The Diary Of A CEO with Steven Bartlett: How I Manipulated The World's Richest Men: “They Lost $100 Million In One Night!” - Molly Bloom (Molly's Game)

They put a gun in my mouth, beat the hell out of me,

and he said, if you tell anyone about this,

I know where your family lives.

For the first time in my life,

I knew finally it was game over.

I'm Molly Bloom.

Dubbed the poker princess.

The former waitress who took a small poker game

run out of a dingy nightclub.

To the biggest underground poker game in the world.

For Hollywood celebrities to millionaires.

They literally made a Hollywood movie about it.

The game turned from legal to illegal.

I had become the biggest game runner in New York City.

Leo DiCaprio, Ben Affleck, Toby McGuire.

Politicians who was making $4 to $6 million a year.

It was unbelievable.

$250,000 buy-in.

So I couldn't sit down

unless I brought $250,000 to lose.

That's right.

And you saw someone lose $100 million in a night.

Yes.

This is where the science of how you make people feel

became a really big tool.

And I would memorize people's lives,

the names of their kids, what they cared about,

favorite food order, drink order.

These things can absolutely be used for good,

but I just became obsessed.

What had been about trying to be an entrepreneur

and be gutsy started to be exclusively

about the money and the power.

But I paid a huge price for it.

I started to partner with people

that were not the right people to partner with.

In the middle of the night,

I get arrested by 17 FBI agents, machine guns.

They put me a handcuffs and they put this piece of paper

in front of me that says

the United States of America versus Molly Bloom.

The FBI gives you an ultimatum.

They're gonna give you millions

if you snitch on the players in the game.

I had 48 hours.

What happens then?

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Thank you and enjoy this conversation.

Molly, what do I need to understand

about your earliest context, to understand you?

Going right in.

I think it almost always starts with a family and childhood.

And I am from a family of, you know,

my two little brothers are incredible humans.

And I'm from a family of, you know,

my two little brothers are incredible humans,

but like the craziest overachievers you could ever imagine.

And then I have these two incredible parents

who were very powerful influences in our lives.

My dad stood on this platform of you cultivate discipline

and if you have a fear, you walk through it

and you learn how to suffer constructively

for your dreams, for your goals.

And then my mom, you know, she was this,

she insisted on kindness and integrity.

So there was this whole ecosystem of extraordinary.

And I didn't know how I fit into that at all.

And I desperately wanted a seat at that table.

And probably during the times that we were raised,

there are these ideas of what success looked like

and how you get there.

And it was genius and talent and specific skillset.

You know, but I knew that I had to be successful

or, and this is not hyperbolic,

I literally did not want to live.

I mean, I remember when I was applying to law school,

I said to my dad, if I don't get into an Ivy League

law school, I don't know, like how, I don't want to live.

You know?

And-

Did you mean that?

It's hard to know what you mean at 18 years old,

but in my mind, you need clear proof and evidence

that you are extraordinary by these accomplishments.

And my brothers had already started to make that happen.

And-

Why law?

Why law?

Because one day at the dinner table,

my dad said to me, do you like to argue in a read a lot?

Maybe you should go to law school.

And then I started to kind of read books about the law

and fiction a lot.

I mean, I was, I loved stories.

And then started to think about getting paid

to argue for a living and all the glory

that could come from that if you're fighting for justice

or you're, you know, fighting to save somebody

who's innocent, you know, the sort of high points,

the aspirational points of what it would be like

to be a lawyer in a movie or a book.

You're thinking about the glory?

Yeah.

Yeah.

For sure.

Why do you think you cared so much about glory?

I don't think I cultivated much self-esteem.

I don't think I knew who I was.

And I don't think that I believed I was inherently worthy.

I believed that I had to achieve something

big, huge, extraordinary, worldly

in order to then feel relief from that existential ache

of that followed me around my whole life, you know?

So you go off and try and pursue a career in law,

at least that's what you think you're gonna do.

Yeah.

You're gonna go to Harvard, right?

Well, I wanted to go to Harvard.

I didn't even end up going at all

or even finishing my last semester and a half at school

because I just couldn't muster the energy

and ambition it took to go do all these things.

I just had, I had hit a wall

and I think I was really questioning

the conventionality of it all.

So I ended up like not applying to law schools

and then just saying, I just need a year.

And the closest place that was warm on the ocean

from Colorado in a straight line was California.

When you moved here, your father, again,

bringing him back into the picture,

he's a very ambitious person.

How did he receive this news that you were coming to LA?

Not happy about it, not gonna financially support it.

Really disappointed.

So you get here and he's no longer

supporting you financially at all.

So what'd you do to make money?

I mean, I got a job.

I had to get a job the day I got here

and I went to this restaurant in Beverly Hills,

went to, you know, got a job for a couple of days.

It was terrible.

And then I went to this other restaurant

and kind of lied and said,

cause no one else was hiring in this Beverly Hills area.

And it was a fine dining establishment

and I lied and said that I had fine dining experience.

I got fired a couple of weeks later.

My boss said, you're the worst waitress we've ever seen

and you've ruined like thousands of dollars

of bottles of wine trying to open them.

He said, but, you know, people seem to take to you

and you're a hard worker.

So why don't you come work

for our real estate development company

as my executive assistant.

Oh, so it was the boss of the restaurant

that offered you the job as the executive?

Yes, they had a bunch of holdings.

They had some real estate, they had some restaurants,

they had a fund.

So you became his EA, his PA?

Yeah.

And this led you to poker?

Yes, he came in the office one day and he said,

and there are always zany things

to sort of like thrown at me.

And he said, I need to just serve drinks

at my poker game tomorrow night.

And I, you know, I tell this story cause it's just so

indicative of the naivete and where I was.

I remember googling what kind of music

do poker players like to listen to and what do they eat?

And then I proceeded to make this incredibly embarrassing

playlist with songs like The Gambler on it, you know,

and got this cheese plate and showed up

for this very fancy poker game in Hollywood

with A-list celebrities.

And, you know, there's some names that,

of people that have already talked about being in the games

and those are the names that I don't mind naming

just to give context.

It was Ben Affleck and Toby Maguire and Leo DiCaprio.

And then, you know, but apart from the actors,

it was also the head of some of the biggest investment banks

in the world and the head of some of the biggest movie studios

and politicians who were household names

and people in the tech world that were about

to take their companies public.

I mean, it was unbelievable.

Quite a few people have come out, as you say,

and said that they played in those games.

Yeah.

I was watching a video earlier of like even Dan Bolzarian,

I think says.

Yes, Dan played.

He played in those games.

Were those games legal or illegal?

Because. Legal to play in.

Legal to play in. For sure.

Legal, I, when I started running the games,

I hired defense attorneys and had them analyze

the federal statutes and to help me figure out a way

to do it legally because in the early days,

I wouldn't have done it illegally.

That was an evolution.

So you start as a, basically an assistant to the games

that your boss is running.

These are secret games, right?

Right. Very secretive.

Very.

And take me on the journey of what happens next.

Okay.

So that first game, I'm just shell shocked, essentially.

And also really mortified about the playlist

and the cheese plate from Gelson's, you know?

But man, am I intrigued?

You know, getting to be 23 years old,

getting to be a fly on the wall in this room

where these conversations are open and candid

and you are, I'm like you,

I've always been fascinated in psychology.

I've always been an information data junkie.

I love to learn.

I love to observe.

And so this was as compelling as it could be.

And then I remember at the end of the night

because people were tipping with chips.

It wasn't straight cash.

I remember making $3,000 for refilling some drinks.

And so two things became really apparent to me.

One, this was incredible access to a network of people

that I don't know if I would have ever had access to

and to learn from people at this age of 23

when I didn't know who I was or who I wanted to be.

And number two, that there was something that happened

when there was a token or a chip

was the economic system that made people very liberal.

