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July 2, 2020 51 mins

We’re bringing you three interviews from the first at-home edition of the Collision tech conference. Laurie chats with Headspace Co-founder and CEO Rich Pierson about the importance of mindfulness and how to live in the present amidst global uncertainty. CEO Hesam Hosseini and Plenty of Fish CEO Malgosia Green discuss how COVID-19 has transformed the world of dating. And lastly, entrepreneur and author Molly Bloom shares her incredible life story — one that you may be familiar with from the 2017 film Molly’s Game. She gives Laurie a peak behind the curtain of running one of the highest-stakes illegal poker games in history.


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Speaker 1 (00:00):
First Contact with Lori Siegel is a production of Dot
Dot Dot Media and I Heart Radio. Take me to
that night. What happened? You know? It was a game
that that sort of lasted over two nights, and there
were a bunch of billionaires in the room, and um,

it was it was an incredibly intense you don't come
up for air thirty six hours, um, and someone walked
away and had lost a hundred million dollars. Hi, guys,

welcome to another bonus episode of First Contact. This time
it's eight three for one. You're going to hear three
quick interviews I recorded as part of the Collision Conferences
First at Home edition. You'll hear from founders and CEOs
about the future of mindfulness and what it means to
live being truly present. You'll hear about love and sex

at a time when physical touch has now become a liability.
You'll also hear from a woman with pretty incredible entrepreneurial instincts.
She was responsible for one of the most infamous underground
poker tournaments in history. First up is co founder and
CEO of Headspace, Rich Pearson. I'm Laurie Siegel, and this

is first Content. Rich. It's going to be with you.
Although we were just saying as we were getting started,
what strange circumstances we are in. But you're a very
fascinating person to talk to during this time because I
think headspace is definitely seeing a lot of It's always

seen a lot of value, but I think probably increasingly
so in this environment. Before we get into headspace in
the era of COVID, I want to just start with you,
um and you personally, you were a successful ad executive
before stress and pressure led you to completely abandon your job. Now,

I know founders talk about these stories, and we talk
about them so much that they kind of lose their
meaning a little bit. So with that in mind, can
you just like paint the picture like you were this
um you know, successful ad executive. You were like marketing acts,
deodorant or something like all those sorts of things. Um
And now you have a wildly successful business looking at

meditation and mindfulness. But what was the day before we
get into it, what was the day that you decided
to stop completely before pivoting? Yeah, I you know, I've
had a really fortunate time in my career in advertising.
I really enjoyed it. But I think setting deodent to
teenage boys UM for many years, I kind of I

just felt like I'd lost a lot of meaning and
I didn't really know where I wanted to go in
my life. But I just knew that I didn't I
didn't want to do that, and I was really struggling
with anxiety at the time, and I thought that my
job was causing me a lot of the anxiety. So
I actually left my job thinking that that would be
the thing that would fix it, and I actually started

to train to become an acupuncturist, which is a much
longer story than we've got time for UM. But it
was really that sense of unease that I had within
myself that was kind of coupled with the anxiety, that
made me think I wanted to take a completely different
direction with my life. And that was really the start
of the journey for for me meeting Andy, which then
kind of led onto Headspace. Well, it's interesting because you

talk about anxiety and Andy, your co founder, was dealing
with quite a bit of loss in his life. He
had unexpectedly dealt with UM a lot of people he
loved dying unexpectedly UM and out of this pain and
out of this anxiety. He went on, we don't have
time for But he went on to become a monk.
You met him, and so the story of Headspace was born.

But this was a company that was born out of pain,
out of anxiety, out of someone looking at death. And
so I want to take that those roots and I
want to look at this moment, we are literally zooming
with each other because we cannot be with each other,
because we are in this global pandemic filled with anxiety,
pain and death. Um. So, now, as a leader many

many years later of a company that looks at this
and whose company was almost I would say it had
a birth out of these ideas. Um, how do you
think this will reshape will reshape Headspace? Yeah? I think
I think human suffering has been around since we've we've
been on the planet. I think human suffering is not

a new thing. I think the world in which we
live in now is particularly difficult because we are just
connected all the time, and I think that has had
a very different effect on the type of suffering that
we've had. Um. You know you mentioned that we start
we actually started off in the recession, like we Andy
I met at the end of two thousand and eight
in London, and so I think we felt at the

time there was that real anxiety in London. Then I
think this is even more intense. And the way that
we think about it is that mental health we always
felt that, you know, in four or five years time,
it would be in every single conversation, in every single boardroom,
and we kind of started to see that happening. We
started we thought that it would be in every school,

