Iftarii (BB): 21,579 (134.9 bb)
JeevesGets (SB): 18,421 (115.1 bb)

Preflop:
JeevesGets raises to 320, Iftarii (8♠️7♠️) raises to 1,120, JeevesGets calls 800

Flop: (2,240) 4♠️6♦️5♠️
Iftarii bets 1,500, JeevesGets raises to 17,301 and is all-in

As my cursor moved towards the call button, TJ looked at me, incredulous. The ultimate opportunity for a slowroll had arrived; was I really about to waste it? I was not.

The tournament gave each of us a ten-minute time bank for the entire event.

I spent the next five minutes in some sort of sadistic euphoria.

Iftarii calls 15,801
JeevesGets reveals 4♣️5♣️
Turn: (36,842) Q♦️
River: (36,842) 7♣️

A little while later, I received a message from a new user in my AIM window.

anon_44 (5:56:54 PM): listen u *******
anon_44 (5:57:00 PM): if i ever meet u I will try to kill u
anon_44 (5:57:03 PM): i dont care if u kill me first
anon_44 (5:57:09 PM): you deserve to be murdered and torutrued for that
anon_44 (5:57:10 PM): i am serious
anon_44 (5:58:13 PM): im coming to ma now
anon_44 (5:58:17 PM): you deserve to be ****ing murdered
anon_44 (5:58:27 PM): and everyone in your ****ing family deserves to get murdered you moron
anon_44 (6:04:43 PM): yea you better ignore me
anon_44 (6:04:56 PM): i dont care if ur bigger or stronger than me, i will ****ing murder and torture u or die trying
anon_44 (6:05:02 PM): ive never done a thing to u
Me (6:06:18 PM): whos this
anon_44 (6:06:28 PM): go **** yourself iftarii
anon_44 (6:06:36 PM): i will come to massachusetts and ****ing kill you
anon_44 (6:06:39 PM): ive never done ANYTHING to u
Me (6:06:58 PM): jeeves?
anon_44 (6:07:26 PM): what goes around comes around
anon_44 (6:07:28 PM): you are ****ing dead

Jeeves was extremely talented, and had plenty of ego to match, but that described me just as well. What bothered me about Jeeves was how fragile he was, and how easily he could lose his shit over the most minor and common occurrences. Jeeves (and a few of the other top pros of that era) was prone to detonating over any downturn in luck, and spraying his wrath at whoever had dared to get lucky. I’d grown up around explosive anger, and vowed never to become it. Heads-up can feel very personal, and everyone in those games wanted to vent when they ran bad. Most of us were sitting on plenty of anger and frustration. For better and for worse, I held mine, and I had a particular contempt for the guys who couldn’t hold theirs.

Slowrolling Jeeves was me exorcising some of my own darkness, and feeling self-righteous while doing it. Vilifying the guys who let their explosive anger out was also my way of not becoming one of them.

The rage expressed in that chat log was particularly egregious, but the heads-up ecosystem of that era could be a pretty toxic place. A few years later it would curdle into something a whole lot uglier than nasty chat logs.

If you’d asked me at the start of 2008 what I wanted, I could have given you the whole list without thinking: A girlfriend. More money. More recognition. That was more or less the wish list of a twenty year-old who thought he had himself figured out.

That year, I got all of it, more or less in order.

In April I met Brittany. We’d be together for the next six years. In June I finished fourth in the WSOP Heads-Up Championship, which put my name in the poker world for the first time and gave my bankroll a real boost. And in November, more than half a million dollars landed in my lap when I finished second at Foxwoods.

Tournament poker was never going to be my life, and I knew it. Going on tour to play tournaments meant a lot more folding than raising, a lot more busting than final tabling. I was accustomed to a game where I was playing 80% of my hands and winning more days than I lost. I wasn't cut out for all the patience and the pain that a life of tournaments requires.

A few weeks after I turned twenty-two, I bought a house, and what I wanted from it was simple: a place where my friends could come and hang out, crash for days or weeks at a time, and show up whenever they wanted. And they did. Friends were over constantly to grind, so often that I turned the master bedroom into an office and chose a smaller room for myself. But it wasn’t just poker. There were parties, beer hunts, wiffleball tournaments. I loved being around my friends and Brittany, and I’d built a place to keep them close.

Life was genuinely, uncomplicatedly good. I was making more money than most adults I knew, playing a game I loved, in a house that was generally full of the people I liked most.

