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

Summary

  • Patrick O’Shaughnessy, interviewed for once (by David Senra), names his organizing principle after a decade of trying to articulate it: when he sees enormous unrealized potential in a person, it is his obligation to champion it — get to know them, introduce them, “help the world see what I see.” He credits the frame to Bret Victor’s “Inventing on Principle” talk: find a principle, not a goal, and let it inform “literally every decision you make every day.”
  • He rejects goals for himself — his most-read essay, “Growth Without Goals,” written at 28 — because talented people who set goals achieve them, and “the second you set some big goal… you have blinders on.” Everything that worked came “out of the periphery”: Sam Hinkie texting him about Senra, an out-of-left-field investment that became a fund in a month in summer 2020.
  • The empirical anchor: someone on Twitter compiled ~500 answers to his closing question (“kindest thing anyone’s done for you”) and roughly two-thirds were “someone made a bet on me before I deserved it.” That plus a line from the Upanishads at 26 — “Those who feed the hungry protect me. Those who don’t are consumed by me” — fixed his worldview: “the whole point of this is to help other people.”
  • Talent-selection heuristic: judge the artifact, not the attributes: he quotes an investor cutting off a founders-as-inventors debate — “Morons, who cares? Did they make a good invention?” — and Munger via Brent Beshore on hiring for potential: “We don’t do that.” Corollary for the ambitious: “pour a year of your life into making one amazing thing… amazing things will happen, I promise you.”
  • Colossus’s magazine bet is a contrarian media thesis: profiles became rare because they’re hard and the pay is terrible, which is exactly why he wants them — “the key is stuff that sounds dumb but isn’t.” The Josh Kushner/Thrive profile “broke the internet”; the cover is leverage (“people can’t say no to a cover”); and he explicitly wants Colossus to dwarf the podcast so output is “no longer rate limited by my time.”
  • Sam Hinkie’s diagnosis of his biggest weakness — “red on the color wheel”: ferocious intensity when locked in, whiplash when attention moves. Patrick ties it to discovering he can’t visualize with his eyes closed and has near-zero event memory, and to the leadership fix: over-communicate. Ravi Gupta’s definition stuck — “a great leader is someone that other people wanna follow.”
  • The fuel argument is the episode’s spine: dirty fuel (pain, fame-chasing) works but consumes you — Springsteen got everything he wanted and dropped into his life’s deepest depression in his mid-30s; LBJ never got out. Clean fuel is the abiding joy of the Upanishads: “as you use it, you get more of it.” Patrick’s 99-year-old grandmother’s version: “Congratulations on all the success. Who gives a shit? What are you doing for other people?”
  • His definition of life’s work — “a lifelong quest to build something for others that expresses who you are” — pairs with his one team maxim: “the reward for great work is more work.” And the closing story argues whole lives are downstream of small kindnesses: cousin Tim organ-transplanted him into Notre Dame’s social scene; first night, first bar, first girl he spoke to became his wife of 20 years.

Deep dive

1. Find a principle, not a goal — and expect it to take a decade to name

  • The episode’s frame: Patrick has refused interviews for five or six years, preferring to shine the light on others; this is Senra’s new show turned around on him. His principle, finally articulated: seeing not-yet-realized potential in a person creates an obligation — “to get to know them, to learn from them, to start introducing them to people… I don’t need to get anything out of it. What I get out of it is the thing.”
  • The source is Bret Victor’s talk “Inventing on Principle.” Victor’s principle was that digital creators should have instant feedback with their creation — collapse the gap between code and result. Patrick’s test for whether you’ve found yours: “you know you found your principle when it starts informing literally every decision you make every day with your time.” He warns it’s slow — “don’t get discouraged if you can’t name your principle an hour later” — his took a decade.
  • Before he had his own, he stole Victor’s: instant feedback became the primary design principle of the software in his last business, and “the business grew a lot because of the software” — “which just goes to show the power of a great principle.” He’s never met Victor: “If he’s listening, I’d love to meet him.”
  • A good principle generalizes: applied to his ~16-person team, the question becomes “who can I find and see something in… and make their career explode?” Investing, friendship, and his team — “a good principle can be applied everywhere.”

