I first met Haley at one of those pretentious Upper East Side cocktail parties that Woody Allen makes fun of in his films, where they serve fancy hors d'oeuvres like curry quail eggs with organic squash and try to impress their guests with overpriced French Bordeaux wine that gets you as drunk as a bottle that's 1/4 the price. During our first conversation, I asked Haley one of the three standard questions people in New York ask each other.

"Where do you live?"

"73rd and Amsterdam," she said as I stared at her breasts.

"Ah, right around the corner from Player's Club."

"Huh, what's that?"

"Oh, it's an um.... an underground poker room that I play at. Sometimes."

"Ewww! Poker?" as she rolled her eyes. "Like an illegal casino with mobsters and extras from The Sopranos?"

"Something like that."

Poker became such a major part of my everyday mental processes that the first thing I thought of when Haley mentioned where she lived was the exact distance from her apartment to the poker club that I used to play in. She sarcastically rolled her eyes at me that night when I mentioned poker. I'd roll them back at her one year later she'd ask me to help teach her and her friends from her acting class how to play Hold'em in the infamous Haleywood Homegame.

I had been writing on my poker blog for about six months when I met my first fellow poker blogger, Ugarte from Rick's Cafe. He and a few of his lawyer buddies had a group blog and a homegame. In one of those weird Six Degrees of Pauly, we found out that he went to law school with one of my prep school classmates. Ugarte invited me to his homegame at the Blue Parrot and I showed up with a six pack of Red Stripe and $200. Through Ugarte I'd meet Ferrari, Coach, Rick, Swish, and F Train who went to law school with Rick. We'd play dealer's choice on Monday nights and the games were ferociously fun. I introduced them to The Hammer and by the second homegame, everyone at the Blue Parrot wielded Hammers like they were pocket Aces.

At the time I supported myself by playing poker. I grinded it out for a couple hundred a week playing $1-2 NL in the underground clubs in New York City and I frequently played at Foxwoods or in AC, renting cars when my bankroll permitted, otherwise taking the bus with the other degenerate gamblers. I was reluctant to play online poker, despite Iggy and HDouble's endorsement of the fishy games on Party Poker. All of the winnings from my live play went to pay bills. I got caught up in that horrible habit of using my bankroll for non-poker things, instead of reinvesting back into my bankroll and moving up in levels. For the short term, I was fine but I craved the camaraderie of a homegame like Jerry's in Atlanta or the Trout House in Seattle where I could hang out, watch sports, drink, curse, smoke and have a few laughs. That's when Ugarte invited me to The Blue Parrot and I met some folks who would end up becoming close friends.

A couple of months later I met four more poker bloggers. I got blitzed with Daddy at setbreak of a Phish show in Deer Creek, Indiana. I had just smoked opium in the bathroom with a barefoot kid with a tattoo of 4:20 on the back of his neck, when Daddy and I crossed paths for the first time. A few days later, I visited BG in his Western Michigan hamlet. I sat in on his homegame during his 30th birthday and I met the cryptic Lord Geznikor. (I am the only blogger who's met Lord Geznikor and SirWaffle. I dare anyone to top those feats!)

Earlier that month, I also met AlCantHang at a Phillies game. He introduced me to his merry posse which included his lovely wife (and one of the few chicks who could drink Jim Morrison under the table) EvaCanHang, BigMike, Landow, and the infamous Lewey who sent me on tilt in Al's homegame.

I was in contact with group of twenty or so poker bloggers, which was about the majority of the bloggers at the time. I'd play on the $25 NL tables on Party Poker with Derek, The Fat Guy, Mr. Decker, BadBlood, Iggy, Maudie, Chris Halverson, BG, Lord Geznikor, Mean Gene, Glyph, HDouble, and Otis, while we'd sweat Grubby while he played 4 SNGs at once. We couldn't wait to drop the Hammer and put the other players (non-bloggers which we condescendingly nicknamed "tourists") on uber-tilt.

Iggy, Felicia, and Grubby set up different blogger tournaments and we played in them for shits and giggles. We jokingly called ourselves the WPBT as a spoof on the WPT more than anything else. Most of my adult life I avoided participating mainstream group activities. Joining a "club" or paramilitary organization was the last thing I wanted to do. I met some cool people and had a blast playing poker. But we also developed deeper friendships based on our other common interests.

Our friendships gave us the inspiration and encouragement to become a support system for each other. We all helped lay the foundation and from that solid base, a community sprang up and began to flourish. Over the past three years, hundreds of other blogs have built upon what we started.

Every few weeks I'd get an email from a reader and fan who told me that I inspired them to start a poker blog. I realized that the majority of people who read my blog didn't have one. I really thought that only other bloggers and my friends read my blogs. My words helped inspire strangers. I was blown away and mortified.

I wandered over to this side of the web and set up shop, thinking that there would be no way anyone else would do something similar. I was wrong. I was no longer the crazy guy in the woods living in a shack. Other lost and curious souls from all walks of life built of shacks next to mine and we soon had a shanty town. Then a ghetto.

I had written for several years without any financial success. Friends enjoyed my work but their endless encouragement didn't pay the bills. Sure, being a writer got me laid every now and then, along with a lot of free meals from friends with real jobs. For the most part I took a vow of poverty when I decided to pursue writing as a career. If I wanted to make money, I would have stayed on Wall Street or tried to find other work in that sector where you are compensated for your services. I took a different path and accepted that the cut in pay would also allow me the freedom to create while gaining experiences and exploring an adventurous life that millionaires try to buy when they are retired.

When I was hired to write my first freelance poker assignment, I was baffled, excited, and angry. Poker was by far the worst of my writing. I wrote a half a million other words that were much better, yet those were ignored. In late 2004, I had completed five novels and two screenplays and had not made a dime from my writing.

With the poker boom, my services were needed. I happened to be at the right place, at the right time. A European site called Professional Poker offered me a job to help write player profiles of selected pros. The owner was a regular reader of the Tao of Poker and liked my writing style. I started out writing a weekly assignment, which lasted for a year and a half. And of course, it took European sensibility to realize that I had talent. Thanks to W at Professional Poker for offering me my first poker job.

As Woody Allen once said, "Here, I'm a bum. There, I'm a genius. Thank God that the French exist."

The other assignments came rolling in. PokerTV.com needed content and I obliged. PokerMagazine.com hired me to write regularly for their site. Inside of a month, I had three clients that offered me steady work. That's when the Poker Prof offered me a job to move to Las Vegas cover the 2005 WSOP. That's when most of you started reading me from about a year ago. Through the Prof, I was picked up by Poker Player Newspaper. Through Poker Player, I was picked up by Fox Sports.

For a couple of hours (on more than one instance) during last year's WSOP, one of my poker articles was the lead story on the Fox Sports homepage. My 15 minutes of fame started winding down at that point.

During the WSOP, I met Lou Krieger through Amy Calistri. They were both avid readers and Lou's a real poker writer, not a hack like the majority of people in this industry. Lou created space for me in Poker Pro magazine. He told them to start a tournament column which would insure that I got an article in every issue. Since then I've also collaborated with All In and Bluff. I have never written anything for Card Player Magazine. I've never been asked.

Late last year, I was hired by the Borgata to help live blog their Winter Poker Open. That was the first time I was employed by an actual casino. Despite the long hours and working for 13 straight days, it was an amazing experience.

The pinnacle of this amazing adventure had to be the night I went to the Playboy Mansion a couple of months ago with Spaceman, CJ, Chad, Joe Speaker, BG, Bobby Bracelet, and AlCantHang. The eight of us, all of whom were decked out in new clothing, gathered on the front lawn of Hef's as the celebrity charity tournament winded down. I had just taken a piss on the lawn after I ripped a gager by the spider monkey cage. AlCantHang was lying on one of the lion statues and smoking a Marlboro. I looked around at my friends and a wave of humility fell over me. The moment wasn't special because I was at the Mansion. It was special because I got to experience it with my friends.

I've led a lucky life. I'm the luckiest person that I know.

Sometimes the cards aren't falling the way I want, I remind myself that I might be unlucky at the tables but I'm sitting pretty with a monster stack in the game of life.

For a while I grew extremely confused with the future of my career, writing, and the blogs. I hated all things poker which was ironic since it was the main source of my friends, income, and popularity. I should have been happy but wasn't. And I couldn't continue with anything until I discovered the source of disdain and depression. Shortly after the Mansion, I began to reassess how I approached everything in my life. It took me a couple of weeks of soul searching in Hollyweird of all places. After a good old fashioned bender, underneath the ubiquitous palm trees and thin layer of smog, I rediscovered the passion in writing and in poker.

I stopped worrying about the things I couldn't control or change, and focused on my strengths and what I could improve. Blogging is not writing. And I stopped blogging and started writing. I cut down my time on the internet. I stopped reading poorly written blogs and stopped reading blogs that I used to skim. I used the time that I was wasting to read books by excellent authors.

I changed my philosophy of how I cover poker tournaments and my gamble paid off. I was happy with my new format because it gave me more free time and it actually worked. I have a gameplan for this year's WSOP, something I didn't have last year. And for the first time in a very long time, I was excited to move back to Las Vegas and cover the WSOP. Before, I had been dreading it.

Since my revival or rebirth, I've been in a much better headspace. I'm not as moody or grumpy. I have a purpose again and don't feel like an old French whore. Although my writing has flourished across the board, I know that I can still do better. Right now I'm a C student but if I keep pressing myself, I can become a solid B+ student in about five or six more years.

