The dictator's playbook.

Stalin's successor, Nikita Khrushchev, delivered a speech titled "On The Cult Of Personality And Its Consequences" in 1956, three years after Stalin’s death.

The speech, which was never made public, shook the Soviet Union and the Soviet Bloc. After Stalin's "cult of personality" was exposed as a lie, only reality remained.

As I've watched the nightmare unfold in Ukraine, I'm reminded of that question. Primarily by Putin's repeated denials.

His odd claim that Ukraine is run by drug addicts and Nazis (especially strange given that Volodymyr Zelenskyy, the Ukrainian president, is Jewish). Others attempt to portray Russia as liberators rather than occupiers. For example, he portrays Luhansk and Donetsk as plucky, newly independent states when they have been totalitarian statelets for 8 years.

Putin seemed to have lost all sense of reality.

Maybe that's why his remarks to an oligarchs' gathering stood out:

This is almost certainly true from Putin's perspective. Even for Putin, a military invasion seems unlikely. So, what exactly is putting Russia's security in jeopardy? How could Ukraine's independence endanger Russia's existence?

The truth is the only thing that truly terrifies leaders like these.

Trump, the president of “alternative facts,” "and “fake news” praised Putin's fabricated justifications for the Ukraine invasion. Russia tightened news censorship as news of their losses came in. It's no accident that modern dictatorships like Russia (and China and North Korea) restrict citizens' access to information.

Controlling what people see, hear, and think is the simplest method. And Ukraine's recent efforts to join the European Union showed a country whose thoughts Putin couldn't control. With the Russian and Ukrainian peoples so close, he could not control their reality.
He appears to think this is a threat worth fighting NATO over.

It's easy to disown history's great dictators. By the magnitude of their harm. But the strategy they used is still in use today, albeit not to the same devastating effect.

The Kim dynasty in North Korea has ruled for 74 years, Putin has ruled Russia for 19 years (using loopholes and even rewriting the constitution).

When their egos are threatened, they sabre-rattle, as in Kim Jong-un and Donald Trump's famous spat about the size of their...ahem, “nuclear buttons”." Or Putin's threats of mutual destruction this weekend.

Most importantly, they have cult-like control over their followers.

When a leader whose power is built on lies feels he is losing control of the narrative, things like Trump's Jan. 6 meltdown and Putin's current actions in Ukraine are unavoidable.

Leaders who try to control their people's reality will have to die to keep the illusion alive.

Long version of this post available here

Transcript:

[Reporter] The Russian invasion of Ukraine.
Momentum is building for a war between Ukraine and Russia.
[Reporter] Tensions between Russia and the West
are growing rapidly.
[Reporter] President Biden considering deploying
thousands of troops to Eastern Europe.
There are now 100,000 troops
on the Eastern border of Ukraine.
Russia is setting up field hospitals on this border.
Like this is what preparation for war looks like.
A legitimate war.
Ukrainian troops are watching and waiting,
saying they are preparing for a fight.
The U.S. has ordered the families of embassy staff
to leave Ukraine.
Britain has sent all of their nonessential staff home.
And now the U.S. is sending tons of weapons and munitions
to Ukraine's army.
And we're even considering deploying
our own troops to the region.
I mean, this thing is heating up.
Meanwhile, Russia and the West have been in Geneva
and Brussels trying to talk it out,
and sort of getting nowhere.
The message is very clear.
Should Russia take further aggressive actions
against Ukraine the costs will be severe
and the consequences serious.
It's a scary, grim momentum that is unpredictable.
And the chances of miscalculation
and escalation are growing.

I want to explain what's going on here,
but I want to show you that this isn't just
typical geopolitical behavior.
Stuff that can just be explained on the map.
Instead, to understand why 100,000 troops are camped out
on Ukraine's Eastern border, ready for war,
you have to understand Russia
and how it's been cut down over the ages
from the Slavic empire that dominated this whole region
to then the Soviet Union,
which was defeated in the nineties.
And what you really have to understand here
is how that history is transposed
onto the brain of one man.
This guy, Vladimir Putin.
This is a story about regional domination
and struggles between big powers,
but really it's the story about
what Vladimir Putin really wants.
[Reporter] Russian troops moving swiftly
to take control of military bases in Crimea.
[Reporter] Russia has amassed more than 100,000 troops
and a lot of military hardware
at the border with Ukraine.

