Molly's Game Uncensored: Mob Threats, FBI Raid & 100M Pots... And Still Won
1118 segments
Hey everybody, the besties are taking
Thanksgiving off. But hey, we didn't
forget about you. We banked a couple of
great content segments while we were in
Vegas. First, here's an interview with
Molly Bloom. You know, she ran the
legendary highstakes game in LA in New
York. I was invited to the LA one. We'll
get into that. And her story was turned
into the feature film and book Molly's
Game. We have a great conversation, tons
of insider stories, who imploded in her
LA game, the best celebrity poker
players, getting shaken down by the mob,
how she got an Aaron Sorcin meeting, and
much, much more. Big thank you to our
friends at Oracle for partnering with us
on this amazing VIP lunch we did in
Vegas at the Venetian. What a great
hotel. Also, make sure you head over to
our YouTube channel. A YouTube exclusive
for the first ever bestie poker freeze
out game. Who's going to win? Chbahhat
Freebert, me, or some of the world's
greatest poker players, Alan Keading and
Jason [ __ ] Also, Phil Helmouth. He he
wound up there as well somehow. So,
happy Thanksgiving. We love you and uh
be safe and we'll see you all next week
for a regular episode.
>> Listen, we have a guest.
>> We do have a guest. Um, she's an
entrepreneur, bestselling author, one of
Fortune magazine's most powerful women.
I didn't know that.
>> Oh.
>> Um, Molly Bloom ran the world's most
exclusive poker game. You probably know
her from, uh, the movie Molly's Game,
which we'll hear a little bit about
today. But Molly's also, I think, got an
amazing sense of what made her
successful and the journey she's been
through, I think, is a really
interesting one to learn from. So,
please join me in welcoming Molly.
Thank you.
All right. Nice to see you, Molly.
Molly, what was the origin of the game?
We know some of our friends played in
it. Uh,
>> well, hold on a second. Jason, you
claimed on our show, let me just read
the notes.
>> The notes?
>> Um, yeah, there are notes here. What did
I say? Apparently, where's the thing
that Jason said?
>> We were on the show and Jason said he
played in the game all the time and
>> No, no, no, no. I was invited to the
game.
>> No, you did not say that. Lisa, please
pull the tape
>> and when you're ready, just raise your
hand and let me know exactly what Jason
said. And then Molly responded on
Twitter that you did not play in my
game.
>> Okay,
>> let's be clear. Molly, did you invite me
to the game?
>> I don't remember inviting you to the
game,
>> but here's the here's the deal. So,
there were two versions of the game.
There was the version where I was
working for someone who would send me a
list.
>> Got it. And I'm sure that you were
probably on that list when I
>> Jeffrey Epstein's list,
>> right? He was young.
>> Absolutely.
>> Okay.
>> But when it was my game, you know,
>> I just remember the Four Seasons.
Was that your game or Okay. So, it was
the Four Seasons. I remember you invited
me and you said Toby's going to be
there, Leo's going to be there,
whatever. And uh they'd love to see you.
And I said
>> they would love to see me lose $50,000.
There's no way I'm going to this game
cuz I was playing in a 510 game. But you
were working for somebody at the Viper
Room. The game started. You then took it
over and it very quickly became a big
game. Famously Toby Magguire, friend of
uh ours we play poker with sometimes was
part of this. Um and then you decided uh
to move it to New York. Just let
everybody know like how this all got
started for you and when you took over
the game.
>> Okay. So I was uh in college game for
the US ski team. had a accident and
retired and kind of didn't know who I
was because sports were my identity.
Went to LA simply because I wanted to be
warm. I'd been cold since I was 2 years
old. And ended up working for this guy.
Uh he had a real estate development
company and he said, "Tomorrow night, I
need to serve drinks at my poker my
poker game."
>> Okay. And so I show up to this poker
game and it, you know, it's A-list
celebrities like you've mentioned, but
also the head of one of the biggest
investment banks, a politician who was a
household name, uh, somebody from the
tech world, and I get to be a fly on the
wall in this incredibly compelling room,
and also, you know, I'm in my I'm 23
years old. This is access to
information, to capital, to power. And
then at the end of the night, uh, they
were tipping me in chips and someone
counted out $4,000 in cash and I was
like, "Okay, I don't know what's up with
this chip token economy, but I think I
might want in."
