Annotations (19)
“There's this amazing talk called Inventing on Principle by Bret Victor. He espouses this idea that you should find a principle that you want to pursue. His principle was creators, digital creators should have instant feedback with their creation. My principle is when I see undiscovered talent, it is my obligation to get to know them, learn from them, introduce them to people. I don't need to get anything out of it. That's my life's mission: find a principle.”— Patrick O'Shaughnessy
Philosophy & Reasoning · Strategy & Decision Making · Leadership & Management
DUR_ENDURING
Universal organizing principle beats specific goals
“Life's work: a lifelong quest to build something for others that expresses who you are. All three parts are really important. The best way to figure this out in founders: give me 2 hours, tell me your whole life story up until the point you founded your company. Best story wins: originality, hardship, transformation. In the business context: I want someone that's lived a very unique path. Success in startups is the result of path dependency.”— Patrick O'Shaughnessy
Business & Entrepreneurship · Leadership & Management · Strategy & Decision Making
DUR_ENDURING
Life's work = lifelong + for others + expresses self
“I was 26 and I found this passage in the Upanishads. There's a line that basically says: those who feed the hungry protect me. Those who don't are consumed by me. It felt like someone hit me in the face with a hammer. It woke me up that the whole point of this is to help other people. That's it. That's the entire point of this existence. From that point forward, that's been my worldview.”— Patrick O'Shaughnessy
Philosophy & Reasoning · Psychology & Behavior
DUR_ENDURING
Upanishads: service is the point of existence
“The kindest thing anyone's ever done for you: I compiled 500 answers to this question from my podcast. Two-thirds of answers were the same: the kindest thing was some person made a bet on me first, answered the question before I deserved it, saw something in me that maybe I didn't even see in myself. They bet on me before others would. That was the answer to the kindest thing. My principle is: when I see undiscovered talent, it is my obligation to bet on them before anyone else does.”— Patrick O'Shaughnessy
Psychology & Behavior · Leadership & Management
DUR_ENDURING
Most impactful kindness: betting on people early
“If you want to hire someone for a thing, just go consume as much of the thing made by a million people as possible. Whoever made the best one, go for them. There was a Zoom conversation about attributes of great founders. Someone said: what are the attributes of a great inventor? This one investor's face started contorting. He was frustrated. He said: morons, who cares? Did they make a good invention? If the invention is good, the inventor is probably good.”— Patrick O'Shaughnessy
Leadership & Management · Strategy & Decision Making
DUR_ENDURING
Judge by output quality, not credentials
“I spent my 20s reading more than you can imagine. Thousands of books and profiles and everything. I started the podcast because I started to feel this awful feeling: this is happening in this weird, isolated way. It's just me and my notes. I'm not talking to anyone about these books. I wanted to start sharing. Learn, build, share, repeat. That 10 years of reading prepared me to be a good producer of profiles. My first love was reading. The love of reading became the email list.”— Patrick O'Shaughnessy
Business & Entrepreneurship · Strategy & Decision Making
DUR_ENDURING
Reading → sharing → podcast → business empire
“You know you've found your principle when it starts informing literally every decision you make every day with your time. It becomes universal. It can be applied everywhere: investing, friendship, your team. A good principle can be applied everywhere. One of the reasons I don't like goals is when you set some big goal, you kind of know what's going to happen because you go do it. But everything interesting I've ever done came out of the periphery, out of left field.”— Patrick O'Shaughnessy
Philosophy & Reasoning · Strategy & Decision Making
DUR_ENDURING
Principle test: does it guide every decision?
