Molly's Game: From underground high-stakes poker to finding redemption
TQD: Issue 12
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In this issue:
Quest Minutes - key takeaways and timestamps from our episode with Molly Bloom:
Ran underground high-stakes poker games for Hollywood celebrities, pro athletes, and wealthy elites
Author of Molly’s Game, adapted into the Oscar-nominated film of the same name
How did Twitch manage to rake in $1 million per month in revenue?
Weekly AMA with Justin - JK will answer your burning questions every week right here on The Quest Digest - keep reading to find out how you can get your questions answered and be featured on our newsletter!
♠️ Quest Minutes: Molly Bloom
Catch the full conversation here:
Molly’s Game:
Molly Bloom has done it all - from becoming an Olympic level professional skiier, to running some of the biggest high-stakes poker games in the world with your favourite Hollywood stars. If you’ve read her memoir or seen the Oscar-nominated movie, Molly’s Game, you’ll know what happened next: she got robbed at gunpoint and raided by the FBI. They seized all her assets and she became a convicted felon.
In this episode, Molly reveals her hand - the stuff you didn’t get to see: her relationship with her family, the path to sobriety, letting go of status, and finding her calling.
A Good Story (25:58)
“I'm in this place where I'm 35 years old with millions of dollars in debt. I'm now a convicted felon. My reputation is destroyed. How do I get out of this gutter? …I treated it almost like a start-up, the re-invention is saving your own life.”
It was only a matter of time before Molly’s life caught up with her. Losing everything in an instant forced her to make a choice about which direction her life would take.
As it turns out, everyone loves a good story - and Molly had just lived one of the most compelling ones. After publishing her memoir, she set her sights on Hollywood. Molly’s Game (written and directed by Aaron Sorkin) was released in 2017 to positive reviews and an Academy Award nomination.
Finding Answers (30:27)
While she waited for her movie to come out, Molly was certain that she would feel better once everything came together. She waited anxiously, struggling on-and-off with sobriety, convinced that success would bring her happiness.
However, despite a big paycheck and the movie’s release, Molly still felt empty. She decided to move home in search of answers, purpose, and meaning.
“The movie's coming out in six to eight months and it's all set up right? I should feel better. No, I didn't at all. I felt worse. And so it was in that moment that I realized that everything that I had thought about life, about fulfillment, about happiness was wrong.”
Family (56:58)
Growing up, Molly had a turbulent relationship with her father. Her two brothers, overachievers in athletics, academic, and career success, were always deemed favourites. She constructed a narrative in her mind that she would never be loved in the same way.
In a difficult conversation with her father, Molly finally learned the truth. The story she told herself was false. She had spent her entire life harboring resentful feelings based on misconceptions. This conversation had a profound impact on her, and allowed Molly to repair her relationship with her family.
“Every bit of my relationship with my dad was built into that story. After we had that very honest, very vulnerable conversation, it all dissolved. And now I have the relationship with my dad that I always wanted as a kid. He's my biggest cheerleader and we're so close.”
Key takeaways:
Always remember why you started in the first place. When our motivations change, it is easy to make mistakes. Molly's plan from Day 1 had always been to make money, build a network, then bounce. But somewhere along that path she got caught up. She stayed, and her motivations changed. This led to a bunch of bad decisions and events that could have been avoided.
Bigger game, bigger stakes. One of the reasons why chasing money doesn't make you happy is that the more you have, the more you need to worry about. The severity of these worries scale with you. When working at waitress' salary, Molly's biggest worry was getting fired. When she brought in $5m per year, she had a gun in her mouth and needed to worry about staying alive. It's a lot to have, but a lot to lose.
Question your narratives. Sometimes we harbor doubts and resentment for years before asking if our assumptions are correct. Molly pushed her father away for a long time, feeling hurt because she held a certain narrative about how he treated her. However, the moment she talked to him, that mental model dissolved - it was all in her head. Don't let assumptions hurt you and the people you love. Ask the hard questions, and hear from them before you make judgements.
Here’s how Twitch pulled in $1 million a month in revenue:
Investors are always looking for the coveted ‘p’ word: profitability. Unfortunately for Justin and his founders in their early days, Twitch was nowhere near that. Here’s the rundown of how they managed to pull themselves into generating $1 million/month in revenue!
During their monthly founders meetings, the team made two lists:
1. Ways to make MORE money
2. Ways to spend LESS money
Nothing was off the table - everything from cramming in ads, to dropping video resolution in order to reduce server loads. So yes, Justin and co. invented the dreaded auto-play video ads. Thanks Justin.
From that point on, everyone at Twitch was focused on one single target: making money, or saving it. All projects were aimed towards the goal of profitability. Justin even promised that he would take the whole company for a trip to Hawaii if they managed to bring $1 million in a month.
In the months since the issue was challenged - Twitch more than tripled their revenue, hitting that sweet $1,000,000. They had achieved this by re-negotiating advertising contracts, optimizing their conversion funnel, and A/B testing their entire paywall.
Here are the key lessons:
Set a goal, even a made-up one! 🎯
Don’t get caught up in worrying about setting the wrong goals, or the validity of them. Paralysis by analysis is real, and your team needs an internal goal to get anywhere - even if its completely made up!
The ‘Why’ is important 🧐
Big shifts are hard, and you need everyone to be on board. In order to do that, everyone needs to be on the same page and understand the motivations for it. Make sure you’re communicating this clearly and directly.
Work hard, PLAY hard! 🎉
It’s easy to get caught up in always looking to the next thing (see Hedonic Treadmill). But its just as important to take a second with your team to reflect on your hardwork, success and celebrate together! This keeps you motivated, mentally healthy, and satisfied about your work.
Weekly AMA with Justin 😎
Got any burning questions you’ve always wanted to ask Justin? We’re featuring Q’s from our community and A’s from Justin on a weekly column right here! Make sure you’re subscribed, and submit your questions in the comments section of our newsletter.
We’ll pass 1-2 questions onto JK every week. If you’re picked, your question, name, and socials will be featured in the following week’s issue!
What are you waiting for? Leave us a comment:
Blackbird VC x Startmate Fireside Chat
Justin Kan is taking the world by storm! His first stop: Australia 🇦🇺 🦘
The Quest has partnered with Blackbird Ventures and Startmate to bring you an exclusive Fireside Chat with JK. Hear the legendary tale behind the man who brought internet livestreaming to the world! Check out the event here.
Event goes live at: Apr 8, 8:00 AM (Australian Eastern Time). Don’t miss it!
Episode drop notifications and transcripts - straight to your inbox!
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👀 Coming up next…
In recognition of the recent surge in Anti-Asian violence and discrimination, we will be dedicating this month to highlighting Asian American community and leaders on this podcast.
Moses Lo - founder of Xendit and YC alum. Moses engineered his luck, journeying to Silicon Valley from Australia and will discuss how 6 weeks in YC changed his life forever. If you're starting out as a founder or applying to YC, this is a must-listen for you.
Episode drops 6 April 9AM PDT. See you there. 👋🏼