>> And over the next eight months, um, I
started to learn the to speak the
language of poker, but really what I was
focused on is how do I forge alliances?
because I knew that I would say about 3
months in, I knew I didn't want to just
serve drinks. I knew I wanted to have my
own games. This was an incredible
opportunity. I mean, it really was a
Trojan horse. You could use it to
infiltrate any subset of society. Um,
and I was learning about the world from
some of the people who were active
actively involved in in shaping culture.
So, it was a fascinating uh interesting
time and and it was also very lucrative.
And so, um, I decided to start my own
games and I had eight months of notes of
what I would do differently. And I think
because I wasn't a poker player, there
was an advantage because I was able to
zoom out and see this isn't just about
poker. This is about community. It's
about storytelling. It's about um
belonging to something and it's about
escapism and fantasy. And so I really
started to build on those topics and and
those, you know, I wanted everyone to
come into this room and from the second
they walked into this room feel like
they were in Monaco or in a James Bond
movie. And and so when I started the
game 8 months later,
you know, I was 24 years old. I didn't
think these people who are rich and
famous and were going to come, let alone
make it their their home game. And so I
would say that started the about 4 and a
half five year tenure of the LA game.
>> And when we started out when I was
serving drinks, it was a $10,000 buyin.
I raised it to a 50,000 buyin.
>> And um
>> yeah, that's the number I remember. And
I was like, "Wow, those are high
stakes." Cuz at the time, even in LA,
people were not playing in those states.
And you really elevated the game.
Somehow the mob got involved and the
game moved to New York. Fast forward to
this because this got pretty dark pretty
quick.
>> It did. Um, so I lost the game in LA.
>> How do you lose the game in LA?
>> Well,
one of the players who was making 10x
what he was making in the poker game
became very obsessed with this game and
wanted to talk about it all the time.
wanted to and then sort of to want to
kind of do things that felt wrong.
>> Okay.
>> Okay.
>> Like maybe uh target certain weak
players, maybe uh get some of your tip
money,
>> like actively cheat the game.
>> Yeah. Um
>> angle shoot the game.
>> Angle shoot. And and also was
complaining that I made too much money.
>> Got it.
>> Um and basically gave me this offer.
I'll pay you a salary and you can work
from you. You can be the figurehead.
Uh-huh.
>> Um, and I really wanted to keep the
game. I was making millions of dollars
legally. I was paying my taxes. I was,
you know, like I had mentioned, it was
incredibly exciting and and educational.
Um, but I I didn't want to be under I
didn't want to work for him.
>> Right. There's a power imbalance because
this person theoretically might have
been famous,
>> and the players might follow them if
they boxed you out.
>> Yeah. He he said uh turns out they want
to play at a movie star house. Uh,
>> they wanted to what?
>> Play at a movie star's house.
>> Got it. And is it well known who that
person is?
>> It's well speculated.
>> She never says
>> who they speculated. JKL
>> Toby Magguire.
>> Uhhuh.
>> And he the uh concept also was uh there
was this device called a shuffle master
which was in the first iteration. It
makes the game go much faster. And three
people, myself, Toby, and another person
had a shuffle master in Los Angeles
because you could buy them
>> from somebody in Vegas theoretically,
but they weren't available. And Chimat
remembers because he got an early one
and I used to bring mine to Chimat's
game. He'd say, "Hey, can you bring the
the shuffle master?" He also angles shot
you and wanted you to rent a shufflem.
>> I'll never forget going to his house.
>> No, he Toby. Not me.
>> Not you. Not you.
>> Um, yeah. I I'll never forget. So, he he
was right.
>> Renting out a shuffle master.
>> I mean, he had a tough couple years. You
said it was a pretty big downdraft.
>> So, shuffle masters cost 17,000 at the
time.
>> Yeah. Um, and he was right that we
needed one. Uh, and so he said, "Well,
how about we'll use mine? Just come up
to my house and get it, right?" So, go
to his house and get it. And then I
brought it back and he said, "Um, I'm
going to need $200 for this." I'm like,
"You're you're kidding, right?" Like,
I'm sitting there looking at his
mansion, you know, 200 a shot. I mean,
and about 5 months in, I'm like, "We
need to buy our own shuffle master,
>> right?" Yeah. They they can be obtained.
