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Patrick O'Shaughnessy - Creating on Principle (EP.455)

2026-01-20 - 128 min - source - Read full transcript
David Senra (host)Patrick O'Shaughnessy

Key insights

A principle beats a goal because it stays open to opportunity instead of putting blinders on.
Patrick has never set goals, citing his own essay 'Growth Without Goals.' He argues that talented people who set big goals tend to achieve them but lose openness to the unpredictable, off-path opportunities (like meeting David Senra) that produced everything he actually values. His only 'goal' is a principle: when he sees undiscovered talent, it is his obligation to help foster it, borrowed directly from Bret Victor's 'Inventing on Principle' talk.
principles-over-goals
Chase the feeling of being alive, not the meaning of life, as the signpost for what to pursue.
Citing a line he attributes to Alan Watts or Joseph Campbell ('we are not searching for the meaning of life but for the feeling of being alive'), Patrick treats moments of maximal aliveness as the best available heuristic for finding one's principle or path, more reliable than abstract goal-setting.
principles-over-goals
The main reason people don't pursue what makes them feel alive is fear of an original path.
Patrick argues that when he digs into why people avoid the thing they know makes them feel most alive, the answer reduces to fear: an original path means full personal responsibility and leaving a comfortable existence, which is genuinely uncomfortable even though it is the best story.
principles-over-goals
Money, power, and fame are traps because they are self-perpetuating in a way aligned work is not.
Patrick distinguishes 'dirty fuel' (chasing money, power, fame) from 'clean fuel' (the Upanishads' concept of abiding joy, which doesn't run out as you use it). Bruce Springsteen's autobiography is discussed as a case study: his childhood trauma converted into a work ethic that delivered fame and fortune, followed immediately by his deepest depression, resolved only through 25 years of therapy that redirected him toward family and relationships.
principles-over-goals
Whole lives are downstream of small, unreciprocated acts of kindness - the pattern shows up on both sides of this friendship.
Patrick credits his distant cousin Tim O'Shaughnessy's kindness in socially adopting him as a lonely transfer student at Notre Dame (which led him to meet his wife and closest friends) as his answer to his own signature interview question, 'what's the kindest thing anyone's done for you.' Separately, David describes Patrick subscribing to and promoting Founders by email when it had almost no listeners, before either of them had any audience, as one of the most formative acts of his career - a live example of Patrick's stated principle of betting on people before they've proven themselves.
relationships-and-mentorship
Health followed from getting work and relationships right, not the reverse.
Patrick had years of unresolved health problems despite obsessive diet and exercise discipline; he became convinced they resolved only once he found alignment in his work (his principle) and deepened his key relationships, suggesting health is downstream of purpose and connection rather than a precondition for them.
relationships-and-mentorship
'Life's work' is a useful evaluative lens for founders, not just a personal philosophy.
Patrick defines life's work as 'a lifelong quest to build something for others that expresses who you are,' and argues a founder's best diagnostic question is a two-hour walk through their life story before founding, because success is heavily path-dependent: a unique personal history, real hardship, and a clear customer transformation together predict both the quality and defensibility of a business.
leadership-as-service
The reward for great work is the privilege of doing more of it, not money, power, or fame.
This is the primary maxim Patrick's team operates by. He contrasts it with the now-diluted phrase 'life's work,' which he says almost nobody, including many great founders, actually lives - illustrated by Thomas Jefferson's tombstone listing three achievements and omitting the presidency.
leadership-as-service
Great leadership reduces to being someone other people want to follow, built mainly through over-communication and repetition.
Patrick cites Robbie Gupta's simple definition of a great leader and connects it to Elon Musk repeating the same four-part operating framework so often that his executives mouth the words along with him, and to Costco co-founder Jim Sinegal's mentor Sol Price, who held that a leader should spend 90% of time teaching. The underlying idea: repetition removes unspoken assumptions that otherwise compound into dysfunction.
leadership-as-service
Patrick's own biggest leadership flaw, per Sam Hinkie, was being 'red on the color wheel': intense focus that whiplashes collaborators when his attention shifts.
Hinkie illustrated this with a real incident: Patrick agreed to invest in Hinkie's first fund, then a month later - having launched his own fund in the interim without mentioning it - had to walk back the committed amount. Patrick says he's worked to counter this tendency by narrowing focus, avoiding the 'flavor of the month,' and deliberately over-communicating with people he works with.
leadership-as-service
Great profiles require a subject obsessed with their work and a writer equally obsessed with the subject - and that pairing is scarce because the format is economically unrewarding.
Patrick built Colossus's magazine strategy around a line from David Remnick's introduction to a New Yorker profile anthology. He argues profile writing largely died out not because demand disappeared but because it's slow, hard, and poorly paid compared to short-form content, which is exactly why well-made profiles stand out against algorithmically optimized 'junk food' media.
narrative-craft
Hire by outcome, not by abstractly defined traits: find whoever already made the single best example of the thing you need.
Patrick describes reading essentially every founder/investor profile he could find until he identified Jeremy Stern's Tablet profile of Palmer Luckey as the best one, then recruiting Stern directly; he generalizes this into a broader principle (echoing an investor friend's blunt 'who cares about attributes of a great inventor - did they make a good invention?') that observed output beats theorized qualification.
narrative-craft

