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

Summary

• Patrick O’Shaughnessy articulates the principle behind his work: when he sees “enormous, not-yet-realized potential,” it is his obligation to champion it, with nothing required in return. That principle links his media and investing work, and now informs decisions such as hiring his roughly 16-person team. “By far my favorite thing in the world is championing other people.”
• He believes in growth without goals: his most-read essay was titled “Growth Without Goals,” and he avoids fixed targets because “everything that’s ever worked for me has come out of the periphery.” The chain from reading to a book email, podcast, software business, early-stage investing, and a new investment firm was not predictable in advance. Separately, David explains how his own thinking about principles emerged while considering what example to set for his son.
• Colossus is David Senra’s bet on scarce, difficult-to-copy attention: long-form profiles take months or years, and people initially called the magazine a stupid idea. A magazine cover proved to be powerful because “people can’t say no to a cover.” David suspects the profiles may eventually dwarf the podcast, and Patrick wants that because it would remove David’s own time and energy as the bottleneck.
• Their founder-selection framework is “best story wins,” built from originality, hardship, and transformation. Patrick applies it by asking founders to spend two hours telling their life story before the company. The harder a business is to build, the harder it is to copy; transformation means the customer’s life gets better. The leadership test is whether people want to follow you, and “the reward for great work is more work.”
• The clean-fuel/dirty-fuel discussion contrasts Springsteen and LBJ. David describes Springsteen’s pain-driven ambition, later depression, therapy, and eventual recognition that work and fame were not enough; LBJ remained manipulative despite comparable drive. David admits that Patrick’s long-running push for a team exposed his own distrust: “I don’t f*ing trust anybody.”
• Patrick’s weakness, in Sam’s formulation, is being “red on the color wheel”: intense and extraordinarily effective when focused, but prone to whiplash when attention shifts. The example is his launching his own fund and reducing his commitment to Sam’s first fund within a month. He and David connect the repair to simplification, focus, and overcommunication.
• Their relationship philosophy culminates in Patrick’s story about Tim O’Shaughnessy. Tim helped transplant Patrick into Notre Dame’s social circle, leading to his wife, best man, and lifelong friendships. “Whole lives are downstream of simple, quick acts of kindness.”

Deep dive

1. Patrick’s wiring: champion unknown talent before anyone else sees it

• Senra opens on Patrick’s “almost obsessive” interest in finding talented, relatively unknown people and putting his resources behind them. Patrick says this lets him learn about someone “before other people do”; he likes the frontier, fresh ideas, and “by far my favorite thing in the world is championing other people.” His own accolades did little for him emotionally, while other people’s wins reach him “deep in my soul and heart and gut.”
• He also likes picking sides: “I like saying, ‘I like this person’” and, by extension, prefer them to the other available options. He is architecting his life to do more of that for as long as possible.
• Senra’s old description of him was “positive sum”: Patrick does not do things for money, though Senra stresses that this does not mean he is noncommercial or unsuccessful.

2. The tweet that changed Senra’s life

• Senra retells the origin story: after a 5.5-year struggle with Founders, he had no followers and was tweeting into oblivion. Patrick posted roughly, “I never find new podcasts to listen to, and I think David Senra’s Founders podcast is excellent,” linking the Estée Lauder episode.
• At the time, the podcast was paywalled because Senra had not figured out the business model. He normally received only a few subscriber emails a day; the next morning, Patrick’s tweet produced a wall of notifications “all the way down.”
• Senra returns to the idea he heard from their mutual friend Sam: “People are power, and the best ones change everything.” Once you see that, he says, you become almost ruthless about who gets access to you.
• Senra admits that he probably would not have promoted a potential competitor so instinctively and asks what Patrick saw.

3. “Someone bet on me before I deserved it” — and the Upanishads

• Patrick says someone compiled roughly 500 answers to his recurring question, “What’s the kindest thing anyone’s ever done for you?” About two-thirds had the same answer: someone bet on me before I deserved it and saw potential I did not yet see.
• At 26, while adrift and searching, Patrick found a passage in the Upanishads, “probably the most important book” to him. The passage roughly said, “Those who feed the hungry protect me. Those who don’t are consumed by me.” It felt like a hammer blow and led to the realization that “the whole point of this is to help other people.”
• Patrick says his ideal activity would be repeatedly auditioning people to see what potential others have missed, then fostering it and helping the world see it. Senra says Patrick had never expressed the idea so clearly in their hundreds, perhaps thousand, conversations.