“I realized I was whiplashing people. I would be so excited and willing to galvanize people around an idea. Then I would change my mind and completely forget about the idea. I have quite bad event memory. I don't ever think about stuff in the past. I can change my idea and I literally never think about that thing again that I was so passionate about. That is jarring for people that signed on to do a thing.”— Patrick O'Shaughnessy
Leadership & Management · Psychology & Behavior
DUR_ENDURING
Overcommunication solves attention whiplash
“There's stuff that sounds dumb but isn't. If people say something is a good idea, I get nervous because you're in a more competitive space. The key is stuff that sounds dumb but isn't. Starting a magazine in 2025 sounds dumb. Magazines are dead or dying. But the thing underneath it was this desire to have more ways to do the thing we love: find people, learn about them, tell the world about them. There's always room for great. So many people said: we don't need another podcast.”— Patrick O'Shaughnessy
Strategy & Decision Making · Creativity & Innovation
DUR_ENDURING
Sounds dumb but isn't = best opportunities
“Tim O'Shaughnessy took it upon himself to organ transplant me into his social circle at Notre Dame. He would call ahead to his friends saying: I'm sick, I can't go out, but Patrick's coming out. Can you just show him a good time? Over and over again. He injected me into this community. Tim is the reason I met my wife. Met my best man. Through this act of over-the-top kindness, nothing in it for him, he was just doing the right thing. It set me up for the rest of my life.”— Patrick O'Shaughnessy
Psychology & Behavior · Culture & Society
DUR_ENDURING
Whole lives downstream of simple kindness acts
“Best story wins. The best principles for a great story are: originality, hardship, and transformation. Originality: people don't pursue original paths because they're fearful of the unknown. An original path by definition means it's all going to be on you. That's uncomfortable and hard. An original path usually means leaving a very comfortable current existence in a scary way.”— Patrick O'Shaughnessy
Creativity & Innovation · Psychology & Behavior · Strategy & Decision Making
DUR_ENDURING
Great story = originality + hardship + transformation
“I'm interested in stuff that's really hard to make. Things that are really hard to make are really interesting to me. People stopped doing profiles because they're really hard to make. They take time. The business model sucks. The pay is terrible. The world went a different direction: it's much cheaper and faster to make a stupid TikTok than write a 50-page profile about someone that's careful and intricate and well-written. The world is desperate for stuff like that.”— Patrick O'Shaughnessy
Strategy & Decision Making · Creativity & Innovation
DUR_ENDURING
Hard to make = hard to copy = moat
“The reward for great work is more work. That's my favorite maxim. It's the only one we use in my business with my team. The reward for great work is not money, power, fame. It is the privilege to get to do more of this thing that I love doing. You know you found your principle when saying that maxim to the right person makes their eyes go wide and they understand it immediately. I've never met anybody that's had that experience of pouring themselves into work that serves others and gone back.”— Patrick O'Shaughnessy
Leadership & Management · Psychology & Behavior
DUR_ENDURING
True reward: privilege of more work you love
“Learn, build, share, repeat. Do that until I die. I believe in that. That 10 years of reading prepared me to be a good producer of profiles because I've seen great, seen good, seen average, seen bad. My reps are very high. What is the thing where you naturally have a lot of reps because you just like it? Find and build off that. There's this learning by doing concept: you get better at something just through being prolific in the thing.”— Patrick O'Shaughnessy
Creativity & Innovation · Strategy & Decision Making
DUR_ENDURING
Find your natural high-rep activity, compound it
“Sam Hinkie said I'm red on the color wheel. When I'm interested in something, I am intense, voracious, aggressive. I have a skill at making things happen when I'm interested in them. The other side is that the moment attention is focused elsewhere, I can whiplash around a lot and change my opinion. This is known as the Eye of Sauron: if Patrick is focused on you, he will make shit happen. But if it's elsewhere, you're not. The example: Sam was raising his first fund and I was going to invest.”— Patrick O'Shaughnessy
Psychology & Behavior · Leadership & Management
DUR_ENDURING
Intensity strength becomes whiplash weakness
