Unlearn

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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.

• 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.

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

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

[01:00] - Episode Recap 

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

[02:03] - Guest Introduction: Francesca Cortesi 

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

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

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

[07:10] - Facing Rejection and Redefining Identity 

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

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

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

[15:20] - What Francesca Had to Unlearn

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

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

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

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

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

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

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

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

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

Follow Our Guest:

LinkedIn Accounts: 

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

Websites:   

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

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly 
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• Email: [email protected]

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.

• 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.

• 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 and growth.

[00:36] - Episode Precap

"Welcome back to the Unlearn podcast, where we challenge conventional thinking to unlock high performance and breakthrough innovation."

[01:17] - Guest Introduction: Dr. Marcia Goddard

“I'm joined by Dr. Marcia Goddard, a neuroscientist, author, and keynote speaker specializing in applying brain science to workplace performance and culture.”

[02:30] - Navigating Introversion, Networking Opportunities, and Career Growth

"My career was once a series of what I called coincidences, but I no longer believe they were."

[06:46] - Unlearning Misconceptions in Neuroscience

"There are two answers to that. My favorite quote is, 'If the brain were simple enough for us to understand, we would be too simple to understand it.”

[10:26] - Practical Tips for High-Performance

"It's a good question, especially in individual coaching. I think that's what it's related to."

[12:40] - The Importance of Reflection in Decision-Making

"We often tell ourselves we must decide now, but that’s rarely the case."

[15:58] - Enhancing Team Communication

"The most common thing I see at a team level, especially in growing organizations."

[18:44] - Remote Work and Maintaining Connections

"For remote organizations, let’s be clear: I don’t support full-time office work."

[26:04] - Future of High-Performance Teams

"Looking ahead, what excites you most in the industry, and what do you think needs to be unlearned?"

[29:31] - Rethinking Diversity and Inclusion Programs

"We need to unlearn the notion that ticking boxes creates impact and that DEI is just the right thing to do."

[35:52] - Future Trends in Neuroscience and Performance Teams

"Looking ahead, what excites you most about the future of performance teams and neuroscience?"

Follow Our Guest

LinkedIn Accounts: 

• Dr. Marcia Goddard: https://www.linkedin.com/in/mngoddard/
• Brain Matters: https://www.linkedin.com/company/brainmattersconsulting/ 
• Formula 1: https://www.linkedin.com/company/formula-one-management-ltd/ 
• Equalture: https://www.linkedin.com/company/equalture/ 
• The Contentment Foundation: https://www.linkedin.com/company/the-contentment-foundation/ 
• Leiden University - Faculty of Archaeology: https://www.linkedin.com/company/faculty-of-archaeology-university-of-leiden/ 

Websites:   

• Brain Matters: https://brainmattersconsulting.com/ 
• Formula 1: https://www.formula1.com/ 
• Equalture: https://www.equalture.com/ 
• The Contentment Foundation: https://www.contentment.org/ 
• Leiden University - Faculty of Archaeology: https://www.universiteitleiden.nl/en/archaeology 

____________________________________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook 

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• LinkedIn: https://www.linkedin.com/in/barryoreilly 
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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.

• 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.

• 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 talk with Kristie Edling-Day on bringing fresh ideas into business strategies and building a culture of innovation and growth.

[00:37] - Episode Introduction

"Systems like LPL’s ClientWorks platform are so important and they help over 20,000 advisors manage their work more effectively and stay compliant. "

[01:35] - Guest Introduction: Kristie Edling-Day.

“I did not join Vanguard thinking I wanted to be an executive in technology."

[05:20] - Turning Point in Career Growth Choices and Embracing Uncertainty.

“On my first day at the new job, I realized that I didn't really know the boss or even the names of all the divisions in the company."

[10:05] - Nurturing Passion and Building Effective Leadership Teams

"What are the things you were doing when you chose to stay late, didn't mind, and in fact, were excited or couldn't wait to get up the next day?"

[16:28] - Adjusting to New Roles and Unlearning

"I think it is one of the most profound realizations that two organizations can think about roles and define them very differently."

