All Episodes

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. Match.com 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.


————————————

Show Notes


Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

See omnystudio.com/listener for privacy information.

Listen
Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
First Contact with Lori Siegel is a production of Dot
Dot Dot Media and iHeartRadio. Take me to that night
what happened?

Speaker 2 (00:14):
You know? It was a game that sort of lasted
over two nights, and there were a bunch of billionaires
in the room, and it was it was an incredibly
intense you don't come up for air thirty six hours
and someone walked away and had lost one hundred million dollars.

Speaker 1 (00:46):
Hi, guys, welcome to another bonus episode of First Contact.
This time it's a three for one. You're gonna hear
three quick interviews I recorded as part of the Collision
Conference's first at home edition. You'll hear from found and
CEOs about the future of mindfulness and what it means
to live being truly present. You'll hear about love and

(01:08):
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 poper tournaments in history. First up is
co founder and CEO of Headspace, Rich Pearson. I'm Laurie Siegel,

(01:30):
and this is first Concept.

Speaker 2 (01:38):
Rich.

Speaker 1 (01:38):
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 air era of COVID,

(02:01):
I want to just start with you 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

(02:22):
like paint the picture like you were this, you know,
successful ad executive. You were like marketing acts, deodorant or
something like all sorts of things, 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?

Speaker 3 (02:47):
Yeah, I you know, I'd had a really fortunate time
in my career in advertising. I really enjoyed it. But
I think selling deodorant to teenage boys 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 want to do that, and I was

(03:09):
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. But it
was really that sense of unease that I had within

(03:30):
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 me meeting Andy, which then kind
of led on to Headspace.

Speaker 1 (03:43):
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 a
lot of people he loved dying unexpectedly, 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

(04:05):
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're in this global pandemic
filled with anxiety, pain and death. So now, as a

(04:27):
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. How do
you think this will reshape will reshape Headspace?

Speaker 3 (04:43):
Yeah, I think I think human suffering has been around
since 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 suffering
that we've had. You know, you mentioned that we start

(05:03):
We actually started off in the recession, like we've Andy
and 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,

(05:25):
and we've kind of started to see that happening. We've
started We thought that it would be in every school,
We thought that it would be part of healthcare 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, and you can't separate out
physical health and mental health like they're inextricably linked. And

(05:48):
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 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 kind of roadmap and our vision

(06:09):
way quicker than we could have ever expected.

Speaker 1 (06:11):
Yeah, it's interesting. I started covering tech back in two
thousand and nine, where as we were coming out of
the recession, and I think people don't understand that scarcity
and pain oftentimes breeds some of the most interesting innovation
and you see things that you know, in some of
these EDU cases become the center. So I'm interested to see,
you know, what the future of Headspace like, what is

(06:31):
the thing that now you guys are thinking about that
you weren't thinking about two months ago because.

Speaker 3 (06:37):
Of this Well, I think it's more just keeping up
with the demand. I think our strategy has actually stayed
the same. You know. The way that we think about
it is we think about like 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 like Headspace are actually an example of that, where

(06:58):
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, and technology is enable us 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

(07:20):
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.

(07:41):
And then also our kind of enterprise offering. You know,
we've got over seven hundred enterprises 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 has just accelerated it all. I mean, for us,
it's really about how do we keep up with the
demand as all of these things start to come towards

(08:02):
us a much quicker rate.

Speaker 1 (08:05):
And Headspace is also offering free subscriptions right to healthcare
workers and certain folks who are really on the frontlines
and who are dealing with some of these mentally very
stressful situations.

Speaker 3 (08:17):
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, but we
when covid launched, we extended our free product offering so
that anyone could get access to it in the weather
in the storm section, and then we made it free
for all healthcare professionals with the NHS. We parted in

(08:38):
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. And in France we partner
up with the Health Ministry in France as well. So yeah,
we tried to do as much as we can and
react as quickly as we could in the moment as
it happened.

Speaker 1 (08:57):
What do you think the future of work looks like?
I think about mental health than you know, and a
future where we're 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 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

(09:19):
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 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 try to shift

(09:41):
the workforce in a more isolated way.

