Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455]
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this special episode, Patrick O'Shaughnessy appears on David Senra's show for a rare interview where he shares his philosophy on championing undiscovered talent, building meaningful relationships, and creating value through principled action. (05:14) The conversation explores Patrick's organizing principle of finding and fostering unrealized potential in others, his approach to "growth without goals," and how everything in his life has stemmed from a simple love of reading books that created a daisy chain of opportunities. (30:01)
- Core themes include finding your life's organizing principle, the power of championing others before they deserve it, building fewer but deeper relationships, and creating sustainable business models around acts of service.
Speakers
Patrick O'Shaughnessy
Patrick is the CEO and CIO of Positive Sum, an investment firm, and host of the popular "Invest Like the Best" podcast. He comes from a family of successful entrepreneurs, including his great-grandfather Ignatius Aloysius O'Shaughnessy who was one of the richest oil wildcatters in America and gave away most of his fortune anonymously. Patrick has built multiple successful businesses and is known for his principled approach to investing and championing undiscovered talent.
David Senra
David is the host of the "Founders" podcast where he has recorded over 400 episodes studying the greatest entrepreneurs and founders in history through their biographies and autobiographies. He came from challenging circumstances and used books and podcasts as mentors to transform his life, eventually building one of the most respected business podcasts with a highly valuable audience of entrepreneurs and investors.
Key Takeaways
Find Your Organizing Principle, Not Goals
Patrick advocates for discovering a life principle rather than setting traditional goals. (17:06) His principle is that when he sees undiscovered talent, it becomes his obligation to champion that person, learn from them, and help the world see what he sees. This principle guides every decision he makes and allows him to remain open to unexpected opportunities that goals might cause him to miss. He wrote about "growth without goals" at age 28, realizing that talented people often achieve their goals but then limit themselves with blinders, missing the truly interesting opportunities that come from the periphery.
The Compound Effect of Championing Others
The most fulfilling work comes from betting on people before they deserve it and helping foster their unrealized potential. (05:36) Patrick explains that two-thirds of answers to "what's the kindest thing anyone's ever done for you" involve someone making a bet on the person first, before they deserved it. This creates a compound effect where championing others becomes the most sustainable source of satisfaction, unlike pursuing money, power, or fame which provide diminishing returns. He traces his entire career success back to this principle of finding and supporting talented people.
Deep Relationships Over Broad Networks
Invest heavily in fewer, deeper relationships rather than maintaining broad, superficial networks. (104:00) Patrick maintains a small list of people "for whom he would do anything" as his most prized possession, explaining that you can only meaningfully support 10-15 people at this level. David reinforces this by describing how his meaningful conversations require hours to warm up and get past superficial exchanges. This approach runs counter to typical networking advice but creates more valuable, lasting relationships that compound over time.
Create Through Personal Expression and Service
The most sustainable form of creation comes from pouring yourself into work that serves others. (43:24) Patrick quotes Joseph Campbell: "The privilege of a lifetime is being who you are," explaining that the best creators make things that reflect themselves while benefiting others. This creates what he calls "abiding joy" - satisfaction that doesn't run out like traditional resources but actually grows through use. The work becomes an act of service where your personal expression creates value for others, making it both fulfilling and commercially viable.
Use High-Volume Practice to Develop Taste
Develop exceptional judgment by consuming massive volumes of the thing you want to create or evaluate. (89:18) Patrick spent his twenties reading thousands of books and profiles, giving him extremely high "reps" that prepared him to recognize and create great work later. David similarly describes reading as developing "constant refinement of taste" through volume. This approach allows you to distinguish between good, average, and exceptional work, which becomes crucial when hiring people, making investments, or creating original content. The pattern works across domains - whoever made the best example of something is likely the best person to hire.
Statistics & Facts
- Patrick comes from a family with significant entrepreneurial success - his great-grandfather Ignatius Aloysius O'Shaughnessy was one of the richest men in America and was involved in the Standard Oil antitrust breakup. (30:30)
- Patrick's team at Positive Sum and related companies has grown to approximately 16 people, all organized around the principle of finding and championing talented individuals. (18:18)
- David mentions that Patrick's show has an incredibly valuable audience where the average net worth of listeners would be "mind boggling" if calculated, representing significant influence in business and investing circles. (10:08)