Because I'd worked as a waitress,

you know, I was waitressing everywhere.

I'd hustle my butt off for a couple hundred dollars a night.

You know, all of a sudden the chip is involved

and it's not real money.

So I just became obsessed.

And so I learned about poker.

I wanted to learn the rules of the game, the vernacular.

I didn't want to seem like a novice.

And then I started to try to figure out

how do I stay in this room?

And this is where one of the places

where effective presence became a really big tool.

What's effective presence?

Effective presence is the science

of how you make people feel.

Everybody has their own emotional footprint

that they leave on the world.

And there are really market things you can do

to have either positive or negative effective presence

or neutral, which is also not great.

So I remember talking to my mom

and I remember saying,

you don't even understand how compelling this is.

And I want to stay in this room more than anything

but I don't know how I could ever confer value in this room.

Did you feel like you were gonna be kicked out of the room?

I just felt like maybe I was disposable.

Like maybe they would just bring in another woman

at some point to serve drinks.

Or, you know, I just didn't want to be disposable.

I wanted to find some reason to be,

to be valuable in that room and to be able to come back.

And I was talking to my mom so much about everything

that I hoped to gain and where my mind was going

with this opportunity.

And I said to her, but mom, I have no idea

how to bring value to this room.

These people have everything.

And she said something that was really profound to me.

She said, maybe instead of thinking about all the things

you wanna get, you could think about what you could give.

And then she reminded me of that quote by Maya Angelou

that everyone loves and loves to quote,

which is people are gonna forget what you said

and what you did, but they're never gonna forget

the way you made them feel.

And I thought about that and it's so true.

And I guess I had this suspicion that these people

with their power and their success and their access

were different from the rest of us.

That they believed that they were worthy, you know?

That they didn't have harbor that secret fear

that they weren't good enough.

And what I found unequivocably is that that wasn't true.

And that many times someone at that level

is even more convinced or needs even more validation.

And so I started to try to understand

how to make people feel important, seen, heard, remembered,

how to establish trust, how to establish authentic connection

because something that I realized

by observing these games is that everybody wanted

something from these people.

That was the nature of the relationship.

And so if I could figure out how to establish

a real connection, you know, there's emotional intelligence,

right, which usually has a focus on the outcome,

how to win friends and influence people.

Effective presence is more about being in the present

with someone focused on the connection, not the outcome.

And this is truly what I focused on

for the first six to seven months

is just creating a real connection with people,

observing them and, you know,

trying to train my mind to focus on

what's unique about this person?

What's truly unique about this person?

And then getting to a point where you're vulnerable

enough to say, God, I'm really fascinated

by this thing that you do, you know,

whether it's at the poker table or in business

or just in life and focusing in on the details

and really getting outside of yourself

and becoming curious and becoming a great listener,

which by the way, you are an insanely great listener.

Oh, thank you.

And I just have found probably like you have

that there is such incredible value in that

and that no matter how much somebody is celebrated

or, you know, has a public following or whatever,

it's so seldom that someone just sits down with them

and listens, just gets in it with them.

So funny, as you were saying that,

I was just thinking about how much

of a competitive advantage listening is.

We think that the competitive advantages had in speaking,

but if I've learned anything from doing this podcast,

it's that to truly understand someone

and then be able to, in this context,

ask them a question, but in the world of business,

to deliver them a solution to their problem,

which is getting a sale, to create the upper hand,

you simply have to listen.

Yes.

And you have to listen for as long as you possibly can.

And this is the great thing about what I've learned

from doing this podcast, but even from this conversation is,

my next question is gonna be so much better

for the fact that I listened to you.

Right, and actively listened.

Actively listened.

Presently listened.

I think we walk around armored with our egos.

And I think that true connection happens

when somebody, when you're able to disarm somebody

and they're able to disarm you

and the egos slip away and it's just two people.

So when you go in and you start listing off

your accomplishments and painting yourself as this,

you know, all of a sudden it's like competition up,

egos up, and then there's not true connection.

You can't penetrate that kind of wall, can you?

You both built two walls between yourselves

because you're showing off.

Right.

You need the walls to come down

to form the connection.

Yeah.

When people hear that, they go, you know,

this idea of effective presence

and understanding how to be kind of a different jigsaw

and shape piece to each individual

to get the best out of them or what you want from them,

people will say, oh, manipulation.

Which, you know, the fine line between sales

and persuasion and negotiation and manipulation,

it's all there, you know.

Is this positive manipulation?

So, effective presence, EQ, active listening,

all of these things that you learn

can absolutely be used for good

or they can be used for bad.

But I think something that is different

about at least the brand of effective presence

that I value is it's about your experience

connecting with a human being.

It's not about, because I used to do that, right?

I used to, the way I used to do things

is I would do all my research on you

and I'd come in here with a few talking points

so that I could instantly connect on something with you

and show you that you and I are the same.

And I don't really do that anymore,

although I don't hate that strategy.

But I think it just depends on how you use it.

I think when you use it in a manipulative way,

I think it's easier to see.

Versus if you kind of take a few breaths

before you go into a room and you say,

this, what I wanna do here is to connect with someone,

to have that human to human feeling

and to be of service in some way

to a greater way to humanity.

And by the way, that can also include yourself.

But I think it's about disconnecting from the outcome,

disconnecting from the transaction

and connecting as a human being.

So how'd you get from being the waitress

in these rooms serving drinks to running your own Poconites?

This is a funny story.

Okay, so a couple of months go by, right?

And I'm like, I don't wanna serve drinks in these rooms.

I wanna start my own games.

I wanna own these rooms.

This was someone who felt powerless in the world.

If I could control these nine seats,

this thing that has so much control over these people

that are so powerful, that was compelling.

The money was compelling.

I had this whole idea of how I would design the experience.

That was compelling.

And also, I'd sort of learned in those six to eight months

that I was an entrepreneur.

I was a problem solver.

I could think on my feet.

I had met a cognition.

I could feel a certain way inside,

terrified, nervous, scared,

and still act with composure.

These things that wouldn't quite present

at a dinner table growing up with Jordan and Jeremy Bloom

to culminate into an idea or sort of like that seat.

All of a sudden, I just started to feel in my flow, you know?

And so, but I was very loyal to my boss.

And he is an interesting character.

He was slightly psychopathic.

So I just bided my time and I tried to figure out

how I was gonna do this.

And then he made it quite simple for me

because he called me and he said,

you're focused too much on the game.

I need you back in the office.

I'm giving the game to someone else.

Her name is da, da, da, da, da, da.

She's gonna be calling you.

And by this point, I had really kind of gotten into,

like I had started to think about

how I was gonna build this game.

I was keeping the books on everyone.

I was recruiting players, you know?

I really had, I was doing much more than just waitressing.

And I thought about it and I was like, I gotta take my shot.

I can't just go.

I can't just let him take this.

Like this is, this opportunity is too important for me.

So I had developed friendships and alliances.

And so I planned a game and I moved it

to a really luxurious location.

And I hired a full staff of people

and had them memorize everyone's favorite food order,

drink order, the names of their kids,

what they cared about in life,

upgraded my playlist, a little Frank Sinatra maybe.

I don't remember what it was, but it was better.

Moved it out of this dungeon basement,

had it catered by the best restaurants in town,

you know, like the best liquors, Cuban cigars.

I mean, I wanted people to walk into this room

and feel like they were in Monaco

or feel like they were James Bond for the night.

And I really, as the games were on,

I really like got into the science of scent science

and temperature and humidity and food

and all these things that elicit the feel good chemicals.

And so, and then I invited everyone except for my boss.

And at the end of the night, the game went really late

and then at five in the morning,

I got this text message from my boss.

And he said, get over here.

To this day, I don't know why I went.

I just went and he made me go wait in this like bedroom

and he made me wait for a long time.

And I said to myself, he's gonna kill me.

