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 games

in the world.

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.

Leonardo DiCaprio, Ben Affleck, and

Tobey Maguire, politicians. She was

making four to six million dollars 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

dollars 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 in 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

were going to give you millions if you

snitched on the players in the game.

I had 48 hours.

What happens then?

Before this episode starts, I have a

small favor to ask from you. Two months

ago, 74% of people that watch this

channel didn't subscribe. We're now down

to 69%. My goal is 50%.

So, if you've ever liked any of the

videos we've posted, if you like this

channel, can you do me a quick favor and

hit the subscribe button? It helps this

channel more than you know, and the

bigger the channel gets, as you've seen,

the bigger the guests get. Thank you,

and enjoy this episode.

Oli,

what do I need to understand about your

earliest context to understand you?

Going right in.

Um

I think

it almost always starts with the family

uh in childhood and

I am from uh a family of you know, my

two little brothers are incredible

humans, but like the craziest

overachievers you can 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's 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 skill

set.

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

Do you Do you mean that?

I

It's hard to know what you mean at 18

years old,

but

in my mind,

you

clear proof and evidence that you're

extraordinary by these accomplishment

accomplishments. And my brothers had

already started to make that happen.

And

Why law?

Mhm?

Why law?

Because one day at the dinner table,

my dad said to me,

"Do you like to argue and read a lot?

Maybe you should go to law school."

And then I And then I started to kind of

read books about the law and fiction a

lot. I I mean, I was I loved stories.

Um and 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 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

to then

feel

relief from that existential ache of

that I that that followed me around my

whole life, you know.

So, you

you go off and try and pursue a a career

in law, at least that's what you think

you're going to do.

Yeah.

You're going to 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

I couldn't muster the the energy and

ambition it took to go

do all these things. I 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, um your father

again bringing him back into the

picture, he's a very ambitious person.

How did he receive this news that you

were

Not

coming to LA?

Not happy about it. Not going to

financially support it.

Really disappointed.

So, you get here and he's he's no longer

supporting you financially at all.

Mhm.

So, what do 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 a

you know, got a job for a couple days.

It was terrible.

And then I went to this other rest I'm I

went to this other restaurant and kind

of lied and said, cuz 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 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 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

Yes.

offered you the job as the exec

Yes, they 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 they're always zany things

to it sort of like thrown at me.

And he said, um

I need you to serve drinks at my poker

game tomorrow night.

And I, you know, I tell this story cuz

it's just

so indicative of of the naivete and

where I was. I I do remember

Googling what kind of music do pick

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

uh

poker game in in Hollywood with

A-list

celebrities. And you know, there's some

names that

of people that have already talked about

being in the game and those are the

names that

I don't mind

naming just to give context. It was Ben

Affleck and Tobey 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

it was unbelievable.

Quite a few people have come out as you

say and said that they were

they played in those games.

Yeah.

I I was watching a video earlier of like

even Dan Bilzerian I think says

Yes, Dan played.

He played in those games.

Was was Were those games that legal or

illegal?

Cuz

Legal to play in?

Legal to play in?

For sure.

Legal

I

What when I started running the games

I hired

uh

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

you know, I'm

just shell-shocked essentially.

And also really mortified about the

playlist and the cheese plate

from Gelson's, you know.

Um

but

but man am I intrigued.

You know, getting to be a at 23 years

old getting to be a fly on the wall

in this room

where the

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 was the

economic system that made people very

liberal.

Cuz I'd worked as a wait, you know, I

was a I was a 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.

Um

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 um there are

really marked things you can do

to have either positive or negative

effective presence or neutral, which is

also not great.

Um

so,

I remember talking to my mom.

And I remember saying,

"You don't even understand how

compelling this is."

And

I don't 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 going to be

kicked out of the room?

I just felt like maybe I was disposable.

Like maybe they would just bring in an

another

woman at some point to serve drinks.

Or you know, I just I didn't

I just didn't want to be disposable.

I wanted to find some reason

to be

to be valuable in that room to, you

know, and and to be able to come back.

And I start I was talking to my mom so

much about everything that I hoped to

gain and and

where my mind was going with this

opportunity.

