Unlearn

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 selling his company AgileCraft for $166M—earning recognition as a Fortune Best Small Business in America and a finalist for the Ernst & Young Entrepreneur of the Year. With five successful exits under his belt, Steve brings rare depth to the art of building and unbuilding what no longer serves.In this conversation, Barry and Steve explore how to design for the messy reality of modern work, the role of unlearning in leadership, and how AI is redefining what it means to be a decisive company.Key TakeawaysFrom CTO to CEO – Why Steve transitioned from tech leader to founder and the personal growth that came with it.Scaling after acquisition – The emotional and strategic shifts required when your startup becomes part of a larger machine.Why strategy execution breaks – Most alignment tools assume order—Steve builds for complexity.Agentic AI in the enterprise – How Dotwork uses knowledge graphs and AI to surface insight in context, not just dashboards.Decisive companies – What it really means to help leaders make faster, more confident decisions.Additional InsightsUnlearning the idea that startups are for the young—Steve didn’t found his first company until his 40s.How Dotwork is building a “context memory engine” for both executives and AI agents.The future of AI-native tools isn’t more interfaces—it’s less friction and smarter context delivery.Why the most valuable enterprise products aren’t flashy—they’re quiet, ambient, and deeply integrated.Episode Highlights00:00 – Episode RecapSteve Elliott shares how each startup exit taught him something new—but also how returning to the founder’s seat means unlearning old assumptions. Now, with Dotwork, he’s not just building a tool—he’s rethinking how organizations make decisions in complexity.01:45 – Guest Introduction: Steve ElliottBarry introduces Steve Elliott, founder of AgileCraft (acquired by Atlassian) and CEO of Dotwork, with a track record of five successful exits and a deep focus on enterprise work management.03:40 – Early career shiftsFrom a consulting career at PwC to software experiments that took off—how Steve found his way into entrepreneurship.08:55 – From technologist to founderThe value of combining tech expertise with business empathy—and why startups offer unmatched learning opportunities.11:05 – Unlearning post-acquisition mindsets What Steve had to unlearn transitioning from CEO to leader within a larger company—and back again.13:36 – Building tools for strategic decisionsWhy enterprise tools fail to support real-time, strategic decisions—and how Steve is tackling the problem differently.17:50 – The rise of agentic frameworksHow Dotwork is using knowledge graphs and agentic AI to reflect the dynamic, decentralized nature of modern organizations.23:31 – Breaking through transformation fatigueHow Dotwork builds trust not through marketing, but by showing real, contextual results fast.26:23 – Beyond dashboards: AI-native UXWhy true AI-native platforms don’t ask you to log in—they come to you with insight in the moment.32:44 – Coaching execs on AIBarry shares his experience coaching executives on AI—and why hands-on experimentation is the only path to mastery.36:07 – Context engines for agentsSteve explains how Dotwork unintentionally became a context memory platform—crucial for the future of autonomous agents.40:36 – Magic moments in enterprise UXWhen engineering hasn’t seen the reports their software generates—because the platform is that intuitive.43:17 – Closing ReflectionsSteve reflects on the value of doing over theorizing—and the importance of staying close to the problem if you want to innovate meaningfully.

