Unlearn

Barry O'Reilly

The way to think differently is to act differently and get comfortable with being uncomfortable. For business leaders, entrepreneurs, managers and anyone who wants to improve how they work and live: Welcome to the Unlearn Podcast. Host Barry O’Reilly, author of Unlearn and Lean Enterprise seeks to synthesize the superpowers of extraordinary individuals into actionable strategies you can use—to Think BIG, start small and learn fast, and find your edge with excellence.

  1. Artificial Organizations: Judgment at Speed in the Age of AI

    2D AGO

    Artificial Organizations: Judgment at Speed in the Age of AI

    AI isn’t about productivity. It’s about presence. In this special episode, the tables turn and I’m interviewed by Sham Colegado about my new book, Artificial Organizations. We explore why 95% of AI projects fail, why executives don’t want more tools — they want their life back — and how the real competitive edge isn’t automation, but judgment at speed. If you’ve been overwhelmed by the explosion of AI tools or unsure where to start, this episode will help you reframe the conversation. This isn’t about doing more. It’s about deciding better — faster, with clarity and confidence — by combining human instinct with machine intelligence. Key TakeawaysAI Used Only for Productivity Fails: When AI is treated as a cost-cutting tool instead of a transformation system, it rarely creates lasting value.Presence Is the Real Advantage: The goal isn’t more output. It’s showing up calmer, clearer, and better prepared — so decisions improve.Decision Velocity + Decision Advantage Wins: Make decisions faster and with better information. Speed without clarity is noise. Clarity without speed is stagnation.The Future Belongs to Human + Machine Judgment: Executives who combine instinct with machine intelligence will outperform those relying on either alone. Additional InsightsExecutives Don’t Want More Tools — They Want Their Life Back: Leaders aren’t overwhelmed by lack of tools. They’re overwhelmed by fragmented workflows, constant context switching, and decision fatigue. AI must reduce cognitive load, not add to it.Presence Drives Performance: When AI handles capture and synthesis, leaders show up calmer, more prepared, and more focused. Productivity improves — but performance and clarity are the real unlock.The Identity Threat of AI: Many executives privately fear incompetence. They don’t want to look behind or uninformed. That hesitation often shows up as skepticism or avoidance.Decision Velocity Is the New Differentiator: Artificial organizations move faster because they reduce decision latency. Meetings become focused. Context is pre-loaded. Choices are made with confidence.Traits + Tasks + Tools (T3 Model): Start with how you naturally work best. Then amplify your highest-leverage tasks with the right tools.Capture, Transcribe, Synthesize, Act: A simple workflow that turns every conversation into a reusable data asset. This loop compounds judgment and accelerates learning over time. Episode Highlights00:00 – Episode Recap Barry explains why AI used purely for productivity fails — and why the real advantage comes from transforming how leaders make decisions. 02:58 – Guest Introduction: Sham Colegado Barry welcomes Sham Colegado, a key member of the Artificial Organizations team, who interviews Barry about the book and its core ideas. 03:32 – “Executives Don’t Want More AI Tools” Barry shares the personal burnout moment that sparked a shift from productivity chasing to rethinking how he works. 06:02 – AI’s Real Promise: Presence Over Productivity Why performance and clarity matter more than output — and how AI can make leaders calmer and more focused. 09:30 – The Identity Threat of AI Executives reveal a hidden fear of incompetence and why one-on-one learning environments matter. 12:26 – Decision Velocity & Decision Advantage The two engines of artificial organizations and how reducing decision latency compounds competitive advantage. 15:15 – The Traits, Tasks, Tools Flywheel How aligning natural strengths with high-leverage work determines which AI tools actually create impact. 19:01 – What the Best AI...