I mean, I don't even know what's gonna happen right now

because he was a terrifying individual and very powerful.

And just to give you some context,

when I started working for him,

I used to always say to him,

I'm really worried about your soul.

Like you're not a nice person, you know?

And I saw him in a business context.

And then later when I got to know him,

but I saw him with his family and he was very kind.

But he used to say to me all the time,

you're gonna get trampled over.

Like you need to toughen up.

And so anyway, so he walks into the room

and he has this terrifying look on his face

and he looks at me and he goes, I'm proud of you.

It was like graduation day for better or worse, you know?

It's hard to know how to feel about that moment.

Now sitting here, decades later.

So from that moment when you host that first game,

you upgrade everything,

you upgrade the experience for your customers.

Eventually you set your sights on New York

for a variety of different reasons.

And you move the games from being based in California

and LA to being based in New York City.

I lost the LA game.

You lost it, someone took it from you.

Yes.

Karma.

Yeah, totally.

Not gonna argue with that.

Who took it from you?

One of the most famous movie stars in the game.

Leonardo DiCaprio.

Someone took the games from you, a movie star,

said, I'm gonna go do it at my house.

Gave me an option first.

You can either start making less money.

So this is very interesting.

There is this player in the game.

Who you can't name.

I won't name.

But they're a big male movie star.

Making so much money.

Okay, how much money are we talking?

Like hundreds of millions?

Yeah.

Okay.

But became, I would say pathologically obsessed

with this game and structuring the game

so that he could win all the time.

So making sure that he was the best player in the game

and that there was no one better than he was.

Dan Bolzerian said that he was kicked out of the game

because he was really good.

Oh, well, listen, Dan showed up playing this kind of ruse

that he was just this clueless, trust-fun kid, okay?

And people bought it.

And I said, I sat there watching him

and I'm like, this dude knows what he's doing, you know?

And I said, respect, right?

Like you're hustling, I'm hustling,

but you can't play in this game.

You're gonna take everyone's money.

You're bad for business.

I wish you the best.

So you kicked Dan Bolzerian out of the game.

I had to.

He was too good.

Yeah.

Okay, so he wasn't, he was telling the truth.

Yeah.

And yeah, for sure.

So this Hollywood star that took you,

that stole your game from you.

So he was really obsessed with the game

and he was obsessed with the money that he was making

and being the biggest winner.

And the truth is at the end of the year,

the money that I was making by that point was millions.

And he believed that was money

that should be going into his pocket.

Even though by this point,

I was traveling the world recruiting players.

I had a staff of 20 people.

I handled all the logistics.

I handled credit extension, collections.

I was on the hook if someone didn't pay.

I had a full business.

I was paying my taxes.

There was so much work and sweat equity

and I had branded the game in this incredible way.

And I took notes every single game.

Here are the areas that it works, here it doesn't.

Let me do some deeper research.

And just really turning down cash and cars

and free rolls from the pros

to get a seat to protect the integrity of the game

and paying the debts from my own bank account

so that to make sure people got paid faster.

I mean, I wasn't serving drinks anymore.

And so when he said to me, you're making too much money,

you have the option of making less

and I'll let you keep the game.

Look, by this time, I had become a strategic thinker.

I had really been able to get out

of emotional decision-making,

but I do believe that there's a time and a place

for emotional decision-making.

And so I knew that turning down that offer,

there was a large, the odds where I was gonna lose the game,

but I knew that accepting that offer

meant no autonomy for me, no freedom and no dignity.

And you know-

What was the offer, sorry?

I had to, would have to cap my salary

and make it and have him approve how much I'm making.

What was he bringing to the table

where you can just kick him out?

Was he bringing a lot of-

Celebrity power, yeah.

And celebrity power.

Yeah, in this town?

So he basically said to you,

listen, you're making a lot of money.

I'm bringing a lot to the table

because I'm bringing celebrities and contacts

and legitimacy to this.

So I'll put a cap on your earnings

and I get the rest of what you're making,

but I'll continue to do my part.

Yes.

So he kind of wanted to make you his employee.

Right.

How do you feel about that?

I never want to be anyone's employee ever again.

But how do you feel about him?

Because when you said it, you looked a bit pissed off,

to be honest.

Did I?

A little bit, you looked a bit like

there was still a little bit

of maybe resentment to that moment.

You know, I think that there's just conviction

to that moment.

Right.

Because I think we live in a day and age

where a lot of people try to,

not in a day and age,

it's reality that a lot of people

try to misuse power.

And I think it's really important to talk about,

you know, sort of dignity in the face of that

and turning the offers down.

So you said no, what happens then?

Called me about a week later

and with this almost jubilant laugh and tone,

was like, you're done.

How could he ensure that you were done?

He had colluded with the biggest whale in the game,

a whale in a gambling context,

someone with a lot of money,

he's not very good,

he's willing to lose a lot of money.

And this person had endless funds

and he had colluded with him

to have the game at his house.

And that was where the money was for everyone.

And you asked me a question,

how do I feel about this person?

Here's my answer.

This was a really long time ago.

And I've totally forgiven him.

So you lose the game?

I lose the game.

I was devastated.

What's going through your mind at that moment?

I'm done.

I'm never gonna be able to make this much money again.

I'm never gonna be, I'm gonna have to go join some,

you know, I'm gonna have to go work for someone else.

I'm not gonna be able to be my own boss.

I'm not gonna live in this fascinating,

adventurous underworld where I get to, you know,

pull the strings and move the chess pieces

and I have to go join the real world.

Where I'm not extraordinary.

You know, I'm just telling you what's gone through my mind.

Now, when I say these things, it's like,

it is what it is, but...

So you eventually move to New York?

Yes.

30 years old at this point?

I'm 31 at that point.

Okay. Yeah.

So, you know, I bet my parents said,

this is a great time for you to go back to school.

You've saved all this money.

You've learned all this, you know,

you've gained all this information.

You have this incredible network.

And I said to them, you're absolutely right,

but I have something that I need to prove to myself

at least because the plan was never to run poker games

for the rest of my life.

I don't think that's something that's sustainable.

The lifestyle was not conducive for raising a family.

Late nights, you know, crazy adrenaline.

It was not something that I could imagine myself doing

for the rest of my life.

I knew I needed to walk away at some point.

I knew I needed to parlay it into something

that was less underground, less gray.

But, you know, I have to tell you,

there was something very thrilling about it.

But then I got angry and I had something to prove

and there was just nothing that was gonna stop me.

What made you angry?

Feeling like I had been disposed of so effortlessly.

Something that I, you know, something stolen from me

that I had curated and built and, you know,

he said karma before and there is some truth to that.

But I did everything justly, you know?

I left money on the, my own money on the table

to curate this incredible experience.

I ran the games with ultimate integrity.

You know, I wasn't unkind to anybody.

I just felt it was really unfair.

And so also I was embarrassed.

You know?

So I decided I was gonna build

the biggest poker game in the world.

Like five times, 10 times bigger than the game in LA.

And then I would go away.

I decided after doing some research

that I would do it in New York City

because it seemed like there are a lot of gamblers

on Wall Street.

There were many problems with my plan.

First of all, I didn't really know anyone in New York City.

That sort of like billionaire Wall Street world

is not so easy to penetrate.

Secondly, it was 2008.

So the economy and Wall Street had just been brought

to its knees in the most profound way

since probably the Depression.

And thirdly, there were some pretty scary characters

running games in New York who'd been doing it

for 20 years.

But it's testament to when you're obsessed with something.

When the end, like you'll do anything,

unfettered ambition, you'll do anything to get there.

Things are possible for better or worse.

So I made moves.

I did research and I interviewed poker players.

And I found out who the right people were to talk to.

And I found out what was wrong with the current system.

What was wrong with the current games

and where I could improve on that.

I already knew I could bring the branding

and the experience, which was meaningful.

It truly was meaningful.