[24:05] - Discovering Aha Moments in Personal Growth

"Some of the things that helped you, like those aha moments? Now that you have new clarity, what are you doing differently?"

[28:54] - The Need for Unlearning in Industry Evolution

"Things most exciting about in the industry, and what do you think needs to be unlearned? I’ve noticed both individuals and organizations often resist asking for help, preferring to go it alone."

[36:04] - Conclusion and Future Aspirations

"It's been absolutely phenomenal to have you on the show. Thank you for sharing your story so openly and humbly. This is what people love listening to."

Follow Our Guest

LinkedIn Accounts: 

• Kristie Edling-Day: https://www.linkedin.com/in/kristie-edling-day-10690623/  
• Vanguard : https://www.linkedin.com/company/vanguard/ 
• LPL Financial : https://www.linkedin.com/company/lpl-financial/ 

Websites:   

• Vanguard : https://investor.vanguard.com/corporate-portal 

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook 

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly 
• Personal site: https://barryoreilly.com 
• Facebook: https://www.facebook.com/barryoreillyauthor/ 
• Twitter: https://x.com/barryoreilly 
• Instagram: https://www.instagram.com/barryoreilly/ 
• Email: [email protected]

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.

• 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.

• 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 innovations.

Prepare for an insightful conversation with Crystal Gonzalez on Bringing fresh ideas to startup strategies and cultivating a culture of innovation and strategic growth.

[00:35] - Episode Introduction

"In the Philippines, there are 120,000 reported scammers in real estate. This is why, even with a legitimate broker, I felt unease and anxiety until I received the keys to my house."

[01:18] - Guest Introduction: Crystal Lee Gonzalez

"Welcome to the Unlearn Podcast. Today, I'm honored to host Crystal Gonzalez, a leader in strategy and growth who has developed and scaled renowned brands across Southeast Asia."

[03:03] - Viber's Launch Story

"It started when I met Talmon, the founder. My first question was simple: Why are you in the Philippines?"

[07:50] - Nurturing Empathy and Innovation

"Okay. So interesting fact. I promise you this is connected to my answer. So my dad and actually my sister, now my younger sister, they're both psychiatrists."

[16:15] - The Role of Relatability in Product Adoption

"When we added more words to our copy and analyzed our data, we changed our messages to offer free chat and calls for your family and friends abroad"

[26:08] - Discussion on Market Needs and Solution Development

"I kid you not, my earliest memories involve playing role-playing games with my childhood friends where I was signing checks."

[31:27] - Vision for a Seamless Real Estate Experience

"I've always promoted and highlighted issues, even if I wasn’t the founder or creator."

[42:11] - Building Trust in Philippine Real Estate: A Digital Solution

"I didn’t feel safe. Despite dealing with legitimate brokers, the anxiety of 120,000 reported real estate scammers in the Philippines lingered until I held the keys. I kept wondering.why hasn’t this been solved yet?"

[53:51] - Conclusion and Future Aspirations

"Just the way you discuss this issue, your previous achievements, and the team you are building indicate you're set to do something truly amazing."

Follow Our Guest

LinkedIn Accounts: 

• Crystal Lee Gonzalez: https://www.linkedin.com/in/crystalleegonzalez/ 
• NoneAway : https://www.linkedin.com/company/noneaway/ 
• PICK.A.ROO:  https://www.linkedin.com/company/pickaroo/ 
• Canva : https://www.linkedin.com/company/canva/ 
• Honestbee: https://www.linkedin.com/company/honestbee/ 
• Viber: https://www.linkedin.com/company/rakuten-viber/ 
• Tribal World : https://www.linkedin.com/company/tribal-worldwide/ 
• Lazada: https://www.linkedin.com/company/lazada/ 
• Yahoo: https://www.linkedin.com/company/yahoo/ 

Websites:   

• NoneAway: https://noneaway.com/ 
• PICK.A.ROO: https://pickaroo.com/ 
• Canva: https://www.canva.com/ 
• Honestbee: https://www.honestbee.com/ 
• Viber:https://www.forbusiness.viber.com/
• Lazada : https://group.lazada.com/
• Yahoo: https://www.yahooinc.com/ 

_________________________________ 

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook 

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly 
• Personal site: https://barryoreilly.com 
• Facebook: https://www.facebook.com/barryoreillyauthor/ 
• Twitter: https://x.com/barryoreilly 
• Instagram: https://www.instagram.com/barryoreilly/ 

Email: [email protected]

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. 

