Unlearn

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 his perspective on loyalty, legacy, and leadership—and why “patient capital” is poised to disrupt the short-termism of private equity. We explore how purpose-driven investing is solving real-world challenges, from cancer to climate, and what it takes to build sustainable family office infrastructure in an era of unprecedented generational wealth transfer.And the timing couldn’t be more relevant: family offices are no longer niche players. The number of single-family offices has surged 31% since 2019, with projections reaching over 10,700 globally by 2030. As trillions of dollars transition to the next generation, Ron offers a front-row seat to the values, strategies, and systems needed to steward that wealth wisely.Ron is also the Founder, Host, and CEO of Family Office World Media, and helped establish the Family Office Program for TIGER 21, where he chairs a national peer group. He lectures at Oxford, Stanford, Harvard, and the University of Chicago Booth School of Business, and was recently appointed Editor-in-Chief of The National Law Review’s first Family Office newsletter. A LinkedIn Top Voice, TEDx speaker, and former hedge fund founder, Ron began his career on Wall Street at Bear Stearns and Drexel Burnham.Key TakeawaysPeople Over Companies: Ron’s experience during Drexel’s collapse taught him that relationships—not institutions—are what endure.Patient Capital Is a Game-Changer: Family offices can think in decades, not quarters, offering strategic advantage over traditional funds.Purpose Before Profit: Legacy and social impact must anchor investment decisions.Professionalization Is Essential: Governance, infrastructure, and talent are what turn capital into capability.The Ego Barrier: Great wealth doesn’t guarantee great management—humility is crucial for longevity.Five Core Principles from Ron Diamond1. Guiding North Star: Profit with PurposeAnchor investments in something bigger than financial return—personal mission, legacy, or societal impact. → Tip: Define your North Star early and align capital accordingly.2. Trust & Relationships FirstBack character over credentials. Trust and personal integrity build more resilient partnerships than models or metrics. → Tip: Focus on people, not pitch decks.3. Patient, Long-Term CapitalThink in decades, not exit cycles. Family offices can outperform by holding steady and avoiding short-termism. → Tip: Let compounding do the heavy lifting.4. Professionalizing Family OfficesFamily offices must evolve beyond legacy systems—invest in governance, talent, and infrastructure like any top-tier fund. → Tip: Treat talent as a profit center, not a cost.5. Entrepreneurial PhilanthropyDeploy strategic, venture-style capital into social challenges. Purpose and profit can—and should—coexist. → Tip: Apply the same rigor to social impact as you do to your investments.Episode Highlights00:00 – Episode RecapRon Diamond shares how witnessing the downfall of Drexel Burnham sparked his lifelong belief in prioritizing people over companies—and why loyalty should lie with individuals, not brands.01:39 – Guest Introduction: Ron DiamondBarry introduces Ron Diamond, Chairman of Diamond Wealth and Family Office World Media, and a leading voice in purpose-driven capital and governance reform.05:13 – Building a Family Office SyndicateRon explains his “first call alpha” model—aggregating capital from 100+ family offices to invest together in private markets.08:40 – The North Star PhilosophyFrom Milken’s prostate cancer initiative to Eric Lefkofsky’s Tempus Labs, Ron shows how personal purpose drives breakthrough impact.11:41 – Listening to Find Values AlignmentRon’s secret to identifying values-driven leaders: listen more, talk less—and show up without an agenda.16:43 – Growth Mindset Over ScarcityCompeting with others is outdated—Ron champions an abundance mindset rooted in collaboration and long-term thinking.20:32 – The Operational Trap for New Family OfficesRon breaks down why most new family offices fail and how professionalization—from mission statements to succession—can change that.23:41 – The Power and Pitfalls of Patient CapitalHe explores how family offices can outperform PE firms by holding long-term and avoiding short-term incentives.32:42 – Creating a Playbook for Next-Gen WealthFrom Booth to Stanford, Ron is building the first structured family office curricula focused on governance, values, and impact.39:31 – Investing in Talent Like an InstitutionRon outlines why top talent needs equity, not just salary—and why underinvesting in people is the silent killer of family offices.44:34 – Finance Meets PhilanthropyWhy family offices—not government or corporations—will solve many of society’s biggest challenges in the next 20 years.45:31 – Closing ReflectionsRon shares how listeners can follow his work and why patient capital is the future of both wealth and impact.🔗 Useful ResourcesRon Diamond LinkedInRon Diamond Website Diamond WealthFamily Office World Media

David Homan, founder and CEO of Orchestrated Connecting and a classical composer, joins to discuss transforming networking into genuine connection. He emphasizes that vulnerable conversations in small groups can break down barriers, leading to authentic relationships. Homan shares insights on the importance of giving without expecting anything in return and how music can serve as a metaphor for connection. He also highlights the need for community leaders to inspire collaboration amidst today's polarization, advocating for purposeful, empathetic engagement.

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/

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

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.

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.

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.

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.

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

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.