And you know, that I said to her, "But

Mom, I 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, um

"You know, maybe instead of thinking

about all the things you want to 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

going to forget what you said and what

you did, but they're never going to

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

unequivocally 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 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,

focus on the connection, not the

outcome.

And

this is truly what I focused on um for

the first 6 to 7 months

is just

creating a real connection with people.

Observing them and 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 and focusing in on

the details and and really

getting outside of yourself and becoming

curious and becoming a great listener,

which by the way, you are an insanely

great listener.

Well, thank you.

Um, 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 um, you know,

has

has a a public following or whatever,

it's so seldom that someone just sits

down with them and listens. Just gets in

it with them.

Tiffany, as you were saying that, I was

just thinking about how much of a

competitive advantage listening is. We

think that the competitive advantage is

had in speaking.

Mhm.

But I've 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.

Yes.

And this is what what the great thing of

what I've learned from doing this

podcast, but

even from this conversation is I'm I'm

My next question is going to 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 ego's up and and then

there's not true connection.

You can't penetrate

No.

that kind of wall can't you? Both built

two walls between yourselves cuz 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 this idea of effective presence and

understanding how to be kind of a

different jigsaw shape piece to each

individual to get the best out of them

or what you want from them.

People will say oh manipulation.

Mhm.

Which you know the 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 for me cuz I used to do

that right? I used to if

the the way I used to do things is I

would do all my research on you and I'd

come in here with a with a few talking

points so that I could instantly connect

on something with you and show you that

you and I are are the same.

And I

I don't really do that anymore although

I don't hate that strategy.

Um

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

my what I want to do here is to connect

with someone,

to have that human-to-human feeling,

and you know, to

to be of service in some way to a uh

in a greater way to humanity. And by the

way, that can also include yourself.

You know?

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 poker nights?

This is a funny story.

Okay, so

couple months go by, right?

And I'm like,

I don't want to serve drinks in these

rooms.

I want to I want to start my own games.

I want to own these rooms.

You know, this was

someone who felt powerless in the world.

If I could control these nine seats,

you know, 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.

Um and also,

you know, I'd sort of learned in those 6

to 8 months that that I was an

entrepreneur. I was a problem solver. I

could I could think on my feet. I had

metacognition. 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 uh you

know, 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.

Uh

so I I you know, I just bided my time

and I tried to figure out how I was

going to do this and 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. She's going to

be calling you."

And by this point, I had really kind of

gotten into like I had started to think

about how I was going to build this

game. I had I was keeping

um the books on everyone. I was

uh recruiting players. I you know, I I

really had I was doing much more than

just waitressing.

And

I thought about it and I was like, I got

to 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,

uh

the names of their kids, what they cared

about in life,

upgraded my playlist, do a little Frank

Sinatra maybe. I don't remember what it

was, but it was better.

Moved out of this dingy basement, had it

catered by, you know, the the best

restaurants in town. Up up you know,

like

the best liquors, Cuban cigars. I mean,

I

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 I really as the games were on I I

really like

got into the science of scent science

and temperature and humidity and um

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

it the game went really late and then at

5:00 in the morning I got this text

message

from my boss and he said, "Get over

here."

Uh 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 I I thought I said to myself, "He's

going to kill me." I mean, I don't even

know what's going to happen right now.

Cuz he was a

was a terrifying

individual.

And a 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 and I saw him in a business context.

And then later when I got to know him

better I saw him with his family and he

was very kind.

But he used to say to me all the time,

"You you're going to

you're going to 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.

Mhm.

Um eventually

you set your sights on New York but for

a variety of different reasons, and you

moved 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.

Hm, karma.

Yeah,

totally.

Not going to argue with that.

Who who took it from you?

Uh, one of the most famous movie stars

in the game.

Leonardo DiCaprio?

No.

Uh, someone took the games from you, a

movie star said, "I'm going to go do it

at my house."

Give me an option first.

Um,

you can either

start making less money.

So, this is very interesting.

There was this player in the game

who you can't name.

I I won't name.

Mhm.

But they're big male movie star.