* * * * *
This series came out of nowhere. It always existed. My past has always been there for me to use as material. It was a change of pace and something different to write about instead of bragging or lamenting about my wins or losses on the online site du jour.

When I got back from to NYC after the WPT Championships, I took a few days to clean out my old bedroom in my mother's apartment. It had become a storage space for myself and Derek, and a sometime flop space for me. There's an old futon mattress that I had from college in the corner and I wondered what the Over/Under was for how many girls that I slept with on that mattress faked their orgasms?

The room was a mess and unorganized. I had boxes and boxes of crap with paintings stacked up on one side of the room and books scattered all over. I grouped the books into one place and started throwing out useless junk and memories that I didn't mind going into the trash. During this Spring Cleaning, I was bombarded with flashbacks. It was inevitable. Seeing a painting, or a box of photographs from college, or a shoebox filled with concert ticket stubs filled me with memories. The once dark room was a museum to myself and I locked away all those feelings for the last few years while I've been on the road living out of my backpack again sleeping in different casinos, motels, and friends couches.

I once wrote about the Bozos and the Bolos. I said:

The Bozos had seats facing backwards on their tourbus so they could look back, while the Bolos sat looking forward. That represented two styles of thought. Are you one to look back constantly? Or do you stay in the moment while looking toward the future.

I've always been one to look forward more than looking back. The past was over and does not exist anymore, only inside the hallways of my mind. I'm the type of person who relishes living in the moment. But over the past month or so, I have been looking back. Sometimes to remind myself to lighten up and enjoy my life. Sometimes to try to figure out where I fucked up and how I can avoid that again. And sometimes just to feel better about myself. Sure there were plenty of sad moments, but I also hit some amazing highpoints that I wish some of you have the chance to experience in your lives.

The Tao of Poker is where I talk about the way of poker in my life, whether it's playing online or at the WSOP. Poker has been my gambling mistress over the last few years and if there's anything we both learned from the Born to Gamble series (besides, "Dude, you smoke a lot of pot!") is that gambling has been an integral part of my life, as much as breathing. It's always been there both directly and indirectly.

And I'm not just talking about gambling for money. I've gambled with my life, too many times to count. I've put my body through some several rigorous activities from various sports injuries to destroying millions of brain cells and weakening my liver during week long alcho-narco binges. I've driven drunk. I've cut the tags off my mattresses. I've gone swimming right after I ate. I've run with scissors. I had unprotected sex. I took plenty of chances running thousands of red lights. I bought hash off of razor blade toting Persians in a dark alley in Tokyo. I've flown on Air Pakistan...

The immediate high was more important than the future consequences. It's always been like that. That's why I gamble so much. The orgasmic rush. I've been chasing the high for my entire life. And when I get a small taste, it gives me a feeling of invincibility. Then I want more...

I've gambled with the law so many times. As much as you might think I've broken the laws with underage drinking and other substance abuse, nothing compares to the criminal acts I undertook when I worked on Wall Street. If I should be imprisoned, it would be for the crimes I committed against humanity when I wore a Brooks Brother suit.

I've gambled on friendships and relationships. Sometimes I knew I shouldn't be associated with some people, but I kept pressing my luck. I took leaps of faith with women I barely knew and jumped into relationships, knowing that I was a 5 to 1 underdog, yet fell hard and fast anyway.

I've gambled with my career so many times. For a while I got paid to gamble with other people's money. Then I took several big risks by leaving Wall Street during my attempt to become a writer. For many years that gamble was not paying off. These days, I take chances with new freelance clients. Will they pay me on time? Will they fuck me over? I assess the risk and take the shot.

I took a huge gamble last year when I accepted a job from the Poker Prof and covered the 2005 WSOP. Every time I stepped out of the Redneck Riviera, I gambled with my life. And this year, I'm going to gamble again and try to do thing differently at the 2006 WSOP.

Over the past few years, I grew frustrated that I couldn't get published in certain magazines or websites. I might be a considered one of the better writers in the poker industry, but that means jack shit in the real world of publishing. I'm still dealing with rejection on a daily basis which is humbling and frustrating. My work has yet to make it in front of a mainstream audience after a decade of sweat and agony. Maybe that will change as I have my eyes set on pursuing a career in Hollyweird.

I desperately wanted to get paid to write a weekly column at a number of places. That's never going to happen and the reality had depressed me. That's when I realized that I have something that's better than the prestigious gig that I thought I wanted. I own real estate on the web where I can publish my own words. Sure I might not get paid as much (if at all) for my writing, but at least I can control what I say and when I say it.

So who needs Salon, Harper's or Card Player when I have the Tao of Pauly, Truckin', and Tao of Poker?

Some of my favorite writers have never reached the audience numbers in their lifetime that I'm getting on a daily basis. I'm not going to waste that opportunity anymore. Last year, during the main event of the WSOP, I had well over one million unique visitors stop by the Tao of Poker. That's the equivalent to the city of Seattle. Imagine everyone in Seattle reading your blog and hanging on every word. Talk about pressure. That's enough to give anyone stage fright.

This year, I'm expecting a similar number of visitors hopefully more with at least two million or so sets of eyes fixated on the Tao of Poker's coverage of the 2006 WSOP. Judging by the quality of my writing over the past two months, I'm ready for that challenge. All artists, musicians, actors, painters, athletes, writers, singers, and comedians want to show off their skills in front of an audience. They want to make an impression onto society.

In a few weeks I'll be given that rare opportunity. It might be the last time I get the bright spotlight on me and I'm not going to waste that chance to speak my mind and talk about the way of poker as I see it at the WSOP.

That's why I rejected a fat paycheck from an online site to blog for them at the WSOP. I scoffed at the notion that a popular poker magazine wanted to offer me an hourly wage, that's the same as the other flunkies they get off of Craig's List. I'm going to the 2006 WSOP by myself which means that I'm paying my own way. I'm trying to get a sponsor in the next few days which will help cover some of the costs, but for now the airfare, rental car, rent at Grubby's, food, and lapdances... are all on my dime.

I'm going to cover the 2006 WSOP for the Tao of Poker and for the Poker Prof's Las Vegas and Poker Blog. I still will be contributing bi-monthly columns in Poker Player and I still have my column in Poker Pro. Anything else I do for them or any other media outlets like Fox Sports or Bluff will be on a freelance basis. I'm excited to work side by side with Flipchip again. His WSOP photos and my words will help tell you the daily story at this year's WSOP. Flipchip and I are the best at what we do. Scott Joplin once said, "It ain't braggin' if you can do it."

We did it last year and we're going to do it again. I hope you come back to experience the ride. And tell your friends and co-workers.

As long as I can remember, I've been gambling my entire life from the first Super Bowl I ever saw to getting my Pocket Aces cracked on Party Poker a couple of hours ago. And the biggest payoffs have been when I've gambled on myself as a longshot... and won. I've been doing things my way and I'm going to continue to do so. I was born a gambler and I'm not going to stop anytime soon.


Editor's Note: If you have not read the first five installments of Born to Gamble, then visit Part I: Where It All Begins, Part II: Southbound, Part III: Midnight Rider, Part IV: Ramblin' Man, and Part V: Whipping Post.

I never believed in love at first sight until my weary eyes fixated on Angela. She and her friends parked and camped out next to me at the Gorge in George, Washington. She wore purple sundress and her long light brown hair cascaded down her small frame. Her resplendent brown eyes captivated my soul the second we made eye contact with one another. She barely stood five feet tall, but her aura ran me over like a freight train. She spoke with a slight drawl which gave me goosebumps every time she opened up her mouth.

"I know you're not from around here," I said.

"I'm not. I'm from Tex-is," she said.

"Tex-is? Or Tex-as?"

"Tex-is. Cause Tex-is where it's at."

That would be one of her many Texasisms that she would lay on me. Some of my favorites included, "You can put your boots in the oven, but that don't make them biscuits." Or my all time favorite, "You keep trying to sell me that lie, and I ain't buyin'."

In the summer of 1998 I saw two Phish concerts at the Gorge Ampitheatre, and that's where I met Angela. She and her friends from college drove up from Austin and coincidentally parked next to me in the campgrounds. We hung out both nights and stayed up late talking about everything. When it was time to go she promised that we'd keep in touch. She drove back to Texas to finish her last year in college and I'd be heading back to NYC a few months later when I found out my mother got sick and I had to come home.

During our time apart, we'd speak on the phone, shoot each other emails, and IM one another. My favorite parts of our courtship were the letters we'd write one another. She was an English major and wanted to be a writer. She had no problems whipping out ten or fifteen pages of elegant prose and mailed them to me with girly doodles of flowers and happy faces on the pages or the envelopes.

(Editor's Note: When we eventually broke up, I told her that I burned all of her letters. I lied. I was angry and wanted to hurt her. She broke my heart and the only thing I knew I could say that could equally make her weep uncontrollably was to say I destroyed her love letters. To this day, I never told her the truth and I assumed that a part of her held onto a flicker of hope that I was just bluffing. They sit in a shoebox near my baseball cards in the corner of my old bedroom. I haven't opened that box in years. I still lack the courage to read her words.)

Phish played four concerts in NYC at Madison Square Garden the end of 1998, including their New Year's Eve show. I had an extra ticket to New Years and I posted a message on a Phish bulletin board that I had an extra and was looking for "interesting trades." One guy offered me $400 for the ticket when I got a call from Angela saying that she was looking for an extra ticket. I did what any guy would do... I gave her the ticket for free.

