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.

• Start HR Strategy Early: Don’t wait for burnout or lawsuits—build people ops into your scaling strategy from day one.
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• Shadow Planning Is Essential: Prepare for the worst by confronting your team’s shadow behaviors and stress reactions before they sabotage growth.
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• Succession Planning Isn’t Personal: It's about scalability. Delegate early, document processes, and regularly revisit org design.
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• Growth Changes Everything: Founders need to let go to level up. What got you here won’t get you there.
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• AI in HR Is a Tool, Not a Fix: Automate the repetitive, but double down on building trust and strategic visibility.
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• HR should be the connective tissue of an organization—not the "issues and tissues" team.
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• Scaling gracefully requires confronting the emotional toll of growth, including fear of success.
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• Theresa shares how early experiences at Microsoft and ThoughtWorks shaped her belief in high-trust, high-agency cultures.
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• Executive coaching and intentional design can prevent burnout and boost retention.
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00:00 – 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.

• Theresa Cantwell on LinkedIn
• GSD HR Consulting

• LinkedIn
• Website
• Facebook
• Twitter / X
• Instagram

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.

• People Over Companies: Ron’s experience during Drexel’s collapse taught him that relationships—not institutions—are what endure.
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• Patient Capital Is a Game-Changer: Family offices can think in decades, not quarters, offering strategic advantage over traditional funds.
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• Purpose Before Profit: Legacy and social impact must anchor investment decisions.
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• Professionalization Is Essential: Governance, infrastructure, and talent are what turn capital into capability.
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• The Ego Barrier: Great wealth doesn’t guarantee great management—humility is crucial for longevity.
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1. Guiding North Star: Profit with Purpose

Anchor 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 First

Back 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 Capital

Think 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 Offices

Family 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 Philanthropy

Deploy 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.

00:00 – Episode Recap

Ron 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 Diamond

Barry 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 Syndicate

Ron explains his “first call alpha” model—aggregating capital from 100+ family offices to invest together in private markets.

08:40 – The North Star Philosophy

From 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 Alignment

Ron’s secret to identifying values-driven leaders: listen more, talk less—and show up without an agenda.

16:43 – Growth Mindset Over Scarcity

Competing with others is outdated—Ron champions an abundance mindset rooted in collaboration and long-term thinking.

20:32 – The Operational Trap for New Family Offices

Ron 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 Capital

He 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 Wealth

From 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 Institution

Ron 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 Philanthropy

Why family offices—not government or corporations—will solve many of society’s biggest challenges in the next 20 years.

45:31 – Closing Reflections

Ron shares how listeners can follow his work and why patient capital is the future of both wealth and impact.

• Ron Diamond LinkedIn
• Ron Diamond Website 
• Diamond Wealth
• Family Office World Media

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.

• Small Groups Create Big Impact: Starting events with curated small groups breaks social barriers and sets the stage for authentic connection.
• Vulnerability Builds Real Relationships: Opening up—even subtly—invites empathy and depth that surface-level networking can't achieve.
• Help Without Keeping Score: Giving without expecting reciprocity strengthens your reputation and extends your reach.
• Design Moments That Resonate: Successful events don’t depend on cocktails or keynote speeches—they’re built on meaningful first impressions.
• Asking Is a Skill, Not a Weakness: Givers often struggle to ask for support—David’s Impact Ask framework helps mission-driven people share their needs with clarity.
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• Most Networking Events Are Designed to Fail: Traditional formats emphasize aesthetics over connection—David redesigns them to foster immediate, meaningful dialogue.
• Shared Vulnerability Activates Group Trust: Structured conversations with depth-based prompts unlock faster bonding and community-building.
• Music as a Metaphor for Human Connection: David draws from his training as a classical composer to illustrate how relationships, like instruments, must resonate and harmonize.
• Clarity Makes Asking Easier: The “Impact Ask” framework simplifies how to articulate passion, purpose, and the kind of help you need.
• Your Reputation Travels Faster Than You Do: David’s work shows that investing in authentic relationships amplifies your presence—even when you're not in the room.
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00:00 – 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.

• Orchestrating Connection – Book
• David Homan on LinkedIn

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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.

• Trauma 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.

• Redefine 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.

00:18 – 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.

Useful Resources

• The Sound of Freedom by Paul Hutchinson Amazon Bestseller
• The 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 Guest

• Get the first 3 chapters of Paul’s book for free: www.soundoffreedombook.com
• Liberating Humanity website: liberating-humanity.com
• Child Liberation Website: childliberation.org
• Youtube - youtube.com/@liberatinghumanity
• Instagram - instagram.com/liberating.humanity
• Facebook - facebook.com/liberating.humanity
• TikTok - tiktok.com/@liberating.humanity
• LinkedIn - linkedin.com/in/paulhutch
• X - x.com/paulhutchinson

Follow Barry O’Reilly

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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.