Let's dive back in.
Okay. Let's get up to speed on what's happening here.
And I'm just going to quickly give you the highlight version
of like the news that's happening,
because I want to get into the juicy part,
which is like why, the roots of all of this.
So let's go.
A few months ago, Russia started sending
more and more troops to this border.
It's this massive border between Ukraine and Russia.
They said they were doing a military exercise,
but the rest of the world was like,
"Yeah, we totally believe you Russia. Pshaw."
This was right before this big meeting
where North American and European countries
were coming together to talk about a lot
of different things, like these countries often do
in these diplomatic summits.
But soon, because of Russia's aggressive behavior
coming in and setting up 100,000 troops
on the border with Ukraine,
the entire summit turned into a whole, "WTF Russia,
what are you doing on the border of Ukraine," meeting.
Before the meeting Putin comes out and says,
"Listen, I have some demands for the West."
And everyone's like, "Okay, Russia, what are your demands?
You know, we have like, COVID19 right now.
And like, that's like surging.

So like, we don't need your like,
bluster about what your demands are."
And Putin's like, "No, here's my list of demands."
Putin's demands for the summit were this:
number one, that NATO, which is this big military alliance
between U.S., Canada, and Europe stop expanding,
meaning they don't let any new members in, okay.
So, Russia is like, "No more new members to your, like,
cool military club that I don't like.
You can't have any more members."
Number two, that NATO withdraw all of their troops
from anywhere in Eastern Europe.
Basically Putin is saying,
"I can veto any military cooperation
or troops going between countries
that have to do with Eastern Europe,
the place that used to be the Soviet Union."
Okay, and number three, Putin demands that America vow
not to protect its allies in Eastern Europe
with nuclear weapons.
"LOL," said all of the other countries,
"You're literally nuts, Vladimir Putin.
Like these are the most ridiculous demands, ever."
But there he is, Putin, with these demands.
These very, very aggressive demands.
And he sort of is implying that if his demands aren't met,
he's going to invade Ukraine.
I mean, it doesn't work like this.
This is not how international relations work.
You don't just show up and say like,
"I'm not gonna allow other countries to join your alliance
because it makes me feel uncomfortable."
But what I love about this list of demands
from Vladimir Putin for this summit
is that it gives us a clue
on what Vladimir Putin really wants.

What he's after here.
You read them closely and you can grasp his intentions.
But to grasp those intentions
you have to understand what NATO is.
and what Russia and Ukraine used to be.
(dramatic music)
Okay, so a while back I made this video
about why Russia is so damn big,
where I explain how modern day Russia started here in Kiev,
which is actually modern day Ukraine.
In other words, modern day Russia, as we know it,
has its original roots in Ukraine.
These places grew up together
and they eventually became a part
of the same mega empire called the Soviet Union.
They were deeply intertwined,
not just in their history and their culture,
but also in their economy and their politics.
So it's after World War II,
it's like the '50s, '60s, '70s, and NATO was formed,
the North Atlantic Treaty Organization.
This was a military alliance between all of these countries,
that was meant to sort of deter the Soviet Union
from expanding and taking over the world.
But as we all know, the Soviet Union,
which was Russia and all of these other countries,
collapsed in 1991.
And all of these Soviet republics,
including Ukraine, became independent,
meaning they were not now a part
of one big block of countries anymore.
But just because the border's all split up,
it doesn't mean that these cultural ties actually broke.
Like for example, the Soviet leader at the time
of the collapse of the Soviet Union, this guy, Gorbachev,
he was the son of a Ukrainian mother and a Russian father.
Like he grew up with his mother singing him
Ukrainian folk songs.

In his mind, Ukraine and Russia were like one thing.
So there was a major reluctance to accept Ukraine
as a separate thing from Russia.
In so many ways, they are one.
There was another Russian at the time
who did not accept this new division.
This young intelligence officer, Vladimir Putin,
who was starting to rise up in the ranks
of postSoviet Russia.
There's this amazing quote from 2005
where Putin is giving this stateoftheunionlike address,
where Putin declares the collapse of the Soviet Union,
quote, "The greatest catastrophe of the 20th century.
And as for the Russian people, it became a genuine tragedy.
Tens of millions of fellow citizens and countrymen
found themselves beyond the fringes of Russian territory."
Do you see how he frames this?
The Soviet Union were all one people in his mind.
And after it collapsed, all of these people
who are a part of the motherland were now outside
of the fringes or the boundaries of Russian territory.
First off, fact check.
Greatest catastrophe of the 20th century?
Like, do you remember what else happened
in the 20th century, Vladimir?
(ominous music)

