Patrick O'Shaughnessy, Colossus & Positive Sum | David Senra

O'Shaughnessy explains his organizing principle: finding talented but unknown people, developing relationships with them, and using all his resources to champion them. He describes how this principle emerged from a passage in the Upanishads at age 26 that fundamentally shifted his worldview to focus on helping others. This principle now informs every decision he makes, from investing to media to team building.

• •The kindest thing people cite is when someone 'bet on them first' before they deserved it - this became O'Shaughnessy's life mission
• •At 26, a passage from the Upanishads ('those who feed the hungry protect me') fundamentally changed his worldview to service-oriented
• •His principle: when he sees undiscovered talent, it's his obligation to help foster it and show the world what he sees
• •He gets more fulfillment from others' wins than his own accomplishments - this extends to portfolio companies, podcast guests, and team members
• •The principle should inform literally every decision you make with your time and be an act of service for others, not yourself

Senra recounts the pivotal moment when O'Shaughnessy tweeted about Founders podcast to his high-net-worth audience, causing an explosion of subscribers overnight. This story illustrates O'Shaughnessy's principle in action - he discovered quality content with minimal audience and immediately used his platform to champion it, fundamentally changing Senra's trajectory.

• •O'Shaughnessy tweeted 'I never find new podcasts to listen to. David Senra's Founders Podcast is excellent' when Senra had almost no followers
• •Senra was getting so few subscribers he received individual emails for each one - the next day his inbox was flooded
• •O'Shaughnessy's audience is 'one of the most insanely valuable in the world' in terms of average net worth
• •The 'Passion and Pain' episode they recorded together became a huge inflection point - 'lightning in a bottle'
• •O'Shaughnessy pushed Senra for years to start recording conversations before he finally did

O'Shaughnessy explains why he doesn't have goals and instead operates on principles, inspired by Bret Victor's 'Inventing on Principle' talk. He argues that talented people achieve their goals but miss opportunities in the periphery, while principle-based living allows for serendipity. The discussion covers how to find your principle and why it takes years to articulate.

• •O'Shaughnessy wrote 'Growth Without Goals' essay at 28 - he's not chasing any particular outcome or BHAG
• •Bret Victor's principle: digital creators should have instant feedback with their creation - this inspired O'Shaughnessy's approach
• •Goals create blinders; everything interesting in O'Shaughnessy's life 'came out of left field' not from goal pursuit
• •You know you've found your principle when it starts informing literally every decision you make every day
• •It took O'Shaughnessy over a decade to clearly articulate his principle - don't expect to name it quickly

O'Shaughnessy warns about the trap of chasing money, power, and fame instead of 'abiding joy' - the feeling of being alive that never runs out. He discusses how these worldly proxies for success are intoxicating but ultimately unfulfilling, while the feeling of being alive is renewable and should guide all decisions.

• •The Upanishads concept of 'abiding joy' - joy that doesn't run out, you get more as you use it
• •Money, power, fame are worldly proxies for success that become traps once you start getting them
• •These three things are 'intoxicating' - they feel really good at first but don't lead to sustained fulfillment
• •Chase the feeling of being alive, not traditional success metrics - this will always guide you well
• •O'Shaughnessy wishes he could use a Men in Black memory flash so people would forget who he is after interviews

O'Shaughnessy challenges the conventional wisdom that health comes first, sharing his experience of having severe health problems despite perfect diet and exercise. His health only improved when he got his work and relationships right, suggesting that doing what you love and having great relationships is the foundation of health.

• •O'Shaughnessy had 'tremendously bad health problems' for years despite eating well and working out daily
• •He tried 'everything' including keeping daily logs - nothing worked until he changed his work and relationships
• •When he finally started doing what he was meant to do and focused on core relationships, health magically improved
• •The body keeps the score - you can't fix health problems with just diet and exercise if work/relationships are wrong
• •Senra's three priorities: health, work, relationships - but O'Shaughnessy argues work and relationships enable health

Senra shares insights from Springsteen's autobiography about a man psychopathically obsessed with professional achievement who achieved everything he wanted, then fell into deep depression. Springsteen's realization that 'life is more important, work is part of life' and his 25-year therapy journey offers lessons about developing emotional skills alongside professional ones.

