Molly's Game

In this post I talk about getting introduced to the underground poker scene of NYC.

In 2014, Molly Bloom wrote a memoir about her life and career titled Molly’s Game. Molly was a competitive skier, with dreams of participating in the Olympics. However, she suffered an injury while attempting to qualify for the Olympics. This turn of events caused her life to change trajectory. She initially worked as a bartender before finding a job working as an assistant in the basement of a famous club, The Viper Room. After working as an assistant for a few years, she became a game-runner herself, making as much as $4 million a year while servicing high rollers and celebrities, including Leonardo DiCaprio, Ben Affleck, Matt Damon, and Phil Ivey. After a move-in to New York, having a run-in with the mafia, and battling drug addiction, the FBI eventually shut Bloom’s operation down, charging her as part of a $100 million money laundering and illegal sports gambling operation. 

The day I arrived in New York, I had planned on grabbing dinner with Steven at a local restaurant. When I first stepped foot on the streets of Manhattan, I was overwhelmed. 

Floods of people were walking about, all rushing to get to their destination. Traffic was at a standstill as roads were congested with cars and bikes. 

The streets were full of life. Sidewalks teemed with Wall Street workers, dressed up in suits while carrying out important phone calls, tourists who were visiting Times Square with their families, cart-pushing vendors, hustling to make some extra dollars, and the homeless who set up encampments on the corners of the road. 

While walking to the restaurant, I saw a bicyclist slapping the windshield of a cab while flipping off the driver, a grown man scampering around in a Giant Rat costume, and a homeless man, likely incapacitated, defecating on the corner of a street.

Not things I typically saw in Michigan. 

Once I arrived at the restaurant and met Steven, I mentioned the wild scenes I had seen within the first hour of landing. He laughed to me and said:

“Welcome to New York.” 

I was only in the city for the long weekend, so Steven proposed that we go check out a home game that night. Every poker player has that feeling - when you get an itch to play. At that time, I had built most of my roll through playing online home games, so I was excited to try a new environment of playing live poker. 

For those not familiar with the poker scene in New York, home games dominate the poker ecosystem. This is because New York abolished all forms of gambling and lotteries in the state’s Second Constitution. As a result, game-runners took the liberty of hosting and organizing their own games, making money by taking a percentage of the pot during each hand, which is known as rake.

That night, Steven and I went to go visit my first home game, ran by a member of Poker After Dark. 

Located in the Brooklyn borough, the game was located in the basement of an apartment, which was rented out solely for the purpose of hosting poker games. It wasn’t too fancy, but it got the job done. Snacks and drinks were available and sushi was ordered that night to feed the players.

I was greeted by a younger crowd, primarily college students and kids who had just started work. There were two tables of $1/$3, with the max buy-in being $500. I opted to just buy in for $200, as I was nervous as hell - I hadn’t played live in a long time and this was the first time I’d ever played somewhere underground. 

After an hour of play and  my nerves settling down, I took a deep breath and analyzed my surroundings. 

At a game like this, the rake averaged to be 10% of the pot up to $20, averaging out to be three to five hundred per hour per table. It was the hosts job to find players and provide a space to play. The more action a player was and the deeper pockets they had, allowed for pots to be bigger and the game to last longer, meaning more money raked in for the hosts.

It dawned on me how extreme the hustle culture was in New York. I had noticed it before, watching street vendors set up shop or getting approached constantly on the streets of Manhattan to purchase various commodities.

One of the hosts who ran the game just graduated college and couldn’t find a job. Another decided to drop out of college to focus on hosting and dealing poker games as a primary source of income. 

Each night the hosts could make up to a few thousand dollars in rake, which first had to cover living expenses, equipment, food and Uber drive expenses for the players. The rest of the money would then go into their pocket.

The dealers of the game were college students who dealt as a side hustle. They would make roughly $50 an hour, depending on how much tip they received.

Sure, hosting or dealing a $1/$3 game wouldn’t pay doctor money - but it wasn’t a bad gig, especially for those who struggled with finding a job or wanted to make some extra cash.

