Unlearn

Latest Episodes:

The Sound of Freedom and Healing Trauma with Paul Hutchinson Aug 12, 2025

Show notes

Paul Hutchinson’s life story reads like a thriller, but his mission is deeply real and urgent. Once a multi-billion dollar fund manager, Paul transformed his life to become an undercover operative, leading more than 70 rescue missions across 15 countries to free thousands of children trapped in sex trafficking. He is the true-life inspiration behind the Sound of Freedom movie and the author of The Sound of Freedom: True Stories That Inspired the Film, offering a raw, unfiltered look at what it takes to confront humanity’s darkest realities and bring hope to the most vulnerable.

This episode goes far beyond heroism. We explore the complexities and personal costs of Paul’s work—from how his background in private equity uniquely positioned him to negotiate with traffickers, to the emotional and psychological toll of seeing trauma up close. Paul also shares vital lessons on protecting your children, what really works in combating trafficking, and why healing—beyond extraction—is the ultimate rescue.

Some stories are tough to face but impossible to turn away from. Paul’s journey is a powerful reminder of resilience, transformation, and what true leadership means when you dare to engage with the hardest truths.

Key Takeaways

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.

Additional Insights

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.

Episode Highlights

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

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Give First and the Ripple Effect of Generosity with Brad Feld Jul 29, 2025

Show notes

What if generosity—not hustle—is your greatest competitive advantage?

Brad Feld—co-founder of Foundry Group, Mobius Venture Capital, and startup accelerator Techstars—joins Barry to explore the transformative philosophy of “Give First,” a mindset that’s reshaped how founders, investors, and mentors build lasting companies and vibrant startup ecosystems. Brad has spent over three decades cultivating startup communities by putting people before profit and helping others without expecting anything in return.

In this episode, he shares the mindset shifts that fueled Techstars’ global influence, how mentorship evolves from hierarchy to peer learning, and why sustainable success stems from playing the long game. A conversation full of clarity, candor, and challenge—for anyone rethinking what it means to lead, contribute, and create.

Key Takeaways

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.

Additional Insights

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.

Episode Highlights:

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.

Episode Resources

Brad Feld on LinkedIn: Brad Feld

Foundry Group on LinkedIn: Foundry Group

Foundry Group website: foundrygroup.com

Techstars website: techstars.com

Why AI-First Digital Product Consultancies Will Win Big with David Tuck Jul 15, 2025

Show notes

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.

Key Takeaways

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.

Additional Insights

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

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Bold Go-To-Market Tactics: Just Evil Enough to Win with Alistair Croll Jul 01, 2025

Show notes

What if the biggest risk in your business isn’t building the product but realizing no one wants it? In this Unlearn episode, I’m joined by Alistair Croll, technologist, entrepreneur, and bestselling author of Lean Analytics, for a candid and clever conversation on rethinking product development, marketing, and demand generation.

Alistair’s work focuses on data-driven innovation and human behavior. He co-authored Just Evil Enough: The Subversive Marketing Handbook, a playbook for bending the rules to win in the attention economy. He has chaired global tech conferences like O’Reilly’s Strata and currently leads Startupfest, where he helps founders turn clever ideas into competitive advantage.

Known for blending insight with humor, Alistair unpacks why subversive creativity, not perfection, often wins. From the “fluency equation” to Burger King’s clever customer acquisition tactics, he reveals how unconventional strategies generate meaningful traction. This episode explores the science of subversive marketing, reframes how we think about product launch risk, and dives into the mindset shifts leaders need to stay relevant in the AI era.

Key Takeaways

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.

Additional Insights

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.

Episode Highlights:

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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Email: hello@barryoreilly.com

Visionaries, Rebels, and Machines: Getting the Best of All with Jamie Dobson (Explicit) Jun 17, 2025

Show notes

Today on the Unlearn podcast, we welcome Jamie Dobson, technologist, entrepreneur, and a leader known for building systems that connect innovation with purpose. He joins us to share a deeply reflective journey: spanning childhood curiosity, extreme programming, leadership challenges, and the hard truths of building a company with intention.

Jamie Dobson is the co-founder and former CEO of Container Solutions, a consultancy helping organizations adopt cloud-native technologies. A self-proclaimed management nerd and lifelong learner, Jamie’s early career as a software engineer evolved into a calling to improve the world through better people management. He’s the author of Visionaries, Rebels, and Machines, a sweeping narrative on the evolution of computing and leadership. Jamie now advises executives and writes about how systems, both technological and organizational, can be redesigned for the better.