But what I found is in these big games,

in these New York games, a lot of the game runners

were kind of running a Ponzi scheme.

If they didn't get paid, they wouldn't pay out.

They're playing in their own games.

Whether they were winning or losing

would dictate the rake of that night.

And the rake is the illegal tax

that most of the game runners were taking.

And so it was a matter of treating people fairly.

It was a matter of being trustworthy and consistent

and having integrity.

And then the biggest thing I could do

to instill that trust and to have integrity

and to eradicate the fear was to become the bank.

I would now, MDB Inc. would now become the bank.

Guarantee the games, pay if there is,

if somebody's stiffed, I would pay.

What does a stiff mean?

Meaning they'd lost money in the game

and then didn't pay the debt.

Okay.

I don't understand that.

Surely to get the chips, they have to pay them up front.

No, when you run a weekly game,

ultimately you establish a credit relationship with someone.

Okay, right.

Because otherwise, like these people

would have to bring $5 million in cash every week.

It's just not reasonable.

It's not feasible.

So tell me about the peak of your New York games then.

So when you're at the peak, what does that look like?

So I started this big game.

It was called...

They're all just called Molly's game.

Okay. Yeah.

So it was a $250,000 buy-in.

And then this was the game

that someone would ultimately end up

losing $100 million in one night in.

Say that again.

Explain all of this to me like I'm a chimpanzee

from that documentary you're talking about

before we start recording.

So when you sit down to play at a poker game,

there are a couple numbers that matter.

What's the buy-in?

My LA game, the buy-in to sit down and get chips

and get a chair was $50,000.

It started out as 10.

I raised it to 50.

The New York game was $250,000.

So I couldn't sit down unless I brought $250,000 to lose.

That's right.

Then the other relevant numbers are what are the blinds?

Meaning what do you have to bet each round to play the game?

Just at the start of the round.

Yeah. And there's a small blind and a big blind

and it just goes around the table.

And so these games played so big,

there was so much action, the blinds were so high

that that initial buy-in would be gone

with some people in the first 20 minutes.

So then they'd have to come to me and say,

I need another $250,000.

And I would have to decide in that moment,

can they pay this?

Are they good for the money?

And so I would have to start to establish this relationship,

this financial relationship with people

based on trust a lot of times.

But there are a couple things that kept me safe.

Number one, to stiff this game

was social reputational suicide.

People would start to say,

oh, they don't have money anymore.

Number two, there wasn't a game like it

where you could play with some of your biggest heroes.

I mean, there was so much business

that got done at these games.

The things that I saw created, it was mind-blowing.

But also-

And you can just go to the police if they stiffed you, right?

No, there's no recourse

unless you're willing to go to muscle.

Mafia.

Yeah, organized crime.

Why couldn't you go to the police?

Because it's not illegal to stiff me or a game.

It's illegal to stiff, you need a gambling license

in order to have those types of privileges.

So you can go to jail in Vegas

for stiffing your gambling debt,

but you can't go to jail for stiffing me.

Okay.

I gave you the money.

It's a loan.

So you saw someone lose $100 million in a night?

Yes.

How did that happen?

Ha ha ha.

The game was playing huge.

They were also playing backgammon.

They were also betting sports.

Obviously, I can't guarantee $100 million.

So I'm out after a certain point.

And that was shortly before I got in trouble,

but that game that I established,

the big game in LA and the big game in New York,

sort of joined together and became a billionaires game.

And people over a year's time would lose a billion dollars.

People were, I mean, there's rumors

that a couple billionaires went broke

playing in that game, fully broke.

And this, here comes to a part of this story

that is, I think, really important.

I started to see something I could not unsee anymore,

which was in the beginning,

I just believed rich people could never lose their money,

knew what they were doing,

and that this was just their form of entertainment.

And what I started to see is that a vast majority

of the players in these games,

particularly the big games were gambling addicts,

totally owned by the addiction of gambling.

And I, at some point, had to decide

whether I was okay with playing my part in that.

And my answer by my actions was clearly yes,

but I paid a huge price for it inside.

And that sort of started to enable me

to make other decisions that were not in line

with my integrity, and that had a directly

inverse proportional effect on how much I liked myself,

how much I, my self-esteem, how much I believed in myself,

the kind of person I started to be,

and what had been up until this point

about trying to be an entrepreneur and be gutsy

and make money and sort of source power,

but do it in a way where I'm retaining who I am

and integrity started to be exclusively about the money

and the power and the status.

And I started other games in the city,

and I didn't care if somebody could afford it or not.

And I was drinking a lot,

and I was taking a lot of pharmaceutical pills,

like Adderall to stay up and Xanax to come down,

and just started to live this life

of very little self-analysis.

You compromised your integrity.

I did, big time.

How?

I'm not, I don't have judgments.

Whether or not, like, you know,

the sports betting just became legal.

Sports betting, so many people in my indictment

got indicted for sports betting.

Now it's legal.

Now if you live in New York, New Jersey,

you can download an app connected to your bank account,

watch a tennis game.

Pretty much everything that happens in that game

is a beddable moment.

You can also do that with a Charles Schwab account.

I harbor no judgment for draft,

whoever the companies are, the CEOs are.

It matters who you are, right?

For me, once I realized that what I was doing

was using all my resources, all my skills,

all my intelligence to push an activity

that was ruining a lot of people's lives,

that was an insult to my integrity.

That was getting out of alignment with who I am

and what I care about in the world.

What were you good at?

So at that peak moment, when you do a skills order

of why you were successful,

what appears on that skills order?

Very good at strategy.

Seeing a problem, coming up with a solution,

setting a goal that has, you know,

most of the time pretty slight odds,

figuring out how to get there.

So I'd become very good at strategy.

I'd become really good with people.

I became so good at it that I became manipulative.

And I was using those skills to manipulate people

for my personal gain period, not a win-win.

And all of these things,

the lifestyle that you've chosen to live

and the way you've chosen to live it,

you speak of the internal conflict this creates.

Right, were you depressed at that point in your life?

How was, if I was a fly on the wall when you were going home,

what would I have seen?

What would I, you know, if I was a fly on the wall

that could feel what you're feeling,

what would I have felt and what would I have seen?

I was very depressed, very disappointed with myself

and completely powerless over these forces.

Money, by this point, drugs.

And when I say drugs, like I wasn't,

I didn't like the inconsistency

and the unreliability of street drugs.

I liked the consistency and formulation of pharmaceuticals.

They allowed me to be productive and not feel myself,

not feel the world.

I was drinking a lot.

Why didn't you wanna feel the world?

What were you escaping from?

Myself, what I was doing.

The way that I was living.

What was it you were so ashamed of

about the way that you were living outside of the games?

I had stopped really communicating,

showing up for my family.

At times didn't treat people that worked for me

as well as I'd like to.

I started to have, you know, New York was a trip.

I had all these beautiful, interesting,

compelling women that worked for me.

And although I always wanted them,

I always wanted to mentor them

and provide them with opportunity.

The truth is is that I made sure they made enough money

so they stayed in that darkness with me.

And I didn't hold myself to the same accountability

that I would hold myself now to in a friendship.

I pay them so much money.

I don't have to show up for their birthday, right?

It was a, I had, even if I didn't act like it,

in my mind, there was a hierarchy.

So I had no authentic relationships or very few.

Those were the reasons.

Were you in a relationship at this point?

So I was in a relationship for most of the LA game

and that ended right around the same time

that my game ended.

And then I went to New York

and had sort of a secret relationship.

One of the big players, little brother

who kind of did my role in the beginning

of handing out chips and everything.

I found to be this deeply fascinating, brilliant,

heart-centered person.

And so we were in the secret relationship

but I didn't want anyone to know

because he didn't measure up to the persona

that I was trying to sell,

which was very hurtful to him.

How did he know?

I told him we can't tell anyone.

Did you tell him why you can't tell anybody?

