WEBVTT

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Welcome to today's deep dive. I'm so glad you're

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joining us because today we are looking at Ray

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Dalio Oh, yeah, the billionaire founder of Bridgewater

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Associates exactly the world's largest hedge

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fund and you know our source today is a really

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comprehensive Wikipedia article covering his

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life his career his philosophies. But we have

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to talk about the warning banner. We absolutely

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have to talk about the banner. So right at the

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top of this Wikipedia article, there is this

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fascinating meta detail. Right. In April 2021.

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Wikipedia editors actually flagged the article.

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They slapped a warning on it saying it lacked

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neutrality and was written from a, quote, fan's

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point of view. Which is just, I mean, it's incredibly

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ironic. It really is. Yeah. Because this is a

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guy who built a $20 billion fortune on this strict

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philosophy of radical transparency. Right. The

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idea that you have to face the brutal, unvarnished

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truth of reality at all times. Yeah. But his

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own public biography was apparently too glossy.

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So our mission today is to strip away that fan

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bias, right? We want to deconstruct the man behind

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the myth. Find out how a kid from Queens actually

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built this financial empire. Exactly. And look

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at his frameworks. Figure out what they can teach

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you about navigating risk in your own life. OK,

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let's unpack this. So to understand Dalio's his

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later obsession with these really strict emotionless

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principles, we can't start with the billionaire

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in the suit. Right. We actually have to look

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at the absolute chaos of his early career. We

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start with a massive failure. Yeah. His origins

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do not scream Wall Street Kingmaker at all. He

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was born in Queens in 1949. And his dad was a

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jazz musician, right? An Italian -American jazz

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musician, playing clubs, just, you know, living

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entirely in the moment. Which is such a wild

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contrast. Think about it. The father thrives

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on improvisation. He reads the room, plays by

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feel. Completely unstructured. Exactly. And the

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son will eventually spend his whole life trying

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to, like, eradicate improvisation. He wants rigid

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algorithms. But young Dalio was already super

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into the markets. He actually worked as a clerk

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on the New York Stock Exchange floor. Got his

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MBA from Harvard Business School in 1973. Right.

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Which brings us to this really pivotal moment

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in 1974. Oh, the cattle ranchers? Yes. So he

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lands a job at a securities firm called Shearson

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Hayden Stone. And his whole job is advising cattle

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ranchers and farmers on how to hedge their risks

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using futures. Let's put you, the listener, in

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those shoes for a second. Imagine you own a massive

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cattle ranch in the 70s. You'd be terrified.

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Completely. You are terrified that beef prices

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might just plummet before you can even get your

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herd to market. Right, so you hire this young

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guy, Dalio, to lock in your prices using these

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financial contracts. So a sudden market swing

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doesn't just bankrupt your entire family. The

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pressure must have been insane. Oh, it's incredibly

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high stakes. You are directly responsible for

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people's survival, and Dalio is this hot shot

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young trader absorbing all this stress, and well,

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the tension just snaps. Spectacularly. I mean,

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it's New Year's Eve, 1974. Yeah. He gets drunk

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at a party, gets into an altercation, and he

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literally punches his boss in the face. Just

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unbelievable. And he's immediately fired, obviously.

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Obviously. Wall Street is not really known for

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being super forgiving about publicly assaulting

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your boss. Right. You'd think that's the end

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of his career in high finance. But he doesn't

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disappear. In 1975, he moves out to Wilton, Connecticut,

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and he sets up his own wealth advisory firm out

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of a converted barn. A literal barn. The literal

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barn. He calls it Bridgewater Associates. And

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here's the best part. He just takes his former

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corporate clients, those ranchers and farmers,

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with him to the barn. It's such a great story.

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He's like a rock musician, you know, getting

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kicked off a major label for trashing a hotel

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room. And then he just goes home, starts an indie

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garage band, and ends up buying the entire music

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industry. That is exactly what it's like, because

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his big break in that barn was eventually signing

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McDonald's. Wow. McDonald's. What's fascinating

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here is the irony of that whole trajectory. How

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so? Well, the man who becomes globally famous

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for corporate discipline and radical transparency,

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he started his empire because of a spectacular

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lack of professional discipline. Oh, that's true.

