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.”

I have a uniquely smart and sophisticated audience, so if you are interested in sponsoring The Learning Leader Show, email me (Ryan@LearningLeader.com) with the subject “sponsorship.” Some previous sponsors have been Calloway Golf, Ogio, Gusto, Freshbooks, LinkedIn Learning, and Municipal.

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.

If you’ve enjoyed the podcast, please write a quick iTunes review here, because it will help more people discover The Learning Leader Show.


Episode #585: AJ Jacobs – Creating a Flexible Mind, The Value of Slow-Thinking, Embracing Virtue, Showing Gratitude, and The Year of Living Constitutionally

A.J. Jacobs is an author, journalist, lecturer, and human guinea pig. He has written four New York Times bestsellers that combine memoir, science, humor, and a dash of self-help. Among his books are The Year of Living Biblically, Thanks a Thousand, and most recently, The Year of Living Constitutionally. He is a [...]

Episode #584: Craig Robinson – The “Must-Have” Qualities For Coaching Excellence, Becoming a Better Listener, Learning From a Legend, and Thanksgiving Dinner With a Young Barack Obama

Craig Robinson is the host of Ways to Win. He’s the executive director of the National Association of Basketball Coaches (NABC). From 2017-2020, he served as the VP of Player Development for the New York Knicks. Previously, he was a Division I head men’s basketball coach at Oregon State and Brown. He [...]

Episode #583: Jason Fried – Growing Without Goals, Earning An Investment From Jeff Bezos, Making Tough Decisions, Keys To A Great Partnership, Hosting Leadership Retreats, and Creating A Writing Practice

Jason Fried is the Co-Founder & CEO at 37 Signals. 37signals is a privately-held company committed to building the best web-based tools possible with the least number of features necessary. Jason is also the co-author of Getting Real, REWORK, Remote, and “It Doesn’t Have to Be Crazy at Work.” WATCH this conversation [...]

Episode #582: Cal Newport – Obsess Over Quality, Create Time Freedom (like Benjamin Franklin), Limit Daily Goals, Work At a Natural Pace, & How To Be So Good They Can’t Ignore You

Cal Newport is a professor of computer science at Georgetown University.  In addition to his academic work, Cal is a New York Times bestselling author who writes about the intersection of technology, productivity, and culture. Some of my favorite books that he’s written are So Good They Can’t Ignore You, Deep Work, [...]

Episode #581: Paul Rabil (The LeBron James of Lacrosse) – Never Missing a Day, Goal Setting, The Voice No One Hears, and The Difference Between Self-Promotion & Passion (The Way of The Champion)

Paul Rabil is a former professional lacrosse player and co-founder of the Premier Lacrosse League, the 2020 Sports Business Awards Breakthrough League of the Year. Rabil holds the all-time scoring record in professional lacrosse; has won championships and MVP awards as a college, professional, and international athlete; and is a two-time World [...]

Episode #580: Robin Sharma – The 5 Journal Prompts, 8 Hidden Habits, Meeting People In Person, Working Out Everyday, Becoming The Architect of Your Future, Building a Rich Life

For nearly 20 years, many of the most well-known organizations on the planet, ranging from Nike, GE, Microsoft, FedEx, PwC, HP, and Oracle to NASA, Yale, and YPO have chosen Robin Sharma for their most important events. Robin has sold over 20 million books in 96 countries. WATCH this conversation on YouTube. [...]

Episode #579: David Perell – Setting The Standard, Cultivating Your Taste, Pursuing Excellence, Becoming a Sloganeer, Always Working/Never Working, & Lessons From a Mysterious Billionaire

David Perell is the founder and CEO of Write of Passage. He’s taught thousands of people from more than 70 countries how to become a more effective writer. Additionally, he’s the host of the How I Write Podcast where he interviews the world’s greatest writers and goes inside their process. WATCH this [...]

Episode #578: Scott Galloway – Adding Surplus Value, Asking For What You Want, Ketamine Therapy, Crude Humor, Being Moved To Tears, & The Algebra of Wealth

Scott Galloway is a professor at NYU’s Stern School of Business. A serial entrepreneur, he has founded nine firms, including L2, Red Envelope, Prophet, and Section4. In 2012, he was named one of the “World’s 50 Best Business School Professors” by Poets & Quants. He’s the author of multiple best-selling books including [...]

Episode #577: Jeff Wetzler – Tap Into the Hidden Wisdom of People Around You for Unexpected Breakthroughs In Leadership and Life (ASK)

Jeff Wetzler is the co-founder and co-CEO of Transcend. Transcend is a non-profit focused on accelerating innovation in the design of learning environments. Before that, he was the Chief Learning Officer of Teach For America. He’s the author of a new book called, Ask: Tap Into the Hidden Wisdom of People Around [...]

Episode #576: Scott Belsky – Adding Texture to Time, Feeling Unrushed, Pushing Yourself Physically, Narrating the Journey, Becoming an Excellent Writer, and Why You Should Never Outsource Your Story

Scott Belsky co-founded Behance in 2006 and served as its CEO for six years. Behance was acquired by Adobe in 2012. Since then he has had a variety of roles with the company and is currently Adobe’s Chief Strategy Officer, and EVP of Design & Emerging Products. He’s also the author of [...]

Episode #575: The Score That Matters – Growing Excellence In Yourself and Those You Lead

In The Score That Matters, Ryan Hawk and Brook Cupps show that the internal score is what matters most—it reveals whether we are living in alignment with our purpose and values. It also measures how we are leading ourselves and others, prompting us to: Differentiate between the two scoreboards that run our life, [...]

Episode #574: Guy Kawasaki – Leadership Lessons From Steve Jobs, Learning How To Sell, Becoming a Chief Evangelist, and The ‘Think Different’ Philosophy

Guy Kawasaki is the chief evangelist of Canva and the author of 16 books. He was the chief evangelist of Apple, Mercedes-Benz brand ambassador, and a special assistant to the Motorola Division of Google. Guy has a BA from Stanford, an MBA from UCLA, and an honorary doctorate from Babson College. WATCH this [...]