Barry O'Reilly

Unlearn

#149 in Entrepreneurship · 🇩🇰 #158 in Entrepreneurship · 🇮🇹

About the show

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.

Newest episodes

How Leaders Turn AI Investment Into Better Business Outcomes with Melanie Steinbach

Nov 11, 2026 36 min

AI investment can give people new tools without changing the way the business performs. Leaders need to explain what should improve, help teams develop new ways of working, and ensure their goals and incentives support that change. In this episode, Melanie Steinbach, whose people leadership experience spans McDonald’s, Cameo, and MasterClass, joins me to explore how organizations turn AI investment into better business outcomes. Mel explains why benefits take time to emerge, why training needs ongoing practice, and how individual KPIs can undermine shared goals. We also discuss leaders’ responsibility for redesigning work across departments and how recognition can encourage people to share what they learn. This is the third podcast in The Adaptive Enterprise, our five-part article and podcast series on redesigning work, governance, and leadership for the age of AI. Key TakeawaysConnect the purpose to the person: Explain why the organization is investing in AI, what it expects to achieve, and what employees need to do differently. Melanie’s example of changing a promotion model shows why both organizational context and individual expectations matter.Measure progress along the way: Capability development and business benefits may emerge on different timelines. Identify meaningful milestones, such as stronger analysis or better cross-functional collaboration, and explain how they contribute to the intended outcome.Treat training as the beginning: A workshop or certification does not establish lasting behavior change. Repeated practice, feedback, and opportunities to apply learning help people develop capability in everyday work.Make work redesign a leadership responsibility: Individual productivity improvements do not automatically improve the whole business. Leaders need to define shared outcomes, remove obstacles, and support teams in changing work across departmental boundaries.Align KPIs with the change you want: Goals and incentives shape what people prioritize. M...

The Leadership Behaviors to Best Govern AI with Cassandra Pratt and John Marcante

Oct 28, 2026 39 min

AI capabilities are advancing quickly, but changing how people work takes time. Leaders need to give teams the confidence to experiment while protecting sensitive information and keeping responsibility clear. How they manage that balance shapes whether AI leads to better business outcomes. In this episode, Cassandra Pratt, CHRO at Progyny, and John Marcante, former Global CIO of Vanguard, join me to explore how governance can support that change. Cass shares lessons from Progyny’s internal HR tool, Lumi, and efforts to redesign workflows while building employee trust. John recalls how a Vanguard team improved website conversion by listening to clients and simplifying their choices. He connects that experience to governing AI through clear business outcomes, accountability, and oversight matched to risk. This is the second podcast in The Adaptive Enterprise, our five-part article and podcast series on redesigning work, governance, and leadership for the age of AI. Key TakeawaysStart with a business outcome: Define the problem you want to solve before choosing how to use AI. John’s Vanguard example shows how customer research and simpler choices helped address a conversion problem that previous technology investment had not resolved.Design governance into the whole workflow: Bring the relevant business, risk, and technical partners together early. Cass explains why understanding the data and the full process makes it easier to establish appropriate controls.Build trust through visible action: Explain how information is handled and show what happens when work is automated. Cass describes employees moving into a new member services area after automation, giving them evidence that leadership would follow through on its commitments.Put recovered capacity toward what matters: At Progyny, reducing manual work can give people more time to listen to and support members. Judge progress against the business outcome and the experience you want to improve.Match oversight to the r...

Why AI Adoption Is No Longer Enough to Create Business Value with John Marcante

Oct 14, 2026 33 min

Making technology faster does not automatically make the business better. John Marcante spent 28 years at Vanguard, including serving as Global CIO and leading its high-net-worth and advice business. As Deloitte’s U.S. CIO-in-Residence, he works with senior technology leaders navigating change. In our conversation, John and I explore why AI investment needs to change how work gets done. John shares what happened when Vanguard’s cloud journey made IT faster than the business could absorb, and how shifting to cross-functional teams and shared outcomes helped address that gap. We also discuss human judgment, the anxiety people feel when familiar tasks are automated, and how leaders can direct freed-up time toward work that matters. This is the first podcast in The Adaptive Enterprise, our five-part article and podcast series on redesigning work, governance, and leadership for the age of AI. Key TakeawaysRedesign work around new capabilities: Speeding up one step in a process can leave the overall business unchanged. Leaders need to bring people together to rethink the work from end to end.Align teams around a business outcome: At Vanguard, engineers and business colleagues needed a shared definition of success. Measuring each function separately made it harder to improve the result for clients.Decide how recovered capacity will be used: Time saved through automation creates an opportunity. Leaders are responsible for helping people use that time where judgment and expertise can improve outcomes.Help people redefine their value: As portfolio activities became automated, Vanguard advisors could spend more time helping families navigate important life decisions. John describes how client loyalty became the goal guiding that shift.Build a continuous cycle of adaptation: The Adaptive Enterprise Loop connects emerging capabilities, work redesign, outcome measurement and governance, and learning. Organizations need to repeat this cycle as new possibilities emerge. Additional...

Similar podcasts

The Prof G Pod with Scott Galloway Vox Media Podcast Network

Aspire with Emma Grede Emma Grede | Audacy

SaaS Købmænd - Iværksætteri, Tech & Startups Bo Møller og Anders Eiler

Iværksætterdrømme Alexander Stricker

The Tim Ferriss Show Tim Ferriss: Bestselling Author, Human Guinea Pig

My First Million Hubspot Media

声动早咖啡声动活泼

Beyond The Prompt - How to use AI in your company Jeremy Utley & Henrik Werdelin

All episodes

How Leaders Turn AI Investment Into Better Business Outcomes with Melanie Steinbach

Nov 11, 2026 36 min

The Leadership Behaviors to Best Govern AI with Cassandra Pratt and John Marcante

Oct 28, 2026 39 min

Why AI Adoption Is No Longer Enough to Create Business Value with John Marcante

Oct 14, 2026 33 min

When AI Makes Development Faster, What Should You Build with Ciaran Cosgrave

Sep 30, 2026 41 min

When building gets easier, choosing what to build becomes even more important. Ciaran Cosgrave is CEO of Nearform, a global AI-native engineering company for the enterprise. Before moving into entrepreneurship and technology, he spent the first decade of his career running refugee camps across Africa and Central America. Those experiences shaped how he thinks about resilience, problem-solving, and building teams. In our conversation, we explore why Ciaran focuses on problems before technology, how AI software development is compressing months of prototyping into days and weeks, and why faster experimentation makes judgment even more important. We also get into the new challenge leaders face when teams can generate more ideas and prototypes than organizations can realistically absorb. Key TakeawaysStart with the problem, not the technology: Understanding the underlying problem and speaking with the people experiencing it creates a stronger foundation than chasing technology or quick financial returns.Knowing what to build remains difficult: AI can change how software gets built, but leaders still need judgment to determine which problems matter and what is worth creating.Faster prototypes can improve judgment: Moving from idea to prototype in days or weeks gives teams more opportunities to explore alternatives and test assumptions before committing to large investments.More experimentation requires better filtering: As testing ideas becomes faster and cheaper, leaders need mechanisms for deciding which prototypes deserve to move forward.Growth is becoming less dependent on headcount: AI is challenging the traditional services model where growing a business was closely tied to adding more people. Additional InsightsResilience can come from unexpected experiences: Ciaran credits his years working in refugee camps with teaching him perseverance and giving him perspective when facing rejection and uncertainty.Great teams still matter: Ciaran emphasizes finding good peopl...

