Invest Like the Best with Patrick O'Shaughnessy · Colossus | Investing & Business Podcasts

Patrick O’Shaughnessy - Creating on Principle

·2 hr 7 min·5 clips

Patrick discovered his life's purpose after a line from the Upanishads hit him like a hammer.

Patrick O'Shaughnessy is the CEO of Positive Sum, host of Invest Like the Best, and the founder of the Colossus media network. This episode flips the format: David Senra, host of the Founders podcast, interviews O'Shaughnessy, who explains he has rarely agreed to be on the other side of the mic in five or six years of podcasting. The core theme is O'Shaughnessy's organizing principle: the discovery and championship of relatively unknown, talented people before the broader world notices them. He traces this to a personal turning point at age 26, when a line from the Upanishads — roughly that those who help others are the ones who matter — snapped into focus for him and replaced a hardened earlier version of himself. O'Shaughnessy shares that his deepest satisfaction comes not from personal accolades but from witnessing the success of people he championed, including podcast guests, founders his firm has backed, and friends. He connects this to Brett Victor's talk "Inventing on Principle," in which Victor argues that creators should find a guiding principle rather than a goal — Victor's own principle was that digital creators deserve instant feedback from their tools. O'Shaughnessy's principle is that when he identifies unrecognized talent, it is his obligation to act on that recognition. The episode traces the origin story of O'Shaughnessy's relationship with David Senra, who was tweeting into obscurity with his Founders podcast when O'Shaughnessy publicly championed it to his large, high-net-worth audience, transforming Senra's trajectory. O'Shaughnessy reflects on building Colossus and Positive Sum as vehicles for this principle, and on the media and investing businesses being natural complements. He is candid about not being goals-driven — he wrote an essay on "growth without goals" — and about preferring the quality of daily work over the milestone logic of achievement. The conversation is warmly personal and philosophically grounded, offering an unusual window into how a leading investor and media builder thinks about purpose and creative identity. Audiences interested in investing, media, philosophy of work, and entrepreneurship will find it deeply engaging.

As heard by us

A calm conversation about health, work, and the small circle that really matters.

The conversation builds a steady case that health, work, and public recognition all look different once relationships move to the center. Its clearest point comes in the contrast between being known for its own sake and doing work that matters enough to spread on its own because…

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Why you'd press play

Press play if you want a clear-eyed conversation about relationships, health, fame, and what really matters in work.

Read the full recommendation in PlayNext →

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