I was starting to get used to this rhythm. I wanted things, I got them, and then I’d think of something new to want.

The slowroll against Jeeves only advanced me to the second round. I’d end up winning the next four matches and taking down the tournament for $315,000. I don’t remember how much of that went to me, but I’d be surprised if it was less than 80%. On top of that, I made another $300,000 grinding heads-up sit and go’s that year.

My poker ego, already sizable, continued to inflate. I’d made more money in four years than I’d hoped to make in fifteen.

In the pre-solver era, there were a lot of different ways you could be good at the game. My gifts were in pattern recognition and a willingness to test out creative lines.

The first stage was noticing how a play had made me think and feel, and then imagining my opponent arriving at similar thoughts and feelings.

Stage two was building a strategy to exploit those feelings, nudging my opponent toward the decision I wanted him to make.

In 2025 Ben Tollerene 1 described what it was like being on the other side of the felt: “You would take these lines that would push such strong feelings in me….You had a very strong affect in this way…I can remember you would take these lead lines….You would check call and just start leading and it made me want to do certain things, and I could feel the power in it.”

Stage three was the most rewarding: anticipating when my opponent was nearing his breaking point and was ready to snap. This meant staying attuned to the signs that my opponent had caught on to my strategy. And then, just as he was ready to adjust his play, I’d already be there, waiting for him on the next level with the counter to his adjustment. I tried to live one step ahead.

One of my favorite tricks was to take a bizarre betting line that was likely to provoke even a tight opponent into a bluff they’d almost never make. When I would catch them bluffing in these unique spots (where they had thought their bluff was rare and spontaneous), they would determine that I must be a calling station, and therefore not worth trying to bluff. If you can get your opponent to shut down their bluffing in a heads up match, your edge becomes insurmountable.

It was close to the end of the era where being gifted mattered more than being determined, where feel and instinct would still beat study ethic.

Rather than appreciate the good fortune of my gift, I leaned into what I felt it said about me.

There’s a version of this you already know if you grew up watching sports. The great athletes seem to lean into their ego, at least in the arena. Afterwards they’ll say humble things in interviews, and most of us assume they’re largely paying lip service, playing it safe. But in the moment, after a clutch three, a huge forehand, or a critical goal, they’re pounding their chests or pumping their fists, and none of it looks like gratitude. It’s saying ‘I’m the man, and we all know it’. Sometimes, guys like MJ and Kobe flexed even harder by trading that energy and passion for cool nonchalance and an icy stare. That sent an even stronger message: ‘you’re not me’. Many of us looked up to that. I aspired to it. And there’s a lot of dark shit wrapped up in that mentality that took me years to see.

But I think it’s a big part of why, when I won, I didn’t spend much time dwelling on how fortunate I’d been, or how well things had broken for me. To my way of thinking, that response was for a lottery winner, someone who’d been purely lucky that a jackpot had fallen into his lap. I wanted the other thing. I wanted it understood that I had done this, I made this happen, and it would happen again because it was skill, and skill is repeatable, whereas luck is random. Most poker players have a complicated relationship with what it means to be lucky. Being called lucky moves the focus away from what we’re proud of. I didn’t want that, so I behaved in ways that I thought would keep it on me.

The irony was that the gifts that made me a great poker player in 2009 probably wouldn’t have been enough to build a career on ten years later, and I wouldn’t have found any games to play ten years earlier. For me, the timing of the poker boom was about as close to a golden ticket as anyone gets. I was one of the luckiest people I knew, but I chose not to see it that way.

2009 was a year of enjoying the spoils and continuing to crush the high-stakes heads-up games online. And somewhere in there, a crisis I’d never seen coming arrived, one that looks completely obvious to me now. My goals and desires had been getting met so quickly, that I eventually ran out. I didn’t know what to want anymore. More money struck me as shallow and mostly pointless - obviously not a purpose but a distraction from the lack of one. I still liked gaining recognition, but I was nearing my ceiling. I played a fraction of the hours that my peers played, and I had no desire to change that. This dilemma caused me to ask bigger questions. Questions I couldn’t answer, or answered in ways I didn’t like. I wasn’t clinically depressed, but I was philosophically changed. I still took a lot of pleasure in life, in the people I spent time with, and the games and sports I liked to play. But I’d suddenly come to believe that each of these pleasures would eventually exhaust itself, and need replacing, and that was life. I found that utterly depressing.