I had a great time conversing and battling with these New Yorkers. Many of them were just like me, kids who also got a rush of adrenaline from playing cards.

Once my first trip to New York concluded, I couldn’t wait to go back. I loved everything about the city: the energy, the freedom, and the never-ending things to do. On the flight home, I made a promise to myself that one day I would make the move.

Things back in Michigan weren’t exactly superb. I was skipping most of my classes and my grades were tanking. Despite getting straight-A’s my freshman year, the highest grade I got junior year was a B-. Instead of focusing on school, I was occupying any spare time I had to play and study poker.

I immersed myself in the poker world, watching YouTube clips of high stakes streamed games or watching professional poker players stream their sessions on Twitch. At this time a name was buzzing around the poker community - Landon Tice. 

Landon Tice was only a year older than me, but was advertised as a poker prodigy when he binked a tournament in Vegas for over $200k. I was in awe. I thought to myself:

How could someone so young have so much success in poker?

So I did some digging and found that he was recently interviewed on a poker podcast. In the interview, he elaborated on his rise from playing micro stakes online all the way to high stake, attributing a lot of his early success to signing with Poker Detox, a coaching for profits stable. In exchange for backing and coaching, the horse or student would agree to give a percentage of his/her profits away.

I applied to Detox by sending them a video interview explaining why I wanted to join and my graph - at the time I was a slight winner at 50NL online.

The months immediately after signing with Detox were a blur. I would barely attend class, let alone do homework. Instead, the typical school day was replaced with grinding hands, each month playing over 200 hours. Within a little over three months, I had moved all the way from 100NL all the way up to 1000NL, 10X’ing my stake in 100k hands. 

My sunrun at 200, 500 and 1k NL.

I had risen up stakes faster than any student or coach in Detox’s history. Those few months I was on cloud 9. Poker seemed too easy and I was becoming complacent. However, any serious grinder knows that my results were atypical and I was clearly getting hit by the deck. 

The fall semester of my junior year was coming to a close. Steven’s birthday just so happened to be coming up. Coincidentally, a fellow poker friend told me about a much larger home game that he was playing in New York, one that he thought might interest me. For these reasons, I decided to make the trip out to New York once again. My roll had grown to just shy of six-figures and I was ready for a challenge.

Landing in New York for the second time felt like coming to a second home. I forgot how much I missed the city. Each time I stepped foot on the streets of New York, it opened my eyes, mind, and heart. 

Celebrating Steven’s birthday was a blast. We had a nice steak dinner amongst friends and ended the night downing booze at a nearby club. But I wasn’t there just to celebrate Steven’s birthday, I still had business to take care of.

The next day I got an address from my friend directing me to the home game. I arrived at a luxury apartment complex. I told the door man I was here to see the host, and he buzzed me up, telling me to go to the penthouse floor. 

My nerves quickly crept in again. I didn’t know what to expect. As I walked into the apartment I was taken aback by what I saw. This wasn’t a home game run by college students. I was clearly the youngest person in the room and surrounded by a much older crowd. 

There were two games running: the main table was a $25/$50 game and the secondary table was $5/$5. 

The host, an attractive woman, greeted me and asked me which game I would like to play. I told her I would play the $5/$5 and buy-in for two thousand dollars. She gave me a seat and chips to play with.

Except, I couldn’t play. Not just yet. There was way too much going on, and I couldn’t focus. I was breathing so fast to the point of hyperventilation that I decided to excuse myself to the balcony.

I closed my eyes and took in some deep breaths of the cold air to ease myself. When I opened my eyes, I saw the beautiful view of the city at night. The balcony had a direct view of the Empire State building. It all seemed like a dream. Here I was, still not even graduated college, gambling in a penthouse apartment with wealthy businessmen, hedge fund managers, and lawyers.

Was life even real?

As I stepped back into the apartment to take my seat, I took a quick survey of the main table. The straddle was frequently on and the game was playing much bigger than advertised. There must have been almost half a million in chips on that table.