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It really begs the question, right? Did that

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early visceral failure you know, losing his job

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because anger overrode his logic, did that force

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him to build a system where emotions just couldn't

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get in the way? Like the barn became a laboratory

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to engineer human emotion out of the process.

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Exactly. He's sitting in this barn. He has no

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Wall Street credentials anymore. He can't rely

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on the prestige of a big firm. So he just has

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to rely on pure math. Right. Which forces him

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to build what he later claims is this infallible

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economic machine. And it works. Fast forward

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to 2005, and that barn operation is the largest

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hedge fund in the world. OK, so how does a barn

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become the biggest fund on Earth? They get there

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by launching two really distinct, massive strategies.

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The first one is in 1991. He introduces something

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called pure alpha. OK, and alpha in finance is

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like, it's the excess return, right? Yeah. Above

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the market baseline. Spot on. Alpha is the extra

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value you create, while beta is just whatever

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the broader market is doing. Right. So if the

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market goes up 10 % and you make 12%, that 2

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% is your alpha. Exactly. So with pure alpha,

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Dalio builds a system to just isolate that alpha.

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He's betting on the direction of different asset

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classes globally, completely untied from the

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stock market's overall performance. So it's super

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active? Very active. It's a zero -sum game trading

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aggressively to exploit tiny inefficiencies.

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But active trading is super risky, which I guess

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is why in 1996 he pioneers the second strategy.

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Right, the all -weather fund. Yeah. The All Weather

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Fund. This is the concept that became known as

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risk parity, right? Yes. And the mechanics of

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risk parity are brilliant. Can you break that

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down for us? Because I think people get confused

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by it. Sure. So normally when you or I try to

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balance our retirement portfolio, we think in

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dollar amounts. Like a traditional 60 -40 split.

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Yeah. 60 % of your money in stocks. 40 % in bonds.

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Exactly. But Dalio realizes that stocks are way

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more volatile in bonds. They carry way more inherent

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risk. Oh, I see. So even if the dollars are split

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60 -40. Your risk isn't. That 60 -40 split means

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your stocks might actually be carrying like 90

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% of your portfolio's total risk. Oh, wow. So

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if stocks tank, you're still completely exposed.

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Right. Risk parity changes the whole equation.

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Instead of splitting your capital, you split

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the volatility. Meaning you put less money into

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the risky stocks. Yes. Less money in stocks,

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more money in safe bonds. But then, to get the

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high returns you still need, you use leverage.

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You borrow money to juice the returns of those

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safe bonds until their risk level perfectly matches

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the stocks. That is wild. So no matter what the

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economic weather is doing, high inflation, deflation,

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a crazy recession, different parts of the portfolio

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counterbalance each other. You're totally insulated.

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And for a long time, the narrative was that this

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Bridgewater machine was practically clairvoyant.

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And 2007 was really the ultimate proof of concept

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for that, wasn't it? It was. Dalio's automated

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system started flashing red. They predicted the

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2008 global financial crisis way before the mainstream

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banking sector had any clue. I remember reading

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he coined a specific term for it in 2009, the

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D -process. Right, D -process. Let's clarify

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that for the listener because it's crucial. He's

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talking about deleveraging, a scenario where

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the whole economy is taken on way too much debt

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and suddenly everybody is forced to pay it back

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at the exact same time. While their assets are

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collapsing in value. Exactly. Like the subprime

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mortgages. It's this brutal deflationary spiral.

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And he wasn't just surviving the crisis. He was

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providing the mathematical framework to explain

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it. The supercomputer was working flawlessly.

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Or so we thought. Right. Here's where it gets

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really interesting. Fast forward to November

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2023. Ah, the New York Times report. Yes. The

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New York Times publishes this massive investigative

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report that just throws a huge wrench into this

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entire Bridgewater mythos. It's a profound wrench.

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What did they find? Well, the investigation claimed

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that the fund's legendary returns weren't actually

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driven by the sophisticated emotionless machine

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they'd been selling the public on for decades.

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Wait, really? Then what was driving it? According

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to the report, a huge portion of those investments

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were actually based on Ray Dalio's own personal

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gut feeling picks. His gut feelings. That is

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the exact opposite of an emotionless algorithm.

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It gets worse. The report alleged these choices

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were heavily informed by legally obtained insider

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information. From where? From his elite personal

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network of prominent government actors and policymakers

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around the world. Oh wow. So just backroom conversations?

