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What if networking wasn’t about schmoozing but about being seen? David Homan joins me to unlearn the myths of traditional networking and share how vulnerability, deep listening, and small group connection can foster truly meaningful relationships. As a master connector, classical composer, and co-author of Orchestrating Connection, David breaks down the silent skills that build trust, activate communities, and transform the way we gather.
David Homan is the founder and CEO of Orchestrated Connecting, a global community of connectors; Orchestrated Opportunities, an impact-focused advisory firm; and SOAR CONNECT, a start-up focused on the strength of authentic relationships. He hosts the Orchestrated Relationships podcast on developing relationship value, is an active classical composer, and a proud father of two. From middle-class beginnings as the son of a college professor and nonprofit-focused mother, he has built a network that reaches into the most private and powerful circles globally, all while honoring a code of purposeful community building.
Key Takeaways00:00 – Episode Recap
David Homan reveals how he had to unlearn everything he thought he knew about networking—discovering instead that vulnerability, deep listening, and structured intimacy were the keys to building purposeful community.
01:50 – Guest Introduction: David Homan
Barry introduces David Homan, master connector, startup founder, and co-author of Orchestrating Connection, whose work helps leaders create impact-driven relationships through authentic connection.
02:52 – Why Most Events Miss the Mark
David shares why traditional networking events feel awkward—and how his approach to curated small groups flips the script to create meaningful experiences.
04:49 – Start Small, Go Deep
Barry reflects on the power of small group interactions and how vulnerability accelerates meaningful connections.
08:01 – Sharing Real, Not Polished
David explains the importance of self-worth and courage when choosing to open up authentically in conversation.
10:45 – Creating Connection Through Authenticity
Being real invites empathy—and sets the tone for deeper, more rewarding conversations.
13:18 – Your Reputation When You're Not in the Room
David describes how authentic acts ripple through your network, strengthening your reputation and reach over time.
17:39 – Unlearning Transactional Thinking
Helping someone doesn’t obligate them—it expands your access to their trusted circles.
20:36 – Conducting Communities Like a Composer
David draws on his classical music training to explain how relationships can resonate like instruments in a symphony.
25:16 – Event Design That Actually Works
Purpose-driven event planning means matching people’s needs and asks—not just gathering for the sake of it.
28:13 – Why Givers Struggle to Ask
David outlines the “Impact Ask” framework to help mission-driven people communicate their needs confidently.
31:59 – Fundraising as Shared Mission
Barry reflects on how reframing fundraising as an invitation to join a mission transformed his startup experience.
33:59 – The Future of Community
David offers a hopeful vision: intentional communities built on shared values, layered for systemic change.
35:56 – How to Connect with David
David shares how listeners can join his private, connector-driven community—and what qualities matter most.
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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 Takeaways00:18 – Episode Recap
Paul 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 Hutchinson
Barry 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 Leadership
Paul 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 Children
Paul 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 Healing
The 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 Connection
Paul 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-Transformation
Paul offers guidance for listeners on beginning their own journey of healing trauma through meditation, breathwork, and embracing vulnerability.
47:26 – Closing Reflections
Paul emphasizes the power of storytelling and awareness to inspire change, thanking Barry for amplifying the voices fighting modern slavery.
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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 Takeaways00:00 – Episode Recap
Brad Feld reframes mentorship as a shift from a one-way hierarchy to a peer-based relationship.
01:48 – Barry Introduces Brad Feld
Barry introduces Brad's influential work on startup communities and his philosophy of "Give First."
03:12 – Startup Community Origins
Brad 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 Philosophy
Brad explains why generosity, long-term thinking, and non-transactional relationships are foundational to resilient startup ecosystems.
21:33 – Mentorship as Mutual Growth
A powerful story with mentor Len Fast reveals how Brad came to see mentorship as co-learning rather than knowledge transfer.
27:27 – Knowing Yourself
Brad 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 Matters
A candid discussion on disconnecting from external pressures, valuing inner reflection, and how time off helped Brad refocus on his values.
41:47 – Redesigning Relationships
Brad 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 Reflections
Brad 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 Feld
Foundry Group on LinkedIn: Foundry Group
Foundry Group website: foundrygroup.com
Techstars website: techstars.com
What if becoming a better leader meant letting go of being the expert? In this Unlearn episode, I’m joined by David Tuck, Chief Executive of Waracle, for a thoughtful and human-centered conversation on the mindset shifts required to lead high-performing teams in complex, fast-changing environments.
David’s leadership journey spans over 15 years of agile transformation, commercial growth, and organizational design. He’s held executive roles at Kin + Carta, The App Business, ThoughtWorks, and Scott Logic, and now leads Waracle, a strategic design and technology consultancy that builds trusted digital products for enterprise clients.
