Welcome back to the Deep Dive. Today we are opening
up a file on a figure who I think is just genuinely
misunderstood. I completely agree. And I don't
mean that in some kind of, you know, oh poor
billionaire way. I mean that the public image
of him, the perception, is so often diametrically
opposed to what the data actually shows. We are
talking about Jack Dorsey. It is such a fascinating
case study. I mean, usually when we profile the
giants of Silicon Valley, you know, the founders
who hit that multibillion dollar tier, we see
a very specific psychological profile. Right.
We see the empire builder, the relentless drive
to centralize, to acquire, to build the biggest,
baddest walled garden possible. You look at a
Zuckerberg, you look at Gates back in the 90s.
It's all about consolidation of power. Exactly.
The narrative is always I built the castle and
I own. the keys but dorsey is he's weird he's
an outlier yeah he built two massive castles
twitter and square which of course is now block
and for the last what five or six years he seems
completely obsessed with melting down the keys
and just handing out the scrap metal to strangers
that is the paradox that's the central enigma
we have to unpack today you have a man who is
what 49 years old now 49 worth roughly 3 .8 billion
dollars as of mid 2025. this is a person who
fundamentally shaped how the world communicates
and and how it transacts money yet if you look
at his current obsession this whole freedom technology
phase It's all about dismantling the very structures
that made him powerful and rich in the first
place. So what is it? That's the question we
have to get to. Is this some kind of guilt? Is
it a new galaxy brain strategy? Or, and this
is the interesting one to me, is it actually
the most consistent thing he's ever done? I think
it's the third one. And to understand that, we
have to get past the headlines. Oh, yeah. The
beard, the ice baths, the silent retreats. We
have to ignore all that for a minute and actually
look at the source code. And we've got a massive
stack of sources here. Biographies, corporate
filings from the early days of Odeo, even the
technical architecture of the early Twitter back
end. And of course, the white papers for the
new protocols he's funding. And when you read
through all of that, a really clear picture emerges.
You realize you can't possibly understand Twitter
and you definitely can't understand. his fascination
with Bitcoin without first understanding taxicabs.
This is what you call the dispatch theory. It
is the unifying theory of Jack Dorsey. It all
comes back to dispatch. Okay, so let's start
right there. Part one, the origin story. Yeah.
Because before he was a tech mogul, before any
of that, he was just a kid in St. Louis with
a police scanner. That's exactly it. St. Louis,
Missouri, born in 1976. And it was a very traditional
Catholic upbringing. He went to Bishop Duberg
High School. Pretty standard stuff on the surface.
But inside the house, it was a little different.
His father, Timothy, he wasn't just some generic
engineer. He worked on mass spectrometers. Right.
And let's just pause on that for a second, because
mass spectrometer is one of those terms we all
hear and we just kind of gloss over it. It sounds
complicated. It is complicated, but what it does
is simple to understand. It takes a messy reality,
a substance, and it breaks it down into its most
precise data -driven components. It tells you
exactly what something is made of. It's all about
granularity. Precisely. It's about converting
the physical world into pure, hard data. And
his mother, Marcia, was a homemaker. So she was
providing that stable home base for this very
observant kid. And he was observant because he
had to be, right? He had a speech impediment
when he was young. He was shy. Very shy. So instead
of talking, he just listened. And what he listened
to was the city. The pulse of the city itself.
Through the radio waves. Yeah, he became obsessed
with maps, but not static maps. He didn't care
about a paper map. He cared about dynamic maps.
By the time he was 14, he was glued to police
scanners, emergency frequencies, taxi dispatch
channels. Now, most people, I think, listen to
scanners for the drama. You know, there's a fire
on Fifth Street or there's a robbery in progress.
They want the story. They want the narrative.
Jack didn't care about the narrative at all.
He cared about the routing. He was listening
to the syntax of the city. The system. The system.
Think about what a dispatch system actually is.
You have hundreds of these autonomous nodes moving
around. Police cars, ambulances, couriers, taxis.
They're all operating independently. But they're
all reporting back. They're all reporting back
to a central authority with these very short...
Very structured bursts of data. Unit 1, 1023.
Unit 5, en route to Mercy Hospital. Cab 7, heading
to Lambert Airport. It's just a constant stream
of two things, state and location. That's it.
It's a real -time database of the physical world.
And he wasn't just listening. He started writing
software on his early computers to visualize
this. He wanted to see the little dots moving
on a map on his screen. He was trying to convert
the chaotic noise of the radio into a clean visual
interface of the city's pulse. That's such a
crucial insight. He wasn't interested in why
the ambulance was going somewhere. He was just
interested in the raw fact of its movement and
the efficiency of that movement. Exactly. And
that obsession basically drove his entire academic
path or, well, his detours from it. He started
at the Missouri University of Science and Technology.