    30 min
  2. Unlearning Perfectionism While Building Products That Last with Gerry Khouri

    FEB 4

    Unlearning Perfectionism While Building Products That Last with Gerry Khouri

    What if success isn’t about scaling faster, shipping more, or chasing perfection — but about building something so honest it can last for generations? In this episode, I sit down with Gerry Khouri, Founder & Managing Director of Bufori, one of the world’s longest-running handcrafted automobile companies. For nearly 40 years, Gerry has gone against almost every rule of modern business — choosing craftsmanship over scale, long-term thinking over short-term returns, and integrity over imitation. We explore what Gerry had to unlearn to stay in the game for decades: the myth of perfection, the pressure of shareholder expectations, and the idea that success must look a certain way. This conversation is a masterclass in leadership, product thinking, and building businesses that endure. Key TakeawaysPerfection is a fantasy — luxury is honesty. Products that last are built on integrity, not impossible standards.Success starts with finishing, not selling. The real win is building something real — everything else is a bonus.Craftsmanship scales through capability, not volume. Deep skills create optionality and diversification.The real competition isn’t the market — it’s yourself. Long-term builders focus on self-mastery, not rivals.Great businesses are built by people who challenge you, not agree with you. Additional InsightsGerry built his first car in a garage behind his house — bigger than the house itself — with no external funding.Bufori operates debt-free after nearly 40 years, an extreme outlier in modern manufacturing.The company makes more parts in-house than most car manufacturers, turning necessity into innovation.What started as survival-driven resourcefulness became multiple profit centers through engineering services.Leadership longevity comes from unlearning ego, listening deeply, and leading by example. Episode Highlights00:00 – Episode Recap Gerry Khouri reflects on a pivotal realization: perfection doesn’t build lasting products — honesty, craftsmanship, and long-term thinking do. This mindset reshaped how he built cars, teams, and a business designed to outlive him. 02:15 – Guest Introduction: Gerry Khouri Barry introduces Gerry Khouri, founder of Bufori, a handcrafted automobile company that has spent nearly four decades defying the rules of modern manufacturing. 04:14 – Building the First Car Against All Odds Gerry shares how a backyard hobby, relentless passion, and going against everyone’s advice led him to build his first car from nothing. 07:10 – Redefining What Success Really Means Success wasn’t about money or validation — it was about starting something and finishing it, no matter the odds. 11:54 – Leading Without Resources With no books, no mentors, and no capital, Gerry explains how necessity forced invention and deep mastery of craft. 19:50 – Unlearning Perfectionism in a Luxury Business Why perfection is an illusion, and how focusing on luxury, durability, and intention keeps products moving forward. 23:12 – What Craftsmanship Actually Looks Like Gerry breaks down what it means to truly “make” a product — from designing for repairability to building for generations. 27:29 – Competing With Yourself, Not the Market The most dangerous competitor isn’t another company — it’s complacency and losing the hunger to improve. 31:10 – Unlearning Shareholder-First Thinking Why prioritizing...

