WEBVTT

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Welcome back to the Deep Dive. Today we are opening

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up a file on a figure who I think is just genuinely

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misunderstood. I completely agree. And I don't

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mean that in some kind of, you know, oh poor

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billionaire way. I mean that the public image

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of him, the perception, is so often diametrically

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opposed to what the data actually shows. We are

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talking about Jack Dorsey. It is such a fascinating

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case study. I mean, usually when we profile the

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giants of Silicon Valley, you know, the founders

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who hit that multibillion dollar tier, we see

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a very specific psychological profile. Right.

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We see the empire builder, the relentless drive

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to centralize, to acquire, to build the biggest,

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baddest walled garden possible. You look at a

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Zuckerberg, you look at Gates back in the 90s.

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It's all about consolidation of power. Exactly.

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The narrative is always I built the castle and

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I own. the keys but dorsey is he's weird he's

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an outlier yeah he built two massive castles

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twitter and square which of course is now block

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and for the last what five or six years he seems

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completely obsessed with melting down the keys

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and just handing out the scrap metal to strangers

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that is the paradox that's the central enigma

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we have to unpack today you have a man who is

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what 49 years old now 49 worth roughly 3 .8 billion

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dollars as of mid 2025. this is a person who

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fundamentally shaped how the world communicates

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and and how it transacts money yet if you look

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at his current obsession this whole freedom technology

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phase It's all about dismantling the very structures

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that made him powerful and rich in the first

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place. So what is it? That's the question we

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have to get to. Is this some kind of guilt? Is

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it a new galaxy brain strategy? Or, and this

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is the interesting one to me, is it actually

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the most consistent thing he's ever done? I think

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it's the third one. And to understand that, we

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have to get past the headlines. Oh, yeah. The

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beard, the ice baths, the silent retreats. We

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have to ignore all that for a minute and actually

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look at the source code. And we've got a massive

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stack of sources here. Biographies, corporate

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filings from the early days of Odeo, even the

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technical architecture of the early Twitter back

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end. And of course, the white papers for the

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new protocols he's funding. And when you read

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through all of that, a really clear picture emerges.

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You realize you can't possibly understand Twitter

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and you definitely can't understand. his fascination

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with Bitcoin without first understanding taxicabs.

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This is what you call the dispatch theory. It

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is the unifying theory of Jack Dorsey. It all

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comes back to dispatch. Okay, so let's start

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right there. Part one, the origin story. Yeah.

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Because before he was a tech mogul, before any

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of that, he was just a kid in St. Louis with

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a police scanner. That's exactly it. St. Louis,

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Missouri, born in 1976. And it was a very traditional

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Catholic upbringing. He went to Bishop Duberg

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High School. Pretty standard stuff on the surface.

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But inside the house, it was a little different.

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His father, Timothy, he wasn't just some generic

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engineer. He worked on mass spectrometers. Right.

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And let's just pause on that for a second, because

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mass spectrometer is one of those terms we all

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hear and we just kind of gloss over it. It sounds

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complicated. It is complicated, but what it does

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is simple to understand. It takes a messy reality,

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a substance, and it breaks it down into its most

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precise data -driven components. It tells you

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exactly what something is made of. It's all about

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granularity. Precisely. It's about converting

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the physical world into pure, hard data. And

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his mother, Marcia, was a homemaker. So she was

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providing that stable home base for this very

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observant kid. And he was observant because he

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had to be, right? He had a speech impediment

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when he was young. He was shy. Very shy. So instead

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of talking, he just listened. And what he listened

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to was the city. The pulse of the city itself.

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Through the radio waves. Yeah, he became obsessed

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with maps, but not static maps. He didn't care

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about a paper map. He cared about dynamic maps.

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By the time he was 14, he was glued to police

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scanners, emergency frequencies, taxi dispatch

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channels. Now, most people, I think, listen to

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scanners for the drama. You know, there's a fire

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on Fifth Street or there's a robbery in progress.

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They want the story. They want the narrative.

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Jack didn't care about the narrative at all.

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He cared about the routing. He was listening

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to the syntax of the city. The system. The system.

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Think about what a dispatch system actually is.

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You have hundreds of these autonomous nodes moving

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around. Police cars, ambulances, couriers, taxis.

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They're all operating independently. But they're

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all reporting back. They're all reporting back

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to a central authority with these very short...

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Very structured bursts of data. Unit 1, 1023.

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Unit 5, en route to Mercy Hospital. Cab 7, heading

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to Lambert Airport. It's just a constant stream

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of two things, state and location. That's it.

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It's a real -time database of the physical world.

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And he wasn't just listening. He started writing

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software on his early computers to visualize

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this. He wanted to see the little dots moving

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on a map on his screen. He was trying to convert

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the chaotic noise of the radio into a clean visual

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interface of the city's pulse. That's such a

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crucial insight. He wasn't interested in why

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the ambulance was going somewhere. He was just

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interested in the raw fact of its movement and

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the efficiency of that movement. Exactly. And

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that obsession basically drove his entire academic

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path or, well, his detours from it. He started

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at the Missouri University of Science and Technology.

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Then he transferred to NYU in 1997. Which makes

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total sense. If you're obsessed with dispatch,

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New York City is your mecca. It's the ultimate

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dispatch city. The sheer density of couriers,

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taxis, delivery services. It's unlike anywhere

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else in the U .S. at that time. He wanted to

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be at the heart of the system. But he never actually

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finished, did he? Nope. The classic Silicon Valley

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dropout trope. He left one semester short of

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graduating. And we should probably clear something

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up here. There was a persistent rumor. for years

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that he went to Cornell. Oh, right. I've heard

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that. He's had to correct the record on that

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personally. He never went to Cornell. It was

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Missouri, S &amp;T, then NYU, then dropout. But even

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before he dropped out, he wasn't exactly, you

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know, going to frat parties. He was coding. He

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was trying to get into the system for real. He

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was. And he actually hacked his way into a job

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in a, you know, white hat kind of way. He found

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a security vulnerability on the website of a

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major New York dispatching company. Which one

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was it? A company called Dispatch Management

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Services, run by a guy named Greg Kidd. So Jack

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finds this hole, and instead of exploiting it,

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he emails the chairman, Greg Kidd, and basically

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says, hey, your front door is unlocked. I know

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how to fix it. That's a bold resume. Here is

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how I broke into your house. Now hire me to install

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the security system. And it worked. Kid was impressed.

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He brought Jack on, and that eventually led him

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to move out to California. By 2000, he's in Oakland,

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and he founds his first real startup. And the

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goal was? To dispatch couriers, taxis, and emergency

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services using the web. Now you have to put yourself

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in the year 2000. There's no iPhone, no app store.

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GPS is still this bulky, expensive thing, mostly

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for military and maritime use. So the technology

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wasn't really there yet to support the vision.

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The vision was way ahead of the tech. We've seen

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his notebooks from that era. He was sketching

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out these ideas for what he called frictionless

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service markets. He had diagrams of networks

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for medical devices reporting their status, courier

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networks. What's the core idea of frictionless

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there? He wanted to remove the human dispatcher

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entirely. He was thinking, Why does a guy in

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a call center have to tell the taxi where to

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go? The software should just be able to match

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the supply with the demand instantly. That is

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literally the core pitch for Uber, just a decade

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too early. It was Uber without the hardware to

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support it. So that company didn't take off.

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The infrastructure just wasn't ready. But during

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this period of sort of failing and thinking,

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he had this crossover idea. He was looking at

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two popular things at the time, AOL, Instant

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Messenger, AIM, and LiveJournal. The golden age

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of the away message. He loved the away message.

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Bird pizza, listening to Radiohead at the gym.

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He had this flash of insight. He realized an

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away message is just a dispatch update for a

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human being. It's state and location again. Exactly.

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It's the same pattern. And he wondered, why can

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I only show this status to my buddy list? Why

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can't I just dispatch my life, my status to the

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entire world? He wanted to turn every person

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into one of the little dots on a St. Louis map.

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He wanted to visualize the pulse of humanity

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the same way he visualized the pulse of the ambulances.

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But again, the idea just sort of sat on a shelf.

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It was a sketch in a notebook for years. He had

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bills to pay. Which brings us to 2006. and a

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failing podcast company audio audio it was a

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podcasting startup co -founded by noah glass

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and evan williams now evan williams is a key

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figure here he'd already founded blogger and

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sold it to google for a ton of money he was basically

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silicon valley royalty And Odeo was supposed

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to be his next big thing. Right. The idea was

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to make it super easy for anyone to record and

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share a podcast. But then in 2005, Apple completely

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torpedoed their business model. Right. They released

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iTunes 4 .9 with built -in podcast support. They

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ate Odeo's lunch. Suddenly their entire reason

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for being was redundant. So the company was just

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drifting. They were burning through cash. Morale

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was in the toilet. So Ev Williams says, OK, everyone

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break up into teams. Let's have a hackathon.