Then he transferred to NYU in 1997. Which makes
total sense. If you're obsessed with dispatch,
New York City is your mecca. It's the ultimate
dispatch city. The sheer density of couriers,
taxis, delivery services. It's unlike anywhere
else in the U .S. at that time. He wanted to
be at the heart of the system. But he never actually
finished, did he? Nope. The classic Silicon Valley
dropout trope. He left one semester short of
graduating. And we should probably clear something
up here. There was a persistent rumor. for years
that he went to Cornell. Oh, right. I've heard
that. He's had to correct the record on that
personally. He never went to Cornell. It was
Missouri, S &T, then NYU, then dropout. But even
before he dropped out, he wasn't exactly, you
know, going to frat parties. He was coding. He
was trying to get into the system for real. He
was. And he actually hacked his way into a job
in a, you know, white hat kind of way. He found
a security vulnerability on the website of a
major New York dispatching company. Which one
was it? A company called Dispatch Management
Services, run by a guy named Greg Kidd. So Jack
finds this hole, and instead of exploiting it,
he emails the chairman, Greg Kidd, and basically
says, hey, your front door is unlocked. I know
how to fix it. That's a bold resume. Here is
how I broke into your house. Now hire me to install
the security system. And it worked. Kid was impressed.
He brought Jack on, and that eventually led him
to move out to California. By 2000, he's in Oakland,
and he founds his first real startup. And the
goal was? To dispatch couriers, taxis, and emergency
services using the web. Now you have to put yourself
in the year 2000. There's no iPhone, no app store.
GPS is still this bulky, expensive thing, mostly
for military and maritime use. So the technology
wasn't really there yet to support the vision.
The vision was way ahead of the tech. We've seen
his notebooks from that era. He was sketching
out these ideas for what he called frictionless
service markets. He had diagrams of networks
for medical devices reporting their status, courier
networks. What's the core idea of frictionless
there? He wanted to remove the human dispatcher
entirely. He was thinking, Why does a guy in
a call center have to tell the taxi where to
go? The software should just be able to match
the supply with the demand instantly. That is
literally the core pitch for Uber, just a decade
too early. It was Uber without the hardware to
support it. So that company didn't take off.
The infrastructure just wasn't ready. But during
this period of sort of failing and thinking,
he had this crossover idea. He was looking at
two popular things at the time, AOL, Instant
Messenger, AIM, and LiveJournal. The golden age
of the away message. He loved the away message.
Bird pizza, listening to Radiohead at the gym.
He had this flash of insight. He realized an
away message is just a dispatch update for a
human being. It's state and location again. Exactly.
It's the same pattern. And he wondered, why can
I only show this status to my buddy list? Why
can't I just dispatch my life, my status to the
entire world? He wanted to turn every person
into one of the little dots on a St. Louis map.
He wanted to visualize the pulse of humanity
the same way he visualized the pulse of the ambulances.
But again, the idea just sort of sat on a shelf.
It was a sketch in a notebook for years. He had
bills to pay. Which brings us to 2006. and a
failing podcast company audio audio it was a
podcasting startup co -founded by noah glass
and evan williams now evan williams is a key
figure here he'd already founded blogger and
sold it to google for a ton of money he was basically
silicon valley royalty And Odeo was supposed
to be his next big thing. Right. The idea was
to make it super easy for anyone to record and
share a podcast. But then in 2005, Apple completely
torpedoed their business model. Right. They released
iTunes 4 .9 with built -in podcast support. They
ate Odeo's lunch. Suddenly their entire reason
for being was redundant. So the company was just
drifting. They were burning through cash. Morale
was in the toilet. So Ev Williams says, OK, everyone
break up into teams. Let's have a hackathon.
Brainstorm something, anything to save the company.
And that's when Jack dusts off the old dispatch
idea. He pitches it to his little group, which
included Noah Glass and a designer named Biz
Stone. He describes a service that uses SMS simple
text messaging to broadcast short status updates
to a small group of friends. He called it 20TR.
With no vowels, which was very trendy at the
time. Flicker. Things like that. A fairy web
2 .0. Oh. And we have to talk about the technology
here because the limitations of 2006 literally
define the product for its first decade. This
wasn't an app you downloaded from an app store.
There was no app store. It was all based on SMS.
You would send a text message from your Nokia
or your Motorola Razr to a short code number
like 4044. Now, the global standard protocol
for SMS messaging has a hard character limit.
160 characters. 160 characters. That is a fundamental
constraint in the GSM cellular network layer.
