Unlearn

In this episode of The Unlearn Podcast, Barry O’Reilly is joined by Steve Elliott, a serial entrepreneur, product leader, and investor with two decades of experience advising high-growth companies. Steve is the founder of Dotwork, an AI-driven platform that connects strategy to execution, and co-founder of The Uncertainty Project, a community for product leaders focused on better decision-making.

He previously served as Head of Prod...

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 transformation journey—with curiosi...

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 teams worked using design thinking ...

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 their strategy through one often-overloo...

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 explore how your brain interprets socia...

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 organizations across Europe and Asia ...

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 capital with causes that matter.

In this...

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 communities, and transform the way we ...

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 Sound of Freedom: True Stories Tha...

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 cultivating startup communities by putting peo...

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 organizational design. He’s held executiv...

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 behavior. He co-authored Just Evil Enough: Th...

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 Container Solutions, a consultancy helping o...

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 projects and planning weekends with his ...

Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast.

Contact here: https://bit.ly/contact-barryoreilly

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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, aerospace and electrical engineer, and now ...

Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast.

Contact here: https://bit.ly/contact-barryoreilly

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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 challenges have shaped his journey of learning...

Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast.

Contact here: https://bit.ly/contact-barryoreilly

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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 organizations, governments, and communities ...

Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast.

Contact here: https://bit.ly/contact-barryoreilly

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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 produc...

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 perform...