Putin's worry about the collapse of this one people
starts to get way worse when the West, his enemy,
starts showing up to his neighborhood
to all these exSoviet countries that are now independent.
The West starts selling their ideology
of democracy and capitalism and inviting them
to join their military alliance called NATO.
And guess what?
These countries are totally buying it.
All these exSoviet countries are now joining NATO.
And some of them, the EU.
And Putin is hating this.
He's like not only did the Soviet Union divide
and all of these people are now outside
of the Russia motherland,
but now they're being persuaded by the West
to join their military alliance.
This is terrible news.
Over the years, this continues to happen,
while Putin himself starts to chip away
at Russian institutions, making them weaker and weaker.
He's silencing his rivals
and he's consolidating power in himself.
(triumphant music)

And in the past few years,
he's effectively silenced anyone who can challenge him;
any institution, any court,
or any political rival have all been silenced.
It's been decades since the Soviet Union fell,
but as Putin gains more power,
he still sees the region through the lens
of the old Cold War, Soviet, Slavic empire view.
He sees this region as one big block
that has been torn apart by outside forces.
"The greatest catastrophe of the 20th century."
And the worst situation of all of these,
according to Putin, is Ukraine,
which was like the gem of the Soviet Union.
There was tons of cultural heritage.
Again, Russia sort of started in Ukraine,
not to mention it was a very populous
and industrious, resourcerich place.
And over the years Ukraine has been drifting west.
It hasn't joined NATO yet, but more and more,
it's been electing proWestern presidents.
It's been flirting with membership in NATO.
It's becoming less and less attached
to the Russian heritage that Putin so adores.
And more than half of Ukrainians say
that they'd be down to join the EU.
64% of them say that it would be cool joining NATO.
But Putin can't handle this. He is in total denial.
Like an exboyfriend who handle his exgirlfriend
starting to date someone else,
Putin can't let Ukraine go.
He won't let go.

So for the past decade,
he's been trying to keep the West out
and bring Ukraine back into the motherland of Russia.
This usually takes the form of Putin sending
secret soldiers from Russia into Ukraine
to help the people in Ukraine who want to like separate
from Ukraine and join Russia.
It also takes the form of, oh yeah,
stealing entire parts of Ukraine for Russia.
Russian troops moving swiftly to take control
of military bases in Crimea.
Like in 2014, Putin just did this.
To what America is officially calling
a Russian invasion of Ukraine.
He went down and just snatched this bit of Ukraine
and folded it into Russia.
So you're starting to see what's going on here.
Putin's life's work is to salvage what he calls
the greatest catastrophe of the 20th century,
the division and the separation
of the Soviet republics from Russia.
So let's get to present day. It's 2022.
Putin is at it again.
And honestly, if you really want to understand
the mind of Vladimir Putin and his whole view on this,
you have to read this.
"On the History of Unity of Russians and Ukrainians,"
by Vladimir Putin.
A blog post that kind of sounds
like a ninth grade history essay.
In this essay, Vladimir Putin argues
that Russia and Ukraine are one people.
He calls them essentially the same historical
and spiritual space.

Kind of beautiful writing, honestly.
Anyway, he argues that the division
between the two countries is due to quote,
"a deliberate effort by those forces
that have always sought to undermine our unity."
And that the formula they use, these outside forces,
is a classic one: divide and rule.
And then he launches into this super indepth,
like 10page argument, as to every single historical beat
of Ukraine and Russia's history
to make this argument that like,
this is one people and the division is totally because
of outside powers, i.e. the West.
Okay, but listen, there's this moment
at the end of the post,
that actually kind of hit me in a big way.
He says this, "Just have a look at Austria and Germany,
or the U.S. and Canada, how they live next to each other.
Close in ethnic composition, culture,
and in fact, sharing one language,
they remain sovereign states with their own interests,
with their own foreign policy.
But this does not prevent them
from the closest integration or allied relations.
They have very conditional, transparent borders.
And when crossing them citizens feel at home.
They create families, study, work, do business.
Incidentally, so do millions of those born in Ukraine
who now live in Russia.
We see them as our own close people."
I mean, listen, like,
I'm not in support of what Putin is doing,
but like that, it's like a pretty solid like analogy.
If China suddenly showed up and started like
coaxing Canada into being a part of its alliance,
I would be a little bit like, "What's going on here?"
That's what Putin feels.
And so I kind of get what he means there.
There's a deep heritage and connection between these people.
And he's seen that falter and dissolve
and he doesn't like it.
He clearly genuinely feels a brotherhood
and this deep heritage connection
with the people of Ukraine.
Okay, okay, okay, okay. Putin, I get it.
Your essay is compelling there at the end.
You're clearly very smart and wellread.
But this does not justify what you've been up to. Okay?
It doesn't justify sending 100,000 troops to the border
or sending cyber soldiers to sabotage
the Ukrainian government, or annexing territory,
fueling a conflict that has killed
tens of thousands of people in Eastern Ukraine.
No. Okay.