We thought that it would be part of health care systems.
I think COVID has just accelerated that journey way way quicker.
I think we've always believed that mental health should be
at the center of health um and you can't. You
can't separate out physical health and mental health like they're
inextricably linked. And I think the situation has forced a
lot of these mental health issues that were always there

under the surface. It's just brought it into the mainstream
in a in a in a much faster kind of way.
And so, you know, we've always believed that that was,
you know, I think a problem, a huge problem that
we wanted to solve. I think it's just accelerated our
our kind of roadmap and our vision way quicker than
we could have ever expected. Yeah, it's interesting. I started
covering tech back in two thousand and nine, whereas we

were coming out of the recession, and I think people
don't understand that scarcity and pain oftentimes breeds um some
of the most interesting innovation and you see things that
you know in some of these edge cases become the center.
So I'm interested to see, you know, what the future
of Headspace like, what is the thing that now you
guys are thinking about that you weren't thinking about two

months ago because of this Well, I think it's more
just keeping up with the demand. I think our strategy
is actually stayed the same. You know. The way that
we think about it is we think about the future
of healthcare and we think that consumers and brands are
going to take an outsized role in dealing with things
that they would have never have dealt with before. And
I think platforms are Headspace are actually an example of that,

where people come to us for things they would have
probably maybe gone to their doctor or healthcare professional before.
They're actually coming to a service like Headspace to kind
of get help. UM and technologies are able to scale
that in a way that you know, we would never
have been able to before. We believe that, you know,
mental health is going to have to be you know,
absolutely at the center of healthcare systems, and we're seeing

that as we work with more and more healthcare system
especially in the in the US, we're actually providing and
creating our first clinical strength product that will be for
chronic diseases. So we're looking at physical and mental conditions
where we believe that a product like Headspace can actually help,
So that will be releasing at the end of this year.

And also our kind of enterprise offering. You know, we've
got over seven hundred enterprises on that on that platform,
and so all of those things that we've been working
on those for years, ever since we started, that's always
been a kind of dream and a vision. I think
this time is just accelerated it all. And for us,
it's really about how do we keep up with the
demand UM as all of these things start to come

towards a much quicker rate UM and head Space is
also offering free subscriptions right to healthcare workers and certain
folks who are really on the on the front lines
and who are dealing with some of these mentally very
stressful situations. Yeah, we haven't always on. We've always had
an always on like kind of social impact lens, which
is to make it free for teachers K through twelve UM.

But we when when covid launch, we extended our free
product offering so that anyone could get access to it
in the weathering the storm section, and then we made
it free for all healthcare professionals in the NHS. We
partnered in the UK if you've got an MPI number
in the US, so if you know healthcare workers and
they're struggling, please let them know about it UM And

in France we partner up with the Health Ministry in
France as well. So yeah, we've tried to do as
much as we can and react as quickly as we
could in the moment as it happened. What do you
think the future of work looks like? I think about
mental health than you know, and and a future where
work isolated, where we're not working together. For you specifically,
how did you handle the transition with your employees home? Like,

first of all, be honest with us, because everyone is
you know, I'm I'm a little over everyone saying that
it was completely seamless and that we're all experts and
working from home, Like we had issues setting this thing up,
So like, let's can we just be completely honest, Like
be honest as a leader, because you're you're in the forefront, Like,
what are some of the challenges and challenges you faced
as someone who's a leader in the mental health space

helping your employees be mentally healthy as they were going
and working from home? What will be the challenges we
face as we trying to shift the workforce, uh in
a more isolated way. I mean, I'd love to meet
the leaders that found it seamless and it was it
was easy. I think, yes, we might have had technology
in place that is enabled to do this. That's one thing.

I think. The human element of it is very, very different.
You know, I'm in my bedroom at the moment. I
can hear my wife and my young baby life crying.
But my young baby is crying. You can't probably hear it.
But like that's the reality, and every single person situation
is very different. You know. If I just take our team,
there's people that live by themselves. That's really tough. You know,

we've we've just been it's been announced, it's probably gonna
you know, lasting to September we've actually told our team
that they're not going to come back to work until
September UM. So there's people on their own. There's people
have got kids that aren't gonna have a school year.
There's people that have got family that live abroad, like
all my families abroad. You know, my mom is not
very well like. There's so many stories of that, and

so for us, it's been how do we be as
flexible as possible. So there's a few things that we've done. One,
we have more regular communication on Zoom with the whole company.
We've actually instigated mind days, so every Friday we now
have a mind day where it rotates so every Friday
there's no meetings, but every other Friday people can take
that time off to actually just have some time away

from the computer screens. Because we've just found that, Yeah,
technology is enable us to work, but to be stuck
on your computer screening and you know, in a not
an ideal environment at home is not easy on his
mental health. So we definitely haven't worked it all out,
and we're trying to be as personalized with the team
as possible, knowing that every single person situation is very,

very different. Yeah, Twitter asted employees could work from home forever.
Would you ever consider that? I think, look, we're definitely
thinking what does the future of work look like. I
definitely don't think it's going to be um, you know,
big offices all over the world anymore. I really think
it's taught us that we can operate remotely in a