Said it's bad for business.

Is that what I heard him?

You just saying it was bad for business?

Because if you said that to me

and we're in a relationship, I think,

okay, you don't want to complicate the dynamics.

You don't want some people to know

that someone you're involved with romantically

is also kind of attached to the game, so...

Yeah, I mean, I think in the beginning it made sense, right?

But down the road, I think it became very clear.

I mean, we had conversations about it.

At some point, the mafia show up.

Yeah.

So here's the kind of levels and stages of the train wreck.

So the first thing that happened was

I had just recruited these guys.

They were Russian-American businessmen.

They had the air of being Ivy League.

Seemed so legitimate.

I had people vetted within an inch of their life.

I used to hire the same people

that vet politicians, for instance.

To vet people, I had bank employees on my payroll

to find out people's liquidity.

I mean, it was a whole process.

It's a lot of money and big risk

to bring a stranger into a room with important people.

And their stories checked out,

but there was something in my gut that told me it was off.

And it turns out that they were running

the biggest insurance fraud scheme in New York City history,

and they had alleged ties to the Russian mob.

So then the feds start to pay attention

to this $100 million poker game,

where people can show up with millions of dollars in cash

and get a check, right?

Pretty rife for corruption.

And interesting for them.

The next thing that happened was,

I had a run in with Italian organized crime.

And I guess naively, I thought that,

I knew that gambling was always one of the ways

that organized crime earns.

But I was having the games at the Plaza Hotel

with billionaires and players for the New York Yankees,

and I just believed that there was enough separation.

But by this time, I had become the biggest game runner

in New York City, and they didn't care.

They didn't care who my clients were.

And they were really clear with me,

if you wanna continue to run these games,

you're gonna have to give us a piece.

And we all know we've all seen that movie, right?

And I tried to politely decline their offer

and tried to explain to them in business terms

why that wouldn't work for me.

And I just went on my merry way

and started to avoid their calls.

And they didn't just go away.

And they sent this terrifying guy to my apartment.

And he put a gun in my mouth,

which is something that you just never forget.

And he beat the hell out of me

and took everything that was in my safe,

including photographs,

the couple things I had from my grandmother.

And he said, I think your answer will be different next time.

And if you tell anyone about this,

I know where your family lives in Colorado.

And so a couple of things here.

First of all, if somebody comes into your apartment

in the real world, in real life,

puts a gun in your mouth and steals things from you

and beats you up, cracks your ribs,

you have somewhere to go.

You call the police, you call your family,

call your friends.

It was undeniable now that what I was doing

was so deeply dangerous and underground.

And I was completely alone in it.

I was too afraid to tell anyone.

And so I'm trying to like,

and also now I'm not just putting my own life in danger,

right?

Like I'm in way over my head.

And my family's in danger now.

And I'm just, I mean, it is so heavy and so much.

And for the first time in my life,

I don't have any strategy.

I have no idea what I'm gonna do.

And then I got so lucky.

You know, my only contact with outside world

was food delivery and the New York Times.

And a couple of days later, I got the New York Times

and it said 125 arrested

and the biggest mob related takedown

in New York City history.

And I never heard from them again.

But, you know, disaster is a comment.

And the last thing that happened before

the whole thing blows up was,

you know, for most of my poker running career,

I was running these games legally according to this playbook

that had been written for me by my attorneys.

And one of the biggest ones that differentiated me

from a lot of the games in the city

and LA was that I didn't take a rake.

I didn't take a percentage of each pot.

At the end of the game, you winner's tip.

You know, I'm extending people millions of dollars.

I'm in charge of the nine seats that people are,

a lot of them are pathologically addicted to.

At the end of the night, I got paid a lot of money.

I was making $4 to $6 million a year.

And...

Just from tips.

Yeah.

So where did that $4 to $6 million a year come from?

The winners.

So the winners would play in the game

and if they won, you know, they would tip a percentage.

One to 5% of their wins.

Games were huge.

And I was running multiple games around the city.

Paying my taxes.

I have an event planning company.

But, you know, I was a mess.

And I started to get reckless about who I was letting in

the games and who I was letting play

and my debt sheet started to get bigger

and I started to take a rake.

I started to partner with some people that, you know,

were not necessarily the right people to partner with.

And the feds had thrown a confidential informant

in the games by that point and he tracked that.

And so around the end of that year,

I got a text message from one of my employees

at one of my games and they said,

the FBI is here looking for you.

Don't come here.

And so, you know, I knew finally it was game over.

It was game over.

And you realized that when you got that call

saying the FBI here looking for you.

How do you feel at that moment when you hear,

someone calls me and says the FBI looking for me.

Terrified.

I want my mom and I want my dad

and I want to go back in time.

I'm gonna do any of this.

Don't even know how to process this.

And then a couple of hours later it got even worse.

I got, you know, I went back to my apartment

and the whole time, I mean, it's like you're in a movie

or looking around every corner.

Are they gonna be there to apprehend me?

And I packed a bag and grabbed my dog

and, you know, tried to book a plane ticket

to Denver from JFK.

And my credit card got declined, which was strange.

And then my debit card got declined,

which was really strange.

And I logged into my accounts and the account balance

read negative 9,999,999 dollars in all of my accounts.

Why?

Because the feds had seized every single penny.

And then some.

So what happens then?

Did you manage to get out of New York?

I did.

I managed to get out of New York.

I got home to Colorado.

I'm at my mom's house.

My attorneys are talking to the feds and they said,

basically in this country, you as a person

have the presumption of innocence,

but your property does not.

So someone can't just come get you

unless it was under some of those,

like after 9-11 or whatever.

Let's just keep it simple.

Someone can't just get you, throw you into jail,

say that you're guilty.

You have the right to a trial.

With your money, with your property, it's different.

There's a division of the government called Asset Forfeiture

that can just take it.

And then you have to go into legal proceedings

to try to get it back.

And so basically what that would involve

is me going on record, talking about this game

and telling how I made this money,

which for the most part I'd made it legally,

but the past several months I hadn't

and it would be an admission on record of a crime.

So I couldn't.

I couldn't do that.

And at this point, they said,

we're not interested in her as,

we're not pursuing anything criminally against her.

And if we are, we'll let her know.

So I just went, I just went home.

What do your parents think of you

when you come home at this point?

I don't even know what they think of me.

I think they're extremely worried.

I think that my dad had been writing me

handwritten letters every year,

telling me that what I was doing was going to end badly,

pleading with me to do something different.

So I think my dad was angry.

My mom's just scared.

And I think they're also relieved, right?

Like, they were, you know,

they knew that what I was doing was dangerous.

They knew it was, I was up late at night

running around with large sums of cash.

I mean, they had many sleepless nights.

At some point, the FBI gives you an ultimatum

regarding becoming a snitch.

Oh, okay, so it took two years.

For those two years, I moved in with my mom.

I got sober.

I...

At 35 years old.

No, I'm not 35 yet.

I'm 33.

Got sober,

Trek to Machu Picchu, did some deep soul searching.

Finally got a job, moved back to Los Angeles.

Seven days later.

This is two years later, okay?

I don't think anything's coming.

I've rehabilitated myself, you know?

And I've been living with my mom and my grandma

in the mountains of Colorado.

So I moved back to LA.

Seven days later, in the middle of the night,

I get arrested by 17 FBI agents,

machine guns, high beam flashlights.

They put me a handcuffs and they put this piece of paper

in front of me that says the United States of America

versus Molly Bloom.

I'm thrown into this wild indictment.

I'm looking at real time in prison.

How much?

The press really said 90 years.

I think realistically, it was more like 10.

But I have a day and a half to get to New York City

to find an attorney that's gonna represent me

in the fight of my life and I don't have a dollar.

My dad and I aren't speaking.

Why?

Because he got mad at me and I got mad at him.

Because the age-old unexplored resentments

and rife, you know, came to a head.