We had floor seats for New Year's Eve. Phish opened up with a cover version of Prince's 1999. Fitting, I thought, because I used to listen to that song when I was a kid and 1999 seemed so distant. But there I was, on the cusp of 1999 dancing in the middle of a sea of wasted neo-hippies.

Phish played three sets that night and took the stage for their final set at 11:45pm. When Midnight struck, millions of revelers were celebrating in Times Square nine blocks north of the Garden, and Phish played Auld Lang Syne as hundreds of various sized balloons of different colors fell from the ceiling onto the crowd (very similar to the scene in the documentary Bittersweet Motel which occurred on NYE in 1997). That's when I went in for a kiss. Our first kiss. And in the history of first kisses, it might have been number one.

When Angela graduated college in the spring of 1999, we embarked on a journey that would last almost a year and a half where we criss-crossed the country several times following Phish around on their various tours. We saw fifty or sixty Phish shows together in 30 plus states in two years along with catching dozens of other bands and visiting Jazz Fest in New Orleans. We spent weeks and months sleep deprived and jacked up on whatever party favors we could find. Lucky for me, I had two excellent runs during March Madness and my gambling bankroll helped fund our trips.

While we were on the road, we stopped off in places like Reno and Biloxi and I taught Angela how to play blackjack. She walked away with $200 one night, even though the dealer and pit boss carded her several times.

As much as my life was unstable, I found a semblance of happiness even though I was constantly on the road and lived out of my backpack for two years. We spent most of our time sleeping on couches or on the floors of friends' apartments in San Francisco, Seattle, Alabama, Ohio, and in Houston. We'd camp out when we could and spent the rest of the time in cheap motels avoiding the AIDS-ridden comforters and dried cum stains on the walls.

I got to see America again ad more of it from the highways, freeways, and backroads. Although certain parts of America started looking like one long homogenous suburban strip mall, there were still physical and geographical differences that set different areas of our vast country apart.

In two years we visited so many cities together that it's hard to keep track: NYC, Dallas, Detroit, New Orleans, Phoenix, LA, Portland, Boise, Denver, Memphis, Cincinnati, Indianapolis, Atlanta, Las Vegas, San Diego, Kansas City, Seattle, and smaller towns in between like Las Cruces, Pelham, Antioch, Columbus, and Vail. We spent the millenium in Florida seeing Phish's epic concert from when they played from 11:30pm to 6am without any breaks.

I'm shocked that we never got into any serious trouble. In Las Cruces at a traffic stop, state troopers wanted to search the mini-van that we were driving but Angela stood up to the cop wearing mirrored sunglasses at 2am, exhibiting her Texas toughness when she blurted out, "You're not searching my momma's van without a warrant. We're gonna pull over right here and wait until you get one."

Man, she would have been a great poker player. She pulled off the bluff of the decade when the hardass trooper let us go and never searched the van. You can only imagine what we were carrying.

We pushed our luck on so many nights. Life on the road is difficult and dangerous as is without encountering humorless law enforcement types. The road has killed some of the best musicans like Buddy Holly, Hank Williams, Otis Redding, and Jimi Hendrix.

"It's a goddammed impossible way of life," explained musician Robbie Robertson in the documentary The Last Waltz about constantly being on the road.

Yet, once again we both came out of it without a scratch with just a couple of speeding tickets.

So what happened with the adoarble girl from Texas that I thought was the love of my life? Hippie love never lasts and when we tried to have a normal relationship and stay in one place for an extended amount of time, things didn't work out. A few months after I got back from Japan with Senor, we broke up. She went to grad school in Texas and I wanted her to move to San Francisco, New Orleans, or Portland with me. Texas women are extremely stubborn and independent, and they don't like to be told what to do. Deep down, I thought that we were meant for each other and that we were just going through a rough patch. I figured that we'd get back together in a year or so after she got her master's degree. I was wrong. Each day, we drifted farther apart and she became freakishly and fanatically religious after 9.11 which that caused a deeper rift in our friendship.

When 2001 started, I was heart broken, deep in debt, and artistically lost in New York City. Senor always had a way of cheering me up and would say things like, "Women. Fucking women. Ah, fuck 'em. Let's go to Iceland."

This is the same guy who walked into a crowded bar in Rio di Janerio during Carnival, jumped up onto a table, dropped his pants, then announced to the patrons, "Who wants to suck my dick?"

Thank God for impulsive friends with credit cards. Just like that we were in Iceland a week later in the middle of January with about ninety minutes of daylight roaming the streets of Reykjavik drunk like toothless Hooligans on Viking beer. Senor read an article in Details magazine that Icelandic women were the most beautiful in the world and the easiest to sleep with. He figured a romp in the sack with a blonde Icelandic girl would lift my spirits.

A few months earlier in the summer of 2000, we embarked on the greatest trip of my life to Japan when we followed Phish for six concerts in four cities (Tokyo, Nagoya, Fukuoka, and Osaka) where they played in small clubs and venues. One gig in Nagoya was located in a club on the sixth floor of a shopping mall which had about 300 people packed into a space limited to 200. It was a special trip because we bonded with people who we had a tough time communicating with our different languages, but we were brought together by music. That was our translator as we discovered a sub-culture of hard-core Japanese hippies who loved the same bands I loved.

We befriended a couple of guys from Tokyo who were in band called Horse. They would come to America later that year and I took them on Phish tour with me and Angela. I made them wake and bake and ride the rollercoaster at New York New York during our time in Las Vegas. They were awesome guys and amazing guitar players. I helped write a few songs for one of their albums.

Yeah, I guess I never mentioned this, but years before I was an internet celerity, I was a well respected songwriter in the Tokyo underground music scene. I wrote the lyrics for Horse and they wrote the music. I was limited to using certain words and arranged them in a way that they could sing smoothly without too many pronunciation difficulties. It's odd to think, but right now a bunch of Japanese long hairs are playing songs that I wrote somewhere on the mezzanine of the Tokyo Subway.

(Editor's Note: Just a warning, the next several thousand words should not be considered light reading. I'm going to back that dark place inside of me to describe a three year period of my life that was equivalent to Dante's version of hell. If you are not able to handle that difficult material, then I suggest you stop reading this post.)

The break up with Angela set me on relationship tilt so badly that when I got back from Iceland I suffered the worse afflication that any writer could attract... I couldn't write. I didn't have writer's block. I don't believe in it. "Writer's block" is a pussy-ass passive-aggressive device that amateur scribes use to try to get sympathy from non-artistic types. My problem was that it just hurt too much to write because whenever I sat down to write, all I could talk about was Angela and how miserable I was without her and how happy we were when we were together. The one thing in life, writing, that gave me relentless pleasure, was also the source of intense pain.

I discovered painting around that time. I was going crazy and I needed some way to express myself. Senor and I saw these trippy apocalyptic landscapes in Iceland that were formed by volcanic activity. I still had those vivid images in my head after my trip and ended up painting a series inspired by what we saw. The ground was black. The sky was purple and the mountains were green.

I began painting without one art lesson and locked myself in my studio for several days at a time working on different projects. I made sculptures out of all these used lighters that I collected. I made paintings with used Metrocards. Whatever materials I could find, I incorporated into my art. There was a six or seventh month period where I was in a depressed state of mind and rarely left my studio. I never watched TV. I sat in the dark and listened to old jazz records and other depressing music like certain Johnny Cash ballads, Elliot Smith, and Radiohead. I read Dostoevsky constantly and visited museums where I would study paintings for hours at a time.

I also met a neurotic California blonde named Betty around the same time and we started dating after she successfully stalked me for several months. I slowly started coming out of my shell. By the end of the summer, I felt somewhat normal and healthy again. I spent more time with Betty hanging out in hipster coffee houses and trenoid bars in her posh Brooklyn neighborhood. Football season started and I was gambling on the pro games and ran pools and fantasy leagues with Derek and my friends.

Just when things started to go back to normal, 9.11 kicked me in the side of the head. I woke up early that day on a brisk and cool morning for early September with high blue skies. I was in the middle of writing something when I got an IM from one of my friends in Japan. He wanted to know if I was OK because a bomb exploded (that's what the Japanese press originally said happened) in the World Trade Center.

You know the rest of that story.

Betty freaked out and went back to California about a week after 9.11 on my birthday of all days. Alone again and lost, I was forced to attend several funerals and memorial services by myself. Several guys I worked on Wall Street were missing along with seven of my prep school classmates. By the fourth or fifth funeral, you get numb to it all. If you didn't live in NYC, you got to see some footage on TV of people weeping at vigils. But what you didn't get to see was the aftermath that infected New Yorkers weeks and months later when families realized that there were no bodies being pulled out of Ground Zero, just body parts and fragments. And the front page of the paper would be a picture of another brave and courageous cop or firefighter who had a funeral that day.

I watched mothers faint during their sons' funerals. I also burst into tears when a four year old girl ran up during one service and clutched her father's empty coffin. To me, that image was as much 9.11 as the planes crashing into the towers. All those solemn eyes and desperate souls crammed into a church consumed with rage and hate, and somewhere trying to make sense of why some of us live and others of us died. For a while, those would be the last tears I'd shed.

For a couple of months after 9.11, I wandered around with senses of hopelessness and helplessness. Senor felt even worse. He wasn't even in America during the attacks. He was on vacation, sitting in a bar in Vietnam brushing off the advances of several teenaged hookers when he looked up and saw the carnage on CNN.