One evening in early 2010, at our weekly dinner, I told my father about it. I’d been careful with these thoughts, treating them like something contagious, keeping them off my friends and away from Brittany. But my dad was older, and wiser, and a psychiatrist, and I figured there was nothing a twenty-three-year-old could bring to him that would hurt him the way I worried it might hurt everyone else.

He listened. He asked good questions. I felt heard, and understood, and I was completely deflated. The kid in me was still hoping he’d have the magic antidote. Some important piece of logic I’d missed that would hand me back a reason.

He didn’t. He told me it was hard, and that he’d gone through something similar when he was a few years older than I was. He told me that one day I’d have children, and that they would help fill a lot of the hole I was feeling. I had always wanted kids, but the thought only sank me further, because it just confirmed the thing I was afraid of. Distract yourself with goals, chase them, achieve them, repeat until you procreate, raise the little buggers, find a new pursuit, die. That was the shape he was describing, even in comfort. That was the whole thing.

The one hopeful thing he said that really stuck was that the most renewable source of purpose he’d found was helping other people. I’d been volunteering at a local nursing home for the past year, spending time with older folks who didn’t get many visitors. I think when I started, I was prompted by a feeling of obligation. A debt I felt I owed to society because I got to play a game for a living. After thinking about my father’s words, I began leaning into it for a sense of purpose. It wasn’t a cure. But it was a slow burn, something that didn’t exhaust itself the way everything else seemed to, and over the next couple of years it helped more than almost anything.

There’s something of a paradox in the timing of all this that took me a while to untangle. I’d started sinking into these existential questions in part because I’d gotten everything I wanted. But I think it was more complicated than just that. Right around then, two things I’d built my identity on fell apart at once: my profits tanked, and my status as one of the top players went into free-fall.

Holding down lobbies in one of the most competitive spaces in poker had built me an identity I was proud of: Iftarii. A name that was respected, feared, even envied. After 4 years in which the arrow had only pointed up, everything went suddenly into reverse.

In 2010, two players, ‘Skilled_Sox’ and ‘Skaiwalkurrr’, turned me into a piñata.

In 2007, a PCA package was more than just an opportunity to play a great tournament paired with a winter vacation to a tropical destination. Winning a package was a form of validation. For months you could gloat to friends, family, MySpace, and Facebook that you’d be spending a week in the Bahamas, courtesy of your poker skills. Online poker, that “hobby” you’d been getting judged for, was now a source of curiosity and envy. PokerStars promoted the hell out of PCA, and I’m guessing they lost a boatload of money hosting the tournament each year. But PCA was incredible for driving traffic to their site and helping to build on the idealized “Poker Dream”.

The 2007 PCA was pivotal to my career, but not for anything I accomplished on the felt. I fell midway through day 1 after massively overplaying Ace-Jack on a J76 flop and getting all in against Jack-Seven and a set of 7’s. Like many players in high buy-in tournaments, I’d swapped 5% of my action with a couple of friends I viewed as similar in skill level. One of those friends, another heads-up player named Jon Ford, placed 3rd in the event for $550,000. My 5% cut ($27,500) of his score gave me my largest single day windfall yet.

^{(Left to right…Isaac Haxton, Rob Mizrachi, Jon Ford, Frank Rusnak, Ryan Daut, & Jonathan Little)}

It was money that felt different. It wasn’t earned, it was lucky. It’s easy to rationalize taking shots with lucky money, and that’s exactly what I did.

The shots started small and stayed occasional, mostly $500 and $1,000 games when a soft spot showed up. Then came a moment in late January that I wish I could recreate in detail, but the specifics have been swallowed up by everything that came after. All I remember is somehow finding myself in a $5,000 match and, twenty minutes later, staring at a screen showing I’d won $4,900. Pure chemical euphoria that made everything else in life feel muted by comparison.

After managing to stay away from the 5k’s for another two months, the dam finally burst in late March. Two consecutive $5,000 losses cost me $10k and sent me on a recovery mission, grinding $100 and $200 games until I’d clawed back the losses. But the experience had changed me. I wanted to be battling against the best players in the format, and at nineteen I had both the fearlessness and the runway to keep taking shots.

As my career grew, an unlikely ally emerged: my father. Despite having no interest in playing poker himself, my father was captivated by the drama of the heads-up SNG world. He would watch the empty lobbies with a hawk-like vigilance, and when he spotted an unfamiliar name in the higher stakes lobbies, especially the $2k and $5k buy-ins, my phone would ring. “Jonathan! Get to the computer! There’s some guy I’ve never heard of from Russia in the 5k lobby!”

