Unlearn

About Unlearn

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.

Publisher

Barry O'Reilly

Category

business

Language

en

Explicit

No

First episode

18 Apr 2019

Latest episode

14 Oct 2026

Latest episodes

1 of 190 episodes have a transcript.

1. 

   14 Oct 2026

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

   Making technology faster does not automatically make the business better. John Marcante (https://www.linkedin.com/in/john-t-marcante/?isSelfProfile=false) spent 28 years at Vanguard (https://www.linkedin.com/company/vanguard/), including serving as Global CIO and leading its high-net-worth and advice business. As Deloitte’s (https://www.linkedin.com/company/deloitte/) 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 Takeaways Redesign 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 Insights Technology foundations still matter: John cautions that organized data, modern platforms, and addressing technical debt remain important. Work redesign does not remove the need for those foundations. Technical capability and organizational influence are different: John describes a gap between technology leaders’ confidence in scaling AI and their confidence in changing how the business operates. Leaders need to model the change themselves: Barry shares how Progyny CEO Pete Anevski experimented with new ways of working and openly discussed what he was learning, helping others feel able to experiment. Humility helps reduce learning anxiety: John emphasizes honest communication and vulnerability when people are uncertain about their roles. Leaders do not need every answer before showing how they are learning. Stay close to the people doing the work: John moved his office onto the advisor floor to listen to client conversations, understand concerns, and help connect the change to what mattered for clients. Episode Highlights 00:00 – Boards Are Asking Where the AI Value Is John opens with the gap between AI adoption and business value, and the questions boards are asking about their investment. 01:41 – Introducing The Adaptive Enterprise Series Barry introduces John and explains how their conversations grew into five articles and five companion podcasts. 02:54 – What Should Change Because of AI? Barry frames the leadership challenge around what new capabilities make possible for work. 05:30 – When IT Gets Faster Than the Business John recounts Vanguard’s cloud journey, the bottleneck that shifted into the business, and the move to cross-functional product teams. 07:50 – Business and Technology Need to Move Together Barry shares a lesson from American Airlines about involving the wider business in transformation. 09:45 – Scaling AI Without Changing the Operating Model John discusses why technical readiness does not necessarily give leaders the influence to change established ways of working. 11:07 – Redesign the Whole Process Barry explains how local productivity gains can leave end-to-end work unchanged, while John describes aligning teams around shared outcomes. 15:21 – When Automation Challenges People’s Roles Barry explores the anxiety people feel when tasks that have defined their work begin to change. 17:13 – What Will You Do With the Time You Free Up? John explains why efficiency alone is insufficient and why leaders need to direct capacity toward valuable work. 19:01 – Leaders Go First Barry shares how Progyny’s CEO modeled experimentation, and John discusses humility and vulnerability in leadership. 22:46 – Helping Advisors Redefine Their Value John describes moving the focus from portfolio mechanics and larger client books to client loyalty and important family decisions. 27:26 – The Adaptive Enterprise Loop John explains the continuous cycle of capabilities, work redesign, outcomes, governance, and learning. 30:50 – Where Executive Teams Can Start John offers practical starting points: rethink work, identify where judgment creates value, and align people around business outcomes. Useful Resources John Marcante on LinkedIn - https://www.linkedin.com/in/john-t-marcante/?isSelfProfile=false (https://www.linkedin.com/in/john-t-marcante/?isSelfProfile=false) The Adaptive Enterprise Series: Article 1 - https://barryoreilly.com/explore/blog/how-ai-is-changing-work-and-leadership/ (https://barryoreilly.com/explore/blog/how-ai-is-changing-work-and-leadership/) Measure AI Outcomes survey - https://artificialorganizations.com/measure-ai-outcomes (https://artificialorganizations.com/measure-ai-outcomes) Artificial Organizations - https://geni.us/artificialorgs (https://geni.us/artificialorgs) Vanguard on LinkedIn - https://www.linkedin.com/company/vanguard/ (https://www.linkedin.com/company/vanguard/) Deloitte on LinkedIn - https://www.linkedin.com/company/deloitte/ (https://www.linkedin.com/company/deloitte/)

2. 