From SaaS Scale to AI Startups: What We Had to Unlearn to Build Again with Sam Kroonenburg

Sep 16, 2026 42 min

Building AI startups can make past success a liability when it convinces you that the way you built before is the way you should build next. Sam Kroonenburg knows what it feels like to build at scale. He co-founded A Cloud Guru, helped grow it into a business serving millions of learners, and eventually sold the company to Pluralsight. Now, as CEO and co-founder of Cuttable, he’s back at the beginning: finding customers, testing assumptions, shipping imperfect products, and learning how different company-building looks in the AI era. In our conversation, we explore what Sam had to unlearn when he moved from running a 600-person company back into an early-stage startup. We get into why Cuttable walked away from nearly $1 million in annual recurring revenue, how enterprise customers can pull a young company away from the product it actually needs to build, and why AI is shifting product and engineering teams from owning parts of a system to owning measurable outcomes. Key TakeawaysPast success can distort your judgment: Starting Cuttable reminded Sam that reputation means little if the product does not solve a problem customers will pay for.Experience does not transfer automatically: Sam could trust his instincts when building for engineers, but entering advertising required him to test assumptions and learn from customers.Revenue can hide the wrong product: Cuttable reached nearly $1 million in ARR while engineers were still manually doing work the product was supposed to automate.Taking the long view can require a reset: Sam and his co-founders released every customer, returned to zero revenue, and rebuilt around end-to-end automation.AI shifts the focus from tasks to outcomes: Instead of teaching AI to copy a human process, teams should define the desired result and let AI determine how to achieve it. Additional InsightsSpeed can be an advantage over scale: A Cloud Guru prepared courses before AWS certifications launched, then updated them using real exam feedback....

Building Better Products Through Better Product Operations with Denise Tilles

Sep 2, 2026 42 min

AI can accelerate a strong operating model, but when decision rights, incentives, or data are already unclear, it can make the mess spread faster. In this episode, I sit down with Denise Tilles, a leading voice in product operations, to unpack how her career moved from editorial work at Condé Nast into product management, commercial leadership, and eventually product operations. Denise shares how learning to work with revenue data, product analysts, and operating models changed the way she thought about product leadership and led to her work helping enterprise organizations make faster, better-quality decisions. We explore what product operations actually does, why an operating model needs to define how decisions get made, and where incentives can quietly undermine even a well-designed process. We also dig into what happens when AI makes producing documents, specifications, and analysis nearly effortless: generating more output doesn't remove the work of judgment. In many cases, it makes clarity about inputs, outputs, ownership, and what “good” looks like even more important. Key TakeawaysProduct ops should improve decision-making: Denise defines it around business and data insights, customer and market insights, and the operating model.Commercial context changes product thinking: At Cision, learning P&L, ACV, and recognized revenue helped Denise connect product decisions directly to business outcomes.Good analysis reveals hidden opportunities: A product analyst uncovered an add-on opportunity that generated roughly $1 million within a year.Operating models need clear decision rights: Teams need to know what gets worked on, who decides, and how work actually gets done.AI amplifies the system already in place: If ownership, data, or processes are unclear, AI can make those weaknesses spread faster. Additional InsightsInformal decisions can override formal processes: Denise learned that hallway conversations and executive requests often mattered more than the document...

Redesigning Leadership for the Age of AI Agents with Tatyana Mamut

Aug 19, 2026 46 min

AI is forcing us to rethink a question most organizations have avoided for years: what is uniquely valuable about human work when intelligence itself is no longer scarce? Tatyana Mamut, CEO of Wayfound and former CPO of Nextdoor, joins me to explore AI adoption through a lens that goes beyond software. Drawing on her background in anthropology, economics, organizational design, and product leadership, Tatyana explains why the real challenge is designing the rules, tools, norms, incentives, and relationships that shape how humans and AI agents work together. We get practical about what this means at both an individual and organizational level. We explore the human capabilities that become more valuable as AI takes on more routine mental work, why fear leads companies into bad AI decisions, how poorly designed incentives can push agents toward unexpected behavior, and why the subject-matter experts closest to the work need to become responsible for managing the agents operating alongside them. Key TakeawaysHuman comparative advantage is changing: As AI takes on more mental work, people need to rethink where their uniquely human value comes from.Develop taste, judgment, relationships, and performance: Tatyana sees these as practical areas where people can complement AI rather than compete with it.AI adoption is an organizational design problem: Success depends on redesigning rules, tools, norms, incentives, and accountability around the technology.Goals and guardrails can still produce the wrong behavior: An agent may follow its objective while still acting against the organization’s intent, as Tatyana’s refund example shows.Subject-matter experts need to become agent managers: The people closest to the work must be able to monitor, correct, and improve the agents operating in their domain. Additional InsightsOrganizational culture can be consciously designed: Tatyana frames culture as the interaction of rules, tools, and unwritten norms that shape behavior.Relationshi...

Exclusive Audiobook Preview for Artificial Organizations

Jul 22, 2026 45 min

Before leaders can redesign their organizations with AI, they have to reconsider how they personally think, work, and make decisions. In this special episode of Unlearn, Barry O’Reilly shares the opening chapter of the audiobook edition of Artificial Organizations, narrated in his own voice. After hearing from readers who wanted another way to experience the book, Barry spent four days in the studio bringing its ideas and stories to life. The process was rewarding, demanding, and personal. As someone who is dyslexic, reading every word aloud required a different kind of focus from delivering a keynote, teaching a workshop, or hosting a podcast conversation. Barry then takes listeners into the central argument of the book: organizations often begin AI adoption with licenses, pilots, and tools while leaving leadership behavior and decision-making systems unchanged. Drawing from his own experiments, leadership research, and work with senior teams across North America, Europe, and Asia, he explains why meaningful AI transformation starts with human traits, high-value tasks, and the judgment leaders must preserve before selecting technology. Key TakeawaysAI should strengthen judgment, not simply increase output: Machines can process and synthesize information at a scale no individual can match, but leaders still have to decide what matters. The opportunity is to use AI to prepare, capture, and pressure-test thinking so human attention stays focused on consequential decisions.Start with traits, then tasks, then tools: Barry’s 3T model begins with how a leader naturally thinks, creates, communicates, and decides. Only after identifying the tasks where that judgment creates the most value should leaders choose tools to support the work.Decision velocity must be paired with decision advantage: Decision velocity is how quickly a leader moves from question to insight, decision, and action. Decision advantage is the quality and depth of context behind that choice; speed without...

