Episode 27: The Future of Mindfulness, Love… and High-Stakes Poker

Read the transcript below, or listen to the full interview on the First Contact podcast.

First Contact with Laurie Segall is a production of Dot Dot Dot Media and iHeart Radio.

Laurie Segall: Take me to that night, what happened?

Molly Bloom: 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 an incredibly intense you don’t come up for air, 36 hours. And someone walked away and had lost $100 million. 

Hi Guys, 

Welcome to another bonus episode of First Contact. This time it’s a three for one – you’re going to hear three quick interviews I recorded as part of the Collision Conference’s 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 Pierson. 

I’m Laurie Segall, and this is First Contact.

Laurie Segall: Rich, it’s good to be with you, although we were just saying as we were getting started, what strange circumstances we are in. But you are a very fascinating person to talk to during this time, because I think Head Space, it’s always seen a lot of value, but I think probably increasingly so in this environment. Before we get into Head Space in the era of COVID, I want to just start with you, and you personally. You were a successful ad executive um 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? You were this you know successful ad executive, you were marketing Axe Deodorant or something, all 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?

Rich Pierson: Yeah. 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 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 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 onto Head Space.

Laurie Segall: 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 it, 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. So now as a leader many, many years later of a company that looks at this, and whose companies almost I would say it had a birth out of these ideas, how do you think this will reshape Head Space?

Rich Pierson: Yeah. I think, look, 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 disconnected all the time, and I think that has had a very different effect on the type of suffering that we’ve had. You mentioned that we actually started off in the recession. Andy and I met at the end of 2008 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 in four or five years time, it would be in every single conversation, in every single boardroom. And we’ve kind of started to see that happening. 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. 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 just brought it into the mainstream in a much faster kind of way. And so, we’ve always believed that that’s a huge problem that we wanted to solve. I think it’s just accelerated our road map and our vision way quicker than we could’ve ever expected.

Laurie Segall: Yeah. It’s interesting. I started covering tech back in 2009 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 edge cases become the center. So I’m interested to see what the future of HeadSpace, what is the thing that now you guys are thinking about that you weren’t thinking about two months ago because of this?

Rich Pierson: 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 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’ve never have dealt with before. And I think platforms like HeadSpace are actually an example of that, where people come to us for things that they would’ve 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 has enabled us to scale that in a way that we would’ve never been able to before. We believe that you know mental health is going to have to be absolutely at the center of healthcare systems, and we’re seeing that as we work with more and more healthcare systems, especially in the US. We’re actually providing um 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 we’ll be releasing at the end of this year. And then also , kind of  our enterprise offering. We’ve got over 700 enterprises on that platform, and so all of those things, we’ve been working on those for years. Ever since we started, that’s been a kind of dream and a vision. I think this time has just accelerated it all. And for us, it’s really about how do we keep up with demand as all of these things start to come towards us at a much quicker rate.

Laurie Segall: Um and Head Space is also offering free subscriptions, right? To healthcare workers and certain folks who are on the front lines and who are dealing with some of these mentally very stressful situations.

Rich Pierson: Yeah. We always had our nose on a social impact lens which is to make it free for teachers K-12, but when COVID launched, 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 with the NHS, if you live in the UK, if you’ve got an NPI number in the US. So if you know healthcare workers and they’re struggling, please let them know about it. Um and um in France we’ve partnered up with the health industry in France as well. So we tried to do as much as we can and react as quickly as we could in the moment as it happened.

Laurie Segall: What do you think the future of work looks like? I think about mental health, and you know 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? First of all, be honest with us because everyone I’m a little over everyone saying that it was completely seamless and that we’re all experts in working from home. We had issues setting this thing up. So like lets can we just be completely honest? Be honest as a leader, because you’re in the forefront. What are some of the challenges you faced as someone who is 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 the workforce in a more isolated way?