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Brainstorm something, anything to save the company.

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And that's when Jack dusts off the old dispatch

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idea. He pitches it to his little group, which

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included Noah Glass and a designer named Biz

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Stone. He describes a service that uses SMS simple

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text messaging to broadcast short status updates

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to a small group of friends. He called it 20TR.

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With no vowels, which was very trendy at the

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time. Flicker. Things like that. A fairy web

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2 .0. Oh. And we have to talk about the technology

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here because the limitations of 2006 literally

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define the product for its first decade. This

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wasn't an app you downloaded from an app store.

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There was no app store. It was all based on SMS.

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You would send a text message from your Nokia

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or your Motorola Razr to a short code number

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like 4044. Now, the global standard protocol

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for SMS messaging has a hard character limit.

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160 characters. 160 characters. That is a fundamental

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constraint in the GSM cellular network layer.

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It's not a design choice. It's a physical limitation

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of the pipe. So they needed to reserve some of

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those characters for the username for routing

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the message. Exactly. They decided to reserve

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20 characters for the username and commands,

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which left 140 for the actual content of the

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message. So that creative constraint that artists

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and designers love to talk about, the famous

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140 characters. It wasn't an artistic choice.

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It was just a bandwidth limitation. It was a

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technical necessity. Yeah. But it had this incredible

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side effect. It forced brevity. It forced people

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to communicate in headlines. It stripped everything

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down to the bare essentials. So Jack and Diz

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Stone, they build the prototype. In two weeks.

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They hacked it together. It was raw. It was simple.

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And initially, nobody at Odeo got it. The feedback

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was brutal. Who cares what you're doing right

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now? Why would I want to know you're eating a

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sandwich? This is just narcissism. To be fair,

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if you look back at the very first tweets, it

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was mostly, I am eating a sandwich. Jack's first

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tweet was, just setting up my TweetTR. It was.

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But then something happened. An earthquake hit

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San Francisco. And suddenly, people weren't tweeting

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about their lunch. They were tweeting, did you

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feel that? Power's out on my street. Everyone

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OK. It became a real -time information network.

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It became a dispatch system for reality. And

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as it started to grow, as users started using

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it in these unexpected ways, the infrastructure

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just began to crack. It couldn't handle the load.

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Which brings us to the era of the fail whale.

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Oh, that iconic image. The friendly looking white

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whale being lifted up by a flock of little orange

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birds. Yeah. It was cute, but what it represented

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was a catastrophic failure of engineering. What

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was actually happening under the hood when you

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saw that screen? This is so important because

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it really speaks to the challenges of scaling

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centralized systems. The early version of Twitter

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was built on a framework called Ruby on Rails.

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Now, at the time, Rails was very new and very

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popular for building websites quickly. But it

00:12:14.159 --> 00:12:16.059
wasn't built for this kind of scale. It wasn't

00:12:16.059 --> 00:12:18.360
optimized for the kind of massive, read -write

00:12:18.360 --> 00:12:20.940
-heavy database load that Twitter was generating.

00:12:21.259 --> 00:12:23.500
It's what's known as a fan -out problem. Break

00:12:23.500 --> 00:12:25.419
that down for us. What's a fan -out? Okay, so

00:12:25.419 --> 00:12:27.740
if I have just one follower and I send a tweet,

00:12:27.840 --> 00:12:30.460
the database has to perform one simple write

00:12:30.460 --> 00:12:33.700
operation. Here's the tweet. Put it in my follower's

00:12:33.700 --> 00:12:36.850
timeline. Easy. But what if I'm a celebrity with

00:12:36.850 --> 00:12:39.789
a million followers? When I send a tweet, the

00:12:39.789 --> 00:12:42.169
system has to fan that tweet out and update a

00:12:42.169 --> 00:12:43.990
million different timelines or at least their

00:12:43.990 --> 00:12:47.309
indexes almost simultaneously. So every popular

00:12:47.309 --> 00:12:49.710
tweet was like a denial of service attack on

00:12:49.710 --> 00:12:52.090
their own database. Essentially, yes. The database

00:12:52.090 --> 00:12:54.230
locking was a nightmare. They were constantly

00:12:54.230 --> 00:12:56.429
in firefighting mode, just trying to keep the

00:12:56.429 --> 00:12:59.009
site online. The fail whale was up more than

00:12:59.009 --> 00:13:01.169
the service was, it felt like. And this technical

00:13:01.169 --> 00:13:04.009
chaos leads directly to the first major... turning

00:13:04.009 --> 00:13:07.789
point in Jack's career, his ousting, his firing.

00:13:08.029 --> 00:13:10.370
It does. The official narrative from the board

00:13:10.370 --> 00:13:13.950
in 2008 was that Jack was an absentee CEO. Evan

00:13:13.950 --> 00:13:15.690
Williams and the other board members, they looked

00:13:15.690 --> 00:13:17.470
at the constant server crashes, they looked at

00:13:17.470 --> 00:13:19.549
the complete lack of a revenue model, and then

00:13:19.549 --> 00:13:21.190
they looked at Jack's calendar. And they saw.

00:13:21.759 --> 00:13:24.860
They saw yoga classes. They saw fashion design

00:13:24.860 --> 00:13:27.220
courses at a local apparel arts school. They

00:13:27.220 --> 00:13:30.240
saw him leaving the office at 6 p .m. sharp every

00:13:30.240 --> 00:13:33.019
day to go learn how to make skirts and draw patterns.

00:13:33.360 --> 00:13:35.620
Okay, now, from a strictly corporate governance

00:13:35.620 --> 00:13:38.720
perspective, if your billion -dollar startup

00:13:38.720 --> 00:13:41.840
is literally on fire every single day, leaving

00:13:41.840 --> 00:13:44.429
early to go sew is... It's not a good look. It

00:13:44.429 --> 00:13:46.049
looks terrible. It looks like you don't care.

00:13:46.590 --> 00:13:49.210
But from Jack's perspective, which he's explained

00:13:49.210 --> 00:13:52.909
since, he was trying to understand craft. He's

00:13:52.909 --> 00:13:54.690
always been obsessed with the aesthetics and

00:13:54.690 --> 00:13:57.049
the utility of a product. He has this famous

00:13:57.049 --> 00:13:59.529
metaphor where he compares Twitter to a good

00:13:59.529 --> 00:14:03.129
pair of jeans. Utilitarian, durable, gets better

00:14:03.129 --> 00:14:05.309
with age. Right. And he thought that by learning

00:14:05.309 --> 00:14:07.549
a physical craft like fashion design, he could

00:14:07.549 --> 00:14:09.429
better understand how to build a better, more

00:14:09.429 --> 00:14:11.570
durable digital product. He thought it would

00:14:11.570 --> 00:14:14.889
make him a better CEO. The board strongly disagreed.

00:14:15.100 --> 00:14:17.320
They fired him. Well, they did the polite Silicon

00:14:17.320 --> 00:14:19.639
Valley thing. They transitioned him to chairman

00:14:19.639 --> 00:14:22.639
of the board, which is a powerless ceremonial

00:14:22.639 --> 00:14:25.039
title. It's the nice way of saying get out of

00:14:25.039 --> 00:14:27.980
the way and let the adults handle this. Evan

00:14:27.980 --> 00:14:30.980
Williams took over as the full time CEO. So Jack

00:14:30.980 --> 00:14:33.779
is in exile. But this exile period is really

00:14:33.779 --> 00:14:35.980
interesting because he doesn't just go off and

00:14:35.980 --> 00:14:38.539
sulk. He's still the chairman. He's still involved.

00:14:38.899 --> 00:14:40.980
And this is when the whole State Department story

00:14:40.980 --> 00:14:43.990
happens, isn't it? It is. This is 2009. The Green

00:14:43.990 --> 00:14:46.669
Revolution is erupting in Iran. Massive street

00:14:46.669 --> 00:14:48.830
protests are breaking out to dispute the results

00:14:48.830 --> 00:14:51.490
of the presidential election. The Iranian government,

00:14:51.710 --> 00:14:54.509
as you'd expect, clamps down hard on state media,

00:14:54.629 --> 00:14:57.509
on cell service. But the Internet is still sort

00:14:57.509 --> 00:14:59.799
of trickling through. And Twitter becomes the

00:14:59.799 --> 00:15:02.120
main organizing tool. It becomes the primary

00:15:02.120 --> 00:15:04.539
command and control network for the resistance.