• 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.

• 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.

[00:33] -Episode Introduction

"One of the trends that we're seeing in product management is this rise of a super IC. People are able to do a whole lot more because of AI than they could have done before."

[01:33] - Guest Introduction

"Today, we’re joined by Diana Stepner, an expert in product management and people-centered leadership. Diana has built leading global product teams at companies like Product Gold, Monster, Salesforce, and Razorfish."

[03:08] - Shift from Project to Product Management

"People kept saying, 'Oh, you're a project manager.' And I'm like, 'No, I'm not a project manager. I am a product manager.' Over time, people began to realize that it actually was a skill or an expertise."

[10:44] - The Role of Collaboration in Product Management (corrected from 10:49)

"You need all of those instruments to come together to really make the music sing, and companies still don't realize that."

[16:08] - The Rise of Super ICs

"You're having these people be able to go much farther down the development path than what they did previously. And I think that's fascinating because it makes total sense."

[19:18] - The Evolution of the Mini-CEO & One-Person Unicorns

"For me, it feels like it's the incarnation of the mini-CEO. Now there's this billion-dollar unicorn narrative where one person is expected to do everything with AI."

[27:00] - The Role of Asynchronous Communication & AI in Workflow Efficiency

"It's funny, sometimes people get freaked out when I summarize a meeting in three minutes and email them key points before they've even left the call!"

[30:48] - The Future of Product Management

"I believe we need to evolve, but that also means we need to welcome in the next generation who bring their own unique perspectives."

[35:33] - Conclusion and Next-Gen Product Management Book Promotion

"My book, Next Gen Product Management, is for those who want to future-proof their careers and thrive in this evolving industry."

Follow Our Guest

LinkedIn Accounts: 

• Diana Stepner: https://www.linkedin.com/in/dianas/ 
• Product Gold : https://www.linkedin.com/company/productgold/ 
• Monster: https://www.linkedin.com/company/monster/ 
• KAYAK: https://www.linkedin.com/company/kayak/ 
• Salesforce: https://www.linkedin.com/company/salesforce/ 
• RazorFish: https://www.linkedin.com/company/razorfish/ 
• Pearson: https://www.linkedin.com/company/pearson/ 

Websites:   

• Personal Website: https://www.dianastepner.com 
• Product Gold: https://www.productgold.com/ 
• Monster: https://www.monster.com/  
• KAYAK: https://www.kayak.com/ 
• Saleforce: https://www.salesforce.com/ap/ 
• RazorFish: https://www.razorfish.com/ 
• Pearson: https://www.pearson.com/ 
• Get your copy of Next-Gen Product Management today! Order now at https://www.nextgenproductmanagement.com/ 

_________________________________ 

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook 

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly 
• Personal site: https://barryoreilly.com 
• Facebook: https://www.facebook.com/barryoreillyauthor/ 
• Twitter: https://x.com/barryoreilly 
• Instagram: https://www.instagram.com/barryoreilly/ 
• Email: [email protected]

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 crafting strategies that disrupt the status quo!

Episode Highlights:

00:37 - Introducing Emily Ross

"Emily is a powerhouse in brand strategy, creative leadership, and co-author of Just Evil Enough. She’s reshaping how global brands stand out in noisy markets."

03:15 - Lessons from the Circus The Power of Attention

"I spent years as a fire performer, and it taught me that attention is a superpower. Learning to capture and hold attention is a skill every marketer needs."

05:14 - Subversive Marketing Tactics Explained

"Subversive marketing is about being bold, counterintuitive, and creative. It’s not growth hacking, it’s about playing the long game to stay ahead."

09:47 - Turning Bugs Into Features

"The famous Space Invaders bug is a perfect example of how flaws can create differentiation. As the game progressed, it got faster, making it more exciting."

15:10 - The Product-Market Fit Myth

"Product-market fit isn’t real, it’s actually product-medium-market fit. Success lies in how you connect your product to the audience through the right medium."