It's not a design choice. It's a physical limitation
of the pipe. So they needed to reserve some of
those characters for the username for routing
the message. Exactly. They decided to reserve
20 characters for the username and commands,
which left 140 for the actual content of the
message. So that creative constraint that artists
and designers love to talk about, the famous
140 characters. It wasn't an artistic choice.
It was just a bandwidth limitation. It was a
technical necessity. Yeah. But it had this incredible
side effect. It forced brevity. It forced people
to communicate in headlines. It stripped everything
down to the bare essentials. So Jack and Diz
Stone, they build the prototype. In two weeks.
They hacked it together. It was raw. It was simple.
And initially, nobody at Odeo got it. The feedback
was brutal. Who cares what you're doing right
now? Why would I want to know you're eating a
sandwich? This is just narcissism. To be fair,
if you look back at the very first tweets, it
was mostly, I am eating a sandwich. Jack's first
tweet was, just setting up my TweetTR. It was.
But then something happened. An earthquake hit
San Francisco. And suddenly, people weren't tweeting
about their lunch. They were tweeting, did you
feel that? Power's out on my street. Everyone
OK. It became a real -time information network.
It became a dispatch system for reality. And
as it started to grow, as users started using
it in these unexpected ways, the infrastructure
just began to crack. It couldn't handle the load.
Which brings us to the era of the fail whale.
Oh, that iconic image. The friendly looking white
whale being lifted up by a flock of little orange
birds. Yeah. It was cute, but what it represented
was a catastrophic failure of engineering. What
was actually happening under the hood when you
saw that screen? This is so important because
it really speaks to the challenges of scaling
centralized systems. The early version of Twitter
was built on a framework called Ruby on Rails.
Now, at the time, Rails was very new and very
popular for building websites quickly. But it
wasn't built for this kind of scale. It wasn't
optimized for the kind of massive, read -write
-heavy database load that Twitter was generating.
It's what's known as a fan -out problem. Break
that down for us. What's a fan -out? Okay, so
if I have just one follower and I send a tweet,
the database has to perform one simple write
operation. Here's the tweet. Put it in my follower's
timeline. Easy. But what if I'm a celebrity with
a million followers? When I send a tweet, the
system has to fan that tweet out and update a
million different timelines or at least their
indexes almost simultaneously. So every popular
tweet was like a denial of service attack on
their own database. Essentially, yes. The database
locking was a nightmare. They were constantly
in firefighting mode, just trying to keep the
site online. The fail whale was up more than
the service was, it felt like. And this technical
chaos leads directly to the first major... turning
point in Jack's career, his ousting, his firing.
It does. The official narrative from the board
in 2008 was that Jack was an absentee CEO. Evan
Williams and the other board members, they looked
at the constant server crashes, they looked at
the complete lack of a revenue model, and then
they looked at Jack's calendar. And they saw.
They saw yoga classes. They saw fashion design
courses at a local apparel arts school. They
saw him leaving the office at 6 p .m. sharp every
day to go learn how to make skirts and draw patterns.
Okay, now, from a strictly corporate governance
perspective, if your billion -dollar startup
is literally on fire every single day, leaving
early to go sew is... It's not a good look. It
looks terrible. It looks like you don't care.
But from Jack's perspective, which he's explained
since, he was trying to understand craft. He's
always been obsessed with the aesthetics and
the utility of a product. He has this famous
metaphor where he compares Twitter to a good
pair of jeans. Utilitarian, durable, gets better
with age. Right. And he thought that by learning
a physical craft like fashion design, he could
better understand how to build a better, more
durable digital product. He thought it would
make him a better CEO. The board strongly disagreed.
They fired him. Well, they did the polite Silicon
Valley thing. They transitioned him to chairman
of the board, which is a powerless ceremonial
title. It's the nice way of saying get out of
the way and let the adults handle this. Evan
Williams took over as the full time CEO. So Jack
is in exile. But this exile period is really
interesting because he doesn't just go off and
sulk. He's still the chairman. He's still involved.
And this is when the whole State Department story
happens, isn't it? It is. This is 2009. The Green
Revolution is erupting in Iran. Massive street
protests are breaking out to dispute the results
of the presidential election. The Iranian government,
as you'd expect, clamps down hard on state media,
on cell service. But the Internet is still sort
of trickling through. And Twitter becomes the
main organizing tool. It becomes the primary
command and control network for the resistance.
People are coordinating protests, sharing videos
of police brutality, getting the word out to
the world. It was the first time we really saw
the term Twitter revolution enter the lexicon.