00:15:04.960 --> 00:15:07.700
People are coordinating protests, sharing videos

00:15:07.700 --> 00:15:10.179
of police brutality, getting the word out to

00:15:10.179 --> 00:15:12.720
the world. It was the first time we really saw

00:15:12.720 --> 00:15:15.220
the term Twitter revolution enter the lexicon.

00:15:15.360 --> 00:15:17.379
And right in the middle of all this, Twitter

00:15:17.379 --> 00:15:20.519
had scheduled some server downtime. Yes, ironically.

00:15:21.279 --> 00:15:23.460
to fix some of the very same database issues

00:15:23.460 --> 00:15:26.539
that got Jack fired. They had a maintenance window

00:15:26.539 --> 00:15:28.100
scheduled. They were going to take the entire

00:15:28.100 --> 00:15:30.779
service down for a few hours. And that's when

00:15:30.779 --> 00:15:33.779
a strictly mid -level official at the U .S. State

00:15:33.779 --> 00:15:36.600
Department named Jared Cohen sends an email to

00:15:36.600 --> 00:15:39.679
Jack Dorsey. And what did the email say? It essentially

00:15:39.679 --> 00:15:42.220
said, please, please do not take the site down

00:15:42.220 --> 00:15:45.100
right now. The protesters in Iran are using it

00:15:45.100 --> 00:15:49.840
to organize, to report, to stay alive. Wow. That

00:15:49.840 --> 00:15:52.080
has to be a pivotal moment. That's the moment

00:15:52.080 --> 00:15:54.340
Twitter stops being just a quirky tech company

00:15:54.340 --> 00:15:57.320
and starts being a genuine geopolitical actor.

00:15:57.480 --> 00:16:00.000
Absolutely. Jack gets the email. He forwards

00:16:00.000 --> 00:16:01.960
it to the right people at Twitter and they delay

00:16:01.960 --> 00:16:03.539
the maintenance. They keep the service running.

00:16:03.679 --> 00:16:06.379
And I think that moment planted a huge seed in

00:16:06.379 --> 00:16:08.860
his head. He realized that this little dispatch

00:16:08.860 --> 00:16:11.139
system he built wasn't just for sandwiches and

00:16:11.139 --> 00:16:13.559
earthquakes. It was a powerful tool for freedom.

00:16:13.779 --> 00:16:16.750
But, and this is the crucial part. It was a tool

00:16:16.750 --> 00:16:18.929
for freedom that he and a small group of people

00:16:18.929 --> 00:16:21.450
in San Francisco controlled. He had the switch.

00:16:21.669 --> 00:16:23.970
He had the power to turn it off or keep it on.

00:16:24.110 --> 00:16:26.090
The benevolent dictator problem. Exactly. And

00:16:26.090 --> 00:16:27.929
while he was pondering that massive philosophical

00:16:27.929 --> 00:16:30.789
problem, he went out and built another billion

00:16:30.789 --> 00:16:33.330
-dollar company from scratch. Which brings us

00:16:33.330 --> 00:16:36.669
to part three. Building Block, or as everyone

00:16:36.669 --> 00:16:40.110
knew it then, Square. And once again, the origin

00:16:40.110 --> 00:16:42.549
story starts with a simple dispatch problem.

00:16:42.789 --> 00:16:45.919
A failed transaction. It does. It's 2009. Jack

00:16:45.919 --> 00:16:47.700
is out of the day -to -day operations at Twitter.

00:16:48.000 --> 00:16:50.279
He reconnects with an old friend from St. Louis

00:16:50.279 --> 00:16:52.820
named Jim McKelvey. McKelvey had actually been

00:16:52.820 --> 00:16:55.299
his boss at one of his first programming jobs.

00:16:55.440 --> 00:16:57.820
And McKelvey had pivoted into a new career, right?

00:16:57.960 --> 00:16:59.980
Yeah, he'd become a high -end glass artist, a

00:16:59.980 --> 00:17:03.279
glassblower. And he calls Jack completely frustrated

00:17:03.279 --> 00:17:05.960
because he'd just lost a $2 ,000 sale for one

00:17:05.960 --> 00:17:09.690
of his glass faucets. Why? What happened? The

00:17:09.690 --> 00:17:11.910
potential customer only had an American Express

00:17:11.910 --> 00:17:14.630
card, and McKelvey, as a small artist, couldn't

00:17:14.630 --> 00:17:16.910
get a merchant account that would accept Amex.

00:17:16.910 --> 00:17:19.349
It was too expensive, too complicated. The customer

00:17:19.349 --> 00:17:21.910
just walked away. So Jack hears this story and

00:17:21.910 --> 00:17:24.829
sees a routing error. He sees a routing error.

00:17:25.349 --> 00:17:27.529
The money wanted to move from point A to point

00:17:27.529 --> 00:17:30.390
B, but the gateway was closed. The system was

00:17:30.390 --> 00:17:32.990
broken. He looked at the state of payment processing

00:17:32.990 --> 00:17:35.089
for small businesses at the time. It was a nightmare.

00:17:35.470 --> 00:17:37.410
You needed a credit check. You had to pay hundreds

00:17:37.410 --> 00:17:40.710
in monthly fees. You had to buy or lease a bulky

00:17:40.710 --> 00:17:43.589
Verifone terminal that needed a dedicated landline.

00:17:43.710 --> 00:17:46.170
It was totally exclusionary. It was a gated,

00:17:46.170 --> 00:17:49.349
centralized system controlled by a few big banks

00:17:49.349 --> 00:17:52.109
and processors. And Jack's instinct is always

00:17:52.109 --> 00:17:54.890
to break the gate. So he and McKelvey set out

00:17:54.890 --> 00:17:57.069
to solve this. And the technology they came up

00:17:57.069 --> 00:17:59.750
with is just genuinely brilliant in its simplicity.

00:18:00.069 --> 00:18:02.230
The little white square reader. The square reader.

00:18:02.410 --> 00:18:04.910
They didn't try to build a complex new... piece

00:18:04.910 --> 00:18:07.890
of hardware. They had a key inside. They realized

00:18:07.890 --> 00:18:10.210
that the magnetic stripe on the back of a credit

00:18:10.210 --> 00:18:12.670
card is just encoded data. It's just information.

00:18:13.009 --> 00:18:15.549
And the headphone jack on a smartphone. It's

00:18:15.549 --> 00:18:18.029
an input device. It's an analog audio input.

00:18:18.170 --> 00:18:21.230
It's designed to listen. So they built a tiny,

00:18:21.250 --> 00:18:24.009
cheap magnetic read head. That's the little slot

00:18:24.009 --> 00:18:27.109
in the white square. Wired it directly to a standard

00:18:27.109 --> 00:18:30.250
headphone plug and then wrote software on the

00:18:30.250 --> 00:18:33.190
phone to decode the analog signal. So when you

00:18:33.190 --> 00:18:36.049
swipe the card. the phone literally hears the

00:18:36.049 --> 00:18:39.049
data as a screeching sound like an old dial -up

00:18:39.049 --> 00:18:42.400
modem exactly They turned the credit card into

00:18:42.400 --> 00:18:46.539
an MP3 file, essentially. And the software decodes

00:18:46.539 --> 00:18:48.720
that screeching sound into the account numbers.

00:18:48.920 --> 00:18:51.500
By doing that, they bypassed the need for hundreds

00:18:51.500 --> 00:18:53.559
of dollars of specialized hardware. They could

00:18:53.559 --> 00:18:55.619
manufacture the readers for pennies. Which meant

00:18:55.619 --> 00:18:57.460
they could give them away for free. And that

00:18:57.460 --> 00:18:59.579
changed everything. Suddenly, the person at the

00:18:59.579 --> 00:19:01.619
farmer's market, the coffee shop, the piano teacher,

00:19:01.839 --> 00:19:04.380
the babysitter, they were all instantly dispatched

00:19:04.380 --> 00:19:06.940
into the modern financial system. It's the exact

00:19:06.940 --> 00:19:09.839
same pattern as Twitter. Twitter allowed anyone

00:19:09.839 --> 00:19:12.940
to broadcast a message. Square allowed anyone

00:19:12.940 --> 00:19:15.980
to receive a payment. He empowers the nodes at

00:19:15.980 --> 00:19:17.960
the edge of the network. He routes around the

00:19:17.960 --> 00:19:21.500
central authority. And Square grew exponentially.

