Unlearn

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 RecapGerry 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 KhouriBarry 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 OddsGerry 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 MeansSuccess wasn’t about money or validation — it was about starting something and finishing it, no matter the odds.11:54 – Leading Without ResourcesWith 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 BusinessWhy perfection is an illusion, and how focusing on luxury, durability, and intention keeps products moving forward.23:12 – What Craftsmanship Actually Looks LikeGerry 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 MarketThe most dangerous competitor isn’t another company — it’s complacency and losing the hunger to improve.31:10 – Unlearning Shareholder-First ThinkingWhy prioritizing short-term financial returns can destroy long-term craftsmanship and culture.35:07 – Turning Internal Capabilities Into New BusinessesHow Bufori transformed hard-earned internal skills into diversified engineering services.38:10 – Advice for Founders Scaling Passion ProjectsDream big, be honest with yourself, ignore the noise — and don’t fear hard work or criticism.42:54 – Building Teams That Challenge YouWhy great leaders surround themselves with people who tell them what they need to hear, not what they want to hear.FAQsWhat does it mean to unlearn perfectionism in product building?Unlearning perfectionism means letting go of the belief that products must be flawless before they can be shipped. In this episode, Gerry Khouri explains why progress, honesty, and durability matter more than chasing an impossible standard of perfection.How do you build products that last for decades?Gerry shares that long-lasting products are built through craftsmanship, attention to detail, and designing for repairability and longevity — not speed, shortcuts, or mass production.Who is Gerry Khouri and why is he notable?Gerry Khouri is the founder of Bufori, a handcrafted automobile company that has operated for nearly 40 years. He’s known for building bespoke luxury cars by hand and for leading a debt-free business focused on long-term value.Is perfectionism bad for startups and founders?Perfectionism can become a liability when it slows decision-making, delays launches, or prevents learning. Gerry explains how redefining excellence allowed him to keep building while maintaining extremely high standards.What does long-term thinking in business actually look like?Long-term thinking means designing products, teams, and systems to endure — focusing on durability, skills, culture, and customer trust rather than quarterly results or fast exits.Useful ResourcesGerry Khouri on LinkedIn - https://www.linkedin.com/in/gerry-khouri-08507788/ Bufori Motor Cars Website - https://bufori.com/ Follow the HostBarry O’ReillyLinkedIn: https://www.linkedin.com/in/barryoreillyWebsite: https://barryoreilly.comTwitter (X): https://x.com/barryoreillyInstagram: https://www.instagram.com/barryoreilly/Facebook: https://www.facebook.com/barryoreillyauthor/

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 RecapAndrew 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 PhillipsBarry 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 MomentAndrew 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 AIBefore 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 SpecsAI 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 EraGiving AI tools (and people) the “why” rather than micromanaging the “how” builds trust, speed, and better outcomes.24:56 – Parallel Productivity and Boardroom AppsHow 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 BalanceAI allows Andrew to unload his mental backlog—using voice notes and assistants so he can be more present at home.31:21 – Avoiding the AI Cost TrapNot every solution needs an LLM. Andrew shares how Skyscanner balances innovation with cost and pragmatism.36:58 – Blurring the Lines Between RolesDesigners writing code, engineers making design tweaks—Andrew explains why role flexibility is a hallmark of high-performing, AI-native teams.42:32 – Unlearning the Process FetishIt’s time to rethink JIRA tickets, handoffs, and audits. In a machine-collaborative world, many processes should be automated or eliminated.43:36 – The CTO’s Excitement for the Next QuarterAndrew sees a future where everyone—from architects to senior ICs—is back building again, connected to outcomes, not just output.46:36 – Closing ReflectionsLeadership is about presence, purpose, and people. Andrew shares his optimism for what’s possible when teams are empowered to ship and grow.FAQsQ1. How is Skyscanner using AI internally?Teams are using tools like Cursor, ChatGPT, and SpecKit to prototype faster, write code, and automate workflows—blurring traditional role boundaries.Q2. What is “directed autonomy” and why does it matter?Directed autonomy means giving teams (and AI) clear goals and guardrails while allowing freedom in how outcomes are achieved. It increases speed, trust, and creativity.Q3. What does Andrew mean by “blurring the lines between roles”?At Skyscanner, designers are fixing front-end issues, engineers are influencing product direction, and architects are coding again—enabled by AI tools that lower technical barriers.Q4. What AI tools does Andrew personally use?Andrew’s AI stack includes ChatGPT, Cursor, SpecKit, and Otter—used for building apps, drafting comms, and capturing ideas while on the move.Q5. How does AI help leaders stay present?By offloading execution to AI (like building apps during meetings or drafting emails from voice notes), leaders can stay focused in key moments and reduce context switching.Useful ResourcesSkyscannerCursor – AI pair programming toolOtter.ai – Voice transcription and meeting notesBarry O’Reilly’s AI Executive CoachingFollow the HostLinkedInPersonal siteFacebookX (Twitter)Instagram