I was already near rock bottom and 9.11 left me wondering, "What the hell am I doing here?"

And that's when the phone rang. Sometimes you get lucky in life when you need it the most. Mack, my former mentor and Wall Street jungle guide called to offer me a job. He started up his own firm and wanted people he could trust on his team. He said that despite walking off the job several years earlier, he still had a lot of respect for me and I was his favorite trainee and assistant that he ever had.

I was broke and directionless, so a second job on Wall Street seemed the right thing to do. Afterall, if we didn't get the economy back on track, then the terrorists win right? I finally had a feeling of accomplishment, like I was pitching in to do my share to help heal my city and my country. I became another spoke in the wheel of capitalism.

I was still had long hair at the time and I made a deal with my mentor that I'd cut my hair he waived the drug test. He agreed and I dusted off the Brooks Brothers suits and headed back downtown.

If you worked in Lower Manhattan after 9.11, then you know about the smell. That's what you didn't get from TV and internet images. The foul smell of death was omnipresent. Derek worked on Water Street a few blocks away from Ground Zero and would often call me up and say, "They must have digged up something really bad today."

These days, when I'm having a really bad day and start feeling sorry for myself, I remind myself of that smell and I'm jolted back into reality. If there's one thing I could wish for, it would be that no one, especially your children and your children's children, should never again have to experience the stench of destruction and seared flesh.

Some New Yorkers avoided walking by Ground Zero and chose different ways to get to work. I had to see it because it helped inspire me to work hard everyday. It was difficult enough walking into the trenches and seeing the first desk in the row blocked off as a memorial to one of Mack's friends (and a former co-worker of ours) who jumped to his death on 9.11. Every few days, new flowers would be set up and during certain holidays, his memorial was decorated accordingly. On St. Patrick's Day, I opened up a bottle of Guinness and left it in front of his picture. It was there for two days until one of the cleaning ladies threw it out because it began to smell.

As the days flowed into weeks and weeks flowed into months, I discovered that I was more depressed than ever before. The last place I wanted to be was stuck in an office on Wall Street. I got into a huge fight with Mack and ended up getting fired. I found a job later that afternoon when an old prep school alumni pulled a few strings for me at JP Morgan. We had been doing volunteer work together teaching inner city kids how to play chess. We'd go into the ghetto on the weekends for a few hours and play chess with kids. He was a few years older than me and worked at JP Morgan. One of his golf buddies was looking for a few new brokers and he hired me after a five minute interview.

JP Morgan was like working for the NY Yankees of Wall Street brokerage houses. I hoped that working for one of the big boys would lift my spirits. But it didn't last. I fell back into a deep funk. But at least I was a stock broker instead of trading bonds. And the irony of it all was that I was pitching pharmaceutical stocks to suburban dentists and widows.

I started a blog called the Tao of Pauly in May of 2002. My old college roommate was a journalist in Tampa and had a blog called The Daily Dave. He suggested that I start one too because it would be an excellent scratch pad for me while I worked. A month later I began Truckin' which would be a forum for my friends to share and post their travel stories. Senor had just quit his job and moved to Southeast Asia and had a ton of stories to tell. Plus I wanted to take some time and write my travel stories and since every magazine I ever submitted my work to rejected me, I wanted to publish my own work. Although starting to write again helped get me through my bitter days, I still hadn't found my voice and was miserable at work. Then things took a turn for the worse.

On the eve of my 30th birthday I had sunk to the lowest point of my life. It was a rainy day and water seeped through the sidewalk grates and sprayed the entire subway platform. The train was late and I stood in a wet suit after not having slept well in days. The end of the month was nearing and I was nowhere close to filling my quota. With the Enron scandal, consumer confidence was at an all time low and the Europeans pulled all their money out of the American financial markets. We were all struggling and I was caught in a heavy spin. I hated my life. Every ounce of it. I had such an amazing time in my 20s that life in my 30s seemed futile.

What was the point of living if I had nothing to look forward to?

I was working on Wall Street, yet still broke and deep in debt. Most of my friends were out of touch, dead, or joined the rank and file of suburban drudgery. I committed artistic suicide months earlier when I took a desk job and gave up writing. Plus I had just discovered that my lover was pregnant. How could we have been so stupid? I was almost 30, gaining weight, losing my hair, totally broke, and on the edge of hurling myself into the abyss. I wanted to jump in but was too afraid.

I reached a moment of desperation and prayed to God. I asked him to send a deranged homeless man to rescue me by pushing me to my death in front of the next subway. I wanted to die and was too chicken shit to kill myself, so I had to ask God to do it for me. I was a gutless prick and I deserved to be mangled beneath an uptown No. 1 train.

I don't think God was listening to me that day because the train arrived in the station and I got on and went home. Or maybe he was listening and decided that my life was worth sparing. That's for you to debate.

If there is a God, he saved me by not answering my plea for help. If there is no God, then I reached the tipping point where I thought that death was a better alternate to life. That's how serial killers turn to the dark side. That's how suicide bombers think before they strap on the bomb vest. That's what goes through people's minds before they jump off the Brooklyn Bridge.

If I honestly thought death was a better option than life, then I needed to make changes in my life to make it more meaningful. The next day during my birthday dinner, Derek saved my life when he threw me a life preserver. He asked me if I saw the last episode of Project Greenlight, the screenwriter contest where you get your script made into a film by Ben Affleck and Matt Damon. He joked that I was a better writer than any of those hacks and that I should enter. In fact for my birthday present, he offered to pay for the entry fee. I went home and looked on their website. I had ten days until the deadline and no idea for a script.

I cranked out something called Charlie's Goldfish about a guy from New York who worked in Hollywood and came home after his father's death and found out that the bar his father owned was going to be sold and made into a Starbucks. Since I only slept two or three hours a night anyway, it took me less than 10 days to write (while I worked at JP Morgan) and it was the first major writing project that I had ever finished. It got a couple of good reviews in the screening process but it ended up getting rejected. I had confidence with writing for the first time in years and felt as though I had something to live for again.

A month later, I started NaNoWriMo which is an online literary project for wanna-be writers when you write a 50,000 word novel inside of a month. It took me nine days to write Jack Tripper Stole My Dog. And to this day, close friends of mine say that's the best thing I have ever written.

Here's the tagline:

Jack Tripper Stole My Dog is an odd family story, of sorts, about a man and the women in his life: his wife, his daughter, and his lover. His life is filled with a long history of lying, cheating, gossiping, infidelity, hijinks, rape, incest, war, turmoil, some reflection and eventually unfolding into torture, murder, revenge and redemption. Add to the mix a half of dozen scorned lovers, psycho stalkers, several literate and pugnacious lesbians, George Bush, interstate serial killers, the KGB, canine tossing, taxi driving hitmen, one horny Ecstasy popping Hollywood Director, a drug peddling Mossad Agent, Chicks with Dicks porn, Bill Gates, suicide, date rapists, the Russian mafia, bad hippie bands, a bizarre and sick love triangle, junkies and drunks, trick turning Catholic high school girls, broken hearts, Jesus Freaks, swinging Upper East Siders, Internet lies and disinformation, a transvestite hotdog vendor, John Lennon murder conspiracy, the impending Russian-Chinese War, drunken frat boys and spoiled sorority girls, a corrupt heroin smuggling Reverend, Julia Stiles movies, and of course the CIA. That makes for a comedic and existentialist journey called Jack Tripper Stole My Dog.

I was writing again and in 2003 I decided to get back together with Betty. The sun was shining in my world for the first time in two years. Sure my job sucked but I started writing on the weekends and during my free time and started gambling with the stock market. We were on the verge of invading Iraq and I took advantage of my position as a broker and ended up taking a nice profit off the table during that short period when the stock market boomed. War is good for Wall Street. Coupled with an excellent run of gambling on the March Madness tournament, I was ecstatic. It felt good to gamble and write again.

Just when I thought I turned the corner, I had to deal with another tragic event in my life. It happened three years ago this month and only my friends and a handful of bloggers know what went down. I won't discuss the morbid details here, but I lost someone who was very close to me. And it hurt so much that all the drugs, liquor, and religion in the world couldn't make the pain go away.

I went on mega tilt. I got fired from JP Morgan and I started drinking in bars in the mornings. I was 190 pounds of walking misery and I did everything to numb my feelings. I spiraled and spun out of control. I had writing to help cushion some of the pain, but the rest of the time was unbearable.

I'm 100% sure I would have never made it if I didn't discover a way out of that depression. After drinking too much at the Cedar Tavern on morning, I boarded a bus to Foxwoods Casino. A couple hours later, I had sobered up and found myself sitting down at a $2-$4 Limit Texas Hold'em table. For the rest of that day, I felt somewhat normal. I was relaxed. Calm. And focused on playing my hands spending more time thinking about what cards the old guy in the Red Sox t-shirt held in his hand than thinking about how sad I was or the fact I was unemployed and never told anyone except Derek. For a few hours, the weight of the world and my depression had been lifted off my shoulders.