And right in the middle of all this, Twitter
had scheduled some server downtime. Yes, ironically.
to fix some of the very same database issues
that got Jack fired. They had a maintenance window
scheduled. They were going to take the entire
service down for a few hours. And that's when
a strictly mid -level official at the U .S. State
Department named Jared Cohen sends an email to
Jack Dorsey. And what did the email say? It essentially
said, please, please do not take the site down
right now. The protesters in Iran are using it
to organize, to report, to stay alive. Wow. That
has to be a pivotal moment. That's the moment
Twitter stops being just a quirky tech company
and starts being a genuine geopolitical actor.
Absolutely. Jack gets the email. He forwards
it to the right people at Twitter and they delay
the maintenance. They keep the service running.
And I think that moment planted a huge seed in
his head. He realized that this little dispatch
system he built wasn't just for sandwiches and
earthquakes. It was a powerful tool for freedom.
But, and this is the crucial part. It was a tool
for freedom that he and a small group of people
in San Francisco controlled. He had the switch.
He had the power to turn it off or keep it on.
The benevolent dictator problem. Exactly. And
while he was pondering that massive philosophical
problem, he went out and built another billion
-dollar company from scratch. Which brings us
to part three. Building Block, or as everyone
knew it then, Square. And once again, the origin
story starts with a simple dispatch problem.
A failed transaction. It does. It's 2009. Jack
is out of the day -to -day operations at Twitter.
He reconnects with an old friend from St. Louis
named Jim McKelvey. McKelvey had actually been
his boss at one of his first programming jobs.
And McKelvey had pivoted into a new career, right?
Yeah, he'd become a high -end glass artist, a
glassblower. And he calls Jack completely frustrated
because he'd just lost a $2 ,000 sale for one
of his glass faucets. Why? What happened? The
potential customer only had an American Express
card, and McKelvey, as a small artist, couldn't
get a merchant account that would accept Amex.
It was too expensive, too complicated. The customer
just walked away. So Jack hears this story and
sees a routing error. He sees a routing error.
The money wanted to move from point A to point
B, but the gateway was closed. The system was
broken. He looked at the state of payment processing
for small businesses at the time. It was a nightmare.
You needed a credit check. You had to pay hundreds
in monthly fees. You had to buy or lease a bulky
Verifone terminal that needed a dedicated landline.
It was totally exclusionary. It was a gated,
centralized system controlled by a few big banks
and processors. And Jack's instinct is always
to break the gate. So he and McKelvey set out
to solve this. And the technology they came up
with is just genuinely brilliant in its simplicity.
The little white square reader. The square reader.
They didn't try to build a complex new... piece
of hardware. They had a key inside. They realized
that the magnetic stripe on the back of a credit
card is just encoded data. It's just information.
And the headphone jack on a smartphone. It's
an input device. It's an analog audio input.
It's designed to listen. So they built a tiny,
cheap magnetic read head. That's the little slot
in the white square. Wired it directly to a standard
headphone plug and then wrote software on the
phone to decode the analog signal. So when you
swipe the card. the phone literally hears the
data as a screeching sound like an old dial -up
modem exactly They turned the credit card into
an MP3 file, essentially. And the software decodes
that screeching sound into the account numbers.
By doing that, they bypassed the need for hundreds
of dollars of specialized hardware. They could
manufacture the readers for pennies. Which meant
they could give them away for free. And that
changed everything. Suddenly, the person at the
farmer's market, the coffee shop, the piano teacher,
the babysitter, they were all instantly dispatched
into the modern financial system. It's the exact
same pattern as Twitter. Twitter allowed anyone
to broadcast a message. Square allowed anyone
to receive a payment. He empowers the nodes at
the edge of the network. He routes around the
central authority. And Square grew exponentially.
It was a massive success. They went public in
2015. But you have to notice the date there.
2015 is a critical year in the Jack Dorsey story.
Because that's the year Twitter came calling
again. Twitter had been drifting under its CEO
at the time, Dick Costolo. The stock was stagnant.
User growth had stalled. The product hadn't really
evolved. The board, perhaps realizing they'd
made a huge mistake years earlier, went back
to Jack, hat in hand, and asked him to come back
as CEO. But he laid down a condition. He refused
to quit Square. He demanded to be the CEO of
two publicly traded companies at the same time,
which, I mean, that's almost unheard of. Elon
Musk does it now with the Tesla and SpaceX and
X. But at that time, Wall Street viewed it as
complete insanity. So how on earth did he manage
it? Two massive companies. Through a rigorous,
almost robotic scheduling system. He themed his
days. He would literally work at the Twitter
office in the morning, then walk across the street
to the Squire office in the afternoon. Or the
themes. Monday was for management meetings at
both companies. Tuesday was for product meetings
at both companies. Wednesday was marketing and
so on. It was an incredible feat of executive
time management and, frankly, mental processing
power. But this second term at Twitter, from
2015 to 2021. this is where things get really
complicated this is where the technological monk
starts to face the demons of his own creation
he was walking back into a very different internet
The internet of 2015 was not the fun, quirky
internet of 2006. The culture wars had begun
in earnest. Disinformation was being weaponized
by state actors. And Twitter, under the previous
leadership, had made a fundamental architectural
change that Jack would later come to regret more
than anything else. They introduced the algorithmic
feed. Yes. Explain that shift for us because
it's so fundamental to understanding the problems
of social media today. Originally, your Twitter
timeline was simple. Reverse chronological. You
saw the newest tweet from the people you followed
at the very top. It was a raw, unfiltered feed
of information. Like a stock ticker. Exactly.