So, you get the game taken away from
you. The game moves to New York.
>> Sorry. So, Toby Toby takes the game away
and you're like,
>> "Somebody takes game away, right?" And
so, you're like, "I'm moving to New York
and restarting the game there."
>> Well,
I was really pissed and I, you know, and
I
>> it was 2008,
so yeah, I was like, I'm going to build
the biggest poker game in the world. Can
we can we talk like can you just talk a
little bit about how you did that
>> with respect to salesmanship and
building confidence to grow that game?
Like you you moved to a new city,
>> you don't know anyone. How do you
convince them
>> and maybe talk a little bit about what
you learned early on about sales and
earning people's trust and how you got
that to happen?
>> Yeah. So what I focused on
much much earlier than uh you know
eventually I realized that if you're if
you're treating the business if you're
treating the poker game like a business
essentially what you want is you want
nine people seated around a table with
equal playing styles equal skill skill
levels and hopefully you get these
heartp pumping results but at the end of
the year the money changes hands and the
house wins. Okay. But before I realized
that, what I had was
I I was raised by uh parents who were
were very um they they believed in
teaching lessons all the time. And my
dad's was excellence and discipline and
overcoming fear. And my mom's was
integrity, integrity, integrity. And
what can you do for the world? And don't
make people feel like they're
transactions. And so, you know, that's
that's the education that I had. And so
I was a really hard worker and I really
held myself to a high standard. So for
instance, when I started running these
games, there was a lot of pros that
would offer me free rolls, straight cash
if they could play, but I knew that that
would compromise the integrity of the
game. So what I did is I didn't take
shortcuts. I just was trustworthy and I
invested in people and I um you know I
developed relationships and I was very
intentional about
before I walk in this, you know, not
asking them for favors because everyone
in the world was asking them for favors
and just, you know, instead of what can
you do for me, what can I do for you?
Um, and over time, you know, pe I think
people sense that you're a trustworthy
person and that you are really deeply
invested in in their outcome and and I
think that that was focusing on that
relational capital and focusing on
cultivating that trust and being a part
of someone's life. um doing events, you
know, expanding the time that you spend
together outside of just poker and, you
know, doing events with the whole with
the whole crew and and so that's what I
focused on and that was so incredibly
valuable.
>> And a big part of this culture at the
time was unlike say some other games
where we have a group of friends, it's
uh like a high trust environment, we
settle up yearly, etc. The tradition in
LA, at least in the ones I played in,
uh, was you settle up the next day,
people would, and that would be your
responsibility, I assume, or one of your
runners to go collect checks and settle
with people. And then sometimes, you
know, people maybe couldn't settle, and
it can get a little bit awkward. So
maybe you could tell us about that part
of the job that people don't see, which
is, hey, you got to go the next day.
Somebody lost 50 grand, 250 grand.
What's the big loss that you had to go
collect? What was that like? A couple
things. First of all, what shocked me
was if you looked at the net worth at a
lot of these people that were playing,
it would indicate that a loss of a
couple hundred thousand or even a
million wasn't a big deal, right? But
that's that wasn't the case. I I saw
crazy behavior. Um, and when I realized
kind of like cuz I always would ask
myself the question, what's underneath
this? You know, what is what's causing
this flipping of the table, screaming at
me that you're never going to pay, you
know, whatever. And what I kind of got
to is it's fear. Even though it doesn't
make logical sense compared to someone's
net worth, losing money or losing in
general kind of triggers this fear
response. You feel out of control. So my
job consistently was having enough top-
down control to be able to be the one
that could then make that person feel
safe because I saw in other games the
game runner's on the hook for the money.
This person's saying, "I'm never going
to pay you. Then they're both in fear,
then they go get into the sparring
match, games end, things fall apart."
So, it was really useful for me to just
be able to emotionally regulate myself
and understand
what was going on
>> and just talk them down from a ledge and
get them to pay because if somebody
stiffs the game, the game you could
break the game permanently.
>> Well, I've been stiffed and I I wrote
those checks.
>> Really? What's the biggest you got
stiffed for?
>> 250.