Making so much money.

Okay. How much money we talking, like

hundreds of millions?

Yeah.

Okay.

But became

I would say logically obsessed with this

game and structuring the game so that he

could win all the time.

So, make sure that he was the best

player in the game and that there were

no other uh, there was no one better

than he was.

Dan Bilzerian said that he was kicked

out of the game because he was really

good.

Oh, well, listen, I

Dan showed up playing this kind of

ruse that he was just this clueless

trust fund kid, okay?

And people bought it. And I sat I sat

there watching him and I'm like, this

dude knows what he's doing, you know?

And I and I said, "Respect, right? Like,

you're hustling, I'm hustling, but you

can't play in this game, you're going to

take everyone's money.

You're bad for business. I wish you the

best."

So, you kicked Dan Bilzerian 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 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 extensions, collections. I was on

the hook if someone didn't pay. I had I

had a full business. I was paying my

taxes, you know, um there was so much

work and sweat equity and I had branded

the game in this incredible way and I uh

I you know, I took notes every single

game. Here are the areas that work, here

doesn't. Let me do some deeper research.

Um

and you know, just really thinking

turning down

cash and cars and free rolls from the

pros

I to get a seat

to protect the integrity of the game and

you know, like taking paying the debts

from my own bank account so that to make

sure people got paid faster. I mean

there was It wasn't 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

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 and so I knew that turning down that

offer, there was a

large

the odds were I was going to lose the

game, but I knew that accepting that

offer meant no autonomy for me, no

freedom, and no dignity, and

What was the offer, sorry?

I had to would have to cap my salary and

make it and and have him approve how

much I'm making.

Why would 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, this in this town?

So he he was he basically said to you,

"Listen, you're making a lot of money.

I'm I'm bringing a lot to the table cuz

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 did you feel about that?

I never want to be anyone's employee

ever again.

But how did you feel about him?

Cuz when you said it, you looked a bit

pissed off.

To be honest.

Uh 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.

Of cuz I think we live uh

in a day and age where a lot of people

try to um

not in a day and age it's it's reality

that a lot of people um

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 and

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, "Don't You're

done."

How could he ensure that you were done?

He had colluded with the biggest

whale in the game. A whale in the in a

gambling context with a lot of money

who's not very good, who'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?

Um

here's my answer.

This was a really long time ago.

Um

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 going to be able to make this

much money again. I'm never going to be

I'm going to have to go join

some you know, I'm going to have to go

work for someone else. I'm not going to

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

to live in this

fascinating, adventurous underworld

where I get to, you know, pull the

strings and move the chess pieces and

and

and I have to go join the real world

where

I'm not extraordinary. You know, I mean,

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 moved to New York.

Yes.

Um 30 years old at this point?

I'm 31 at that point.

Okay.

Yeah.

Um so,

you know, I

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 Room 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.

Um

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.

Um

but then I got angry.

And I had something to prove and there

was just nothing that was going to 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 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. Um I I ran the games with

ultimate integrity.

You know, I 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 going to 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

cuz it seemed like there were 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.

It's

that sort of like billionaire

Wall Street world is not so easy to

penetrate.

Um 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 in New York who'd been doing it

for 20 years.

But, you know, it's it's testament to

when

when the

you're obsessed with something, when

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,

you know, 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 and where I could improve on that. I

already knew I could I already knew I

could bring the branding and the

experience, which was meaningful. It

truly was meaningful.

Um 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 um having

integrity.

And and then I and

you know, 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

um if somebody stiffed, I would pay.

What does a stiff mean?

Meaning they

lost money in the game and then didn't

pay the debt.

Okay.

I I understand that. Surely to get the

chips they have to pay that for them up

front.

No, when you run a weekly game,

ultimately you establish a credit

relationship with someone.

Okay, right.

Um, because otherwise like these people

would have to bring $5 million in cash

to 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.

Called?

They're all just called Molly's Game.

Okay.

Yeah.

Um,

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.

Someone

Explain explain all of this to me like

I'm a chimpanzee from that documentary

you talked about before we started

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. I

started at $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

um,

each round

to

to to to play the game.