I went home after that trip and ended up writing Sweet Nothing (a.k.a. The Baby & Winky Novel) in less than ten days. It was a fucked up story about two fucked up characters that my friends loved reading about in short stories. I decided they deserved a full novel and some of my friends think that's some of my best writing. It features one of the best passages I have ever written:

There were a couple of seconds after she stabbed me and before the blood started squirting out where Baby and I calmly stared at each other. Our glances lovingly locked onto one another and we had a tranquil moment. Our symbiotic original connection only lasted for a second maybe two, but it was one of those eternal seconds that seem to last forever and you never want to end. It's those eclectic moments you come across while thinking about life's odd idiosyncrasies, while stuck in a sullen slouch at the end of a bar, drinking away the roughness of the day's grind. Or perhaps that treasured moment comes to mind while staring out the window of an airplane, your eyes bouncing back and forth between the clouds and the endless horizon and your shared memories burn a hole in your pants pocket, like a firecracker with a slow fuse that you lit years ago and simply forgot it was there until one day, POP! It goes off. And as our still bodies breathed together and our moment ended, all serenity vanished and I saw panic, fear, desperation, anger, and redemption jump on top of each other in a scrum and hide behind the pupils in her sky blue eyes. Simultaneously, heavy drops of tears rained from her swollen eyes as intense globs of menacing red blood bubbled out of the two inch cut on my bicep, forming an oval pool on our Salvation Army bought $18 couch.

The Baby and Winky book could not have been written at any other time of my life. And I'm glad I did it. After writing two novels and a screenplay in less than a year, I felt like a had a purpose again.

Aside from writing or getting wasted, I discovered something that I enjoyed doing immensely... poker. The more poker that I played, the less time I had to worry about my life and allow those negative feelings to haunt me. I switched vices. Poker took priority over drugs and alcohol. I played in clubs in the city and headed to Foxwoods, Mohegan Sun (when they still had a poker room), or to Atlantic City.

I began to write more frequently especially about poker. My friends got pissed that the Tao of Pauly was cluttered with too much poker content and they begged me to start a new site... the Tao of Poker. That was in August of 2003. And since then you pretty much know my story.

... to be continued


Editor's Note: If you have not read the first four installments, then visit...

Born to Gamble Part 1: Where It All Begins
Born to Gamble Part 2: Southbound
Born to Gamble Part 3: Midnight Rambler
Born to Gamble Part 4: Ramblin' Man

The sixth installment will be published in a few days.

When Senor moved to New York City in the mid-1990s, all hell broke loose. He's Neal Cassady to my Jack Kerouac. He's Oscar Acosta to my Hunter Thompson. He's Lenny to my Carl. Although we were fraternity brothers from the same pledge class, we weren't close friends and were in different circles during college. That changed when he left chiropractor school in Atlanta and moved to Manhattan after his hand modeling career faltered.

I had just walked out of my job on Wall Street and started writing my first ever novel (that would remain unfinished to this day). I found a job as the manager of an adult video and novelty store called the Booty Shack located on the Queens and Long Island border. By days, I sold German pissing videos and purple dildos to sexually adventurous New Yorkers. By night, Senor and I were partying it up hard drinking heavily at bars in Murray Hill and trying to pick up horny chicks in AOL chat rooms.

We went on a lot of trips together. When you travel with other people, it's important that your personalities mesh otherwise you're doomed to have an ugly trip. Senor and I got along extremely well, and that's why we've traveled together over all these years. We're both self-sufficient and easy going, willing to do anything at any given point, yet disciplined enough that we would stick to a schedule and itinerary. We were both travelers and not tourists and always took that attitude with us no matter where we went.

We took an amazing trip to Europe and you can imagine the trouble we got into during my first ever visit to Amsterdam. The events of one night were captured in a story called Shooting Pool, which involves a pair of underaged French girls. Here's an excerpt...

Amsterdam
7 Aug 96

I was kicked out of the Holland Casino for a dress code violation. The Euro-trash uppercrust take their casinos seriously. My attire failed to meet the minimum specifications: clean dress shoes, pants, collared shirt, and a jacket and tie. After a quick glance at the patrons inside I realized that most of the men were well groomed and they were all wearing tuxedos. It was scene right out of a James Bond movie and there I stood at the entrance trying to get in, decked out in Birkenstocks, ripped jeans, and a NY Knicks T-shirt. It didn't help that I had been tripping on mushrooms for most of the night, and I decided the best thing to do before I came down was to play a few hands of blackjack, and maybe even find a poker game to sit in on... but I couldn't even get in the front door... More

That story is one of several thousand odd nights that I experienced with Senor. Shooting Pool summed up the kind of hijinks that we would get into on our trips. I used to send out an e-mail newsletter to our friends about our latest "misadventures" and at some point I would write something like, "It wasn't until the plane safely landed after skidding a hundred yards on the slick runway when Senor sheepishly mentioned to me that he was flying without pilot's license and dropped out of flight school after the first week."

No matter if it was Amsterdam, NYC, or New Orleans... we pushed ourselves to the limits of sanity and sobriety and back again. If there was anyone that I knew who enjoyed living in the moment more than me... it was Senor.

And we gambled too. We'd bet on college basketball and pro football through bookies. We'd also play the occasional poker home game at my apartment in Park Slope. We started going to the Connecticut casinos when Foxwoods and Mohegan Sun opened up. Senor's parents lived in Connecticut and we'd take the train to the burbs, then pick up his car to drive to the casino. We'd play blackjack all night and get stoned in the parking deck while Senor would do his $100 bet trick when he'd walk up to any table game, whether it was roulette, craps, or blackjack and bet a single $100 bet. If he won, he was up $200. He'd bet a Ben Franklin on Red or the Pass Line or play a hand of blackjack. And that's how Senor rolled...

It was at that point in our mid-20s where we raised the stakes that we'd gamble with. Instead of money, we began testing the limits of ourselves and our bodies and gambled with our lives. In many ways that sentence sounds more dramatic than it was because at the time we were just living and living on the edge was all that I knew. But the more I think about what we did in the 1990s, the more I realized how lucky we were that we never ended up dead or in jail. We managed to avoid hospitals and court rooms as I began to rack up material for a five or six novels.

We stayed up for days at a time partying and lived for a few years as functioning addicts. I dunno how Senor held down an 8-5 office job in Midtown, but he did and always showed up no matter how many doses of acid we took the night before or how late we were out drinking with NYU girls. My job didn't matter as much. As manager of the Booty Shack part of the job requirement was for me to be completely wasted on duty. I could go on and on about that time in my life... but then you wouldn't buy the book.

I gambled pretty heavily on the March Madness tournament every year. That's how I made the bulk of my income. If I won big, I'd have a fun summer and use my winnings to travel to some place exotic with Senor or see a bunch of concerts or go to Jazz Fest in New Orleans. If I lost, it was going to be a boring summer in the city while I sold anal lube to bored Long Island housewives and wrote pretentious poetry in my spiraled notebooks.

At some point I met a green and orange haired Suicide Girl named Zoe and moved out to Seattle to live with her. Getting to Seattle was another one of Senor and mine's epic misadventures. It started with me going out to the middle of Pennsy-tucky to visit Derek who just graduated college. He was friends with a non-pot-smoking Jamaican guy who was an ex-Army sergeant and worked as a prison guard at Lewisberg Federal Penitentiary. That's where the 1993 WTC bombers are held.

Anyway, Derek's friend fixed up cars and sold me a 1984 Chrysler Le Baron that I purchased with my March Madness winnings. It was a non-convertible and we joked that it was "Jon Voight's car" from that episode of Seinfeld when George though he bought the actor's used car. The car didn't have a working stereo and the AC sucked camel balls. But we made due and drove all the way from NYC to Seattle. We'd have the windows down most of the time and whoever rode shotgun held a mini boom box which was our only entertainment. We played every Grateful Dead bootleg in my collection as we visited friends in different cities along the way.

We got drunk and snuck into the fifth row at a Cubs game at Wrigley field in Chicago. We tried to pick up girls from the local high school volleyball team in Kearney, Nebraska. We played hackey sack in the end zone of Folsom Field in Boulder, Colorado. We ate mushrooms in Laramie, Wyoming. We almost broke down in Jackson Hole and had to spend the night. Senor got into a fight with a bouncer at a cowboy bar across the street from out motel. We got thrown out and were lucky to leave Wyoming with only a few scrapes.

We headed through majestic Idaho and wide open Montana before we got to Spokane. We spent the night in Spokane. There was a dentist's wife who lived nearby that I used to have phone sex with from time to time. I met her in a Motel 6 on the shady side of town, while Senor rented the room next door and ordered two escorts from the phone book. A mutual friend of ours would constantly order two girls at a time in NYC. He'd pick the better looking of the two and send the ugly one home. Sometimes he paid for both. So there we were, on a random Tuesday night in Spokane in $49 motel rooms, and letting our sexual deviancy loose like an undisciplined pit bull running around in a playground.

When we got to Seattle, Senor flew home and that's when things took a turn for the worse. One of the reasons I moved to Seattle was to be with Zoe, but that didn't work out. I think I was with her less than a week before we decided we made a huge mistake. She moved back to Bellingham while I stuck around Seattle. I could have gone back to NYC but I decided to stay. All I can remember about her was the pyramid of cigarette butts in her ashtray. She wore purple lipstick and the ends of the smashed butts would have a ring of purple on the edges.

Years later I realized that I knew that relationship was doomed and never going to work but I needed an excuse to leave NYC and Zoe was my out. That was a huge gamble to move to a city on the opposite coast where I only knew one person (my buddy from college Slinger) and I didn't have a place to live, nor a job. In those circumstances, you do your most living... when you say "Fuck it!" and move all your shit to some place completely different. That's when you find out what type of person you really are. I've always been independent and resourceful. And those attributes were put to the test. Luckily, I found a place to live within two days near the University of Washington and within a week I had two jobs.

"You reached the end of the line," Slinger would say about Seattle.