No matter how much affection you feel for Ukrainian heritage
and its connection to Russia, this is not okay.
Again, it's like the boyfriend
who genuinely loves his girlfriend.
They had a great relationship,
but they broke up and she's free to see whomever she wants.
But Putin is not ready to let go.
[Man In Blue Shirt] What the hell's wrong with you?
I love you, Jessica.
What the hell is wrong with you?
Dude, don't fucking touch me.
I love you. Worldstar!
What is wrong with you? Just stop!
Putin has constructed his own reality here.
One in which Ukraine is actually being controlled
by shadowy Western forces
who are holding the people of Ukraine hostage.
And if that he invades, it will be a swift victory
because Ukrainians will accept him with open arms.
The great liberator.
(triumphant music)

Like, this guy's a total romantic.
He's a history buff and a romantic.
And he has a hill to die on here.
And it is liberating the people
who have been taken from the Russian motherland.
Kind of like the abusive boyfriend, who's like,
"She actually really loves me,
but it's her annoying friends
who were planting all these ideas in her head.
That's why she broke up with me."
And it's like, "No, dude, she's over you."
[Man In Blue Shirt] What the hell is wrong with you?
I love you, Jessica.
I mean, maybe this video should be called
Putin is just like your abusive exboyfriend.
[Man In Blue Shirt] What the hell is wrong with you?
I love you, Jessica!
Worldstar! What's wrong with you?
Okay. So where does this leave us?
It's 2022, Putin is showing up to these meetings in Europe
to tell them where he stands.
He says, "NATO, you cannot expand anymore. No new members.
And you need to withdraw all your troops
from Eastern Europe, my neighborhood."
He knows these demands will never be accepted
because they're ludicrous.
But what he's doing is showing a false effort to say,
"Well, we tried to negotiate with the West,
but they didn't want to."
Hence giving a little bit more justification
to a Russian invasion.
So will Russia invade? Is there war coming?
Maybe; it's impossible to know
because it's all inside of the head of this guy.
But, if I were to make the best argument
that war is not coming tomorrow,
I would look at a few things.
Number one, war in Ukraine would be incredibly costly
for Vladimir Putin.
Russia has a far superior army to Ukraine's,
but still, Ukraine has a very good army
that is supported by the West
and would give Putin a pretty bad bloody nose
in any invasion.

Controlling territory in Ukraine would be very hard.
Ukraine is a giant country.
They would fight back and it would be very hard
to actually conquer and take over territory.
Another major point here is that if Russia invades Ukraine,
this gives NATO new purpose.
If you remember, NATO was created because of the Cold War,
because the Soviet Union was big and nuclear powered.
Once the Soviet Union fell,
NATO sort of has been looking for a new purpose
over the past couple of decades.
If Russia invades Ukraine,
NATO suddenly has a brand new purpose to unite
and to invest in becoming more powerful than ever.
Putin knows that.
And it would be very bad news for him if that happened.
But most importantly, perhaps the easiest clue
for me to believe that war isn't coming tomorrow
is the Russian propaganda machine
is not preparing the Russian people for an invasion.
In 2014, when Russia was about to invade
and take over Crimea, this part of Ukraine,
there was a barrage of state propaganda
that prepared the Russian people
that this was a justified attack.
So when it happened, it wasn't a surprise
and it felt very normal.