00:19:21.500 --> 00:19:23.920
It was a massive success. They went public in

00:19:23.920 --> 00:19:26.420
2015. But you have to notice the date there.

00:19:26.779 --> 00:19:29.859
2015 is a critical year in the Jack Dorsey story.

00:19:30.099 --> 00:19:32.019
Because that's the year Twitter came calling

00:19:32.019 --> 00:19:34.240
again. Twitter had been drifting under its CEO

00:19:34.240 --> 00:19:37.759
at the time, Dick Costolo. The stock was stagnant.

00:19:37.819 --> 00:19:40.059
User growth had stalled. The product hadn't really

00:19:40.059 --> 00:19:42.839
evolved. The board, perhaps realizing they'd

00:19:42.839 --> 00:19:45.400
made a huge mistake years earlier, went back

00:19:45.400 --> 00:19:47.559
to Jack, hat in hand, and asked him to come back

00:19:47.559 --> 00:19:51.299
as CEO. But he laid down a condition. He refused

00:19:51.299 --> 00:19:53.880
to quit Square. He demanded to be the CEO of

00:19:53.880 --> 00:19:56.140
two publicly traded companies at the same time,

00:19:56.180 --> 00:19:57.920
which, I mean, that's almost unheard of. Elon

00:19:57.920 --> 00:20:00.680
Musk does it now with the Tesla and SpaceX and

00:20:00.680 --> 00:20:03.339
X. But at that time, Wall Street viewed it as

00:20:03.339 --> 00:20:05.980
complete insanity. So how on earth did he manage

00:20:05.980 --> 00:20:08.660
it? Two massive companies. Through a rigorous,

00:20:08.839 --> 00:20:11.880
almost robotic scheduling system. He themed his

00:20:11.880 --> 00:20:14.119
days. He would literally work at the Twitter

00:20:14.119 --> 00:20:16.680
office in the morning, then walk across the street

00:20:16.680 --> 00:20:18.500
to the Squire office in the afternoon. Or the

00:20:18.500 --> 00:20:20.660
themes. Monday was for management meetings at

00:20:20.660 --> 00:20:22.980
both companies. Tuesday was for product meetings

00:20:22.980 --> 00:20:25.359
at both companies. Wednesday was marketing and

00:20:25.359 --> 00:20:27.900
so on. It was an incredible feat of executive

00:20:27.900 --> 00:20:30.619
time management and, frankly, mental processing

00:20:30.619 --> 00:20:33.420
power. But this second term at Twitter, from

00:20:33.420 --> 00:20:37.200
2015 to 2021. this is where things get really

00:20:37.200 --> 00:20:40.279
complicated this is where the technological monk

00:20:40.279 --> 00:20:42.640
starts to face the demons of his own creation

00:20:42.640 --> 00:20:45.240
he was walking back into a very different internet

00:20:45.720 --> 00:20:48.940
The internet of 2015 was not the fun, quirky

00:20:48.940 --> 00:20:51.839
internet of 2006. The culture wars had begun

00:20:51.839 --> 00:20:54.599
in earnest. Disinformation was being weaponized

00:20:54.599 --> 00:20:57.579
by state actors. And Twitter, under the previous

00:20:57.579 --> 00:20:59.579
leadership, had made a fundamental architectural

00:20:59.579 --> 00:21:02.240
change that Jack would later come to regret more

00:21:02.240 --> 00:21:04.400
than anything else. They introduced the algorithmic

00:21:04.400 --> 00:21:07.059
feed. Yes. Explain that shift for us because

00:21:07.059 --> 00:21:09.640
it's so fundamental to understanding the problems

00:21:09.640 --> 00:21:12.019
of social media today. Originally, your Twitter

00:21:12.019 --> 00:21:14.930
timeline was simple. Reverse chronological. You

00:21:14.930 --> 00:21:16.670
saw the newest tweet from the people you followed

00:21:16.670 --> 00:21:19.130
at the very top. It was a raw, unfiltered feed

00:21:19.130 --> 00:21:21.230
of information. Like a stock ticker. Exactly.

00:21:21.430 --> 00:21:24.549
But in the race for engagement, to keep your

00:21:24.549 --> 00:21:26.710
eyeballs glued to the app for longer so they

00:21:26.710 --> 00:21:29.250
could sell more ads, they switched to a relevance

00:21:29.250 --> 00:21:31.730
-based model. The algorithm would start guessing

00:21:31.730 --> 00:21:33.750
what you wanted to see based on your past behavior.

00:21:34.150 --> 00:21:36.369
It would surface the most popular or controversial

00:21:36.369 --> 00:21:38.930
tweets and put those at the top. This is the

00:21:38.930 --> 00:21:41.609
move that creates the echo chambers. The algorithm

00:21:41.609 --> 00:21:43.930
learns that I get really angry about a certain

00:21:43.930 --> 00:21:45.869
topic, so it just starts feeding me more and

00:21:45.869 --> 00:21:48.130
more outrage about that topic because outrage

00:21:48.130 --> 00:21:51.990
drives clicks and replies. Correct. It optimizes

00:21:51.990 --> 00:21:54.309
for emotional reaction. not for informational

00:21:54.309 --> 00:21:57.329
accuracy or diversity of thought. And years later,

00:21:57.430 --> 00:22:00.230
in 2022, after he had left, Dorsey wrote this

00:22:00.230 --> 00:22:03.049
incredible postmortem on it all. He said, and

00:22:03.049 --> 00:22:05.549
I'm quoting here, the biggest mistake I made

00:22:05.549 --> 00:22:07.970
was continuing to invest in building tools for

00:22:07.970 --> 00:22:10.690
us to manage the public conversation versus building

00:22:10.690 --> 00:22:12.890
tools for the people using Twitter to easily

00:22:12.890 --> 00:22:15.940
manage it for themselves. Wow. That's a profound

00:22:15.940 --> 00:22:19.079
admission of guilt, almost. He's saying we, the

00:22:19.079 --> 00:22:21.380
company, took the power away from you, the user,

00:22:21.519 --> 00:22:23.680
and gave it to our own engineers and our own

00:22:23.680 --> 00:22:27.470
algorithms. That centralization of power, that

00:22:27.470 --> 00:22:30.650
decision to manage the conversation collided

00:22:30.650 --> 00:22:32.829
head on with the political phenomenon of Donald

00:22:32.829 --> 00:22:35.650
Trump. The Trump presidency. This was the ultimate

00:22:35.650 --> 00:22:38.109
stress test for Twitter's entire philosophy.

00:22:38.329 --> 00:22:40.809
It was. You had a sitting U .S. president using

00:22:40.809 --> 00:22:43.089
the platform as his primary communication tool,

00:22:43.250 --> 00:22:46.390
bypassing the entire traditional media establishment.

00:22:46.650 --> 00:22:49.049
And in doing so, he was frequently posting things

00:22:49.049 --> 00:22:52.049
that for any other user would have been clear

00:22:52.049 --> 00:22:54.369
violations of Twitter's own terms of service.

00:22:57.029 --> 00:23:00.069
So Jack had a meeting with Trump in 2019 at the

00:23:00.069 --> 00:23:02.730
White House. He did. And the readout from that

00:23:02.730 --> 00:23:04.789
meeting is just fascinating. Apparently, Trump

00:23:04.789 --> 00:23:06.950
spent a significant portion of the time complaining

00:23:06.950 --> 00:23:09.430
that his follower count was dropping. He was

00:23:09.430 --> 00:23:11.910
convinced that Jack was personally shadow banning

00:23:11.910 --> 00:23:14.049
him to hurt him politically. And what was Jack's

00:23:14.049 --> 00:23:16.789
response? Jack calmly explained that the company

00:23:16.789 --> 00:23:19.819
was just. purging millions of bot and spam accounts

00:23:19.819 --> 00:23:22.299
from the platform, and that all major accounts,

00:23:22.420 --> 00:23:24.680
including his, were losing some followers as

00:23:24.680 --> 00:23:27.640
a result. But for years, Dorsey defended the

00:23:27.640 --> 00:23:30.019
decision to keep Trump on the platform, even

00:23:30.019 --> 00:23:32.700
when the pressure was immense. He created something

00:23:32.700 --> 00:23:35.539
called the World Leader Exception. What was the

00:23:35.539 --> 00:23:38.319
argument there? The argument was that the public

00:23:38.319 --> 00:23:40.519
has a right to know what their leaders are saying,

00:23:40.700 --> 00:23:43.119
even if it's controversial or factually incorrect.