20:33 - Zero-Day Exploits and Subversive Marketing

“We call those zero day exploits. So in cybersecurity, a zero day hack is one that is a kind of a finite hack."

22:42 - Underdog Success Using Unconventional Tactics

"When smaller forces use unconventional tactics, they can flip the odds. It’s how underdogs win in both marketing and warfare."

29:36 - The Recon Framework and Attention Economy

"One of the most practical pieces of the book is the recon canvas. We are drowning in noise, and Herbert Simon coined the term ‘attention economy’, where the thing in shortest supply becomes the currency of the day."

31:28 - Just Evil Enough: Unexpected Validation

"When I pitched the idea of Just Evil Enough sitting beside Alchemy on the shelf, I never imagined Rory Sutherland would not only read the book but offer such high praise. It was an amazing moment of recognition."

Follow Our Guest

LinkedIn Accounts: 

• Emily Ross: www.linkedin.com/in/emilyrossonline/ 
• Twitter: www.linkedin.com/company/x-corp/ 
• Resonance Festival (Resonance-Lough Derg): www.linkedin.com/company/resonance-loughderg/ 
• SXSW: www.linkedin.com/company/sxsw/ 

Websites:   

• Twitter: https://x.com/ 
• Resonance Festival (Resonance-Lough Derg): www.resonance-loughderg.com/ 
• SXSW: www.sxsw.com/ 
• Pre-order the First Edition Hardback of Just Evil Enough today at www.justevilenough.com/ 

_________________________________ 

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook 

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly 
• Personal site: https://barryoreilly.com 
• Facebook: https://www.facebook.com/barryoreillyauthor/ 
• Twitter: https://x.com/barryoreilly 
• Instagram: https://www.instagram.com/barryoreilly/ 
• Email: [email protected]

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.

• 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.

• 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 for a thought-provoking conversation with John Cutler on embracing complexity, fostering innovation, and mastering the art of unlearning!

00:36 - Episode Introduction

"I don't think we need a product manager for every 4 to 7 people. A software as a service company is much more of a service ecology." 

01:15 - Introducing John Cutler

"John is one of the most insightful voices in product management, with a career spanning roles at Toast, Amplitude, and beyond."

03:46 - Discovering the "Beautiful Mess" of Product

"I’ve always been fascinated by the overlaps—where product, UX, and strategy collide in unpredictable ways."

11:27 - The Importance of Writing and Sharing Ideas

"I realized that writing wasn’t just for others—it was for me to process and refine my thinking."

15:59 - Finding Your Path Through Experimentation

"Everybody finds their way if you're willing to experiment and try. It's like software—the rate of iteration and the velocity of creation allow you to refine and improve over time."

33:06 - Lessons in Unlearning

"It’s not just about adopting new practices; it’s about letting go of the ones that no longer serve the team or the context."

40:59 - What Excites John About the Future of the Industry

"The future of product management lies in embracing complexity and experimenting with new ways to scale and deliver value."

Follow Our Guest

LinkedIn Accounts: 

• John Cutler: www.linkedin.com/in/johnpcutler/ 
• Dotwork: www.linkedin.com/company/dotworklabs/ 
• Toast: www.linkedin.com/company/toast-inc/ 
• Amplitude: www.linkedin.com/company/amplitude-analytics/ 
• Zendesk: www.linkedin.com/company/zendesk/ 
• Pendo: www.linkedin.com/company/pendo-io/ 

Websites:   

• Dotwork: www.dotwork.com/ 
• Toast: www.pos.toasttab.com/ 
• Amplitude: www.amplitude.com/  
• Zendesk: www.zendesk.com/ 
• Pendo: www.pendo.io/ 

_________________________________ 

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook 

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly 
• Personal site: https://barryoreilly.com 
• Facebook: https://www.facebook.com/barryoreillyauthor/ 
• Twitter: https://x.com/barryoreilly 
• Instagram: https://www.instagram.com/barryoreilly/
• Email: [email protected]

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.

• 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.

• 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!

