expanding Globally: Dr. Marcia Goddard’s strategies for international growth.  Overcoming Challenges: Solutions for fast-changing industries.  Adapting to Change: Stay flexible, ditch outdated methods.  Personal Experience: Dr. Goddard’s lessons in action.Additional Insights:Effective Strategies: Dr. Marcia Goddard on reshaping industries.  Thriving in Growth: Tips for fast-expanding businesses.  Experience to Innovation: Dr. Goddard’s journey to better solutions.Get ready for an enlightening conversation with Dr. Marcia Goddard on infusing new ideas into business strategies and fostering a culture of innovation and growth.Episode Highlights: [00:36] - Episode Precap"Welcome back to the Unlearn podcast, where we challenge conventional thinking to unlock high performance and breakthrough innovation."[01:17] - Guest Introduction: Dr. Marcia Goddard“I'm joined by Dr. Marcia Goddard, a neuroscientist, author, and keynote speaker specializing in applying brain science to workplace performance and culture.”[02:30] - Navigating Introversion, Networking Opportunities, and Career Growth"My career was once a series of what I called coincidences, but I no longer believe they were."[06:46] - Unlearning Misconceptions in Neuroscience"There are two answers to that. My favorite quote is, 'If the brain were simple enough for us to understand, we would be too simple to understand it.”[10:26] - Practical Tips for High-Performance"It's a good question, especially in individual coaching. I think that's what it's related to."[12:40] - The Importance of Reflection in Decision-Making"We often tell ourselves we must decide now, but that’s rarely the case."[15:58] - Enhancing Team Communication"The most common thing I see at a team level, especially in growing organizations."[18:44] - Remote Work and Maintaining Connections"For remote organizations, let’s be clear: I don’t support full-time office work."[26:04] - Future of High-Performance Teams"Looking ahead, what excites you most in the industry, and what do you think needs to be unlearned?"[29:31] - Rethinking Diversity and Inclusion Programs"We need to unlearn the notion that ticking boxes creates impact and that DEI is just the right thing to do."[35:52] - Future Trends in Neuroscience and Performance Teams"Looking ahead, what excites you most about the future of performance teams and neuroscience?"Follow Our GuestLinkedIn Accounts: Dr. Marcia Goddard: https://www.linkedin.com/in/mngoddard/Brain Matters: https://www.linkedin.com/company/brainmattersconsulting/ Formula 1: https://www.linkedin.com/company/formula-one-management-ltd/ Equalture: https://www.linkedin.com/company/equalture/ The Contentment Foundation: https://www.linkedin.com/company/the-contentment-foundation/ Leiden University - Faculty of Archaeology: https://www.linkedin.com/company/faculty-of-archaeology-university-of-leiden/ Websites:   Brain Matters: https://brainmattersconsulting.com/ Formula 1: https://www.formula1.com/ Equalture: https://www.equalture.com/ The Contentment Foundation: https://www.contentment.org/ Leiden University - Faculty of Archaeology: https://www.universiteitleiden.nl/en/archaeology ____________________________________________________________Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.Download Now: https://bit.ly/InnovationPortfolioWorkbook 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

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