Speaker 3 (09:45):
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 isn'table us
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. My wife crying, but my
young babies crying, you can't probably hear it. But like

(10:06):
that's the reality, and every single person situation is very different.

Speaker 4 (10:09):
You know.

Speaker 3 (10:10):
If I just take our team, there's people that live
by themselves. That's really tough. You know, we've just been
it's been announced it's probably going to you know, last
into September. We've actually told our team that they're not
going to come back to work until September. So there's
people on their own. There's people have got kids that
aren't going to have a school year. There's people that
have got family that live abroad, like all my families abroad,

(10:32):
you know, my mum's 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,

(10:53):
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 has enabled
us to work, but to be stuck on your computer
screen in and you know, in a not ideal environment
at home is not easy on his mental health. So
we definitely haven't worked it all out, and we're trying

(11:15):
to be as personalized with the team as possible, knowing
that every single person situation is very very different.

Speaker 1 (11:21):
Yeah, Twitter sit employees could work from home forever. Would
you ever consider that?

Speaker 3 (11:27):
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 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, and so
I think, and especially around creativity, I think there's ways

(11:49):
in which we can use space in a more thoughtful way.
But I think the way that we're going to work
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.

Speaker 5 (12:00):
I personally I would like it to be more of
an augmented and choice based kind of approach, which is
how we're thinking about it. Augmented as in what I think,
like as in I think there's opportunities to have creative
exploration and kind of coming together as a community in
real life, but giving people the choice that you know,

(12:22):
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 homeschooling,
which is super tough, but to have be there for
your young children I think for parents when we set
We've got a lot of parents in Headspace in particular,
and so we've set up a parents group.

Speaker 3 (12:42):
So there are things that I think are 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.

Speaker 1 (12:52):
I got to wrap it soon. So two quick ones.
The thing that sets Headspace apart that I've seen your
investors talk about is data driven approach. And you know,
using a data driven approach to meditation and mental health
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?

(13:15):
Does it project when we feel bad?

Speaker 2 (13:17):
Like?

Speaker 1 (13:17):
What does the future look like? Take us far into
the future.

Speaker 2 (13:21):
Sure.

Speaker 3 (13:22):
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
and 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

(13:43):
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'd have a very personal conversation and he would direct
you down a path to help you with the thing
that you wanted help the most with. We believe that
techology and data can recreate that. So how do we

(14:03):
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 digital interventions are the things that
you know, we want to build for the future.

Speaker 1 (14:23):
Last question. 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? I want to ask you that
question now, how much of your life now, do you
spend in the present moment versus then?

Speaker 3 (14:44):
Way more than I did then, but definitely not enough.
I think we would be the answer. I mean, it's
such a hard thing to be in the present moment
all the time, you'd being like you are. But definitely
I've seen I've seen huge improvements since i've practice, since I'm.

Speaker 1 (15:00):
Meet Andy, and your advice to people about living present
during this moment.

Speaker 3 (15:05):
I think for me, I think that's the best thing
that we can do because we do not know what's
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

(15:25):
is I think the most valuable skill that we can
all teach ourselves at the moment.

Speaker 1 (15:30):
Okay, we've got to take a quick break to hear
from our sponsors more as my guest. After the break,
my next interview is about the future of love. What

(15:52):
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 Isam Husseini, the
CEO of Match dot Com and Plenty of Fish CEO
Malgasha Green. Guys, I'm excited to be here with you guys,

(16:14):
even though I say be here, be socially distant and
on zoom. You both are at the forefront of online dating,
and obviously I think this is a moment where physical
touch is almost dangerous. So what strange circumstances we are in.
So I'm excited to be here to be chatting about this.

(16:36):
I would love for both of you separately take me
into the dating war room. Like it's March. The pandemic
is upon us, at least here in the United States.
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

(16:58):
and meet each other. What were those conversations.

Speaker 4 (17:00):
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

(17:21):
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 we were based to allow everyone to work from
home and closed our office pretty quickly at the beginning
of the pandemic and we've been able to work from

(17:44):
home pretty easily, so we're very lucky from that perspective,
and 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
up to engagement and usage on our platform, which was
extremely encouraging, and so we set in motion our plans

(18:09):
to accelerate the rollout of a live streaming feature that
we had been testing for the past few months.

