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]

Mastering venture capital and ethical growth is essential for startup success. Today’s guest, Andy Budd, shares insights from his journey as Founder and CEO of Clearleft, Venture Partner at SeedCamp, and Founding Member of Adobe’s Design Circle. Andy has evolved from a designer to an investor and advisor, bringing a focus on ethical growth practices and high-impact startup development.

As the author of The Growth Equation, Andy draws on over 20 years of experience to help companies achieve product-market fit and sustainable growth. His work with SeedCamp and other startups focuses on behavioral science and ethical growth strategies to build resilient, user-centered businesses.

In this episode, host Barry O'Reilly explores Andy’s approach to venture capital, leadership, and how his design roots influence his support for founders.

• The Transition from Design to Venture Capital: Andy shares his journey from designer to venture capital partner, highlighting the unique insights that his design background brings to his work with startups.

• The Importance of Humility in Leadership: Andy emphasizes the value of hiring individuals who excel in areas beyond one’s own expertise, fostering a team culture of shared growth and continuous improvement.

• Supporting Startups Through Challenges: Known for working closely with startups facing obstacles, Andy describes how his collaborative approach helps companies pivot, adapt, and ultimately thrive.

• Ethical Growth Over “Growth Hacking”: Andy discusses the significance of ethical growth practices, contrasting them with conventional “growth hacking,” and focusing on strategies that promote sustainable and user-centered growth.

• The Influence of Behavioral Science in Product Development: Andy explains how understanding human behavior enhances product design and growth, encouraging founders to integrate behavioral science for more meaningful user engagement.

• The Role of Patience and Empathy in VC: Andy reflects on his approach to venture capital, prioritizing empathy and patience with founders to cultivate trust and strong, lasting partnerships.

• The Changing Landscape of Startup Investment: Andy shares his views on how venture capital is evolving, especially as design-thinking and user experience become increasingly vital for high-growth startups.

• 0:39 - Introduction to the Episode: Barry introduces Andy Budd, Startup Advisor, Investor, and Coach.

“Andy has extensive experience in design and startup advisory.”

• 03:31 - Transition from Design to Venture Capital

"I've always been inspired by others...there was an agency that really inspired Clearleft back in the day called Adaptive Path."​

• 06:58 - Unlearning Practitioner to Leader

“The main thing I had to unlearn was moving from a practitioner to a leader, where you need to let go and trust others.”

• 15:56 - Emphasis on Character and Integrity in VC

“If you're rude to the driver or the person at reception, it shows a lot about your character.”

• 24:34 - The Growth Equation: Helping Founders Find Product-Market Fit

"One of my reviewers said it’s like having a pocket coach. Why spend thousands on an online course when you can get the framework in a book?"​

• 33:32 - Role of Behavioral Science in Growth

"I'd demonstrate it with an example. So an example is economics... economists thought we were rational actors, that we’d make logical decisions about the future, like saving for retirement. But people tend to choose instant gratification, which is where behavioral economics comes in."​

• 37:26 - The Ethical Approach to Product-Led Growth

“Product-led growth has been one of the biggest trends in the last few years, around how we can use our products and the way we design them to attract more users and drive engagement.”

• 45:13 - Andy’s Thoughts on Growth Hacking vs. Ethical Growth

"A big part of my book is actually about how you look at growth, but in a more moral, reasonable, and acceptable way. I hate the idea of growth hacking."

• 46:42 - Wrap-up & Final Thoughts: Barry and Andy discuss the ongoing importance of community and knowledge-sharing.

"Everyone, get yourself a copy of The Growth Equation!”

Follow Our Guest

LinkedIn Accounts:  Andy Budd, Clearleft, Adobe, Seedcamp 

Websites:  Andy Budd - Personal Site, Clearleft, Adobe, Seedcamp 

_________________________________

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]

Mastering executive search and building lasting business relationships are essential for successful transformations. Today’s guest, Michael A. Morell, shares insights from his journey at Riviera Partners, a top executive search firm, and as a former member of the Technology Advisory Board at Bridgewater Associates.

Michael A. Morell is the Founder and Managing Partner of Riviera Partners, with over two decades of experience in executive search. After starting his career in technology, a poor interview experience sparked his idea to create a better approach to recruiting. Today, Michael and his team help tech companies make high-stakes hires, transforming how top talent is identified and placed in Silicon Valley and beyond. Riviera Partners continues to deliver executive search solutions for some of the most innovative companies around the world.

In this episode, host Barry O’Reilly explores Michael’s approach to executive recruitment, the importance of patience in relationship-building, and how Riviera Partners leverages technology to deliver consistent, high-quality results.

• The Power of Patience in Relationship Building: Michael shares why patience is critical in executive search and enterprise sales, where building strong, lasting relationships can lead to long-term success.

• Consistent Delivery of High-Quality Experiences: Michael emphasizes how consistent, positive experiences set Riviera Partners apart, explaining how a focus on quality service helped them build a reputable brand in executive recruitment.

• The Role of a Clear Vision: Michael discusses the importance of a simple and clear company mission that empowers employees to make decisions aligned with the company’s values.