• 00:36 - Episode Introduction
• "We're always going to have new technologies. But that doesn't negate the fact that you still have to master the fundamentals."
• 01: 03 - Barry introduces Lee Vorthman as a seasoned cybersecurity expert and VP of Strategic Security Initiatives at Oracle.
• 02:27 - Personal Background and Military Influence
• "I grew up in a military household and started in technology before joining the military."
• 05:33 - Evolution of Security Leadership
• "Security leadership now touches every aspect of a business, requiring a broad understanding beyond just technology."
• 11:15 - Navigating Accountability vs. Ownership
• "In the civilian world, I’m accountable for risks I don’t always own, which requires building alliances."
• 15:05 - Techniques for Overcoming Resistance
• "Two techniques I use to convince people: the switcheroo and Jedi mind trick for breaking resistance."
• 22:35 - Challenges in the Security Industry
• "The industry tends to chase shiny new technologies while neglecting critical fundamentals."
• 28:06 - Excitement About Emerging Technologies
• “I love when new technology comes out because it allows security people to put their hats on to make it  safe.”
• 30:25 - Closing Remarks
• "It’s been an amazing journey, and I appreciate sharing these stories on the podcast."

Follow Our Guest

LinkedIn Accounts: 

• Lee Vorthman: https://www.linkedin.com/in/leevorthman/
• Oracle:https://www.linkedin.com/company/oracle/
• US Navy: https://www.linkedin.com/company/us-navy/
• HMG Strategy: https://www.linkedin.com/company/hmg-strategy-llc/
• Phoenix Security: https://www.linkedin.com/company/phoenixsecuritycloud/
• Evanta, a Gartner Company: https://www.linkedin.com/company/evanta/

Websites:   

• Lee Vorthman (Blog): https://blog.370security.com/author/lee1fbb48c29971/
• Oracle: https://www.oracle.com/
• US Navy: https://www.navy.mil/
• HMG Strategy: https://hmgstrategy.com/
• Phoenix Security: https://phoenix.security/
• Evanta, a Gartner Company: https://www.evanta.com/

_________________________________ 

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook 

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly 
• Personal site: https://barryoreilly.com 
• Facebook: https://www.facebook.com/barryoreillyauthor/ 
• Twitter: https://x.com/barryoreilly 
• Instagram: https://www.instagram.com/barryoreilly/ 
• Email: [email protected]

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. 

• 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.  

• 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!

• 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 Filipova

‘’Ani Filipova, an inspiring leader whose journey spans across continents, industries, and perspectives’’

• 03:10 - Growing Up Behind the Iron Curtain

"I saw the world through books... Pippi Longstocking inspired me to dream about traveling to far-off places."

• 12:59 - Leadership Across Cultures

"You can’t pretend to care about people’s aspirations—you have to truly understand what drives them to build trust and alignment."

• 25:01 - Overcoming Personal Challenges in Leadership

"I realized I needed to stop taking everything personally—it was a turning point that helped me approach challenges more confidently." 

• 27:56 - Speaking Up in Leadership Meetings

"I remember waiting for the right moment to contribute, and when I did, the adrenaline rush was overwhelming, but it was worth it."

• 37:44 - Adapting Banking to the Digital Era

"Transitioning from three-day payments to three-second transactions required rethinking systems, processes, and customer expectations."

• 42:11 - The Challenge of Unlearning

"To succeed in today’s fast-changing world, leaders must unlearn old habits and embrace continuous listening and collaboration."

• 45:33 - Closing Reflections

"It’s about reinvention—helping others see their own potential and embrace transformation in their careers."

Follow Our Guest

LinkedIn Accounts: 

• Ani Filipova:  www.linkedin.com/in/anifilipova 
• Citibank: www.linkedin.com/company/citi 
• Change Advisory: www.linkedin.com/company/the-change-advisory 
• AdVentura Works SA.: www.linkedin.com/company/adventura-works 

Websites:   

• Ani Filipova - Change Advisory: www.anifilipova.me
• Citibank: www.citigroup.com/global 
• AdVentura Works SA.: www.adventura.works 

