Patrick O'Shaughnessy
Founder & CEO, Positive Sum · 4 appearances 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.
45statements → 16claims → 14claims resolved → 79%fully supported → 3.96/5average certainty → 2.13/5average debate potential → ≈4.5/5argument clarity, estimated → 24said about them ↓
11 supported 1 partly supported 2 contradicted 2 not checkable as stated how the 16 claims stand · each chip opens the sources
1 prediction · 15 assertions · 4 opinions · 17 insights · 8 disclosures · every statement was checked. The prediction and assertions are the 16 claims: statements the public record can support or contradict. 14 are resolved, and 2 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 supported claim
O'Shaughnessy: Momentum forecasts fundamental growth better than valuation multiples
“What fascinates me about this is momentum does a better job of forecasting future fundamental growth than price does. So the highest momentum decile has better future fundamental growth than the most expensive, let's say PE decile or free cashflow yield decile…”
Their most notable contradicted claim
O'Shaughnessy: OSAM has almost zero portfolio overlap with AQR and LSV
“Our overlaps with other quants are shockingly low. Like we have this little cool program that we can show people this on the fly and they won't believe us. Like they'll ask about AQR and LSV and these other great managers, you know, really, really, really stro…”
Expressed certainty vs assessment result
weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet
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 Capital Allocators that made the record, most notable first. Filter by type, assessment or year in the ledger →
O'Shaughnessy: Pure quantitative strategies fail on concentrated portfolios
“If you're going to build a concentrated portfolio of a handful of positions, you can't do quant. It can't be pure quant. The stats don't work. You need to build a pretty diversified portfolio for a pure quant approach to make sense.”
O'Shaughnessy: Quant methods will never fully replace relationship-driven private equity
“Then your relationship with the seller, your skill in negotiation and deal structure, all of these things are critical and Again, can quant help inform some of that? Probably, but I don't think it's ever going to completely eat the whole thing.”
O'Shaughnessy: Quants typically avoid sector-specific data in favor of broad cross-sectional metrics
“Typically quants don't do deep industry sector specific
Data sets outside of like financials, which has been like a common problem for quants. Quants typically are looking for something you can compare cross-sectionally across the entire population of stocks.”
O'Shaughnessy: 4x Free Cash Flow Signals Distress in Public Equities, Not Private
“And, you know, when he first told me that he was buying businesses at a little bit north of four times free cashflow, you know, I kind of laughed. I thought, okay, like, so they're going out of business in three years. I mean, in the public markets, that multi…”
O'Shaughnessy: Best quant researchers are defined by extensive failure experience
“The best way to know that someone's going to be an effective and efficient researcher going forward into the future is that they know what not to do. And I think the only way to do that is to build up that experience of failure through time.”
O'Shaughnessy: OSAM failed to make factor timing work despite massive research effort
“We have burned an insane amount of our time Capital, human capital, stress, just every kind of capital trying to make this work, and it has not.”
O'Shaughnessy: Predictive modeling will get easier, shifting advantage to input data
“I believe that the predictive modeling part of this is going to get easier and easier. So what that means is what you put into those models is of critical importance.”
O'Shaughnessy: Borrow Costs and Volatility Eliminate Quantitative Short Paper Alpha
“Most of the stuff that screens as screaming shorts and in a paper portfolio works incredibly well. You have incredible problems with borrow availability, with borrowing cost, which often instantly removes the paper alpha and with volatility.”
O'Shaughnessy: 10-year real equity returns strongly inversely correlate with Shiller P/E
“When you look at the correlation Correlation between the current Shiller P.E. And the future 10 years of real returns in the market, it's very high. It's something like .7 or point, maybe even higher than that.7. So pretty reliably, what that means is if you b…”
O'Shaughnessy: Shiller P/E at 30 marks only the third time ever
“And we're at 30 today. Only the third time ever at 30 today.”
O'Shaughnessy: Zero fund-of-funds fees would not have won the Buffett bet
“If the fund to fund fees had been zero, you still would have lost.”
O'Shaughnessy: Alpha in financial markets depends strictly on relative skill
“Really all that matters in markets is relative skill. That if you've got, you know, 10 PhDs in a room, maybe 3040 years ago, that meant you were going to earn enormous alpha. But now everyone has those 10 PhDs, and they're fighting against each other. It's a r…”
O'Shaughnessy: DFA investors suffered a smaller behavior gap than S&P investors
“They've done an amazing job of convincing their investor base that they need to hold these strategies for the long term. Now, obviously, that works out well for DFA as a business, because they've got incredibly sticky money, but it has also worked out very wel…”
O'Shaughnessy: Key Investment Factors Historically Succeeded in Only 60-70% of Single Years
“In our research, luckily, those categories are honestly straightforward and simple. They're things like valuation, things like momentum, quality, return of capital. They're not crazy concepts. You just have to apply them with a lot of discipline, and I think t…”
O'Shaughnessy: OSAM Measures Momentum Across 3-12 Month Windows and Adjusts for Volatility
“What's fascinating about pure price momentum and the way that we think about this is three, six, nine, 12 month trailing windows of total return versus pierce. We think we should also care about the volatility of the momentum.”