He was an East Coaster like myself and if anyone ever moved from East to West they understand the subtle and abrupt differences in mentalities from living in an East coast city like Boston or NYC, to living in a place like Seattle, which was more a small town that exploded into a huge city. I had a tough time adjusting to dealing with the West Coast flakiness at first, but after I got used to that way of living, I began to love living there, despite the rain. And it rained a shitload. When I moved there during the early summer, there was zero precipitation with bright blue skies and you could see Mt. Rainer from any spot in the city. Then one day in September it started raining and didn't stop for ten months.

My two years in Seattle were vital for my personal development as a person and writer. I had to leave familiar surroundings and do my own thing for a period of time while I sculpted my voice as a writer and I explored myself creatively unfettered from the criticism of my peers and without any of the prejudice and negativity that my family bombarded me with after I left Wall Street. I guess in their eyes, I flipped out. I graduated from a good college, walked out of a perfect and high paying job, stopped shaving, grew out my hair and worked in a porn shop before I moved out to the Pacific Northwest which is the serial murder capital of Western Civilization.

I was the hardest working slacker in Seattle in 1998. I held four jobs and I humped two crappy hourly wage positions. I had been making six figures on Wall Street and I gave it up for the Bohemian lifestyle. And yes, my bed was a mattress thrown into the corner of my room that I bought off a guy named Crackhead Stu for $20.

I read a ton of books and people whom I worked found out I was a writer and they would give me books. I never had a shortage of reading material and I discovered a couple of writers that I never read before like Chuck Palahniuk, Carlos Castaneda, Alan Watts, Joseph Campbell, David Sedaris, and Philip Roth.

Most of the time I sat on a huge couch scarred with burn holes on my porch with my housemates. We'd make fun of the sorority girls jogging by and watched the steady rain while we chain smoked and elicit sympathy from one another about our depressing childhoods and hopeless futures. Sometimes the rants would be politically driven. Slackers and hippies had opinions on everything including the government's coverup of UFOs and widespread usage of mind-control drugs. We'd share our disdain and scorn for the suits in Hollyweird or the fucktards that ran the major music labels. They were both guilty of ignoring originality.

Sometimes we'd drink micro-brews, pop too many pills, and play really bad music in the basement of our house until sunrise trying to become the postmodern reincarnation of the Velvet Underground. But that never happened because we were unmotivated ganja smoking wanna-be musicians and the melodies reverberating from my guitar sounded more like two frogs dry-humping each other on a squeaky stairway.

I also drank exclusively at the Blue Moon Tavern a few blocks from my house which had been frequented by other literary greats such as Ken Kesey and Allen Ginsberg. I hoped that by pissing in the same urinals that they pissed in and by sitting on the same bar stools that they sat in would miraculously make me a better writer. Tom Robbins described the Blue Moon as "a frenzy of distorted joy spinning just outside the reach of bourgeois horrors."

That summed up my time in Seattle.

I focused on writing and spent hours and hours every week holed up on my room sending off articles for submission in various literary magazines. Everything was rejected and I started hanging up my rejection letters on my wall, so when I left my room everyday to go out into the real world, I was reminded that I was a failure and that my biggest priority of that day was to improve my writing skills. After a while I stopped hanging up the rejection form letters because there was no more room left to hang them.

My buddy Slinger and I decided to write a screenplay together and for five or six months, we were diligent. He waited tables downtown and I'd come by after work to see what he wrote and I'd give him my pages. We both had no idea what we were doing and we spent most of the time drinking beer and smoking weed while discussing the screenplay with the Marnier's game on in the background. We never finished the script because Slinger got a job as a beat writer for a small newspaper in Florida and left Seattle. That screenplay became one of forty projects that I began in the 1990s and never finished.

During March Madness I opened up an account with a sports book on the island of Curacao. I funded it through Western Union and got a 100% deposit bonus. My buddies would place smaller bets using my account. After the second day, we were all broke. We had to fund my account three more times before the tournament ended. We all lost heavily that year but it was a lot of fun despite the fact we were complete degenerates.

The first time I ever played Texas Hold'em was in Bellingham when Slinger took me to the Nooksack Casino. We called it the "Nut Sack" and Slinger used to play there when he lived in Bellingham with Dutch a few years earlier. Dutch was the same guy who used the infamous "Dutch Bucks" in Jerry's homegame in Atlanta. Slinger and Dutch would play Hold'em there everyday after work. Slinger even won a few tournaments there. They quickly got me hooked on the two card poker game.

In Seattle, we occasionally played cards at Slinger's apartment with his roommate Ty who worked at a swanky bar and restaurant downtown. Some of Ty's co-workers lived in a house in Fremont and they held a home game every Monday. On the West Coast, Monday Night Football started at 6pm and that year they began it at 8pm EST or 5pm PCT. So the home game would start at halftime in the kitchen of the Trout House. They nicknamed it the Trout House because several members of the acid-jazz band Kilgore Trout lived there. They would practice in the basement and we could hear them during the games. When practice was over, the guitar and sax player would sit in and play with us.

We'd drink Labatt's, smoke weed, listen to great music, and tell dirty jokes. In short, we had a blast and since I worked weekends and had Mondays off... it was the one day of the week I couldn't wait for. The games at the Trout House were some of my favorite home games of all-time because everyone who played in it was pretty cool and we didn't mind losing money to one another. Mostly everyone had dead-end jobs either as line cooks or bartenders or waitstaff which meant everyone had cash to play.

We had some good players and the games were dealer's choice. We'd buy in $20 or $40 to start and it would not be uncommon to rebuy a few times. We played a lot of Stud and I introduced a game called 75 Cent Mexican, which is a variation of Midnight Baseball or No Peak. Ante was 75 cents (which was 3x the normal ante) and each player got dealt seven cards but you cannot look at them. 3s and 9s are wild, you can buy a card if for 75 cents if you have a 4. You turn the cards one at a time and have to beat the hand of the player showing. If Ty turned over a Queen to start, I'd have to keep turning over cards until I can beat his Queen. Let's say I have an 8 then a 9, then I'd have a pair of 8s and Slinger would have to turn over his cards one by one until he can beat that hand and so forth. You bet after a player makes a hand and these pots would swell up. It was the highlight of the games and I became a legend at the Trout House for creating the action game 75 Cent Mexican. The guys in the band loved the game so much, that they wrote a song with that title.

In 1998, the film Rounders came out and I saw it three times at the Neptune Theater in Seattle. We introduced Hold'em to our homegame and at first we kept making mistakes on what cards to burn. Yeah we were total rookies, but we thought Rounders was the greatest movie in the history of cinema. Little did I know that the film would affect millions of other poker junkies around the world.

Later that year, Phish played two monster concerts in Las Vegas including one on Halloween when they covered the entire Velvet Underground album Loaded. As soon as the shows were announced, Senor and I both knew we were going. I actually began my Las Vegas book with that scene. What you are about to read has not been seen by anyone, except my assistant Jessica who helped edit the manuscript for me. Enjoy the teaser of the first three paragraphs of my Las Vegas book...

Sometimes you get lucky before you even set foot on a plane bound for Las Vegas. I should have been arrested on the spot at Sea-Tac airport. Instead, I talked my way out of fines and imprisonment. More importantly, I avoided a huge legal tab from a over-priced criminal attorney wearing an off-the-rack suit whose sole job would be to try to find loopholes in my multiple drug possession charges. Sure, my good friend Senor was a high priced attorney in New York City but he had no juice on the left coast. All he could do was pick up the phone and hope that he could find a former law school chum in the greater Seattle area who owed him a favor. Otherwise, I'd be fucked. Properly.

1998. I was a long-haired cynic living in the slacker life Seattle trying to write screenplays while I smoked too much pot, slept with bored housewives from Vashon Island, and sat in bars listening to rambling dissertations from too many West Coast philosopher types, many of which I considered my close friends. That was back in a time way before airports took security seriously and you could travel with a horde of drugs on your person and not think twice about taking the risk. I had an ounce of high grade marijuana in my left pocket. In my right, a half an ounce of magic mushrooms was concealed. My sole job on that particular mission was to bring as many drugs as I could down from Seattle to Las Vegas.

My small backpack was filled with a long sleeve shirt, a Hawaiian shirt, two pairs of underwear, socks, my notebook, two pens, a Spalding Gray book and my toiletries bag. With memories of Billy Hayes stuck in a Turkish Prison from Midnight Express bouncing around my head, I double wrapped the drugs in Ziplock baggies. The mushrooms were small and odorless. That package was about the size of my wallet which I shoved into my front right pocket along with my wallet. The pot reeked. Badly. The more pot stinks, the better it is. I did my best to conceal the smell of some of the best shit I smoked in over a year. That package was about the size of a John Grisham novel. I wore cargo pants and it fit perfectly into one of those enlarged pockets.

As I walked through the metal detector, a guard who looked like Cheech Marin stopped me when the buzzer went off...

... to be continued


Editor's Note: If you have not read the first three installments, then visit... Born to Gamble Part 1: Where It All Begins and Born to Gamble Part 2: Southbound and Born to Gamble Part 3: Midnight Rambler. The fifth installment will be published later this week.

