Unlearn

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...

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 Mar...

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...

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...

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...

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...

Leadership in government and technology requires not only innovative thinking but also a deep commitment to public service. Today's guest, Paola Santana , exemplifies these qualities as she shares her journey from law and politics to becoming a trailblazer in government technology. Paola Santana is a lawyer, public procurement expert, and serial tech entrepreneur who is revolutionizing government...

Leadership in digital ecosystems requires a commitment to safety, trust, and ethical practices. Our guest today, Dave Byrne , founder of Trust Raise and a member of the Irish Digital Board, shares his journey from major tech giants to establishing a company dedicated to improving the integrity of digital platforms. Dave Byrne has had an illustrious career, holding significant positions at Google,...

Cybersecurity is an ever-evolving field that requires continuous learning, adaptability, and a deep understanding of both the technological landscape and human behavior. Today’s guest, Dave Mahon , a seasoned cybersecurity expert with extensive experience in both the private and public sectors, shares his journey from the FBI to leading global cybersecurity efforts in the corporate world. Dave Mah...