Unlearn

In this episode of the Unlearn Podcast, I sit down with Cass Pratt, Chief Human Resources Officer at Progyny, to explore how HR is evolving into a design discipline that blends human connection with AI-powered productivity. From building bots to boost employee experience to reshaping how we think about roles in an automated world, Cass shares an honest look at how she’s bringing people along on a...

When most leaders think about transformation, they reach for tools and tactics. But real, lasting change doesn’t start with new methods—it starts with culture. In this episode, I sit down with Phil Gilbert, the former General Manager of Design at IBM, who led one of the boldest reinventions in corporate history. After selling his third startup to IBM in 2010, Phil was asked to transform how IBM’s...

When it comes to product positioning, clarity isn’t just a communication tool—it’s a strategic advantage. In this episode, I sit down with Anthony Pierri, co-founder of FletchPMM , a product marketing consultancy that’s helped over 400 B2B software startups discover and sharpen their positioning. We explore how founders can unlearn generic marketing advice, clarify their message, and activate thei...

In today’s hyper-connected world, many of us are experiencing a paradox—more digital interactions, but deeper loneliness. In this episode of Unlearn , I sit down with Dr. Ben Rein, neuroscientist and author of Why Brains Need Friends , to unpack why human connection isn’t just emotional—it’s biological. From the neuroscience of loneliness to surprising acts of generosity in mice and minnows, we ex...

What happens when you stop treating HR as a back-office function and start designing it as a competitive advantage? Theresa Cantwell, Strategic HR Consultant and Director at GSD HR Consulting, believes scaling a company shouldn't mean burning out your team—or yourself. With nearly two decades leading people strategy at companies like Microsoft, ThoughtWorks, and Equal Experts, Theresa has helped o...

What happens when you stop chasing returns and start investing in purpose? Ron Diamond, Founder and Chairman of Diamond Wealth, believes the future of finance isn’t just about building wealth—it’s about what that wealth can do. As a trusted advisor to over 100 family offices ranging from $250 million to $30 billion, Ron has spent more than two decades helping ultra-wealthy families align their cap...

What if networking wasn’t about schmoozing but about being seen? David Homan joins me to unlearn the myths of traditional networking and share how vulnerability, deep listening, and small group connection can foster truly meaningful relationships. As a master connector, classical composer, and co-author of Orchestrating Connection , David breaks down the silent skills that build trust, activate co...

Paul Hutchinson’s life story reads like a thriller, but his mission is deeply real and urgent. Once a multi-billion dollar fund manager, Paul transformed his life to become an undercover operative, leading more than 70 rescue missions across 15 countries to free thousands of children trapped in sex trafficking. He is the true-life inspiration behind the Sound of Freedom movie and the author of The...

What if generosity—not hustle—is your greatest competitive advantage? Brad Feld—co-founder of Foundry Group, Mobius Venture Capital, and startup accelerator Techstars—joins Barry to explore the transformative philosophy of “Give First,” a mindset that’s reshaped how founders, investors, and mentors build lasting companies and vibrant startup ecosystems. Brad has spent over three decades cultivatin...

What if becoming a better leader meant letting go of being the expert? In this Unlearn episode, I’m joined by David Tuck, Chief Executive of Waracle, for a thoughtful and human-centered conversation on the mindset shifts required to lead high-performing teams in complex, fast-changing environments. David’s leadership journey spans over 15 years of agile transformation, commercial growth, and organ...

What if the biggest risk in your business isn’t building the product but realizing no one wants it? In this Unlearn episode, I’m joined by Alistair Croll , technologist, entrepreneur, and bestselling author of Lean Analytics , for a candid and clever conversation on rethinking product development, marketing, and demand generation. Alistair’s work focuses on data-driven innovation and human behavio...

Today on the Unlearn podcast, we welcome Jamie Dobson , technologist, entrepreneur, and a leader known for building systems that connect innovation with purpose. He joins us to share a deeply reflective journey: spanning childhood curiosity, extreme programming, leadership challenges, and the hard truths of building a company with intention. Jamie Dobson is the co-founder and former CEO of Contain...

Today on the podcast, we welcome Jeremy Shankle, full-stack engineer, AI strategist, and early adopter of automation tools across work and life at Nobody Studios.  With decades of experience in web development, startup leadership, and product strategy, Jeremy shares how going all-in on artificial intelligence has transformed how he works, lives, and thinks. From debugging code to managing pro...

Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast. Contact here: https://bit.ly/contact-barryoreilly ____________________________________________________________ Welcome to UNLEARN, the podcast where we talk about bold ideas, fresh thinking, and the mindset shifts needed for real change. Today, I’m excited to welcome John Avrett , former U.S. diplomat, aero...

Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast. Contact here: https://bit.ly/contact-barryoreilly ____________________________________________________________ Today on the podcast, we welcome Faisal Hoque , author, entrepreneur, and thinker behind Transcend. With over 10 books and years of business leadership, Faisal shares how life, purpose, and challen...

Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast. Contact here: https://bit.ly/contact-barryoreilly ____________________________________________________________ Today on the podcast, we welcome Ja-Naé Duane , systems thinker, innovator, and author of Super Shifts . With over 20 years as a behavioral scientist and 4-time entrepreneur, Ja-Naé has guided orga...

Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast. Contact here: https://bit.ly/contact-barryoreilly ____________________________________________________________ Today on the Unlearn Podcast, I’m thrilled to be joined by Francesca Cortesi, CPO and Founder of Prodotto Collective, a product visionary, transformational leader, and someone who truly understands...

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 compreh...

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 Va...

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 p...

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 , Cheap...

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...

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 impac...

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 defe...

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 Citib...