    44 min
  3. AI Productivity for Executives: Skyscanner CTO Andrew Phillips

    JAN 21

    AI Productivity for Executives: Skyscanner CTO Andrew Phillips

    From graduate engineer to CTO, Andrew Phillips’ 16-year journey at Skyscanner is a story of continuous reinvention. He didn’t chase titles—he chased growth, deliberately stepping out of his comfort zone and unlearning the habits that no longer served him. What’s kept him at the company for over a decade isn’t status, but challenge: new teams, unfamiliar problems, and the chance to stay close to the work, even as his scope of leadership expanded. In this episode, we explore how Andrew is now applying that same mindset to leading in the AI era—personally and professionally. He shares how he’s built a personal AI stack to stay more present, how Skyscanner is blurring traditional team roles to unlock speed, and why “directed autonomy” is more important than ever. For leaders navigating scale, technology, and the desire to make meaningful impact without burning out, Andrew offers a powerful perspective. Key TakeawaysGrowth through discomfort: Andrew’s biggest accelerations came from switching roles and leaving his comfort zone—not climbing a predefined ladder.AI as a leadership enabler: He uses AI tools to be more present, thoughtful, and effective—especially during high-stakes meetings.From feature factory to outcome focus: Leaders must reconnect people to impact, not just output.Directed autonomy: Empowering teams with AI means giving clear goals—not micromanaging the execution.Unlearning process overreach: Traditional roles, ticketing systems, and rigid handoffs are ripe for reinvention in AI-native organizations. Additional InsightsThe personal AI stack Andrew uses includes ChatGPT, Otter, Cursor, and SpecKit—enabling him to ideate on walks, build apps during board meetings, and maintain strategic presence.Skyscanner’s senior engineers are back coding, using AI to close the gap between architectural thinking and execution.AI-driven productivity unlocks don’t just mean faster work—they mean better work-life balance, deeper engagement, and more human leadership. Episode Highlights00:00 – Episode Recap Andrew Phillips shares how stepping into uncertainty—and building his own AI stack—transformed his leadership at Skyscanner. From personal growth to organizational reinvention, he’s leading the charge on what modern technology leadership looks like. 01:35 – Guest Introduction: Andrew Phillips Barry introduces Andrew Phillips, CTO of Skyscanner, reflecting on their 15-year relationship and Andrew’s rise from graduate engineer to technology leader. 05:45 – The One Trick Pony Moment Andrew recalls the pivotal moment when a CEO challenged him to move teams and stop playing it safe—triggering his real leadership evolution. 12:33 – Starting with Yourself in AI Before transforming your company with AI, Andrew urges leaders to start by experimenting personally and learning from the ground up. 15:15 – Writing Better Prompts, Building Better Specs AI tools thrive on clear direction. Andrew realized that better prompting and crisp product requirements accelerated his results dramatically. 20:01 – Directed Autonomy in the AI Era Giving AI tools (and people) the “why” rather than micromanaging the “how” builds trust, speed, and better outcomes. 24:56 – Parallel Productivity and Boardroom Apps How Andrew built an entire app—during a board meeting—by offloading work to AI and staying fully present in the room. 27:13 – Reclaiming Work-Life Balance AI allows Andrew to unload his mental backlog—using...

    47 min
  4. How Is Visual Intelligence Redefining Human-AI Interaction with Sherry Chang

    JAN 14

    How Is Visual Intelligence Redefining Human-AI Interaction with Sherry Chang

    What if machines could truly see and understand how we move? In this episode, I sit down with Sherry Shang, CEO and co-founder of Neural Lab, a company reimagining how we interact with technology through visual intelligence AI and gesture-based interfaces.  Sherry’s journey from Intel technologist to startup founder began with a pivotal moment during the pandemic. What started as a side project in her living room became Neural Lab—a platform that turns basic webcams into powerful tools for gesture recognition, with no specialized hardware required. Now, Neural Lab is unlocking new ways to deliver care, boost performance, and support human potential. From sterile surgery rooms to personalized rehab and coaching, touchless interaction is creating fresh possibilities for how we live and work with AI. Key TakeawaysComputer vision is gaining eyes: Sherry frames visual intelligence as the “missing sense” in AI—complementing language models with sight.Entrepreneurship is about timing: Sherry waited until her kids were older to build Neural Lab, choosing to innovate on her own terms.Gesture recognition is real—and ready: Neural Lab’s technology translates hand motions into universal commands with no need for specialized hardware.Human-centered design is essential: From recognizing intentional gestures to modeling real-world physicality, their design is inspired by how humans naturally interact.Healthcare leads the way: Use cases like sterile surgical environments are proving to be strong early markets for gesture control. Additional InsightsVisual intelligence is the missing sense in AI: Sherry describes computer vision as adding "eyes" to AI, enabling machines to interpret physical space just as large language models allow them to process language.Entrepreneurship is about timing: Sherry chose to start Neural Lab once her children were older, aligning her professional ambitions with personal priorities.Gesture recognition is real—and ready: Their product works with any basic camera and translates 15 customizable gestures into commands for existing applications—no new hardware required.Designing for human nuance matters: Neural Lab focuses on distinguishing intentional from unintentional gestures using cues like eye gaze and body motion—mimicking how humans communicate.Healthcare is an urgent use case: Environments like surgery rooms benefit immediately from touchless interaction, helping maintain sterility and reduce unnecessary patient radiation.The interface is evolving beyond the mouse: Sherry sees gesture-based interaction as a more natural, immersive input method—moving us beyond traditional tools like keyboards and mice.Customer feedback drives innovation: From live demos to direct use-case discovery, Neural Lab adapts based on what real users need and how they react in context.AI can coach, not just compute: Sherry envisions AI-enabled coaching in sports, physical therapy, and even surgery—delivering expert guidance in real time, at scale. Episode Highlights00:00 – Episode Recap Sherry Chang shares how her journey from Intel technologist to founder of Neural Lab began with a desire to create immersive, meaningful technology—and a pivotal moment during the pandemic when gesture-based interaction suddenly became essential. 02:14 – Guest Introduction: Sherry Chang Barry...