2. Goals put blinders on; everything good arrives from the periphery

  • His anti-goals stance is load-bearing, not aesthetic: “very talented people, when they set a goal, they tend to do it… and you know the road in front of you, and you have blinders on.” The essay “Growth Without Goals” — the most-read thing he ever wrote — came at 28, on the Stamford commute, triggered by writing letters to his unborn son (a tradition his father started for him): kids “don’t do what you tell them. They do what you do.”
  • The evidence he cites is his own history: “You were not the result of some goal that I was seeking” — Sam Hinkie texted him about Senra unprompted — “everything interesting I’ve ever done came out of left field.”
  • On introspection: a crippling childhood fear of death (“someday I would not exist and that just freaked me out… for decades”) drove years of philosophy, religious texts, and personality-test obsession. Once the principle clicked, the introspection stopped. Senra’s read, which Patrick accepts: “Introspection was the tool… you don’t need the tool once the job is done.”
  • The navigation heuristic he offers instead of goals: chase the feeling of being alive, not the meaning of life (a line he attributes to Alan Watts or possibly Joseph Campbell). The strange human fact: people “kind of know what makes them feel most alive and then they don’t do it most of their lives.” Why not? “They’ll give reasons that add up to ‘I’m afraid’” — original paths mean it’s all on you.

3. Bet on people before they deserve it — the data says that’s what kindness is

  • The tweet that drove Senra’s subscriber influx: Founders was paywalled with subscribers countable “on two hands” when Patrick posted “I never find new podcasts to listen to. I think David Senra’s Founders Podcast is excellent,” linking the Estée Lauder episode. Senra’s point: that instinct is rare — “I don’t think I would’ve done that. You didn’t see it as a competition.”
  • Patrick’s explanation reaches for data: someone on Twitter compiled the ~500 answers to his standing closing question, and about two-thirds were the same answer — “some person made a bet on me before I deserved it. They saw something in me that maybe I didn’t even see in myself.”
  • The worldview underneath came at 26, adrift (“I wasn’t that good at anything, and I was searching”), from a passage in the Upanishads that “felt like someone hit me in the face with a hammer”: “Those who feed the hungry protect me. Those who don’t are consumed by me.” From that moment: “the whole point of this is to help other people. That’s it. That’s the entire point of this existence.”

4. Judge the artifact, not the attributes — and leave breadcrumbs

  • The COVID-era Zoom story is the sharpest selection heuristic in the episode: a group of investors riffing on “attributes of great inventors” until one great retired investor’s face contorts — “Morons, who cares? Did they make a good invention?” If the invention is good, the inventor probably is. Patrick found Colossus’s editor-in-chief this way: Jeremy Stern’s Tablet profile of Palmer Luckey was the best profile he read, so he hired the person who made it.
  • Senra’s matching specimen, via Brent Beshore at lunch with Charlie Munger — “How do you and Warren find great CEOs?” “We just find somebody that is a great CEO and say, ‘Come do that for us.’” “But what about hiring for potential?” “We don’t do that.”
  • Inverted, it’s career advice: “put breadcrumbs out into the world… Pour a year of your life into making one amazing thing that people are amazed by, and amazing things will happen, I promise you. The internet is amazing at sharing something that is great.” Paired with Senra’s maxim — “there’s always room for great” (“so we don’t need any more music? We need less bad shit”) — and volume: find “the thing you just can’t help but do crazy high rep count of” and build a compounding curve off it.