4. Growth without goals; find a principle instead

• Patrick rejects Senra’s language of “chasing”: “I’m not chasing anything. I have no goals.” His most-read essay was called “Growth Without Goals.” He does not want a large fixed target because talented people who set goals often achieve them, but then travel with blinders on. “Everything that’s ever worked for me has come out of the periphery.”
• He borrows the form of this thinking from Bret Victor’s talk “Inventing on Principle.” Victor’s principle was to give digital creators instant feedback, collapsing the delay between making a change and seeing its result. Patrick’s own principle is that when he sees enormous unrealized potential, it is his obligation to help foster it and show others what he sees.
• Patrick says it took him a decade to articulate the principle, which now informs decisions throughout his life, including his roughly 16-person team: “Who can I find, see something in, bring them in, and then make their career explode?”
• Separately, David says an essay and framework of his own began when he was 28, commuting between New York City and Stamford and preparing for the birth of his son Pierce. He was asking what example he wanted to set, because children copy what their parents do rather than what they say.
• David also explains that before identifying his own principle, he borrowed Victor’s instant-feedback principle and used it as the primary design principle for software in his last business. The software worked well, and the business grew substantially as a result. He has never met Victor but would like to.

5. Chase the feeling of being alive; fear is why people don’t

• Patrick quotes a line he attributes either to Alan Watts or possibly Joseph Campbell: “We’re not searching for the meaning of life, but for the feeling of being alive.” David says that feeling can serve as a red-light/green-light test while searching for a principle.
• David’s answer to why people do not pursue what makes them feel alive is usually simple: fear. He has spent months thinking about “the best story always wins,” which he decomposes into originality, hardship, and transformation.
• Original paths are frightening because responsibility falls on you and because pursuing them often means leaving a comfortable existence. When people are pressed on why they do not pursue them, David says, the reasons usually add up to “I’m afraid.”

6. David’s introspection was a tool

• David traces his intense introspection to a childhood fear of death. At roughly five years old, he needed his parents to hold his hand while he fell asleep because he would spiral over the idea that one day he would not exist.
• That fear led him toward philosophy, religious traditions, metaphysics, psychology, and personality tests as he tried to understand the point and meaning of life. It also made him wary of living a dull, predetermined existence.
• Now that he believes he understands what he wants to do, he says he barely thinks about it. He has lost much of his former interest in introspection. Patrick suggests that introspection was the tool and that David no longer needs it once the job is done; David tentatively agrees.

7. Patrick names Senra’s principle: founder of a family

• Asked to interpret Senra, Patrick contrasts their backgrounds. Patrick was “born on proverbial third base,” into a family shaped by his great-grandfather Ignatius Aloysius O’Shaughnessy, known as IA. IA was the 13th of 13 children, an oil wildcatter, and, Patrick thinks, the first well he drilled still pumps oil. He became one of the richest men in the United States, was caught up in the Rockefeller/Standard Oil antitrust action, and gave away most of his fortune, often anonymously.
• At IA’s funeral, Patrick’s 11-year-old father met strangers who explained that IA had cut their hair, paid for their children’s college, or bought them houses.
• Drawing on Sam’s distinction between founders of businesses and founders of families, Patrick calls Senra “the founder of your family” and says it may be his greatest accomplishment. Senra broke from his inherited circumstances, searched for mentors in books and founders, changed his own life, and has since helped change other people’s lives.

8. Why biographies: ingredients, not recipes — and “screw base rates”

• Senra says he listens to podcasts at 1x and reads about 25 pages an hour because he wants an understanding of how things actually are, not merely how people say they are.
• He favors biographies and autobiographies because the subject may be dead or old enough to have little incentive to lie. Their problems with family, business, relationships, and life reveal that nothing one experiences is entirely unprecedented.
• The stories are not only about the subjects; they become material for the reader’s own understanding, much as a song or movie can make someone recognize their own experience.
• Patrick says people should use these lives as ingredients, not recipes. Common pitfalls are not inevitable by-products of success: “Screw base rates. I never care what the base rate is. The most interesting stuff is outliers by definition.”
• David quotes Springsteen’s idea that people do not come to concerts to learn, but to be reminded of things they already know are true. That is part of why they describe Founders as “a church for entrepreneurs.” Senra’s goal is not merely to accumulate potential but to use his abilities fully rather than “tap-dance on a giant reservoir of potential.”