   30 Sept 2026

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

   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 Takeaways Start 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 Insights Resilience 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 people, helping them work together, and building strong teams around difficult problems. Luck belongs in the entrepreneurship story: Timing, advice, unexpected opportunities, and good fortune can play an important role even when successful founders later describe a more deliberate strategy. Nearform was built around open source and small, senior teams: The company was built on a belief in open technology and in smaller groups of experienced people creating greater impact. The transformation experts are being disrupted too: After helping companies navigate mobile, cloud, and ecommerce, Nearform now finds its own services business directly affected by AI. Episode Highlights 00:00 – Solve Problems Before Chasing Money Ciaran explains why he has always been more interested in solving meaningful problems than pursuing technology or quick financial returns. 02:32 – Guest Introduction: Ciaran Cosgrave Meet Ciaran Cosgrave, CEO of Nearform, whose unconventional career began with a decade spent running refugee camps before moving into entrepreneurship and technology. 03:52 – From Refugee Camps to Technology Ciaran shares how he spent the first ten years of his career working in refugee camps before entering technology. 05:46 – Giving His Early Career to Others A teenage encounter with a technology entrepreneur inspired Ciaran to spend the early years of his career serving others and tackling difficult problems. 08:18 – Becoming an Entrepreneur by Accident After struggling to enter traditional corporate roles, Ciaran found an opportunity in financial services and started building technology businesses. 11:45 – Focus on Problems, People, and a Little Luck Ciaran explains why understanding the problem, finding great people, and acknowledging luck have shaped how he builds businesses. 15:43 – What Drew Ciaran to Nearform Ciaran describes Nearform’s origins and its early belief in open-source technology, small senior teams, and software as a force for good. 21:03 – When the Transformation Experts Get Disrupted After years of helping companies navigate digital transformation, Nearform now finds its own industry being reshaped by AI. 25:45 – Knowing What to Build Is Still Hard Ciaran argues that judgment about what to build remains one of the biggest challenges for organizations using AI. 29:38 – From Months of Prototyping to Days and Weeks AI-assisted development allows teams to move from ideas to prototypes much faster and examine more alternatives before committing. 33:20 – Making More Bets With Greater Optionality Barry explores how cheaper experimentation allows teams to test multiple possibilities instead of placing one large bet. 36:06 – When Innovation Becomes the Bottleneck Ciaran explains why organizations need stronger filtering mechanisms as teams generate and prototype more ideas. 39:18 – Turning AI’s Potential Into Reality Ciaran shares his optimism about putting AI into production and using it to build new services and tackle difficult problems. Useful Resources Ciaran Cosgrave on LinkedIn - (https://www.linkedin.com/in/ciarancosgrave/)https://www.linkedin.com/in/ciarancosgrave/ (https://www.linkedin.com/in/ciarancosgrave/) Nearform Website - (https://www.nearform.com/)https://www.nearform.com/ (https://www.nearform.com/) Nearform on LinkedIn - (https://www.linkedin.com/company/nearform/)https://www.linkedin.com/company/nearform/ (https://www.linkedin.com/company/nearform/) Artificial Organizations – (https://geni.us/artificialorgs)https://geni.us/artificialorgs (https://geni.us/artificialorgs) Read Artificial Organizations? Leave a review on Amazon – (https://www.amazon.com/review/create-review/ref=cm_cr_othr_d_wr_but_top?ie=UTF8&channel=glance-detail&asin=1067626328)https://www.amazon.com/review/create-review/ref=cm_cr_othr_d_wr_but_top?ie=UTF8&channel=glance-detail&asin=1067626328 (https://www.amazon.com/review/create-review/ref=cm_cr_othr_d_wr_but_top?ie=UTF8&channel=glance-detail&asin=1067626328) Follow Barry O’Reilly LinkedIn: (https://www.linkedin.com/in/barryoreilly)https://www.linkedin.com/in/barryoreilly (https://www.linkedin.com/in/barryoreilly) Website: (https://barryoreilly.com)https://barryoreilly.com (https://barryoreilly.com) Facebook: (https://www.facebook.com/barryoreillyauthor/)https://www.facebook.com/barryoreillyauthor/ (https://www.facebook.com/barryoreillyauthor/) X: (https://x.com/barryoreilly)https://x.com/barryoreilly (https://x.com/barryoreilly) Instagram: (https://www.instagram.com/barryoreilly/)https://www.instagram.com/barryoreilly/ (https://www.instagram.com/barryoreilly/)

3. 