Rich Pierson: I mean, I’d love to meet the leaders that found it seamless and it was easy. I think, yes we might have had technology in place that has enabled us to do this. That’s one thing. I think the human element of it is very, very different. I’m in my bedroom at the moment. I can hear my wife and my young baby’s crying. You can’t probably hear it, but that’s the reality. And every single person’s situation is very different. You know if I just take our team, there’s people that live by themselves. That’s really tough. It’s just been announced it’s probably going to last into September. We 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 who have got kids who aren’t going to have a school year. There’s people that have got family that live abroad. All my family is abroad. 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? And 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 Day. 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 their computer screens, because we’ve just found that, ya technology’s enabled us to work, but to be stuck on your computer screen in not an ideal environment at home, is not easy on people’s 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’s situation is very, very different.

Laurie Segall: Yeah. Twitter said employees could work from home forever. Would you ever consider that?

Rich Pierson: I think we’re definitely thinking what does the future of work look like? I definitely don’t think it’s going to be 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, 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 has changed forever. I really don’t believe that it’s going to go back to the way it was before. But 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.

Laurie Segall: Augmented as in?

Rich Pierson: I think like as in I think there’s opportunities to have creative exploration and 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. One of the best things, I think, beside the homeschooling which is super tough, but to be there for your young children I think for parents, we’ve got a lot of parents at Head Space in particular. And so, we’ve set up a parents group. And so, there are things I think that are really positive, but there’s things that are difficult with it. So how we augment those things to make it work for everyone I think is the way we’re going to try and approach it.

Laurie Segall: I’ve got to wrap it soon, so two quick ones. The thing that sets HeadSpace apart that I’ve seen your investors talk about is this 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 does it  predict when we feel bad? What does the future look like? Take us far into the future.

Rich Pierson: 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 of 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 at Head Space 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’d 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 believed that technology 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 where data is incredibly private, and that people have the choice to kind of opt into that. They’re the things that we’re really excited about. So kind of personalized medicine through these digital interventions are the things we want to build for the future.

Laurie Segall: 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?

Rich Pierson: Way more than I did then, but definitely not enough, I think would be the answer. I mean, it’s such a hard thing to be in the present moment all the time. But definitely I’ve seen huge improvements since I’ve practiced since I met Andy.

Laurie Segall: And your advice to people about living present during this moment?

Rich Pierson: I think for me, I think that’s the best thing that we can do, because 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, 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.

Ok we’ve got to take a quick break to hear from our sponsors, more with 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 Hesam Hosseini the CEO of Match.com and Plenty of Fish CEO Malgosia Green.

Laurie Segall: Guys, I’m excited to be here with you guys, 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. 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 and meet each other. What were those conversations like?

Malgosia Green: 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 where we’re 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 home pretty easily, so we’re very lucky from that perspective. 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 in engagement and usage on our platform which was extremely encouraging. And so, we set in motion our plans to accelerate the roll out of a livestream feature that we had been testing for the past few months.

Laurie Segall: Hesam, how about you? What were those conv-  I mean, were you nerv-  it certainly seems like the business could be under attack, like people aren’t actually going to be able to meet. What were the hard conversations like at the beginning of this?

Hesam Hosseini: Yeah. We didn’t know what to expect. Certainly we haven’t seen something like this before. Although in my 12 years at Match, we have seen quite a bit. And one thing that we’ve seen is that love and the desire for meaningful connections with others, especially for singles, is really strong. And that’s bore out. We see that during the pandemic. Singles are still looking for a meaningful connection. And like Malgosia 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 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 and there’s a return to romance.

Laurie Segall: Yeah. How are you seeing people adapting to virtual courtship? I mean, we all knew … I mean, by the way before, and I’ve interviewed dating app founders from the beginning of the time they launched these apps, and the biggest problem was 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 down. It’s like how are you seeing virtual courtship change in the Coronavirus era?

Hesam Hosseini: So we are seeing video gain much more adoption than it has in the past. Before COVID-19, our data showed that mid-single digits, five to six percent of users were even interested in trying video dating. That number has jumped up to almost 70% now during the pandemic. And so at Match, we pivoted fairly quickly. 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 as our responsibility to do everything in our power, any tool that we can roll out, to help singles feel less isolated. So at 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. It’s a feature that before these times we felt would’ve had lower adoption. And it’s been a great tool for members to stay connected and actually continue dating, and continue feeling that feeling a meaningful connection through this app.