• Adapting to Technological Advances: As technology has evolved, so has Riviera Partners. Michael shares how the firm leverages data and technology to enhance the recruitment process and provide better insights for clients.

• Learning Through Experience: Michael’s shift from technology to recruitment highlights the value of diverse experiences and risk-taking in meaningful work, as he reflects on the challenges of building Riviera Partners.

• The Changing Recruitment Landscape: Michael discusses how tools like LinkedIn have democratized recruitment and shares his excitement about AI and machine learning’s potential to transform executive search.

• The Future of Workplace Flexibility: Michael reflects on the pandemic’s impact on remote work, emphasizing the balance between flexible environments and the importance of in-person interactions for leadership roles.

• 00:40 - Introduction to the Episode: Barry introduces Michael A. Morell, Founder of Riviera Partners

“Michael has over two decades of experience in executive search.”

• 03:19 - The career transition into recruitment

“About 3 or 4 years into that, I got a random call from a recruiter who said, 'Hey, we’d love to grab coffee.' Long story short, I had coffee, she showed me a couple of opportunities—this was around the 2000 timeframe—and it was just the most awful experience I’ve ever had."

• 06:34 - Michael applies his long-term sales experience to relationship-building in executive search

“I had the patience to develop these relationships, but I thought, it couldn't be that complicated.”

• 15:27 - Delivering Consistent, High-Quality Experiences

“For us, it was really about one thing: how do we consistently deliver a great experience?”

• 24:17 - Navigating the shifts in recruitment technology

“The Rolodex became LinkedIn, and suddenly all the information was democratized. You can start to anticipate changes, but fundamentally, every client and every candidate is unique.”

• 34:02 - Embracing workplace flexibility and hybrid models

“We went from everyone needing to be on-site to realizing remote could work. Now, we’ve evolved to a hybrid model, balancing in-person and remote roles.”

• 36:59 - The future of recruitment with AI and machine learning

“I’m excited to see how AI can enhance our processes, from finding insights in data to improving client and candidate experiences.”

• LinkedIn: Michael A. Morell, Riviera Partners,Bridgewater Associates.
• Websites:  Riviera Partners, Bridgewater Associates

_________________________________

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Driving innovation in technology and business transformation demands visionary leadership, seamless integration of business and tech strategies, and a willingness to take risks. Today's guest, David Gledhill, exemplifies these qualities as he shares his experience leading DBS Bank through a remarkable digital transformation and beyond.

David Gledhill is a seasoned technologist and business leader. As the former Group Chief Information Officer at DBS Bank for over 11 years, he spearheaded the bank’s technology and transformation efforts, building a high-performance culture and integrating technology into the core of the business strategy. Under his leadership, DBS achieved global recognition for its digital transformation, and David’s journey has been featured in Harvard Business Review as one of the top global transformations. After his time at DBS, David held a senior role at Lloyds Banking Group, further enhancing his expertise in large-scale transformation. He is now a non-executive director at companies like Singapore Airlines and serves as a senior advisor to McKinsey & Company.

In this episode, host Barry O'Reilly invites David to discuss his leadership journey, from reshaping the technology at DBS to embracing a digital-first strategy. David offers insights on making tough decisions, aligning business with technology, and leading organizations through massive change.

• Technology as a Strategic Driver: David emphasizes the shift from viewing technology as a support function to recognizing it as a core driver of business strategy. He explains how leading with a digital-first mindset can unlock new growth opportunities.

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• Bold Decision-Making in Leadership: David shares the importance of making tough decisions early in leadership roles. He describes how scrapping failing projects and resetting strategies allowed DBS to pivot successfully.

• Building a High-Performance Culture: David highlights the significance of creating a culture where business and technology teams share accountability. His “two in a box” leadership model at DBS encouraged joint ownership of goals and outcomes.

• Learning from Tech Giants: Drawing inspiration from companies like Google and Amazon, David discusses how studying these tech giants helped DBS adopt cutting-edge practices in cloud computing, data analytics, and agile development, setting them apart in the banking industry.

• Fostering a Culture of Storytelling: David highlights the importance of storytelling in driving organizational change. At DBS, he brought in a journalist to craft compelling narratives around early successes, which helped engage teams and build momentum for transformation.

• From Technologist to Strategic Leader: David’s transition from a technical expert to a strategic business leader is a testament to the evolution required in leadership roles. He reflects on how moving from deep technical work to overseeing large-scale business transformation broadened his leadership perspective.

• The Role of Technology in the Future of Banking: David reflects on the future of the financial industry, noting that technology will continue to play a critical role in driving innovation and improving customer experiences. He emphasizes the need for continuous adaptation to stay competitive in the fast-changing digital landscape.

• 00:00 - Introduction to the episode

Barry introduces David Gledhill, highlighting his role as former Group CIO of DBS Bank and his contributions to the company’s digital transformation.

• 04:12 - David on his early career and technical roots

"I started off even when I was 11 or 12, building stuff with electronics and did computing electronics at university."

• 05:13 - The turning point of joining DBS

"When my career progressed, I became more of an exec... And then back in 2008, an opportunity came to join DBS Bank and become a CIO again, and get really back into tech."

