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.

• From 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.

• Unlearning 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.

00:00 – Episode Recap

Steve 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 Elliott

Barry 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 shifts

From a consulting career at PwC to software experiments that took off—how Steve found his way into entrepreneurship.

08:55 – From technologist to founder

The 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 decisions

Why enterprise tools fail to support real-time, strategic decisions—and how Steve is tackling the problem differently.

17:50 – The rise of agentic frameworks

How Dotwork is using knowledge graphs and agentic AI to reflect the dynamic, decentralized nature of modern organizations.

23:31 – Breaking through transformation fatigue

How Dotwork builds trust not through marketing, but by showing real, contextual results fast.

26:23 – Beyond dashboards: AI-native UX

Why 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 AI

Barry shares his experience coaching executives on AI—and why hands-on experimentation is the only path to mastery.

36:07 – Context engines for agents

Steve explains how Dotwork unintentionally became a context memory platform—crucial for the future of autonomous agents.

40:36 – Magic moments in enterprise UX

When engineering hasn’t seen the reports their software generates—because the platform is that intuitive.

43:17 – Closing Reflections

Steve 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.

• Unlearning expertise-dependence: Cass shifted from relying on experts to co-creating solutions with AI tools before engaging others.
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• 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.
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• Low-code leadership: Cass, a self-described non-technical leader, built HR bots and reimagined policies through practical AI applications.
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• Scaling culture through consistency: AI chatbots improved response times, standardized answers, and gave insight into employee concerns.
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• Embedding experimentation: Teams are encouraged to ask, "What should I stop doing?"—sparking a culture of reinvention and initiative.
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• Progyny’s “Super Fans” initiative reframes AI gains as an opportunity to deepen customer and employee relationships.
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• Training is done in cohorts to build shared understanding and reduce AI anxiety.
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• Cross-functional collaboration with junior team members—like the intern who built the HR bot—shows how innovation can come from any level.
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• Cass uses AI to simplify and globalize complex frameworks like competency models, improving alignment across teams and geographies.
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00:00 – 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.

• Progyny: https://www.progyny.com
• Connect with Cassandra Pratt: LinkedIn
• AI Executive Coaching by Barry: https://barryoreilly.com

• LinkedIn: linkedin.com/in/barryoreilly
• Website: barryoreilly.com
• Facebook: facebook.com/barryoreillyauthor
• Twitter/X: x.com/barryoreilly
• Instagram: instagram.com/barryoreilly

When most leaders think about transformation, they reach for tools and tactics. But real, lasting change doesn’t start with new methods—it starts with culture. In this episode, I sit down with Phil Gilbert, the former General Manager of Design at IBM, who led one of the boldest reinventions in corporate history. After selling his third startup to IBM in 2010, Phil was asked to transform how IBM’s teams worked using design thinking and agile. That effort reshaped the experience of over 400,000 employees and became the subject of a Harvard Business School case study, the documentary The Loop, and coverage in the New York Times and Fortune.

We explore how culture drives outcomes, why the team is the atomic unit of change, and how to design a leadership structure that earns trust and creates momentum. Phil brings sharp insight, rich stories, and practical frameworks drawn from a 45-year career spanning startups, scale-ups, and global enterprises. If you’re leading change—or trying to get others to believe in it—this conversation is your blueprint.

Phil Gilbert is best known for scaling IBM’s global design transformation. He was inducted into the New York Foundation for the Arts Hall of Fame in 2018 and named an Oklahoma Creativity Ambassador in 2019. Since retiring from IBM in 2022, Phil has focused on helping business and military leaders shift culture at scale to improve innovation and team performance.

• Culture is the system: Real transformation means rewiring people, practices, and places—not just teaching new skills.
• Teams are the atomic unit of change: Change doesn’t scale through individual mandates. It scales when cross-functional teams deliver new outcomes.
• Design scales empathy: Phil shares how design thinking isn’t just about aesthetics—it’s a tool for scaling understanding and improving systems.
• Transformation needs protection: Change teams need structural support and a leadership “shell” that shields them while engaging the broader org.
• Momentum beats mandates: Leaders can’t impose change—they must earn it by showing results, listening deeply, and integrating across silos.

• "Every day is a prototype": Phil’s mantra that gives teams permission to change, test, and learn continuously.
• The virus model of leadership: To spread new ways of working, Phil designed his leadership team like a virus—with spikes into HR, finance, comms, and IT.
• Designers aren’t the barrier—systems are: In companies with weak design reputations, the problem isn’t the designers. It’s the culture around them.
• Shadow IT kills transformation: Real progress happens when change leaders partner with CIOs—not work around them.
• Most AI efforts are missing the point: Phil argues that AI transformation fails when it focuses on individuals instead of improving team-level outcomes.

00:00 - Episode Recap

Barry O’Reilly recaps the episode’s theme, discussing leadership challenges, reclaiming strategic focus, and leveraging frameworks, executive habits, and AI to drive impactful business outcomes.

2:26 - Guest Introduction

Barry introduces Phil Gilbert, renowned for leading a major cultural transformation at IBM through human-centered design. He previews Phil’s new book, “Irresistible Change,” and sets expectations for a discussion on leadership, empathy, and executing change at scale.