That isn't happening right now in Russia.
At least for now. It may start happening tomorrow.
But for now, I think Putin is showing up to the border,
flexing his muscles and showing the West that he is earnest.
I'm not sure that he's going to invade tomorrow,
but he very well could.
I mean, read the guy's blog post
and you'll realize that he is a romantic about this.
He is incredibly idealistic about the glory days
of the Slavic empires, and he wants to get it back.
So there is dangerous momentum towards war.
And the way war works is even a small little, like, fight,
can turn into the other guy
doing something bigger and crazier.
And then the other person has to respond
with something a little bit bigger.
That's called escalation.
And there's not really a ceiling
to how much that momentum can spin out of control.
That is why it's so scary when two nuclear countries
go to war with each other,
because there's kind of no ceiling.
So yeah, it's dangerous. This is scary.
I'm not sure what happens next here,
but the best we can do is keep an eye on this.
At least for now, we better understand
what Putin really wants out of all of this.

Thanks for watching.

War's Human Cost
I didn't start crying until I was outside a McDonald's in an Olempin, Poland rest area on highway S17.

Children pick toys at a refugee center, Olempin, Poland, March 4, 2022.

Refugee children, mostly alone with their mothers, but occasionally with a gray-haired grandfather or non-Ukrainian father, were coaxed into picking a toy from boxes provided by a kind-hearted company and volunteers.
I went to Warsaw to continue my research on my family's history during the Holocaust. In light of the ongoing Ukrainian conflict, I asked former colleagues in the US Department of Defense and Intelligence Community if it was safe to travel there. They said yes, as Poland was a NATO member.
I stayed in a hotel in the Warsaw Ghetto, where 90% of my mother's family was murdered in the Holocaust. Across the street was the first Warsaw Judenrat. It was two blocks away from the apartment building my mother's family had owned and lived in, now dilapidated and empty.

Building of my great-grandfather, December 2021.

A mass grave of thousands of rocks for those killed in the Warsaw Ghetto, I didn't cry when I touched its cold walls.

Warsaw Jewish Cemetery, 200,000–300,000 graves.

Mass grave, Warsaw Jewish Cemetery.

My mother's family had two homes, one in Warszawa and the rural one was a forest and sawmill complex in Western Ukraine. For the past half-year, a local Ukrainian historian had been helping me discover faint traces of her family’s life there — in fact, he had found some people still alive who remembered the sawmill and that it belonged to my mother’s grandfather. The historian was good at his job, and we had become close.

My historian friend, December 2021, talking to a Ukrainian.

With war raging, my second trip to Warsaw took on a different mission. To see his daughter and one-year-old grandson, I drove east instead of to Ukraine. They had crossed the border shortly after the war began, leaving men behind, and were now staying with a friend on Poland's eastern border.
I entered after walking up to the house and settling with the dog. The grandson greeted me with a huge smile and the Ukrainian word for “daddy,” “Tato!” But it was clear he was awaiting his real father's arrival, and any man he met would be so tentatively named.
After a few moments, the boy realized I was only a stranger. He had musical talent, like his mother and grandfather, both piano teachers, as he danced to YouTube videos of American children's songs dubbed in Ukrainian, picking the ones he liked and crying when he didn't.

Songs chosen by my historian friend's grandson, March 4, 2022

He had enough music and began crying regardless of the song. His mother picked him up and started nursing him, saying she was worried about him. She had no idea where she would live or how she would survive outside Ukraine. She showed me her father's family history of losses in the Holocaust, which matched my own research.
After an hour of drinking tea and trying to speak of hope, I left for the 3.5-hour drive west to Warsaw.
It was unlike my drive east. It was reminiscent of the household goods-filled carts pulled by horses and people fleeing war 80 years ago.

Jewish refugees relocating, USHMM Holocaust Encyclopaedia, 1939.

The carefully chosen trinkets by children to distract them from awareness of what is really happening and the anxiety of what lies ahead, made me cry despite all my research on the Holocaust. There is no way for them to communicate with their mothers, who are worried, absent, and without their fathers.
It's easy to see war as a contest of nations' armies, weapons, and land. The most costly aspect of war is its psychological toll. My father screamed in his sleep from nightmares of his own adolescent trauma in Warsaw 80 years ago.

Survivor father studying engineering, 1961.

In the airport, I waited to return home while Ukrainian public address systems announced refugee assistance. Like at McDonald's, many mothers were alone with their children, waiting for a flight to distant relatives.
That's when I had my worst trip experience.
A woman near me, clearly a refugee, answered her phone, cried out, and began wailing.
The human cost of war descended like a hammer, and I realized that while I was going home, she never would

Full article

On Election Day 2020, two young entrepreneurs received a call from the CFTC chairman. Luana Lopes Lara and Tarek Mansour spent 18 months trying to start a new type of financial exchange. Instead of betting on stock prices or commodity futures, people could trade instruments tied to real-world events, such as legislation, the weather, or the Oscar winner.