• 12:21 - Scrapping the core banking system

"They’d spent like $300 million of a $200 million budget. And the estimate was this is going to take another five years and another billion dollars to complete."

• 12:36 - Rebuilding the technology strategy at DBS

"I had to basically scrap that whole program and restart... it was a total reset of strategy, roadmap, people, everything from scratch."

• 17:31 - Creating success with the ‘buy, sell, hold’ strategy

"We came up with this what we call the buy, sell, hold diagram... I love the system, and do more with it. Sell it to get rid of it. Hold is kind of meh but it'll keep going for now."

• 24:21 - The platform model and joint leadership

"We created a ‘two in a box’ leadership model, where a business leader and a tech leader had joint KPIs... business KPIs, customer service levels, tech modernization – everything."

• 31:47 - The ‘Gandalf’ moment and digital-first strategy

"We looked at Google, Amazon, Netflix, Apple, LinkedIn, Facebook, and I came up with this idea of what if we were the D in Gandalf?"

• 37:33 - Lessons for the future and technology’s role in business growth

"It’s hugely satisfying when you see that happen... they’re doing some super risky things, which may or may not play out, but that’s great fun to be part of."

Follow Our Guest

• LinkedIn: David Gledhill
• Website: DBS Bank, Lloyds Banking Group, Singapore Airlines, McKinsey & Company

_________________________________

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/46uZ7q0

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• LinkedIn: https://www.linkedin.com/in/barryoreilly
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Leadership in technology and operations requires a strategic focus on scaling businesses, empowering teams, and driving innovation. Today's guest, Richard Lennox, exemplifies these qualities as he shares his journey from leading Skyscanner through rapid growth to scaling healthcare innovation at Current Health.

Richard Lennox is an experienced technologist and business leader. As Senior Director at Skyscanner, he led the company’s engineering and operations teams through a pivotal period of scaling, focusing on high-performance teams and continuous delivery. After Skyscanner’s successful exit, Richard transitioned to COO at Current Health, where he helped scale the business, focusing on home healthcare delivery through technology. His leadership experience spans multiple industries, making him a valuable mentor and guide for those navigating startup growth and innovation.

In this episode, host Barry O'Reilly invites Richard to discuss his journey, from his early days at Skyscanner to his role at Current Health. Richard provides insights into scaling startups, the importance of data-driven decision-making, and the operational challenges of growing high-performance teams.

Key Takeaways:

• Customer Value at the Core: Richard emphasizes the importance of focusing on delivering customer value in all areas of business, whether in technology or healthcare. Customer needs should drive product development and operational strategies.

• Scaling High-Performance Teams: Richard discusses how growing from small teams to larger, cross-functional squads allowed for better alignment with business goals at Skyscanner. He shares the challenges and successes of implementing a squad model to foster accountability and autonomy within teams.

• Rapid Decision-Making: Making fast decisions and knowing when to reverse them is critical to maintaining agility in a growing company. Richard stresses the importance of empowering teams to make decisions based on data and customer outcomes.

• Holistic Leadership: Transitioning from a function-specific mindset to a broader business operations perspective allowed Richard to lead with a focus on scaling the entire organization, not just the technology function.

Additional Insights:

• Empowering Teams through Data: Richard highlights the value of real-time data in empowering teams to make informed decisions. At Skyscanner, instrumentation of key metrics allowed teams to focus on customer outcomes and make data-driven decisions at scale.

• Transitioning from Tech Leadership to Business Leadership: Richard’s journey from Senior Director at Skyscanner to COO at Current Health showcases the evolution from technical leadership to overseeing broader business operations. He reflects on the mindset shift required to focus on business outcomes over functional expertise.

• The Future of Healthcare at Home: Richard shares insights into the growing importance of delivering healthcare in the home environment, using technology to monitor patients remotely and operationalizing care at home programs. This innovation is essential for reducing the burden on hospitals and improving patient outcomes.

Episode Highlights:

• 00:00 - Download free innovation map
• 00:41 - Introduction to Richard Lennox
• 03:36 - Early career and decision to join startups

"I got really lucky early on in my career, joining an early startup, which shaped my thinking about delivering value to customers."

• 07:48 - Learning from setbacks and focus on customer value

"There has to be a better way to deliver value consistently without causing setbacks for the business."

• 14:48 - Rapid decision-making and empowering teams

" I think the tricks for scaling are rapid decision making and how you invert the decision when you make it wrong. The more you hang on to a wrong decision, the worse the impact is."

• 24:21 - Richard’s Transition to COO at Current Health and Leading Healthcare Innovation

"Current Health provides a platform to enable care to be delivered at home."

• 32:12 - Future of Healthcare at Home and Operational Excellence

"Our job was to operationalize care at home programs, and that required a whole new set of tools and thinking."

• 38:06 -  Wrap Up

Follow Our Guest

• LinkedIn:  https://www.linkedin.com/in/rlennox/
• Website:  https://www.currenthealth.com/
•                 https://www.linkedin.com/company/skyscanner/

_________________________________

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.

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