>> 250. And the person could afford to pay
it
>> for sure.
>> And they stiffed you and then you've got
to come out of pocket for that and make
good.
>> Yeah.
>> Yeah. That's That's hard.
>> Yeah,
>> that's a
>> But it teaches you to do a really good
job on the on the vetting.
>> Yes. Um I mean I had bank employees on
my payroll basically because in LA
people drive a Lamborghini, they rent a
house in the valley, right?
>> Yeah.
>> So Molly, can you just talk about you
talked earlier with us um when we were
playing poker or during lunch about
someone said I think what sort of stuff
are you into?
>> Yeah. And you said, "I'm really into
like adrenaline
stuff, like adrenaline sports, right?
And you're like competitive skier and so
on." Um, but this feels like that sort
of high stakes environment that you put
yourself in. Where did that come from?
And do you think you selected yourself
into this environment because it feels
like hella skiing?
>> I think first of all, um, I come from a
really competitive family. uh one
brother uh went to the Olympics twice,
was a world champion in mogul skiing at
world champ at 16. Then he went on to uh
after the terin Olympics get drafted
fifth round of the Philadelphia Eagles.
He was an Abberrombi model.
Then he started and sold a tech company
at like literally the highest valuation
like down to the second I think. And now
he's CEO of the X Games. And then my
other brother is Harvard educated
cardiothoracic surgeon at Massgen. So
>> which one do your parents love most?
>> Well, they loved them more, but then
Kosner played my dad in the movie, so I
became instantly the favorite kid.
>> So they they eventually loved you.
>> Eventually, but it took a I mean it took
a lot.
>> It did. Yeah.
>> So that was part of it. Um we grew up
skiing and my dad was really insistent
on fear is not going to sideline you.
And so from an early age, like some kids
get grounded for talking back or you
know, whatever. We got in trouble for
letting fear get in the way or and and
so something started to happen, I think,
in those early years where it was like
this very like exciting experience to
look at something, be afraid of it, and
then do it.
>> Um
>> like run a big game where people go
south for 250k and then you decide, hey,
>> but that was the behavior you were
trained on early on. I think it was a
byproduct of social
>> fear in the face and jump into it.
>> Yeah. And that's a pretty great feeling,
right? It
>> totally and a bit of pride. You wanted
to restart the game. And so you had that
pride.
>> Big time pride.
>> So take us to the game moving to New
York and the mob getting involved, you
getting beat up, the getting pinched and
this whole thing going sideways.
>> Okay. So um moved to New York to to your
uh question really started interviewing
poker players what's the problem in the
current system because there is really
well established games and whatever and
what I found was that there was a
problem with trust um a lot of times
gamers would play in their own games uh
if they did had a bad night the rake
would be higher d wasn't taking a rake
um and then I realized okay well if I
can become the bank for these games and
I can settle um and then provide this
experience um in which you could sit
down next to your hero or you know you
could sit next to somebody who's going
to change your life in business and then
there's no pros and it's all action. Um
this is how I'm going to do it. So I
became the bank for these games. The
game in New York was a $250,000 buyin.
It was 2008 and I remember the first
game the president like was in the
background on the on the television like
giving the state of the union on the
economy and there was like $10 million
on the table.
Um these were insane games. Uh they were
playing insane uh variations of
>> And you love the thrill. You feel the
thrill. Yeah,
>> I did. Yeah. Um
I mean this was the game that like
ultimately someone lost 100 million. So
um so yeah so again um that definitely
made noise
>> even by [ __ ] standards
>> and yeah so and then I just decided you
know I cuz I told my parents listen cuz
they're like please go back to school
you know please finish your like go to
>> I knew what you were doing.
>> Yeah. And I was like okay but I just
have to do this thing real fast. So, I I
decided I was going to go as big as I
possibly can. And then I started smaller
games and it and it got out of control
and some of these guys from Brighton
Beach started playing and I had them
vetted, but their and their stories
checked out. I knew something was off.