O'Shaughnessy: OSAM Uses Machine Learning to Predict Specific Events Like Dividend Cuts
“So as a result, we have started to focus more on applying these techniques to focus on something like a dividend cut. Let's use that as an example. Build a model that just forecasts or predicts dividend cuts, and that's it.”
O'Shaughnessy: OSAM Has Seven External Research Partners, Including Jesse Livermore
“We now have seven of these people. It started with a very well-known anonymous writer who goes by Jesse Livermore online. He was sort of our pilot case.”
O'Shaughnessy: OSAM team spent three full years cleaning primary dataset
“We once spent three full years, the entire team spent three full years just cleaning and scrubbing data in our primary data set.”
O'Shaughnessy: OSAM Failed Three Times Attempting Short Strategies Internally
“We've done it with our own capital three times and failed miserably each time, not an absolute return sense, but certainly an opportunity cost sense because it's been during this great run up. So we've lost a lot of return with our own capital trying to do thi…”
O'Shaughnessy: Average Shiller P/E sits near 16-17, shifting higher post-1980
“Historically speaking, the average Shiller P.E. Is probably 1617, something like that. But there's definitely two regimes, and one is sort of pre-early 19 eighties, and one is post. And the average post, 19 eighties, is much higher.”
O'Shaughnessy: Constellation Software operates like a disciplined Berkshire for software
“Effectively what that is, is a, like Berkshire, an almost decentralized collection of software companies. So the parent Constellation, forgetting the CEO's name and his team are basically buying up individual assets, not, not micromanaging them. And they're ki…”
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 22 times in 17 episodes on Capital Allocators. 2 statements on the record name them. every mention, with the transcript →
Who brings them up most Ted Seides 12Morgan Housel 2Josh Brown 2Tom Lydon 1Khe Hy 1Jenny Heller 1Gavin Baker 1David Rosenthal 1
Statements about Patrick O'Shaughnessy, by other people (2)
Housel: Outlier Founders Like Musk and Bezos Are Tortured, Not Ambitious
“Patrick said the phrase that he would use to describe their personality is not driven by It's not ambitious. It's tortured. They wake up every morning tortured that they are not more successful, bigger, richer than they are. And I think that's true for virtual…”
Baker: A high-IQ social following sharpens investment ideas and drives venture deal flow
“Our friend Patrick O'Shaughnessy has said having a big
High IQ following is actually a superpower, and it really is. So I think for sharpening your ideas, it's incredible. Then there's a whole nother dynamic. It really matters for deal flow.”
Every mention by year
tap a year for its mentions
2026 1 mention in 1 episode
2025 2 mentions in 2 episodes 1 per episode
2024 5 mentions in 3 episodes 2 per episode
2022 1 mention in 1 episode
2021 5 mentions in 5 episodes 1 per episode
- Jennifer Heller – Beginner's Mind with Professional Wisdom at Brandywine (Capital Allocators, EP.211)
- Crypto for Institutions 4: Ari Paul – Exploiting Inefficiencies in Crypto Trading (Capital Allocators, EP.183)
- Crypto for Institutions 3: Seth Ginns – Investing Beyond Bitcoin (Capital Allocators, EP.182)
- Crypto for Institutions 2 – Michael Sonnenshein – A Path to Entry (Capital Allocators, EP.181)
- Crypto for Institutions 1: Eric Peters – The Macro Case for Bitcoin (Capital Allocators, EP.180)
- every mention in 2021, scene by scene →
2018 3 mentions in 2 episodes 2 per episode
Appearances (4)
| Episode | Date | Speaking time |
|---|---|---|
| Ted with Patrick O'Shaughnessy – Lessons from the World's Elite Money Managers (Capital Al | Mar 22, 2021 | 9m |
| Patrick O'Shaughnessy – O'Shaughnessy Asset Management (First Meeting, EP.01) | Jun 10, 2019 | 59m |
| Deep Dive into Hedge Funds (Capital Allocators, EP.34) | Dec 18, 2017 | 23m |
| The Bet with Buffett (Capital Allocators, EP.05) | May 2, 2017 | 21m |