Why AI Makes Great Systems Matter Even More with Eric Baxley

Jul 8, 2026 36 min

AI is making it easier than ever to build products, automate work, and scale ideas. The challenge is no longer access to technology. It's designing the systems, stories, and customer understanding that turn AI into real business outcomes. In this episode of Unlearn, I'm joined by Eric Baxley, Chief Marketing Officer at Nobody Studios. Eric shares how a seventh-grade summer teaching himself to program on an Atari 800 sparked a 30-plus year career spanning software development, product management, marketing, sales, business development, and partnerships. We explore what Eric has had to unlearn while building companies in the AI era—from challenging assumptions before execution and replacing corporate polish with authentic storytelling, to designing scalable systems instead of disconnected tools. Along the way, Eric explains why great marketing still starts with deeply understanding customers, and why AI works best when it amplifies human judgment rather than replacing it. Key TakeawaysChallenge the foundation before execution: Eric shared that in a previous large business, the team was “doing things right,” but not “doing the right things.” The segmentation was off, and correcting who they were really going after helped the team hit its goals for the next three years.Authentic stories build trust: Eric has had to unlearn the corporate habit of making everything polished before sharing it. He believes people respond when you show the journey, talk about the hardships, and ask for feedback along the way.Systems matter more than scattered tools: Eric warned against building a set of siloed point products. In a venture studio building multiple companies at once, he said you need systems that can scale, especially with the speed of AI.Use AI to strengthen your thinking, not replace it: Eric described writing and revising a LinkedIn post himself before turning to AI. The post performed well, and his takeaway was that people could sense it was naturally written and not simpl...

Judgment in the Age of AI with John Cutler

Jun 24, 2026 50 min

AI is changing how leaders think, decide, and work with their teams. But as John Cutler points out in this conversation, the real shift is not simply about faster answers or more productivity. It is about becoming more aware of the judgment systems we already use, often without noticing. In this episode of the Unlearn Podcast, I’m joined again by John Cutler, product thinker, systems explorer, and Head of Product at Dotwork. We explore how AI can help leaders expose their thinking, pressure test decisions, and build stronger team judgment, while also making it easier to accelerate poor habits, shallow work, and false confidence. John shares practical examples from product prioritization, survey design, objection handling, and team collaboration to show where AI can genuinely improve decision quality. We also get into the tradeoffs: why AI can make work feel like “hard mode,” why downtime still matters, and why intentionality is becoming one of the most important leadership skills in this moment. Key TakeawaysAI exposes how leaders make decisions: AI tends to amplify the decision system already there. When a leader’s thinking is clear, AI can help make it visible and reusable; when it is vague, AI can make that vagueness move faster. Judgment is built differently depending on the situation: John explains that some judgment comes from repetition and tacit pattern recognition, while other judgment develops through coaching, discussion, and working alongside people with more experience. AI can help turn intuition into something teams can use: John’s example of documenting his product prioritization heuristic shows how AI can help make internal judgment concrete. The value comes from helping others understand why certain decisions matter, not just what the decision is. Better AI use starts with knowing what you know: John contrasts product prioritization, where he has deep experience, with survey design, where he knows there is established expertise to draw from. The ski...

Unlearning Executive Judgment: Building Decision-Making Muscles in the Age of AI with Jim Highsmith

Jun 10, 2026 39 min

Jim Highsmith has been thinking about decision-making for a long time. When he wrote Agile Project Management in 2004, he went looking for practical guidance on decision-making in the project management literature and found very little. That gap matters even more now. In this episode, Jim and I talk about why AI raises the stakes for executive judgment. AI can remove friction, speed up work, and take on repeatable tasks, but it can also make it easier for leaders to stop practicing the very capabilities they are paid to use. Jim brings this to life through John Boyd’s OODA loop, the risk of judgment atrophy, mountaineering decisions, Rob Hall’s Everest threshold, Phil Knight’s pattern recognition at Nike, and a personal story from Jim’s own time leading a collaborative project team at Nike. This conversation is really about how leaders build judgment deliberately: by making consequence-bearing decisions, setting thresholds before pressure arrives, creating space for slow thinking, and reflecting honestly on how decisions were made. Key TakeawaysAI can weaken judgment when leaders stop practicing it: Jim compares the risk to driving an autonomous car: the more the system takes over, the less sharp the driver becomes. AI can remove low-value effort, but leaders still need to practice making consequence-bearing decisions.The OODA loop is mostly about orientation: Jim explains that John Boyd’s edge was not just speed, but his ability to update his mental model quickly. For leaders, the real work is noticing when old assumptions no longer fit the situation.Capability is knowledge plus experience plus judgment: AI can make knowledge easier to access, but it cannot replace the experience of carrying consequences. Judgment develops when people make real decisions, reflect on the outcome, and adjust how they think.Thresholds only work when enforced under pressure: Jim uses Rob Hall’s Everest story to show why decision thresholds matter before emotion, ambition, or sunk cost...

The Frequency Era with Chris Walker

May 27, 2026 42 min

AI is changing how work gets done — but more importantly, it’s changing how people understand their value, identity, and ability to navigate uncertainty. That’s one of the reasons I wanted Chris Walker on the show. Chris has spent years helping companies rethink growth, systems, and organizational performance, but this conversation goes far beyond marketing or AI tactics. Drawing on ideas from his new book The Frequency Era, Chris explores what happens when the work that once made people feel valuable can suddenly be done by AI and automation. One idea that stood out to me most in this conversation is that decision quality depends less on information and more on the person making the decision's internal state. In a world where AI can accelerate execution and analysis, judgment, discernment, and emotional clarity become increasingly valuable leadership capabilities — the very qualities machines cannot replicate. Key TakeawaysAI is reshaping identity, not just jobs: Chris explains that many people attach their self-worth to the work they perform. As AI absorbs more execution-based tasks, leaders will need to help teams navigate the emotional disruption that comes with that shift.Judgment becomes more valuable as automation increases: AI can accelerate execution and analysis, but leaders are still responsible for interpreting context, weighing tradeoffs, and making decisions under uncertainty.Decision quality is driven by internal state: Chris argues that calm, present leaders consistently make better long-term decisions under pressure than leaders operating from anxiety or fear.Creativity requires psychological safety: The conversation explores why innovation suffers in environments dominated by pressure and fear, and why teams create better ideas when people feel safe enough to challenge assumptions.Leaders need a compass more than a map: In fast-changing environments, rigid plans become less useful. Adaptability, awareness, and self-trust become more valuable than c...