    36 min
  5. Investing In Space with Maureen Haverty

    12/30/2025

    Investing In Space with Maureen Haverty

    Today’s guest is someone I first came across on the Irish People in VC list—and I’m really glad I reached out. Because it turns out Maureen Haverty has one of the most fascinating jobs you can imagine: helping build the future of space. As a Principal at Seraphim Space, the world’s leading space-focused VC firm, she invests globally in technologies pushing the boundaries of what’s possible —and shaping the future of space startup investment. Maureen began her career in nuclear engineering, earning a PhD from the University of Manchester before making the leap into startups. At Apollo Fusion, she survived a hard pivot into space, ultimately becoming COO and steering the company through a $150M acquisition by Astra. That experience—what she calls a startup “baptism by fire”—now informs how she backs early-stage founders as both investor and board director. Her insights have been featured in The Times, and she’ll soon take the stage at Web Summit to speak on “Space as a Strategic Frontier.” Key Takeaways“Build just enough”: Space startups win by testing early and often, not waiting for perfection.Kill fewer dreams: Rigor matters—but so does nurturing half-formed ideas.Get to space ASAP: In-orbit validation creates trust and unlocks massive growth.From Gantt charts to fast loops: High-performing teams test weekly, not quarterly.Customer conversations still matter: Even in space, talking to users beats assumptions. Additional InsightsWhy VC funding in space is shifting toward earlier MVPs.The hidden costs of acquisition for startup culture and speed.How Starship may reshape what's possible—size, cost, and assembly in orbit.The role of government contracts in fostering a competitive space ecosystem. Episode Highlights00:00 – Episode Recap Maureen Haverty shares how balancing rigor with creativity helped her evolve from nuclear engineer to space startup COO to VC. The key? Learning when to test, when to build, and when to let wild ideas breathe. 01:35 – Guest Introduction: Maureen Haverty Barry introduces Maureen Haverty, Principal at Seraphim Space and advocate for grounded rigor in an industry literally aiming for the stars. 03:35 – Learning When Not to Kill Ideas Maureen reflects on being labeled a “dream killer” and how she transformed that mindset to foster innovation with constructive rigor. 07:34 – Applying Rigor Without Stifling Innovation How Apollo used just-enough testing, internal prototyping, and diverse team strengths to build better, faster. 13:54 – Rethinking MVPs in Space Startups Why even space companies now push to generate early revenue and test hardware pre-launch. 18:19 – Customers Want Something They Can See Building a physical, testable product—even a crude one—outperforms pitch decks every time. 20:32 – The $70M Lesson of In-Space Testing How one flight test flipped customer hesitation into a flood of contracts. 26:12 – Surviving the Shift from Prototype to Production The real scaling challenge: maintaining culture and customer trust while redesigning for scale. 30:15 – The Hidden Power of Primes and Policy Why space remains deeply shaped by government buyers—and how that’s changing with new VC-backed players. 35:33 – Starship and the Future of Space Maureen shares what could shift when larger...

