Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455]

This week is a special episode. Only David Senra could get me to be on the other side of the mic. Because I don’t plan on being interviewed often, I wanted to share this conversation, which I so enjoyed, with our audience. It went in a very different direction than I expected. We barely talk about investing or interviewing. Instead, we talk about finding an organizing principle for life, undiscovered talent, and the idea that “the reward for good work is more work.” We also discuss the principles that guide how I think about building Invest Like the Best, Colossus, and Positive Sum. This conversation was originally recorded and released on David Senra, and I wanted to share on the Invest Like The Best feed as well. Please go follow what he’s doing, there’s no one like David. Enjoy! For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠'s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus. ----- ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Vanta is trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit vanta.com/invest. ----- ⁠Rogo⁠ is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit ⁠WorkOS.com⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Timestamps (00:00:00) Welcome to Invest Like The Best (00:04:26) Intro (00:05:14) The Joy of Championing Undiscovered Talent (00:07:33) How One Tweet Changed David's Life (00:10:16) The Upanishads Passage That Shaped Patrick's Worldview (00:15:32) Growth Without Goals (00:17:24) Why Media and Investing Are the Same Thing (00:33:05) The Search for True Understanding (00:35:36) The Daniel Ek Dinner That Launched David’s Podcast (00:39:02) Making Your Own Recipe From the Ingredients of Great Lives (00:43:46) The Privilege of a Lifetime Is Being Who You Are (00:52:06) Bruce Springsteen (00:57:23) Clean Fuel vs Dirty Fuel: The Source of Your Ambition (01:01:43) The Unfair Advantage of Podcasting (01:04:12) Relationships Run the World (01:11:10) The Origin Story of Invest Like the Best (01:12:45) Building Colossus: Why Start a Magazine in 2025 (01:18:42) People Are More Interested in People Than Anything Else (01:22:12) Hiring Through Output (01:26:23) Learn, Build, Share, Repeat (01:30:01) The Daisy Chain: How Reading Books Led to Everything (01:33:15) Red on the Color Wheel: Sam Hinkie's Observation (01:40:17) Finding Your Superpower and Becoming More Yourself (01:45:06) Repetition Doesn't Spoil the Prayer: Teaching as Leadership (01:48:11) Life's Work: A Lifelong Quest to Build Something for Others (01:52:00) The Ten Roles Game and What Matters Most (01:59:12) Husband, Father, Grandfather (02:01:52) The Kindest Thing

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Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] is an episode from Invest Like the Best by Colossus.

This episode is 126:40 long.

This episode was published on Jan 20, 2026.

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