“The most read thing I ever wrote was called Growth Without Goals. I'm not a goals person. I don't have a big, hairy, audacious goal. I have no goals. If I have a goal in the abstract sense, it's just this thing over and over and over again: find undiscovered talent, get to know them, learn from them, start introducing them to people. When I see undiscovered talent, it is my obligation to do this thing. I don't need to get anything out of it. What I get out of it is the thing. That's the point.”— Patrick O'Shaughnessy
Philosophy & Reasoning · Leadership & Management · Psychology & Behavior
DUR_ENDURING
Process over outcome; principle over goal
“A great leader is someone that other people want to follow. That's it. What is shared in common amongst people that others want to follow: they are hypercommunicative with those people. They're consistent. They lead from the front. They take risk, they take arrows for the team, they communicate like crazy with the team. If something's changing, they overcommunicate it. They're honest.”— Patrick O'Shaughnessy
Leadership & Management · Psychology & Behavior
DUR_ENDURING
Leader = someone others want to follow
“If you create a single thing, not 10 things, just one thing that people are amazed by, put a year of your life into making one amazing thing that people are amazed by, amazing things will happen. I promise you, the internet is amazing at sharing something that is great. Put breadcrumbs out into the world so people see it and are amazed by it. Put stuff out in the world that people can find. We just find somebody that is a great CEO and say, come do that for us. Show, don't tell.”— Patrick O'Shaughnessy
Creativity & Innovation · Strategy & Decision Making
DUR_ENDURING
One amazing thing > many mediocre things
“Close your eyes and visualize a red cardinal. There's a degree of how visually sharp that thing looks in your mind's eye. For me, it's just black. I can't visualize anything. I can't see anything. I discovered this a year ago. The other side of that sword is when I'm focused on something like here right now, I am not thinking about other stuff. It's just all of this.”— Patrick O'Shaughnessy
Psychology & Behavior
DUR_CONTEXTUAL
Aphantasia = extreme present-moment focus
Frameworks (2)
Inventing on Principle
Using a Core Principle to Guide All Life Decisions
Rather than setting specific goals, identify a single guiding principle that represents what you believe should exist in the world. This principle becomes your obligation: when you see it violated, you must act to correct it. The principle informs every decision, creates optionality rather than rigidity, and allows serendipitous opportunities to emerge from the periphery. Test validity by asking: does it apply across all domains of life? Does it guide daily decisions? Does it create energy rather than drain it?
Components
- Identify the Violation
- Define Your Obligation
- Test Universality
- Validate Through Action
- Maintain Optionality
Best Story Wins
Evaluating Founders Through Originality, Hardship, and Transformation
When evaluating founders or any life's work, assess through three dimensions: originality of the path taken, hardship overcome in pursuit, and transformation created for others. Success in startups is path-dependent; unique experiences create unique advantages. Ask founder for 2-hour life story before discussing the company. The combination of non-obvious background + significant obstacles + customer transformation predicts both defensibility and impact.
Components
- Request the Full Life Story
- Assess Originality
- Measure Hardship
- Evaluate Transformation
Mental Models (17)
Work as Reward
PsychologyFor the right person, the reward for great work is not money, power, or fame—it's the privilege to do more of that work. This is a filter for identifying who you want to spend time with. When you say 'the reward for great work is more work' to someone, watch their eyes: if they go wide with recognition and excitement, you've found your person. If they look confused or disappointed, they're optimizing for external rewards. This reveals intrinsic vs. extrinsic motivation and predicts whether someone can sustain life's work.
In Practice: O'Shaughnessy describing his team's core maxim and how it filters for the right people
Demonstrated by Leg-po-001
Red on the Color Wheel
PsychologySome people have binary attention: when focused on something, they're intensely focused, voracious, aggressive, able to make things happen. But when attention shifts, they can whiplash dramatically, forgetting previous commitments and galvanizing around the new thing. The strength (intensity) becomes the weakness (inconsistency). This is different from being distractible; it's about depth of focus creating blind spots elsewhere. The solution: (1) narrow focus to fewer things, (2) overcommunicate with those affected by attention shifts, (3) build systems that don't rely on sustained attention.