To start at the start of the round.

Yeah, and there's a small blind and a

big blind and it just goes around the

table.

Yeah.

And and so, these games played so big,

there was so much action, the blinds

were so high that, you know, 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." And I would

have to decide in that moment,

"Can they pay this?

Are they good for the money?"

Um, 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

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, you know,

was mind-blowing.

But also,

And you couldn't just go to the police

if they stiffed you, right?

No, there's there's no recourse unless

you're willing to go to

um

muscle.

Mafia?

Yeah.

Organized crime.

Why couldn't you go to the police?

Because it's not

illegal to stiff me or a or a 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, what you're saying you you saw

someone lose a hundred million dollars

in a night?

Yes.

How how how did that happen?

The game was playing huge. They were

also playing backgammon. They were also

betting sports.

Obviously, I didn't I can't guarantee a

hundred million dollars.

So, I'm out after a certain point.

But

and that was shortly

before I got in trouble, but that game

that I established, the the combination

of the the big game in LA and the big

game in New York

sort of joined together and became a

billionaire's game, and people over

a year's time would lose a billion

dollars.

People were I mean,

there was 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.

Um and that this was just their form of

entertainment. And what I started to see

is that a

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 I that

sort of started to enable me to make

other decisions that were not aligned

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 um

what had been up until this point

about trying to be an entrepreneur and

be gutsy and make money and and you

know, sort of like source power and but

do it in in a 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

um

pharmaceutical pills like Adderall to

stay up and Xanax to come down and

um you know, just started to live

this life of 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, that sports betting just

became legal. Sports betting so many

people on 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, connect it to

your bank account, watch a tennis game,

pretty much everything that happens in

that game is a bettable moment. You can

also do that with a Charles Schwab

account.

I harbor no judgment for

DraftKings 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 do to

to push an activity

that was ruining a lot of people's

lives,

that was a insult to my integrity. That

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,

Mhm.

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, um,

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. It's not a

win-win.

And all of these things, the the

lifestyle that you've chosen to live in

the way you've chosen to live it, you

speak of the internal conflict this

creates.

Yeah.

Right? Um 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 if I was a fly on the wall

that could

feel what you're feeling, what would I

felt? And what would I have seen?

I was very depressed.

Very disappointed with myself.

Um

and completely

powerless over these forces.

Money.

At the 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 the consistency and formulation of

of, um,

pharmaceuticals. They allowed me to be

productive and not feel myself.

Not feel the world.

Um, I was drinking a lot.

Why didn't you want to feel the world?

What were you escaping from?

Myself. What I was doing.

The

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 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

and provide them with opportunity, the

truth is is that I just 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 it 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.

Um

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 player's 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 cuz he was

he didn't measure up to the

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 hurt him?

You just saying it was bad for business?

Cuz if you said that to me and we're in

a relationship, I'd think, "Okay, you

Okay, you don't want to com- uh

complicate the dynamics. You don't want

some people to know that someone you're

in 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.

And we we had conversations about it.

Mhm.

At some point, the the mafia show up.

Yeah.

So, here's the kind of uh

levels and stages of the

the train wreck.

So, the first thing that happened was I

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, you know? It's a

lot of money.

And

big risk to bring some a stranger into a

room with important people.

And their stories checked out, but there

is 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 ripe for a

corruption.

Um and interesting for them.

The next thing that happened was I had a

Yeah, I had a run-in with Italian

organized crime.

And I I guess naively I thought that

I knew that

gambling was always one of the ways that

organized crime earns.

But, you know, I was having the games at

the Plaza Hotel with billionaires and

players for the New York Yankees and I 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. Uh

you know, if you want to continue to run

these games, you're going to have to

give us a piece.

And

we all know Vinnie in that movie, right?

And I tried to politely I politely

declined their offer and

tried to explain to them in business

terms why that wouldn't work for me and

and just went on my merry way

and started to avoid their calls.

And uh 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 um took everything that was in my

safe including photographs.

The you know, a couple things I had from

my grandmother.

And

you know, 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 in

Colorado.

And so

a couple things here.