really thoughtful way. But for some folks it's really important
to have that social connection UM and so I think,
and especially around creativity, I think there's ways in which
we can use space in a more thoughtful way. But
I think the way that we're going to work is
is changed forever. Like I really don't believe that it's
going to go back to the way the way it
was before, but I personally I would like it to

be more than augmented and choice based kind of approach,
which is how we're thinking about augmented as in what
I think, like as in I think there's opportunities to
have creative exploration and UM and kind of coming together
as a community in real life, but giving people the
choice that you know, if you've got a young family,

actually it's really amazing to be able to have Mondays
and Fridays working from home where you can spend more
time with your kids, like one of the best things
I think, beside the home schooling, which is super tough,
but to be there for your young children. I think
for parents when we set we've got a lot of
parents are Headspace in particular, and so we've set up
a parents group. So there are things that I think
of really positive, but there's things that are difficult with it.

So how we all meant those things to make it
work for everyone, I think is the way we're going
to try and approach it. Um. I gotta wrap it soon.
So two quick ones. Um. The thing that sets Headspace
apart that I've seen your investors talk about is a
data driven approach. And you know, using a data driven
approach to meditation and mental health. Um, Because I know

this is a crowded space from the time that you
guys have started this. What does a data driven approach
to meditation and mental health look like? Um? Does it
project when we feel bad? Like? What does the future
look like? Take us far into the future. Sure, I
think if you think about personalized health and you think
about all of the big operating systems that are going

to be built and all the data that apple Amazon
and all the big guys are going to start to
collect We're going to know more about our health than
we've ever known at any other time. I think the
way that we think about it headspace is, you know,
we can be the intervention layer that sits on top
of all that data and gives you a really personalized experience.
The best way to think about it is imagine when
Andy had his clinic and he taught people one on one,

and you would go in there and you have a
very personal conversation and he would direct you down a
path to help you with the thing that you wanted
to help the most with. We believe that tech oology
and data can recreate that. So how do we recreate
a clinic experience in real life through through the product,
But do it in a way that is, you know,
where data is incredibly private and that people have the

choice to kind of opt into that. They're the kind
of things that we're really excited about. So kind of
personalized medicine through these these digital interventions are the things
that you know, we want to build for the future.
Last question, Um, you met a Buddhist monk when you
were thinking about quitting your job, who later became your
co founder, he asked you one question. The first question
he asked you was how much of your life do
you spend in the present moment um? I want to

ask you that question now. How much of your life
now do you spend in the present moment versus versus then?
Way more than I did then, but definitely not enough.
I think we there would be the answer. I mean,
it's such a hard thing to be in the present
moment all the time you've been like you are, but
definitely I've seen I've seen huge improvements since I've I've

practice since I me and in your advice to people
about living present during this moment, I think for me,
I think that's the best thing that we can do
because we do not know what We actually never know
what's going to happen in the future. We just pretend
that we kind of think that we do. It's a
control thing, and so I think the best thing about
learning to be in the present moment is that we
can rest in uncertainty. And there's never been a more

uncertain time. And I think the practice of meditation and
mindfulness can really help you with that, which is I
think the most valuable skill that we can all teach
ourselves at the moment. Okay, we've got to take a
quick break to hear from our sponsors. More is my guest.
After the break, My next interview is about the future

of love. What does it mean to even find someone
in the midst of a global pandemic when we're all
encouraged to stay apart, and how will online dating transform.
Here's his Sam Husseini, the CEO of Match dot Com
and Plenty of Fish CEO Malga Green. Guys, I'm excited

to be here with you guys, even though I say
be here, be socially distant and on zoom. Um, you
both are at the forefront of online dating, and obviously
I think this is a moment where, um, physical touch
is almost dangerous. So what strange circumstances we are in.
So I'm excited to be here to be chatting about this.

I would love for both of you separately take me
into the dating war room like it's march. Um, the
pandemic is upon us, at least here in the United States. Um,
what were the conversations you guys were having around dating
and how it was going to change Because physically, we
potentially weren't going to be able to actually go out

and meet each other. What were those conversations like, sure,
maybe I'll start first. And foremost, we were very concerned
about the situation, and we wanted to make sure that
our members were aware of the guidelines from their local
government authorities, so we sent out notifications to all our

members making sure that they were following social distancing recommendations.
And then internally, of course, we also turned our focus
to our employees and making sure that they were safe.
We were one of the first companies here in Vancouver
were based to allow everyone to work from home and
closed our office pretty quickly at the beginning of the pandemic,

and we're we've been able to work from home pretty easily,
So we're very lucky from that perspective, and were we
were concerned. We didn't know what was going to happen
to the business and how people would react. But pretty
quickly we started noticing that there was an uptick engagement
and usage on our platform, which was extremely encouraging UH

