The High-Stakes of Going All-In
Conversation with Molly Bloom
Entrepreneurship is not a skill, it’s a mindset and nobody defines this mindset better than Molly Bloom.
Molly started her career as an athlete. Despite suffering from a medical condition when she was 12 that did not allow her to ski anymore, she ended up being ranked #3 overall in North America and made it to the Olympic qualifiers. At the qualifiers, she injured herself and decided to retire from skiing. Wanting a break from the cold weather after retiring, she decided to move to Los Angeles for a year.
In Los Angeles, she worked many jobs including being a waitress, cocktail waitress and an executive assistant. While working as an executive assistant, her Manager put her in-charge of being a waitress at a weekly poker game he used to run. This poker game was frequented by some of the most powerful celebrities, athletes, Wall Street titans and CEOs in the world. Regulars of the game included people like Leonardo DiCaprio, Tobey Maguire, Ben Affleck and Matt Damon.
Apart from just money, she recognised the opportunity that being in that room gave her — enabling her to have access to a network with information and power. She used poker as her trojan horse into the highest levels of business and society. She learnt everything about the game and used her observation to create an experience that was unparalleled. Within 8 months, she went from being a waitress at that game to running the game. As a 22 year old, she went up against the Billionaire Boys Club and won by asking them to abandon her Manager’s game, and to play in hers instead.
After a few years of running the game, in 2008, at the peak of the Financial Crisis she lost the game to Tobey Maguire. Instead of giving up hope, she decided to go bigger. She treated the poker game as a startup, where she then scaled it up from an initial buy-in of $10,000 to $250,000, and pivoted by moving to the East Coast. By the time she was 26 — she was running the biggest, richest and most infamous underground poker game in the world. To ensure this time that she would not lose the game, she became the owner, operator as well as, the bank for the game extending credit to the players.
It was also during this time she ran into trouble. Without her knowing, some of the players in the game were actually members of the Russian mafia. She also started using substances to be able to keep up with her lifestyle. This resulted in her being arrested by the feds and them seizing all her assets (worth over $5 million). At that point, they offered her a deal. She had the option of getting all her money back and having no criminal record if she handed over the hard drives that had information of all the games. Despite the risk of losing all her money and her freedom, she did not give up the information because it would impact so many careers, families and children. Although her judge was merciful and she did not go to prison, she did lose all of her money.
At 35 she was broke and moved back in with her parents. At that point, she took a step back and viewed herself as a startup in need of a rebrand. She knew her story was the monetizable asset she had, and wrote a book so she could own the IP for it. She wanted it to be made into a movie and used a data-driven approach to reach out to writers. Most of all, she wanted Aaron Sorkin (writer of Moneyball, Social Network and The Trial of the Chicago 7) to write her story. After asking every lawyer and agent for an introduction to Aaron Sorkin, she was able to meet with him and pitch her story. He agreed to write the story and direct it. In 2017, the movie came out and in 2018 it got nominated for an Oscar.
Since then, Molly has been a very sought after speaker travelling the world and sharing her story. Going from an Olympic-class skier to the operator of the largest underground poker game to the subject of an Oscar-nominated movie — she has always gone all-in, in what she does and has lived a bigger life in every decade of her existence than most people ever live.
I had the opportunity of speaking to her and learning more about her thought process behind being able to execute at a level that is the best in the world regardless of what she takes up. In this interview, she also talks about the importance of mindfulness and tools she uses to control her mind. She also discusses what an entrepreneurial mindset means to her, growing her business during a recession and what she’s working on next.
So you went from being an Olympic-class skier to the operator of the largest underground poker game in the world. You then pitched your story to Aaron Sorkin, the best screenwriter in the world, and the movie ended up getting nominated for an Oscar. What do you think differentiates your vision and execution, where you’re able to really go from being a beginner to the best in the world at everything you pursue?
First and most foundational is this willingness to work on cultivating a mindset that’s really resilient, which allows you to shift out of less productive states. Because you cannot control for obstacles in the world — you can’t control whether you were born with money or connections, but what you can do is, you can start to have real power and agency over how you navigate through everything. In my opinion, this starts and ends with your mind.
That’s why I talk a lot about how important a meditation practice is to me, because it allows me to override states of fear, states of doubt, states of wanting to give up, burnout, and manually change the narrative internally. And we know that thoughts correspond to actions and so, working on your mind allows you to have this threshold for discomfort. This allows you to take the action over and over again, until you get to where you wanted to go. So 100% first and foremost, foundational for me is the mind and doing some sort of daily practice of mind training.
Another thing I’m a big believer in, which I realised when I got to some of those more prestigious worlds, is that it’s not always or even most often the most talented person that rises to the top — it’s the person that keeps showing up. So that means, you can start from wherever you are and get there if you’re just willing to keep pushing the envelope.
Another factor that I’m big on is vision and strategy. Visualisation is something that I learned in my sports background and I think it’s really useful. I don’t think it’s the only thing because manifesting without action never works. What I do is this sort of visualising where I think about where I’m gonna take this thing that i’m working on and honestly, sky’s the limit. I constantly think about how big it’s going to be and a lot of times when you spend so many hours building something or thinking about something and visualising, and then it happens, it’s kind of like déjà vu because you’ve seen it so many times in your mind. But, there’ve also been things that I couldn’t see in my mind necessarily, and was still able to bring to fruition. But it’s a great skill if you can use visualisation.
Then before I execute something, I do a lot of due diligence, I do a lot of inquiry and I do a lot of research. I also think about things from as many different micro-angles as I can with a particular focus on the psychology of human beings that are in that world. I try to understand as much as I can about what’s going on in their world and their mind, before creating a vision and a strategy. From there I take the mental dexterity, resistance and threshold for discomfort that I’ve developed and just really move into things, whether that’s building a business or anything else.