I left Atlanta a couple of months after graduation, with a few grand in my pocket after a successful summer of poker and blackjack. I drove back to New York City without a job, nor a place to live. I really didn't have a clue to what I was going to do with my life. A few months earlier, I applied to NYU film school and I was quickly rejected. The previous summer, I was the ice cream man in Atlanta. I wrote a screenplay that was a taut psychological drama about an ice cream man who couldn't sell ice cream on the hottest day of the year. It was Do the Right Thing meets Taxi Driver and I figured that my cinematic gem was going to get me a scholarship to film school and a three picture deal with Miramax. My screenplay was rejected and so was my dream of going to film school to become the next Richard Linklater or Quentin Tarrantino.

The job market was at an all time low for the mid 1990s and I was one of hundreds of thousands of college grads migrating to NYC to find work. I took my LSATs and did extremely well. I figured law school was a distant option since I had not yet applied. I thought about getting my old job back at the Commodities Exchange, but I was reluctant. I wasn't ready to throw on a suit and tie and my four-year slacker lifestyle seemed more appealing. I took a menial job at the Metropolitan Museum of Art. Within a few weeks I met a sultry French chick with big brown eyes and I moved into her loft in Chelsea that was inhabited by rats and her two roommates, both drag queens. I was in a holding pattern until I figured things out, which meant I got shitfaced every night and followed the Grateful Dead around until Jerry Garcia dropped dead.

I grew up in New York City during my childhood, but the city is completely different when you were 21 years old and being reintroduced to it for the first time. I returned just before Giuliani cleaned up the city. There was still a slight edge to it and the cooler parts of town weren't overrun by hipsters, dotcommers, and the Starbuckification of America.

I ran rampant through the streets of my city like a horny Russian sailor on shore leave in Bangkok for 48 hours. I viciously tortured my brain cells and went on a year-long bender that would make Ted Kennedy proud. I spent many late nights getting trashed in dive bars in the East Village and in Brooklyn. I'd puke in between subway cars and pass out on people's couches that I had only met a few hours earlier. I was "young, dumb, and full of cum" and raising hell with some of my co-workers, who were an odd cast of peculiar painters, narcissistic actors, progressive musicians, understated sculptors, and hackneyed poets. They were what and who they wanted to be and didn't let a day job nor society define their existence.

I learned from their devout dedication to their crafts that it was going to be at least ten, possibly twenty years before I began to fully understand and master my craft. I had a life-altering decision to make: if I wanted to be a writer, I had to be willing to choose a life of sacrifice with the knowledge that what I was attempting had astronomical odds against what I was trying to achieve. Millions of people begin their careers trying to do something with their art and talent, but only a small percentage earn a living wage doing it and most of the time it's a sheer compromise that they have to endure in order to earn a living as a writer, painter, or musician.

I also discovered a group of hard-core gamblers at the museum. My friend Marco was a security guard in the Classical European paintings section. He introduced me to OTB's betting by phone feature. We set up and funded my account at the local OTB and then I was able to use their automated system to phone in bets on horse racing. I would do this during work hours! I worked with a lot of union guys who had mob connections. And everyone knows that horse racing is fixed. When we'd get word of a "sure thing," we'd bet heavily on our tip. It only had to hit 1/3 of the time for us to break even.

One day Marco had a tip but didn't have any money in his phone account. He had to go to the OTB and put in the bet directly, so he called his supervisor and told him that he was taking a ten minute bathroom break. He left his post in the Caravaggio Room at the museum, hailed a cab on Fifth Avenue and told the driver to take him to the nearest OTB 15 blocks away. He jumped out, placed the bet, then jumped back into the cab and ran back into the museum. He returned thirty minutes later dripping in sweat. When his supervisor wondered where he went, he explained that his trip to the bathroom turned into a nasty case of explosive diarrhea and was stuck shitting his brains out.

I met another guy who ran the football betting slips ring and sold dime bags of weed on the side. I'd gamble with the same parlay slips that my father had given me ten years earlier. I also worked with a bookie, and I bet on college basketball and pro football. I would classify my sports betting as moderate to low at the time. Living in NYC was expensive especially since I went out to party every night.

My buddy Stormy (who just won a seat in this year's WSOP main event) and I would organize poker games with some of the security guards. We'd play at Marco's apartment in Peter Cooper Village or at my apartment in Park Slope. I introduced Four Barrel to the home game and they were hooked along with other games such as Acey Deucey. The games started out low stakes and by the end of the night it would get ugly when we'd play Four Barrel. There was a group of seven or eight of us that rotated in and out of that game for over a year. I won more than I lost and the games were more social than competitive.

I also heard about the illegal poker rooms for the first time although I never played. I went to one once with Marco around Union Square. He went a few times with one of the ex-cops who worked security at the museum. It was a private club and you could not get in without being introduced by a member. Marco just got his membership card and was going to get me one. They only had one table running (Seven-card Stud) and we didn't want to wait. I never went back.

Around that time I started going to Atlantic City to play blackjack. It was a two hour bus ride from Manhattan and we'd arrive around Midnight. I counted cards and Stormy, Marco, and I would buy $25 roundtrip bus tickets to AC. They'd give us $20 in free play at the casino and we discovered a scam where we could cash it out at Sands, so the roundtrip would only cost us $5. We'd play blackjack all night and comeback the next morning.

I first sat down at a poker table at the Taj Mahal because I was down to my last $30 after getting seriously cold-decked at the blackjack tables. While I waited for the next bus back to the city, I sat down at a $1-3 Seven-card Stud table where I was about forty years younger than the other players. Since the Taj's poker room was close to the exit, I could step outside and smoke a couple hits off of a blunt and not miss too many hands. I'd joke around with the infamous Atlantic City hookers who mingled in the same area. That's when one lady of the night uttered one of my favorite phrases that I have ever heard from a hooker, "Honey, if you wanna fuck Big Momma, you better wear a space suit," as she lifted up her pink mini-skirt and pointed to her crotch, "Cause you ain't getting out of this black hole alive."

I had no clue what I was doing at the tables since I never read a poker book. I played by instincts. I had home-game experience where we played Stud frequently. With an excellent memory, almost photographic, I could easily memorize what cards were already out. I relied on my ability to read people and had no knowledge of advanced concepts. I played fairly tight because I didn't have much money to gamble with, so I didn't play too many pots.

At first I didn't understand the commonality of tipping poker dealers. Like blackjack, I would tip out a dealer when they left the table. Fortunate for me, the other players at my table were friendly and clued me in on the proper etiquette. Some of the WWII vets gave me free advice on playing Stud, like how I should always complete my bet with an ace out there and about not giving other players on a draw free cards.

After a year of heavy partying, I grew tired of living the hungover life of the village drunk from an Irish novel. I eventually decided that I wasn't willing to fight the overwhelming odds to try to be a writer. I was at a fork in the road, and took the easy way out. I became a suit and quickly found myself trading bonds for a brokerage firm located on Wall Street.

Part of that decision to head to Wall Street was due to the fallout over horrible relationships that I had with two particular women during my first year living in New York City. Frustrated, heartbroken, and lacking any self-worth, I needed something to take my mind off of the misery. Long hours in the trenches trading New Jersey sewer bonds provided that escape.

I always fall for the wrong women. I should know better, but I can't stop it. I have a weakness for emotionally disturbed women. I barely survived the hellish period when I lived with a self-hating, chain-smoking, French painter. Then I dated a strung-out, chain-smoking, Belorussian model. One despised men so much that I wondered why she wasn't a lesbian. And the other one was so fucked up in the head and mercilessly addicted to cocaine that she made me seem like Richie Cunningham to her Courtney Love. Of course we ran off to Jamaica together to live in Paradise but that didn't work out very well. You can read about that drama in my book Gumbo. Here's an excerpt:

"I massaged Natasha's smooth hair and she rushed in for a kiss. I brushed her left cheek with my hand and she took it and kissed my fingers one by one. She closed her eyes and inserted two fingers into her soft mouth and began slowly sucking them. When someone knocked on the locked bathroom door, she clamped down hard and bit me. I screamed and with my first impulse, I punched her in the head with my free hand and pulled my fingers to safety. She laughed as I inspected my right hand and saw teeth marks impressed into my flesh, but no blood..."

I was a scorned lover, dead broke, and my soul was bankrupt. I was a perfect candidate to be brainwashed and I quickly fit in. I was recognized as the best trader in my class and won Rookie of the Year at my firm. I don't think I was exceptional, rather I got lucky and put in rigorous hours, upwards to 80+ a week including Sundays.

The financial markets are a form of legalized gambling. You're speculating the future. I got paid to gamble... with other people's money. And it was tons of fun except when I was wrong which happened more often than not. The rush was overwhelming and the work was exhilarating. In many ways I miss those aspects of my day, when you get so jacked up on adrenaline that it feels like you are floating several feet off the ground.

The guys in my office were smug assholes. In many ways, they deserved that right to be cocky. What they did mattered much more than the other suits and skirts scattered in offices and cubicles all over Manhattan pushing paper, where a bad day for them was getting chewed out by their boss or blowing a sales presentation. In the trenches on Wall Street, a slip up could cost millions of dollars. People get whacked for those sorts of mistakes. An error in judgment by a rogue trader or broker could ruin an entire company or an entire country. Yeah, the guys I worked with were pompous snobs. They thought they were Gods among men. Big Swinging Dicks. Masters of the Universe. And I was one of them.

... to be continued


Editor's Note: If you have not read the first two installments, then visit Born to Gamble Part 1: Where It All Begins and Born to Gamble Part 2: Southbound. The fourth installment will be published later this week.