and so we set in motion our plans to accelerate
the rollout of a live streaming feature that we had
been testing for the past few months. Some how about you?
What were those conferences? I mean, were you nervous? I mean,
it certainly seems like the business could be under attack,
like people aren't actually gonna be able to meet What
were the what were the hard conversations like at the

beginning of this, Yeah, we didn't know what to expect, certainly. Uh,
you know, we haven't seen something like this before, although
in my twelve years a match we have seen quite
a bit. And one thing that we've seen is that
UM love and the desire to community for connections with others,

especially for singles, is really strong and that's sort of
bored out. We see that during the pandemic, singles are
still looking for a meaningful connection UM. And like Malgosha said,
we have seen increasing engagement double digit growth on the
match side, and increased engagement, the depth and length of
conversations that people are having. And I believe it or not,

we're sort of seeing a swing back to romance UM.
Given like you said, physical touch is off the table
and those pressures are lifted and we're all virtual dating now. UM.
We found that UM folks are having more meaningful connections
and as the return to romance, Yeah, how are you
seeing people adapting to virtual courtship? I mean, like we

all knew, I mean by the way before. And I've
interviewed dating app founders from the beginning of the times
they've launched these apps, and the biggest problem was like
the swiping too much and everything was moving so fast.
And now we're beginning to hear what you just said,
which is okay, Now we're almost going back to this
like old romance of people having to slow downs. Like,
how are you seeing virtual courtship change in the coronavirus era?

So we are seeing video getting more more adoption um
than it has in the past before COVID nineteen. You know,
our dators show that you know, mid single digits, five
to six percent of users were even interested in trying
video dating. Uh, that number has jumped up to almost
seventy now during the pandemic, and so at match we

pivoted fairly quickly. You know, we are one of the
only platforms dating in general. We're one of the only
platforms that connect you with folks that you don't already know.
So and we also serve singles who we found we're
feeling more socially isolated, so we almost saw it as
our responsibility to do everything in our power, any tool
that we can we can um roll out to help

singles feel less isolated. So that match we pivoted pretty
quickly and within two weeks actually launched our one on
one video dating feature. It's called vibe Check, and we've
seen great usage of it during the pandemic and it's
a feature that before these times we felt would have
been would have had lower adoption, and it's been a

great tool for members to stay connected and actually continue dating.
You continue feeling that feeling a meaningful connection through the time. Well,
I mean it does feel like look before, it's a
little weird to video chat on a dating app, right,
Like there was a certain I would say stigma. I
mean maybe I'm I just say there'd be a certain
stigma to doing that. But something about this pandemic has

changed that are using that. Melgosh, I know plenty of
Fish also launched a video feature very early on. I
think you guys were one of the first to do that.
What was the thinking there and and you know what
have you guys found? Yeah, Well, to you to your point,
I think people have very quickly gotten used to video
We ran a survey about a month ago and found

that seventy five percent of singles feel much more comfortable
video dating now than they did before the pandemic started.
And that's a pretty remarkable change given the short amount
of time. I think people are face timing with their
family and they're having zoom calls like this one, uh,
whereas before they were having in person meetings, and so
they have gotten used to things quite quickly. And in

terms of our live stream future, just to explain a
little bit what it is, it's quite different from the
one to one video on match and it's a one
too many uh and think of it as as having
a host and then there's many people that can join,
but they're not on the video and they're able to
chat with one another, text chat and interact with the host. UH.
So that it's a slightly different format and that's something

that we were working on since last summer, and the
feature was in response to something we had been hearing
from our members that it was really difficult to get
out on dates on a regular basis. Dating is expensive.
You have to go out and you pay, and it's
not all expensive from a cost perspective, but it's also
expensive from a time perspective. A lot of people have

children at home when they're dating our elderly parents, and
it's really tough to get out and meet people. So
we started looking at the live stream Future as a
way to really make it easier, lower pressure way to
meet people online from home. And so when the pandemic
hit and we had already been testing this feature since
late last year, we realized that this was a perfect

time to roll it out to all our geographies, and
we did that very quickly, in a matter of a
couple of weeks, and the response we've seen from the
future has been phenomenal. Uh in a shurt amount of time,
one in five of Plenty of Fish members used the
live stream feature on a daily basis, And can you
just explain it? So, like, let's say we're on it
right now, how does that work? So there there'll be

one post and anyone could live stream, So any member
Plenty of Fish, any single can go on and start
live streaming, and a lot of people share their life.
They talk about what they're doing and the challenges that
they're having. Some people share some of their favorite hobbies.
Some people will sing uh, and other people joined the
live stream and then just chat with the streamer. Uh.