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 to say yes to opportunities beyond her comfort zone, the strategic shifts she's leading inside a fast-scaling company, and why the future of HR is about enhancing humanity, not replacing it. If you’re wondering what leadership looks like when AI meets empathy, this one’s for you.Key TakeawaysUnlearning expertise-dependence: Cass shifted from relying on experts to co-creating solutions with AI tools before engaging others.AI as a force for elevation: At Progyny, AI is used to give employees time back, not take roles away—enabling deeper focus on human-centric work.Low-code leadership: Cass, a self-described non-technical leader, built HR bots and reimagined policies through practical AI applications.Scaling culture through consistency: AI chatbots improved response times, standardized answers, and gave insight into employee concerns.Embedding experimentation: Teams are encouraged to ask, "What should I stop doing?"—sparking a culture of reinvention and initiative.Additional InsightsProgyny’s “Super Fans” initiative reframes AI gains as an opportunity to deepen customer and employee relationships.Training is done in cohorts to build shared understanding and reduce AI anxiety.Cross-functional collaboration with junior team members—like the intern who built the HR bot—shows how innovation can come from any level.Cass uses AI to simplify and globalize complex frameworks like competency models, improving alignment across teams and geographies.Episode Highlights00:00 – Episode Recap Cassandra Pratt shares how embracing discomfort led her to leap into healthcare, build a transformative HR function, and lead with AI—not to eliminate roles, but to elevate people and amplify their impact.02:37 – Guest Introduction: Cassandra Pratt Barry introduces Cass Pratt, Chief People Officer at Progyny, a fertility and family-building benefits company scaling rapidly with a human-first, tech-empowered culture.04:48 – Saying Yes to Growth Cass reflects on a missed opportunity that taught her the cost of saying no—and set her on a path to jump into unknowns with conviction.08:04 – Startup Lessons and Leadership Growth From 50 to 850 employees, Cass shares what it means to grow with a company and embrace mistakes as part of the journey.11:00 – Diving into AI Without a Tech Background Despite lacking technical skills, Cass threw herself into generative AI—learning by doing and discovering intuitive ways to drive value.13:10 – Unlearning the Expert Reflex Cass rethinks her default of turning to experts first—instead starting with AI to shape stronger ideas and bring others in as collaborators.15:13 – Redesigning Processes, Not Just Tools AI opened up opportunities to rethink workflows from scratch, not just automate existing inefficiencies.20:35 – Making AI Safe and Human Cass shares how transparent messaging, training, and cultural reinforcement helps ease AI anxieties and keep the focus on people.25:00 – Building the HR Bot with an Intern An intern-built benefits chatbot improved response times, consistency, and surfaced new insights—highlighting the power of junior talent and experimentation.28:41 – Simplifying Competency Models with AI Cass uses AI to refine complex frameworks, making them scalable across geographies and easier for leaders to apply.30:00 – Rethinking Work Through Elimination By asking what should be stopped—not added—Cass surfaces high-leverage opportunities to transform HR workflows.34:33 – The Two Extremes of HR and AI Adoption Cass observes a divide: HR teams either lead AI transformation—or risk being the last to catch up.40:45 – Cross-Functional Collaboration and Culture AI transformation is a team sport—embedding HR into company-wide initiatives empowers better collaboration and outcomes.43:38 – Freeing Up Time to Be Present Cass highlights how AI helps reclaim time for the most human part of HR: being present, listening, and solving meaningful problems together.Useful ResourcesProgyny: https://www.progyny.comConnect with Cassandra Pratt: LinkedInAI Executive Coaching by Barry: https://barryoreilly.comFollow the HostLinkedIn: linkedin.com/in/barryoreillyWebsite: barryoreilly.comFacebook: facebook.com/barryoreillyauthorTwitter/X: x.com/barryoreillyInstagram: instagram.com/barryoreilly

Phil Gilbert, former General Manager of Design at IBM and author of Irresistible Change, shares his groundbreaking insights on business transformation. He emphasizes that real change starts with culture, not just tools. Discussing his three-part model of people, practices, and places, he outlines how to ignite transformation within organizations. Phil also explores the crucial role of teams in adopting AI and the importance of designing leadership structures that foster trust. His experiences and practical frameworks provide a compelling blueprint for leaders aiming to create lasting impact.