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Essentially. Now, Dalio's legal team obviously

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pushed back hard. They threatened a multi -billion

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dollar lawsuit against the publisher, Macmillan.

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Claiming it was all fabricated. Yeah, they said

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the portrayal was completely inaccurate. But

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looking at this critically, it really forces

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you to re -evaluate the core narrative. I mean,

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I have to push back on the mythos here. Because

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if you build your whole reputation on radical

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transparency and the absolute superiority of

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this algorithmic system. Right. But your unprecedented

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success actually relies on your personal government

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connections and your own gut picks. Doesn't that

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completely invalidate the system? That's a very

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fair question. Like how transparent is a mathematical

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model if the real secret sauce is just who the

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founder is having dinner with at Davos? That

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is the crucial tension of modern structural success.

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He sold the world on this idea that if you just

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codify the right principles, feed them into an

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algorithm, you can objectively conquer the markets.

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But the reality might be way messier. Exactly.

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The 2023 controversy asks us to consider a harder

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truth. In a world completely obsessed with data

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and AI, how much of ultimate success is still

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just dictated by human access? Right, who you

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know. or they whisper to you behind closed doors.

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And your own personal intuition. It's almost

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like the jazz musician's improvisation sneaking

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back into the sun's super computer. Oh, that

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is a phenomenal way to frame it. You can try

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to build an emotionless machine in a barn, but

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eventually someone has to read the room. Yeah.

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But whether it was pure math or networking or

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some hybrid of both, you can't really argue with

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the results. No, the financial results were...

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Undeniably historic. To the tune of a 20 billion

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dollar personal fortune. It's staggering. It

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really is. He actually stepped down as co -CEO

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for a brief period, initiated this huge company

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-wide shakeup, and then officially stepped back

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in 2017. And then sold his last remaining shares

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in 2025. Right. Walked away from the daily operations

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with just an incredible amount of wealth and

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influence. And when you sit on 20 billion dollars,

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you get a very unique vantage point on the global

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stage. He definitely didn't just retire to a

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beach somewhere. No, not at all. He's positioned

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himself as a sort of philosopher king of macroeconomics.

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Yeah. And if you dive into his public statements,

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he has a very specific structural view of the

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world. For instance, his views on capitalism.

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Right. He argues that while capitalism is the

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best economic system we have, it desperately

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needs structural reform. He literally called

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wealth inequality a, quote, national emergency.

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He did. And he's also heavily focused on geopolitical

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shifts. Like back in 2020, he warned that observers

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shouldn't be blind to China's continued rise.

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Explicitly framing them as an emerging global

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superpower. Exactly. And he's codified this whole

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worldview into these incredibly dense, massive

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books. Oh, the books. Where do we even start?

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Well, there's principles. Life and work, which

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came out around 2011 and 2017. That one laid

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bare the really intense corporate culture he

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built at Bridgewater. Right. But then in 2021,

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he published The Changing World Order. And that

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was a massive pivot. Yeah, from corporate culture

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straight into global history. He analyzed hundreds

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of years of data to explain why empires like

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the Dutch, the British, the American -American,

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why they inevitably rise and fall based on debt

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cycles. And internal conflicts. And he just followed

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that up in 2025 with another New York Times bestseller,

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How Countries Go Broke. the big cycle. He went

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from advising cattle ranchers in a barn to writing

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historical templates for the collapse of nations.

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It's quite a leap. But honestly, amidst all this

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heavy macroeconomic theory, I am totally captivated

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by his personal quirks. The hobbies are wild.

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They are. The things he does with his time and

00:12:40.679 --> 00:12:42.700
his money off the block. Well, his philanthropy

00:12:42.700 --> 00:12:45.039
alone operates on a scale most people can barely

00:12:45.039 --> 00:12:47.240
comprehend. Right. He and his wife join the giving

00:12:47.240 --> 00:12:49.120
pledge. Committing to give away more than half

00:12:49.120 --> 00:12:51.700
their wealth. Overall, the Dalio Foundation has

00:12:51.700 --> 00:12:55.110
donated over five billion dollars. Five billion.

00:12:55.409 --> 00:12:58.549
They gave 50 million to launch the Dalio Center

00:12:58.549 --> 00:13:00.769
for Health Justice at New York Presbyterian.