But in the race for engagement, to keep your
eyeballs glued to the app for longer so they
could sell more ads, they switched to a relevance
-based model. The algorithm would start guessing
what you wanted to see based on your past behavior.
It would surface the most popular or controversial
tweets and put those at the top. This is the
move that creates the echo chambers. The algorithm
learns that I get really angry about a certain
topic, so it just starts feeding me more and
more outrage about that topic because outrage
drives clicks and replies. Correct. It optimizes
for emotional reaction. not for informational
accuracy or diversity of thought. And years later,
in 2022, after he had left, Dorsey wrote this
incredible postmortem on it all. He said, and
I'm quoting here, the biggest mistake I made
was continuing to invest in building tools for
us to manage the public conversation versus building
tools for the people using Twitter to easily
manage it for themselves. Wow. That's a profound
admission of guilt, almost. He's saying we, the
company, took the power away from you, the user,
and gave it to our own engineers and our own
algorithms. That centralization of power, that
decision to manage the conversation collided
head on with the political phenomenon of Donald
Trump. The Trump presidency. This was the ultimate
stress test for Twitter's entire philosophy.
It was. You had a sitting U .S. president using
the platform as his primary communication tool,
bypassing the entire traditional media establishment.
And in doing so, he was frequently posting things
that for any other user would have been clear
violations of Twitter's own terms of service.
So Jack had a meeting with Trump in 2019 at the
White House. He did. And the readout from that
meeting is just fascinating. Apparently, Trump
spent a significant portion of the time complaining
that his follower count was dropping. He was
convinced that Jack was personally shadow banning
him to hurt him politically. And what was Jack's
response? Jack calmly explained that the company
was just. purging millions of bot and spam accounts
from the platform, and that all major accounts,
including his, were losing some followers as
a result. But for years, Dorsey defended the
decision to keep Trump on the platform, even
when the pressure was immense. He created something
called the World Leader Exception. What was the
argument there? The argument was that the public
has a right to know what their leaders are saying,
even if it's controversial or factually incorrect.
That it's more dangerous to deplatform a world
leader and drive their speech into the shadows
than it is to let it exist in the open where
it can be debated and fact checked. That was
the policy until January 6th, 2021. After the
attack on the U .S. Capitol, the internal calculus
at Twitter changed. The risk of imminent real
world violence was deemed to outweigh the newsworthiness
of the tweets. They made the decision to permanently
suspend Donald Trump's account. And Jack, as
CEO, signed off on it. But he didn't celebrate
it, which I think a lot of people expected him
to. No, not at all. And this is where people
on both sides of the aisle completely misread
him. Liberals were cheering, thinking he'd finally
seen the light. Conservatives were furious, screaming
about censorship. And Jack was, well, he seemed
mournful about it. Mournful. He posted this long
thread a few days later saying that while he
believed it was the right decision for public
safety at that moment, it was also a failure.
A failure of their platform to promote healthy
conversation. And he called it a dangerous precedent.
He realized that if one CEO in San Francisco
can unilaterally silence the president of the
United States, then that CEO simply has too much
power. And if there's one thing we've established,
it's that Jack Dorsey fundamentally distrusts
centralized power, even when it's his own. So
he's had this realization. He's seen the monster
that his creation has become. What happens next?
In November 2021, he resigns. He posts his resignation
email on Twitter. He says the company is ready
to move on from its founders. He hands the reins
over to the CTO, Parag Agarwal, and just walks
away. But he doesn't retire to an island. He
immediately rebrands Scared of Lock, Inc., and
pivots hard into what you call part four of his
story, the decentralization maximalist. This
is the part that just completely confuses the
mainstream business press. He stops talking about
quarterly earnings and ad revenue and starts
talking about cryptographic protocols. He goes
from being a tech CEO to being essentially a
Bitcoin evangelist. To Jack, Bitcoin isn't just
a speculative asset to trade. It's something
much more profound. He calls it freedom money.