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, real-world stories, and a refreshing candor to a space that’s often muddled with jargon. This is a must-listen for any founder, PMM, or GTM leader tired of being misunderstood—and ready to focus.FletchPMM is a product marketing consultancy that helps B2B tech startups nail their positioning and bring it to life through a purpose-built homepage. Alongside co-founder Rob Kaminski, he’s helped more than 400 companies craft focused, champion-centered messaging that converts.Key TakeawaysClarity wins: Positioning isn’t about vision—it’s about specificity, segmentation, and telling your champion’s story.Unlearn the fluff: Ditch the vague benefits and generic promises. Customers need to know what you do and how it helps them.Focus = traction: Trying to be everything to everyone dilutes your impact. Specialization creates memorability and repeatability.Your homepage is your positioning: It’s the one asset every stakeholder sees—customers, investors, your team. Make it count.Position for the champion, not the budget holder: Focus your messaging on the person closest to the problem—not the executive who cuts the check.Additional InsightsPositioning is pattern recognition: Anthony shares how lessons from church leadership and freelancing helped him recognize early signs of positioning misalignment—even before he had the language for it.Inbound scale comes from consistency, not creativity: With over 500 companies served, Fletch’s success has come from delivering one service, the same way, every time—not by chasing new ideas or tactics.Founders often confuse luck with repeatability: Anthony reveals how many early startup wins come from personal networks—and how this masks the real need for scalable positioning and segment focus.Mispositioning starts with the homepage: Anthony critiques vague, benefits-only messaging like “Make Yes Work”—demonstrating how the lack of a clear product reference point derails understanding and action.Repositioning is an organizational act: Referencing Klaviyo and Meta, Anthony shows how homepage messaging isn’t just about marketing—it forces internal alignment by making strategic bets visible to every team member.Episode Highlights00:00 – Episode RecapAnthony Pierri shares how a seemingly minor contradiction in a church’s mission statement became his first exposure to a positioning problem—planting the seed for a career built around clarity.01:30 – Guest Introduction: Anthony PierriBarry introduces Anthony, co-founder of FletchPMM, a consultancy that’s helped 400+ B2B software startups craft focused, conversion-driving homepages.05:09 – The Real Cost of Doing EverythingWhy trying to serve every persona or use case is the quickest way to stall traction—and how narrowing your focus builds momentum.07:14 – Specialization is a Strategic AdvantageAnthony explains how one service, delivered one way, to one segment unlocked a scalable, inbound engine for Fletch.11:42 – Sales Strategy or Sales Chaos?The folly of hiring SDRs before narrowing your GTM focus—and why customer acquisition doesn’t scale without segment clarity.14:03 – Champion-Centric PositioningDon’t aim for the budget holder—speak to the person closest to the problem. They’ll become your internal advocate.22:07 – How AI Will Impact Product PositioningAs software creation and discovery become more agent-driven, Anthony sees the same need for ultra-specific, capability-first messaging.29:19 – Talking About Yourself Without Talking About YourselfPositioning isn’t self-promotion—it’s about telling a compelling story that reflects your champion’s reality.35:15 – The “Tell Me More” EffectGreat positioning doesn’t try to say everything. It just gets the right person to say, “Tell me more.”38:17 – Your Homepage is Your Most Important AssetThe homepage isn’t just a lead gen tool—it’s the most visible alignment document your org has. Make it reflect your real strategy.44:53 – Changing the Narrative at ScaleAnthony shares why embedding your positioning on the homepage is more powerful (and more visible) than internal decks ever will be.46:35 – How to Structure a Homepage That ConvertsBarry and Anthony unpack how to use messaging anchors, problem framing, and customer-centric storytelling to guide your homepage narrative.Useful ResourcesFletchPMM WebsiteAnthony Pierri on LinkedInApril Dunford – Obviously AwesomeWynter – Message TestingFollow the HostLinkedInOutlier Venture PartnersFacebookTwitter/XInstagram

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 calls doesn’t satisfy your social diet.As someone who experienced this firsthand—working remotely, starting over in a new country—I share my own journey to unlearning the myth of self-sufficiency and redesigning my life to engineer real connection. This conversation is a call to rethink how we connect, show up for each other, and take our social health as seriously as sleep, diet, or exercise.Key TakeawaysLoneliness Is a Biological Threat: Your brain interprets social disconnection like hunger or pain—not just a mood, but a warning signal.Small In-Person Moments Matter: Even brief, face-to-face interactions boost mood and cognitive function more than digital ones.Isolation Damages the Brain: Chronic loneliness raises cortisol, shrinks memory centers, and can shorten your lifespan.Introverts Still Need People: Social time benefits everyone—introverts just hit their saturation point sooner.Generosity Is Hardwired: From rats to dolphins, the impulse to connect and give is deeply embedded in our biology.Connection Requires Unlearning: Independence and solitude aren't always virtues—sometimes they’re survival myths in disguise.Additional InsightsSocial prediction systems in the brain were scrambled by COVID—and many people still haven’t recalibrated.Most people think they’re worse-than-average at socializing, which fuels avoidance and false self-judgment.Digital tools remove the social cues—tone, expression, touch—that our brains need to feel emotionally nourished.Empathy is not automatic—it’s biased and trainable, shaped by exposure to difference and intention.Rebuilding community isn’t just good for you—it’s essential for physical, mental, and societal health.Episode Highlights00:00 – Episode RecapBen Rein discusses the importance of socializing, likening it to sleep, diet, and exercise, and emphasizing its role in overall well-being.02:07 – Guest Introduction: Ben ReinBarry introduces Dr. Ben Rein, neuroscientist and author, and outlines the episode’s focus on the biological necessity of human connection.03:43 – How COVID Broke Our Social PredictionsBen shares his neuroscience background and explores how societal shifts and the pandemic disrupted the brain’s expectations for everyday interaction.08:23 – Barry’s Story: “You Sound Lonely”Barry recounts a personal moment of realization and how a friend’s observation pushed him to rebuild his social life with intention.11:29 – Why We Miss the Signs of LonelinessBen explains why loneliness often goes undetected, how it manifests as stress, and why virtual connection isn’t enough.16:44 – The Hard Work of Making FriendsBarry reflects on the discomfort of building new friendships as an adult—and why it’s worth the effort for mental and emotional health.21:10 – The Neuroscience of Social FearBen breaks down why we underestimate the value of interaction, how fear holds us back, and the courage it takes to engage.25:33 – Designing for ConnectionBarry shares how he now intentionally schedules social time as part of his weekly routine—and encourages others to do the same.29:46 – Writing Lessons: Structure MattersBen opens up about his writing process and the hard-earned lesson of keeping a book focused on its core idea.32:58 – Empathy is in Our NatureBen shares surprising studies showing kindness and empathy across the animal kingdom—and what humans can learn from them.39:22 – Closing ReflectionsBarry and Ben wrap with a call to action: prioritize connection, embrace kindness, and use what we know to better ourselves and others.Useful ResourcesWhy Brains Need Friends by Dr. Ben ReinDr. Ben Rein on LinkedInBen’s popular science content on Instagram and TikTokFollow the HostLinkedInPersonal SiteFacebookTwitterInstagram