00:13:00.830 --> 00:13:03.730
They pumped 185 million into Ocean X to protect

00:13:03.730 --> 00:13:05.870
marine environments. But then you look at his

00:13:05.870 --> 00:13:09.809
daily life and the contradictions are just incredible.

00:13:09.950 --> 00:13:12.929
Okay, lay them out. So he is a devoted practitioner

00:13:12.929 --> 00:13:15.559
of Transcendental Meditation. He says it's the

00:13:15.559 --> 00:13:17.500
single most important reason for his financial

00:13:17.500 --> 00:13:19.820
success. Okay. Pretty common for billionaires.

00:13:19.980 --> 00:13:22.539
Sure. But he's also an avid bow hunter. A bow

00:13:22.539 --> 00:13:26.200
hunter. Yes. And my absolute favorite detail

00:13:26.200 --> 00:13:29.220
from our source material, he owns a massive research

00:13:29.220 --> 00:13:33.580
yacht and a submarine. Submarine. A literal submarine.

00:13:34.120 --> 00:13:37.679
And he has used them to hunt for giant squids

00:13:37.679 --> 00:13:40.620
on the Discovery Channel. Wait. A giant squids.

00:13:40.879 --> 00:13:43.200
Yes. When you list it all out, it sounds completely

00:13:43.200 --> 00:13:45.240
disjointed. It really does. Like he meditates

00:13:45.240 --> 00:13:47.779
in absolute silence. He tracks animals through

00:13:47.779 --> 00:13:50.419
the woods with bow and arrow. He drops billion

00:13:50.419 --> 00:13:53.179
dollar submarines into the abyss to chase mythical

00:13:53.179 --> 00:13:55.720
sea creatures. And then he sits at a desk and

00:13:55.720 --> 00:13:58.379
writes 500 page treatises about sovereign debt

00:13:58.379 --> 00:14:01.629
cycles. How do you even reconcile all those different

00:14:01.629 --> 00:14:03.710
versions of the man? I don't know. How do you?

00:14:04.090 --> 00:14:06.250
Well, if we connect this to the bigger picture,

00:14:06.750 --> 00:14:10.029
a very clear unifying pattern actually emerges.

00:14:10.250 --> 00:14:12.169
Really? What's the common thread? Think about

00:14:12.169 --> 00:14:14.909
it. Whether he's dropping in a sub to track squid,

00:14:15.149 --> 00:14:17.029
sitting in a hunting blind waiting for a deer,

00:14:17.629 --> 00:14:19.750
or analyzing the rise and fall of the British

00:14:19.750 --> 00:14:23.409
Empire, Dalio views the entire world as a series

00:14:23.409 --> 00:14:26.789
of interconnected, predictable ecosystems. Whoa.

00:14:27.320 --> 00:14:29.279
I see where you're going with this. Everything

00:14:29.279 --> 00:14:31.679
is just a different type of system to him. Precisely.

00:14:31.840 --> 00:14:34.279
He believes everything operates in massive recurring

00:14:34.279 --> 00:14:36.559
cycles. So the squid is just part of a deep sea

00:14:36.559 --> 00:14:40.019
biological cycle. Exactly. The 2008 crash was

00:14:40.019 --> 00:14:42.179
just the inevitable turn of a long term debt

00:14:42.179 --> 00:14:44.879
cycle. The wealth inequality is a predictable

00:14:44.879 --> 00:14:47.259
symptom of late stage capitalism. That makes

00:14:47.259 --> 00:14:50.210
so much sense. His entire life's work, whether

00:14:50.210 --> 00:14:53.389
it's in nature or markets or history, it's all

00:14:53.389 --> 00:14:56.250
an attempt to step outside the chaos, observe

00:14:56.250 --> 00:14:58.269
the patterns from a detached vantage point, and

00:14:58.269 --> 00:15:00.789
just write down the rules. Wow. So what does

00:15:00.789 --> 00:15:03.490
this all mean? We started this deep dive looking

00:15:03.490 --> 00:15:07.090
at a kid from Queens with a jazz musician dad

00:15:07.090 --> 00:15:10.110
who blew up his early career by throwing a punch

00:15:10.110 --> 00:15:12.429
at a party. And we ended up dissecting the mind

00:15:12.429 --> 00:15:16.149
of a $20 billion philosopher who hunts sea monsters.