It was really off. They were running the
biggest insurance fraud scheme in New
York City history. They had alleged ties
to the Russian mob. My only involvement
with them was they played on my poker
game. The next thing that happened was
um
the Italian mob or impersonators of the
Italian mob uh came to me and said, you
know, we we want a piece of your game
and I turned them down. And then they
didn't just go away. Um, and they sent
someone to my apartment and uh
this guy broke broke in my apartment and
he put a gun in my mouth and he
>> Jesus
>> and he told me that um I work for them
and that if I told anyone law
enforcement or anybody that they had
found out where my family lives in
Colorado and then he beat the hell out
of me and forced me to like, you know,
you
>> took everything out of my safe and there
was money and there was a gold bar in
there for some reason, but also um
things that my grandmother, who I was
named after, left for me. And you know,
it was just terrifying. And I was
completely
terrified, ashamed um for what I was now
implicating my family in. And I couldn't
call anyone. And
>> wow.
>> I kept waiting for their call.
>> Did you think at that moment to just
stop and just say, you know what, okay,
done.
>> Yeah. But I didn't know if it was an
option anymore,
>> right? because they were looking at me
as a big earner now and they they' said,
"This is a warning. It's not it's not up
to you anymore."
>> Wow.
>> So, I didn't know what to do. Like,
literally for the first time,
>> you could confide in anyone.
>> I didn't I didn't tell a single soul.
>> You didn't tell You kept that all in.
>> Yeah. And I'm in my apartment. I can't
go outside cuz it's very clear I've been
assaulted.
And I'm confused as to why I'm not
hearing them cuz about 3 or 4 days go by
and I I don't hear anything from them.
And then I get the New York Times and on
the cover it says 125 arrested in the
biggest mob related takedown in New York
City history and I never heard from them
again.
>> Wow.
>> Dodging a bullet. My god.
>> Oh my god. But yeah, but then
>> Oh my gosh.
>> Then the bullet of me came into play and
you know so then I I just started
getting out of control and like I said
like you know integrity was an important
thing to me but over time I was making
these little decisions. there were just
a little left or right of of where where
I stood and and you know greed money
became everything and and so I started
doing things that um my attorneys told
me not to do.
>> Raking the game.
>> Yeah. Taking a rake.
>> Taking a rake. Now, for people who don't
know,
>> if you have a home game and you collect
tips, it's kind of a gray zone, but
generally speaking, people don't have a
problem with it legally. But in the
casino business, the legal gaming
business, they feel that's their
business to take a rake. And they went
through the proper channels to get a
license to do that rake. And you can't
do that at a home game, right?
>> And so now you're breaking the law,
>> right?
>> To make extra money.
>> Sorry, just to be clear, a rake just
means when you put money in the pot,
they take a little bit of it out, they
put it on the side, they keep it for
themselves. In the casino, they do an
hourly rake, right?
>> Yeah, that's a rake, too.
>> That's a rake, too.
>> Yeah. Yeah.
>> Um different. You were you were you were
taking money out of the pots, keeping
them for yourself.
>> So basically what I was doing was I had
become
much more lenient about who I was
letting in the game. Um and so my
exposure was getting bigger. And so in
some of those games where I was betting
on the players and they were bad bets, I
started to take a rake. This was the
last six months.
the feds had put a confidential
informant in the game because they were
listening to the Russians phone.
>> Um who tracked that and in and then a
couple months later I got a text message
from one of the dealers and they said
don't come here. The FBI is here looking
for you and finally I knew it was game
over and I just wanted to go home even
though I'd pushed my family really far
away. like I I just wanted to go home
and so I tried to book a plane ticket
from um JFK to Denver and my credit card
got declined and then my next card got
declined and I looked logged into my
bank account and it read99,999,000.
Um the division of asset forfeiture
had taken everything because your
property unlike your personhood doesn't
have the presumption of innocence except
for maybe in Florida. Not
>> I'm not up on the asset. Now you're
pinched. You get shaken down by the mob.
Then you get pinched by the feds.
>> So the feds are So my lawyers call and
they say, you know, she can sue us cuz
this is on the civil side, but anything
she says will also be counted as a
confession. They said, do you want her?
Are you pursuing any criminal charges?
They said, no,
I couldn't try to get my money back. I
moved in with my mom. Felt really sorry
for myself. Took me about two years to
put my life back together. Finally got
this little job in LA.
moved back into this little studio
apartment and I thought, "Okay, it's a
fresh start." You know, five days later
in the middle of the night, 17 FBI
agents, machine guns, high beam
flashlights,
>> put me in handcuffs and shackles, and
put this piece of paper in front of me
that said, "The United States of America
versus Molly Bloom."