And then we have a couple of really great features.
Of one is called next Date, so you can go
on there and then you can enable this next date
mode and it's kind of like video speed dating and
people will come in in audition to be your date.
And it's been really phenomenal adoption because we've had this

was looking at the stats in this last weekend alone,
We've had twelve thousand matches a day. So people are
really connecting on video through through the future, are there?
I mean, I'd be curious to know it not for you, Like,
what do you guys think? I know that so many
folks are looking at live streaming like while their home
and in different ways. What do you think is the
future of video for online dating? Even in a post

coronavirus world, There's no question video is becoming normalized. I
think about my four year old daughter who is doing
schooling over video and she's a pro addit after her
two short months. So video is here to stay. And
on Match, our platforms always been around meaningful connec stions.
You come to Match when you're looking for a real connection,

and um, we found that one on one video can
be a great way too, As the name of the feature,
vibe check implies, just get to know if there's if
the vibe is there, if if this chemistry there, if
there's a spark there before you actually go on a
first state. So in a post pandemic world, we do
I do see uh one on one video playing a

pretty pretty interesting role and a great role and one
that can maybe replaced the first state where a quick
vibe check on the match app will let you know
if there's a spark there whether you should invest the
time to go and have that I r L first date.
This maybe goes into because there's always been AI and
algorithms to try to match is for good, but you
can't really replace chemistry, right, that's right. We we've actually

remembers have told us that within ten minutes of seeing
someone on video, they're both to tell if this chemistry there,
and ten minutes is a much shorter amount of time
to invest in going on on a full first state.
Question for Melgo, as you think about introducing live streaming,
I gotta put on my my tech and ethics hat um,

you know, how do we make sure this doesn't turn
into chat roulette to some degree, like what privacy features
or how are you guys making sure that everyone behaves?
Because if I know anything about when people get the
access when it comes to dating and sex online to
to live streaming, people can behave poorly. So how are
you guys making sure that everybody's behaving? Great question. It's

something that was certainly a huge concern of mind when
we started looking at the future, and UH, I feel
pretty comfortable that we were addressing this this concern. Of course,
we'll continue working on it to make it better. You
can always do more. But we have live AI moderation

of all of the streams, and on top of that,
we have hundreds of human moderators that check in on streams.
In addition to the AI moderation that we have. UH,
there is a very prominent reporting feature. So if someone
feels uncomfortable with what's happening on the stream, whether the
nudity or any sort of um, you know, bad language

or you know, anything illegal happening that clearly conflicts with
our very clear community guidelines. Everyone must review the guidelines
before opting into the future. Uh, they the moderators step
in right away. The person is kicked out, and depending
on the severity, they even get to get a warning
or permanently banned uh from from the future and from

the platform. As you guys went into kind of building
out this new these new products and ways people can
interact in the pandemic era, Are they there uh, features
that you decided not to implement of for safety reasons
or ethical reasons. I saw something about face filters, I mean,
you know, privacy or I mean, are there certain things
you guys decided not to do. So our face Ultra

band was unrelated. It was this past fall. It was
something that we we implemented because we heard from a
lot of our members that they were looking for more
authenticity online dating, and face filters are really the opposite
of authenticity. You're you're you're hiding what you look like
or accentuating uh your appearance in some way. That's you know,

never good because eventually the person will meet you in
real life and they want to see what you actually
look like. So I think authentity is really important. So
that's why we instituted the face Filter Band last fall. Um.
But to your question, I don't think there's anything that
we uh not pursued. Many jump in Um, so we

take privacy very very seriously. One of the things that
we've decided to do, we decided pretty early on, is
never to monetize our members data. So our business models
completely different. Um, you just pay to access more features
in that platforms. And to your point on privacy, you know,
dating is a pretty private matter and we want and
when we decided to not monetize any of the data

that share about platforms, this is when I say our
I mean match em plenty of fish all being part
of the match Room portfolio. Is there anything that's been
really surprising to you about how your users have been
dating during this time and adapting too. I know you
guys have done tons of studies. I was looking at
some of the stats you guys sent over. Is there
anything that's really surprised you about how people have been
adapting to this new environment? Yeah? Sure, I think one

of the most surprising things that we've seen is just
much higher engagement from women, and so women have been
participating at higher rates. And this is fantastic because this
is something we've been hoping and working on very diligently
for a while to make women feel more comfortable and
be able to engage more on the platforms uh and
right now that that is definitely happening, and I think

it speaks to something as I'll mentioned before, that dating
has slowed down. There's a return to romance, and I
think that really appeals to women and they feel like
very much. Uh, you know, this slowing down, more conversation
and spending time getting to know one another, that really
kills them. Um, how do you, somed like code romance? Right, like,

how do you code that into an online experience now
that people are paying attention? Now people are slowing down.
Finally we have this shift in online dating that people
were you know, people were criticizing this for a long time.
So how do you code that into the product of
the future of what online dating will be now that
people are finally slowing down. One of the the approaches