In Practice: O'Shaughnessy relating Sam Hinkie's observation and the 'Eye of Sauron' nickname from friends
Demonstrated by Leg-po-001
Hard to Make, Hard to Copy
Strategic ThinkingSeek to create things that are very hard to make, because things that are hard to make are hard to copy. This creates a natural moat. People stopped doing long-form profiles because they're hard: they take months, require trust, pay poorly. But that difficulty is exactly why they're valuable and defensible. Inverse: if it's cheap and fast to make (TikTok), it's cheap and fast to copy. The world is desperate for carefully crafted things but few people will do the work because the difficulty is the point—it's both the deterrent and the moat.
In Practice: O'Shaughnessy explaining why he started Colossus magazine and why difficulty is a feature
Demonstrated by Leg-po-001
Path Dependency in Startup Success
Strategic ThinkingSuccess in startups is often the result of path dependency: a unique set of experiences led to you being the right person to solve this problem. The 'overnight success' is actually decades of path-specific learning. When evaluating founders, ask for full life story before company discussion. Look for: (1) Unique path no one else took, (2) Lessons learned that others don't have, (3) Why THIS person is uniquely positioned for THIS problem. The originality of the journey predicts the defensibility of the solution.
In Practice: O'Shaughnessy explaining his founder evaluation process and 'best story wins' framework
Demonstrated by Leg-po-001
Always Room for Great
Strategic ThinkingIgnore arguments about market saturation. There's always room for great. People say 'we don't need another podcast'—but we don't say 'we don't need any more music.' We need less bad stuff, not less stuff. Quality is never saturated. The key: be so good that 'sounds like a bad idea' (starting a magazine in 2025) becomes 'obviously brilliant' in retrospect. Don't compete on category; compete on quality. The world will always share and reward great, no matter how 'crowded' the category appears.
In Practice: O'Shaughnessy defending the decision to start Colossus magazine against 'magazines are dead' objections
Demonstrated by Leg-po-001
One Amazing Thing > Many Good Things
Strategic ThinkingPut a year of your life into making ONE amazing thing people are amazed by, and amazing things will happen. The internet is unbelievable at sharing great work. Don't spread yourself across ten things; focus on one and make it undeniable. This is both a filtering mechanism (people who see it understand your capability) and a signaling mechanism (breadcrumbs). You're not trying to do a lot; you're trying to do one thing so well it can't be ignored. Quality compounds; mediocrity doesn't.
In Practice: O'Shaughnessy explaining his approach to finding talent and how he found Jeremy Stern by reading one exceptional profile
Demonstrated by Leg-po-001
Principle Over Goals
Decision MakingReplace specific outcome goals with guiding principles that inform all decisions. Goals create tunnel vision and rigidity; principles create peripheral vision and optionality. When you set a goal, you know the endpoint and often miss better opportunities. When you follow a principle, opportunities emerge from unexpected directions. Test: does this principle apply across all life domains? Does it guide daily decisions? Does it create energy?
In Practice: O'Shaughnessy explaining his essay 'Growth Without Goals' and Bret Victor's 'Inventing on Principle' talk
Demonstrated by Leg-po-001
Sounds Dumb But Isn't
Decision MakingThe best opportunities sound like bad ideas. If everyone agrees something is a good idea, you're late and it's competitive. Seek ideas where consensus is 'that's dumb' but deep analysis reveals it's not. Starting a podcast in 2014: people said it's dumb. Starting a magazine in 2025: people say it's dumb. Both were/are right because the thing underneath (championing people through deep profiles) was valuable but the surface-level analysis (podcasts are niche, magazines are dying) was wrong. If you get nervous when people say it's a good idea, you're onto something.