He does. And we have to understand the connection
in his mind. So why? What's the link between
a dispatch system for taxes and a decentralized
digital currency? Go back to the map. In a centralized
banking system, the one we all use, the bank
is the dispatcher. They sit in the middle. They
decide if your transaction is valid. They can
freeze your account. They can reverse a transaction.
They have control. In Bitcoin, there is no central
dispatcher. The network itself is the dispatcher.
It relies on a mathematical concept called proof
of work. Can you break that down for us in simple
terms? Proof of work just means that in order
to validate a block of transactions and add it
to the blockchain, a computer, a miner, has to
expend real world energy. It has to solve a very
difficult but verifiable mathematical puzzle.
No single person or company controls this process.
It's a consensus mechanism run by thousands of
independent computers all over the world. And
Jack loves it because it's permissionless. That's
the key word. You don't need a passport or a
credit score or a bank's permission to use Bitcoin.
All you need is a private key. He sees it as
the native currency of an open Internet. Now,
we have to touch on the Internet conspiracy theories
here. There are persistent rumors that Jack himself
is Satoshi Nakamoto, the anonymous creator of
Bitcoin. It's a very fun theory to entertain.
I mean, he has the deep cryptographic background.
You have to remember the early dispatch services
he built were all about secure encrypted communication.
He certainly has the cypherpunk philosophy of
privacy and decentralization. And he was in the
right place at the right time. So do you think
it's true? I would say it's highly, highly unlikely.
During the critical period when Satoshi was actively
coding and writing about Bitcoin, from 2008 to
2010, Jack was in the middle of getting fired
from Twitter and launching Square. He was a little
busy. But spiritually, I think he sees himself
as Satoshi's most important disciple. He's on
record saying he believes Bitcoin is one of the
most important developments for the future of
world peace. World peace. That's a... That is
a very big claim for a digital currency. It sounds
hyperbolic, but his argument has a certain logic
to it. His argument is that most major wars are
funded by governments endlessly printing money,
devaluing their currency to pay for armies and
weapons. If a government had to operate on a
sound money standard like Bitcoin that they couldn't
inflate, it would be much harder to fund perpetual
conflict. It's an anti -war technology in his
view. And he's putting his company's money and
his own money where his mouth is. He funded a
project called Ocean. Right. Ocean is a Bitcoin
mining pool. See, one of the problems Bitcoin
has right now is that the mining process itself
is becoming more centralized. A few huge publicly
traded companies control a massive percentage
of the global hash rate. Which creates a new
central point of failure. It does. If those few
companies were ever to collude or be forced by
a government to do so, they could theoretically
censor certain transactions. Ocean is what's
known as a non -custodial mining pool. It allows
small individual miners to pool their resources
and earn rewards without ever giving up control
of their hardware to a central operator. It's
about decentralizing the decentralization. And
there's the other side of it. He gave up on Twitter
as a company, but he clearly didn't give up on
the idea of social networking. He just. thinks
it shouldn't be a company. This brings us to
the whole Blueski versus Nostra saga. It's really
revealing. Right. Blueski was his own project,
started inside Twitter. He started Blueski at
Twitter in 2019 with the goal of building an
open, decentralized social media protocol. The
long -term vision was that Twitter itself would
eventually just become one of many clients that
could plug into this open standard. But after
he left Twitter, Blueski spun off into its own
independent company. It did. It took on venture
capital funding. It formed a public benefit corporation.
It appointed a board, which Jack sat on. And
it started doing all the things companies do.
It started building centralized moderation tools.
It started acting like... Twitter. And Jack hated
it. He grew disillusioned. In May of 2024, he
very publicly left the blue ski board. He deleted
his account and said they were repeating all
the mistakes we made at Twitter. He doesn't want
a better, more decentralized Twitter. He wants
no Twitter. He wants a protocol, not a platform.
So he pivoted all his support and energy to Noster.
Noster, which stands for notes and other stuff
transmitted by relays. It's a terrible name.
It's a terrible name, but the concept is what
matters to him. So what makes it fundamentally
different from BlueSky or Twitter? Noster isn't
a platform. It's a protocol, just like email
or HTTP are protocols. No single person or company
owns email, right? You can use Gmail. I can use
Outlook. A company can run its own server and
we can all still talk to each other. Right. Nostra
is the same for social media. There is no central
Nostra server. There's no Nostra Inc. So where
does the data actually live? It lives on a network
of independent relays. Anyone can run a relay.
You can run one on a cheap computer in your basement.
When I want to post a message, I sign it with
my private cryptographic key. That's my uncensorable
identity. And I send it out to a handful of relays
that I like. Your app, your client, just connects
to those same relays and pulls my message down.