that we've taken is to not just relying on AI.
Loan love is not something that you want to leave
in the hands of AI, I always say, Um, So,
we actually have a team of human experts at Match
that are available to all of our members to help
them navigate and actually help them get the most out

of the platform. And so I think that at the
marriage of sort of human expertise along with AI is
really the answer, and we are looking at ways. Then
now that we have this team of experts, have ways
where they can assist our members even more, and we
have sort of big plans. I can't get in someone

right now, but they clans down the road of how
AI plus human expertise can be the future of of
matchmaking and online dating. Well, I would be curious to
know what that looks like. Uh like a combination of
like her, like her, movie her, not not like her.
I think it's all how to other singles find their match,
the real match, not just relying AI and algorithms alone

and experts and some human intervention to help you turn
the knobs and make sure that you're focusing on the
right things like you're being way too superficial kind of thing.
For example, dating in the real world is never around
the checklist, you know. We we sort of flex all
the time based on the chemistry and in person interactions

that we have. So we think that UM a human
expert and help guide uh remember our members UM to
focus on what's important. And also with in combination of
features like bib check, where you can sort of go
beyond what's on paper, so to speak, or behind the screen, uh,
and see someone face to face. Um, you can get
at the intangibles when it comes to finding chemistry. Well,

last question, because we've got to wrap it as as
the leaders of large companies responsible for our hearts in dating,
what have you guys learned about love? I think the
main thing that I've I've learned through all of this
uh time in the pandemic is that love for severes.
We have heard from our singles the majority of singles,

almost three quarters are hopeful that they were going to
find a match during this pandemic, which is extremely encouraging,
and it speaks to how important human connection is in
our lives and it really is an essential part of
our game. I go that I don't think um uh
you know, I was around that match in two thousand

and eight when the last recession hit and we found
out then that that love was recession proof. Um. And
we've seen it through this pandemic again that our members
have found a way to continue dating, continued form meaningful connections.
And I heard about a match couple who um I
was supposed to get married during the pandemic. They were

in mature enthusiasts and they had to cancel their big
Alaska wedding. But the two of them went to an
animal sanctuary and had had their wedding. UM just them
in the wild, and actually a real life a bear
was their ring bear. Believe it or not. So UM
examples like that I would hear about all the time.
And we find that love is going to get through

this pandemic and anything else sort of faced down group.
I like that love is recession proof and pandemic proof. Okay,
we've got to take a quick break to hear from
our sponsors. More is my guest after the break. My

last interview is with Molly Bloom. Now, her name might
sound familiar because her story was adapted into a film
called Molly's Game by Aaron Sorkin. Molly nearly qualified for
the Olympics before an injury completely changed her plans, and
let's put it this way, she went in a completely
different direction. She started running what's become known as one

of the most infamous high stakes booker games in history.
It was an underground game attended by everyone from celebrities
to politicians, even members of the mob. Here's Molly, Molly
I I'm super excited to be doing this with you,
just to give you sense. I was in quarantine earlier.

In the first movie I watched was Molly's Games, so
I was very excited when they said I would be
chatting with you, um, because to just like go right
in like you, just to give folks a sense who
have not seen the movie, who don't know your background,
like nearly qualified for the Olympics before an injury that
changed all your plans, moved to l A, worked in

a bar, then became responsible for one of the most
iconic underground poker tournaments where you had everyone from like
Leonardo DiCaprio to a famous politicians showing up. You almost
um serve time in prison. I mean you just have
such like a fascinating background. Um. By the way, for
folks who haven't seen the movie, there's just so much

heart and nuance involved too, so like you just can't
like you just it's such a fascinating story. Like let's
just start with like, how did you go from Olympic
hopeful to like underground poker kind of that time to
explained that to my parents for you know, twenty years Um,

you know, I grew up in this very high achieving family.
In my family, if you it was kind of like
if you weren't number one in the world, it didn't register.
My brother is a Harvard educated cardiothoracic surgeon. My other
brother is a two time Olympian also, UM spent time
playing in the NFL. And I had this plan, right,
it was gonna be law school and the Olympics, and UM,

something happened. You know, I tripped on a stick. If
you've seen the movie It's metaphor and reality. UM. On
my Olympic qualifier run, I skied over this small little
branch that UM caused my ski to pre release, and
everything was derailed. So I think I was primed for
a bit of a rebellion. UM. And I went to

Los Angeles just to take a year off in between
undergrad and grad because I just wanted to like not
be serious for a year. So I got a bunch
of restaurant jobs and then I ended up waitressing at
this poker game that UM was so compelling to me,
not necessarily because of the poker, but because it was
access to all these different people from all walks of life.