I would estimate that my father’s phone calls were responsible for more than 20% of my earnings over this time period. As a psychiatrist who had always strongly disliked being on call one week per month, my father now had a son who was perpetually on call. For me, it was exhilarating. Whenever my phone rang over the course of the next decade, I was always hoping the caller ID would read “Dad.”

What followed was the most explosive stretch of my career. April brought $80,000 in profit, nearly matching my entire previous year in a single month. Just months earlier, I’d been so proud of that 2006 total, of the discipline and grind it represented, and of the emotional lows I had fought through to earn that salary. Now I’d reached that sum in just thirty days, not from a tournament score, but from the same format I’d been grinding all along. The sheer scale of what was possible had been completely rewritten.

I was moving fluidly between stakes, playing everything from $200 to $5,000 games, and winning began to feel like a foregone conclusion. May tacked on another $20,000. Then June blew the lid off: $138,000 in profit, a number so large it felt fictional. The climb continued in July, and by early August I was up another $50,000, which totaled a profit of $284,000 without a single windfall larger than $5,400. My confidence was sky high, my ego even higher, and I’d started to believe I had the Midas touch.

The run good was real, but so was the skill. I was a natural at hand reading*, and heads-up poker in that era rewarded exactly that. The heads-up scene was unpredictable. New top dogs could emerge overnight, and it wasn’t always clear whether you were watching a real shift in the hierarchy or just a mirage of variance. None of us could honestly say who was best and who was simply running hot. Looking back, I think I truly was a top three to five heads-up player by mid-2007. But I was playing under-rolled, which meant that timely run good was still the primary driver of my success that year.

The inevitable reckoning began in August, as my first high stakes downswing saw me lose back just over $100,000 of my profit. I ended the year $182,000 in the black from my heads-up sit-n-go play, but also with a new appreciation for just how quick and dramatic the swings could be at the stakes I was playing.

There was a big difference between playing heads-up with a 20-50 buy-in bankroll and playing 6 or 9-handed sit-n-go’s with a bankroll that supported a 300-1000+ buy-in downswing as sit-n-go crushers like Jorj95 and SpaceGravy were doing around that time. I’d spent so much time telling friends and family that poker wasn’t gambling, that I’d managed to bullshit myself. The reality was that I was now playing stakes that were just as much of a gamble as they were a job.

The sensible fix to my over-exposure was simple: sell off some of the risk. And in February of '08, an offer to do exactly that arrived. Enter "Dr. Fells."

Keith in real life, a fellow pro whose Hannibal Lecter avatar had been a familiar face in the heads-up games since before I’d finished high school. One day he asked for my email, explaining that he’d assembled an investment group specifically to back some of the top heads-up players in the highest stakes games. Would I be interested in hearing their proposal?

A month later, Keith and one of his investors, Mike, flew to Connecticut to meet with me. Their presentation was thorough and transparent, with multiple prediction models, various risk scenarios, and conservative and aggressive options depending on my risk tolerance. They were offering a serious backing deal, one that could allow me to continue to play the highest stakes games, while only risking what I was comfortable losing.

With Nick by my side, asking questions and giving input the entire weekend, I found myself increasingly interested in and validated by their proposal. Professional poker was still foreign enough that one of my friends’ mothers had quietly concluded I must be dealing drugs. Having people want to back you was a badge of honor.

Partial backing would smooth the swings and let me keep firing in the biggest games without flinching at a bad month. But it also meant handing someone else a cut of my profit. At 20, with no dependents, I was in a situation where I could afford to take on the variance and grind back up from the low-mid stakes games if things went poorly. I felt myself going back and forth on it all weekend.

On the second night, my father joined us for dinner, and I could tell he was quickly taken with Keith. Towards the end of the night, when it was just Keith, my dad, and myself, my father turned to Keith and asked a simple question: ‘What do you think? Should Jonathan take the deal?’

Keith considered this for a long moment, then shook his head. ‘No. I think Jon will be fine without us. If he downswings, we can always re-visit this in the future.’

That moment has always stuck with me and my father both. Keith and I became fast friends, exchanging more than 300 emails over the next 5 years, and I will always consider him a close and trusted friend.