Speaker 1 (18:17):
Sam, how about you, what were those conversation 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.

Speaker 6 (18:27):
This, Yeah, we didn't know what to expect, certainly, you know,
we haven't seen something like this before, although in my
twelve years at match we have seen quite a bit.
And one thing that we've seen is that love and
the desire to come meaning for connections with others, especially

(18:48):
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. 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 believe it or not, we're sort

(19:10):
of seeing a swing back to romance. Given like you said,
physical touch is off the table and those pressures are
lifted and we're all virtual dating now. We found that
folks are having more meaningful connections than as a return
to romance.

Speaker 1 (19:29):
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

(19:49):
to slow downs, Like how are you seeing virtual courtship
change in the coronavirus era?

Speaker 6 (19:56):
So we are seeing video getting much more adoption than
it has in the past before COVID nineteen. You know,
our data show that you know, mid single digits, five
to six percent of users were even interested in.

Speaker 3 (20:10):
Trying video dating.

Speaker 6 (20:13):
That number has jumped up to almost seventy percent 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 were feeling more
socially isolated. So we almost saw it was our responsibility

(20:36):
to do everything in our power, any tool that we
can we can roll out to help singles feel less isolated.
So that Match we've 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

(20:57):
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 sign Well.

Speaker 1 (21:10):
I mean it does feel like a look before. It's
a little weird to video chat on a dating app, right,
like there was a certain I would say, the 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 you seeing that, Malgosha, I know
Plenty of Fish also launched a video feature very early on.
I think you guys were one of the first to

(21:32):
do that. What was the thinking there and you know
what have you guys found?

Speaker 4 (21:37):
Yeah, Well, 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 facetiming with their family and they're having zoom calls

(22:00):
like this one, 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 to many and think of it 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

(22:21):
chat with one another, text chat and interact with the host,
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.

Speaker 3 (22:40):
Dating is expensive. You have to go out and you.

Speaker 4 (22:43):
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 streaming
feature as a way to really make it easier, lower
pressure way to meet people online from home. And so

(23:05):
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 in a short
amount of time. One in five of Plenty of Fish
members use the live streaming feature on a daily basis.

Speaker 1 (23:29):
And can you just explain it? So like, let's say
we're on it right now, how does that work?

Speaker 4 (23:34):
So there'll be one post and anyone could live stream,
So any member of 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, and other
people join the live stream and then just chat with

(23:56):
the streamer. 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 an audition to be your
date and It's been really phenomenal adoption because we've had.

Speaker 3 (24:19):
This was looking at the stats this last.

Speaker 4 (24:21):
Weekend alone, We've had twelve thousand matches a day. So
people are really connecting on video through this future are there?

Speaker 1 (24:30):
I mean, I'd be curious to know somean for you, like,
what do you guys think? I know that so many
folks are looking at live streaming like while they're home
in different ways. What do you think is the future
of video for online dating? Even in a post coronavirus world.

Speaker 6 (24:43):
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 addict after two short months. So
video is here to stay. And on Match, our platform
has always been around meaningful connect You come to Match
when you're looking for a real connection, and we found

(25:04):
that one on one video can be a great way
to as the name of the feature, vibe check implies,
just get to know if there's if the ViBe's there,
if this chemistry there, if there's a spark there before
you actually go on a first date. So in a
post pandemic world, we do I do see one on
one video playing a pretty pretty interesting role and a

(25:25):
great role, and one that can maybe replace the first date,
where a quick vibe check on the match app will
let you know if there's a spark there and whether
you should invest the time to go and have that
iril first date.

Speaker 1 (25:38):
This maybe goes into because there's always been AI and
algorithms to try to match us for good, but you
can't really replace chemistry, right.

Speaker 2 (25:45):
That's right.

Speaker 6 (25:45):
We've actually our members have told us that within ten
minutes of seeing someone on video they're able to tell
with this chemistry there, and ten minutes is a much
shorter amount of time to invest in going on a
full first date.

Speaker 1 (25:59):
Question for you, Malgochila. You know, as you think about
introducing live streaming, I got to put on my tech
and ethics hat. You know, how do we make sure
this doesn't turn into chat rolette 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

(26:21):
sex online to live streaming, people can behave poorly. So
how are you guys making sure that everybody's behaving?