_________________________________ 

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook 

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly 
• Personal site: https://barryoreilly.com 
• Facebook: https://www.facebook.com/barryoreillyauthor/ 
• Twitter: https://x.com/barryoreilly 
• Instagram: https://www.instagram.com/barryoreilly/ 
• Email: [email protected]

Welcome to the UNLEARN Podcast! Today, we’re joined by a true pioneer in digital transformation and customer strategy, David C. Edelman. With over three decades at the forefront of marketing and digital transformation, David most recently served as Chief Marketing Officer at Aetna/CVS, where he led transformative shifts in customer engagement. Before that, he co-led McKinsey’s Global Digital Marketing and Sales Practice and held key leadership roles at Digitas and Boston Consulting Group (BCG), advising top executives worldwide.

Now, David is bringing his expertise to Harvard Business School, where he shapes the next generation of leaders and advises CXOs on driving digital agility and building resilient teams. In this episode, he shares insights from his latest book, Personalized: Customer Strategy in the Age of AI.

We’ll explore the different types of AI, where and how to use them, and the evolving role of AI across the C-suite. Get ready for an enlightening conversation with David Edelman on the future of customer strategy in the age of AI. 

• Personalized Connections with AI: David’s “five promises” framework—Empower, Know, Reach, Show, Delight—guides personalized customer experiences.
• AI Beyond Marketing: Personalization extends beyond marketing into a holistic, C-suite-level strategy.
• Data to Value: Examples from Aetna using data to simplify interactions and deliver targeted recommendations.
• Balancing Innovation and Trust: David stresses trust in AI, focusing on data privacy and ethical personalization.

• Promise and Pitfalls of AI: Emerging AI tools make data integration accessible, helping smaller companies compete with industry giants.
• Managing Expectations: The importance of transparency and data use comfort in creating personalized, non-intrusive customer experiences.
• Unlearning Old Mindsets: David encourages that leaders must shift from traditional tactics to a customer-centric, AI-driven approach.

• 00:00 - Episode Introduction

"If you’re trying to connect with customers using personalization, there are essentially five promises that you’re making to them."

• 01:35 - Introduction to the Episode: Barry introduces David Edelman, a veteran in digital transformation and customer strategy.

“David has spent over three decades at the cutting edge of marketing and digital transformation.”

• 03:06 - Early Influences: Creativity and Leadership in Marketing

“I became the music director of my high school show from just simply being a saxophone player.”

• 08:33 - From Marketing to AI-driven Strategy

“The thing I had to unlearn is that it’s not just about marketing... it’s about strategy and customer experience.”

• 10:03 - Using AI for Personalization: Shopify and Brinks Case Studies

“So Shopify, who has a free trial and then offers to convert people to paid subscriptions... it’s over 500 combinations.”

• 19:26 - Educational Personalization: The Aetna Video Initiative

“People don’t understand it, they make mistakes... so we found a provider that could create personalized videos.”

• 25:25 - The Five Promises of Customer Strategy

“Empower me, know me, reach me, show me, delight me.” 

• 37:59 - Closing Thoughts and The Future of AI in Personalization

“We’ve got to show good things, good experiences that are happening in ways that are trustful and appropriate.”

Follow Our Guest

LinkedIn Accounts: 

• David C. Edelman: https://www.linkedin.com/in/daveedelman/ 
• Aetna: https://www.linkedin.com/company/aetna/ 
• McKinsey: https://www.linkedin.com/company/mckinsey/ 
• BCG: https://www.linkedin.com/company/boston-consulting-group/ 
• Digitas: https://www.linkedin.com/company/digitas-north-america/ 
• Harvard Business School: https://www.linkedin.com/school/harvard-business-school/ 

Websites:   

• Aetna:  https://www.aetnacvshealth.com/ 
• McKinsey: https://www.mckinsey.com/ 
• BCG: https://www.bcg.com/ 
• Digitas: https://digitz-digitas.com/ 
• Harvard Business School: https://www.hbs.edu/ 

_________________________________ 

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook 

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly 
• Personal site: https://barryoreilly.com 
• Facebook: https://www.facebook.com/barryoreillyauthor/ 
• Twitter: https://x.com/barryoreilly 
• Instagram: https://www.instagram.com/barryoreilly/ 
• Email: [email protected]