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 RecapSherry 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 ChangBarry introduces Sherry Chang, CEO of Neural Lab, former Intel leader, and innovator in computer vision and immersive interaction.06:27 – Starting Up During the PandemicSherry shares how the idea for Neural Lab came to life in her living room, driven by a vision for safer, touchless human-computer interaction.09:30 – From Prototype to Minority ReportBarry recalls early demos that felt like science fiction—using just a webcam to control computers with hand gestures.12:00 – Designing for IntentionalitySherry explains the challenge of recognizing intentional vs. accidental gestures—and how eye-gaze and motion patterns help filter noise.14:57 – Gesture as Input DeviceThey discuss how gestures open new interaction possibilities—from whiteboards to evaluating athletic movements.18:26 – Finding Product-Market Fit in HealthcareSherry shares insights from radiology conferences—surgeons see immediate value in touchless interfaces for sterile environments.22:21 – Reimagining Clinical WorkflowsGesture-based interaction eliminates the need for voice commands or assistants in the OR—streamlining workflow and reducing risks.25:35 – The Bigger PictureBarry reflects on the paradigm shift—freeing people from fixed tools like keyboards to interact with tech naturally.28:56 – Unlocking Human Potential with AI CoachingSherry envisions AI coaches for physical therapy, sports, even surgery—democratizing access to expert feedback and improving outcomes.33:11 – The AI Augmentation MindsetRather than replacing jobs, gesture-based AI enhances human performance and creativity, enabling new ways of working.35:21 – Closing ReflectionsBarry highlights the promise of technologies like Neural Lab—empowering people to interact more intuitively with machines and unlock new capabilities.FAQsQ1. What is gesture recognition technology?Gesture recognition uses computer vision to detect and interpret human body movements—like hand gestures—as input commands to control software or devices.Q2. How does Neural Lab's gesture control work?Neural Lab’s system uses any standard camera to detect 15 configurable gestures, translating them into commands compatible with most applications—no special hardware needed.Q3. Is gesture recognition practical in healthcare?Yes. Surgeons can use gestures to manipulate images mid-procedure without breaking sterility, improving workflow and reducing radiation exposure.Q4. Can gesture-based AI help in physical therapy?Absolutely. It enables real-time coaching, posture correction, and progress tracking for rehab patients—making at-home therapy more effective.Q5. How is AI augmenting human potential with this tech?By combining visual intelligence with feedback loops, gesture-based AI allows for elite-level coaching and real-time assistance in fields like sports, surgery, and workplace ergonomics.Useful ResourcesNeural Lab Official Site - https://neural-lab.com/Connect with Sherry on LinkedIn - https://www.linkedin.com/in/sherryschang/

