My Conversation With Patrick O'Shaughnessy, Founder of Colossus & Positive Sum | David Senra

Patrick O'Shaughnessy is the Chairman Emeritus of O'Shaughnessy Asset Management, the founder of Colossus, and the founder and CEO of Positive Sum. He is an investor, author, and podcaster who has devoted his career to understanding the world's best investors and entrepreneurs. Under his leadership, Colossus has become one of the largest investing-focused podcast networks in the world, producing shows including the flagship Invest Like the Best, which he hosts. At Positive Sum, he invests in early-stage companies creating and reinventing categories, with portfolio companies including Tegus, ID.me, Etched, and Vanta. After starting as an intern at his father's quantitative asset management firm in 2008, O'Shaughnessy became CEO in 2018. He became known for his deep research into factor-based investing, his quantitative approach to stock selection, and his ability to communicate complex investment ideas to a broad audience. His accomplishments include growing OSAM into a leading custom indexing platform before its acquisition by Franklin Templeton in 2021, launching Invest Like the Best in 2016 which was named among The Wall Street Journal's "5 Investment Podcasts You Should Listen To," founding Colossus in 2020 to build a media platform around his vision of learning in public, and authoring “Millennial Money: How Young Investors Can Build a Fortune in 2014.” Episode show notes: https://www.davidsenra.com/episode/patrick-oshaughnessy Survey: https://forms.scicommedia.com/t/mw83tpmsRzus Subscribe to my newsletter: https://www.davidsenra.com/newsletter *Made possible by* Ramp: ⁠⁠https://ramp.com⁠ HubSpot: ⁠⁠https://hubspot.com⁠ Eight Sleep: ⁠https://eightsleep.com/senra *David Senra* Website: https://www.davidsenra.com X: https://x.com/davidsenra Instagram: https://www.instagram.com/davidsenra https://www.threads.com/@davidsenra Facebook: https://www.facebook.com/senrashow LinkedIn: https://www.linkedin.com/in/davidsenra *Patrick O'Shaughnessy* X: https://x.com/patrick_oshag LinkedIn: https://www.linkedin.com/in/patrick-o-shaughnessy-6721176 Colossus: https://joincolossus.com Positive Sum: https://positivesum.com *Chapters* 00:00:00 The Joy of Championing Undiscovered Talent 00:02:21 How One Tweet Changed David's Life 00:05:07 The Upanishads Passage That Shaped Patrick's Worldview 00:08:34 Growth Without Goals Philosophy 00:10:40 Why Media and Investing Are the Same Thing 00:28:41 The Search for True Understanding Through Biography 00:31:04 The Daniel Ek Dinner That Launched This Podcast 00:34:28 Making Your Own Recipe From the Ingredients of Great Lives 00:39:11 The Privilege of a Lifetime Is Being Who You Are 00:48:25 Bruce Springsteen's Battle With Depression and Self-Worth 00:53:21 Clean Fuel vs Dirty Fuel: The Source of Your Ambition 00:57:03 Professional Learners: The Unfair Advantage of Podcasting 01:00:18 Relationships Run the World 01:06:30 The Origin Story of Invest Like the Best 01:08:05 Building Colossus: Why Start a Magazine in 2025 01:14:01 People Are More Interested in People Than Anything Else 01:17:32 Finding Jeremy Stern and Hiring Through Output 01:23:40 Learn, Build, Share, Repeat 01:30:07 The Daisy Chain: How Reading Books Led to Everything 01:30:32 Red on the Color Wheel: Sam Hinkie's Observation 01:37:13 Finding Your Superpower and Becoming More Yourself 01:42:57 Repetition Doesn't Spoil the Prayer: Teaching as Leadership 01:46:02 Life's Work: A Lifelong Quest to Build Something for Others 01:49:51 The Ten Roles Game and What Matters Most 01:57:03 Husband, Father, Grandfather: The Roles That Endure 01:59:48 The Kindest Thing: Tim O'Shaughnessy and Meeting Lauren 02:05:11 Conclusion #DavidSenra

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