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
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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
Positive-sum principles, deep relationships, and building enduring media businesses together
A.Patrick explains his core principle: spotting unrealized talent and feeling obligated to help it become visible, which he links to a formative Upanishads passage and a lifelong preference for “positive-sum” behavior.
B.They contrast goal-setting with principle-driven growth—Patrick argues goals create blinders, while principles keep you open to peripheral opportunities that create unpredictable “daisy chains” of outcomes.
C.They explore how biography, long conversations, and podcasting create “professional learners” with compounding advantages—plus why relationships and over-communication are central to leadership and sustained success.
D.Patrick details why he built Colossus and long-form profiles (despite skepticism): scarce, high-quality units of attention that spotlight people, are hard to copy, and scale beyond his own time—ending with stories about kindness, mentorship, and the roles that endure.
🧠 IDEAS WORTH REMEMBERING
5 ideas
1
A personal principle can replace goals—and guide every daily decision.
Patrick describes discovering (over years) a principle akin to Bret Victor’s “Inventing on Principle”: when you see something important violated or missing, you feel obligated to correct it in service of others, not yourself.
2
Patrick’s principle: find unrealized potential and champion it publicly.
He gets “abiding joy” from seeing talent early, building relationships, then using capital/media/network to help the world see what he sees—without needing direct personal gain as the motive.
3
Goals can create blinders; openness creates better outcomes.
Patrick argues that most of his best opportunities (like promoting Founders) arrived from the periphery, not from planned targets—so he optimizes for readiness, curiosity, and responsiveness instead of fixed endpoints.
4
Biographies and long conversations are “truth-seeking” tools.
Senra emphasizes slowing down for understanding—biographies reduce the incentive to self-mythologize and reveal recurring human patterns, helping listeners see their own lives more clearly.
They contrast generative motivation (service, love of craft) with negative drivers (insecurity, fame, resentment). Dirty fuel can produce results but often damages relationships and long-term well-being.
💬 WORDS WORTH SAVING
5 quotes
“By far, my favorite thing in the world is championing other people.”
— Patrick O’Shaughnessy
“Those who feed the hungry protect me. Those who don’t are consumed by me.”
— Patrick O’Shaughnessy (quoting the Upanishads)
“I’m not chasing anything. I have no goals.”
— Patrick O’Shaughnessy
“The world is desperate for some stuff like that… everyone’s so sick of this crap.”
— Patrick O’Shaughnessy (on high-effort profiles vs low-quality content)
“A lifelong quest to build something for others that expresses who you are.”
— Patrick O’Shaughnessy (definition of ‘life’s work’)
Championing undiscovered talentUpanishads and service-oriented worldviewGrowth Without Goals; principles over targetsMedia and investing as the same craftBiographies for “true understanding”Clean fuel vs dirty fuel ambitionProfessional learners; podcasting as leverageColossus profiles; scarce attention and difficultyLeadership as over-communication and teachingRelationships, roles, and generational ripple effects
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David Senra