"Like most New Yorkers, my family did not believe that a glass of beer or a game of cards imperiled their souls, and there was something ugly and silly about those who insisted they did." - Edward Conlon, Blue Blood

When my internship at the NY Commodities Exchange ended in late May, I was offered a full time position with the brokerage house that I had been working with. At the age of 17, I made $500 a week plus overtime. That seemed like all the money in the world to me. (The sad part is that a decade later at age 27 as a struggling writer and artist, I'd make substantially less per week including inflation than when I was 17.)

I picked up at least $40 a day in prop bets on the floor of the exchange. For $20 a pop, I'd make crank calls to brokers' ex-wives and ex-girlfriends. I'd willingly say things like, "How would you like to make $14 the hard way?" or "How many cocks have you sucked today, you dirty slut whore?"

Most of the time, I pretended to be a doctor suggesting that one of their ex-lovers tested positive for the AIDS virus and that they should get tested immediately. It was a fucked up thing to do, but I was 17 years old and that was probably the least crazy thing I did. After work, I would go to the bars with the other brokers and clerks. Yeah, I wish I was 17 again drinking $1 mugs of beer at the Dugout in the East Village and trying to pick up rich stoner girls from schools like Fieldston or Chapin.

During my last week of work in August of 1990, the markets went completely crazy. The stock market and gold market were at new highs and oil futures went through the roof when some insane guy in Iraq named Saddam invaded an oil rich neighboring country. That was the first time I understood how international politics and war affected the financial markets. I saw it with my own eyes. During the seven months I worked on the floor, I never witnessed that much chaos as I did when Saddam attacked Kuwait. Everyone who had an account was gambling on the future. War is good for the economy and everyone was trying to position themselves to earn as much (or lose as little) money as possible during the impending showdown in the first Gulf War.

"You're lucky you're going to college," my supsenders-wearing boss with slicked back hair told me, "otherwise they'd be shipping your ass off to the desert."

* * * * *
Parts of college were a blur for me. I blame the mushrooms and Jim Beam, which caused partial memory loss. I didn't learn all that much in Atlanta while I dabbled in hedonism for four straight years. Although you can make a solid argument that 16 years later, I'm still caught up in my Dionysian lifestyle. The foundation of my intellectual knowledge was given to me by the Jesuits who taught me a classical education in high school which included learning four languages (Latin, French, Russian, and Greek), while studying Russian, Victorian, and early American literature, Advanced Calculus, Economics, and four years of theology.

Since my prep school was so rigorous academically, my classes in college were a joke. I took classes like Bowling, Stress Reduction and Flexibility, Social Problems in Modern Society, and the Presidency. No wonder I'd show up to class stoned, drunk, or both.

I wasn't challenged. College reminded me of watching Wheel of Fortune just after watching Jeopardy. It was a waste of time. I spent less time in classes and most of my time drinking in Atlanta bars, sitting on the porch of my fraternity house make cat calls at the sorority girls who jogged down Fraternity Row, or roadtripping to New Orleans or following the Grateful Dead throughout the South.

I also gambled in my late teens. Heavily.

My fraternity held a football pool and a March Madness pool, and I was in contention for both every year. I won the March Madness pool when UNLV beat Duke and guys in my house were verbally abusing Christian Laettner as they shouted homophobic references at the TV about his "close relationship" with point guard Bobby Hurley.

Most of us gambled on football every weekend. I had a bookie back home in NYC. Karate Tony started his own book during college and we used his services. My buddy Chicago Bob had a bookie in Atlanta and we'd phone up both bookies and go with the one who had the better spread. During my senior year, we had an amazing run and won seven weekends in a row. I have still yet to match that rush.

Sometimes on weekends when there wasn't anything going on, we'd roadtrip down to the riverboats in Biloxi, Mississippi to play blackjack. That's the first time I played poker in a casino, was on a riverboat. I was down to my last $30, so Chicago Bob and I played Seven-card Stud with a bunch of WWII vets.

During senior year, eight of us rented an RV and drove to Mardi Gras. We parked the large beast on Chartes Street in front of a church and went on a three day bender which included the consumption of massive qauntities of liquor, narcotics, and groping half-naked college girls from Texas. On the way back to Atlanta, we stopped off in Biloxi and headed to a riverboat casino. We needed to win enough money at the tables to pay for gas for the ride back.

My friends and fellow fraternity brothers started asking me to place bets for them. I would phone in their bets to Karate Tony or Chicago Bob's bookie. They lost more than they won and I started booking their action... myself. I stopped passing the bet along to Karate Tony unless it was so huge that I was afraid to cover it myself. Although I had one or two problems collecting money (and it was always from the rich kid who drove a nice car that refused to pay), I made enough scratch that I quit my part-time job cold calling alumni for donations. At best, I was a low level thug making a couple of hundred bucks of the degeneracy of the rich kids in my fraternity who would drop $100 on the Eagles because they were rooting for their hometown Philly team and betting with their hearts instead of their brain. All my bookie money went to pay my bar tab at Dooley's Tavern and to pay for tickets to Grateful Dead shows.

We played cards all the time in my fraternity house. There was a period of time when everyone played Spades and we even had a house-wide tournament. Spades is played with four players comprised of two-person teams. Rib was my partner and we were one of the best teams in the entire house. We would spend hours and hours playing and drinking cheap beer and smoking bad weed while listening to Widespread Panic bootlegs on the stereo in Rib's room.

We would play drinking games with freshmen girls who would wander down to the house. We'd try to get them hammered drinking Malibu Rum or some other conncoction that I came up with... lemonade and Southern Comfort. We'd play Asshole most of the time and some of the girls would be doing the "Walk of Shame" sometime around 8am.

We also played poker in college and the games were intense. We'd play in the living room of our fraternity house. One weekend we had a huge party where a band played in the formal room. After the party ended, we left the stage there for a week maybe longer. We threw green felt over one of the dinner tables and we started a poker game. That game lasted for a week straight as brothers and friends of ours would sit down and play rotating in and out. It was our version of the Big Game. Playing up on the stage under the bright lights with a small crowd gathered around made the players in the game feel like they were doing something extra special. We'd drink Jim Beam like it was water and chug Beast Lite, tossing empties into the fireplace or out the window. We made pledges go fetch us food, buy us more liquor, and clean out the gravity bong for us. Guys were afraid to go to class, take a nap, or have lunch with their girlfriends because they were worried they'd lose their seat in the game.

When it got too big we moved the game off campus. One of the dorky brothers in my fraternity complained that we were gambling in the open and that we could get our charter revoked for such aberrant behavior. It was just cards and not a big deal, but we got yelled at anyway. I thought it was a hypocritical decision since our other degenerate behavior was still allowed like the rampant drug abuse, giving our pledges alcohol poisoning, and the occasional date rapes.

My buddy Jerry lived off campus with Rib and his three-legged cat, Smooth, that was addicted to marijuana smoke. I guess if you were missing a leg, you'd get stoned all the time too. During the spring of 1994, two NYC teams were in the playoffs. The Rangers ended their 44 year drought and brought home the Stanley Cup. And the Knicks were bounced by the Houston Rockets in the NBA finals after John Starks went 1-87 from the floor in game 7.

Every night for a month straight, a NY team was playing in the playoffs so there was a different game to watch on TV. We'd be huddled around the TV and when the games ended, we'd play poker until sunrise. There would be 14-16 people playing with two tables going. The girls who lived across the hall got hooked. This went on all summer long.

We played dealer's choice with the emphasis on a four card guts game called Four Barrel where 4s and 8s were wild and flushes and straights don't count. Those games would get ugly and it would not be uncommon to lose a couple of hundred dollars in a Four Barrel pot. This was a lot of money considering we'd start out the night with nickel and dime antes. Even the sorority girls across the hall were hooked on Four Barrel. The second table would break around 2am when the people with "real jobs" had to crash. The first table would continue until sunrise when we'd go back to campus, pass out, then wake and bake and start the routine all over again.

I didn't work at all that summer. During Memorial Day, I went on a rush and won $2K playing two hands of blackjack at the same time at the Casino Magic in Biloxi. I made enough money to cover rent and food for the entire summer. I guess you can say that my first job out of college was being a professional gambler.

One guy in our game had spiraled into in a big losing streak. Dutch lost so much money that he had to use IOUs, which he scribbled on yellow Post-It notes. We nicknamed those IOUs "Dutch Bucks." They were as good as gold. My friends and I would use Dutch Bucks as currency. If Jerry bought me a twelve pack of Beast, I'd pay him with $5 in Dutch Bucks. At one point I had almost $200 in Dutch Bucks and I traded that in for a free round of golf (cart included) at Pinehurst, NC, a ticket to a Phish concert, and a big bag of mushrooms.

We'd all bring cash or jars of change to play in Jerry's homegame. Dutch would bring Post-Its. I still have a few Dutch Bucks to this day.

One night Teddy B (our version of G-Rob) got so drunk that he gambled away gift certificates that his girlfriend gave him for his birthday. She was still in school and didn't have much money. She knew Teddy B loved watching flicks, so she bought him $50 in gift certificates at Blockbuster. He was stuck pretty bad one night trying to bluff at a big pot in Four Barrel and "Zeke" got the best of him. He didn't have cash to buy back in and busted out the book of gift certificates. He promptly lost every single one. When his girlfriend found out she was furious. When we offered to give them back, she refused to accept them.

"Don't give them back. Let him learn this valuable lesson," she said. They broke up soon after.

... to be continued


Editor's Note: FYI, check out Born to Gamble Part I: Where It All Begins if you haven't read it already. Part III of the Born to Gamble series will be posted on Monday.