It was access to their information, to capital to power,
and um, it was super compelling to me, and I
wanted to stay in the room in the beginning for
the for the learning. You know, there was just so
much information flying around the tables. There were tech giants,
there were finance people, there were heads of studios, heads
of banks, and it was just this incredibly rich environment

for information and for learning. And then I started to think, well,
if I could own this, you know, I could curate
these games, and I could access any subset of society
that I wanted, and so it became a very compelling
thing to pursue. It was also insanely lucrative, and so

I ended up you know, my my short my plan
was get in, create this network, make a bunch of money,
and then get out. But that's not how it worked, right,
But you know that that was the lure of the
in the beginning, and sort of like the preconditions to
why I was so amenable to kind of falling down
this rabbit hole and saying yes. And it's like you,

I mean, it was high stakes poker and you still
some of the most powerful people in the world, and
like these like addictive high moments, like what what made
a great poker player, and what was like and you
can even get specific with us, like because I feel
like now it's like now we've like opened the doors
on it, Like what was like the dark thing? Like

what was the thing that like brought people down? And
you can give us names do if you want. Um. Unquestionably,
the thing that brought people down was greed and ego
and um, getting out of a logical brain and into
an emotional brain into to a mode of like seeking
revenge or seeking to prove something real ego driven. Um.

The people that consistently one and that did well were
able to stay composed, They were able to stay rational,
they were able to walk away when it wasn't their night, um,
and they were happy for the winds and and we're
able to let go of the losses. So so much
of poker and so much of life is about this

like sort of self investigation and this healthy mindset is
keeping your mindset healthy, making sure you're not going into
these sort of degenerate modes that are that are very
ego driven and green driven and and everything else falls
by the wayside. Was there any um after all of this,
I mean, and there's such a crazy story that you'll

almost you know, you being arrested and this you know
a lot of this depend on you and you almost
going to prison. I mean, are there any scenes that
stick with you from those games and those nights? You
had some of the biggest celebrities in there, the biggest politicians.
There was danger, there was there were moments that you
saw people at their highs and their lows. Were there
any scenes that after all of this, you're sitting right now,

you talk about being in your mom's home in Colorado, Like,
does anything stick with you? Any scene? Yeah? For sure,
I mean there are a lot of scenes and and um,
you know the night that I saw someone lose a
hundred million dollars was just you know, how's this reality?
And then how am I at the center of this?

Take me to that night? What happened? You know? It
was a game that that sort of lasted over two nights,
and there were a bunch of billionaires in the room,
and um, it was it was an incredibly intense you
don't come up for air thirty six hours, um, and

someone walked away and had lost a hundred million dollars.
Another scene that will be forever ingrained in my mind
was when the the sort of hitman for the Italian
mob came to my apartment and stuck a gun in
my mouth and ordered me to or basically insisted that
I give them a piece of my operation. I mean,

you know, you don't get from good girl from lovel in,
Colorado to taking on the mob and breaking the law
and running the biggest gambling enterprise overnight. It's these It's
these small micro choices that sort of culminate, you know,
But in those moments, you're like, this is who I
am right now, this is my life? How did how

did I? How did I get here? And I've had
so many of those moments. And in the beginning there
there are moments that play out like a movie scene.
I was twenty four years old and all of a
sudden had all this money and all this power, and
you know, I would go into these um presidential suites
and everybody knew my name at the high end hotels,

and I you know, I bought a Bentley with cash
and like sort of that that that version of it.
Um and then and then it got extremely dark and
and um, you know it definitely, uh, my life was
in ruins when it was all said and done. Um,
but there were there were there were moments in both

of those categories in like, oh my gosh, look what
I created from nothing? And then oh my gosh, look
what I created. You know, how do you think this
moment um? I don't even know if this is an
okay question, but like, how is the game of poka
relevant to this moment right now? Like it certainly seems
like this is a relatively high stakes moment that we

are sitting, and we were sitting in a moment of
pandemic and race riots, and it certainly seems like the
stakes could not be higher. Yeah, you know it, It's
felt like there's a swell for a while. I think
we're at a tipping point. And I think our choices

at this right now mean more than they've meant for
a long time. Um. And there are those moments in
a poker game, you know, you can just it's friendly,
it's friendly people play, and then all of a sudden
there's a huge pot and everything matters and your choices
means so much more um than they have previously. And
I think that's where we are right now. Um. And

it's really important to you slow down and stay in
that objective rational mind and not give in to fear
and sort of what the what the rest? You know,
what what the crowd is saying and all that and
and and stay objective and stay um within you know,

aligned with with what you believe in and your morality
and and act wisely because it really matters right now.
When you had the FBI show up at your door,
when you thought you were going to be going away
for a long time, Um, how did you what? What
was your head like, not a nice neighborhood to be in?

Like what what take me into that neighborhood? And how
did you deal with the high states um pressure of
that of that moment? Like what advice would you give
to people in their head like mentally dealing with that.
I think you never know who you're going to be
until you get to a really big breaking point. Yeah, um.