>> Wow. Wow. What a year.
>> I was really running hot.
>> Yeah. Wow.
>> Um,
>> couple of bad beats. So, I had a day and
a half to get to New York City to find
an attorney. And
>> And you're broke.
>> And I don't have a penny.
>> Yeah.
>> Wow.
>> So,
>> how does it all resolve? How does the
story resolve?
>> So, I found someone honorable and great
to represent me. I didn't have money to
fight it. So, I pled out. The
prosecutors wanted a meeting with me.
Uh, this was the Southern District. And,
um, they really wanted me to become a a
CI. They weren't interested in the
Russians or the Italians. They were
interested in the billionaires and the
politicians and the celebrities
>> who were for poker specifically.
>> Yeah. Let me be really clear. There was
no Epstein in my game.
>> Right.
>> Right.
>> Um so they said if you know if you're
>> they wanted you to be a rat against rich
people, politicians, and famous people.
Yes.
>> And what did you what did they think you
were going to overhear like murder plots
or like like what like what were you
going to be able to tell them? Business
deals. I could have given them leads
>> you over here
>> for all kinds of stuff.
>> Yeah. Crime
>> for sure.
>> Wow.
>> Um
>> was this Pit Barara who was running the
Southern District cuz he he's also
famous for getting rid of online poker.
He
>> had a He's a pretty by the books
>> guy for sure.
>> Yeah.
>> Yeah.
>> And the Southern District of all
districts is known for being the most
hardcore
>> and politically ambitious and
>> Sure. Right. All right.
>> Um, and they said,
>> "So, did you did you go to jail?"
>> I didn't. So, they said, "If you're
willing to give, you know, if you're
willing to work with us, we'll give you
all your money back and we'll give you a
deferred prosecution, which will keep
you out of prison." And I had like 48
hours to make this call. And, you know,
where I got to it was like, this was my
fault. Um, I uh I had near-perfect
information on the laws. I had all these
opportunities. I had loyal clientele. I
found this loophole and I was the one
that decided to make this choice. And so
to turn around and drag these people who
had families through this [ __ ]
um based on my own bad decisions like
just didn't feel like something that I
wanted to live with. So,
>> I turned down that offer and I waited to
get sentenced and we all thought I was
going to prison
and I got a judge who was very
disappointed in my life choices, but
but basically said, you know, you had a
life before this and I had character
letters from professors and ski coaches
and I had um a lot of people show up for
me that had made better decisions that I
had in life and so he fined me a lot and
but I didn't go to But, you know, then I
was 35 years old, millions of dollars in
debt, a convicted felon. The tabloids
are telling this really reductive tale.
Like, where how do you come back from
that, you know? And so I decided, well,
there's a story here and if I can
monetize that, maybe that can address
the reputational harm, the financial I
mean, I'm millions of dollars in debt
and um and so I wrote a book and uh
waited for my life to change and then I
think 10 people read it and probably
like eight of them were related to me.
But it was still my it was still my only
idea and I still kind of believed in it
in my in my gut. So I just made a short
list of the most successful filmmakers
in Hollywood and I was like why not you
know why not just go for it. Um but they
needed to be brave because there was
also a ton of people as you can imagine.
>> Yes.
>> Even though I'd fallen on the sword with
legally even though I hadn't implicated
people in the book they don't want
exposure and I get that. Um, so Erin
Sorcin wrote A Few Good Men, Social
Network, Moneyball, and he was my
favorite writer and also the highest
paid screenwriter at the time, which if
you're gambling, which we always are,
right? It's good bet. Anyway, getting to
him wasn't easy. I finally got to him
and I just remember before I walked in,
I was like, what am I doing?
Millions of dollars in debt. My book
sold 10 copies. Like, I live with my
mom. like
and this is the highest paid
screenwriter in the world, you know.
>> So, you got a meeting with him.
>> I did.
>> And he had you had sent him the book
obviously.
>> So, a somebody that I bothered like
relentlessly.
>> Right. So, you're just to put the sales
hat on again like the the relentless
like pursuit of the sale.