9. Abiding joy versus money, power, and fame

• Patrick invokes the Upanishads’ idea of “abiding joy”: a joy that does not run out and that grows as it is used. Money, power, and fame are recognizable proxies for success, but once people acquire them, they can become the next objects of pursuit. The feeling of being alive is a safer guide.
• Patrick admits that he has been intoxicated by all three at different points. He particularly dislikes fame and jokes that he wishes he could use the memory-erasing device from Men in Black at the end of each episode.
• Senra distinguishes fame for its own sake from work so good that it naturally spreads. For him, being legible to others creates relationships with people he otherwise could not reach.
• Senra ranks health, work, and relationships, with health first. Patrick disagrees based on his own history of serious health problems. He ate extremely well, exercised daily, kept detailed logs, and tried every approach he could find, yet improved only after correcting his work and relationships. He says it cannot be a coincidence and cites “The Body Keeps the Score.”

10. Springsteen versus LBJ: clean fuel and dirty fuel

• Senra’s Springsteen discussion began after Jimmy Iovine told him to watch Deliver Me from Nowhere. David describes Springsteen’s terrible childhood environment, his maniacal will to escape it, and the work ethic that brought him fame, wealth, and stardom.
• After getting what he thought he wanted, Springsteen fell into the deepest depression of his life in his mid-30s. David says Springsteen eventually recognized that fame and work were not what he actually wanted, especially because he had not developed the emotional skills to build the family life he desired. He went through roughly 25 years of therapy and was candid about the period from age 35 to 67.
• David contrasts him with LBJ, drawing on Robert Caro’s story of Johnson running through Washington. People assumed he was running to stay warm because he lacked a coat; he continued running in summer because he had finally reached the place where he intended to pursue his ambitions. David sees a similar source of drive but a different result: Springsteen became generative, while LBJ remained manipulative.
• David says nearly all of the books Patrick has read concern people fueled by “dirty fuel.” Dirty fuel can work extremely well, but it consumes the person. Patrick says his grandmother’s repeated question was not “How successful are you?” but “What are you doing for other people?” He is convinced service is the way out.
• Patrick’s years of urging Senra to build a team expose Senra’s own parallel problem: “It makes sense why I don’t have a team, because I don’t f*ing trust anybody.” Patrick says David is telling Springsteen’s story while also talking about himself; David agrees.

11. Whose ideas Patrick borrowed — and who shaped him

• Patrick identifies three people whose ideas shaped the software business: Daniel Ek on building software, Bret Victor on instant feedback, and Chetan Puttagunta of Benchmark on selling it. Chetan reviewed demos at Benchmark’s office despite having no investment stake. Patrick’s method was to ask excellent practitioners how to do something and then apply what they told him.
• Other major influences include Herb Allen of Allen & Company, whom David describes as an apex example of selecting and supporting people and as someone willing to discard major commercial opportunities if the person was wrong; the private Reece Duca, whose guiding phrase was “Simplify your life with rhythm and harmony”; and Jesse Beyroutey, whom David predicts may become one of the great investors ever.
• David says he interviews people once a week with microphones present, but in practice speaks with roughly 10 people a day—40 or 50 times a week—as part of his ordinary life.

12. The Colossus profiles: scarce units of attention

• Senra says he is interested in creating and controlling “valuable, scarce units of attention” and distributing them to people the team believes in. Colossus exists to support profiles that require months, quarters, or years of research and to shine a light beyond podcasting on founders, investors, artists, and other compelling people.
• David’s editorial standard came from David Remnick’s compilation of New Yorker profiles: the strongest profiles pair a person obsessed with a thing and a writer equally obsessed with understanding that person.
• David read roughly one million profiles and found Jeremy Stern’s piece on Palmer Luckey in Tablet to be the best. Stern is now editor-in-chief of Colossus.
• David says the Josh Kushner/Thrive profile became a “break the internet” moment. He was still reading about the Holocaust 45 minutes into it because the family history was necessary to understand the soil from which Josh and his family emerged. Stern’s own family history gave him unusual knowledge of that material.
• David thinks profiles became less common because they are difficult, slow, and poorly paid. Short-form video is much cheaper and faster, while the world is increasingly hungry for carefully made work rather than optimized junk-food content.
• The immediate trigger for the magazine idea was an existing publication with famous people on its covers. David realized that “people can’t say no to a cover”: it is an unusually powerful form of attention that he could distribute to people he admires.