Incorruptible with Eric Ries

May 13, 2026 54 min

Incorruptible with Eric Ries What if the companies that last the longest are the ones building enough trust that people want to keep participating in them? That’s the idea behind this conversation with Eric Ries — entrepreneur, author of The Lean Startup, and now Incorruptible. Through stories such as Volvo giving away the seatbelt patent, Tony’s Chocolonely opening its ethical supply chain to competitors, and Mary Parker Follett’s idea of the “invisible leader,” we explore how organizations create lasting advantage through trust, shared purpose, and systems that hold together as companies scale. We also unpack why so many businesses drift toward short-term extraction, what leaders misunderstand about organizational health, and why AI is exposing deeper weaknesses in how companies operate. If you’re building a company and questioning whether business-as-usual is still the right operating system, this conversation is for you. Key TakeawaysEthical business can outperform extractive business models: Eric argues that mission-driven companies are not sacrificing performance. In many cases, trust, alignment, and long-term thinking create stronger economic outcomes.Volvo used open ecosystems as strategy: Giving away the three-point seat belt patent helped establish safety as an industry standard while positioning Volvo as the global leader in automotive safety.Tony’s Chocolonely treats its mission as infrastructure: The company’s goal is not simply selling chocolate. Its mission is to eliminate child slavery from the cacao supply chain through systems that competitors can also adopt.Positive externalities can strengthen competitive advantage: Eric explains how companies can create value by improving the broader ecosystem around them instead of maximizing short-term value extraction.Organizations are shaped by invisible leadership: Mary Parker Follett’s idea of the “invisible leader” shows how shared purpose influences decisions when executives are not in the room.Organizat...

Do Less, Win More: How Niche Focus Cuts Through the Noise with Tas Bober

Apr 29, 2026 40 min

Most people think growth comes from doing more—more services, more offers, more complexity. But in this episode, I sit down with Tas Bober, who did the exact opposite. She stripped everything back, focused on one problem, and built a business so clear people can describe it in a single sentence. This conversation is about the courage to simplify—and why that’s far harder (and more powerful) than it sounds. Tas didn’t plan to become an entrepreneur. After layoffs, burnout, and a side experiment on LinkedIn, she found herself with unexpected demand—but no clear direction. It wasn’t until she made a bold, uncomfortable decision to niche down into landing pages that everything changed. What followed is a masterclass in clarity, positioning, and designing a business that actually fits your life—not the other way around. Key TakeawaysNiching down creates clarity: Focusing on one problem made it obvious what Tas does—and why clients should choose her.Doing less accelerates growth: Eliminating distractions and context switching improved both quality and income.Clarity beats capability: Being known for one thing is more valuable than being able to do many.Positioning drives inbound demand: Clear positioning meant clients showed up with defined problems—making selling easier.Data should guide decisions: Tracking time revealed which work actually delivered the highest return.Design your business around your life: Tas optimized for time, flexibility, and energy—not scale for the sake of it. Additional InsightsTrying to do everything can make you lose authority: You shift from expert to order taker.Community accelerates growth: Trusted peers help challenge thinking and shorten the learning curve.Scarcity mindset delays focus: Holding onto everything early can prevent meaningful progress.AI amplifies thinking—it doesn’t replace it: Expertise and nuance still drive better outcomes.Simplicity requires discipline: Even after success, the temptation to expand never goes away. Episod...

Solve Business Problem with People with Melanie Steinbach

Apr 15, 2026 45 min

Most leaders think AI is a technology shift. It’s not. It’s a behavior shift. In this episode, I sit down with Melanie Steinbach—former Chief HR Officer at McDonald’s, Cameo, and MasterClass—to unpack what’s actually changing inside organizations as AI becomes embedded in how we work. Melanie has spent her career solving business problems through people. But she challenges a core assumption: that performance problems are solved by replacing people. Instead, the real leverage comes from coaching, clarity, and creating the conditions for people to do their best work. We explore why AI doesn’t replace leadership—it exposes it. And what that means for AI leadership and decision-making inside modern organizations. Same tools. Same access. Completely different outcomes. The difference comes down to how leaders think, make decisions, and design systems around their teams. We also unpack a critical shift most organizations aren’t ready for: redefining what “valuable work” actually means. For years, being busy—and being in meetings—has been treated as a proxy for value. But when AI handles execution, value moves to judgment, context, and decision quality. If you’re leading teams, navigating transformation, or trying to understand where AI actually fits in your organization, this conversation will change how you think about leadership, work, and performance. Key TakeawaysSolving business problems through people isn’t about replacement: The real leverage comes from coaching, clarity, and creating the conditions for people to succeed.AI exposes how you lead: The same tools produce radically different outcomes depending on how you think and make decisions.Clarity drives performance: When expectations are vague, even high performers struggle to deliver.Context is now the constraint: Information is everywhere, but leaders create value by helping teams interpret and act on it.Busy work is losing its signal: Meetings and activity no longer define value—decision quality does.AI requ...

Stop Chasing Productivity—Start Thinking Better with AI with Misty Shafer Sterne

Apr 1, 2026 39 min

AI isn’t changing the game—it’s exposing how you think. In this episode, I sit down with Misty Shafer Sterne, Vice President of Commercial Technology at American Airlines, to explore what it really takes to lead with AI inside a complex, high-stakes organization. We go beyond the usual productivity narrative and dig into something far more powerful: how AI can sharpen decision-making, surface better questions, and help leaders operate with greater clarity and intent. Misty shares her journey from chasing efficiency to building a personal system for thinking—using AI as a partner to capture ideas, pressure test decisions, and improve how she shows up as a leader. We also unpack why experimentation matters more than metrics early on, how to avoid automating broken processes, and what it looks like to lead in the open so teams can follow. This is a conversation about performance, not productivity—and what it means to truly unlearn how we work. Key TakeawaysAI amplifies how you think: The real advantage isn’t speed but improving clarity, judgment, and decision-making quality.Productivity is just the entry point: The biggest gains come from using AI to enhance performance, not just efficiency.Experimentation must come before measurement: Over-indexing on productivity metrics too early can shut down innovation.Leaders must unlearn being the “answer person”: Great leadership shifts toward asking better questions rather than having all the answers.Decision velocity matters more than idea volume: Success comes from quickly identifying which ideas are worth pursuing, not generating more ideas. Additional InsightsAI as a thinking partner: Misty’s breakthrough came when she used AI to pressure test ideas instead of manage tasks.Externalizing thinking creates clarity: Capturing raw, messy thoughts helps reveal patterns and improve decision-making.Your thinking becomes a reusable asset: AI enables leaders to build a system that stores and evolves their ideas over time.Automating...