00:23:43.640 --> 00:23:46.259
That it's more dangerous to deplatform a world

00:23:46.259 --> 00:23:48.430
leader and drive their speech into the shadows

00:23:48.430 --> 00:23:50.569
than it is to let it exist in the open where

00:23:50.569 --> 00:23:53.009
it can be debated and fact checked. That was

00:23:53.009 --> 00:23:57.430
the policy until January 6th, 2021. After the

00:23:57.430 --> 00:23:59.990
attack on the U .S. Capitol, the internal calculus

00:23:59.990 --> 00:24:02.910
at Twitter changed. The risk of imminent real

00:24:02.910 --> 00:24:05.630
world violence was deemed to outweigh the newsworthiness

00:24:05.630 --> 00:24:08.230
of the tweets. They made the decision to permanently

00:24:08.230 --> 00:24:10.789
suspend Donald Trump's account. And Jack, as

00:24:10.789 --> 00:24:13.089
CEO, signed off on it. But he didn't celebrate

00:24:13.089 --> 00:24:14.730
it, which I think a lot of people expected him

00:24:14.730 --> 00:24:17.069
to. No, not at all. And this is where people

00:24:17.069 --> 00:24:19.230
on both sides of the aisle completely misread

00:24:19.230 --> 00:24:21.829
him. Liberals were cheering, thinking he'd finally

00:24:21.829 --> 00:24:24.369
seen the light. Conservatives were furious, screaming

00:24:24.369 --> 00:24:27.549
about censorship. And Jack was, well, he seemed

00:24:27.549 --> 00:24:30.109
mournful about it. Mournful. He posted this long

00:24:30.109 --> 00:24:32.349
thread a few days later saying that while he

00:24:32.349 --> 00:24:34.349
believed it was the right decision for public

00:24:34.349 --> 00:24:36.730
safety at that moment, it was also a failure.

00:24:36.890 --> 00:24:40.089
A failure of their platform to promote healthy

00:24:40.089 --> 00:24:43.650
conversation. And he called it a dangerous precedent.

00:24:44.299 --> 00:24:46.920
He realized that if one CEO in San Francisco

00:24:46.920 --> 00:24:49.220
can unilaterally silence the president of the

00:24:49.220 --> 00:24:52.180
United States, then that CEO simply has too much

00:24:52.180 --> 00:24:54.400
power. And if there's one thing we've established,

00:24:54.619 --> 00:24:57.299
it's that Jack Dorsey fundamentally distrusts

00:24:57.299 --> 00:24:59.980
centralized power, even when it's his own. So

00:24:59.980 --> 00:25:02.180
he's had this realization. He's seen the monster

00:25:02.180 --> 00:25:04.599
that his creation has become. What happens next?

00:25:04.819 --> 00:25:08.000
In November 2021, he resigns. He posts his resignation

00:25:08.000 --> 00:25:10.619
email on Twitter. He says the company is ready

00:25:10.619 --> 00:25:12.980
to move on from its founders. He hands the reins

00:25:12.980 --> 00:25:15.759
over to the CTO, Parag Agarwal, and just walks

00:25:15.759 --> 00:25:18.900
away. But he doesn't retire to an island. He

00:25:18.900 --> 00:25:22.839
immediately rebrands Scared of Lock, Inc., and

00:25:22.839 --> 00:25:26.799
pivots hard into what you call part four of his

00:25:26.799 --> 00:25:30.109
story, the decentralization maximalist. This

00:25:30.109 --> 00:25:32.009
is the part that just completely confuses the

00:25:32.009 --> 00:25:34.250
mainstream business press. He stops talking about

00:25:34.250 --> 00:25:36.410
quarterly earnings and ad revenue and starts

00:25:36.410 --> 00:25:39.069
talking about cryptographic protocols. He goes

00:25:39.069 --> 00:25:41.789
from being a tech CEO to being essentially a

00:25:41.789 --> 00:25:45.210
Bitcoin evangelist. To Jack, Bitcoin isn't just

00:25:45.210 --> 00:25:47.470
a speculative asset to trade. It's something

00:25:47.470 --> 00:25:49.829
much more profound. He calls it freedom money.

00:25:49.970 --> 00:25:52.210
He does. And we have to understand the connection

00:25:52.210 --> 00:25:55.289
in his mind. So why? What's the link between

00:25:55.289 --> 00:25:58.089
a dispatch system for taxes and a decentralized

00:25:58.089 --> 00:26:01.250
digital currency? Go back to the map. In a centralized

00:26:01.250 --> 00:26:03.529
banking system, the one we all use, the bank

00:26:03.529 --> 00:26:05.450
is the dispatcher. They sit in the middle. They

00:26:05.450 --> 00:26:07.470
decide if your transaction is valid. They can

00:26:07.470 --> 00:26:09.509
freeze your account. They can reverse a transaction.

00:26:09.670 --> 00:26:12.549
They have control. In Bitcoin, there is no central

00:26:12.549 --> 00:26:15.170
dispatcher. The network itself is the dispatcher.

00:26:15.190 --> 00:26:17.509
It relies on a mathematical concept called proof

00:26:17.509 --> 00:26:20.109
of work. Can you break that down for us in simple

00:26:20.109 --> 00:26:22.390
terms? Proof of work just means that in order

00:26:22.390 --> 00:26:25.109
to validate a block of transactions and add it

00:26:25.109 --> 00:26:29.509
to the blockchain, a computer, a miner, has to

00:26:29.509 --> 00:26:32.869
expend real world energy. It has to solve a very

00:26:32.869 --> 00:26:35.789
difficult but verifiable mathematical puzzle.

00:26:36.130 --> 00:26:39.049
No single person or company controls this process.

00:26:39.410 --> 00:26:42.329
It's a consensus mechanism run by thousands of

00:26:42.329 --> 00:26:44.630
independent computers all over the world. And

00:26:44.630 --> 00:26:47.750
Jack loves it because it's permissionless. That's

00:26:47.750 --> 00:26:50.410
the key word. You don't need a passport or a

00:26:50.410 --> 00:26:53.170
credit score or a bank's permission to use Bitcoin.

00:26:53.450 --> 00:26:56.250
All you need is a private key. He sees it as

00:26:56.250 --> 00:26:58.960
the native currency of an open Internet. Now,

00:26:58.960 --> 00:27:01.099
we have to touch on the Internet conspiracy theories

00:27:01.099 --> 00:27:03.819
here. There are persistent rumors that Jack himself

00:27:03.819 --> 00:27:06.380
is Satoshi Nakamoto, the anonymous creator of

00:27:06.380 --> 00:27:08.460
Bitcoin. It's a very fun theory to entertain.

00:27:08.599 --> 00:27:10.859
I mean, he has the deep cryptographic background.

00:27:10.960 --> 00:27:13.200
You have to remember the early dispatch services

00:27:13.200 --> 00:27:15.599
he built were all about secure encrypted communication.

00:27:16.079 --> 00:27:18.980
He certainly has the cypherpunk philosophy of

00:27:18.980 --> 00:27:21.799
privacy and decentralization. And he was in the

00:27:21.799 --> 00:27:23.579
right place at the right time. So do you think

00:27:23.579 --> 00:27:26.259
it's true? I would say it's highly, highly unlikely.

00:27:26.640 --> 00:27:29.460
During the critical period when Satoshi was actively

00:27:29.460 --> 00:27:32.680
coding and writing about Bitcoin, from 2008 to

00:27:32.680 --> 00:27:35.220
2010, Jack was in the middle of getting fired

00:27:35.220 --> 00:27:37.400
from Twitter and launching Square. He was a little

00:27:37.400 --> 00:27:40.500
busy. But spiritually, I think he sees himself

00:27:40.500 --> 00:27:43.339
as Satoshi's most important disciple. He's on

00:27:43.339 --> 00:27:45.720
record saying he believes Bitcoin is one of the

00:27:45.720 --> 00:27:47.539
most important developments for the future of

00:27:47.539 --> 00:27:50.440
world peace. World peace. That's a... That is

00:27:50.440 --> 00:27:53.559
a very big claim for a digital currency. It sounds

00:27:53.559 --> 00:27:55.779
hyperbolic, but his argument has a certain logic

00:27:55.779 --> 00:27:58.680
to it. His argument is that most major wars are

00:27:58.680 --> 00:28:00.819
funded by governments endlessly printing money,

00:28:01.039 --> 00:28:03.799
devaluing their currency to pay for armies and

00:28:03.799 --> 00:28:06.579
weapons. If a government had to operate on a

00:28:06.579 --> 00:28:08.980
sound money standard like Bitcoin that they couldn't