Known for his systems thinking, sharp wit, and grounded view on management, Jamie has spent decades bridging the gap between technological innovation and human-centered leadership. Whether he’s decoding the transistor’s origins or dissecting what makes a high-performing executive team, Jamie is always seeking out better ways to work, grow, and lead with clarity and courage.

This episode explores the mindset shifts required to lead through ambiguity, the costs of integrity in leadership, and how discipline, self-awareness, and naivety can sometimes be your greatest assets.

Key Takeaways

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.

Episode Highlights

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.

Resources Mentioned

What Happens When You Go All-In in Work and Life on AI with Jeremy Shankle Jun 03, 2025

Show notes

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.

Key Takeaways:

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.

Episode Highlights:

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.

Resources

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

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The Future of Housing and Modular Home Building with John Avrett May 21, 2025

Show notes

Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast.

Contact here: https://bit.ly/contact-barryoreilly

____________________________________________________________

Welcome to UNLEARN, the podcast where we talk about bold ideas, fresh thinking, and the mindset shifts needed for real change. Today, I’m excited to welcome John Avrett, former U.S. diplomat, aerospace and electrical engineer, and now Founder and CEO of Hive Modular. With past roles in the U.S. Air Force, U.S. Navy, and Department of State, John is leading a new wave of modular home building in the Philippines, tackling the global housing crisis with factory-made homes and smart design.

John isn’t just a builder; he also loves solving big problems and making homes better for everyone. His journey from engineering and diplomacy to modular homes shows how thinking differently can help fix housing issues in new ways, especially by building smarter and faster in places that need it most.

John has worked across engineering and global trade before starting his company to build homes in a new way. At his factory in the Philippines, his team makes modular houses using a process like a car factory, helping build faster and cheaper. He focuses on smart design and shipping, bringing homes to places that need them, while using skills from aerospace and diplomacy to guide his work.

Key Takeaways:

Fixing Housing Problems: John shares how factory-made homes can help more people.
Starting a Business: What he learned from taking a big risk to follow his dream.
Thinking Differently: Why new ways of thinking are key to solving old problems.
Global Experience: How living and working abroad shaped his big ideas.
Smart Building: How using a car-like factory process makes building homes faster.

Additional Insights:

Mixing Tech and Building: John shows how factory skills can improve home building.
Working in New Markets: What it takes to build homes in places with big needs.
Learning from the Past: How John’s old jobs help him find smart new ways to build.
Solving Real Problems: How he uses design to make homes faster and cheaper.
Adapting to Change: Why being open to new ideas helped grow his company.

Join John Avrett as he shares how bold ideas, smart building, and global thinking can help solve housing needs and spark new ways to grow in today’s world.

Episode Highlights:

[00:10] - Episode Recap

"John Avrett joins to talk about solving housing issues with modular homes and lessons from past careers."

[01:38] - Guest Introduction: John Avrett

"John is an ex-aerospace engineer and U.S. diplomat now building smart, factory-made homes in the Philippines."

[04:48] - Museum Visit Sparks a Big Idea

"A prefab home exhibit opened John’s eyes to a better way of building and inspired his mission."

[07:25] - From Engineer to Diplomat to Builder

"John shares how his global work helped him spot the housing crisis as a real problem to fix."

[10:09] - Why Housing Innovation Fell Behind

"Homes take longer and cost more today than in the 1960s, John explains why change is overdue."

[13:07] - Rethinking Risk to Start a Company

"Leaving a stable job was tough, but learning to see risk in a new way helped John take the leap."

[14:53] - Turning Homes Into a Factory Process

"John explains how car-style production lines and steel frames help build better, faster homes."

[19:42] - Blending Standard Design with Custom Feel

"Standard frames and flexible layouts allow homes to feel unique while staying easy to build."

[22:24] - Labor and Logistics in Home Building

"Even in a factory, homes take skilled work, and every site brings its own tricky challenges."

[27:02] - Strategy, Scaling, and a Life-Changing Book

"John explains how scaling isn’t about more small homes but bigger impact and how a book by Annie Duke helped shape his thinking."

[33:18] - Global Momentum and What’s Next

"John shares why support from countries like Canada and Australia shows prefab housing is gaining ground and how rising costs may push the U.S. to follow soon."

