Patrick O'Shaughnessy
Founder & CEO, Positive Sum · 1 appearance on the record.
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Patrick O'Shaughnessy is the founder and CEO of Positive Sum and host of the podcast Invest Like the Best, produced by Colossus. He previously served as CEO of O'Shaughnessy Asset Management and authored the book Millennial Money: How Young Investors Can Build a Fortune.
25statements → 5claims → 1claims resolved → 3.96/5average certainty → 1.84/5average debate potential → ≈4.0/5argument clarity, estimated → 15said about them ↓
0 supported 0 partly supported 1 contradicted 4 not checkable as stated how the 5 claims stand · each chip opens the sources
2 predictions · 3 assertions · 1 opinion · 14 insights · 5 disclosures · every statement was checked. The predictions and assertions are the 5 claims: statements the public record can support or contradict. 1 is resolved, and 4 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.
The record, in short
What the tape says about how Patrick argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.
Their most notable contradicted claim
Two-thirds of podcast guests say early bets were ultimate kindness
“Some person on Twitter or something went and compiled every answer, there's 500 answers or whatever, and categorized them and like made a pie chart of like what people say, and something like two-thirds of the answer to this question were the same, which was t…”
How they sound: not measured why? →
We measure speaking style by listening to the audio itself, and a fair number needs at least 2,000 words from one person on tape we have measured. There is too little of Patrick O'Shaughnessy on measured tape to publish a rate. This says nothing about how they speak.
Everything Patrick O'Shaughnessy said on David Senra that made the record, most notable first. Filter by type, assessment or year in the ledger →
O'Shaughnessy: Setting explicit goals blinds talented people to unexpected opportunities
“One of the reasons I don't like goals is I think very talented people, when they set a goal, they tend to do it. And that's why goals are interesting to lots of people is it's a great way to make progress. But I find it unexciting because the second you set so…”
O'Shaughnessy: Creators and entrepreneurs must ignore base rates to achieve outliers
“I think, like, screw base rates. I don't care what the, I never care what the base rate is. Like, the whole, the most interesting stuff is outliers by definition. So I don't care what happened to everybody else. I don't care if, you know, there's common pitfal…”
O'Shaughnessy: Online content is junk food and audiences crave crafted work
“The world is so sick of this crap just all day, every day. It's just crap. And it's, everyone makes the junk food comparison because it's a perfect comparison. Like junk food got to where it was because it's been optimized for us to want the most of it possibl…”
O'Shaughnessy: The best story wins, defined by originality, hardship, and transformation
“The best story always wins. And I actually spent the last couple of months, like, really trying to figure out what do I think best story means? And the best principles for a great story that I could come up with were originality, hardship, and transformation.”
O'Shaughnessy: Success typically pulls creators into branching into multiple businesses
“Most people that have achieved a level of success in their field or in their job that you have begin to The world, when that happens, pulls you into this branching exercise where you end up doing lots of different stuff. And that, you know, you end up monetizi…”
O'Shaughnessy: Inventing on principle means correcting violations to serve others
“The principle should be something that when you see it violated, it is your obligation to go correct it, and that that correction is an act of service for other people, not for yourself. It's not about you. And that's what makes the idea so powerful.”
O'Shaughnessy: Dirty fuel generates success but consumes people from within
“Dirty fuel works really well, but it consumes the person in a way that I would far rather die, you know, nobody knowing who I am with no worldly, you know, success, but having people that Could count on me, rely on me. I was faithful to, that I was loyal to.”
O'Shaughnessy: Jesse Beyroutey will be one of history's greatest investors
“A gentleman I spend a ton of time with now named Jesse Beirutti, who I am with basically every day, who also I think has no interest in fame or accolades or recognition, but I think is one of the great, will go down, I would predict as one of the great investo…”
O'Shaughnessy: The best business ideas sound dumb but aren't
“Like, if people say something's a good idea, I always get a little nervous, because if it's, if it sounds like a good idea, it just feels you're in a more competitive space, it's gonna be harder. I think the key is stuff that sounds dumb, but isn't.”
O'Shaughnessy: Colossus' written profiles will soon dwarf its podcast network
“I suspect it won't be long until that's much bigger than even the podcast, which itself is, you know, very, very big.”
O'Shaughnessy: New ventures should be differentiated and exceptionally hard to execute
“I would add on to that, like it should be different and really hard, like really hard to do.”
O'Shaughnessy: Magazine covers are the ultimate spotlight people cannot refuse
“Like, people can't say no to a cover. And so I tested that theory out and it was true. And I think what that means is it's like the ultimate form of spotlight and attention that you can give to somebody.”