00:28:08.980 --> 00:28:11.380
inflate, it would be much harder to fund perpetual

00:28:11.380 --> 00:28:13.980
conflict. It's an anti -war technology in his

00:28:13.980 --> 00:28:16.259
view. And he's putting his company's money and

00:28:16.259 --> 00:28:18.759
his own money where his mouth is. He funded a

00:28:18.759 --> 00:28:22.039
project called Ocean. Right. Ocean is a Bitcoin

00:28:22.039 --> 00:28:24.700
mining pool. See, one of the problems Bitcoin

00:28:24.700 --> 00:28:27.200
has right now is that the mining process itself

00:28:27.200 --> 00:28:30.660
is becoming more centralized. A few huge publicly

00:28:30.660 --> 00:28:33.099
traded companies control a massive percentage

00:28:33.099 --> 00:28:35.880
of the global hash rate. Which creates a new

00:28:35.880 --> 00:28:39.059
central point of failure. It does. If those few

00:28:39.059 --> 00:28:41.720
companies were ever to collude or be forced by

00:28:41.720 --> 00:28:44.059
a government to do so, they could theoretically

00:28:44.059 --> 00:28:47.359
censor certain transactions. Ocean is what's

00:28:47.359 --> 00:28:50.200
known as a non -custodial mining pool. It allows

00:28:50.200 --> 00:28:53.160
small individual miners to pool their resources

00:28:53.160 --> 00:28:56.000
and earn rewards without ever giving up control

00:28:56.000 --> 00:28:58.700
of their hardware to a central operator. It's

00:28:58.700 --> 00:29:01.339
about decentralizing the decentralization. And

00:29:01.339 --> 00:29:03.180
there's the other side of it. He gave up on Twitter

00:29:03.180 --> 00:29:05.180
as a company, but he clearly didn't give up on

00:29:05.180 --> 00:29:07.140
the idea of social networking. He just. thinks

00:29:07.140 --> 00:29:09.019
it shouldn't be a company. This brings us to

00:29:09.019 --> 00:29:11.940
the whole Blueski versus Nostra saga. It's really

00:29:11.940 --> 00:29:14.599
revealing. Right. Blueski was his own project,

00:29:14.740 --> 00:29:17.619
started inside Twitter. He started Blueski at

00:29:17.619 --> 00:29:20.160
Twitter in 2019 with the goal of building an

00:29:20.160 --> 00:29:23.980
open, decentralized social media protocol. The

00:29:23.980 --> 00:29:26.440
long -term vision was that Twitter itself would

00:29:26.440 --> 00:29:28.759
eventually just become one of many clients that

00:29:28.759 --> 00:29:31.299
could plug into this open standard. But after

00:29:31.299 --> 00:29:33.880
he left Twitter, Blueski spun off into its own

00:29:33.880 --> 00:29:36.319
independent company. It did. It took on venture

00:29:36.319 --> 00:29:38.759
capital funding. It formed a public benefit corporation.

00:29:39.319 --> 00:29:42.500
It appointed a board, which Jack sat on. And

00:29:42.500 --> 00:29:44.319
it started doing all the things companies do.

00:29:44.460 --> 00:29:46.880
It started building centralized moderation tools.

00:29:47.039 --> 00:29:49.960
It started acting like... Twitter. And Jack hated

00:29:49.960 --> 00:29:53.140
it. He grew disillusioned. In May of 2024, he

00:29:53.140 --> 00:29:56.220
very publicly left the blue ski board. He deleted

00:29:56.220 --> 00:29:58.200
his account and said they were repeating all

00:29:58.200 --> 00:30:00.519
the mistakes we made at Twitter. He doesn't want

00:30:00.519 --> 00:30:02.859
a better, more decentralized Twitter. He wants

00:30:02.859 --> 00:30:05.579
no Twitter. He wants a protocol, not a platform.

00:30:05.720 --> 00:30:08.759
So he pivoted all his support and energy to Noster.

00:30:09.259 --> 00:30:11.799
Noster, which stands for notes and other stuff

00:30:11.799 --> 00:30:14.099
transmitted by relays. It's a terrible name.

00:30:14.220 --> 00:30:16.079
It's a terrible name, but the concept is what

00:30:16.079 --> 00:30:18.299
matters to him. So what makes it fundamentally

00:30:18.299 --> 00:30:21.119
different from BlueSky or Twitter? Noster isn't

00:30:21.119 --> 00:30:23.940
a platform. It's a protocol, just like email

00:30:23.940 --> 00:30:27.759
or HTTP are protocols. No single person or company

00:30:27.759 --> 00:30:30.579
owns email, right? You can use Gmail. I can use

00:30:30.579 --> 00:30:32.900
Outlook. A company can run its own server and

00:30:32.900 --> 00:30:36.119
we can all still talk to each other. Right. Nostra

00:30:36.119 --> 00:30:38.420
is the same for social media. There is no central

00:30:38.420 --> 00:30:40.940
Nostra server. There's no Nostra Inc. So where

00:30:40.940 --> 00:30:43.319
does the data actually live? It lives on a network

00:30:43.319 --> 00:30:46.619
of independent relays. Anyone can run a relay.

00:30:46.720 --> 00:30:48.440
You can run one on a cheap computer in your basement.

00:30:48.660 --> 00:30:50.599
When I want to post a message, I sign it with

00:30:50.599 --> 00:30:53.900
my private cryptographic key. That's my uncensorable

00:30:53.900 --> 00:30:56.519
identity. And I send it out to a handful of relays

00:30:56.519 --> 00:30:58.980
that I like. Your app, your client, just connects

00:30:58.980 --> 00:31:01.140
to those same relays and pulls my message down.

00:31:01.359 --> 00:31:04.000
So if a relay owner decides, I don't like what

00:31:04.000 --> 00:31:06.299
this person is saying, and they ban you from

00:31:06.299 --> 00:31:09.440
their relay, what happens? Nothing, really. I

00:31:09.440 --> 00:31:11.319
just start sending my messages to different relays.

00:31:11.400 --> 00:31:13.920
My identity isn't tied to any one server. It's

00:31:13.920 --> 00:31:16.140
tied to my cryptographic key. It is designed

00:31:16.140 --> 00:31:18.920
from the ground up to be censorship resistant.

00:31:19.319 --> 00:31:21.819
And he's even thinking beyond the internet now.

00:31:21.960 --> 00:31:24.099
He's been talking about Bluetooth mesh networks.

00:31:24.539 --> 00:31:27.029
This is the most radical step. This is for a

00:31:27.029 --> 00:31:29.230
situation where the internet itself goes down.

00:31:29.809 --> 00:31:32.470
Imagine a large protest where a government decides

00:31:32.470 --> 00:31:35.210
to shut down all the cell towers and cut off

00:31:35.210 --> 00:31:38.170
Internet access. Bluetooth mesh allows phones

00:31:38.170 --> 00:31:40.170
to talk directly to each other, peer to peer.

00:31:40.349 --> 00:31:42.750
Like a daisy chain of data. A digital bucket

00:31:42.750 --> 00:31:45.490
brigade. My phone talks to your phone, which

00:31:45.490 --> 00:31:47.690
talks to the phone next to you. It creates a

00:31:47.690 --> 00:31:50.490
local ad hoc network with no central infrastructure

00:31:50.490 --> 00:31:54.309
at all. He funded an app in 2025 called BitChat

00:31:54.309 --> 00:31:57.230
that uses this technology. It is dispatching

00:31:57.230 --> 00:32:00.140
without a dispatcher. ultimate realization of

00:32:00.140 --> 00:32:02.440
that teenage dream of watching dots move on a

00:32:02.440 --> 00:32:05.359
map. But now with no central tower controlling

00:32:05.359 --> 00:32:07.440
them, it's incredible how consistent the core

00:32:07.440 --> 00:32:10.099
philosophy is from a scanner in St. Louis all

00:32:10.099 --> 00:32:12.220
the way to blockchain protocols. But we have

00:32:12.220 --> 00:32:14.519
to look at the man himself, part five, because

00:32:14.519 --> 00:32:17.289
the way he lives his life is. Just as intense

00:32:17.289 --> 00:32:19.890
and just as extreme as the software he funds.

00:32:20.089 --> 00:32:21.789
Yeah, we have to talk about the technological

00:32:21.789 --> 00:32:24.910
monk persona because it's not just an act. He

00:32:24.910 --> 00:32:27.210
lives in Seacliff, a beautiful neighborhood in

00:32:27.210 --> 00:32:30.529
San Francisco, has a $10 million compound overlooking

00:32:30.529 --> 00:32:32.849
the Golden Gate Bridge. But by all accounts,

00:32:33.029 --> 00:32:35.670
inside that house, he lives like an ascetic.