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 RecapMaureen 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 HavertyBarry 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 IdeasMaureen 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 InnovationHow Apollo used just-enough testing, internal prototyping, and diverse team strengths to build better, faster.13:54 – Rethinking MVPs in Space StartupsWhy even space companies now push to generate early revenue and test hardware pre-launch.18:19 – Customers Want Something They Can SeeBuilding a physical, testable product—even a crude one—outperforms pitch decks every time.20:32 – The $70M Lesson of In-Space TestingHow one flight test flipped customer hesitation into a flood of contracts.26:12 – Surviving the Shift from Prototype to ProductionThe real scaling challenge: maintaining culture and customer trust while redesigning for scale.30:15 – The Hidden Power of Primes and PolicyWhy space remains deeply shaped by government buyers—and how that’s changing with new VC-backed players.35:33 – Starship and the Future of SpaceMaureen shares what could shift when larger payloads, faster launch cadences, and orbital assembly become possible.39:25 – Closing ReflectionsSpace is finally catching up to the urgency of its people. In an industry where “yesterday” is always the best time to start, speed is the differentiator.FAQsWhat is Maureen Haverty known for?Maureen Haverty is a Principal at Seraphim Space, the world’s leading venture capital firm focused on space technology. She’s also known for her leadership at Apollo Fusion, where she helped scale the company to a $150M acquisition by Astra.What does Seraphim Space invest in?Seraphim Space invests in early-stage space technology startups globally, backing innovations in satellites, launch systems, in-orbit services, and deep tech infrastructure critical to the future of space exploration.What did Maureen Haverty learn from her time at Apollo Fusion?Maureen learned the importance of balancing rigor with experimentation. Her experience taught her to support bold ideas without stifling them and to build “just enough” before validating with customers—especially critical in high-stakes industries like space hardware.How do space startups approach product testing and market validation?Unlike SaaS startups, space companies face high costs and long timelines. The most successful ones focus on testing early and often, getting hardware into orbit quickly, and talking to customers well before finalizing product designs.Why is in-space testing so important for space companies?Even with rigorous ground-based testing standards, nothing builds customer confidence like real in-orbit validation. Maureen shares how one space test led to $70M in contracts within weeks—proving that live demonstrations are a major unlock for credibility and growth.What trends are shaping the future of the space industry?Maureen highlights the shift toward faster iteration, more venture-backed growth (vs. acquisition), and the game-changing potential of SpaceX’s Starship, which could enable larger structures, faster launch cycles, and more ambitious projects in orbit.Useful ResourcesMaureen Haverty on LinkedInSeraphim SpaceFollow the HostLinkedInPersonal SiteFacebookX (Twitter)Instagram

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 goalsEpisode Highlights00:00 – Episode RecapJana 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-BrunBarry 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 BankJana 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 AgilityPhil 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 LeadersPhil 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 CertaintyJana Werner discusses shifting away from needing all the answers and embracing uncertainty, drawing on insights from Annie Duke and other leaders.21:30 – Small Changes, Big ImpactJana introduces the book's structure around "anti-patterns" and advocates for making small, distributed changes rather than massive, top-down transformations.26:29 – Leadership Alignment: Avoiding Transformation PitfallsPhil highlights the need for alignment among leadership teams and points out common failures in transformation projects due to lack of shared understanding.29:09 – Becoming "Technology Teenagers"Phil and Jana emphasize the importance of leaders learning to experiment and engage directly with new technologies, encouraging curiosity and hands-on learning with AI.32:12 – Start Small and ExperimentBoth authors encourage listeners to pick a tip from the book and try it right away—emphasizing the value of experimentation, feedback, and removing old practices to spark growth.Useful ResourcesJana Werner on LinkedIn - https://www.linkedin.com/in/janawerner1/ Phil Le-Brun on LinkedIn - https://www.linkedin.com/in/phillebrun/ The Octopus Organization – Book by Jana Werner & Phil Le-Brun - https://www.amazon.com/Octopus-Organization-Thriving-Continuous-Transformation-ebook/dp/B0DRZ2MXBR Related episode: Accelerating Transformation in Crisis – Tesco Bank Case Study - https://barryoreilly.com/explore/articles/accelerating-transformation/ Amy Edmondson – Research on Psychological Safety - https://amycedmondson.com/psychological-safety/ Annie Duke – Thinking in Bets - https://www.annieduke.com/books/ Indra Nooyi – Leadership Insights - https://www.indranooyi.com/ Follow the HostLinkedIn: Barry O’ReillyWebsite: barryoreilly.comTwitter/X: @barryoreillyInstagram: @barryoreillyFacebook: Barry O’Reilly