Books referenced

Media referenced

Companies

Techniques and frameworks

Summary

This is an unusual Invest Like the Best episode: Patrick O'Shaughnessy, who has declined to be interviewed for five or six years, appears as the guest on David Senra's new show "David Senra," and the conversation is cross-posted here. The two have been close friends for years - Senra's Founders podcast grew in part because Patrick promoted it to his (at the time tiny) email list, and their earlier ILTB conversation, "Passion and Pain," is one both describe as a turning point. The episode functions as an extended, unusually candid attempt by Patrick to articulate an organizing principle he says took him roughly a decade to put into words.

That principle, borrowed in spirit from Bret Victor's talk "Inventing on Principle," is that Patrick has no goals - he actively avoids them - and instead operates from a principle: when he sees undiscovered talent, it is his obligation to help foster it, without needing anything in return. He traces this back to a passage in the Upanishads he read at 26 that reoriented his entire worldview toward service, and connects it to a survey he ran on his own podcast's closing question ("what's the kindest thing anyone's done for you"), where the dominant answer was some version of "someone bet on me before I deserved it." Goals, in his framing, create blinders; a principle keeps you open to the off-path opportunities - like meeting Senra, or the investor friend calls he took that led to launching his own fund - that actually produced everything he values. The heuristic for finding a principle, borrowed from a line he attributes to Alan Watts or Joseph Campbell, is to chase the feeling of being alive rather than an abstract meaning, and to notice that most people know what that feeling is and still don't pursue it, usually out of fear of an original, unproven path.

A long stretch of the conversation is a joint reading of Bruce Springsteen's autobiography as a case study in "dirty fuel" versus "clean fuel": ambition rooted in trauma delivered Springsteen exactly the fame and fortune he wanted and then dropped him into his deepest depression, resolved only through 25 years of therapy that redirected him toward marriage and family. Patrick contrasts this with Robert Caro's portrait of a young LBJ, whose comparably intense drive never became generative. Both men use this to interrogate their own wiring - Patrick recounts years of unexplained health problems that resolved, he believes, only once he found alignment between his work and his relationships, and both describe their current top three priorities as health, work, and relationships, in that order of dependency rather than importance.

The episode also functions as a working session on leadership and craft. Patrick discusses his own documented flaw - Sam Hinkie's description of him as "red on the color wheel," intensely focused but prone to whiplashing collaborators when his attention shifts, illustrated by a real story about renegotiating a fund commitment a month after making it - and the leadership maxims he's adopted to counter it: over-communicate, repeat the same message until it's boring, and treat "the reward for great work is more work" as the actual incentive that matters. On the media side, Patrick walks through why he built Colossus around long-form profiles: a line from David Remnick's New Yorker anthology (great profiles pair an obsessed subject with an equally obsessed writer) and his own habit of hiring by outcome - reading everything available in a category and recruiting whoever already made the best example, which is how he found Colossus's editor-in-chief, Jeremy Stern, through his Tablet profile of Palmer Luckey.

The conversation closes on relationships as the real ledger of a life. Patrick describes a formative act of kindness from a distant cousin, Tim O'Shaughnessy, who socially adopted him as a lonely transfer student at Notre Dame and indirectly introduced him to his wife - a story he credits as the reason his entire adult life exists in its current form. Both men return repeatedly to the idea that success measured by a small, devoted circle of people (a grandfather who is "the Michael Jordan of grandfathers," or Bill Campbell coaching a handful of executives at Google) is every bit as legitimate a form of achievement as commercial scale, and arguably more durable, since it ripples through generations in ways neither party can fully see.

Notable Quotes

"The principle should be something that when you see it violated, it is your obligation to go correct it, and that correction is an act of service for other people, not for yourself. It's not about you." - Patrick O'Shaughnessy

"We're not searching for the meaning of life, but for the feeling of being alive." - Patrick O'Shaughnessy (quoting Alan Watts or Joseph Campbell)

"The reward for great work is more work... it is the privilege to get to do more of this thing that I love doing." - Patrick O'Shaughnessy

"Mediocrity is always invisible until passion shows up and exposes it." - David Senra (on Walt Disney building Disneyland)

"Whole lives are downstream of simple, quick acts of kindness." - Patrick O'Shaughnessy