00:32:35.829 --> 00:32:38.109
The meditation is a huge part of it. A huge part.

00:32:38.190 --> 00:32:40.710
He practices Vipassana meditation. And we need

00:32:40.710 --> 00:32:42.869
to be clear, this isn't the kind of mindfulness

00:32:42.869 --> 00:32:45.650
you do on a five -minute app. This is an ancient,

00:32:45.809 --> 00:32:49.509
rigorous, demanding tradition. In late 2017,

00:32:49.809 --> 00:32:52.730
he did a 10 -day silent retreat. Walk us through

00:32:52.730 --> 00:32:54.569
what that actually entails. It's intense. You

00:32:54.569 --> 00:32:57.319
wake up at 4 a .m. You meditate something like

00:32:57.319 --> 00:32:59.539
10 hours a day. You're not allowed to eat after

00:32:59.539 --> 00:33:01.640
midday. No reading, no writing, no phones, no

00:33:01.640 --> 00:33:03.480
music. You don't even make eye contact with the

00:33:03.480 --> 00:33:05.859
other people there. You are completely and totally

00:33:05.859 --> 00:33:08.319
alone with your own mind for 10 straight days.

00:33:08.579 --> 00:33:11.420
For a guy whose brain seems to be wired for constant

00:33:11.420 --> 00:33:15.539
high speed data inputs, that must have been excruciatingly

00:33:15.539 --> 00:33:17.740
difficult. He said it was one of the most painful

00:33:17.740 --> 00:33:20.500
and difficult things he's ever done. But he believes

00:33:20.500 --> 00:33:23.720
it's necessary to, in his words, hack his own

00:33:23.720 --> 00:33:27.130
brain to debug. his own mental source code and

00:33:27.130 --> 00:33:29.710
see the world as it really is. But that intense

00:33:29.710 --> 00:33:32.849
inward focus can have a huge blind spot. It can

00:33:32.849 --> 00:33:35.710
backfire. We have to address the Myanmar trip.

00:33:35.890 --> 00:33:38.710
We do. In 2018, for his birthday, he went to

00:33:38.710 --> 00:33:40.529
Myanmar to do another one of these meditation

00:33:40.529 --> 00:33:43.589
retreats. And when he came out, he tweeted about

00:33:43.589 --> 00:33:46.430
how beautiful the country was, how peaceable

00:33:46.430 --> 00:33:48.890
and kind the people were. And he posted this

00:33:48.890 --> 00:33:51.009
at the exact same time that the Myanmar military

00:33:51.009 --> 00:33:54.049
was in the middle of conducting a brutal genocide

00:33:54.049 --> 00:33:56.490
against the Rohingya Muslim minority. It was

00:33:56.490 --> 00:33:59.569
a massive, unforced PR disaster. Critics, I think,

00:33:59.569 --> 00:34:01.289
rightfully pointed out that his own platform,

00:34:01.549 --> 00:34:03.650
Twitter, had been used as a tool to spread hate

00:34:03.650 --> 00:34:06.089
speech and incite violence against the Rohingya.

00:34:06.170 --> 00:34:08.750
And here he was, the CEO, essentially promoting

00:34:08.750 --> 00:34:11.050
tourism to the country without even acknowledging

00:34:11.050 --> 00:34:13.090
the atrocities that were happening. It suggests

00:34:13.090 --> 00:34:15.920
a kind of profound tunnel vision. He was so focused

00:34:15.920 --> 00:34:18.280
on achieving his own internal silence that he

00:34:18.280 --> 00:34:20.400
completely tuned out the screams of external

00:34:20.400 --> 00:34:23.480
suffering. That is the dark side, the shadow

00:34:23.480 --> 00:34:27.079
side of that monk archetype. An extreme level

00:34:27.079 --> 00:34:30.320
of detachment can start to look a lot like indifference.

00:34:30.579 --> 00:34:33.079
Let's pivot to his politics, though. Yeah. Because

00:34:33.079 --> 00:34:35.239
you absolutely cannot put him in a simple box.

00:34:35.440 --> 00:34:37.840
Oh, he's a complete nightmare for political pundits

00:34:37.840 --> 00:34:40.900
who want to label everyone. In the 2020 Democratic

00:34:40.900 --> 00:34:44.119
primary, he donated to two candidates. Tulsi

00:34:44.119 --> 00:34:48.190
Gabbard and Andrew Yang. But both definite outsiders.

00:34:48.650 --> 00:34:50.550
Yang, of course, was a universal basic income

00:34:50.550 --> 00:34:53.309
candidate. And UBI is a huge passion for Jack.

00:34:53.449 --> 00:34:56.730
Right. But then fast forward to 2024 and he very

00:34:56.730 --> 00:34:59.409
publicly endorses Robert F. Kennedy Jr. for president.

00:34:59.610 --> 00:35:02.429
Who is the ultimate anti -establishment chaos

00:35:02.429 --> 00:35:05.510
agent. RFK Jr.'s entire platform is built on

00:35:05.510 --> 00:35:07.190
challenging the pharmaceutical industry, the

00:35:07.190 --> 00:35:09.590
intelligence agencies, the mainstream media,

00:35:09.789 --> 00:35:11.869
basically questioning every official narrative.

00:35:12.070 --> 00:35:15.230
And Jack loves that questioning spirit. But here's

00:35:15.230 --> 00:35:17.929
the twist. At the same time he's supporting RFK

00:35:17.929 --> 00:35:21.230
Jr., he donates $10 million to Boston University's

00:35:21.230 --> 00:35:23.710
Center for Anti -Racist Research, founded by

00:35:23.710 --> 00:35:26.170
Dr. Ibram X. Kendi. The leading academic scholar

00:35:26.170 --> 00:35:27.750
of what's often called critical race theory.

00:35:28.090 --> 00:35:30.489
Exactly. So on one hand, you have RFK Jr., and

00:35:30.489 --> 00:35:32.940
on the other, you have Ibram X. Kendi. Most people

00:35:32.940 --> 00:35:34.940
would look at that and see a complete contradiction,

00:35:35.219 --> 00:35:37.900
a political schizophrenic. But I think in Jack's

00:35:37.900 --> 00:35:40.340
mind, it's perfectly consistent. How do you square

00:35:40.340 --> 00:35:42.579
that circle? They are both in their own ways

00:35:42.579 --> 00:35:45.239
challenging the system. Kendi is challenging

00:35:45.239 --> 00:35:47.679
the systemic power structures of race in America.

00:35:48.119 --> 00:35:50.559
RFK is challenging the systemic power structures

00:35:50.559 --> 00:35:53.500
of government and corporations. Jack is fundamentally

00:35:53.500 --> 00:35:56.500
anti -centralization. He will support anyone

00:35:56.500 --> 00:35:59.139
he sees as trying to break up the big monolithic

00:35:59.139 --> 00:36:01.960
blobs of power. He's also tweeted in. support

00:36:01.960 --> 00:36:04.559
of the Gaza war protests and even drew parallels

00:36:04.559 --> 00:36:07.340
to the Vietnam and Iraq war protests. He's very

00:36:07.340 --> 00:36:10.360
consistently anti -war. Because war is the ultimate,

00:36:10.440 --> 00:36:13.679
most violent expression of the centralized state.

00:36:13.840 --> 00:36:16.519
He's a libertarian in the truest nonpartisan

00:36:16.519 --> 00:36:19.280
sense of that word. He trusts individuals over

00:36:19.280 --> 00:36:21.599
institutes every single time. And that trust

00:36:21.599 --> 00:36:23.820
in individuals is the driving force behind his

00:36:23.820 --> 00:36:26.000
philanthropy, right? The start small initiative.