5. The magazine thesis: scarce attention units, hard-to-copy product

  • The abstract frame is genuinely investor-relevant: “I’m very interested in how can I create and control valuable, scarce units of attention, and then dole those things out to the people that we believe in.” The cover insight came from almost buying an obscure magazine with huge names on its covers: “it dawned on me — people can’t say no to a cover. And so I tested that theory out and it was true.”
  • The quality bar comes from David Remnick’s New Yorker compilation: the best profiles pair “somebody doing a thing they’re obsessed with and a writer that is as obsessed with the person as the person is with the thing.” The Josh Kushner/Thrive profile became “one of these bizarre break-the-internet moments” — 45 minutes in, Patrick was still reading about the Holocaust family history, which Stern (himself a product of Holocaust survivors) could write because “it was also his family’s history.”
  • Why profiles became rare: “they’re really hard to make… the pay is terrible… it’s much cheaper and faster to make a stupid fucking TikTok than write a 50-page profile.” His counter-thesis is the junk-food analogy — most content is “optimized for us to want the most of it possible… obviously horrible for us” — and “the world is desperate for” the carefully made thing. He likes moats built from difficulty: “stuff that’s very hard to make and that’s singular, that can’t be easily copied,” including profiles started today for publication in ten years via annual lunches.
  • Every venture drew the same reception: the podcast, Canvas, the magazine — “literally everybody said it was a stupid idea.” His screen: “if it sounds like a good idea… you’re in a more competitive space. The key is stuff that sounds dumb but isn’t.” And he wants Colossus to outgrow the show: “a world where it’s no longer rate limited by my time and energy is much more exciting than a world where it’s me.” Senra’s read: “you’d like to be the guy behind the guy.” “That’s true.”

6. Learn, build, share, repeat — the whole career is one daisy chain

  • The practical case study: Canvas was built by stealing from three people — Daniel Ek on how to build software, Bret Victor on the design principle, Chathan Pudigunta at Benchmark on how to sell it — “and then not thinking too hard about what they tell me and just doing it and having it work.” Chathan gave demo feedback in Benchmark’s office with no investment stake, “just out of the goodness of his heart.”
  • The chain, told in full because it’s the anti-goals argument: reading thousands of books in his 20s → a monthly favorite-books email → the podcast’s first audience → the relationships that built and sold the software business → small checks → a Series A that spawned the fund → Positive Sum. “The whole thing is daisy-chained together because I loved reading fucking books in my 20s… If you had told me to list my goals when I sent that first email, none of those things would have been on my sheet.”
  • His model for growth without targets is lifting: progressive overload — “a little bit harder, a little bit more, go to failure” — without knowing where it takes you. And an honest caveat he insists on: he was born “on proverbial third base,” didn’t pay for college, and had the privilege to sit and read — “I think that’s important to acknowledge.”
  • The volume behind the interviewing craft: “I interview people once a week, but really I interview like 10 people a day… 40 or 50 times a week, which is not an exaggeration. Just, ‘Who are you? What’s your deal?’”

7. “Red on the color wheel”: the weakness Hinkie named

  • On a five-hour walk in Columbia, Missouri, Sam Hinkie described Patrick’s biggest weakness: “red on the color wheel” — voracious intensity when locked in, but “the moment that attention is focused elsewhere, I can whiplash around a lot.” Senra’s friends call it the Eye of Sauron: “if Patrick is focused on you, he will make shit happen” — Senra once flew to Greenwich to physically reclaim the attention.
  • Hinkie’s example: Patrick committed to Hinkie’s first fund; a month later, at docs time, he had to cut his check — “I have also launched a fund.” Hinkie: “A month ago you had never even thought about having a fund… and now it’s raised and done?” One left-field company investment became a fund in summer 2020. Patrick doesn’t defend it: “I don’t think this is a good thing… I realized, thanks to Sam, that I was whiplashing people.”
  • The neurological wrinkle, discovered about a year ago: he can’t visualize — “You can see things with your eyes closed? What are you talking about?” — plus “quite bad event memory. I don’t ever think about stuff in the past, like ever.” So a dropped enthusiasm isn’t just deprioritized; it’s genuinely never thought of again — “jarring for people that are signed on to do a thing.”
  • The repair is leadership-by-over-communication. His survey of everyone he knew for a definition of a great leader was won by Ravi Gupta: “It’s not hard. A great leader is someone that other people wanna follow.” Senra stacks the repetition case: Elon’s executives “mouthing the words along with me,” and Sol Price via Jim Sinegal — if you’re not spending 90% of your time teaching, you’re not doing your job. “Repetition doesn’t spoil the prayer.”