3:21 - Official Start of Conversation

Phil Gilbert reflects on pivotal career moments, including his experience founding early startups, the challenge of driving adoption for new technologies, and discovering the power of empathy and design. He introduces his guiding philosophy, “every day is a prototype.”

9:15 - The Power of Prototyping and Embracing Change

Phil explains how prototyping and a willingness to challenge the status quo lead to organizational and personal growth. He shares his “every day is a prototype” mantra and stresses the role of openness in innovation.

13:48 - Culture as a Driver of Outcomes

Phil outlines his formula for driving real change, focusing on people, practices, and places. He discusses his use of journaling and intentional observation to systematically build curiosity and support for change in teams.

20:47 - Designing Transformation at Scale

Phil discusses the challenge of leading IBM’s company-wide design movement. He explains his strategy to reach and influence 400,000 employees and the importance of building a diverse leadership team to support transformative efforts.

31:29 - Practical Tactics for Organizational Change

Phil details the need to integrate HR, tooling, and communications into the transformation process, sharing stories about revamping career ladders and piloting new tools. He emphasizes collaboration and transparency with key stakeholders like HR and CIOs.

37:51 - Lessons for Modern AI Transformation

Phil and Barry examine current challenges with AI change efforts, arguing that teams—not just individuals—are the fundamental units for successful transformation. They discuss why team-level outcomes should guide measurement and strategy for adopting new technologies.

41:09 - Hopes and Irresistible Change for the Future

Phil shares his vision for the next wave of business transformation, especially regarding AI. Drawing inspiration from cloud computing’s impact, he hopes leaders will adopt principles that empower teams to drive industry-defining change.

• Phil Gilbert – Irresistible Change (book): Buy on Amazon
• Connect with Phil on LinkedIn: Phil Gilbert
• Barry’s blog on AI

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

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.

• Clarity 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.

• Positioning 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.

00:00 – Episode Recap

Anthony 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 Pierri

Barry 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 Everything

Why 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 Advantage

Anthony 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 Positioning

Don’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 Positioning

As 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 Yourself

Positioning isn’t self-promotion—it’s about telling a compelling story that reflects your champion’s reality.

35:15 – The “Tell Me More” Effect

Great 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 Asset

The 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 Scale

Anthony 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 Converts

Barry and Anthony unpack how to use messaging anchors, problem framing, and customer-centric storytelling to guide your homepage narrative.

• FletchPMM Website
• Anthony Pierri on LinkedIn
• April Dunford – Obviously Awesome
• Wynter – Message Testing

• LinkedIn
• Outlier Venture Partners
• Facebook
• Twitter/X
• Instagram

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.

• Loneliness Is a Biological Threat: Your brain interprets social disconnection like hunger or pain—not just a mood, but a warning signal.
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• Small In-Person Moments Matter: Even brief, face-to-face interactions boost mood and cognitive function more than digital ones.
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• Isolation Damages the Brain: Chronic loneliness raises cortisol, shrinks memory centers, and can shorten your lifespan.
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• Introverts Still Need People: Social time benefits everyone—introverts just hit their saturation point sooner.
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• Generosity Is Hardwired: From rats to dolphins, the impulse to connect and give is deeply embedded in our biology.
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• Connection Requires Unlearning: Independence and solitude aren't always virtues—sometimes they’re survival myths in disguise.
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• Social prediction systems in the brain were scrambled by COVID—and many people still haven’t recalibrated.
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• Most people think they’re worse-than-average at socializing, which fuels avoidance and false self-judgment.
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• Digital tools remove the social cues—tone, expression, touch—that our brains need to feel emotionally nourished.
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• Empathy is not automatic—it’s biased and trainable, shaped by exposure to difference and intention.
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• Rebuilding community isn’t just good for you—it’s essential for physical, mental, and societal health.
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00:00 – Episode Recap

Ben 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 Rein

Barry 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 Predictions

Ben 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 Loneliness

Ben 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 Friends

Barry 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 Fear

Ben 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 Connection

Barry 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 Matters

Ben 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 Nature

Ben shares surprising studies showing kindness and empathy across the animal kingdom—and what humans can learn from them.

39:22 – Closing Reflections

Barry and Ben wrap with a call to action: prioritize connection, embrace kindness, and use what we know to better ourselves and others.

• Why Brains Need Friends by Dr. Ben Rein
• Dr. Ben Rein on LinkedIn
• Ben’s popular science content on Instagram and TikTok

• LinkedIn
• Personal Site
• Facebook
• Twitter
• Instagram

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

Follow Barry O’Reilly

• LinkedIn: https://www.linkedin.com/in/barryoreilly
• Website: https://barryoreilly.com
• Facebook: https://www.facebook.com/barryoreillyauthor/
• Twitter (X): https://x.com/barryoreilly
• Instagram: https://www.instagram.com/barryoreilly/

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

• LinkedIn: https://www.linkedin.com/in/barryoreilly
• Website: https://barryoreilly.com
• Facebook: https://www.facebook.com/barryoreillyauthor/
• Twitter (X): https://x.com/barryoreilly
• Instagram: 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.

• 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