This is my biggest fear, right?

Failing this spectacularly.

In front of the world, the tabloids are covering it.

So I had a day and a half to get to New York City

to find an attorney and, you know, I don't have a dollar.

My mom just put her house up, it's bail me out of jail.

My dad and I aren't speaking.

So my best friend, you know, loaned me a little money

but I'm sitting down with people

who are quoting $3 to $6 million and $250 to even look at it.

And so I have like eight meetings that day

before the indictment or before the arraignment

and seven out of the eight all said,

you know, Maya, I really wish you the best

but without a retainer, I can't do it.

And then I met Jim Walden who was at a very prestigious law firm

and kind of like listened to my story, looked at my mom

and said, I'm going to help you.

And Jim and I started working together

and I'll never forget something he said to me.

You know, I went in and I said,

look, I don't have the money to fight this, so

but I can't do 10 years, you know,

and I have to have a life after this.

So what is our strategy and what is our angle?

And he said, you know what?

Integrity is going to be our strategy and our angle.

I'm just sitting across from Jim Walden

who is nothing but integrity.

Who is this attorney who has spent his life

fighting the good fight, who continues to fight the good fight,

who spent the first part of his career

in the Eastern District of New York,

fearlessly going into the future.

In the Eastern District of New York,

fearlessly going after the five crime families

who's looking at my indictment

and saying this is bullshit, right?

And taking on this case and fighting for me

because no one else would.

And he's talking about integrity

and I just had this moment of like,

it all hit me, you know?

Who I wanted to be, how far I had come from that

and for what?

And I made a decision in that room that day

that I could never ever abandon myself again in that way.

I could never abandon the things that I knew

to be true to who I am.

And one of those is integrity

and doing what I believe to be the right thing.

And a couple of weeks later,

the prosecutors wanted a meeting

and they really wanted me to be a confidential informant.

Snitched.

Yeah, and Jim believes this is the whole reason

that they brought the indictment.

So that you would snitch on the players in the game.

Yeah, and they didn't care about the mobsters

or the people running the insurance fraud scheme.

I think they already had what they needed on those.

They cared about inside information

that I could potentially provide them with

on the billionaires, the bankers, the celebrities,

the politicians.

And you spend enough time with people,

you do get that inside information.

Now, I wanna be really clear about something.

If there was someone in my game

that was doing really bad,

like if Epstein was in my game

and I knew that he was trafficking children or whatever,

like I would have given that information freely

and before this.

But what I knew.

Was Epstein in your games?

No, no, I'm saying if there was a character like him.

Right?

I would have never protected someone like him.

But the things that they were interested in,

to me, who's booking sports,

it's about to become legal in two years

in New York and New Jersey.

You're gonna drag somebody's family through the mud

and I'm gonna be, you're accomplice with that.

Did they offer to restore your bank accounts if you snitched?

They offered to give me all my money back.

Which was how much money?

Millions.

So they were gonna give you millions if you snitched.

Yeah.

And also, they were gonna give me a deferred prosecution

which would have kept,

sort of given me a guarantee that I would stay out of jail.

And I went home and I,

I had a very short amount of time to make this choice,

something like 48 hours.

And here's where I got to with it.

This place that I was in was 100% my fault.

I did all of this.

I had near perfect information about the law.

I had great parents.

I had college education almost completed.

I had all the opportunities in the world.

And I had chosen this and I had chosen this path.

And I had to own that, you know?

And turning around and ruining the lives of people

who had played in my game who'd made me very wealthy.

Many of them, I saw their kids grow up

to get out of the trouble of my own choices,

did not feel in alignment with my true self.

So you ultimately get sentenced?

I get sentenced.

I get a judge that's very disappointed with me.

And, but ultimately a pretty reasonable guy who said,

listen, you were running poker games

and it seems like you've done a lot to change your life.

I'm not gonna sentence you to prison.

Which it's hard to adequately express to you

how big that moment is.

Because you can do all, you know,

I used to say to Jim all the time,

whatever, I'll go to a federal prison,

I'll learn a new language, I'll mentor some women.

And he's like, that's not what it's like

in the prison system, you know?

People are dangerous and a lot of the guards are dangerous

and women get raped, it's not a country club.

And in my mind, I was just like,

I can handle it, I can handle it, I can handle it.

But in that moment, when you get sentenced

to not go to prison and you're not gonna lose your freedom,

you don't realize how big it is until that happens.

And probably would have been even bigger

from what the other way.

But I mean, I felt like, I lost my feet, you know?

And, oh man, you know, here we are going to dinner

after the sentencing and there's my best friend, Ali,

who stuck with me through everything and my family

and even my old boss came

and I'm looking around the table

and everyone's living their lives, having kids.

My brother's a heart surgeon, he's in residency.

He just graduated Harvard.

My other brother just got inducted

to the Colorado Sports Hall of Fame

and I'm just sitting there and I'm like,

here I am, the family felon, you know, I'm 30,

now I'm 35 years old, millions of dollars in debt,

a convicted felon, a social pariah to some degree.

Like, I'm all in for a comeback,

but how does that even happen?

Where do you go from here?

So I just remember going back and walking the mountains,

you know, going back, moving in with my mom,

walking the mountains, walking, meditating,

trying to figure out what is the way out here.

You know, one of the things I always talk to my friends

about is as you become more and more successful,

you get to see behind other curtains.

I call it, you know, it's like a-

Totally.

Yeah, like it's a curtain you didn't even know was there

and you meet this other group of people

and you find out that they're making money

in this other set of ways.

And you go, what the fuck?

You guys have been back here doing this stuff all the time.

So I can, that's so real, isn't it?

All these money games that I didn't even know existed.

Like, you do this and you trade this

and you do this and you flip this.

And you go, what the fuck?

I was like, I was earning like minimum wage over here.

And you billionaires around here,

just like doing billion dollar things

with these little games that I didn't even know existed.

And that's what I've come to learn in my life.

It's like, I got to see behind a lot of curtains

and I was like, oh, fuck, I can do,

I can earn this much money without doing any work

or you can do it like this.

And what are those things that you came to learn about

when you got to see behind the curtain?

Couple things.

First of all, I thought behind that curtain,

I was going to find the most contented, generous,

non petty, like extraordinary people.

And that's not what I saw for the most part.

There were exceptions.

I just saw people who were kind of like unwilling to fail.

Because...

I don't know, because they're obsessed with money.

I mean, it was just drive a lot of times.

Or being dragged.

Or being dragged, right.

Was it more being dragged than drive?

Or was it more drive than dragged?

I could they stop if they wanted,

were they in control of their obsessions?

Dragged.

In those settings.

It's what I've tend to find.

I've met a lot of billionaires and I,

with the odd exception, I'm like, damn unhappy.

But I can't stop.

Yeah.

Have you ever read that book, The Psychology of Money?

Yeah.

Don't you love that story in there?

I love it.

I don't know what story in particular you're talking about.

Remember when Joseph Heller is at the house of the billionaire

and someone walks up and says,

Heller, like this guy just made in one day

what your gross sales were for Catch-22 or whatever.

And Heller just goes, yeah,

but I have something he'll never have.

He goes, what could that possibly be?

Enough.

Boom.

That's peace.

Most of these people that I knew do not have peace

and peace should not be underrated.

Peace, contentment, the ability to find joy

in small moments.

And then have the big moments.

I am all for adrenaline.

I still chase it.

I have to chase it less, not that I'm a mom.

But I chase it in healthier ways, you know?

Helly skiing, whatever it is, climbing mountains.

But to sit, lay your head down at the end of the day

and be able to say, I know who I am.

And there may be times where I lose sight of that,

but I have a process for that.

And, you know, I've made these living amends

to these people I love so much.

What else did you see behind that curtain?

So you saw a lot of dissatisfaction with life?

Yeah.