• Generosity 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.

• Redefine 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.

00:00 – 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.

Brad 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.

• Craft First, Climb Later: David shares why stepping back from leadership to deepen his sales craft at Waracle gave him the clarity and credibility to lead more effectively.
• Lead Without Knowing Everything: CEOs don't need all the answers—they need to ask better questions and create space for their teams to excel.
• AI Starts with Literacy: Leaders must understand AI fundamentals to steer transformation and avoid becoming disconnected from how value is created.
• From Specialist to Generalist: The CEO role is about orchestration—shifting from doing to enabling across functions and disciplines.
• Human Connection Still Wins: At Waracle and beyond, trust, empathy, and meaningful relationships still drive long-term business success in an AI-powered world.

• Redefine Leadership as Service: A CEO’s job is to help others succeed, not to control every decision or be the expert in the room.
• Ask Better Questions: Using frameworks like the probing pyramid can unlock better thinking and faster alignment across teams.
• Don’t Automate the Human: AI can accelerate delivery, but it can’t replace the emotional intelligence and trust that drive real impact.
• Create Space for Reflection: Strategic pauses and structured dialogue lead to more thoughtful, inclusive decisions—especially in hybrid teams.
• Unlearn to Move Forward: Leaders need to let go of outdated habits and create the conditions for new thinking to thrive.

Useful Resources

• David Tuck on LinkedIn
• Waracle on LinkedIn
• Waracle Website
• David Bowie’s 1999 interview on the future of the internet
• Waracle’s AI Literacy Program

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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.

• Start with Attention, Not Execution: The first job is proving demand, not building features.
• The Fluency Equation: Adoption is driven by desire, but also requires lowering inexperience, complexity, and perceived consequence.
• Redefine Product-Market Fit: Medium fit — how people find, try, and pay — is just as important as what you offer.
• Reverse Your GTM Strategy: Work backward from demand instead of forward from the product.

• Test Before You Build: Demand validation should come before development or scaling.
• Have a Disagreement with the World: Bold startups are born from challenging norms, not just meeting expectations.
• Use Familiar Behaviors to Drive Adoption: Anchoring new tools to existing habits lowers friction and boosts engagement.
• Practice Ethical Persuasion: Subversive tactics work best when they respect users and build long-term trust.

00:00 – 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.

Useful Resources:

• Alistair Croll on LinkedIn
• Just Evil Enough by Alistair Croll & Emily Ross
• Lean Analytics by Alistair Croll & Ben Yoskovitz
• Unlearn Episode with Emily Ross 
• Startupfest
• Never Split the Difference by Chris Voss
• How Minds Change by David McRaney

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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.

• Act on Inspiration Fast: Jamie shares why taking immediate action on a good idea is a rare but powerful leadership move.
• Leadership as a Moral Responsibility: Decision-making isn’t just strategic—it’s ethical, emotional, and deeply human.
• Naïveté as a Strength: Why approaching challenges with curiosity and a beginner’s mindset can spark unexpected breakthroughs.
• Letters to Self as Feedback Loops: How Jamie uses journaling to reflect, recalibrate, and lead with discipline.
• Psychological Safety Isn’t Optional: The timeless (and still underused) foundation of every high-performing tech team.
• Bullsh*t Detection 101: From recognizing deceptive behavior to building a culture of honesty, trust, and clarity.
• Managing Technologists is Solved: The real challenge isn’t how to manage engineers—it’s having the discipline to do what works.

00:00 – 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.

• Visionaries, Rebels, and Machines – Jamie Dobson
• Maslow on Management – Abraham Maslow
• The Hard Thing About Hard Things – Ben Horowitz
• Spy the Lie – Philip Houston et al.
• Continuous Discovery Habits – Teresa Torres
• The Soul of a New Machine – Tracy Kidder
• Peter Drucker’s writings on action and management

Today 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.

• Going All-In on AI: Jeremy shares what happened when he decided to run everything through GPT tools—from coding to shopping.
• 
  
• Unlearning Multitasking: Why AI helps him focus more by batching work, parallelizing tasks, and context switching less.
• Human First, Tech Forward: How AI frees up space for better thinking, parenting, and problem-solving.
• Changing How We Work: Smaller teams, higher output, fewer blockers.
• Life OS Upgrade: From weekend planning to debugging code, AI is now part of Jeremy’s daily operating system.

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.

• Jeremy Shankle
• Nobody Studios
• OpenAI Codex
• GPT-4 with Memory and Deep Research Tools
• Tools Mentioned: ChatGPT Pro, Operator, Browser MCP, Codex

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: [email protected]

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.

• 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.

• 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.

[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: [email protected]