In Practice: O'Shaughnessy describing his reaction when people validate vs. criticize his ideas
Demonstrated by Leg-po-001
Judge by Invention, Not Inventor Attributes
Decision MakingWhen hiring or evaluating people, don't ask about attributes (hardworking, smart, gritty). Ask: did they make a good invention? If the invention is good, the inventor is probably good. This cuts through credential inflation and interviewing theater. Charlie Munger to Brent Beshore: 'How do you find great CEOs?' Answer: 'We find somebody that IS a great CEO and say come do that for us.' Don't hire for potential; hire for demonstrated output quality. Consume 1,000 examples of the thing you want made, find who made the best one, hire that person.
In Practice: O'Shaughnessy recounting Zoom conversation about founder attributes and Munger's advice to Brent Beshore
Demonstrated by Leg-po-001
High Rep Count Compounds
MathematicsWhat is the thing you naturally do a crazy high rep count of? That's probably where you should build your compounding curve. Volume creates learning: you get better at something through being prolific. Most people have a natural high-rep activity (following their sports team, reading, gaming). The question is: can you channel that natural prolificacy toward something valuable? O'Shaughnessy read thousands of books naturally; that volume gave him pattern recognition that made him a good podcast host, which led to everything else.
In Practice: O'Shaughnessy explaining how 10 years of reading prepared him for everything that followed
Demonstrated by Leg-po-001
Daisy-Chained Compounding
MathematicsEach success creates the platform for the next success. The chain is non-linear and unpredictable. Reading -> email list -> podcast -> business introductions -> software company -> exit -> small checks -> investment firm -> larger fund. None of this was planned; each link created the next. You can't see the chain in advance, which is why goals-based planning fails for compound paths. Instead, optimize for: (1) Do work you love, (2) Do it visibly, (3) Remain open to peripheral opportunities. The chain will form.
In Practice: O'Shaughnessy tracing his career path from reading books to running investment firm
Demonstrated by Leg-po-001
Simple Kindness Compounds Through Generations
MathematicsWhole lives are downstream of simple acts of kindness. Small actions compound through generations. Tim O'Shaughnessy's kindness to Patrick -> Patrick meets his wife -> Patrick's kids exist -> Patrick's kids behave differently because of their grandfather's influence -> that ripples forward. One person's choice to be kind to a transfer student created an entire family line and career trajectory that wouldn't exist otherwise. The compounding of kindness is non-linear and immeasurable but perhaps the highest-impact thing you can do.
In Practice: O'Shaughnessy telling the story of Tim O'Shaughnessy's over-the-top kindness as a transfer student
Demonstrated by Leg-po-001
Betting on People Before They Deserve It
PsychologyThe most impactful kindness is believing in someone before others do, before they've 'proven' themselves. From 500 podcast answers to 'what's the kindest thing anyone's done for you?', two-thirds said: someone bet on me early, saw something in me I didn't see in myself, answered the question before I deserved it. This creates compounding loyalty and transforms trajectories. The key is timing: betting BEFORE evidence forces you to rely on pattern recognition and intuition, not credentials.
In Practice: O'Shaughnessy analyzing pattern from 500 podcast guest answers and connecting to his own story with Tim O'Shaughnessy
Demonstrated by Leg-po-001
Fear as Originality Inhibitor
PsychologyWhen you drill people on why they don't pursue what makes them feel alive, all reasons add up to fear. Original paths are scary because: (1) they're on you alone, (2) they mean leaving comfortable existence, (3) they're unknown by definition. Most people choose conventional paths not because they want them but because they fear the unknown. The absence of originality is often the presence of fear. Inverse question: what would you do if you weren't afraid?
In Practice: O'Shaughnessy explaining why people don't pursue original paths as part of 'best story wins' framework
Demonstrated by Leg-po-001
Overcommunication as Leadership Fix
PsychologyWhen you have a tendency to shift attention rapidly or change direction, the solution is not to stop doing that (if it's your nature) but to overcommunicate. Great leaders are hypercommunicative: they repeat, they clarify, they update, they make their thinking transparent. This prevents unspoken assumptions from accumulating. Ari Emanuel's deal principle: overcommunicate. The problem isn't the change; it's the silence around the change that creates whiplash for others.