>> Yeah.
>> You were like all over this guy even
though
>> Yeah.
>> you weren't make and you just kept
going.
>> Yeah. And I and I you know I had met
with other screenwriters and they were
kind of a big deal and I was like, "No,
no, no." And my brother's like, "You
can't keep passing. Like you live with
your mom."
>> What did you say when you get in the
room?
>> Um, so I told him my story
and I think like my leg my legs were
shaking, but like I had this game face
on, you know?
>> Yeah.
>> And when I was done, he said, "Well,
I'll tell you one thing, kid. I've never
met someone so down in their luck and so
full of themselves.
>> Wow. It's good character study." Yeah.
>> Yeah. Um, and then, you know,
>> they made an offer.
>> Yep. And then the the paid and then you
used that money to pay down this uh fine
you got.
>> I did.
>> And
>> I just finally finished paying off the
government last summer.
>> Wow.
>> Wow. Congratulations. And I leave.
>> And I guess you know the just to ask you
the hard question which you kind of
answered. I was always wondering like
how does one make the decision to write
this tell all book and the fallout from
that book? I remember in LA people
talking about the book coming out. The
book's coming out. The book's coming.
Everybody was really scared about it.
You didn't put people's names in it. You
specifically chose to, you know, make it
>> I put their name in it if they've talked
if they had talked about playing in the
games,
>> right? So
>> if they themselves, you know,
>> so you took some steps there, but you
did make a decision all these people who
put you in business, etc. to basically
turn on them and to basically tell their
story, but there was no non-disclosure.
You hadn't made any agreements to not
talk about it.
>> Well, I didn't turn on them. I actually
supported them at every turn.
>> Well, I'm just saying like
>> I could have gotten a lot of money back
and a deferred prosecution.
>> Okay. Yes. In that case. Yeah.
>> And then the publishers were willing to
pay me six, seven figures for a
celebrity hit piece. I was broke living
with my mom. Again, I turned that down.
>> Got it.
>> And I chose to work with a screenwriter
that was absolutely clear and willing to
contract it that we aren't ruining any
lives.
>> Great. And the fact that just so you
know is everybody in the who had games,
>> all the dealers, everybody involved had
to sign non-disclosures
>> for the next
>> probably smart.
>> Probably smart. Yeah.
>> Do you still need to face fear in its
face to feel like you're
>> doing what you want to do?
>> Yeah.
>> Um I don't have this I think addiction
to that anymore.
Um,
but I don't I don't ever I I will always
choose courage over comfort. I I pay a
big interior price internally if I
don't.
>> But it's not like this thing where I
need that, you know, that that uh
adrenaline hit to make me feel alive. I
like it. I pick my spots now. I have a
three and a half yearear-old daughter so
I knew before I brought a kid into the
world I want I needed to do a lot of
work on myself right
>> um so that I could be the kind of
>> you learned a lot about yourself
>> I wonder what you could tell us about
the nature of the men who are obsessed
with playing this game and playing it at
these stakes and the camaraderie the
competition and the chaos have you
learned erned about the nature of these
men.
>> Well, again, I think
I don't like to
there's a couple different archetypes.
Okay,
>> tell us.
>> So, there are there are the ones that
are there on a
self-destructive
bullet train.
>> So, it's not just high stakes poker,
right? Yeah. It's
putting their marriage in bad places in
very egregious and and and ways. There's
drugs. There's, you know, it's it's it's
the hedonic treadmill gone crazy.
>> Got it.
>> Um, no more control over themselves,
living for that next fix. Um, then there
are just the highly competitive people
who are very comfortable with
volatility. In fact, prefer volatility
and chaos. um but still have some
semblance of control over themsel
um and
you know and then I think there are
people that play because they love the
game
>> because they like the aspects of it that
make it an incredible game. They they
like the psychology. They like the
>> um making you know seeing the results of
making highle decisions with very
limited information. They like the the
mental
>> and and and and social thrill of it,
>> the camaraderie and the competitive.
>> Who's the who's the best celebrity poker
player
>> in all the years that you saw in these
games? Who is the best?
>> Toby.
>> Toby.
>> Yeah.
>> And who is the second best?