Capital Evolution: The Future of Business and AI

Mar 18, 2026 45 min

What role should businesses play in society today? In this episode of the Unlearn Podcast, I sit down with investor, ecosystem builder, and Foundry Group co-founder Seth Levine to explore how capitalism itself may be evolving. Seth’s latest book, Capital Evolution, examines a fundamental question: can modern capitalism create broader opportunity, stronger communities, and more inclusive ownership? Our conversation ranges from declining economic mobility and generational uncertainty to the role of values-driven companies and the rise of AI-powered work. We also dive into how leaders can navigate uncertainty—balancing profit, purpose, and technological disruption. Along the way, Seth shares how a single dinner conversation sparked a two-year research journey, interviewing more than 100 leaders, academics, and entrepreneurs to understand where capitalism may be headed next. This conversation also builds on ideas we’ve explored before on the podcast—particularly with Seth’s long-time collaborator Brad Feld. In our earlier discussion on Give First leadership, Brad challenged the idea that success comes from extraction, instead arguing that generosity, long-term thinking, and community building are the real drivers of sustainable impact. Together, these conversations offer a powerful lens on how leadership, capitalism, and value creation are being redefined. If you’re thinking about the future of work, leadership in an AI-powered world, or how organizations can create both economic and societal value, this episode will challenge some assumptions. Key TakeawaysCapitalism is already evolving: Many leaders still operate as if we’re in a shareholder-first world—but that model has already shifted. Businesses now face growing pressure to balance profit with broader societal impact.Economic mobility is declining: While economies continue to grow in aggregate, fewer people are able to move up financially. This shift is reshaping how younger generations view opportunity and fairne...

Frictionless, Artificial Organizations: Measuring What Matters in the Age of AI

Mar 4, 2026 33 min

AI can now generate code in seconds. Deployment pipelines are faster than ever. And yet, many teams still feel slow. In this episode, I sit down with Nicole Forsgren, world-renowned researcher, co-author of Accelerate, and Senior Director of Developer Intelligence at Google. We explore why speed alone doesn’t create performance — and how hidden friction inside systems, culture, and decision-making quietly holds teams back. Nicole breaks down the SPACE framework, explains why activity metrics create blind spots, and challenges leaders to rethink what productivity really means in the era of AI agents. If you're measuring output but still not seeing impact, this conversation will help you recalibrate. Key TakeawaysProductivity is multidimensional, not just output: Measuring activity alone creates blind spots. Real performance includes satisfaction, quality, collaboration, and flow.System constraints determine team speed: Improving individual teams isn’t enough. Performance improves only when bottlenecks across the entire value stream are addressed.AI accelerates existing systems: Automation increases throughput, but it doesn’t remove friction. Weak processes and structural gaps become more visible as speed increases.Trust becomes a performance factor in AI workflows: As agents contribute to development, validation systems, guardrails, and confidence mechanisms become essential.Strategy must come before acceleration: Building the wrong thing faster does not create value. Leaders must define direction before optimizing delivery. Additional InsightsOrganizations scrutinize AI more than human decisions: We often ask whether AI is producing the right output. Yet we rarely question whether human teams are building the right thing either.AI forces leaders to clarify judgment: Working with agents requires teams to make their assumptions explicit by defining heuristics, edge cases, and decision rules that previously lived in intuition.Many bottlenecks are decision bottlenecks:...

Artificial Organizations: Judgment at Speed in the Age of AI

Feb 18, 2026 30 min

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 decis...

Unlearning Perfectionism While Building Products That Last with Gerry Khouri

Feb 4, 2026 43 min

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...

AI Productivity for Executives: Skyscanner CTO Andrew Phillips

Jan 21, 2026 47 min

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. Epis...

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

Jan 14, 2026 35 min

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 bas...

Investing In Space with Maureen Haverty

Dec 30, 2025 40 min

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:...

The Octopus Organization with Jana Werner & Phil Le-Brun

Dec 17, 2025 36 min

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 strength...

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

Dec 3, 2025 46 min

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...

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

Nov 19, 2025 45 min

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 Rec...

How to Create Irresistible Change for Business Transformation with Phil Gilbert

Nov 5, 2025 43 min

When most leaders think about transformation, they reach for tools and tactics. But real, lasting change doesn’t start with new methods—it starts with culture. In this episode, I sit down with Phil Gilbert, the former General Manager of Design at IBM, who led one of the boldest reinventions in corporate history. After selling his third startup to IBM in 2010, Phil was asked to transform how IBM’s teams worked using design thinking and agile. That effort reshaped the experience of over 400,000 employees and became the subject of a Harvard Business School case study, the documentary The Loop, and coverage in the New York Times and Fortune. We explore how culture drives outcomes, why the team is the atomic unit of change, and how to design a leadership structure that earns trust and creates momentum. Phil brings sharp insight, rich stories, and practical frameworks drawn from a 45-year career spanning startups, scale-ups, and global enterprises. If you’re leading change—or trying to get others to believe in it—this conversation is your blueprint. Phil Gilbert is best known for scaling IBM’s global design transformation. He was inducted into the New York Foundation for the Arts Hall of Fame in 2018 and named an Oklahoma Creativity Ambassador in 2019. Since retiring from IBM in 2022, Phil has focused on helping business and military leaders shift culture at scale to improve innovation and team performance. Key TakeawaysCulture is the system: Real transformation means rewiring people, practices, and places—not just teaching new skills.Teams are the atomic unit of change: Change doesn’t scale through individual mandates. It scales when cross-functional teams deliver new outcomes.Design scales empathy: Phil shares how design thinking isn’t just about aesthetics—it’s a tool for scaling understanding and improving systems.Transformation needs protection: Change teams need structural support and a leadership “shell” that shields them while engaging the broader org.Momentum bea...

How to Clearly Position What You Do with Anthony Pierri

Oct 22, 2025 49 min

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 w...

Why Brains Need Friends with Dr. Ben Rein

Oct 8, 2025 40 min

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 au...

Scaling HR For Growth with Grace with Theresa Cantwell

Sep 24, 2025 39 min

What happens when you stop treating HR as a back-office function and start designing it as a competitive advantage? Theresa Cantwell, Strategic HR Consultant and Director at GSD HR Consulting, believes scaling a company shouldn't mean burning out your team—or yourself. With nearly two decades leading people strategy at companies like Microsoft, ThoughtWorks, and Equal Experts, Theresa has helped organizations across Europe and Asia grow not just fast, but gracefully. In this episode, we dive into the most overlooked challenges founders face when they scale: losing visibility, clinging to control, and skipping the crucial step of designing people and culture systems that can actually support growth. From shadow planning and succession strategies to why success itself can be terrifying, Theresa shares powerful tools and real talk every startup leader needs to hear. If you're moving past 20 employees and want to build a company that lasts—without losing what made it special—this conversation is your playbook. Key TakeawaysStart HR Strategy Early: Don’t wait for burnout or lawsuits—build people ops into your scaling strategy from day one.Shadow Planning Is Essential: Prepare for the worst by confronting your team’s shadow behaviors and stress reactions before they sabotage growth.Succession Planning Isn’t Personal: It's about scalability. Delegate early, document processes, and regularly revisit org design.Growth Changes Everything: Founders need to let go to level up. What got you here won’t get you there.AI in HR Is a Tool, Not a Fix: Automate the repetitive, but double down on building trust and strategic visibility. Additional InsightsHR should be the connective tissue of an organization—not the "issues and tissues" team.Scaling gracefully requires confronting the emotional toll of growth, including fear of success.Theresa shares how early experiences at Microsoft and ThoughtWorks shaped her belief in high-trust, high-agency cultures.Executive coaching and intention...