Speaker 4 (26:30):
Great question, It's something that was certainly a huge concern
of mind when we started looking at the future, and
I feel pretty comfortable that we're addressing 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

(26:52):
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 recording feature. So if someone
feels uncomfortable with what's happening on the stream, whether the
nudity or any sort of you know, bad language, or

(27:16):
you know, anything illegal happening that clearly conflicts with our
very clear community guidelines. Everyone must review the guidelines before
opting into the future.

Speaker 3 (27:26):
UH.

Speaker 4 (27:26):
They the moderator step in right away. The person is
kicked out, and depending on the severity they even get
either get a warning or permanently banned from from the
future and from the platform.

Speaker 1 (27:37):
As you guys went into kind of building out this
new these new products and ways people can interact in
the pandemic era, are there features that you decided not
to implement 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

(27:57):
to do.

Speaker 4 (27:59):
So our face filter ban was unrelated. It was this
past fall. It was something that 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 your appearance in some way.

(28:22):
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 authenticity is
really important. So that's why we instituted the face filter
ban last fall. But to your question, I don't think
there's anything that we not pursue.

Speaker 6 (28:40):
I can I can maybe jump in. So we take
privacy very very seriously. One of the things that we've
decided to do, we decided really early on, is never
to monetize our members' data. So our business model is
completely different. Users paid to access more features and our platforms.
And to your point on privacy, you know, dating is

(29:01):
a pretty private matter and we want and when we
decided to not monetize any of the data that as we.

Speaker 1 (29:06):
Share with our platforms.

Speaker 3 (29:07):
This is then when I say our, I.

Speaker 6 (29:08):
Mean match employing of fish All being part of the
match root portfolio.

Speaker 1 (29:13):
Is there anything that's been really surprising to you about
how your users have been dating during this time and
adapting to 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?

Speaker 4 (29:28):
Yeah?

Speaker 2 (29:28):
Sure.

Speaker 4 (29:29):
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,
and right.

Speaker 3 (29:48):
Now that is definitely happening.

Speaker 4 (29:50):
And I think it speaks to something as all 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. You know, this slowing down and
more conversation and spending time getting to know one another
that really kills to them.

Speaker 1 (30:10):
How do you some 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

(30:30):
people are finally slowing down.

Speaker 6 (30:34):
One of the approaches that we've taken is to not
just relying on AI alone. Love is not some things
you want to leave in the hands of AI.

Speaker 3 (30:44):
I always say so.

Speaker 6 (30:45):
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 down

(31:09):
now that we have this team of experts at ways
where they can assist our members even more, and we
have sort of big plans I can't get into them
right now, but big plans down the road of how
AI plus human expertise can be the future of matchmaking
and online dating.

Speaker 1 (31:25):
Well, I'd be curious to know what that looks like
like a combination of like Her the movie Her.

Speaker 6 (31:32):
Not like Her. I think it's all around.

Speaker 1 (31:35):
How do how do singles.

Speaker 6 (31:37):
Find their match, the real match, not just rely on
AI and algorithms alone, and how experts and some human
intervention to help you turn the knobs and make sure
that you're focusing on the right things.

Speaker 1 (31:50):
Like you're being way too superficial kind of thing.

Speaker 6 (31:53):
For example, dating in the real world is never around
the checklist. You know, we sort of flex all the
time based on the chemistry and in person interactions that
we have. So we think that a human expert can
help guide member our members to focus on what's important.
And also with in combination of features like bibcheck where

(32:16):
you can sort of go beyond what's on paper, so
to speaker behind the screen and see someone face to face,
can get at the intangibles when it comes to finding chemistry.

Speaker 1 (32:26):
Well, last question, because you've got to wrap it. As
as the leaders of large companies responsible for our hearts
and dating, what have you guys learned about love?

Speaker 4 (32:35):
I think the main thing that I've learned through all
of this time in the pandemic is that love persevers.
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,

(32:56):
and it speaks to how important human connection is in
our lives and it really is an essential part of
our being.

Speaker 6 (33:05):
Echo that I don't think.