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 into the most overlooked challenges founders face when they scale: losing visibility, clinging to control, and skipping the crucial step of designing people and culture systems that can actually support growth. From shadow planning and succession strategies to why success itself can be terrifying, Theresa shares powerful tools and real talk every startup leader needs to hear.If you're moving past 20 employees and want to build a company that lasts—without losing what made it special—this conversation is your playbook.Key TakeawaysStart HR Strategy Early: Don’t wait for burnout or lawsuits—build people ops into your scaling strategy from day one.Shadow Planning Is Essential: Prepare for the worst by confronting your team’s shadow behaviors and stress reactions before they sabotage growth.Succession Planning Isn’t Personal: It's about scalability. Delegate early, document processes, and regularly revisit org design.Growth Changes Everything: Founders need to let go to level up. What got you here won’t get you there.AI in HR Is a Tool, Not a Fix: Automate the repetitive, but double down on building trust and strategic visibility.Additional InsightsHR should be the connective tissue of an organization—not the "issues and tissues" team.Scaling gracefully requires confronting the emotional toll of growth, including fear of success.Theresa shares how early experiences at Microsoft and ThoughtWorks shaped her belief in high-trust, high-agency cultures.Executive coaching and intentional design can prevent burnout and boost retention.Episode Highlights00:00 – Episode Recap Theresa Cantwell unpacks the emotional complexity of growth—from the fear of success to the need for intentional HR design. With experience scaling organizations across continents, she shares how founders can build people-first cultures that thrive under pressure.01:54 – Guest Introduction: Theresa Cantwell Theresa is a strategic HR consultant and founder of GSD HR Consulting, with nearly two decades of experience building and scaling agile-aligned cultures in the tech and digital sectors.04:43 – Pivotal Moment at Microsoft Seeing a team she’d hired bonding over lunch sparked her transition from recruitment to building cultures that last.06:28 – ThoughtWorks and Radical Culture Design Barry reflects on his own onboarding experience and how Theresa helped him understand the unique culture of ThoughtWorks from day one.09:33 – From Recruiter to Culture Architect Theresa shares why she shifted from acquisition to engagement, building full lifecycle HR strategies rooted in trust and clarity.15:29 – When to Start Thinking About People Strategy At 20 people, you need to get intentional—mission, values, cofounder conflict prep, and hiring bar must be aligned.18:51 – Shadow Planning Explained Why leaders must confront their own stress behaviors and prepare for the worst—before it happens.22:39 – Handling Employee Departures with Grace How to de-risk talent exits through succession planning and constant market awareness.26:39 – Scaling Yourself Out of a Job Helping leaders delegate, prevent burnout, and imagine new roles for themselves as the company grows.32:16 – When to Start Succession Planning The earlier, the better—start once you have traction. Document, delegate, and depersonalize the process.36:17 – AI’s Role in HR AI can’t replace the human heart of HR—but it can free you to focus on what matters most.38:50 – Closing Reflections Barry praises Theresa’s impact and encourages founders at scaling junctures to seek her wisdom and services.Useful ResourcesTheresa Cantwell on LinkedInGSD HR ConsultingFollow the HostLinkedInWebsiteFacebookTwitter / XInstagram

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