How Family Offices Are Disrupting Venture Capital and Private Equity with Ron Diamond

Sep 10, 2025 49 min

What happens when you stop chasing returns and start investing in purpose? Ron Diamond, Founder and Chairman of Diamond Wealth, believes the future of finance isn’t just about building wealth—it’s about what that wealth can do. As a trusted advisor to over 100 family offices ranging from $250 million to $30 billion, Ron has spent more than two decades helping ultra-wealthy families align their capital with causes that matter. In this episode, Ron shares how the collapse of Drexel Burnham shaped his perspective on loyalty, legacy, and leadership—and why “patient capital” is poised to disrupt the short-termism of private equity. We explore how purpose-driven investing is solving real-world challenges, from cancer to climate, and what it takes to build sustainable family office infrastructure in an era of unprecedented generational wealth transfer. And the timing couldn’t be more relevant: family offices are no longer niche players. The number of single-family offices has surged 31% since 2019, with projections reaching over 10,700 globally by 2030. As trillions of dollars transition to the next generation, Ron offers a front-row seat to the values, strategies, and systems needed to steward that wealth wisely. Ron is also the Founder, Host, and CEO of Family Office World Media, and helped establish the Family Office Program for TIGER 21, where he chairs a national peer group. He lectures at Oxford, Stanford, Harvard, and the University of Chicago Booth School of Business, and was recently appointed Editor-in-Chief of The National Law Review’s first Family Office newsletter. A LinkedIn Top Voice, TEDx speaker, and former hedge fund founder, Ron began his career on Wall Street at Bear Stearns and Drexel Burnham. Key TakeawaysPeople Over Companies: Ron’s experience during Drexel’s collapse taught him that relationships—not institutions—are what endure.Patient Capital Is a Game-Changer: Family offices can think in decades, not quarters, offering strategic advantage over tr...

The Power of Real Conversations with David Homan

Aug 27, 2025 41 min

What if networking wasn’t about schmoozing but about being seen? David Homan joins me to unlearn the myths of traditional networking and share how vulnerability, deep listening, and small group connection can foster truly meaningful relationships. As a master connector, classical composer, and co-author of Orchestrating Connection, David breaks down the silent skills that build trust, activate communities, and transform the way we gather. David Homan is the founder and CEO of Orchestrated Connecting, a global community of connectors; Orchestrated Opportunities, an impact-focused advisory firm; and SOAR CONNECT, a start-up focused on the strength of authentic relationships. He hosts the Orchestrated Relationships podcast on developing relationship value, is an active classical composer, and a proud father of two. From middle-class beginnings as the son of a college professor and nonprofit-focused mother, he has built a network that reaches into the most private and powerful circles globally, all while honoring a code of purposeful community building. Key TakeawaysSmall Groups Create Big Impact: Starting events with curated small groups breaks social barriers and sets the stage for authentic connection.Vulnerability Builds Real Relationships: Opening up—even subtly—invites empathy and depth that surface-level networking can't achieve.Help Without Keeping Score: Giving without expecting reciprocity strengthens your reputation and extends your reach.Design Moments That Resonate: Successful events don’t depend on cocktails or keynote speeches—they’re built on meaningful first impressions.Asking Is a Skill, Not a Weakness: Givers often struggle to ask for support—David’s Impact Ask framework helps mission-driven people share their needs with clarity. Additional InsightsMost Networking Events Are Designed to Fail: Traditional formats emphasize aesthetics over connection—David redesigns them to foster immediate, meaningful dialogue.Shared Vulnerability Activates Group Trust...

The Sound of Freedom and Healing Trauma with Paul Hutchinson

Aug 13, 2025 47 min

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 TakeawaysTrauma 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-aw...

Give First and the Ripple Effect of Generosity with Brad Feld

Jul 30, 2025 46 min

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 TakeawaysGenerosity 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 InsightsRedefine 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 B...

Why AI-First Digital Product Consultancies Will Win Big with David Tuck

Jul 16, 2025 49 min

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 TakeawaysCraft 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 InsightsRedefine Leadership as Service: A CEO’s job...

Bold Go-To-Market Tactics: Just Evil Enough to Win with Alistair Croll

Jul 2, 2025 44 min

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 TakeawaysStart 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 InsightsTest 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...

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

Jun 18, 2025 36 min

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 TakeawaysAct 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 I...

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

Jun 3, 2025 45 min

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 i...

The Future of Housing and Modular Home Building with John Avrett

May 21, 2025 38 min

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:...

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

May 7, 2025 35 min

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 Hoq...

Unlearning Legacy Systems to Build Antifragile AI Operating Models with Ja-Naé Duane

Apr 23, 2025 46 min

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 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 h...

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

Apr 9, 2025 43 min

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...

The Neuroscience of High-Performing Teams for Leaders to Achieve Workplace Success | Dr. Marcia Goddard

Mar 26, 2025 38 min

Welcome back to the Unlearn podcast! Today, we're exploring neuroscience with Dr. Marcia Goddard, a top neuroscientist and high-performance expert. As the founder of Brain Matters, a LinkedIn Top Voice, TEDx speaker, and a Neuroscientist. She's known for making science practical for business success. Her work with Formula 1, where she studied behavior and culture within teams to develop comprehensive strategies that enhance performance, along with her contributions to Leiden University, and The Contentment Foundation has helped leaders and teams boost performance and teamwork. She is also the Board Advisory Member of Equalture. Tune in for an insightful talk on unlocking human abilities and building creative workplace cultures! She is a respected neuroscientist who is dedicated to guiding young professionals and bringing fresh ideas into different industries. Dr. Marcia’s work is a valuable resource for anyone aiming to make a big impact in technology and business. Dr. Marcia Goddard, a neuroscience expert with over 10+ years of experience, applies brain science to boost workplace performance and culture. She has consulted with high-performance teams, including Formula 1 and Fortune 500 companies, optimizing team dynamics. Her thought leadership focuses on psychological safety and inclusion, guiding organizations toward innovation and growth. Key Takeaways:Expanding Globally: Dr. Marcia Goddard’s strategies for international growth. Overcoming Challenges: Solutions for fast-changing industries. Adapting to Change: Stay flexible, ditch outdated methods. Personal Experience: Dr. Goddard’s lessons in action. Additional Insights:Effective Strategies: Dr. Marcia Goddard on reshaping industries. Thriving in Growth: Tips for fast-expanding businesses. Experience to Innovation: Dr. Goddard’s journey to better solutions. Get ready for an enlightening conversation with Dr. Marcia Goddard on infusing new ideas into business strategies and fostering a culture of innovation...