Speaker 2 (33:08):
You know.

Speaker 6 (33:08):
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, and we've seen it.

Speaker 3 (33:18):
Through this pandemic again.

Speaker 6 (33:20):
That our members have found a way to continue dating,
continue forming meaningful connections. And I heard about a match
couple who 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 just

(33:41):
them in the wild, and actually a real life a
bear was their ring bearer, believe it or not. So
examples like that we hear about all the time, and
we find that love is going to get through this
pandemic and anything else sort of be faced on the book.

Speaker 1 (33:57):
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 as my guest. After the break, my

(34:21):
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. Mollie 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

(34:43):
of the most infamous high stakes poker games in history.
It was an underground game attended by everyone from celebrities
to politicians, even members of the mob. Here's Molly. I'm
super excited to be doing this with you, just to
give you since I was in quarantine early in the

(35:05):
first movie I watched was Molly's Games, so I was
very excited when they said I would be chatting with
you 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

(35:25):
to La 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 famous politicians showing up.
You almost serve time in prison. I mean, you just
have such like a fascinating background. By the way, for

(35:45):
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.

Speaker 2 (36:02):
Kind of that kind of explain that to my parents
for you know, twenty years. Yeah, 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
as a Harvard educated cardiothrotic surgeon. My other brother is
a two time Olympian, also spent time playing in the NFL.

(36:25):
And I had this plan, right, it was going to
be law school and the Olympics, and something happened. You know,
I tripped on a stick. If you've seen the movie,
it's metaphor and reality. On my Olympic qualifier run, I
spied over this small little branch that caused my ski
to pre release and everything was derailed. So I think

(36:48):
I was primed for a bit of a rebellion. 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 was so compelling

(37:08):
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 it was super compelling to me, and
I wanted to stay in the room in the beginning
for the learning. You know, there was just so much

(37:29):
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

(37:51):
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 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 lare of it

(38:12):
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.

Speaker 1 (38:21):
And it's like you, I mean, it was high stakes
poker and you sew 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

(38:43):
the dark thing? Like what was the thing that like
brought people down? And you can give us names too
if you want.

Speaker 2 (38:51):
Unquestionably, the thing that brought people down was greed and
ego and getting out of a logical brain and into
an emotional brain to a mode of like seeking revenge
or seeking to prove something real, ego driven. The people
that consistently won and that did well were able to
stay composed. They were able to stay rational. They were

(39:13):
able to walk away when it wasn't their night, and
they were happy for the wins and were 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

(39:36):
of degenerate modes that are that are very ego driven
and greed driven and everything else falls by the wayside.

Speaker 1 (39:44):
Was there any after all of this? I mean, and
there's such a crazy story of you're almost you know,
you being arrested and this you know a lot of
the depend on you and you almost going to prison.
I mean, are there any scenes that stick with you
from those games? In 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

(40:07):
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?

Speaker 2 (40:18):
Yeah? For sure? I mean there are a lot of
scenes in you know, the the night that I saw
someone lose one hundred million dollars, was just you know,
how's this reality? And then how am I at the
center of this?

Speaker 1 (40:32):
Take me to that night? What happened?

Speaker 2 (40:35):
You know? It was a game that sort of lasted
over two nights, and there were a bunch of billionaires
in the room, and it was it was an incredibly
intense you don't come up for air thirty six hours
and someone walked away and had lost one hundred million dollars.

(40:56):
Another scene that will be forever ingrained and my mind
was when 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 loveling Colorado to

(41:19):
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 get here?
And I've had so many of those moments, and in

(41:42):
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
presidential suites and everybody knew my name at the high
end hotels, and I you know, bought a Bentley with
cash and like sort of that that that version of it,

(42:04):
and then it and then it got extremely dark and
and you know it definitely, uh, my life was in
ruins when it was all said and done. 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.

Speaker 1 (42:27):
You know, how do you think this moment? I don't
even know if this is an okay question, but like,
how is the game of Polka relevant to this moment
right now? Like it certainly seems like this is a
relatively high stakes moment that we are sitting in. We
were sitting in a moment of pandemic and race rights,
and it certainly seems like the steaks could not be higher.