FOLLOW THE GUEST:

LinkedIn Accounts:

John Avrett: https://www.linkedin.com/in/john-avrett-26891944/
Hive Modular: https://www.linkedin.com/company/hivemodular/
US Department of State: https://www.linkedin.com/company/doscareers/
US Navy: https://www.linkedin.com/company/us-navy/
United States Air Force: https://www.linkedin.com/company/united-states-air-force/

Websites:

Hive Modular: https://www.hive-modular.com/
US Department of State: https://www.state.gov/
US Navy: https://www.navy.mil/
United States Air Force: https://www.airforce.com/

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The New Science of Self-Actualization for Founders to Reinvent Identity & Find Meaning - Faisal Hoque May 07, 2025

Show notes

Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast.

Contact here: https://bit.ly/contact-barryoreilly

____________________________________________________________

Today on the podcast, we welcome Faisal Hoque, author, entrepreneur, and thinker behind Transcend. With over 10 books and years of business leadership, Faisal shares how life, purpose, and challenges have shaped his journey of learning, growth, and helping others.

Known for books like Everything Connects and Transcend, Faisal blends Eastern wisdom with modern leadership. He’s worked with global firms, led startups, and speaks widely on purpose, resilience, and human-centered innovation.

In this episode, we talk about Faisal’s journey of self-growth and leadership, exploring how unlearning, flow states, and personal purpose can reshape how we lead, work, and grow in today’s fast-moving world.

Faisal Hoque is Founder and Managing Partner at Shadoka and NextChapter, Strategic Partner at CACI International Inc., and a Judge and Mentor at MIT. He’s also an investor, board member, and former CEO across various tech and business ventures. A contributor to Fast Company and IMD, he was shortlisted for the 2023 Thinkers50 Distinguished Achievement Award. Faisal is also a public speaker and former Chair of Research and Education at Altea Federation, as well as ex-Product Manager and CTO at GE Capital and Dun & Bradstreet.

Key Takeaways:

Unlearning past beliefs helps us grow and adapt in a changing world.
True purpose comes from small daily actions, not big goals.
Flow, gratitude, and reflection can boost personal and work life.

Additional Insights:

Let go of chasing success and focus on work that feels meaningful.
Use reflection, meditation, and learning to stay sharp and inspired every day.

Join Faisal Hoque as he shares how purpose, reflection, and human connection can guide us to grow and lead in today’s fast-changing world.

Episode Highlights:

[01:00] - Episode Recap

"Faisal Hoque joins the show to talk about purpose, self-actualization, and how life’s challenges shape our leadership."

[01:34] - Guest Introduction: Faisal Hoque

"Faisal is a tech entrepreneur and author of Transcend, blending neuroscience, leadership, and personal growth."

[03:13] - Early Startups and Key Life Lessons

"My second startup failed despite big clients, then I bootstrapped my next one and wrote my first book."

[04:30] - Eastern Roots and the Search for Meaning

"Trips to Japan reconnected me with Eastern philosophy and sparked the idea for Everything Connects."

[06:01] - Redefining Self-Actualization with Purpose

"After life’s ups and downs, I began to ask: What does real success and impact look like for me now?"

[08:13] - Finding Fulfillment in Small Daily Actions

"It’s not about changing the world, it’s about helping one person and finding joy in the process."

[11:02] - The Paradox of Purpose and People in Work

"Mission statements often miss the mark, leaders must connect goals to individual purpose to inspire teams."

[14:08] - Building Regenerative and Connected Cultures

"Good leadership means creating space where people can grow, connect, and even leave to find their calling."

[18:18] - Writing, Reinvention, and Radical Openness

"Writing helps me unlearn and grow. Being open to ideas I disagree with pushes me out of my comfort zone."

[23:30] - Meditation, AI Tools, and Personal Growth

"Daily meditation and tech experiments help me reflect, stay grounded, and find new ways to improve."

[30:01] - Finding Ideas from Life and Observation

"Inspiration comes from watching the world, and writing weekly helps me reflect on change and uncertainty."

[32:51] - Focus on Effectiveness, Not Just Efficiency

"Instead of chasing speed, we must use tech to stay human, be thoughtful, and lift each other up."