I saw a much bigger world than I knew existed

and a much more malleable world.

That's super key, that malleable point.

Yeah, I thought like the walls were a lot more solid.

In life, generally?

Yeah.

But you realize success is something

that we can all bend, control, manipulate?

I think all is a pretty powerful word.

I think if we are willing to do the work that it entails

on ourselves, yes, I think success, money, abundance

is much more available than I originally thought.

Is that because you see very ordinary people

achieving very extraordinary results?

And then once you see how they're doing it,

you go, ah, okay.

Yes, precisely.

That's also what I feel.

Yeah, that's cool.

I haven't thought about that and that's really cool.

I like that.

And this next, the way that my story ends

really kind of speaks to that.

Or not ends, but begins again.

So I'm walking around the mountains,

I'm thinking to myself like, what's the way out?

And I just realized there's a unique story here.

We've seen this version of a story,

it just usually has a male star, right?

Like the Wolf of Wall Street or something.

Right, right, right, right.

And so I'm like, I'll write this book

and it'll sell so well and my life will change, you know?

And I went to New York Publishing

and there was a lot of publishers

that wanted to give me a lot of money

for a celebrity takedown book.

And I wasn't willing to do that, so I get rejected a lot,

but I just kept, you know, I was just persistent

and I got this book deal.

I got my own press and everything

and I waited for this, you know, I released the book

and I waited for my life to change

and I think like 100 people read the book or something.

Really?

Maybe a little more than a hundred,

but not enough to even earn back my advance,

which wasn't that big.

And then I said to myself, I still believe in this story.

I still believe that the story is the way out.

I just believe it, I can see it.

I'm gonna have to bring in the big guns.

And I said to myself, I need to get,

I need to go speak to one

of the most powerful filmmakers in Hollywood.

I had a bunch of meetings and I was like,

it can't be something small.

It has to be something big.

And so I made this short list of people who really come,

who really are successful, who are the A-list here,

you know, and it was like Shonda Rhimes, Steven Spielberg,

you know, Aaron Sorkin,

and there was another component that this person had to have,

another feature to their personality.

They had to be fearless

because there were so many people, as you can imagine,

in the political world, in Hollywood,

in, you know, the billionaires making calls saying like,

don't make this Molly Bloom movie

because they don't wanna take the risk at all,

even though I'm, you know, I went to bat for them,

they don't wanna take the risk at all

that they could be portrayed in this movie.

Anyway, so, you know, I loved the West Wing

and I loved social network and I loved the characters

that, and the sort of like message and humanity

that comes out from his writing.

So I was like, I need a meeting with him,

Aaron Sorkin, and he happens to also be

the highest-paid screenwriter in Hollywood.

So he's a good bet, right?

That number doesn't come from Fit in Air.

So most people laughed me out of their office.

They're like, your book sold 10 copies, you know?

Like this, it was in the press a couple years ago.

Aaron Sorkin's never gonna look at this.

And I just kept with it.

I was just persistent because I had seen, you know?

As you'd seen.

I'd seen how people get successful.

Persistence.

Of course you have to have a good product.

Of course you had to have a good story.

I believed in the story.

But I got rejected so many times, you know?

So finally I get this meeting with Aaron.

And I remember trying to mentally prepare for it.

Living with my mom, you know?

I'm by all societal measures, the classic loser.

Like I'm like living in my mom's basement.

I have no money.

I don't have any of the trappings of the world

and the success world, you know?

But I said to myself, you walk in there

with humility of lessons learned,

but you walk in there like you're worthwhile, you know?

Isn't there some famous quote that he said

about how you were the most confident

down and out person he'd ever met?

Oh yeah.

So when I was done telling him my story,

he said, well, I'll tell you one thing.

I've never met someone so down on their luck

and so full of themselves.

So down on their luck and so full of themselves?

I certainly was not full of myself, but.

That's what you were giving.

I was giving.

And yeah, I mean, the TLDR of that is he takes it on.

He drops what he's doing.

He takes it on.

He decides to make it his directorial debut

as well as writing it.

The movie comes out.

It's nominated for every award,

BAFTAs, Oscars, Golden Globes.

Also, I had done a lot of really good negotiating

on my part, on the money part.

They wanted to give me nothing upfront

and promised me back end.

And I had done enough research to know

that that wasn't ever gonna happen.

The back end in Hollywood is notoriously.

When you say you did well, what do you mean?

Give me something.

So how can I gauge that?

So I can just tell you that I got 15 times

what someone normally would have gotten in my position.

And your position was?

A book that didn't really sell.

You were the owner of the IP, I guess.

Yeah, Life Rights, a life rights deal.

Like if that book had become a best seller

and it already had a built-in audience

and I had a million followers on Instagram

and there was this compelling package.

Sure.

So how well did that movie do?

It did extremely well.

I mean, 50 million people saw it.

Do you have an idea of numbers of value?

Do they give you a value?

Because I know they say opening box office was X.

Like lifetime value?

Yeah.

They don't because you have a back end.

They give you a sort of convoluted back end number.

But everyone made money on the movie

and it got nominated for awards

and I'll never forget getting the bank wire again.

And it takes a really long time.

You don't just get paid upfront.

You get like 50 grand and then you get the rest of it

three years later, four years later,

whenever the movie gets made.

And it was a rocky road to make the movie

because it was all set up at Sony.

Everything was going smoothly.

It had this big budget, like big movie studio budget.

And then Kim Jong-un got pissed about the interview.

Remember the Seth Rogen movie?

Oh yeah, yeah.

And he hacked Sony Studios

and the chairwoman was Amy Pascal

and she was the one that really believed in the movie

and she had to step down

and then the new chair person wasn't that passionate.

And so then we had to set it up kind of like at festivals.

So, you know, nothing's ever a smooth ride.

So you get a big check from this movie?

I do.

But I'm still, I still owe millions.

Not today sitting here, but at that point.

So I had to figure out like, what is, what's the next move?

And I remember the first time, I didn't even think about speaking.

You know, like a speaking career or anything.

I just remember the first time I got hired

to speak, it was in front of thousands of people for Google.

And I had never spoken publicly.

And I think I just got on that stage and just blacked out.

Like it was so awful and I was so bad at it.

But the money was compelling.

The adventure was compelling.

And so, you know, it allows me now to make a really great income

and then also work on the other things I'm working on,

which is a podcast in a community called

The Smart Girls Guide to Everything.

It's basically using the strategy, the access,

the network, the resources that I've been able to accumulate

in my life and applying it to real life.

And then I'm writing a book on effective presence.

And I have a one and a half year old at home.

Which wasn't a straight ride, right?

No.

You, I read that you had IVF nine times.

Nine times.

People don't understand the pain of having IVF even once

and then it not going to plan to have it nine times.

Yeah, it's the mental anguish.

You know, it was interesting for me because,

and I think this is important to talk about.

And I'm glad you brought this up.

So I froze my eggs at 36.

And I was told, you're going to be good.

You have a lot of eggs.

You're young, you know, whatever.

And my point is here is I think it's a big money making industry.

And I think they oversell the technology.

And it's not to say don't do it, but to do your own research.

In my case, what I realized is doing three rounds of an egg freezing

procedure would have probably given me a much better shot.

The technology is getting better, but eggs are 80% water.

So freezing and thawing is kind of tricky.

Anyway, so I thought I had purchased this insurance policy on my fertility.

And then when I met Fiona's dad, I was 41 and I said, okay, great,

let's thaw out these magical eggs and none of them worked.

And I was 41 and my fertility metrics, basically the doctor said,

I'll give you a 4% chance of making this happen.

And nine rounds later, it worked.

And I'm so happy I didn't miss it.

But that was a special moment.

Oh, also terrifying, terrifying moment.

The most vulnerable you'll ever be in your entire life.

Up until the point that Fiona was born, I thought to myself, I believed,

I went through life believing, particularly after everything that I had

just been through, there's nothing I can't handle.