A massage girl greeted me and asked me if I wanted anything to eat or drink. I politely just asked for water. I noticed three massage girls working that day, making their money through tips which businessmen would casually fling their way.

The whole setup was eerily similar to Molly’s game, preying on the desires of men. 

If you wanted Omakase sushi or expensive wagyu steak for dinner? The house would have it delivered for you.

If you wanted to drink while you play? The apartment had a full bar service. 

If you wanted a massage while you played? You had three attractive women to choose from.

A game like this would rake in much more than those $1/$3 Brooklyn games. On good nights the host could rake in mid 5-figures.

I ran extremely hot that day. After a couple hours of tight solid play, I turned my initial $2k buy-in into a $10k stack before the secondary table broke. 

Despite it already being past midnight and me being up a good chunk of money, I couldn’t help but want to sit in the main game. Something about playing a $25/$50 game with constant straddles and stacks sitting as deep as $100k piqued my gambling itch. So instead of calling it a night, I decided to sit down. 

Was I rolled for the game? Absolutely not. 

But I didn’t care. This was all a dream to me. I was just there to have fun.

So I sat down, with about $10k in front of me, ready to battle.

After sitting down and getting comfortable, I started exchanging friendly banter with the other players at the table. 

There was the cordial lawyer, who was always high and went to the game to escape time from his wife and kids. A hedge fund manager, who loved giving action and even bought one of the massage girls into the game. A Russian businessman, who didn’t seem to want to talk to anybody and had his earbuds in the whole night. All very financially successful people who came from various backgrounds. 

About an hour passed with no interesting hands until I picked up AK offsuit, a very strong holding. A $100 button straddle was on by the hedge fund manager. I had noticed he loved to raise any two cards, so after three limps in front of me, I decided to call my hand as well and not raise. It folded to him and on cue, he raised it up to $800. The initial three limpers folded and now I had a decision to make. My hand here was nearly the best preflop 99% of the time, but AK was still a vulnerable hand, and I didn’t even have a pair yet. As I didn’t want to make any mistake postflop, I announced two words:

All in.

$10k, shot straight into the middle.

Within a half a second, the hedge-fund manager put one chip into the middle, signifying a call. 

I gulped. A snap-call wasn’t good, and if he had AA or KK I could be drawing nearly dead. Before the cards were dealt, he asked:

“Do you want to do any business?” 

“I would prefer to run-it twice, it’s a big pot.”

I was extremely nervous about losing my whole stack, $10k is a lot of money and running the boards twice would allow me to reduce the variance.

“I’m just messing with you. I only run it once.”

Yikes. I was beginning to understand that this was all a game for him, he didn’t care about the money. He was just there to gamble. 

The dealer dealt out the board coming out A♣️3♥️5♥️.

The opponent muttered to himself and seemed upset at the ace coming out, which meant my hand was likely best.

The turn came the 9♥️ and the river came the T♥️.

Now it didn’t matter that I had top pair, any holding with a heart would beat my top pair. My opponent quickly turned over his hand Q♥️Q♦️, for a queen-high flush.

My heart sunk, thinking I had lost this pot. I anxiously turned my hand over to check if I had any heart and breathed a sigh of relief as I was holding A♥️K♣️, allowing me to scoop the pot.

“Nice win, kid.” The hedge fund manager remarked.

I cashed out that night a profit of $20k, my biggest win by a mile. It also marked the first day my net worth hit 6-figures.

The host pulled out a stack of cash and ran it through a money machine. I had never touched so much money in my life. Instead of asking the host for an Uber ride or for the personal chauffeur to drive me back to Steven’s, I opted to walk back instead.

I was on a high like no other, running across the streets of Manhattan in the late morning like a madman, with $20k stuffed in my coat pocket. 

I decided when I left for Michigan that weekend I would make a plan to move to New York.

But I clearly wasn’t ready yet.

I was impulsive, reckless, and naïve. And things weren’t going to turnout the way I had planned them to be.