FOLLOW THE GUEST:

LinkedIn Accounts:

Faisal Hoque: https://www.linkedin.com/in/faisalhoque/
NextChapter: https://www.linkedin.com/company/nextchapterorg/
Shadoka: https://www.linkedin.com/company/shadoka/
CACI International Inc: https://www.linkedin.com/company/caci-international-inc/
MIT: https://www.linkedin.com/school/mit/
Fast Company: https://www.linkedin.com/company/fast-company/
IMD: https://www.linkedin.com/school/imd-business-school/
Altea Federation: https://www.linkedin.com/company/alteafederation/
GE Capital: https://www.linkedin.com/company/gecapital/
Dun & Broadsheet: https://www.linkedin.com/company/dun-&-bradstreet/

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Unlearning Legacy Systems to Build Antifragile AI Operating Models with Ja-Naé Duane Apr 23, 2025

Show notes

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Contact here: https://bit.ly/contact-barryoreilly

____________________________________________________________

Today on the podcast, we welcome Ja-Naé Duane, systems thinker, innovator, and author of Super Shifts. With over 20 years as a behavioral scientist and 4-time entrepreneur, Ja-Naé has guided organizations, governments, and communities through future-focused transformation.

Recognized by outlets like NPR and Businessweek, she’s passionate about reshaping how we live and work in the age of superintelligence, leveraging AR/VR, AI, and blockchain. Ja-Naé has worked with top firms like Deloitte and PWC, and is a sought-after speaker at Singularity University.

In this episode, we explore her transformative frameworks for both personal and organizational growth, highlighting the power of unlearning, integrating systems thinking, and embracing change in a tech-driven world.

Dr. Ja-Naé Duane is a Research Fellow at MIT, Faculty Director of Brown’s Innovation Management program, and a mentor in its Tech Leadership program. She’s also a Council Member at The Stimson Center, an Investor at CollX, and a Co-Founder of The Revolution Factory. At Singularity University, she teaches futures thinking and lectures in Information Systems at Bentley University, where she’s on the Blockchain Advisory Council. She’s the bestselling author of McGraw-Hill and an advisor at Teleportec.

Key Takeaways:

Stress isn’t the enemy; using it intentionally can fuel growth and resilience.
To thrive in the future, we must unlearn outdated systems and develop an antifragile mindset.
Superintelligence and AI are crucial tools for creativity, reflection, and decision-making.

Additional Insights:

Let go of outdated thinking to make room for fresh, innovative approaches.
Use AI and other tools to boost productivity and enhance creativity in your work.

Join Ja-Naé Duane as she discusses transformation, unlearning habits, and creating resilient systems that thrive with technology and nature.

Episode Highlights:

[01:00] - Episode Recap

"Today’s guest is Ja-Naé Duane, author of Super Shifts, discussing personal and organizational transformation in the age of superintelligence."

[01:56] - Guest Introduction: Ja-Naé Duane

"Ja-Naé Duane is a leading behavioral scientist and author, helping individuals and organizations navigate the world of AI and technology."

[03:55] - Inspiration Behind Super Shifts and the Pandemic Pivot

"During COVID-19, I was called to help restart Europe, which sparked the Super Shifts concept."

[06:10] - Exploring Decentralized Systems and Resilience

"We studied nature’s decentralized systems and explored how businesses can adopt similar models to thrive under stress."

[08:33] - Unlearning Comfort and Embracing Stressors

"I realized I was too comfortable. We must introduce stressors to evolve and adapt."

[12:11] - Physical Stressors for Growth and Self-Awareness

"Physical challenges like mountain climbing help build resilience and self-awareness for my work."

[15:29] - Using AI for Productivity and Holistic Living

"We should use AI for efficiency, but also focus on creativity, wellness, and meaningful connections."

[18:56] - Transformative Models and Organizational Impact

"By unlearning old mindsets, the Transform Model helps organizations shift to sustainable, adaptable systems."

[25:07] - Embracing AI for Leadership and Change

"AI can revolutionize leadership and decision-making while keeping us human in how we integrate it."

[30:10] - AI, Time Management, and the Future of Work

"AI tools free up time by automating tasks, but we must rethink how we spend our time and adapt to new ways of working."

[35:40] - Creating Space for Innovation and Long-Term Vision

"Leaders must create space for innovation, even if uncomfortable, to shape the future."