So if a relay owner decides, I don't like what
this person is saying, and they ban you from
their relay, what happens? Nothing, really. I
just start sending my messages to different relays.
My identity isn't tied to any one server. It's
tied to my cryptographic key. It is designed
from the ground up to be censorship resistant.
And he's even thinking beyond the internet now.
He's been talking about Bluetooth mesh networks.
This is the most radical step. This is for a
situation where the internet itself goes down.
Imagine a large protest where a government decides
to shut down all the cell towers and cut off
Internet access. Bluetooth mesh allows phones
to talk directly to each other, peer to peer.
Like a daisy chain of data. A digital bucket
brigade. My phone talks to your phone, which
talks to the phone next to you. It creates a
local ad hoc network with no central infrastructure
at all. He funded an app in 2025 called BitChat
that uses this technology. It is dispatching
without a dispatcher. ultimate realization of
that teenage dream of watching dots move on a
map. But now with no central tower controlling
them, it's incredible how consistent the core
philosophy is from a scanner in St. Louis all
the way to blockchain protocols. But we have
to look at the man himself, part five, because
the way he lives his life is. Just as intense
and just as extreme as the software he funds.
Yeah, we have to talk about the technological
monk persona because it's not just an act. He
lives in Seacliff, a beautiful neighborhood in
San Francisco, has a $10 million compound overlooking
the Golden Gate Bridge. But by all accounts,
inside that house, he lives like an ascetic.
The meditation is a huge part of it. A huge part.
He practices Vipassana meditation. And we need
to be clear, this isn't the kind of mindfulness
you do on a five -minute app. This is an ancient,
rigorous, demanding tradition. In late 2017,
he did a 10 -day silent retreat. Walk us through
what that actually entails. It's intense. You
wake up at 4 a .m. You meditate something like
10 hours a day. You're not allowed to eat after
midday. No reading, no writing, no phones, no
music. You don't even make eye contact with the
other people there. You are completely and totally
alone with your own mind for 10 straight days.
For a guy whose brain seems to be wired for constant
high speed data inputs, that must have been excruciatingly
difficult. He said it was one of the most painful
and difficult things he's ever done. But he believes
it's necessary to, in his words, hack his own
brain to debug. his own mental source code and
see the world as it really is. But that intense
inward focus can have a huge blind spot. It can
backfire. We have to address the Myanmar trip.
We do. In 2018, for his birthday, he went to
Myanmar to do another one of these meditation
retreats. And when he came out, he tweeted about
how beautiful the country was, how peaceable
and kind the people were. And he posted this
at the exact same time that the Myanmar military
was in the middle of conducting a brutal genocide
against the Rohingya Muslim minority. It was
a massive, unforced PR disaster. Critics, I think,
rightfully pointed out that his own platform,
Twitter, had been used as a tool to spread hate
speech and incite violence against the Rohingya.
And here he was, the CEO, essentially promoting
tourism to the country without even acknowledging
the atrocities that were happening. It suggests
a kind of profound tunnel vision. He was so focused
on achieving his own internal silence that he
completely tuned out the screams of external
suffering. That is the dark side, the shadow
side of that monk archetype. An extreme level
of detachment can start to look a lot like indifference.
Let's pivot to his politics, though. Yeah. Because
you absolutely cannot put him in a simple box.
Oh, he's a complete nightmare for political pundits
who want to label everyone. In the 2020 Democratic
primary, he donated to two candidates. Tulsi
Gabbard and Andrew Yang. But both definite outsiders.
Yang, of course, was a universal basic income
candidate. And UBI is a huge passion for Jack.
Right. But then fast forward to 2024 and he very
publicly endorses Robert F. Kennedy Jr. for president.
Who is the ultimate anti -establishment chaos
agent. RFK Jr.'s entire platform is built on
challenging the pharmaceutical industry, the
intelligence agencies, the mainstream media,
basically questioning every official narrative.
And Jack loves that questioning spirit. But here's
the twist. At the same time he's supporting RFK
Jr., he donates $10 million to Boston University's
Center for Anti -Racist Research, founded by
Dr. Ibram X. Kendi. The leading academic scholar
of what's often called critical race theory.
Exactly. So on one hand, you have RFK Jr., and
on the other, you have Ibram X. Kendi. Most people
would look at that and see a complete contradiction,
a political schizophrenic. But I think in Jack's
mind, it's perfectly consistent. How do you square
that circle? They are both in their own ways
challenging the system. Kendi is challenging
the systemic power structures of race in America.
RFK is challenging the systemic power structures
of government and corporations. Jack is fundamentally
anti -centralization. He will support anyone
he sees as trying to break up the big monolithic
blobs of power. He's also tweeted in. support
of the Gaza war protests and even drew parallels
to the Vietnam and Iraq war protests. He's very
consistently anti -war. Because war is the ultimate,
most violent expression of the centralized state.
