My conversation with Patrick O'Shaughnessy (@patrick_oshag), founder and CEO of Colossus & Positive Sum. 0:00 The Joy of Championing Undiscovered Talent 2:21 How One Tweet Changed David's Life 5:07 The Upanishads Passage That Shaped Patrick's Worldview 8:34 Growth Without Goals Philosophy 10:40 Why Media and Investing Are the Same Thing 28:41 The Search for True Understanding Through Biography 31:04 The Daniel Ek Dinner That Launched This Podcast 34:28 Making Your Own Recipe From the Ingredients of Great Lives 39:11 The Privilege of a Lifetime Is Being Who You Are 48:25 Bruce Springsteen's Battle With Depression and Self-Worth 53:21 Clean Fuel vs Dirty Fuel: The Source of Your Ambition 57:03 Professional Learners: The Unfair Advantage of Podcasting 1:00:18 Relationships Run the World 1:06:30 The Origin Story of Invest Like the Best 1:08:05 Building Colossus: Why Start a Magazine in 2025 1:14:01 People Are More Interested in People Than Anything Else 1:17:32 Finding Jeremy Stern and Hiring Through Output 1:23:40 Learn, Build, Share, Repeat 1:30:07 The Daisy Chain: How Reading Books Led to Everything 1:30:32 Red on the Color Wheel: Sam Hinkie's Observation 1:37:13 Finding Your Superpower and Becoming More Yourself 1:42:57 Repetition Doesn't Spoil the Prayer: Teaching as Leadership 1:46:02 Life's Work: A Lifelong Quest to Build Something for Others 1:49:51 The Ten Roles Game and What Matters Most 1:57:03 Husband, Father, Grandfather: The Roles That Endure 1:59:48 The Kindest Thing: Tim O'Shaughnessy and Meeting Lauren 2:05:11 Conclusion Includes paid partnerships.