And then you have a baby and you realize losing this, this little life

is something that I don't think I can handle.

And of course, there are people that do and they do it with grace,

but you just know in that moment that there is something that would,

that has changed in you that will never be the same.

Terrifying.

Ladies and gentlemen, I'm interrupting this broadcast with a very special

announcement.

Two years ago, I started writing a book based on everything I've learned

from doing this podcast and meeting all of the incredible people that I've

had the privilege of meeting, but also from my career in business,

from running my marketing businesses, my software business, my investment fund

and everything else that I've been doing in business and life.

And from this, I've created a brand new book called The Diary of a CEO,

The 33 Laws for Business and Life.

If you want to build something great or become great yourself,

like the guests that I've sat here and interviewed, I ask you, please,

please, please read these 33 laws.

The book I always should have written.

If you like this podcast, this book is for you.

And it is available now in the description of this podcast below.

And every single day until it's out later this month,

one person that pre-orders it, that takes a picture of their pre-order,

uploads it to their story on Instagram or social media and tags me,

will win a gold version of this book signed by me.

And there's only 33 copies of those available.

So pre-order it now, tag me on social media when you do.

And 33 of you are going to win a very, very special book.

Fiona comes to you when she's 18 years old.

She says, mom, I would like to be a success.

What advice have you got for me, mom?

What'd you say to Fiona?

Well, we're going to be having this conversation well before she's 18.

I want to help her cultivate her passions, her talents.

I want to teach her about her mind in the ways that I've had to learn,

how to manage that mind, how to manage fear, how to manage the internal critic.

I want to teach her to sit with heart emotions, not to run from them,

to figure out what they can teach us.

I want to teach her to go into the shadows, the parts of ourselves

that we don't want to look at and look at it.

Don't wait until you get beat up by the mob, federally indicted,

addicted to drugs and alcohol to finally go into those shadows

to look at the demons that you haven't dealt with.

All these things that I learned through the trials and tribulations of my life,

I want to teach her at a young age.

I want to teach her that her worth is not dictated

by the things that she produced, but she is inherently worthy

at the same time.

She will not be happy unless she has purpose in life.

I believe that to be true.

I don't know who said it, but it was very succinctly said to love and to work.

I believe that people need a reason to get up in the morning,

to go into the world and feel purpose.

I don't care if that purpose is stay-at-home mom or president of the United States.

Will you teach her anything that you learn specifically from being in those rooms

with the billionaire's athletes, politicians?

Absolutely. I'll teach her about risk.

What will you teach her about risk?

You know, I've seen thousands of hands of winning and losing poker

and I've kept Excel spreadsheets on people for years.

And I've then watched the choices they make

and how they get to the numbers that I look at the end of the year.

Is it in their business choices or?

The choices they're making in the game and then in their greater life.

A lot of times when people lose, they become

unwilling to take another big risk.

And if you aren't willing to take risks in life,

over time you will lose the game.

The people that took calculated risks over time won.

People that took impulsive risks didn't.

But people that took calculated risks over time and didn't let a past failure

or an external condition stand in that way won the game.

I think a healthy relationship with risk is super important.

I think being able to stay composed when there's chaos inside, chaos outside

is incredibly important in those rooms.

I think being able to know when to use your emotional mind to make choices

and know when to use your rational mind

and being able to toggle between the two in an intentional and smart way is super important.

And I think ego and greed is the reason that I've seen so many lives come undone,

including my own.

The person that sits before me today,

you know, been on a journey to say the least,

lived many, many lives in many different chapters.

What are you most proud of about yourself now?

When you reflect on the person you are versus the person you were,

what are some of the things you're most proud of about yourself?

I'm proud that when I stay self-aware and when I believe that I'm wrong or believe that I'm

behaving in a way that is not aligned with who and what I want to be in the world,

that I'm willing to either say sorry or do that work really deeply, relentlessly,

do that work to change.

I'm willing that, I mean, I'm proud that I just continued to,

I'm proud that I stayed open.

Is there anything you're not proud of?

From my past or in the present?

In the present.

Yeah, I mean, there are little things that I'm working on,

but I wouldn't say that I'm not proud of them because I think having grace for yourself and

learning how to forgive yourself and treat yourself with compassion is something that I

had to learn as a survival skill back in those dark days, but something that I continue to practice.

The only times that I'm not proud of myself are if I'm staring straight into something that I know,

that I'm totally ignoring that's causing harm in the world to myself, to other people.

Molly, we have a closing tradition on this podcast where the last guest leaves a question

for the next guest, not knowing who they're going to leave the question for.

And the question left for you is what is the message you needed to hear when you were younger

that you didn't hear?

And who was the best person to say it that didn't say it?

Um, okay, that's a great question and a hard question.

And I think the answer is stop searching for the evidence that you were worthwhile,

that you're good enough and just start to believe it.

And I think the person to say it to me is me.

I think I was my own worst critic.

You know, we all have certain challenges in our life, but I think at some point,

taking responsibility for your own shit is the most important thing a human being can do.

Are you there now, like are you at the point now where you know

your self-worth isn't going to come from glory?

Not a hundred percent, but I'm like 90.

Do you think do you think we ever overcome these desires to see, you know, these things?

Because they feel to be so hard-wired in us, especially if they come at a formative age from

people that are important to us, like our parents or the context we're raised in.

It's almost like an oven.

It's like, if you think about anything that you bake, you can't unbake the thing.

You can't unbake a cake.

There's lots of things you can like, you know, separate using various chemical processes.

Yeah. I think maybe if you're willing to go live a monastic life and just meditate all day and

like not live in the real world, even then, I know that for me, anytime I think I have

something completely figured out, something fixed, something else will happen in life

and it'll crop up.

So that's why I think it's so important to have a process for how you deal with these things.

And I think anybody that says, I did this work on myself and now I'm fine,

isn't being fully truthful.

I agree. I completely agree.

And I think that's the most honest answer to give, and I also think it's the true answer.

It's the answer that all the psychologists and psychiatrists that I sit here with tell me as

well. It's the answer I've seen in my life, that it's more about management than it is about taking

our traumas or our hardwiring to zero, which, and I think that's important to say because people

that are struggling with the same recurring patterns in their life hear that and go, thank God,

it's not just me, you know, because they'll beat themselves up when the therapy doesn't work or

the podcast they listen to doesn't change them.

Right. Or like when staring at the sun and sitting in an ice cube bath doesn't fix their like...

They're still toxic after their ass bath.

They want to refund. Molly, thank you so much.

Thank you so much.

Thank you for your wisdom, your honesty. You don't have to be so honest.

And in particular, the amount of life lessons you've been able to draw from this experience,

I think is of tremendous value. So it's no surprise you're a speaker.

I'd bet extensively on your podcast being a huge success as well.

And I'm really excited about this book because I really do think that effective presence is clearly

one of your absolute, you know, dominant skills, just from meeting you today as well.

When the minute you said that explained it, I was like, oh yeah, I get it.

So, and that's an unbelievably powerful skill because all we face in this world is other people.

And so knowing how to get the best from those people and whatever context that might be is

ultimately the superpower that anyone could possess.

It's funny, every year around this time of year, for whatever reason,

I go on a little bit of a psychological shift and that psychological shift, I think,

is somewhat inspired by summer.

But it's also inspired by the fact that I want to feel strong in this season of life.

And as I age, strength training is my number one form of training.

And the question becomes, how do you build muscle and how do you become strong in terms of supplementation?

And this is where Huul's nutritionally complete protein product is my best friend.

For a couple of reasons.

One, it tastes better than any protein product I've ever tried.

Two, in terms of the nutritionally complete aspect, it has the vitamins and minerals you need.

It's about 100 calories.

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Try the salted caramel flavour.

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you

Machine-generated transcript that may contain inaccuracies.