Laurie Segall: Well I mean, it does feel like before it’s a little weird to video chat on a dating app, right? There was a certain I would say stigma. I mean I just say there’d be a certain stigma to doing that, but something about this pandemic has changed that. Are you seeing that Malgosia? 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 what have you guys found?

Malgosia Green: Yeah. To your point, I think people have very quickly gotten used to video. We ran a survey about a month ago and found that 75% 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 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 feature, just to explain a little bit what it is, it’s quite different than 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 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. Dating is expensive. You have to go out, and you pay, and it’s not only 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, or elderly parents, and it’s really tough to get out and meet people. So we started looking at the livestreaming feature as a way to really make it easier, a 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 feature has been phenomenal. In a short amount of time one-in-five of Plenty of Fish used the livestream feature on a daily basis.

Laurie Segall: Can you just explain it. So like let’s say we’re on it right now. How does that work?

Malgosia Green: So there will be one host, and anyone can live stream. So any member at 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 they just chat with the streamer, and then we have a couple of really great features. 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 and audition to be your date. And it’s been really phenomenal adoption because I was just looking at the stats this last weekend alone, we’ve had 12,000 matches a day. So people are really connecting on video through this feature.

Laurie Segall: Are there — I mean I’d be curious to know, Hesam for you, what do you guys think? I know that so many folks are looking at livestreaming 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.

Hesam Hosseini: 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 at it after two short months, so video is here to stay. And on Match, our platform has always been around meaningful connections. You come to Match when you’re looking for a real connection. And we found out one-on-one video can be a great way to, as the name of the feature Vibe Check implies, just get to know if the Vibe’s there. If there’s chemistry there. If there’s a spark there, before you actually go on a first date. So in a post-pandemic world, I do see one-on-one video playing a pretty, pretty, interesting role, and a 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 IRL first date.

Laurie Segall: This maybe goes into because there’s always the AI and algorithms to try to match us, but you can’t really replace chemistry, right? I mean, and sometimes-

Hesam Hosseini: That’s right. Actually our members have told us that within 10 minutes of seeing someone on video, they’re able to tell if there’s chemistry there. And 10 minutes is a much shorter amount of time to invest than going all out on a full first date.

Laurie Segall: Question for you, Malgosia, as you think about introducing livestreaming, I’ve got to put on my tech and ethics hat, how do we make sure this doesn’t turn into chat roulette to some degree? 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 livestreaming people can behave poorly. So how are you guys making sure that everybody’s behaving?

Malgosia Green: Great question. It’s something that was certainly a huge concern of mine when we started looking at the feature. 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 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. There is a very prominent reporting feature, so if someone feels uncomfortable with what’s happening on the stream, whether it be nudity, or any sort of bad language, or anything illegal happening that clearly conflicts with our very clear community guidelines, everyone must review the guidelines before opting into the feature, the moderators step in right away. The person is kicked out and depending on the severity they either get a warning, or permanently banned from the feature and from the platform.

Laurie Segall: As you guys went into building out 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. Privacy or … are there certain things you guys decided not to do?

Malgosia Green: 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 hiding what you look like, or accentuating your appearance in some way. That’s 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’ve not pursued-

Hesam Hosseini: I can maybe jump in. 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 model is completely different. Users pay to access more features on our platforms. And to your point on privacy, dating is a pretty private matter. And we decided to not monetize any of the data that is being shared on our platforms. And when is say our I mean Match, Plenty of Fish, all being part of the Match Group portfolio.

Laurie Segall: Is there anything that’s been really surprising to you about how your users have been dating during this time and adapting? 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?

Malgosia Green: Yeah. Sure. I think one of the most surprising things that we’ve seen is just much higher engagement from women. So women have been participating at higher rates, and this is fantastic, because is 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 now, that is definitely happening. And I think it speaks to something Hesam 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 this slowing down and more conversation, and spending time getting to know one another, that really appeals to them.

Laurie Segall: How do you code romance, right? 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 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?

Hesam Hosseini: One of the approaches that we’ve taken is to not just rely on AI alone. Love is not something that you want to leave in the hands of AI I always say. 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 the marriage of sort of the  human expertise along with AI is really the answer. And we are looking at ways, now that we have this team of experts, have ways where they can assist our members even more. And we sort of have big plans. I can’t get into them now, but big plans down the road of how AI plus human expertise can be the future of matchmaking and online dating.