00:36:26.300 --> 00:36:28.219
This is one of the most interesting things he's

00:36:28.219 --> 00:36:31.809
done. It's April 2020. The COVID -19 pandemic

00:36:31.809 --> 00:36:35.050
is just starting to explode globally. Jack takes

00:36:35.050 --> 00:36:38.170
$1 billion of his equity in Square, which at

00:36:38.170 --> 00:36:40.610
the time was about 28 % of his total net worth,

00:36:40.750 --> 00:36:43.429
and he moves it into a new entity. But it wasn't

00:36:43.429 --> 00:36:46.190
a typical foundation. No. He didn't create a

00:36:46.190 --> 00:36:49.050
501C foundation, which comes with a board of

00:36:49.050 --> 00:36:52.170
directors, huge overhead costs and a slow bureaucratic

00:36:52.170 --> 00:36:55.969
process. He moved it into a simple LLC, a limited

00:36:55.969 --> 00:36:57.989
liability company. What's the practical difference

00:36:57.989 --> 00:37:00.969
there? An LLC is just a company. He is the sole

00:37:00.969 --> 00:37:03.429
member. He can write a check to anyone for any

00:37:03.429 --> 00:37:06.329
reason in five minutes. It's agile. And he did

00:37:06.329 --> 00:37:09.030
something truly radical for transparency. The

00:37:09.030 --> 00:37:11.130
Google sheet. The Google sheet. He tweeted out

00:37:11.130 --> 00:37:13.030
a public link to a Google spreadsheet. It's called

00:37:13.030 --> 00:37:14.789
the Start Small Tracker. You can go look at it

00:37:14.789 --> 00:37:17.070
right now. It is a line -by -line public ledger

00:37:17.070 --> 00:37:20.030
of every single donation he has made from that

00:37:20.030 --> 00:37:22.510
billion dollars. So you can see it all. $10 million

00:37:22.510 --> 00:37:25.010
to the Reform Alliance for criminal justice reform.

00:37:25.610 --> 00:37:29.389
$20 million to CORE for COVID relief. $15 million

00:37:29.389 --> 00:37:32.190
for oxygen concentrators for India. It's all

00:37:32.190 --> 00:37:35.079
just there. Why a Google sheet? Because it's

00:37:35.079 --> 00:37:37.239
the dispatch aesthetic again. It's raw data.

00:37:37.440 --> 00:37:40.159
It's not a glossy annual report or a press release.

00:37:40.360 --> 00:37:43.380
It's just a ledger. He wants you to see the real

00:37:43.380 --> 00:37:46.679
-time flow of the money unvarnished. And a huge

00:37:46.679 --> 00:37:48.699
amount of that money, as you mentioned with Andrew

00:37:48.699 --> 00:37:51.019
Yang, goes to universal basic income experiments.

00:37:51.099 --> 00:37:53.829
A huge amount. He's the primary funder for a

00:37:53.829 --> 00:37:55.829
group called Mayors for a Guaranteed Income.

00:37:56.190 --> 00:37:58.590
He believes that the most efficient and dignified

00:37:58.590 --> 00:38:01.269
way to help people isn't to create a complex,

00:38:01.530 --> 00:38:04.230
top -down welfare bureaucracy. That's just another

00:38:04.230 --> 00:38:06.269
centralized dispatcher. He wants to just give

00:38:06.269 --> 00:38:07.969
people the money. Just give them the cash, a

00:38:07.969 --> 00:38:10.670
direct peer -to -peer transfer, and trust them

00:38:10.670 --> 00:38:12.429
to solve their own problems in their own way.

00:38:12.570 --> 00:38:14.650
He trusts the nodes at the edge of the network

00:38:14.650 --> 00:38:17.110
more than he trusts the hub in the center. So

00:38:17.110 --> 00:38:19.519
if we pull the lens back. We have this incredible

00:38:19.519 --> 00:38:22.139
picture of a man who spent the first half of

00:38:22.139 --> 00:38:24.599
his career building these massive centralized

00:38:24.599 --> 00:38:28.059
systems to route information and money and is

00:38:28.059 --> 00:38:30.880
now spending the entire second half of his career

00:38:30.880 --> 00:38:33.179
trying to build the tools that will make his

00:38:33.179 --> 00:38:36.159
own original creations obsolete. He wants to

00:38:36.159 --> 00:38:38.780
abdicate the throne he built. He wants to be

00:38:38.780 --> 00:38:41.840
the technological monk who writes the code, sets

00:38:41.840 --> 00:38:44.199
it free in the world, and then disappears back

00:38:44.199 --> 00:38:46.440
into the meditation hall. But we have to end

00:38:46.440 --> 00:38:48.570
with a harder question. Is he right? That is

00:38:48.570 --> 00:38:51.110
the multi -trillion dollar gamble of the 21st

00:38:51.110 --> 00:38:53.230
century. Because we have seen what happens on

00:38:53.230 --> 00:38:55.670
largely unmoderated decentralized platforms.

00:38:55.929 --> 00:38:58.809
You get floods of hate speech. You get coordinated

00:38:58.809 --> 00:39:01.510
harassment campaigns. You get state -sponsored

00:39:01.510 --> 00:39:04.670
bot armies. You get chaos. If you remove the

00:39:04.670 --> 00:39:06.849
dispatcher, if you fire all the trust and safety

00:39:06.849 --> 00:39:10.190
teams, does society actually function? Or does

00:39:10.190 --> 00:39:12.539
it just crash and burn? Jack's argument would

00:39:12.539 --> 00:39:14.679
be that the crash isn't caused by freedom. It's

00:39:14.679 --> 00:39:17.400
caused by the centralized engagement based algorithms

00:39:17.400 --> 00:39:19.940
that are manipulating us and amplifying the worst

00:39:19.940 --> 00:39:22.880
aspects of human nature for profit. He truly

00:39:22.880 --> 00:39:24.840
believes that if you give people tools that they

00:39:24.840 --> 00:39:27.079
own and control where they can choose their own

00:39:27.079 --> 00:39:30.360
algorithm or have no algorithm at all, that rationality

00:39:30.360 --> 00:39:32.619
and good faith will eventually return. He has

00:39:32.619 --> 00:39:34.960
a deep, almost religious faith in the wisdom

00:39:34.960 --> 00:39:37.480
of the crowd in its purest, most unfiltered form.

00:39:37.619 --> 00:39:40.190
He trusts the nodes. Full stop. It's a beautiful

00:39:40.190 --> 00:39:42.730
vision. Maybe it's a naive vision. Maybe it's

00:39:42.730 --> 00:39:45.429
the only way forward. But when you look at the

00:39:45.429 --> 00:39:48.710
world we live in right now, a world of AI -generated

00:39:48.710 --> 00:39:51.869
deepfakes, of pervasive information warfare,

00:39:52.960 --> 00:39:55.159
The idea of taking all the guardrails off seems

00:39:55.159 --> 00:39:58.519
terrifyingly risky. It is incredibly risky. But

00:39:58.519 --> 00:40:00.659
Jack looks at the alternative, a world where

00:40:00.659 --> 00:40:03.619
a Mark Zuckerberg or an Elon Musk or a government

00:40:03.619 --> 00:40:06.900
bureaucrat gets to be the final arbiter of what

00:40:06.900 --> 00:40:09.599
is true. And he thinks that is the far greater

00:40:09.599 --> 00:40:11.739
danger. So he's essentially handing out the matches

00:40:11.739 --> 00:40:14.400
and hoping we collectively decide not to burn

00:40:14.400 --> 00:40:16.760
the house down. Or he's hoping we realize we

00:40:16.760 --> 00:40:18.920
can use the fire to cook dinner and warm ourselves.

00:40:19.239 --> 00:40:21.579
It's a story that's still being written. And

00:40:21.579 --> 00:40:24.179
whether he is Satoshi or not, he is certainly

00:40:24.179 --> 00:40:26.500
the most Satoshi -like public figure we have.

00:40:26.659 --> 00:40:29.780
He embodies that spirit. He is the ultimate anti

00:40:29.780 --> 00:40:32.219
-CEO. We covered a ton of ground today. Mass

00:40:32.219 --> 00:40:34.860
spectrometers in St. Louis, silent retreats in

00:40:34.860 --> 00:40:36.920
Myanmar, the architecture of the blockchain.

00:40:37.239 --> 00:40:39.219
We didn't even get to really deep dive on his

00:40:39.219 --> 00:40:41.340
acquisition of the Music Streaming Service title,

00:40:41.400 --> 00:40:43.300
but that's a whole other story about empowering

00:40:43.300 --> 00:40:46.210
artists. Maybe for another day. I think the final

00:40:46.210 --> 00:40:48.530
thought, the thing for you, the listener, to

00:40:48.530 --> 00:40:51.010
take away from this is to just look at the digital

00:40:51.010 --> 00:40:53.570
tools you use every single day. Look at your

00:40:53.570 --> 00:40:55.869
social media feed, your bank account, your messaging

00:40:55.869 --> 00:41:00.170
apps, and ask yourself, who owns the map? Who

00:41:00.170 --> 00:41:02.829
is the dispatcher? And is it time you started

00:41:02.829 --> 00:41:05.030
dispatching yourself? That's the question he

00:41:05.030 --> 00:41:06.849
wants everyone to ask. Thanks for listening to

00:41:06.849 --> 00:41:08.230
The Deep Dive. We'll see you next time.