And I think it comes down to making a simple choice.
Am I going to let this crush me? Or am
I going to do whatever it takes to be on
the good side of history too, um, to make it work,
to battle back, to have redemption, to be part of redemption.
And I think you have to realign to that choice

every day. I think there are things that we can
do to keep ourselves healthy. I know that I've leaned
in even more to the things that I know that
that keep me out of fear and that U sort
of keep me in solution and in contribution. I think
one of the greatest tools I've ever found for that
as meditation. It really is extraordinary in in training our

mind to stay focused and stay um sort of out
of the lower brain, the the amigduala stuff, and then um,
you know. I think the other thing is is that
we can um instead of acting on fear, we can
act contrary to fear, which is be of service. You know,
do the things that scare you, that can that can

make you part of this larger solution in the world
to yourself, whatever it is. UM. So I think it's
just not giving in two to these sort of instincts
or or these demands and continuing to go high, continuing
to go high, continuing to like overcome limitations. But I mean,

I just I don't want anyone to think that during
those times where I had burned my life to the
ground and I was hopeless or it seemed hopeless, that
I woke up every day with like this rosy disposition
That's not how it was at all. Um. It's just
a matter of continuing to fight the good FOT. I
think you know when um, a lot of I think

what where a lot of people looked at you in
a different way was after Molly's Game, Right, This this
movie that came out that shed a different light on you,
that showed you in a more nuanced way that when
the tabloids when your story initially came out, I mean
not to go full on, but you know you were
made out to be a certain way and the tabloids
as this, you know, kind of like crazy woman who

was like this people and like no, I mean, I'm
saying it, you know. And what I don't think people
understand is that you fought to have your story told.
I think that you fought to change the narrative. UM.
And you actually sought out Aaron Sorkin, who for folks
who don't know, it's like a famous director, he was

social network. That you fought to change your story, UM,
or to have your story told, UM in a dimensional way.
In a dimensional way, Why what was the misconception about you?
And tell me about what you told Aaron Sorkin? Okay, UM,
So for sure, the tabloid reports were so one dimensional

and they went straight to sort of what happens so
oftentimes when we're talking about women, what she looked like, UM,
who were her romantic endeavors and sort of like the
the manipulative nature of it. And you know, I built
a a huge business, and I was the bank for

this business, and I was the owner and operator and
I ran it very well for seven and a half
years until I made some really poor choices. And um,
I knew that I I needed to sort of do
a rebrand because I knew the truth and I knew
that there were mistakes I made, and I think, I
think that's just important to include as a but I

wanted a full and balanced picture, and I, um, I
really believed that if I could tell that story, there
would be that could be a springboard too, to a
second chance. And yeah, no one wanted to touch this movie.
Everyone said, there's so many powerful people in d C,
l A and New York that will never let this
get made. And everyone was terrified. Um, and I just said,

you know, I'm gonna just go straight to the top
of my favorite writer in the world and see if
he might be interested. And Um, I went and I
sort of told Aaron my story from start to finish
and the parts that weren't told in the press, and
and um, you know, he went into the meeting thinking,
I'll take this meeting as a favorite to a friend,

but I'm not so interested in in this or or
what this is. And he left with a very different opinion.
And that's why I think it's so important to tell
the story of our lives in a balanced way, in
a in a dimensional way, and and for also everybody
to understand that things are not black and white. We're

not always just good or just bad. Sometimes it is
like that, but there is so much nuance and and
we get to be human beings, you know. And that's
what I was so happy that he recognized and felt
passionate about about writing and directing. I've got to I've
got to stop it. Um, But I'm gonna ask you
one quick question. You are clearly okay with risk, You

ski down big mountains, you run big poker games. What
is it about you? Um? Ironically, I was a pretty
fearful kid. Um. I had parents that taught me that
it's okay to feel fear, but it's important to walk
through it, because fear will rob you of dreams and

of a full life. Um. And so it's in it's
in that practice of okay that scares me. I'm just gonna,
you know, take a deep breath and twenty seconds of courage.
I'm gonna walk in and see what happens. I hope

all of you are doing well in these strange times,
and I hope you guys are adjusting to a new normal.
Most important, I hope you're staying healthy and somewhat sane.
To watch these interviews and more from the Collision Conference,
check out Collision comp That's c O n F dot com.
And for more from dot dot dot sign up for
our newsletter at dot dot dot media dot com Backslash Newsletter.

We'll be launching it soon. First Contact is a production
of dot dot dot Media Executive produced by Laurie Siegel
and Derek Dodge. This episode was produced and edited by
Sabine Jansen and Jack Reagan. The original theme music is
by Xander Singh m. First Contact with Lorie Siegel is

a production of Dot dot Dot Media and I Heart Radio.
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