Laurie Segall: Well, I’ll be curious to know what that looks like. A combination of like Her, the movie Her?

Hesam Hosseini: Not like Her. It’s all around how do singles find their match, their real match, but 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.

Laurie Segall: Like you’re being way too superficial kind of thing?

Hesam Hosseini: For example, dating in the real world is never around a checklist.

Laurie Segall: Sure.

Hesam Hosseini: 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 our members to focus on what’s important, and also in combination with features like Vibe Check, where you can go beyond what’s on paper so to speak, or behind the screen, and see someone face to face, can get at the intangibles when it comes to finding chemistry.

Laurie Segall: Well, last question because we’ve got to wrap it. As the leaders of large companies responsible for our hearts in dating, what have you guys learned about love?

Malgosia Green: I think the main thing that I’ve learned through all of this time in the pandemic is that love perseveres. We have heard from our singles, the majority of singles, almost three-quarters, are hopeful that they are 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 being.

Hesam Hosseini: I’d echo that. I don think you know I was around at Match in 2008 when the last recession hit, and we found out then that love was recession proof. And we’ve seen it through this pandemic again, that our members have found a way to continue dating, continue forming meaningful connections, and I’ve heard about a Match couple who was supposed to get married during the pandemic. They were nature enthusiasts, and they had to cancel their big Alaska wedding. But the two of them went to the animal sanctuary and had their wedding. Just them in the wild, and actually a real life 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 go through this pandemic, and anything else we face down the round.

Laurie Segall: I like that. Love is recession proof and pandemic proof.

Ok we’ve got to take a quick break to hear from our sponsors, more with 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 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 poker games in history – it was an underground game attended by everyone from celebrities to politicians. Even members of the mob. Here’s Molly.

Laurie Segall: Molly, I am super excited to be doing this with you. Just to give you a sense, I was in quarantine early and the first movie I watched was Molly’s game, so I was very excited when they said I would be chatting with you.

Molly Bloom: Amazing

Laurie Segall: So just go right in. Just to give folks a sense who have not seen the movie, who don’t know your background, nearly qualified for the Olympics before an injury that changed all your plans. Moved 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 served time in prison. I mean, you just have such like a fascinating background. By the way, for folks who haven’t seen the movie, there’s just so much heart and nuance involved, too. So you just can’t … it’s such a fascinating story. Let’s just start with how did you go from Olympic hopeful to like underground poker? How did that happen?

Molly Bloom: I’ve been trying to tell that to my parents for you know 20 years. You know  I grew up in this very high-achieving family. In my family, 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 spent time playing in the NFL. 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 a metaphor and reality, on my Olympic qualifier run I skied over this small little branch that caused my ski to pre-release, and everything was derailed. So I think 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 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 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, my plan was get in, create this network, make a bunch of money, and then get out. But that’s not how it worked. But you know that was lure of it in the beginning and the preconditions to why I was so amenable to kind of  falling down this rabbit hole and saying yes.

Laurie Segall: And it was high stakes poker. You saw some of the most powerful people in the world in these addictive high moments. What made a great poker player, and what was like, and you can even get specific with this, now we’ve like opened the doors on it, what was the dark thing? What was the thing that brought people down? And you can give us names, too, if you want.

Molly Bloom: Unquestionably the thing that brought people down was greed and ego, and getting out of a logical brain and into an emotional brain, into 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 able to walk away when it wasn’t their night. And they were happy for the wins, and and were able to let go of the losses. So so much of poker and so much of life is about this 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 very ego driven and greed driven, and everything else falls by the wayside.

Laurie Segall: Was there any, after all of this, I mean, and there was such a crazy story of you almost you know being arrested, and all of this pinned 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 were moments that you saw people at their highs and their lows. But are 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?

Molly Bloom: Yeah. For sure. I mean, there are a lot of scenes. You know the night that I saw someone lose $100 million was just how’s this reality? And then, how am I at the center of this?

Laurie Segall: Take me to that night, what happened?