Speaker 2 (42:49):
Yeah, you know, 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. And there are
those moments in a poker game, you know, you can

(43:11):
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 mean so much more than they have previously.
And I think that's where we are right now, and
it's really important to slow down and stay in that objective,
rational mind and not give in to fear and sort

(43:34):
of what the what the rest? You know, what what
the crowd is saying and all that, and and and
stay objective and stay within, you know, aligned with with
what you believe in and your morality, and and act
wisely because it really matters right now.

Speaker 1 (43:51):
When you had the FBI show up at your door,
when you thought you were going to be going away
for a long time, how did you what was your
head like, not a nice neighborhood to be in, Like
what take me into that neighborhood? And how did you

(44:11):
deal with the high states pressure of that of that moment,
Like what advice would you give to people in their
head like mentally dealing with that.

Speaker 2 (44:23):
I think you never know who you're going to be
until you get to a really big breaking point. Yeah,
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 to to make it work,
to battle back, to have redemption, to be part of redemption.

(44:47):
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 sort of
keep me in solution and in contribution. I think one
of the greatest tools I've ever found for that is meditation.

(45:08):
It really is extraordinary in training our mind to stay
focused and stay sort of out of the lower brain,
the amygdala stuff. And then you know, I think the
other thing is is that we can instead of acting
on fear, we can act contrary to fear, which is

(45:29):
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. So
I think it's just not giving in to these sort
of instincts or these demands and continuing to go high,
continuing to go high, continuing to like overcome limitations. But

(45:54):
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. It's just a
matter of continuing to fight the good fight.

Speaker 1 (46:12):
I think, you know when 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

(46:35):
as this, you know, kind of like crazy woman who
was like this, 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
you fought to change the narrative, and you actually sought
out Aaron Sorkin, who, for folks who don't know, is

(46:57):
like a famous director. He was did social network that
you fought to change your story or to have your story.

Speaker 2 (47:05):
Told in a dimensional way.

Speaker 1 (47:08):
In a dimensional way, why what was the misconception about you?
And tell me about what you told Aaron Sorkin.

Speaker 2 (47:15):
Okay, 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,
who were her romantic endeavors, and sort of like the
manipulative nature of it. And you know, I built a

(47:40):
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 I knew that
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 that's just as important to

(48:01):
include as as but I wanted a full and balanced picture,
and I really believed that if I could tell that story,
there would be that could be a springboard to a
second chance. And yeah, no one wanted to touch this movie.
Everyone said, there's so many powerful people in d C,
LA and New York that will never let this get made.

(48:21):
And everyone was terrified. And I said, you know, I'm
going to just go straight to the top of my
favorite writer in the world and see if he might
be interested. And 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 you know, he

(48:42):
went into the meeting thinking, I'll take this meeting as
a favor to a friend, but I'm not so interested
in this 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

(49:03):
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 and that's what I was so happy that he
recognized and felt passionate about about writing and directing.

Speaker 1 (49:23):
I've gotta I've got to stop it, 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?

Speaker 2 (49:37):
Ironically, I was a pretty uh fearful kid. 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. And
so it's in it's in that practice of Okay, this

(49:58):
scares me. I'm just gonna, you know, take a deep
breath and twenty seconds of courage. I'm going to walk
in and see what happens.

Speaker 1 (50:17):
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 zo NF dot com and
for more from dot dot dot sign up for our
newsletter at dot dot dot media dot com Backslash Newsletter.

(50:39):
We'll be launching it soon. First Contact is a production
of Dot dot Dot Media executive produced by Lori Siegel
and Derek Dodge. This episode was produced and edited by
Sabine Jansen and Jack Reagan. The original theme music is
by Xander Singh. First Contact with Lori Siegel is a

(51:14):
production of Dot Dot Dot Media and iHeartRadio
Advertise With Us

Popular Podcasts

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

The Clifford Show

The Clifford Show

The Clifford Show with Clifford Taylor IV blends humor, culture, and behind-the-scenes sports talk with real conversations featuring athletes, creators, and personalities—spotlighting the grind, the growth, and the opportunities shaping the next generation of sports and culture.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.

  • Help
  • Privacy Policy
  • Terms of Use
  • AdChoicesAd Choices