   16 Sept 2026

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

   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 Takeaways Past 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 Insights Speed can be an advantage over scale: A Cloud Guru prepared courses before AWS certifications launched, then updated them using real exam feedback. Playfulness can strengthen a product: Short, entertaining lessons made cloud training easier to engage with and helped A Cloud Guru stand out. Paying customers provide stronger signals: Payment shows whether a problem matters enough to solve and makes the customer’s feedback more meaningful. AI is changing team ownership: Cuttable is moving from teams that own system components to teams accountable for measurable customer outcomes. Founder optimism needs a counterweight: Glitch Capital uses analysts and experienced operators to challenge assumptions and add rigor to investment decisions. Episode Highlights Episode Highlights 00:00 – Episode Recap Sam reflects on starting again after a major exit and learning that customers care more about solving their problem than a founder’s reputation. 02:13 – Guest Introduction: Sam Kroonenburg Meet Sam Kroonenburg, CEO and co-founder of Cuttable, co-founder of A Cloud Guru, and founder investor at Glitch Capital. 03:29 – The Moment Technology Clicked Sam traces his entrepreneurial journey back to receiving his first computer and learning to code through an online pen pal. 09:11 – Winning Through Speed and Play Sam explains how A Cloud Guru used informed bets, rapid updates, and playful learning experiences to move faster than larger organizations. 12:26 – Starting Again and Unlearning Founder Instinct Moving from a 600-person company to an early-stage startup forced Sam to test his assumptions and relearn how to earn customer trust. 17:51 – Running a Startup Like a Large Company Sam initially brought too much structure, reporting, and sales pressure into Cuttable before refocusing on product-market fit. 20:56 – Why Cuttable Went Back to Zero After reaching nearly $1 million in ARR, Cuttable released every customer and rebuilt around end-to-end automation. 27:48 – Why Paying Customers Change the Signal Sam explains why payment reveals whether a problem matters enough to solve and makes customer feedback more meaningful. 29:43 – Stop Teaching AI to Work Like a Human Cuttable learned to give AI the available data and desired outcome instead of forcing it to follow a prescribed human process. 34:45 – Organizing Teams Around Outcomes Sam explores why engineers focused on customer impact often embrace AI and how Cuttable is organizing teams around measurable outcomes. 38:41 – Why Founder Optimism Needs a Filter Sam explains how Glitch Capital balances founder optimism with analysts and experienced operators who challenge assumptions. 42:03 – Smaller Teams and Bigger Impact Sam shares his optimism that AI will help smaller teams create impact at a scale that once required much larger organizations. FAQs Q1. What did Sam Kroonenburg have to unlearn after building A Cloud Guru? Sam had to unlearn the confidence and operating habits that came with previous success. At Cuttable, he found that reputation could not replace customer value, evidence, or the search for product-market fit. Q2. Why did Cuttable give up nearly $1 million in annual recurring revenue? Enterprise demands were pulling Cuttable toward custom work and manual intervention. When engineers began generating and fixing campaigns themselves, the team released those customers and rebuilt around end-to-end automation. Q3. How does Sam Kroonenburg think AI changes product development? Sam believes teams should spend less time telling AI how to perform a task and more time defining the desired outcome. AI can then use the available data to determine the best method. Q4. Why does Sam prefer feedback from paying customers? Payment shows that a problem matters enough to solve. Free users can offer feedback without genuinely valuing the product, while paying customers provide a stronger signal. Q5. How is AI changing the way Cuttable organizes engineering teams? Cuttable is organizing teams around measurable customer outcomes instead of software components. Teams can use AI and evaluation systems to improve those outcomes continuously. Useful Resources Cuttable (https://www.cuttable.com/) — Sam Kroonenburg’s AI-powered creative production system for advertising. A Cloud Guru (https://www.pluralsight.com/cloud-guru) (https://www.pluralsight.com/cloud-guru)— The cloud computing education company co-founded by Sam and later acquired by Pluralsight. Glitch Capital (https://www.glitchcap.com/) — The Australia and New Zealand founders fund Sam started with fellow founders and operators. AWS re:Invent (https://aws.amazon.com/events/reinvent/) — Discussed in Sam’s story about how A Cloud Guru prepared training for new AWS certifications at launch speed. Square Peg (https://www.squarepeg.vc/) — Cuttable’s investor, whose response to the company’s decision to reset revenue reinforced Sam’s understanding of seed-stage investing. Artificial Organizations (https://geni.us/artificialorgs) — https://geni.us/artificialorgs (https://geni.us/artificialorgs) Read Artificial Organizations? Leave a review on Amazon - (https://www.amazon.com/review/create-review/ref=cm_cr_othr_d_wr_but_top?ie=UTF8&amp;channel=glance-detail&amp;asin=1067626328)https://www.amazon.com/review/create-review/ref=cm_cr_othr_d_wr_but_top?ie=UTF8&amp;channel=glance-detail&amp;asin=1067626328 (https://www.amazon.com/review/create-review/ref=cm_cr_othr_d_wr_but_top?ie=UTF8&amp;channel=glance-detail&amp;asin=1067626328) Follow Barry O'Reilly: LinkedIn: (https://www.linkedin.com/in/barryoreilly)https://www.linkedin.com/in/barryoreilly (https://www.linkedin.com/in/barryoreilly) Website: (https://barryoreilly.com/)https://barryoreilly.com (https://barryoreilly.com) Facebook: (https://www.facebook.com/barryoreillyauthor/)https://www.facebook.com/barryoreillyauthor/ (https://www.facebook.com/barryoreillyauthor/) X:<a href="https://x.com/barryoreilly" rel="noopener...

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

Published 7 May 2025 · Transcript excerpt

[…] I mean, and it's well, well established that you got to cover those basics, and, you know, you have food on the table, you get roof on your head, you reach certain level in your life, then you start questioning, like, what's next, and why am I here, or hopefully you will be asking, why am I here, and what impact I'm making, being a positive, you know, influence, or a negative influence, and etc. And each time, what happens is something happens to you, at least that's what happened to me, various stages of your life, you kind of try to redefine what that means to, you know, self -extualization of who you are, and what you're doing, right? […]

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