• •Springsteen had 'one of the most insane work ethics' and knew since age 15 what he wanted - worldwide fame and success
• •After achieving everything in his mid-30s, he dropped into the 'deepest depression of his life'
• •His parents had 'messed up his emotional well-being' - he was incapable of the relationships he desperately wanted
• •Pattern: would get close to women, then think 'why do you love me? I'm undeserving' and run away repeatedly
• •Went through 25 years of therapy and antidepressants to develop the skill set for what he actually wanted: family and deep relationships

The discussion explores the difference between 'clean fuel' (generative, love-based motivation) and 'dirty fuel' (negative, pain-based motivation). While dirty fuel works and drives many successful founders, it consumes the person. O'Shaughnessy advocates for working backwards from what you want to be true at the end of life.

• •Most founders in biographies were fueled by 'dirty fuel' - it works really well but consumes the person
• •O'Shaughnessy would 'rather die unknown' but with people who could count on him than achieve worldly success with dirty fuel
• •Senra is transitioning from pushing himself harshly to 'I push myself because I love it' - much nicer to himself now
• •Clean fuel: 'If I love it, I'll do it all the time. If I do it all the time, I'll get really good. Money comes as result of service'
• •Work backwards from what you hope is true at the end - simple heuristic for finding what to do

O'Shaughnessy explains the counterintuitive decision to launch Colossus magazine and write long-form profiles when everyone else is doing podcasts. He discusses how profiles are 'really hard to make' which makes them valuable, the power of giving someone a magazine cover, and why he hopes the magazine becomes bigger than his podcast.

• •Everyone said starting a magazine was a 'stupid idea' - if people say it's a good idea, O'Shaughnessy gets nervous because it means more competition
• •The key is 'stuff that sounds dumb but isn't' - magazines seem dead but long-form profiles are desperately needed
• •Discovered people 'can't say no to a cover' - it's the ultimate form of spotlight and attention you can give someone
• •Profiles take months or years to write, require huge investment, but create something singular that can't be easily copied
• •The Josh Kushner profile started with 45 minutes about the Holocaust - risky but essential to understanding the family's story

Both discuss their approach to finding talent: consume massive volume of the thing you want made, identify who made the best one, and hire them. This led O'Shaughnessy to Jeremy Stern after reading his Palmer Luckey profile in Tablet. They also cover Charlie Munger's advice: don't hire for potential, find someone already great and ask them to do it for you.

• •O'Shaughnessy read 'a million profiles' to find the best - Jeremy Stern's Palmer Luckey piece in Tablet was it
• •Investor's advice on finding great founders: 'Did they make a good invention? If the invention is good, the inventor is probably good'
• •Charlie Munger to Brent Beshore: 'We find somebody that is a great CEO and say come do that for us. We don't hire for potential'
• •If you're trying to get ahead: create ONE amazing thing people can find - pour a year into it
• •The internet is amazing at sharing something that is great - leave breadcrumbs of exceptional work

O'Shaughnessy reveals he hopes Colossus magazine becomes much bigger than his podcast because it means hiring more talented people, creating more content he can enjoy, and championing more people. This counterintuitive preference perfectly illustrates his core principle of service and championing others over personal recognition.

• •O'Shaughnessy gets most giddy receiving first drafts of profiles and investment research reports in Slack
• •He wants a world where he's 'not needed at all' because that means they're creating more and hiring more talented people
• •Hopes magazine expands beyond writing to documentary and convening people in small situations
• •A world where output isn't rate-limited by his time and energy is 'much more exciting' than one where it's just him
• •He'll always do interviews and hopes they get bigger, but vastly prefers the rest to dwarf what he does personally