Having turned 21 in March, June was my first opportunity to head to Vegas and play in the tournament that had inspired my career: the World Series of Poker. I had modest success in the few events I played over the first two weeks, before making a very deep run in the $10k Heads-Up Championship. Heads-Up was my specialty, and performing well on such a public stage was thrilling. Fourth place out of 256 players netted me $108,000.

^{(2008 WSOP 10k Heads-Up Championship)}
That result mattered more than the number suggests. Despite having profited over $250k to that point, I’d walked into the Series with a bankroll of around $100k, so fourth place nearly doubled it. The money had gone where money goes: taxes, maxed out retirement contributions in ‘06 and ‘07, plus rent and the ordinary costs of living. And though I’d never been a car guy, I’d bought a 2004 Infiniti G35 Coupe anyway. Looking back, it was the first thing I bought to be looked at. On some level I knew that, but I tried not to give it much thought. It would be years before I’d let myself be honest about what I was actually trying to purchase.

In November, the World Poker Tour’s annual stop at Foxwoods presented another opportunity. A $10k buy-in, just ninety minutes from my apartment in Connecticut. Live tournament poker in 2008 was a different universe from the online game I’d been playing. Online, I’d been sharp at picking up on timing tells and bet sizing patterns, but live poker offered a buffet of free information. Players routinely discussed their hands between streets, flashed cards to their neighbors, and blathered openly and honestly about their strategies and opinions. All of that was secondary to the physical tells, which were abundant and often egregious.

In 2008 I was an arrogant online heads-up pro who looked to be about fifteen. Despite my recent fourth place in a relatively high-profile tournament, my real name still meant nothing to 99% of the live poker world. I decided to capitalize on my anonymity and immediately went into full thespian mode. I stacked my chips in nonsensical four-chip-high stumps, displayed the manual dexterity of a toddler when placing bets, and told anyone who asked that my grandparents, whose supposed wealth came from owning a bowling alley, had bought me in for my twenty-first birthday. When Mike Dentale asked for my name at my day one table, I decided I was all-in on this bullshit act. “Chris.”

The performance was borderline offensive, a caricature so extreme it should have been unbelievable. In the first hour of the tournament, I limped 3-2 suited under the gun, and then re-raised large after a raise and multiple callers. When my opponent folded to my continuation bet on an A-K-10 flop, I proudly showed my bluff and spent the next ninety seconds meticulously stacking my chips like a child re-arranging building blocks.

For six days, (the FT was the 7th!) I maintained this charade while completely demolishing my opponents. I bagged the chip lead each night, never getting more than 25% of my stack all-in on any single hand from the middle of day one until the final eight players. My control over the tournament felt absolute.

The act nearly crumbled on day four when Jon Friedberg, a seasoned pro, approached me during the unbagging process. “So I heard you’re Iftarii, right?” he asked, referring to my PokerStars handle. My heart stopped, but he didn’t seem certain, so I doubled down. I tried my best to look puzzled, and a bit embarrassed for him. I replied, “I’m… American?” Apologetic and a little flustered, he explained that another pro named Kevin Saul had identified me on a poker forum as a high-stakes online player. I maintained my bewildered expression, we chuckled about the misunderstanding, and he walked away, convinced he’d made a mistake.

It wasn’t until reaching the televised final table** with six players remaining that my true identity (Iftarii) was confirmed. At the final table, despite losing every all-in pre-flop and knocking out zero players, I rode my chip lead all the way to heads-up against Jonathan Little. After hours of battling, I lost three pre-flop all-ins to Little (two for the win) and finished 2nd for $670,000 , keeping 85% for myself, with 10% going to Nick, and 5% to Keith.

It’s hard to say how I felt, because I don’t think I let myself feel it. I was thrilled about the money, but I felt like I’d let down all the friends and family who’d come to watch. Part of me held the competitor's mentality that only losers are satisfied with second.

Most players who run deep in a major tournament feel the pull of the circuit afterward. I did not. Foxwoods had been thrilling, but tournaments were slow, patience-dependent affairs, and patience was neither a virtue I possessed nor one I had any interest in developing. I went home to my heads-up lobbies. That’s where I actually lived, and where I felt I belonged.

At twenty-one, I was exactly the kind of player the game rewarded, but an entirely new game was coming, one that would expose everything I wasn’t.