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 RecapSteve 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 ElliottBarry 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 shiftsFrom a consulting career at PwC to software experiments that took off—how Steve found his way into entrepreneurship.08:55 – From technologist to founderThe 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 decisionsWhy enterprise tools fail to support real-time, strategic decisions—and how Steve is tackling the problem differently.17:50 – The rise of agentic frameworksHow Dotwork is using knowledge graphs and agentic AI to reflect the dynamic, decentralized nature of modern organizations.23:31 – Breaking through transformation fatigueHow Dotwork builds trust not through marketing, but by showing real, contextual results fast.26:23 – Beyond dashboards: AI-native UXWhy 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 AIBarry shares his experience coaching executives on AI—and why hands-on experimentation is the only path to mastery.36:07 – Context engines for agentsSteve explains how Dotwork unintentionally became a context memory platform—crucial for the future of autonomous agents.40:36 – Magic moments in enterprise UXWhen engineering hasn’t seen the reports their software generates—because the platform is that intuitive.43:17 – Closing ReflectionsSteve 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.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 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.Useful ResourcesProgyny: https://www.progyny.comConnect with Cassandra Pratt: LinkedInAI Executive Coaching by Barry: https://barryoreilly.comFollow the HostLinkedIn: linkedin.com/in/barryoreillyWebsite: barryoreilly.comFacebook: facebook.com/barryoreillyauthorTwitter/X: x.com/barryoreillyInstagram: instagram.com/barryoreilly

Phil Gilbert, former General Manager of Design at IBM and author of Irresistible Change, shares his groundbreaking insights on business transformation. He emphasizes that real change starts with culture, not just tools. Discussing his three-part model of people, practices, and places, he outlines how to ignite transformation within organizations. Phil also explores the crucial role of teams in adopting AI and the importance of designing leadership structures that foster trust. His experiences and practical frameworks provide a compelling blueprint for leaders aiming to create lasting impact.

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.Key TakeawaysClarity 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.Additional InsightsPositioning 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.Episode Highlights00:00 – Episode RecapAnthony 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 PierriBarry 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 EverythingWhy 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 AdvantageAnthony 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 PositioningDon’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 PositioningAs 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 YourselfPositioning isn’t self-promotion—it’s about telling a compelling story that reflects your champion’s reality.35:15 – The “Tell Me More” EffectGreat 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 AssetThe 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 ScaleAnthony 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 ConvertsBarry and Anthony unpack how to use messaging anchors, problem framing, and customer-centric storytelling to guide your homepage narrative.Useful ResourcesFletchPMM WebsiteAnthony Pierri on LinkedInApril Dunford – Obviously AwesomeWynter – Message TestingFollow the HostLinkedInOutlier Venture PartnersFacebookTwitter/XInstagram

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.Key TakeawaysLoneliness Is a Biological Threat: Your brain interprets social disconnection like hunger or pain—not just a mood, but a warning signal.Small In-Person Moments Matter: Even brief, face-to-face interactions boost mood and cognitive function more than digital ones.Isolation Damages the Brain: Chronic loneliness raises cortisol, shrinks memory centers, and can shorten your lifespan.Introverts Still Need People: Social time benefits everyone—introverts just hit their saturation point sooner.Generosity Is Hardwired: From rats to dolphins, the impulse to connect and give is deeply embedded in our biology.Connection Requires Unlearning: Independence and solitude aren't always virtues—sometimes they’re survival myths in disguise.Additional InsightsSocial prediction systems in the brain were scrambled by COVID—and many people still haven’t recalibrated.Most people think they’re worse-than-average at socializing, which fuels avoidance and false self-judgment.Digital tools remove the social cues—tone, expression, touch—that our brains need to feel emotionally nourished.Empathy is not automatic—it’s biased and trainable, shaped by exposure to difference and intention.Rebuilding community isn’t just good for you—it’s essential for physical, mental, and societal health.Episode Highlights00:00 – Episode RecapBen 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 ReinBarry 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 PredictionsBen 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 LonelinessBen 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 FriendsBarry 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 FearBen 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 ConnectionBarry 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 MattersBen 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 NatureBen shares surprising studies showing kindness and empathy across the animal kingdom—and what humans can learn from them.39:22 – Closing ReflectionsBarry and Ben wrap with a call to action: prioritize connection, embrace kindness, and use what we know to better ourselves and others.Useful ResourcesWhy Brains Need Friends by Dr. Ben ReinDr. Ben Rein on LinkedInBen’s popular science content on Instagram and TikTokFollow the HostLinkedInPersonal SiteFacebookTwitterInstagram