Heath Tarbert, a Trump appointee, shouted "Congratulations." "You're competing with 1840s-era markets. I'm sure you'll become a powerhouse too."

Companies had tried to introduce similar event markets in the US for years, but Tarbert's agency, the CFTC, said no, arguing they were gambling and prone to cheating. Now the agency has reversed course, approving two 24-year-olds who will have first-mover advantage in what could become a huge new asset class. Kalshi Inc. raised $30 million from venture capitalists within weeks of Tarbert's call, his representative says. Mansour, 26, believes this will be bigger than crypto.

Anyone who's read The Wisdom of Crowds knows prediction markets' potential. Well-designed markets can help draw out knowledge from disparate groups, and research shows that when money is at stake, people make better predictions. Lopes Lara calls it a "bullshit tax." That's why Google, Microsoft, and even the US Department of Defense use prediction markets internally to guide decisions, and why university-linked political betting sites like PredictIt sometimes outperform polls.

Regulators feared Wall Street-scale trading would encourage investors to manipulate reality. If the stakes are high enough, traders could pressure congressional staffers to stall a bill or bet on whether Kanye West's new album will drop this week. When Lopes Lara and Mansour pitched the CFTC, senior regulators raised these issues. Politically appointed commissioners overruled their concerns, and one later joined Kalshi's board.

Kalshi's victory was due more to lobbying and legal wrangling than to Silicon Valley-style innovation. Lopes Lara and Mansour didn't invent anything; they changed a well-established concept's governance. The result could usher in a new era of market-based enlightenment or push Wall Street's destructive tendencies into the real world.

If Kalshi's founders lacked experience to bolster their CFTC application, they had comical youth success. Lopes Lara studied ballet at the Brazilian Bolshoi before coming to the US. Mansour won France's math Olympiad. They bonded over their work ethic in an MIT computer science class.

Lopes Lara had the idea for Kalshi while interning at a New York hedge fund. When the traders around her weren't working, she noticed they were betting on the news: Would Apple hit a trillion dollars? Kylie Jenner? "It was anything," she says.

Mansour saw the business potential when Lopes Lara suggested it. He interned at Goldman Sachs Group Inc., helping investors prepare for the UK leaving the EU. Goldman sold clients complex stock-and-derivative combinations. As he discussed it with Lopes Lara, they agreed that investors should hedge their risk by betting on Brexit itself rather than an imperfect proxy.

Lopes Lara and Mansour hypothesized how a marketplace might work. They settled on a "event contract," a binary-outcome instrument like "Will inflation hit 5% by the end of the month?" The contract would settle at $1 (if the event happened) or zero (if it didn't), but its price would fluctuate based on market sentiment. After a good debate, a politician's election odds may rise from 50 to 55. Kalshi would charge a commission on every trade and sell data to traders, political campaigns, businesses, and others.

In October 2018, five months after graduation, the pair flew to California to compete in a hackathon for wannabe tech founders organized by the Silicon Valley incubator Y Combinator. They built a website in a day and a night and presented it to entrepreneurs the next day. Their prototype barely worked, but they won a three-month mentorship program and $150,000. Michael Seibel, managing director of Y Combinator, said of their idea, "I had to take a chance!"

Seibel's skepticism was rooted in America's historical wariness of gambling. Roulette, poker, and other online casino games are largely illegal, and sports betting was only legal in a few states until May 2018. Kalshi as a risk-hedging platform rather than a bookmaker seemed like a good idea, but convincing the CFTC wouldn't be easy. In 2012, the CFTC said trading on politics had no "economic purpose" and was "contrary to the public interest."

Lopes Lara and Mansour cold-called 60 Googled lawyers during their time at Y Combinator. Everyone advised quitting. Mansour recalls the pain. Jeff Bandman, a former CFTC official, helped them navigate the agency and its characters.

When they weren’t busy trying to recruit lawyers, Lopes Lara and Mansour were meeting early-stage investors. Alfred Lin of Sequoia Capital Operations LLC backed Airbnb, DoorDash, and Uber Technologies. Lin told the founders their idea could capitalize on retail trading and challenge how the financial world manages risk. "Come back with regulatory approval," he said.

