THE LEARNING LEADER SHOW
Welcome to The Learning Leader Show. My mission is to have deep conversations with the world’s most thoughtful leaders and share their useful life stories and leadership wisdom. I speak with CEOs, Special Forces Operators, Entrepreneurs, Best-Selling Authors, Professional Athletes, and more. Our conversations are open dialogs where my guests share their most valuable experiences and learnings for the benefit of The Learning Leader Show audience. You will find links to each episode and the corresponding show notes at the bottom of this page.
The Learning Leader Show has been listened to by millions of people and was chosen by Apple Podcasts as an “all-time best-seller” in 2020. Forbes called it, “the most dynamic leadership podcast out there.” Inc Magazine said, “It’s one of the five podcasts to make you a smarter leader.”
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Episode List & Show Notes
All episodes are listed below, newest first. Each episode link has show notes with major topics discussed and links to books & other resources mentioned in the episode.
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Episode #659: Derek Sivers – Not Waiting for Permission, Hell Yeah or No, Leadership Lessons From The Dancing Guy, & Why The Standard Pace is for Chumps
Derek Sivers is the founder of CD Baby and author of "Hell Yeah or No" and "Useful Not True." He shared how he graduated from Cal Berkeley in two years instead of four because the "standard pace for chumps" - a lesson that shaped his entire career of institutional skepticism and unconventional [...]
Episode #658: Dave Berke – From Top Gun to Extreme Ownership: Managing Ego, Building Humility, Emotional Detachment, Agile Planning, and Leading Teams Through Chaos
Dave Berke is a retired US Marine Corps Officer, TOPGUN Instructor, and now a leadership instructor and speaker with Echelon Front, where he serves as Chief Development Officer. As a F/A-18 pilot, he deployed twice from the USS John C Stennis in support of combat operations in Iraq and Afghanistan. He spent three [...]
Episode #657: Helen Lewis – Why Genius Is a Myth, Edison Needed Teams, Self-Promoters Are Overrated, Conspiracy Theories, Shakespeare Needed Luck, and How To Build an Excellent Career
Helen Lewis is a staff writer at The Atlantic and author of The Genius Myth: Great Ideas Don't Come from Lone Geniuses. An award-winning journalist, she previously served as deputy editor of the New Statesman. Lewis writes incisively about politics and culture, bringing sharp analysis and wit to complex social debates. Based in [...]
Episode #656: Dakota Meyer – Medal of Honor, The Battle of Ganjgal, Leadership Under Fire, The Loyalty Question, and What America Needs Right Now
Dakota Meyer, a United States Marine Corps veteran and Medal of Honor recipient. At just 21 years old, Dakota's actions during the Battle of Ganjgal in Afghanistan saved many lives when he repeatedly went against his orders and drove into a Taliban ambush zone to rescue trapped soldiers. He became the first living [...]
Episode #655: Morgan Housel – The Simple Formula For Happiness, Betting on Others, Gaining Independence & Purpose, Family Vacation Secrets, The Art of Spending Money, & The Death Bed Lesson Every Leader Needs to Hear
Morgan Housel is the New York Times Bestselling author of The Psychology of Money, Same As Ever, and The Art of Spending Money. His books have sold over nine million copies and have been translated into more than 60 languages. He is a two-time winner of the Best in Business Award from the Society of American [...]
Episode #654: Jake Tapper – The Most Important Leadership Skill, Handling Criticism, Chasing Your Curiosity, Understanding Tradeoffs, Responding to Rejection, and Being So Good They Can’t Ignore You
Jake Tapper is an award-winning broadcaster and chief Washington correspondent, currently anchoring The Lead with Jake Tapper every day on CNN. He’s also the #1 New York Times best-selling author of 7 books, including The Outpost (which was later made into a movie), Original Sin, and most recently Race Against Terror. Watch [...]
Episode #653: Sukhinder Singh Cassidy – Becoming a CEO, Transforming a Company, Earning the Promotion, Knowing Your Non-Negotiables, & Hiring Excellent Leaders
Sukhinder Singh Cassidy is the CEO of Xero. Xero is a cloud-based accounting software designed for small businesses. They did $2.1 billion in revenue last year. Over the past 25 years, Sukhinder has had leadership roles at Google, Amazon, and StubHub. Watch our conversation on YouTube. And SUBSCRIBE! This is brought to [...]
Episode #652: Arthur Brooks – The Power of Teaching, The Arrival Fallacy, The Mad Scientist Profile, Lifting Heavy Weights, & The Two Best Practices To Be Happy
Arthur Brooks is a professor at the Harvard Kennedy School and the Harvard Business School, where he teaches courses on leadership and happiness. He is also a columnist at The Atlantic, where he writes the popular weekly “How to Build a Life” column. He also hosts the evidence-driven podcast, Office Hours with Arthur [...]
Episode #651: Shaka Senghor – From Prison to Purpose: Breaking Mental Barriers, Working with Mentors, and Leading Through Vulnerability (How To Be Free)
Shaka Senghor spent 19 years in prison for killing a man. He’s transformed his life through not making excuses and taking full ownership of his decisions. Now, he’s a New York Times best-selling author who has been called a “soul igniter” by Oprah. His latest book is called How to Be Free: A [...]
Episode #650: Michelle “Mace” Curran – Building a World-Class Team, Running an Excellent Debrief, Rebuilding Trust, Feedback Loops, & How To Turn Fear Into Your Superpower
Michelle “Mace” Curran is a combat veteran, former fighter pilot, and only the second woman in history to fly as the Lead Solo for the Thunderbirds, the U.S. Air Force’s elite demonstration squadron. Now on a new mission, she’s using her story to inspire others. She is the best-selling author of The [...]
Episode #649: Sam Lessin – Type 2 Fun, Voluntary Hardship, Joy as a Competitive Advantage, Long-Term Thinking, & Life Lessons From Dad (Lessin’s Lessons)
Sam Lessin is a Partner at Slow Ventures, with prior experience as Vice President of Product Management at Facebook and CEO of Drop.io. He has invested in notable companies like OpenPhone and Identiq, focusing on sectors like Direct-to-Consumer and FinTech. Lessin’s career highlights include serving as a key executive at Facebook, leading [...]
Episode #648: Ed Latimore – Going From Zero to One, Taking Ownership, Positive Body Language, Strategic Hardship, & Hard Earned Lessons From The Hurt Business
Ed Latimore is a professional heavyweight boxer, best-selling author, and veteran of the U.S. Army National Guard. He earned a degree in Physics from Duquesne University. Ed has gained recognition for overcoming personal struggles with addiction and poverty. We recorded this at our 2025 Learning Leader Growth Summit in Scottsdale, Arizona. He’s [...]
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