In terms of building a business, there were several points in your life when you viewed different things as startups — the games and then your life story. From your experience, what do you think really comprises an entrepreneurial mindset?
I think it comprises of a willingness to be in the dark in the beginning and have no idea where you’re going and still go. You have to be relaxed in that uncertainty and to just believe that with sustained effort, it’s gonna work out. It’s also liberating yourself from perfectionism, learning how to fail gracefully even if there’s no such a thing as back up and just kind of conditioning yourself to have tolerance for it. I also think being an entrepreneur is all about learning your universe and figuring out where you can be a bit disruptive, or where you can bring in something that hasn’t been done before, considering all the angles while also being able to take calculated risks.
Apart from that, again it’s a lot about developing a threshold for discomfort, and being able to overcome these uncomfortable states of mind to continue going. This was something I learnt from my dad, which he called constructive suffering, and it’s the only way to get anywhere. There are very few people that just put in very little effort and make their life work and so just getting to this place where you have a threshold for discomfort helps you to build an entrepreneurial mindset.
And lastly, it’s about dissecting things to their fine parts so that you can understand them, and then understand how you can be different or be able to create something valuable in a unique way. I’m not somebody who just has ideas in a vacuum, it’s always looking at what the contents of my universe look like, getting involved, showing up and then being like okay, I can kind of see this angle to do it differently or I think we’re underutilizing this strategy. So for me, it’s just kind of like being a yes person (being willing to say yes), having lots of adventures, having things not work out and not being on a linear path. It’s got to get your head messy.
So for me, it’s just kind of like being a yes person (being willing to say yes), having lots of adventures, having things not work out and not being on a linear path. It’s got to get your head messy.
Outside of the individual building the business, another thing that always plays a huge role is the macro environment. When you lost your game in LA, it was right in the middle of a recession but you still went ahead and actually went bigger. What was your thought process then?
I think that it’s easy to get overtaken by the tide of negativity when markets are down, when recessions are in place or when world pandemics are influx. I think it’s important to understand the world that you’re living in, but also to not let it limit you. It obviously depends on industries and there are times when you should scale back, but for me, I believed then that there were people in my industry that were still financially okay and wanted an escape from what was going on in the world. Through these games, I was able to create that experience for them. And truthfully, at the time I did not think of it like it’s a recession and I’m going to go bigger because of that — it’s just that I was desperate because I had lost the LA game. I was full of spitfire and wanted to prove that I wouldn’t go down like that. I just muscled through, which was a great lesson because if I would have listened to what was going on in the cautionary tale of the markets and the world of finance, I wouldn’t have even tried. But because I was just so determined to stage a comeback, I powered through and it taught me that we have to be really careful to not completely get absorbed in the doom and gloom of the turbulence of the world, and instead maintain our own steady path.
And what are you working on now?
I think gaming and social experiences are a very underutilised technology in changing human behaviour. And so I’m in the process of establishing the first asset that’s going to come out of a gaming studio, that basically attempts to use an in-app currency in a social form and gamification to help people change behaviour. This would help people engage in activities that result in them being happier and create a sense of well being. I know that with self-help people just continually fall short of the motivation and so my vision is to build products in the mental-health and self-help industry for adults, kids or people who are in a place of need.
I did a lot of internal suffering in my 20s and 30s. I was able to accomplish things and be ambitious, but internally I was not well and paid a big price for it. And then I did a deep dive investigation into neuroscience, neurophysiology, biology, psychology, Buddhism, meditation, the 12-step program, and all these different protocols which helped me to learn how to completely shift and rewire what was happening inside my brain. From there, not only was I happier and not suffering, but I was also able to move more seamlessly through business and become much more productive. And so I believe that it’s my calling and I want to share these things. I see what exists in the market right now in terms of the books and the courses but these are only working for some people. There’s still a big part of the population that it’s not working for and so I want to use my experience in storytelling and movies, media, gaming and finance to address that gap in the market.
What is the most important tool that you’ve found that helps in improving human behaviour?
Meditation is a huge quantifiable practice, and by quantifiable I mean there’s a ton of hard science to validate the benefits of meditation and what it can do for your brain. It is scientifically backed that meditation drastically helps to increase your ability to focus and your ability to overcome lower mind states that hamper productivity, or cause unhappiness and discontent.
I think it is really important for ambitious and successful people to pursue well being and emotional regulation as heartily as they pursue business. This is because the benefits are just so massive for not only enjoyment of life, but also for truly being able to embrace risk and uncertainty in a business sense. Many of the things that hold people back or that get people into trouble in business are these unresolved issues that I think we as human beings, if we are steadfast and we’re really committed to it, can resolve and give you a completely different experience.
Personally, I also have a very overactive mind and it was always very hard for me to sit still. I didn’t think I could meditate at all and I used to keep getting angry when I would read that meditation was the solution. What I did was that I started really small with 30 seconds on the first day and then built on that. So at least until my app comes out, I recommend the app Headspace for people who want to start a meditation practice.
And lastly — I’m always very interested to learn more about how entrepreneurs in the US view Asia. So what is your perception on Asia in terms of whether you see it as a market with opportunities at the moment?
I think Asia probably has the most compelling opportunities right now. If I was younger and not so tired 😝, I would be really excited to check out what’s happening in Asia. It’s not what I’ve been focused on right now but I know that there’s huge opportunities. If I were in finance at the moment, that’s where I’d be looking. Also as someone focusing on gaming, I definitely also see a lot of opportunity in the Asian market for gaming.