8. Clean fuel versus dirty fuel — Springsteen got out, LBJ never did

  • Senra’s six-month obsession, Springsteen’s autobiography, carries the episode’s psychological core: a man “psychopathically obsessed” with fame channels a terrible childhood environment into a world-historic work ethic, gets everything he wanted, and drops into the deepest depression of his life in his mid-30s. The pattern with women: “Why do you love me?… the fact that you love me means there’s something wrong with you, and I’m going to hurt you.” Twenty-five years of therapy, antidepressants, and the final realization: “work is a part of life. It is not my full life.”
  • The comparison Senra draws from Robert Caro: LBJ, seen literally running through Washington winter and summer because he’d finally reached the city of his dreams — same dirty-fuel source, no exit. “One is generative, one is unbelievably manipulative… So much in between these two stories.”
  • Senra’s verdict: “Dirty fuel works really well, but it consumes the person. I would far rather die nobody knowing who I am… but having people that could count on me.” His grandmother, who died at 99, banged the same drum every visit: “Congratulations on all the success. Who gives a shit? What are you doing for other people? That’s what I wanna know.” His conclusion: “the path out is others. Simple as that.”
  • The trap named precisely: money, power, fame are “worldly proxies” that become the chase once you taste them — versus the Upanishads’ abiding joy, “joy that doesn’t run out… as you use it, you get more of it. That will always guide you well, always. And money, power, fame will not.” On fame specifically: “I wish at the end of each of my episodes it, like, flashed people in the face” — Men in Black style — “and they forgot who I was.”

9. Life’s work, and the health claim worth flagging

  • His definition, which Senra makes him repeat: “a lifelong quest to build something for others that expresses who you are — all three parts are really important.” Most people, even great founders, aren’t doing theirs; his tell is Thomas Jefferson’s tombstone, which lists the Declaration and the University of Virginia but not the presidency. The one maxim his team uses: “the reward for great work is more work” — the right people’s “eyes go wide and they understand it immediately.”
  • The diligence application: his favorite founder question is “give me two hours — tell me your whole life story up until the point you founded your company.” Best story wins — originality, hardship, transformation. “Success in startups is the result of path dependency very often”; “the harder the business is to build, the harder it will be to copy”; transformation belongs to the customer.
  • Against Senra’s ordering of health-work-relationships (health first), Patrick offers a striking personal counter: years of serious health problems while doing everything right — daily logs, eating unbelievably well, “there’s no willy foofoo thing that I didn’t explore” — resigned to being “one of those people that’s gonna be sick.” Then: “it cannot be coincidence that when I finally started doing the thing I think I was meant to do and focused on the relationships, all of a sudden my health got better. The body keeps the score.” Stated as personal experience, not prescription.

10. The roles game, the list of 15, and Tim

  • A party game he swears by: write ten roles you play, discard them one by one to a final keeper. His father-in-law Dan — a very successful healthcare/insurance executive — kept “grandfather,” and lives it: “the Michael Jordan of grandfathers.” Patrick’s gloss: scope shrinking that narrow is “in some sense much smaller and in other sense the biggest possible thing you could do… that shit will ripple through history.” The related archetype: Bill Campbell, transformative for maybe five people, chasing nothing. “What if the only thing you were allowed to do in your life was help three people?”
  • His own keeper was “probably husband or father — or I probably cheated and said, ‘Can I have both?’” The generalization: you can’t go all-in for a thousand people, “but you can do it for 10 or 15. That list of people for whom I would do anything is my prized possession” — and if the feeling isn’t mutual, “that’s okay.”
  • The kindest-thing answer, finally turned on him: rejected from every college he applied to — all the very small envelopes arrived the same day — he reapplied, earned good grades, and transferred to Notre Dame, where third cousin Tim O’Shaughnessy “went so far out of his way to, like, organ-transplant me into his social circle,” down to calling ahead: “I’m sick, but Patrick’s coming out — show him a good time.”
  • Night one, Tim’s fake ID (5'4", blonde, blue eyes) got him into Boat Club — shut down three weeks later for exactly that — where the first girl he talked to, in the first bar, on his first night became his wife, Lauren: 20 years, now more of his life with her than without. Tim died tragically young. “Whole lives are downstream of simple, quick acts of kindness… Without Tim, my life doesn’t look anything like what it looks like today.”