00:15:16.370 --> 00:15:19.899
Right. who debates his own algorithms against

00:15:19.899 --> 00:15:23.240
elite networking and tries to map the rise and

00:15:23.240 --> 00:15:26.240
fall of human civilization. It is an incredible

00:15:26.240 --> 00:15:28.879
evolution of character and strategy. It really

00:15:28.879 --> 00:15:31.000
is. But let's bring this back to you, the listener,

00:15:31.639 --> 00:15:33.460
because you don't need a hedge fund to apply

00:15:33.460 --> 00:15:35.659
these mechanics to your own reality. No, not

00:15:35.659 --> 00:15:37.779
at all. Think about that concept of risk parity

00:15:37.779 --> 00:15:40.049
we unpacked earlier. How can you apply an all

00:15:40.049 --> 00:15:42.070
-weather strategy to your own career? Right,

00:15:42.090 --> 00:15:44.230
instead of putting all your eggs in one volatile

00:15:44.230 --> 00:15:47.049
basket. Exactly. How can you split your volatility,

00:15:47.629 --> 00:15:49.850
diversify your skills, so that no matter what

00:15:49.850 --> 00:15:52.090
the economic weather does, you're insulated?

00:15:52.250 --> 00:15:55.250
Or think about his obsession with rules. If you

00:15:55.250 --> 00:15:57.669
are forced to write down your own personal principles,

00:15:58.029 --> 00:16:00.250
the actual algorithms you use to make your toughest

00:16:00.250 --> 00:16:03.409
decisions, could you do it? That is a powerful

00:16:03.409 --> 00:16:06.629
exercise for anyone to try. It is. But as we

00:16:06.629 --> 00:16:08.870
wrap up, I want to leave you with one final thought

00:16:08.870 --> 00:16:11.820
to mull over. Go for it. Let's trace our steps

00:16:11.820 --> 00:16:14.039
all the way back to the very first thing we discussed

00:16:14.039 --> 00:16:17.000
today. The Wikipedia banner. Yes, the Wikipedia

00:16:17.000 --> 00:16:20.879
warning banner from April 2021. The editors stepping

00:16:20.879 --> 00:16:23.259
in to flag the article about Ray Dalio because

00:16:23.259 --> 00:16:25.779
it read too much like a fan's point of view and

00:16:25.779 --> 00:16:28.100
needed to be stripped of its glossy filter. Right,

00:16:28.159 --> 00:16:30.779
the neutrality flag. Ray Dalio built his fortune,

00:16:30.980 --> 00:16:33.620
his reputation, his entire life philosophy on

00:16:33.620 --> 00:16:37.039
this concept of radical transparency, the absolute

00:16:37.039 --> 00:16:39.820
unflinching necessity of seeing the unvarnished

00:16:39.820 --> 00:16:43.019
truth, no matter how uncomfortable. Yet the very

00:16:43.019 --> 00:16:45.659
public encyclopedia page documenting his life

00:16:45.659 --> 00:16:48.779
was flagged for being too glowing, too biased,

00:16:49.080 --> 00:16:51.820
too perfectly crafted. It's such a striking contradiction.

00:16:52.100 --> 00:16:54.259
It leaves us with a deeply provocative question.

00:16:54.620 --> 00:16:57.639
If even the ultimate champion of radical transparency

00:16:57.639 --> 00:16:59.840
struggles to have his own story told without

00:16:59.840 --> 00:17:03.519
a glossy curated filter, how transparent are

00:17:03.519 --> 00:17:05.900
any of the narratives we consume every day? Oh,

00:17:05.900 --> 00:17:08.140
that's good. Or perhaps even more importantly,

00:17:08.460 --> 00:17:10.259
how transparent are the narratives we construct

00:17:10.259 --> 00:17:12.740
for ourselves? Man, that is a fascinating place

00:17:12.740 --> 00:17:14.559
to leave it. Thank you so much for joining us

00:17:14.559 --> 00:17:17.779
on this deep dive. Keep asking the hard questions,

00:17:18.200 --> 00:17:20.240
keep challenging the sources around you, and

00:17:20.240 --> 00:17:21.019
we'll catch you next time.