Why Playing Too Small Is Stopping Your Finance Career Growth with Kristie Edling-Day

Mar 12, 2025 38 min

Welcome to UNLEARN, the podcast where we will discuss the transformative journeys, innovative tactics, and the pivotal mindset shifts necessary for authentic progress and development. Today, I'm thrilled to welcome Kristie Edling-Day, the current Executive Vice President and Chief Information Officer of Advisor Technology at LPL Financial, and former Principal and Chief Information Officer at Vanguard, a pioneer in strategic development and information management. Kristie is not just a leader; she also loves helping young professionals grow and bringing new ideas to different industries. The book ‘Innovate to Elevate: Transforming Markets and Minds in Southeast Asia’ explores groundbreaking insights, offering valuable strategies for those aiming to drive change in technology and business. Kristie has worked in the Financial Services industry for over 18 years, helping improve technology and develop new products. At LPL Financial, she manages Client Works, a platform that helps over 20,000 advisors with important tools for handling accounts, investments, trading, advisory programs, and compliance. She also leads LPL’s strategy for AI, making sure the company and its advisors have access to the latest in what technology can do both for efficiency and growth. Key Takeaways:Growing Businesses Worldwide: Kristie shares how to expand companies across different countries. Facing Challenges: Tips on handling problems in fast-growing industries. Learning and Adapting: Why being open to change and unlearning old ways helps with innovation. Using Personal Experience: How Kristie solves problems based on her own challenges. Additional Insights:Smart Strategies and Strong Operations: Kristie explains how these key skills can change industries. Succeeding in Fast-Growing Markets: How to handle challenges in quickly expanding businesses. Turning Experience into Innovation: How Kristie uses her own experiences to create better business solutions. Get ready for an insightful ta...

How to Build a Viral App by Finding Untapped Niches for Explosive Growth | Crystal Gonzalez

Feb 26, 2025 55 min

Welcome to UNLEARN, the podcast where we explore the transformative experiences, strategies, and mindset shifts essential for true innovation and growth. Today, I’m honored to host Crystal Lee Gonzalez, a trailblazer in strategic growth and innovation across Southeast Asia. Born and raised in the Philippines, Crystal has spent the last fifteen years shaping and scaling some of the region’s most prominent brands. She is the Co-Founder & CEO of NoneAway and was previously the Co-Founder of PICK.A.ROO. Her leadership has left a significant mark on multiple industries, serving as the Former CEO of Canva Philippines & Southeast Asia, Former President & Managing Director at HonestBee, and Former Regional Head of Southeast Asia at Viber. With a career spanning top-tier organizations, she also held key roles as the Group Account Director at Tribal Worldwide, Head of Branding at Lazada Group, and Marketing Head at YAHOO. Beyond launching and leading businesses, Crystal finds deep fulfillment in mentoring emerging talent and reshaping industries through innovation. Her expertise is now encapsulated in her upcoming book, Innovate to Elevate: Transforming Markets and Minds in Southeast Asia, a must-read for those looking to make a lasting impact in technology and strategic development. Key Takeaways:Scaling Global Startups: Crystal details her strategies for business expansion in Southeast Asia.Embracing Challenges: Insights into overcoming obstacles in high-growth environments.Unlearning for Growth: How adapting and unlearning fuels innovation.Leveraging Personal Experiences: Crystal's approach to creating solutions from personal pain points. Additional Insights:The NoneAway Model: Crystal demonstrates how strategic thinking and operational excellence revolutionize real estate.Adapting in High Growth Markets: Mastering the challenges of rapid expansion and market dynamics.Innovative Solutions from Personal Insights: How Crystal’s personal experiences inspire practical business...

How AI is Changing Product Management Forever with Diana Stepner

Feb 12, 2025 36 min

Welcome to UNLEARN, the podcast where we explore the stories, strategies, and mindset shifts that drive real innovation and growth. Today, I’m glad to be joined by Diana Stepner, a true trailblazer in the world of product management and people-centered leadership. A Silicon Valley native, Diana has spent over two decades building and leading global product teams for companies like Monster, Cheapflights (later acquired by Kayak), Salesforce, and Razorfish. As Co-Founder, at Product Gold and Former VP of Product Management at Pearson, she has honed her expertise in creating impactful solutions. Along the way, she discovered that while launching great products is exciting, helping people launch their careers is even more rewarding.. Diana’s passion for fostering talent and preparing organizations for the future shines in her new book, Next-Gen Product Management: Future Proof Your Career. It’s a must-read for anyone navigating the rapidly evolving landscape of technology, teams, and innovation. We dive into her journey, the lessons she’s learned, and the practical advice she has for product leaders looking to thrive in an ever-changing world. Check out her website at www.dianastepner.com to learn more. Key Takeaways:Product vs. Project Management: Diana explains the key differences. Supercharging Product Managers: How top contributors maximize impact. Winning with Teams: The power of cross-functional collaboration. Breaking Into Product Management: Trends shaping new career moves. Additional Insights:The Product Gold Framework, Diana shows how adaptability and empathy unlock market opportunities. Engagement in the Digital Age by mastering attention in a world full of distractions. Thinking Differently in Business: How challenging norms drives big advancements. Prepare for an enlightening discussion with Diana Stepner on transforming traditional product strategies and fostering a culture of creativity and innovation. Episode Highlights: [00:33] -Episode Introducti...

How the Attention Economy is Redefining Traditional Marketing with Emily Ross

Jan 29, 2025 35 min

Welcome to the UNLEARN Podcast! Today, we’re joined by Emily Ross, co-author of Just Evil Enough and a leader in brand strategy and creativity. With a career spanning tech innovation, marketing, and even circus performance, Emily approaches challenges from unconventional angles. As Director of Brand Strategy at X (formerly Twitter) for EMEA, Emily also serves as an Advisory Board Member at SXSW and GoGreen Routes, an EU funded, pan-European research project on nature-based connectedness, as Co-founder of Resonance Festival (Resonance-Lough Derg), and a mentor to startups across Europe. In this episode, she shares her approach to subversive marketing, reframing obstacles as opportunities and using bold tactics to achieve extraordinary results. Drawing inspiration from disruptors like Tesla, Emily reveals how creativity and curiosity can transform business outcomes. Whether you’re looking to reimagine your marketing strategies or disrupt the status quo, Emily’s expertise is an invaluable guide. Key Takeaways: Unconventional marketing tactics involve reframing challenges and using bold strategies like zero-day exploits to help brands stand out.The power of creativity lies in applying attention-grabbing skills across industries, as seen through lessons from a diverse career.Turning flaws into strengths, as seen with Tesla and Space Invaders, shows how weaknesses can become powerful advantages.Consistency over brilliance emphasizes that success stems from daily effort and experimentation, not rare moments of genius. Additional Insights: The Recon Canvas Framework uncovers market opportunities and shows the need for constant adaptability as strategies evolve.Capturing attention in the digital age requires standout marketing in a noisy, distracted world.Subversive thinking from Just Evil Enough shows how breaking rules can drive business success. Get ready for a fascinating conversation with Emily Ross on rethinking traditional approaches, embracing creativity, and crafti...