13. Patrick wants Colossus to dwarf the podcast

• When Senra says Patrick’s preference is not self-evident, Patrick acknowledges that he would rather the profiles become larger than the podcast.
• The reason is partly selfish: if other talented people create the work, Patrick gets more excellent material to read, while David can receive more drafts and research reports from his team. “It’s turtles all the way down”: the same investigation, writing, and clear thinking can happen without being limited by one person’s time.
• Patrick still wants to keep doing interviews and hopes the podcast remains large, but he would prefer a world in which the broader Colossus project is no longer rate-limited by David’s bandwidth. That would let the team support more writers, create documentaries or gatherings, and introduce more talented people to the world.

14. “There’s always room for great”: Disney, Ellison, and Munger

• Patrick’s answer to “we don’t need another podcast” is that no one would conclude there is no need for more music or movies. The world needs less bad work, not less great work. The Profiles found an idea that had been hiding in plain sight and executed it carefully.
• Patrick tells the story of Walt Disney’s obsession with Disneyland. Amusement parks were widely regarded as low-quality, traveling-carnival operations; Disney wanted to take the concept and improve every part of it while removing what did not make sense. Patrick summarizes the lesson: “Mediocrity is always invisible until passion shows up and exposes it.”
• Patrick also describes Larry Ellison’s desire to move Oracle’s associations from ordinary database companies toward IBM and Microsoft. Ellison picked a fight with Bill Gates because people are more interested in personalities than companies or technologies; he said Oracle and its products rose with his increased profile.
• A related hiring lesson comes from Brent Beshore asking Munger how he and Warren find great CEOs. Munger’s answer was essentially to find someone who is already a great CEO and ask them to do it for you. In a separate COVID-era Zoom discussion, an investor became frustrated with abstract lists of inventor attributes and said, “Morons, who cares? Did they make a good invention?”

15. Learn, build, share, repeat — the daisy chain

• Patrick spent much of his 20s reading thousands of books and began sharing his notes because the activity felt isolated. His loop was: “Learn, build, share, repeat — and just do that until I die.”
• The chain was not planned: reading led to a monthly email naming favorite books; the email found the first podcast listeners; the podcast introduced him to people who helped build and sell his software business; that led to small early-stage investments, then a new investment firm and larger investments in companies.
• Patrick says the whole chain began because he loved reading and did something about it. He advises younger people to find the activity in which they naturally accumulate a high number of repetitions. That can become the base for a compounding learning curve.
• He compares the process to progressive overload, an idea he discusses with Jeremy Giffon: a little more difficulty, repeated over time, and continued effort toward failure.
• Patrick emphasizes that he was extraordinarily lucky to have parents, paid college, and the freedom to spend so much time reading. He considers acknowledging those advantages important.
• Senra adds Sam’s “breadcrumbs” idea: put work into the world that others can discover. “Pour a year of your life into making one amazing thing that people are amazed by,” and unexpected opportunities may follow.

16. “Red on the color wheel”: Patrick’s named weakness

• On a five-hour walk in Columbia, Missouri, Sam described Patrick as “red on the color wheel”: voracious, intense, and unusually effective when interested, but liable to whiplash when his attention shifts. Senra calls the focused version Patrick’s “Eye of Sauron” and once flew to Greenwich to pull his attention back to an important matter.
• The example was Sam’s first fund. Patrick initially committed to invest, but when the documents were ready a month later, he had to reduce the amount because he had launched his own fund and needed to make a general-partner commitment before selling his business. The fund had emerged from an opportunity in the periphery.
• Patrick says he cannot visualize images with his eyes closed and does not retain event memories in the usual way. As a result, he can become intensely focused on an idea and then later have no mental connection to the thing that had previously consumed him, which is jarring for people who committed to executing it. Brad Jacobs once tried to guide him into visualizing something; it did not work.
• Patrick has worked to simplify his life with rhythm and harmony, focus on fewer things, and avoid the “flavor of the month club.” Senra says he has not experienced an Eye of Sauron moment with Patrick in quite a while.
• Senra’s related lesson, influenced by Ari Emanuel, is to overcommunicate. Unspoken assumptions can stack up, while explicit communication prevents people from believing they are looking at the same situation when they are not. He also notes that he and Patrick worked together for years without a written contract, relying on their word.