[42:28] - AI Tools, Growth, and Embracing Change

"Our AI-native studio uses automation to streamline tasks, reduce manpower, and embrace discomfort to adapt for future success."

Follow Our Guest

LinkedIn Accounts:

Ja-Naé Duane: https://www.linkedin.com/in/janaeduane/
MIT: https://www.linkedin.com/school/mit/
Brown University School of Professional Studies: https://www.linkedin.com/school/brownsps/
The Revolution Factory: https://www.linkedin.com/company/the-revolution-factory/
Pre-order the First Edition Hardback of Super Shifts today at https://www.target.com/p/supershifts-by-ja-nae-duane-steve-fisher-hardcover/-/A-1001693948

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From Fashion to Real Estate, Unlearning to Realign Purpose and Scale with Francesca Cortesi Apr 09, 2025

Show notes

Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast.

Contact here: https://bit.ly/contact-barryoreilly

____________________________________________________________

Today on the Unlearn Podcast, I’m thrilled to be joined by Francesca Cortesi, CPO and Founder of Prodotto Collective, a product visionary, transformational leader, and someone who truly understands what it takes to build beloved products and high-performing teams.

Francesca was the Chief Product Officer at Hemnet, Sweden’s leading property platform, where she played a pivotal role in scaling the product organization and driving the company through a successful IPO in 2021. Under her leadership, Hemnet achieved consistent double-digit growth, became one of Sweden’s most appreciated apps, and stood out as a top performer on the Swedish stock exchange.

But her story goes far beyond business metrics. Francesca led cultural shifts too, transitioning the company language to English and increasing female representation in tech, proving that growth and inclusion can go hand in hand.

In this episode, we explore how Francesca thinks about unlearning as a tool for personal and organizational growth, building product excellence at scale, and creating environments where diverse teams thrive.

Key Takeaways:

Changing careers: Francesca switched from fashion in Milan to tech in Sweden after many rejections, showing strong resilience.
Product Management: Asking many questions helped her shift from project management to product management.
Asking for Help: Great leaders don't need to know everything; asking for help builds stronger teams.
Idea company size: Francesca thrives best in scale-up companies (40–400 people), not large corporations.
Unlearning and Growth: Every new role required Francesca to "unlearn" old ways to adapt to new challenges.

Additional Insights:

Changing Roles: Your job changes when your company grows, so be ready for change.
Know your strength: Understand clearly what you’re good at and where you fit best.
Start Fresh: Always approach new tasks like you're learning for the first time.

Get ready for a powerful conversation with Francesca Cortesi on embracing change, scaling with intention, and building inclusive, high-performing product teams that thrive through continuous unlearning and growth.

Episode Highlights:

[01:00] - Episode Recap

"Welcome to the Unlearn Podcast, Exploring career shifts, new leadership styles, and how to build strong product teams."

[02:03] - Guest Introduction: Francesca Cortesi

"Francesca, former Chief Product Officer at Hemnet, helped scale the product and led the company to a successful 2021 IPO."

[03:22] - From Milan Fashion to Stockholm: The First Career Pivot

"I worked in fashion, got a translator job in Sweden, and decided to move."

[07:10] - Facing Rejection and Redefining Identity

"I tried returning to fashion, but it wasn’t working, time to move on."

[10:13] - Discovering Product Management Through Curiosity and Questioning

"I kept asking questions, turns out, that curiosity led me into product management."

[15:20] - What Francesca Had to Unlearn

"As a product manager, I had to leave behind what worked before, it’s always contextual."

[19:56] - Transition from Individual Contributor to Product Leader

"My first leadership role taught me to stop copying others and find my own style."

[24:54] - Why Role Expectations Must Be Rewritten During Scaling

"Too many questions about roles and success? That’s your sign to pause and redefine expectations."

[27:52] - Realizing Where She Thrives: The Scaleup Stage

"My sweet spot? Companies ready to scale after finding product-market fit."

[37:24] - From Operator to Advisor: Unlearning and Redefining Impact

"New roles come with new expectations, especially the ones you set for yourself."

Follow Our Guest:

LinkedIn Accounts:

Francesca Cortesi: https://www.linkedin.com/in/francesca-cortesi/
Prodotto Collective: https://www.linkedin.com/company/prodotto-collective/
Hemnet: https://www.linkedin.com/company/hemnet/

Websites:

Prodotto Collective (Francesca’s Personal Site): https://www.francescacortesi.com/

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