    40 min
  6. The Octopus Organization with Jana Werner & Phil Le-Brun

    12/17/2025

    The Octopus Organization with Jana Werner & Phil Le-Brun

    Back when I first worked with Jana Werner at Tesco Bank, I saw firsthand how a crisis could be a crucible for innovation and transformation. Her ability to unlock potential in even the most challenged teams was unforgettable. Now, teaming up with Phil Le-Brun—a transformational leader I came to know through his work at McDonald’s—they’ve co-authored The Octopus Organization, a guide for thriving in an age of continuous transformation. In this episode, we go behind the scenes of their book and explore the anti-patterns that hold organizations back, the behaviors leaders must unlearn, and the mindset shifts required to succeed when change never stops. Whether you’re a CEO, change agent, or team lead, you’ll leave with small, actionable experiments to start evolving your organization—today. Key TakeawaysUnlearning blame-based leadership: Shifting focus from fixing people to fixing systems unlocks performance and trust.Spotting anti-patterns in everyday behavior: Habits like jargon, silos, and avoidance subtly block progress.Embracing uncertainty in leadership: Probabilistic thinking builds better decisions and psychological safety.Driving transformation through small experiments: Distributed action outperforms top-down mandates.Leading with curiosity in the age of AI: Execs must actively engage with tech to stay relevant and credible. Additional InsightsBehind the book: Why The Octopus Organization centers on 36 anti-patterns and how they uncovered themReal-world leadership stories: Lessons from Tesco Bank, McDonald’s, Amazon, and FerrariTransformation fatigue is real: Overengineered change efforts often create fear and resistanceAlignment breakdowns in leadership teams: Many transformations fail because leaders aren't truly on the same pageReframing performance: Asking “what did you stop doing” reveals deeper impact than traditional goals Episode Highlights00:00 – Episode Recap Jana Werner shares how she took over a struggling tech team, discovered their true strengths, and transformed their performance by rebuilding culture and trust. Phil Le-Brun describes the importance of creating a culture of trust in organizations, allowing people to test ideas and make a real difference. 02:46 – Guest Introduction: Jana Werner & Phil Le-Brun Barry O'Reilly introduces guests Jana Werner and Phil Le-Brun, describing their collaboration during times of crisis at Tesco Bank, their leadership backgrounds, and their shared vision for adaptive, purpose-driven organizations as captured in their new book. 04:36 – Revitalizing a Demotivated Team at Tesco Bank Jana Werner narrates how she took over a demotivated technology team, overcame her initial preconceptions, and transformed the group into a top-performing unit by changing culture, empowering individuals, and shifting organizational dynamics. 07:07 – Lessons from McDonald's: Balancing Centralization and Agility Phil Le-Brun explains McDonald's transformation journey, the need to unify local and corporate efforts, and the financial impact of building trust and alignment. 10:16 – Learning from Industry Leaders Phil recounts interviews with CEOs like Indra Nooyi and Benedetto Vigna, highlighting that true leadership requires humility, storytelling, and ongoing curiosity. 14:14 – Unlearning the Need for Certainty Jana Werner discusses shifting away from needing all the answers and embracing uncertainty, drawing on insights from Annie Duke and other...

    37 min
  7. What Truly Decisive, Agentic Organizations Are Doing? – Steve Elliott

    12/03/2025

    What Truly Decisive, Agentic Organizations Are Doing? – Steve Elliott

    In this episode of The Unlearn Podcast, Barry O’Reilly is joined by Steve Elliott, a serial entrepreneur, product leader, and investor with two decades of experience advising high-growth companies. Steve is the founder of Dotwork, an AI-driven platform that connects strategy to execution, and co-founder of The Uncertainty Project, a community for product leaders focused on better decision-making. He previously served as Head of Product at Atlassian, where he helped scale Jira Align after selling his company AgileCraft for $166M—earning recognition as a Fortune Best Small Business in America and a finalist for the Ernst & Young Entrepreneur of the Year. With five successful exits under his belt, Steve brings rare depth to the art of building and unbuilding what no longer serves. In this conversation, Barry and Steve explore how to design for the messy reality of modern work, the role of unlearning in leadership, and how AI is redefining what it means to be a decisive company. Key TakeawaysFrom CTO to CEO – Why Steve transitioned from tech leader to founder and the personal growth that came with it.Scaling after acquisition – The emotional and strategic shifts required when your startup becomes part of a larger machine.Why strategy execution breaks – Most alignment tools assume order—Steve builds for complexity.Agentic AI in the enterprise – How Dotwork uses knowledge graphs and AI to surface insight in context, not just dashboards.Decisive companies – What it really means to help leaders make faster, more confident decisions. Additional InsightsUnlearning the idea that startups are for the young—Steve didn’t found his first company until his 40s.How Dotwork is building a “context memory engine” for both executives and AI agents.The future of AI-native tools isn’t more interfaces—it’s less friction and smarter context delivery.Why the most valuable enterprise products aren’t flashy—they’re quiet, ambient, and deeply integrated. Episode Highlights00:00 – Episode 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...