>> He wants you to say Chimoth, but we we
were going to carve him out cuz he's not
>> Look, I played with Toby for 20 years. I
would have said Toby, too. I think he's
he's exceptional.
>> He's a grinder. He's tough.
>> Yeah, he's tough. He I mean he um he was
the only one in the game that was tight.
>> Yeah.
>> Um
I guess second would be Ben.
>> Yeah. Affleck's a good player.
>> Yeah. He he he's definitely smart.
Definitely knows what he's doing. It
depends on where he is in his life.
>> Yes.
>> Yes.
>> Politician wise, can you say or no?
>> I haven't named any of the politicians
because they haven't been named.
>> Yeah. Okay.
>> Business people.
>> Once again,
>> they haven't named themselves, so we'll
leave them unnamed. And Molly, you were
telling us before that you do some kind
of speaking work around sales. This is
where I'm so interested in this. Like
>> what are the things you tell people when
you do those events? What is the big
takeaway from your experience?
>> So a lot of people So there's this small
body of science called effective
presence effective with an A and it
really focuses on more of the subcon
what's going on subconsciously. So, um,
if you work backwards from core human
fears, which I think is always a really
good thing to do after dying, being
alone in public speaking, you know, it's
like
what are people most afraid of? They're
afraid of um not belonging, not uh being
worthy, people stealing money from them,
etc. And so when you start to think
about what
what kind of emotional footprint am I
leaving with these people like in you
know like how can I disarm them and also
cultivate trust at the same time it
takes a level of intentionality and so I
think what a lot of us do is we walk
into a room and we're thinking what are
my what's my resume what are my sound
bites what's my pitch instead of
thinking um
how can I make this person feel like I'm
with them, like this isn't a zero- sum
game.
>> And so, there are just a couple things
that you could do. I mean, listening is
a huge one
>> to listen with full presence, to not
listen while you're constructing your
response, but just ask open-ended
questions. Go down this road with
someone um to, you know, have some
warmth about you and some a, you know, a
like be affirming. Um, but also be
authentic. Um, and and to practice the
hard empathy. Like the easy empathy is
people you relate to, people that have a
similar experience to you. The hard
empathy is sitting down and having
conversations with people whose views
you don't like, whose personality you
don't particularly like, and trying to
figure out or get to a place where you
can understand them,
>> you know?
>> Yeah.
>> Um, and so
>> making that effort.
>> Yeah. making that effort and and you
know it's interesting
humans hate uncertainty um without the
an edited brain and I mean edited by
doing that that work and meditation
whatever whatever your your mind
training tool is um the brain thinks
that uncertainty is a metabolically
unsustainable state so it equates
uncertainty with fear
>> so how can you start to give people that
sense of certainty Um, and also how can
you become aware of it in yourself?
Because if you know that you hate
uncertainty and then what you do is
forge, forge, forage for some subjective
truth and then cling to it, right?
>> Um, that's a big handicap, you know, and
so to start to do work on relaxing with
uncertainty and being more curious than
needing to, you know, try to have this
illusion of control. Um, you know,
there's there's a lot of things that
aren't so obvious or instinctual.
>> Totally. in in impact in the the art of
impact and and connection.
>> It can also force you to let go of
priors,
>> right?
>> Which allows you to adapt and evolve.
And
>> I mean, being able to adapt
>> and being able to court change and even,
you know, reframe it as like this is
exciting or this is interesting.
>> What an incredible life you've had,
ladies and gentlemen. Let's thank Molly
for joining us. Thank you, Molly.
>> Thank you so much.
>> And let's thank also Oracle. Thank you
for hosting. Um, and my lord, we're
going to have a great weekend.
I'm going all in.
Ask follow-up questions or revisit key timestamps.
The video features an interview with Molly Bloom, known for running an exclusive, high-stakes underground poker game for celebrities, business moguls, and politicians. Molly discusses her transition from being a competitive skier to organizing these high-stakes games in Los Angeles and New York. She reflects on her journey, including the pressures of maintaining the game's integrity, facing intimidation from the mob, her legal troubles with the FBI, and her eventual comeback by writing the book that inspired the film 'Molly's Game'. Additionally, she shares insights on building relationships, cultivating trust in business, and the psychological archetypes of the high-stakes poker players she observed.
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