How Product Managers Can Avoid Startup Failures and Drive Growth with John Cutler

Jan 15, 2025 47 min

Welcome to the UNLEARN Podcast! Today, we’re joined by a thought leader and prolific voice in product management and organizational design, John Cutler. With a unique ability to navigate the “beautiful mess” of product development, John has spent his career exploring the complex overlaps of product, UX, and strategy. Currently serving as Head of Product at Dotwork, John has previously held impactful roles such as Senior Director of Product Enablement at Toast and Product Evangelist at Amplitude, where he collaborated with thousands of product teams worldwide. His extensive experience spans B2B SaaS giants like Zendesk, Pendo, and AppFolio, as well as B2C, ad-tech, banking, and media industries. Known for his insightful writing, John has authored nearly a thousand posts across various platforms, captivating readers with his deep understanding of product dynamics. Whether you’re seeking to level up your product thinking or gain practical tips on team enablement, John’s expertise offers unparalleled insights. Key Takeaways:The Beautiful Mess of Product Development: John’s approach to embracing complexity and context in product management to uncover innovative solutions.Unlearning and Growth: How letting go of rigid practices and adapting to change can unlock greater potential for teams and leaders.Writing as a Catalyst for learning: The power of consistent writing in shaping ideas, refining strategies, and building meaningful connections in the product community. Additional Insights:Product Ecosystems in Flux: John talks about the dynamic nature of product management, highlighting how roles and best practices evolve with organizational and market shifts.Gamifying the Creative Process: Insights into how John uses tools and techniques to make writing, ideation, and problem-solving more engaging and productive.Rethinking Organizational Models: Exploring how companies can overcome challenges by reimagining structures, roles, and team dynamics for the modern era. Get ready...

Proven Strategies to Create Accountability Without Agency with Lee Vorthman

Dec 18, 2024 31 min

Welcome to the UNLEARN Podcast! Today, we’re joined by Lee Vorthman, Vice President of Strategic Security Initiatives at Oracle. Lee leads a global team to protect and strengthen Oracle's operations. He is also a Global CISO Advisory Board Member at HMG Strategy and an Advisory Board Member for Phoenix Security. His career began in the US Navy, and he has since held key roles across defense, technology, cloud, education, and oil & gas industries. Lee’s past roles include Chief Security Officer for Oracle's Advertising group, leading Global Security Engineering at Pearson Education, and serving as Chief Technology Officer for Federal Civilian Agencies at NetApp. In this episode, Lee shares insights on leveraging technology for growth, navigating cultural transformations, and building resilient organizations. Key Takeaways:Mastering Security Fundamentals: Lee highlights the importance of staying grounded in foundational security practices while adopting innovative technologies like AI to address evolving challenges.Building Trust and Influence: Discover Lee’s techniques for fostering collaboration, psychological safety, and cultural change to drive impactful security initiatives.The Power of Diverse Skills: Learn why developing a broad skill set across disciplines like engineering, finance, and HR is essential for empathetic leadership and effective problem-solving. Additional Insights:Cultural Change in Security: Get ready for a thought-provoking conversation with Lee Vorthman on leadership, innovation, and building resilient organizations!Balancing Speed and Resilience: Insights on how businesses can prioritize innovation while maintaining strong operational fundamentals.The Future of Cybersecurity: Exploring emerging trends like AI and their implications for addressing new and complex threats. Get ready for a thought-provoking conversation with Lee Vorthman on leadership, innovation, and building resilient organizations! Episode Highlights: 00:36 - Episode Intr...

Why Unlearning Cultural Norms Is Essential for Thriving in Global Leadership with Ani Filipova

Dec 4, 2024 46 min

Welcome to the UNLEARN Podcast! Today, we’re joined by an inspiring leader in global banking and transformation, Ani Filipova. With over two decades of experience, Ani has made her mark as a former international banking executive, setting up and managing three banks, including Citibank Bulgaria. She also led the transformation of a $2 billion business across 16 countries as Regional COO for Citibank Treasury and Trade Solutions in Asia. Ani’s path to success was anything but conventional. Fueled by a passion for travel, she overcame rejections and seized every opportunity to explore the world and build a remarkable career. Now, Ani is reshaping her journey through a “portfolio career,” as the Founder & CEO of Change Advisory, drawing from her wealth of experience to inspire others with insights on leadership, transformation, and reinvention. Key Takeaways:Exploring Beyond Boundaries: Ani’s journey of growing up behind the Iron Curtain, finding creative ways to explore the world despite restrictions.Speaking Up and Taking Risks: Strategies Ani used to conquer anxiety, master the art of speaking up, and embrace bold decisions in high-stakes situations.Global Team Collaboration: Insights on fostering alignment and driving collaboration across diverse teams to achieve success in complex, multinational organizations. Additional Insights:Embracing Change: Ani highlights the challenges and rewards of adapting to digital transformation.Cross-Cultural Collaboration: Understanding local customs as a foundation for trust and teamwork.Unlearning to Grow: Letting go of old habits to thrive in evolving business landscapes. Get ready for an inspiring and transformative conversation with Ani Filipova on embracing change, leadership, and the power of reinvention! Episode Highlights: 00:36 - Episode Introduction "If you don't speak up, if you don't show your work. If you don't share your opinions, that's not good at all. 01:27 - Introduction to the Episode: Barry introduces Ani Fi...

See all 193 episodes

–

0 ratings from members

Rate this podcast

No reviews yet — be the first member to rate "Unlearn".

This podcast, its content and its artwork are not owned by, affiliated with, or endorsed by Castquire.

How Leaders Turn AI Investment Into Better Business Outcomes with Melanie Steinbach

Share this podcast

Live Chart rankings

Chart history

🇩🇰 Entrepreneurship Best #149

Holding at #149 — the line fills in as this chart moves.

🇮🇹 Entrepreneurship Best #158

Holding at #158 — the line fills in as this chart moves.

Podcast details

Created by: Barry O'Reilly
Status: Active
Latest episode: Nov 11, 2026
Episodes: 193
Release period: Every two weeks
Avg. episode length: 39 min
Explicit: No
Language: English

Links

Official website ↗ Apple Podcasts ↗ RSS feed ↗

Is this your podcast?

Claim it to show it on your profile. Using the email from your RSS feed approves it instantly.

Keep listening

Discover more podcasts like this.

Browse podcasts See the charts