O'Shaughnessy: Hire talent by searching publicly for the absolute best work sample
“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.”
O'Shaughnessy: Creating one truly amazing thing unlocks outsized opportunities via the internet
“If you create a single thing, not, it'll be 10 things, just one thing that people are amazed by. Put it, pour a year of your life into making one amazing thing that people are amazed by, and amazing things will happen, I promise you. Like the internet is amazi…”
O'Shaughnessy: Compounding career success stems from building on naturally high repetition counts
“What is the thing where you naturally have a lot of reps because you just like it? And find some, build off that, because there's this learning by doing concept, like, you get better at something just through being prolific in the thing, and most people have a…”
O'Shaughnessy: The reward for great work is the privilege to do more
“The reward for great work is more work, and I find that saying that maxim to the right person, like the kind of person I want to spend time with, they, their eyes go wide and they understand it immediately that the reward for great work is not money, power, fa…”
O'Shaughnessy: Devotion to a small circle rivals Elon Musk's business success
“And that is every bit as successful in my mind and in my book as Elon Musk or Jeff Bezos or, you know, pick the people that we all worship. In the business world, I'm amazed by them too, but there are flavors of success, and to me, that sort of devotion, even …”
O'Shaughnessy: Architecting life around picking and championing specific people
“I also kind of like picking sides. I like saying I like this person and by extension, I like them more than the other available options in this field or this industry or whatever. And I just get tremendous joy out of that. So now I'm architecting my life to ju…”
Two-thirds of podcast guests say early bets were ultimate kindness
“Some person on Twitter or something went and compiled every answer, there's 500 answers or whatever, and categorized them and like made a pie chart of like what people say, and something like two-thirds of the answer to this question were the same, which was t…”
O'Shaughnessy: Brett Victor's instant feedback principle drove asset management software growth
“I took his principle, not my own, but his principle of instant feedback and applied it as the primary design principle to software that I built in my last business, which worked really well. The software itself worked really well. The business grew a lot becau…”
O'Shaughnessy: Personal principle is fostering unrealized potential into existence
“It is trying to see enormous, like, not yet realized potential. And my principle is that is, when I do, it is my obligation. With nothing, maybe I invest, maybe, maybe I end up benefiting, but that's not the point. That it's my obligation to tell people about …”
O'Shaughnessy: Personal career accolades bring zero emotional gratification
“If I look back on my life, The sort of like wins that I've had, the things that if you were to write like a Wikipedia article about me would be like the accolades or the accomplishments. I don't care about those things. I don't think about them. When they happ…”
O'Shaughnessy: I dropped intense introspection after discovering my life's direction
“Once I have clicked into, I think, understanding what I want to do, I don't think about it at all. And now I have very little introspection left in my life. I used to be so obsessed with all of these personality tests and what they mean and psychology and seek…”
O'Shaughnessy: I cannot visualize mental images in my mind's eye
“If you close your eyes and try to visualize something, a red cardinal or something, there's a degree of how spec, how visually sharp that thing looks in your mind's eye when you close your eyes. For me, it's just black. I can't visualize anything. I can't see …”
The other half of the tape: Patrick O'Shaughnessy's own voice is left out of every number here. Other people bring the name up 13 times in 8 episodes on David Senra. 2 statements on the record name them. every mention, with the transcript →
Who brings them up most David Senra 10Jason Fried 2Strauss Zelnick 1
Statements about Patrick O'Shaughnessy, by other people (2)
Senra: Read late-life autobiographies because elderly subjects have no incentive to lie
“And this is why I like autobiographies and biographies so much, because in many cases, the person's, like, long past dead, or they're older, and they're just like, I'm writing this book when I'm 80, like, I have no, I'm not incentivized to lie, and, like, here…”
Every mention by year
tap a year for its mentions
2026 7 mentions in 5 episodes 1 per episode
- The Man Behind Grand Theft Auto 6: Strauss Zelnick
- Jason Fried: Your Only Competition Is Your Costs
- Building One of AI’s Fastest-Growing Companies | Mati Staniszewski, ElevenLabs
- The Company Apple Couldn't Kill | Spotify Co-CEO Gustav Söderström
- John Mackey: The Dropout Who Changed How America Eats
- every mention in 2026, scene by scene →
2025 6 mentions in 3 episodes 2 per episode
Appearances (1)
| Episode | Date | Speaking time |
|---|---|---|
| My Conversation With Patrick O'Shaughnessy, Founder of Colossus & Positive Sum | David Sen | Dec 21, 2025 | 1h 8m |