Known for his calm conviction and people-first approach, David shares how curiosity, craft, and long-term client intimacy have shaped his leadership philosophy. From stepping back in his career to hone his sales skills, to becoming a CEO who leads experts by asking better questions, David reflects on what it means to grow companies—and yourself—by design.
This episode explores how to lead through inquiry, build trust at scale, and why today’s leaders must become “Chief Unlearn Officers” to stay relevant in an AI-powered world.
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What if the biggest risk in your business isn’t building the product but realizing no one wants it? In this Unlearn episode, I’m joined by Alistair Croll, technologist, entrepreneur, and bestselling author of Lean Analytics, for a candid and clever conversation on rethinking product development, marketing, and demand generation.
Alistair’s work focuses on data-driven innovation and human behavior. He co-authored Just Evil Enough: The Subversive Marketing Handbook, a playbook for bending the rules to win in the attention economy. He has chaired global tech conferences like O’Reilly’s Strata and currently leads Startupfest, where he helps founders turn clever ideas into competitive advantage.
Known for blending insight with humor, Alistair unpacks why subversive creativity, not perfection, often wins. From the “fluency equation” to Burger King’s clever customer acquisition tactics, he reveals how unconventional strategies generate meaningful traction. This episode explores the science of subversive marketing, reframes how we think about product launch risk, and dives into the mindset shifts leaders need to stay relevant in the AI era.
Key Takeaways00:00 – Episode Recap
Alistair reframes startup risk with a clever hand-raising test: building isn’t the danger, indifference is.
03:16 – The Beach-Read Business Book
Why Just Evil Enough was built to entertain and educate, and how surprise fuels learning.
07:30 – The Real Startup Risk
Most teams focus on building because it feels safe. But the real risk is customer indifference.
08:41 – Subversive Marketing in Action
The Whopper Detour: How Burger King used playful tactics to achieve strategic goals.
13:20 – The Fluency Equation Explained
A new way to understand user hesitation and remove behavioral friction.
19:14 – AI, Fluency, and Leadership Gaps
Why executives aren’t using AI, even when they know they should.
26:00 – Decision-Making Matrix for Innovation
A two-by-two framework to help teams run smarter experiments with lower risk.
31:01 – The Fourth Miscapitalization
Why companies are still over-investing in engineering in an AI-native era.
35:55 – How to Start with Demand First
Real-world examples of flipping the build-first model by validating before committing.
39:14 – The Subversive Mindset
Disagreeability, creative risk, and how to spot the systems you're trapped inside.
41:36 – Ethical Persuasion
How to avoid crossing the line from clever to manipulative.
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Today on the Unlearn podcast, we welcome Jamie Dobson, technologist, entrepreneur, and a leader known for building systems that connect innovation with purpose. He joins us to share a deeply reflective journey: spanning childhood curiosity, extreme programming, leadership challenges, and the hard truths of building a company with intention.
Jamie Dobson is the co-founder and former CEO of Container Solutions, a consultancy helping organizations adopt cloud-native technologies. A self-proclaimed management nerd and lifelong learner, Jamie’s early career as a software engineer evolved into a calling to improve the world through better people management. He’s the author of Visionaries, Rebels, and Machines, a sweeping narrative on the evolution of computing and leadership. Jamie now advises executives and writes about how systems, both technological and organizational, can be redesigned for the better.
Known for his systems thinking, sharp wit, and grounded view on management, Jamie has spent decades bridging the gap between technological innovation and human-centered leadership. Whether he’s decoding the transistor’s origins or dissecting what makes a high-performing executive team, Jamie is always seeking out better ways to work, grow, and lead with clarity and courage.
This episode explores the mindset shifts required to lead through ambiguity, the costs of integrity in leadership, and how discipline, self-awareness, and naivety can sometimes be your greatest assets.
Key Takeaways00:00 – Episode Recap
Jamie reflects on how childhood curiosity and Maslow’s philosophy laid the groundwork for a career blending tech and leadership.
04:27 – Acting on Inspiration Immediately
Why most people hesitate—and how taking fast, decisive action can be a leadership advantage.
07:42 – Leadership as a Moral Weight
Jamie discusses the emotional cost of doing the right thing and why real leadership isn’t always rewarded.
11:14 – The Loneliness of Idealism
From bold bets to navigating skepticism, Jamie shares what it’s like to hold the line on your values.
15:31 – Shifting Systems, Building Trust
What it really takes to lead teams through technological and cultural transformation—and why trust is the hardest part.
18:41 – Spotting Bullshit in Business
Jamie breaks down how to recognize deception in the workplace—and how to protect your team from it.