In the US, even small bets on most events were once illegal. Under the Commodity Exchange Act, the CFTC can stop exchanges from listing contracts relating to "terrorism, assassination, war" and "gaming" if they are "contrary to the public interest," which was often the case.

In 1988, as academic interest in the field grew, the agency allowed the University of Iowa to set up a prediction market for research purposes, as long as it didn't make a profit or advertise and limited bets to $500. PredictIt, the biggest and best-known political betting platform in the US, also got an exemption thanks to an association with Victoria University of Wellington in New Zealand. Today, it's a sprawling marketplace with its own subculture and lingo. PredictIt users call it "Rules Cuck Panther" when they lose on a technicality. Major news outlets cite PredictIt's odds on Discord and the Star Spangled Gamblers podcast.

CFTC limits PredictIt bets to $850. To keep traders happy, PredictIt will often run multiple variations of the same question, listing separate contracts for two dozen Democratic primary candidates, for example. A trader could have more than $10,000 riding on a single outcome. Some of the site's traders are current or former campaign staffers who can answer questions like "How many tweets will Donald Trump post from Nov. 20 to 27?" and "When will Anthony Scaramucci's role as White House communications director end?"

According to PredictIt co-founder John Phillips, politicians help explain the site's accuracy. "Prediction markets work well and are accurate because they attract people with superior information," he said in a 2016 podcast. “In the financial stock market, it’s called inside information.”

Trading on nonpublic information is illegal outside of academia, which presented a dilemma for Lopes Lara and Mansour. Kalshi's forecasts needed to be accurate. Kalshi must eliminate insider trading as a regulated entity. Lopes Lara and Mansour wanted to build a high-stakes PredictIt without the anarchy or blurred legal lines—a "New York Stock Exchange for Events." First, they had to convince regulators event trading was safe.

When Lopes Lara and Mansour approached the CFTC in the spring of 2019, some officials in the Division of Market Oversight were skeptical, according to interviews with people involved in the process. For all Kalshi's talk of revolutionizing finance, this was just a turbocharged version of something that had been rejected before.

The DMO couldn't see the big picture. The staff review was supposed to ensure Kalshi could complete a checklist, "23 Core Principles of a Designated Contract Market," which included keeping good records and having enough money. The five commissioners decide. With Trump as president, three of them were ideologically pro-market.

Lopes Lara, Mansour, and their lawyer Bandman, an ex-CFTC official, answered the DMO's questions while lobbying the commissioners on Zoom about the potential of event markets to mitigate risks and make better decisions. Before each meeting, they would write a script and memorize it word for word.

Several prediction markets that hadn't sought regulatory approval bolstered Kalshi's case. Polymarket let customers bet hundreds of thousands of dollars anonymously using cryptocurrencies, making it hard to track. Augur, which facilitates private wagers between parties using blockchain, couldn't regulate bets and hadn't stopped users from betting on assassinations. Kalshi, by comparison, argued it was doing everything right. (The CFTC fined Polymarket $1.4 million for operating an unlicensed exchange in January 2022. Polymarket says it's now compliant and excited to pioneer smart contract-based financial solutions with regulators.

Kalshi was approved unanimously despite some DMO members' concerns about event contracts' riskiness. "Once they check all the boxes, they're in," says a CFTC insider.

Three months after CFTC approval, Kalshi announced funding from Sequoia, Charles Schwab, and Henry Kravis. Sequoia's Lin, who joined the board, said Tarek, Luana, and team created a new way to invest and engage with the world.

The CFTC hadn't asked what markets the exchange planned to run since. After approval, Lopes Lara and Mansour had the momentum. Kalshi's March list of 30 proposed contracts caused chaos at the DMO. The division handles exchanges that create two or three new markets a year. Kalshi’s business model called for new ones practically every day.

Uncontroversial proposals included weather and GDP questions. Others, on the initial list and later, were concerning. DMO officials feared Covid-19 contracts amounted to gambling on human suffering, which is why war and terrorism markets are banned. (Similar logic doomed ex-admiral John Poindexter's Policy Analysis Market, a Bush-era plan to uncover intelligence by having security analysts bet on Middle East events.) Regulators didn't see how predicting the Grammy winners was different from betting on the Patriots to win the Super Bowl. Who, other than John Legend, would need to hedge the best R&B album winner?