17. Leadership, repetition, and the definition of life’s work

• Patrick once called everyone he knew to ask for a definition of a good leader. Ravi Gupta’s answer was his favorite: “A great leader is someone that other people want to follow.”
• Patrick says such leaders are hypercommunicative, consistent, willing to lead from the front and take arrows, and quick to explain changes. He admits he was poor at this for a long time because his excitement made him run ahead of the people he wanted to bring with him.
• Senra’s supporting examples are that “repetition is persuasive,” that “repetition doesn’t spoil the prayer,” and that Sol Price believed leaders should spend roughly 90% of their time teaching. Senra also says that in his “How Elon Works” episode—which he thinks is Founders’ most-downloaded episode—Elon repeats his four-part algorithm so often that executives mouth the words along with him.
• Patrick’s main team maxim is “The reward for great work is more work.” He defines life’s work as “a lifelong quest to build something for others that expresses who you are.” He uses Thomas Jefferson’s tombstone as an example: it emphasizes authorship of the Declaration of Independence and founding the University of Virginia, not the presidency.
• For investing, Patrick’s favorite founder question is: “Give me two hours; tell me your whole life story up until the point you founded your company.” In that context, originality is path dependency, hardship makes a business harder to copy, and transformation means the customer’s life improves substantially.
• Founder heroics are often necessary early, but Patrick says people eventually realize they will not be rewarded with more great work unless they become good leaders.

18. The roles game: who are you when everything else is stripped away

• Patrick knows people who repeatedly change careers, including John Pfeffer, who moved from a senior role at KKR to becoming a major figure in cryptocurrency and then to building a grocery chain in the United Kingdom. Pfeffer enjoys abandoning his existing network and rebuilding from scratch.
• Patrick is less drawn to people who simply stop making things. He and Senra use “casual” as shorthand for people they do not want to spend time with.
• In a game, participants write down 10 roles they play and discard them one at a time until one remains. Patrick’s father-in-law Dan, a highly successful figure in healthcare and insurance, kept “grandfather” as his final role. Patrick calls him the Michael Jordan of grandfathers.
• That kind of devotion is, to Patrick, every bit as successful as the achievements of famous business leaders because it ripples through descendants. Bill Campbell is another example: he focused on transforming a small number of executives rather than pursuing money, fame, or power.
• Senra’s own generational example is his grandfather, who was 30, had no education or English, worked in a shoe factory and as a butcher, and left Cuba after recognizing the danger posed by Fidel Castro. One decision by someone Senra barely remembers changed the generations that followed.
• Patrick’s final role in the game was probably husband or father. More broadly, he values a list of perhaps 10 to 15 people “for whom I would do anything.” That list is his prized possession, even if he occupies a less central place on some of their lists.

19. The kindest thing: Tim, a fake ID, and a whole life downstream

• Senra turns Patrick’s own question back on him. Patrick first names his third cousin Tim O’Shaughnessy. After being rejected by every college he initially applied to, Patrick attended another school, earned strong grades, and transferred to Notre Dame as a sophomore without knowing anyone.
• Tim sought him out, brought him a fake ID identifying him as 5-foot-4 with blonde hair and blue eyes, and organically transplanted him into his social circle. Tim would even tell friends he was sick and ask them to show Patrick a good time.
• That kindness led Patrick to his wife, his best man, and the only other non-family groomsman at his wedding. On Patrick’s first night at Notre Dame, he went to the Boat Club, which let him in with the fake ID and was shut down three weeks later for admitting people with such IDs. The first girl he spoke to there was Lauren, who became his wife; they have been together for about 20 years.
• Tim died tragically young, but Patrick thinks about him constantly because without Tim, his current life would not exist in anything like its present form. “Whole lives are downstream of simple, quick acts of kindness.” Senra closes by saying that this is why Patrick should do more podcasts.