23:20 – From Sympathy to Self-Responsibility
Letting go of victimhood narratives and embracing accountability as a leadership discipline.
28:09 – Journaling, Feedback, and Decision Hygiene
Jamie shares the personal practices that help him lead with clarity and consistency.
32:03 – Psychological Safety Still Wins
Despite all the change in tech, one thing remains constant: teams thrive when they feel safe to speak up.
Resources MentionedToday on the podcast, we welcome Jeremy Shankle, full-stack engineer, AI strategist, and early adopter of automation tools across work and life at Nobody Studios.
With decades of experience in web development, startup leadership, and product strategy, Jeremy shares how going all-in on artificial intelligence has transformed how he works, lives, and thinks.
From debugging code to managing projects and planning weekends with his son, Jeremy has embraced AI as a true co-pilot. His story isn’t about replacing people—it’s about unlearning old work patterns, reducing context switching, and building smarter systems for productivity and purpose.
In this episode, we talk about Jeremy’s journey from web design and blockchain to AI-first development, and how adopting a multithreaded mindset helped him balance leadership, creativity, and everyday life in a more focused, high-leverage way.
Jeremy Shankle has worked across large tech organizations, startups, and now contributes to a fast-moving venture studio, helping teams use AI to build better products with fewer people. His thinking blends engineering discipline with human-centered innovation—exploring how tools like GPT-4 and Codex are reshaping the future of work.
Key Takeaways:01:50 – Guest Introduction: Jeremy Shankle
Barry introduces Jeremy as a product thinker and engineer at the intersection of AI, software, and strategy.
03:20 – Why Jeremy Went All-In on AI
In December, Jeremy dove deep into agents that search the web and modify code—and he hasn’t looked back.
04:02 – From Tandy 1000 to Tech Trailblazer
At age 5, Jeremy started coding on a Tandy 1000. That early start shaped his approach to learning and tech.
07:49 – Strategic Thinking Without the Switch Costs
AI helps Jeremy stay focused—no more jumping between roles or work personas all day.
10:32 – Fixing Bugs and Finding Basketball Clubs
Jeremy shows how he uses AI to squash code bugs and research activities for his son—at the same time.
15:23 – Smarter Task Management with AI
Jeremy explains how AI-infused project management tools let him create and assign tasks with ease.
22:11 – AI as an Anxiety Reducer
Whether prepping for embassy visits or crafting emails in another language, AI gives Jeremy a calm confidence.
32:31 – Confidence Without the Code Dependency
Barry shares how AI helped him stop second-guessing and start building—without always calling in an expert.
37:48 – AI Made Me Smarter, Not Dumber
By automating the grunt work, Jeremy has more time to understand the why behind every technical decision.
42:35 – What’s Next? Agent-to-Agent Collaboration
Jeremy’s most exciting frontier: AI tools that talk to each other—and get things done without constant prompts.
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Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast.
Contact here: https://bit.ly/contact-barryoreilly
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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: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."
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Contact here: https://bit.ly/contact-barryoreilly
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Today on the podcast, we welcome Faisal Hoque, author, entrepreneur, and thinker behind Transcend. With over 10 books and years of business leadership, Faisal shares how life, purpose, and challenges have shaped his journey of learning, growth, and helping others.
Known for books like Everything Connects and Transcend, Faisal blends Eastern wisdom with modern leadership. He’s worked with global firms, led startups, and speaks widely on purpose, resilience, and human-centered innovation.
In this episode, we talk about Faisal’s journey of self-growth and leadership, exploring how unlearning, flow states, and personal purpose can reshape how we lead, work, and grow in today’s fast-moving world.
Faisal Hoque is Founder and Managing Partner at Shadoka and NextChapter, Strategic Partner at CACI International Inc., and a Judge and Mentor at MIT. He’s also an investor, board member, and former CEO across various tech and business ventures. A contributor to Fast Company and IMD, he was shortlisted for the 2023 Thinkers50 Distinguished Achievement Award. Faisal is also a public speaker and former Chair of Research and Education at Altea Federation, as well as ex-Product Manager and CTO at GE Capital and Dun & Bradstreet.
Key Takeaways:Join Faisal Hoque as he shares how purpose, reflection, and human connection can guide us to grow and lead in today’s fast-changing world.
Episode Highlights:[01:00] - Episode Recap
"Faisal Hoque joins the show to talk about purpose, self-actualization, and how life’s challenges shape our leadership."
[01:34] - Guest Introduction: Faisal Hoque
"Faisal is a tech entrepreneur and author of Transcend, blending neuroscience, leadership, and personal growth."