He's a libertarian in the truest nonpartisan
sense of that word. He trusts individuals over
institutes every single time. And that trust
in individuals is the driving force behind his
philanthropy, right? The start small initiative.
This is one of the most interesting things he's
done. It's April 2020. The COVID -19 pandemic
is just starting to explode globally. Jack takes
$1 billion of his equity in Square, which at
the time was about 28 % of his total net worth,
and he moves it into a new entity. But it wasn't
a typical foundation. No. He didn't create a
501C foundation, which comes with a board of
directors, huge overhead costs and a slow bureaucratic
process. He moved it into a simple LLC, a limited
liability company. What's the practical difference
there? An LLC is just a company. He is the sole
member. He can write a check to anyone for any
reason in five minutes. It's agile. And he did
something truly radical for transparency. The
Google sheet. The Google sheet. He tweeted out
a public link to a Google spreadsheet. It's called
the Start Small Tracker. You can go look at it
right now. It is a line -by -line public ledger
of every single donation he has made from that
billion dollars. So you can see it all. $10 million
to the Reform Alliance for criminal justice reform.
$20 million to CORE for COVID relief. $15 million
for oxygen concentrators for India. It's all
just there. Why a Google sheet? Because it's
the dispatch aesthetic again. It's raw data.
It's not a glossy annual report or a press release.
It's just a ledger. He wants you to see the real
-time flow of the money unvarnished. And a huge
amount of that money, as you mentioned with Andrew
Yang, goes to universal basic income experiments.
A huge amount. He's the primary funder for a
group called Mayors for a Guaranteed Income.
He believes that the most efficient and dignified
way to help people isn't to create a complex,
top -down welfare bureaucracy. That's just another
centralized dispatcher. He wants to just give
people the money. Just give them the cash, a
direct peer -to -peer transfer, and trust them
to solve their own problems in their own way.
He trusts the nodes at the edge of the network
more than he trusts the hub in the center. So
if we pull the lens back. We have this incredible
picture of a man who spent the first half of
his career building these massive centralized
systems to route information and money and is
now spending the entire second half of his career
trying to build the tools that will make his
own original creations obsolete. He wants to
abdicate the throne he built. He wants to be
the technological monk who writes the code, sets
it free in the world, and then disappears back
into the meditation hall. But we have to end
with a harder question. Is he right? That is
the multi -trillion dollar gamble of the 21st
century. Because we have seen what happens on
largely unmoderated decentralized platforms.
You get floods of hate speech. You get coordinated
harassment campaigns. You get state -sponsored
bot armies. You get chaos. If you remove the
dispatcher, if you fire all the trust and safety
teams, does society actually function? Or does
it just crash and burn? Jack's argument would
be that the crash isn't caused by freedom. It's
caused by the centralized engagement based algorithms
that are manipulating us and amplifying the worst
aspects of human nature for profit. He truly
believes that if you give people tools that they
own and control where they can choose their own
algorithm or have no algorithm at all, that rationality
and good faith will eventually return. He has
a deep, almost religious faith in the wisdom
of the crowd in its purest, most unfiltered form.
He trusts the nodes. Full stop. It's a beautiful
vision. Maybe it's a naive vision. Maybe it's
the only way forward. But when you look at the
world we live in right now, a world of AI -generated
deepfakes, of pervasive information warfare,
The idea of taking all the guardrails off seems
terrifyingly risky. It is incredibly risky. But
Jack looks at the alternative, a world where
a Mark Zuckerberg or an Elon Musk or a government
bureaucrat gets to be the final arbiter of what
is true. And he thinks that is the far greater
danger. So he's essentially handing out the matches
and hoping we collectively decide not to burn
the house down. Or he's hoping we realize we
can use the fire to cook dinner and warm ourselves.
It's a story that's still being written. And
whether he is Satoshi or not, he is certainly
the most Satoshi -like public figure we have.
He embodies that spirit. He is the ultimate anti
-CEO. We covered a ton of ground today. Mass
spectrometers in St. Louis, silent retreats in
Myanmar, the architecture of the blockchain.
We didn't even get to really deep dive on his
acquisition of the Music Streaming Service title,
but that's a whole other story about empowering
artists. Maybe for another day. I think the final
thought, the thing for you, the listener, to
take away from this is to just look at the digital
tools you use every single day. Look at your
social media feed, your bank account, your messaging
apps, and ask yourself, who owns the map? Who
is the dispatcher? And is it time you started
dispatching yourself? That's the question he
wants everyone to ask. Thanks for listening to
The Deep Dive. We'll see you next time.