Event contracts raised new questions for the DMO's product review team. Regulators could block gaming contracts that weren't in the public interest under the Commodity Exchange Act, but no one had defined gaming. It was unclear whether the CFTC had a right or an obligation to consider whether a contract was in the public interest. How was it to determine public interest? Another person familiar with the CFTC review says, "It was a mess." The agency didn't comment.

CFTC staff feared some event contracts could be cheated. Kalshi wanted to run a bee-endangerment market. The DMO pushed back, saying it saw two problems symptomatic of the asset class: traders could press government officials for information, and officials could delay adding the insects to the list to cash in.

The idea that traders might manipulate prediction markets wasn't paranoid. In 2013, academics David Rothschild and Rajiv Sethi found that an unidentified party lost $7 million buying Mitt Romney contracts on Intrade, a now-defunct, unlicensed Irish platform, in the runup to the 2012 election. The authors speculated that the trader, whom they dubbed the “Romney Whale,” may have been looking to boost morale and keep donations coming in.

Kalshi said manipulation and insider trading are risks for any market. It built a surveillance system and said it would hire a team to monitor it. "People trade on events all the time—they just use options and other instruments. This brings everything into the open, Mansour says. Kalshi didn't include election contracts, a red line for CFTC Democrats.

Lopes Lara and Mansour were ready to launch kalshi.com that summer, but the DMO blocked them. Product reviewers were frustrated by spending half their time on an exchange that represented a tiny portion of the derivatives market. Lopes Lara and Mansour pressed politically appointed commissioners during the impasse.

Tarbert, the chairman, had moved on, but Kalshi found a new supporter in Republican Brian Quintenz, a crypto-loving former hedge fund manager. He was unmoved by the DMO's concerns, arguing that speculation on Kalshi's proposed events was desirable and the agency had no legal standing to prevent it. He supported a failed bid to allow NFL futures earlier this year. Others on the commission were cautious but supportive. Given the law's ambiguity, they worried they'd be on shaky ground if Kalshi sued if they blocked a contract. Without a permanent chairman, the agency lacked leadership.

To block a contract, DMO staff needed a majority of commissioners' support, which they didn't have in all but a few cases. "We didn't have the votes," a reviewer says, paraphrasing Hamilton. By the second half of 2021, new contract requests were arriving almost daily at the DMO, and the demoralized and overrun division eventually accepted defeat and stopped fighting back. By the end of the year, three senior DMO officials had left the agency, making it easier for Kalshi to list its contracts unimpeded.

Today, Kalshi is growing. 32 employees work in a SoHo office with big windows and exposed brick. Quintenz, who left the CFTC 10 months after Kalshi was approved, is on its board. He joined because he was interested in the market's hedging and risk management opportunities.

Mid-May, the company's website had 75 markets, such as "Will Q4 GDP be negative?" Will NASA land on the moon by 2025? The exchange recently reached 2 million weekly contracts, a jump from where it started but still a small number compared to other futures exchanges. Early adopters are PredictIt and Polymarket fans. Bets on the site are currently capped at $25,000, but Kalshi hopes to increase that to $100,000 and beyond.

With the regulatory drawbridge down, Lopes Lara and Mansour must move quickly. Chicago's CME Group Inc. plans to offer index-linked event contracts. Kalshi will release a smartphone app to attract customers. After that, it hopes to partner with a big brokerage. Sequoia is a major investor in Robinhood Markets Inc. Robinhood users could have access to Kalshi so that after buying GameStop Corp. shares, they'd be prompted to bet on the Oscars or the next Fed commissioner.

Some, like Illinois Democrat Sean Casten, accuse Robinhood and its competitors of gamifying trading to encourage addiction, but Kalshi doesn't seem worried. Mansour says Kalshi's customers can't bet more than they've deposited, making debt difficult. Eventually, he may introduce leveraged bets.

Tension over event contracts recalls another CFTC episode. Brooksley Born proposed regulating the financial derivatives market in 1994. Alan Greenspan and others in the government opposed her, saying it would stifle innovation and push capital overseas. Unrestrained, derivatives grew into a trillion-dollar industry until 2008, when they sparked the financial crisis.

Today, with a midterm election looming, it seems reasonable to ask whether Kalshi plans to get involved. Elections have historically been the biggest draw in prediction markets, with 125 million shares traded on PredictIt for 2020. “We can’t discuss specifics,” Mansour says. “All I can say is, you know, we’re always working on expanding the universe of things that people can trade on.”

Any election contracts would need CFTC approval, which may be difficult with three Democratic commissioners. A Republican president would change the equation.