First of all, if somebody comes into

your apartment in the you know, in the

real world, in real life

and 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, you 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 I

was too afraid to 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 a danger 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 don't

I have no idea what I'm going to do.

And then I got so lucky.

Uh you know, my only contact with

outside world was

food delivery um

and and then and the New York Times. And

a couple days later I got the New York

Times and it said 125 arrested in the

biggest mob-related takedown

in New York City history.

And I never heard from them again.

But you know

disaster is a coming.

It's just

And the the last thing that happened

before the whole thing blows up was um

you know, for most of my poker running

career I was I was running these games

legally

according to this playbook that had been

written for me by

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 a percentage of each pot

at the end of the game

you winners 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 I got paid a

lot of money. I was making four to six

million dollars a year.

And um

Just from tips?

Yeah.

So what where did that

four to six million dollars a year come

from from

The winners. So the winners would play

in the game and if they won,

you know,

they would tip a percentage, 1 to 5% of

their wins.

Games were huge.

Then 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

and 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 um

and the 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's here

looking for you.

Don't come here."

And so, um

you know, I

I knew finally it was game over.

It was game over.

Mhm.

And you realized that when you got that

call saying the FBI are here looking for

you.

Yeah.

How did you feel at that moment when you

hear Someone calls me and says the FBI

are looking for me.

Terrified.

I want my mom and I want my dad. I want

to go back in time. I don't want to do

any of this.

Don't even know how to process this.

And then,

a couple hours later it got even worse.

I got um

you know, I went back to my apartment

and the whole time, I mean, it's like

you're in a movie. You're

up

looking around every corner. Is Are they

going to be there to apprehend me?

And um

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 nine

million nine hundred ninety nine

thousand ninety nine 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 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 but you know

let's let's just keep it simple.

Someone can't 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 you know, 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 she we're

not interested in her as

you know, we're we're not pursuing

anything criminally against her and if

we are, we'll let her know.

So, I just went I just

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.

Um So, I think my dad was angry.

Um 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 2 years.

For those 2 years, I moved in with my

mom. I got sober.

I

At 35 years old?

No, I'm not 35 yet. I'm

33?

33.

Um got sober.

Trekked to Machu Picchu, did some soul

deep soul searching. Um finally got a

job, moved back to Los Angeles.

7 days later, this is 2 years later,

okay? I don't think anything's coming. I

have

rehabilitated myself, you know, and I've

been living with my mom and my grandma

in the mountains of Colorado.

So, I move back to LA 7 days later, in

the middle of the night, I get arrested

by 17 FBI agents, machine guns, high

beam flashlights. They put me in

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 release said 90 years. I think

realistically it was more like 10.

Um but

um

you know, I have a day and a half to get

to New York City to find an attorney

that's going to 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

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 to bail me out

of jail.

My dad's 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

three to six million dollars.

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, Molly, I really wish you the best,

but without a retainer I can't represent

you. And then I met Jim Walden

who

uh 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 I 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

after the five crime families, who's

looking at my indictment and saying this

is [ __ ]

Right?

And um

and taking on this case and 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 uh

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 my to

who I am. And and one of those is is is

integrity and doing what I believe to be

the right thing.

And

you know, a couple weeks later

the prosecutors wanted to meet me,

and they really wanted me to be a

confidential informant.

Snitch?

Yeah.

And you know, Jim believes this is the

whole reason that they brought the

indictment.

So that you would snitch on the players

in the game and

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 I you know you spend enough time

with people you do get that inside

information. Now I want to 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 game?

No.

you were saying

No no no I'm saying if there was a

character like him right? I would have

Never protected someone like him.

Mhm.

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 going

to drag somebody's family through the

mud and I'm going to be the you know

your your your accomplice with that?

Did they offer to restore your bank

accounts if you

to give me all my money back.

Which was how much money?

Millions.

So they were going to give you millions

if you snitched?

Yeah.

And also

They were going to give me a deferred

prosecution which would have kept you

know sort of given me a guarantee that I

would stay out of jail.

And I went home and I

You know I had a very short amount of

time to 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 a 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 um

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 I'm not going to 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 I used