    47 min
  8. The Human Side of AI: How HR Can Lead the Transformation with Cass Pratt

    11/19/2025

    The Human Side of AI: How HR Can Lead the Transformation with Cass Pratt

    In this episode of the Unlearn Podcast, I sit down with Cass Pratt, Chief Human Resources Officer at Progyny, to explore how HR is evolving into a design discipline that blends human connection with AI-powered productivity. From building bots to boost employee experience to reshaping how we think about roles in an automated world, Cass shares an honest look at how she’s bringing people along on a transformation journey—with curiosity, experimentation, and heart. We discuss her pivotal decision to say yes to opportunities beyond her comfort zone, the strategic shifts she's leading inside a fast-scaling company, and why the future of HR is about enhancing humanity, not replacing it. If you’re wondering what leadership looks like when AI meets empathy, this one’s for you. Key TakeawaysUnlearning expertise-dependence: Cass shifted from relying on experts to co-creating solutions with AI tools before engaging others.AI as a force for elevation: At Progyny, AI is used to give employees time back, not take roles away—enabling deeper focus on human-centric work.Low-code leadership: Cass, a self-described non-technical leader, built HR bots and reimagined policies through practical AI applications.Scaling culture through consistency: AI chatbots improved response times, standardized answers, and gave insight into employee concerns.Embedding experimentation: Teams are encouraged to ask, "What should I stop doing?"—sparking a culture of reinvention and initiative. Additional InsightsProgyny’s “Super Fans” initiative reframes AI gains as an opportunity to deepen customer and employee relationships.Training is done in cohorts to build shared understanding and reduce AI anxiety.Cross-functional collaboration with junior team members—like the intern who built the HR bot—shows how innovation can come from any level.Cass uses AI to simplify and globalize complex frameworks like competency models, improving alignment across teams and geographies. Episode Highlights00:00 – Episode Recap Cassandra Pratt shares how embracing discomfort led her to leap into healthcare, build a transformative HR function, and lead with AI—not to eliminate roles, but to elevate people and amplify their impact. 02:37 – Guest Introduction: Cassandra Pratt Barry introduces Cass Pratt, Chief People Officer at Progyny, a fertility and family-building benefits company scaling rapidly with a human-first, tech-empowered culture. 04:48 – Saying Yes to Growth Cass reflects on a missed opportunity that taught her the cost of saying no—and set her on a path to jump into unknowns with conviction. 08:04 – Startup Lessons and Leadership Growth From 50 to 850 employees, Cass shares what it means to grow with a company and embrace mistakes as part of the journey. 11:00 – Diving into AI Without a Tech Background Despite lacking technical skills, Cass threw herself into generative AI—learning by doing and discovering intuitive ways to drive value. 13:10 – Unlearning the Expert Reflex Cass rethinks her default of turning to experts first—instead starting with AI to shape stronger ideas and bring others in as collaborators. 15:13 – Redesigning Processes, Not Just Tools AI opened up opportunities to rethink workflows from scratch, not just automate existing inefficiencies. 20:35 – Making AI Safe and Human Cass shares how transparent messaging, training, and cultural reinforcement helps ease AI anxieties and keep

    46 min

About

The way to think differently is to act differently and get comfortable with being uncomfortable. For business leaders, entrepreneurs, managers and anyone who wants to improve how they work and live: Welcome to the Unlearn Podcast. Host Barry O’Reilly, author of Unlearn and Lean Enterprise seeks to synthesize the superpowers of extraordinary individuals into actionable strategies you can use—to Think BIG, start small and learn fast, and find your edge with excellence.