[03:13] - Early Startups and Key Life Lessons
"My second startup failed despite big clients, then I bootstrapped my next one and wrote my first book."
[04:30] - Eastern Roots and the Search for Meaning
"Trips to Japan reconnected me with Eastern philosophy and sparked the idea for Everything Connects."
[06:01] - Redefining Self-Actualization with Purpose
"After life’s ups and downs, I began to ask: What does real success and impact look like for me now?"
[08:13] - Finding Fulfillment in Small Daily Actions
"It’s not about changing the world, it’s about helping one person and finding joy in the process."
[11:02] - The Paradox of Purpose and People in Work
"Mission statements often miss the mark, leaders must connect goals to individual purpose to inspire teams."
[14:08] - Building Regenerative and Connected Cultures
"Good leadership means creating space where people can grow, connect, and even leave to find their calling."
[18:18] - Writing, Reinvention, and Radical Openness
"Writing helps me unlearn and grow. Being open to ideas I disagree with pushes me out of my comfort zone."
[23:30] - Meditation, AI Tools, and Personal Growth
"Daily meditation and tech experiments help me reflect, stay grounded, and find new ways to improve."
[30:01] - Finding Ideas from Life and Observation
"Inspiration comes from watching the world, and writing weekly helps me reflect on change and uncertainty."
[32:51] - Focus on Effectiveness, Not Just Efficiency
"Instead of chasing speed, we must use tech to stay human, be thoughtful, and lift each other up."
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Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast.
Contact here: https://bit.ly/contact-barryoreilly
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Today on the podcast, we welcome Ja-Naé Duane, systems thinker, innovator, and author of Super Shifts. With over 20 years as a behavioral scientist and 4-time entrepreneur, Ja-Naé has guided organizations, governments, and communities through future-focused transformation.
Recognized by outlets like NPR and Businessweek, she’s passionate about reshaping how we live and work in the age of superintelligence, leveraging AR/VR, AI, and blockchain. Ja-Naé has worked with top firms like Deloitte and PWC, and is a sought-after speaker at Singularity University.
In this episode, we explore her transformative frameworks for both personal and organizational growth, highlighting the power of unlearning, integrating systems thinking, and embracing change in a tech-driven world.
Dr. Ja-Naé Duane is a Research Fellow at MIT, Faculty Director of Brown’s Innovation Management program, and a mentor in its Tech Leadership program. She’s also a Council Member at The Stimson Center, an Investor at CollX, and a Co-Founder of The Revolution Factory. At Singularity University, she teaches futures thinking and lectures in Information Systems at Bentley University, where she’s on the Blockchain Advisory Council. She’s the bestselling author of McGraw-Hill and an advisor at Teleportec.
Key Takeaways:Join Ja-Naé Duane as she discusses transformation, unlearning habits, and creating resilient systems that thrive with technology and nature.
Episode Highlights:[01:00] - Episode Recap
"Today’s guest is Ja-Naé Duane, author of Super Shifts, discussing personal and organizational transformation in the age of superintelligence."
[01:56] - Guest Introduction: Ja-Naé Duane
"Ja-Naé Duane is a leading behavioral scientist and author, helping individuals and organizations navigate the world of AI and technology."
[03:55] - Inspiration Behind Super Shifts and the Pandemic Pivot
"During COVID-19, I was called to help restart Europe, which sparked the Super Shifts concept."
[06:10] - Exploring Decentralized Systems and Resilience
"We studied nature’s decentralized systems and explored how businesses can adopt similar models to thrive under stress."
[08:33] - Unlearning Comfort and Embracing Stressors
"I realized I was too comfortable. We must introduce stressors to evolve and adapt."
[12:11] - Physical Stressors for Growth and Self-Awareness
"Physical challenges like mountain climbing help build resilience and self-awareness for my work."
[15:29] - Using AI for Productivity and Holistic Living
"We should use AI for efficiency, but also focus on creativity, wellness, and meaningful connections."
[18:56] - Transformative Models and Organizational Impact
"By unlearning old mindsets, the Transform Model helps organizations shift to sustainable, adaptable systems."
[25:07] - Embracing AI for Leadership and Change
"AI can revolutionize leadership and decision-making while keeping us human in how we integrate it."
[30:10] - AI, Time Management, and the Future of Work
"AI tools free up time by automating tasks, but we must rethink how we spend our time and adapt to new ways of working."
[35:40] - Creating Space for Innovation and Long-Term Vision
"Leaders must create space for innovation, even if uncomfortable, to shape the future."
[42:28] - AI Tools, Growth, and Embracing Change
"Our AI-native studio uses automation to streamline tasks, reduce manpower, and embrace discomfort to adapt for future success."
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