Molly Bloom: 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, 36 hours. And someone walked away and had lost $100 million. Another scene that will be forever ingrained in my mind was when the sort of hit man for the Italian mob came to my apartment, and stuck a gun in my mouth, and ordered me to and basically insisted that I give them a piece of my operation. You don’t get from good girl from Loveland, Colorado, to taking on the mob, and breaking the law, and running the biggest gambling enterprise overnight. 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 I get here?” And I’ve had so many of those moments. In the beginning, there are moments that play out like a movie scene. I was 24 years old and all of a sudden had all this money and all this power, and you know I’d 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 that version of it. And then it got extremely dark you know it definitely my life was in ruins when it was all said and done. But there were, there were moments in both of those categories in, “Oh my gosh, look what I created from nothing,” and then, “Oh my gosh, look what I created.” You know?

Laurie Segall: Yeah. How do you think this moment, I don’t know even know if this is an okay question, but like how is the game of poker relevant to this moment right now? It certainly seems like this is a relatively high stakes moment that we are sitting in. We are sitting in a moment of pandemic, and race riots, and it certainly seems like the stakes could not be higher.

Molly Bloom: 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 right now mean more than they’ve meant for a long time. And there are those moments in a poker game. You know it’s friendly, it’s friendly, people play, and then all of a sudden there’s a huge pot and everything matter, 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 into fear, and sort of what the rest of- what the crowd is saying, and all that. And stay objective, and stay within and aligned with what you believe in and your morality, and act wisely. Because it really matters right now.

Laurie Segall: 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?

Molly Bloom: Not a nice neighborhood to be in.

Laurie Segall: Take me into that neighborhood, and how did you deal with the high stakes pressure of that moment? What advice would you give to people in their head mentally dealing with that thing?

Molly Bloom: I think you never know who you’re going to be until you get to a really big breaking point. 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 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 keep me out of fear and that sort of keep me in solution, and in contribution. And I think one of the greatest tools I’ve ever found for that is mediation. It really is extraordinary in training our mind to stay focused and stay out of the lower brain, the amygdala stuff. And then, I think the other thing is, is that we can instead of acting on fear, we can act contrary to fear, which is be of service. Do the things that scare you, that can make you part of this larger solution in the world, do yourself, whatever it is. So I think it’s just not giving in to these instincts or these demands, and continuing to go high. Continuing to go high. Continuing to overcome limitations, but I mean I just 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 this rosy disposition. That’s not how it was at all. It’s just a matter of continuing to fight the good fight, I think.

Laurie Segall: You know when a lot of I think where a lot of people looked at you in a different way was after Molly’s Game, right? This movie that came out that shed a different light on you, that showed you in a more nuanced way, that when your story initially came out, not to go full on but you were made out to be a certain way-

Molly Bloom: For sure.

Laurie Segall: … in the tabloids as this kind of like  crazy woman who was this evil I mean, I’m saying it-

Molly Bloom: No. For sure. 100%.

Laurie Segall: 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 a famous director. He did Social Network. But you fought to change your story.

Molly Bloom: I did.

Laurie Segall: Or to have your story told-

Molly Bloom: In a dimensional way.

Laurie Segall: … in a dimensional way. Why? What was the misconception about you, and tell me about what you told Aaron Sorkin?

Molly Bloom: 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 I built 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 I knew that I needed to 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 include, but I wanted a full and balanced picture, and I really believed that if I could tell that story, 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 DC, LA, and New York that will never let this get made, and everyone was terrified. And I said 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 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 stories of our lives in a balanced way, in a dimensional way, 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 we get to be human beings, you know and that’s what I was so happy that he recognized and felt passionate about writing and directing.

Laurie Segall: I’ve got to stop it, but I’m going to 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?

Molly Bloom: Ironically I was a pretty 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 that practice of okay, this scares me, I’m just going to you know take a deep breath and 20 seconds of courage, I’m going to walk in and see what happens.

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 CONF – THAT’S C-O-N-F – DOT COM. And for more from Dot Dot Dot, sign up for our newsletter at dotdotdotmedia.com/newsletter. We’ll be launching it soon.

First Contact with Laurie Segall is a production of Dot Dot Dot Media and iHeart Radio.