In Practice: O'Shaughnessy describing how he solved his 'whiplash' problem and Ari Emanuel's approach
Demonstrated by Leg-po-001
Learn, Build, Share, Repeat
TimeSimple compounding loop: Learn something -> Build something with that knowledge -> Share what you built -> Repeat. Each cycle feeds the next. Learning gives you material to build. Building gives you something to share. Sharing attracts people who help you learn more. The loop accelerates over time if you do it consistently. O'Shaughnessy: read books (learn) -> started email list (build) -> shared favorite books (share) -> got podcast audience (repeat). This became his entire career via compound effects.
In Practice: O'Shaughnessy describing his 20s and how the simple loop compounded into his entire career
Demonstrated by Leg-po-001
Unpredictable but Inevitable Compounding
TimeWhen you love something and do it prolifically over years, unpredictable but inevitable good things happen. You can't predict WHAT will happen, but you can predict SOMETHING will happen. This is why goals fail for long-term paths: the specific outcome is unknowable, but the general direction of accumulation is reliable. Trust the process, not the plan. O'Shaughnessy couldn't have predicted any specific career outcome at 25, but the accumulated reps in reading + sharing guaranteed something good would emerge.
In Practice: O'Shaughnessy reflecting on how none of his current reality was predictable 15 years ago
Demonstrated by Leg-po-001
Connective Tissue (2)
Eye of Sauron from The Lord of the Rings
The Eye of Sauron is an all-seeing, intensely focused gaze that sees everything within its field but cannot see everywhere at once.
Discussing Sam Hinkie observation about O'Shaughnessy being red on the color wheel
The Upanishads: Those who feed the hungry protect me; those who don't are consumed by me
Ancient Hindu text from the Upanishads articulates the principle of service as protection and self-preservation.
O'Shaughnessy describing his transformation at age 26, reading the Upanishads
Key Figures (9)
Sam Hinkie
8 mentionsFormer GM of Philadelphia 76ers, Investor
Bret Victor
4 mentionsComputer Scientist
Tim O'Shaughnessy
3 mentionsCousin (Third Cousin)
Charlie Munger
2 mentionsVice Chairman of Berkshire Hathaway
Reece Dukka
2 mentionsInvestor (Private)
Ari Emanuel
2 mentionsCEO of Endeavor
Chetan Puttagunta
2 mentionsPartner at Benchmark
Ravi Gupta
1 mentionsInvestor/Executive
Brad Jacobs
1 mentionsSerial Entrepreneur (Founded XPO, United Rentals, others)
Glossary (2)
Upanishads
LITERARY_ALLUSIONAncient Hindu scriptures, part of Vedas; philosophical teachings thousands of years old
“I was 26 and I found this passage in the Upanishads”
aphantasia
DOMAIN_JARGONInability to voluntarily create mental images in one's mind
“I can't visualize anything. I discovered this a year ago.”
Key People (2)
Bret Victor
Computer scientist known for talk Inventing on Principle
Ari Emanuel
(1961–)CEO of Endeavor, owns UFC/IMG/WME
Concepts (3)
Inventing on Principle
CL_PHILOSOPHYBret Victor's framework: find a principle and make it your obligation to create it
path dependency
CL_ECONOMICSConcept that outcomes are shaped by the sequence of prior events and decisions
compounding
CL_ECONOMICSProcess where gains from an asset generate their own gains; accelerating growth non-linearly
Synthesis
Dominant Themes
- Principle-based life design vs. goal-based planning
- Service to others as organizing principle
- Championing undiscovered talent as life's work
Unexpected Discoveries
- O'Shaughnessy has aphantasia
- 500 podcast answers to kindest thing question: two-thirds said someone bet on them early
Cross-Source Questions
- How do other legends describe their organizing principles vs. goals?
Processing Notes
This is rare meta-content: a podcast host being interviewed about his own principles and methods.
Synthesis
This is rare meta-content: a podcast host being interviewed about his own principles and methods.