* Hand reading is a combination of logic and pattern recognition. 20+ years ago, the pattern recognition was the most important element of hand reading. Some of the patterns you might look for were:

1. Preferred betting lines when flopping big hands

2. Bet sizing tells

3. Timing tells

4. Players who were incapable of certain bluffing lines (Example: raising the river with a bluff was something many players were not even capable of in 2008)

5. Signs of tilt, and how a player was likely to alter their approach when tilted

6. Signs that a player was on the verge of tilting

** While we were waiting to be introduced at the FT, Mike Matusow and I made two $5k wagers. The first was whether or not he would be introduced as Mike “The Mouth” Matusow, or simply Mike Matusow; they did not say The Mouth, and I won. The second bet was on when the FT would finish. It ended up being the longest FT in WPT history to that point, and I lost that bet. The heads-up match lasted more than 4 hours, and we finished at 4 a.m.

(Moneymaker’s famous bluff heads-up)

Across seven episodes, ESPN distilled thousands of hands into an addictive highlight reel of thrilling all-ins, audacious bluffs, and entertaining table banter. This game that had previously held no more importance in my life than Monopoly or Battleship had become my overnight obsession. I was not alone.

If you were a high school aged guy who liked sports, the odds were good you now also liked Texas Hold’em. Poker games sprang up across my hometown of Longmeadow, Massachusetts, and within a year the unofficial Longmeadow Poker Tour (LPT) was hosting multiple $5 re-buy tournaments each week. The same thing was happening at kitchen tables all over the country.

We started out playing small stakes cash games, friends and otherwise, but tournaments quickly took over. There was no conclusive finish to a cash game, just a session that ended when people got tired of rebuying or had to go home. Tournaments were different. Somebody won. In the end, one person sat behind all the chips. There was something far more satisfying about being the winner than a winner.

Along the way, there were the thrills that kept us coming back: that rush when looking down at pocket kings, the self-satisfied feeling after showing a bluff, and that stack of greens that told the table you’d been working the blinds all night. In truth, we were all pretty clueless when it came to sharp strategy, but that didn’t stop us from berating each other or rolling our eyes when somebody ‘sucked out’.

Over the next six months the LPT took on a life of its own. Fields grew, buy-ins crept from $5 to $10, and a rotating cast of classmates, acquaintances, and guys you’d never otherwise spend a Friday night with all found themselves around the same table. That was part of the appeal. Unlike a party, nobody got excluded from a poker game — we wanted the biggest fields we could get.

For a few hours, the usual hierarchies took a back seat. It wasn’t as simple as saying it didn’t matter if you were a freshman or a senior, a varsity athlete or the kid who ate lunch alone, but for the duration of a tournament, what mattered most was your chip stack. For someone who was just starting to sense that the social landscape was shifting in ways that weren’t going to favor him, that was a quietly intoxicating discovery.

It was soon apparent that some of the guys were there to see flops and get lucky, while others, myself included, were actually trying to outplay their opponents and overcome the element of luck. A few of us seemed sharkier than others, but none of us had any idea how complex the game truly was.

Around this time I had also begun donking around in the play money games on PokerStars. The real money games were just a click away, but being underage without a credit card, the only deposit option was a money order, which PokerStars required at a minimum of $200. From a net worth of approximately $600, that felt like a lot. Eventually the temptation became too much and I pulled the trigger.

I walked to the bank, marched up to the teller, and trying my best to sound nonchalant, asked them to make out a $200 money order to whatever generic sounding entity PokerStars had created for the handling of these financial transactions. For the next few days I checked my PokerStars account compulsively, waiting for my funds to appear, until finally they did.

Real Money Balance: $200.00.

I was so happy I could have cried, but there was no time for that. I opened two tables of $1/2 Limit Hold’em and sat glued to my screen for the next eight hours. By the time I logged off I was up over $250. I had never made so much money in such a short period of time. For the second time, poker had its hooks in me.

That night I withdrew $200 from PokerStars, protecting myself from ever being in the red. Over the next 18 months I made somewhere around $30,000 playing primarily Limit Hold’em, with tournaments, Sit ‘n’ Go’s, and Heads-Up SNGs mixed in. My game selection was all over the place and I had no consistent strategy or guidance, but I managed to cash out a steady stream of profits.

As my poker career blossomed, my academic career took a nosedive. In the span of just two months, in the middle of my junior year, I had dropped from honors math to standard math to remedial math. I had never been keen on doing my homework, and now I was doing almost none of it. As my GPA plummeted, my college prospects began to shrivel up. One Saturday afternoon, at my mother’s insistence, my father forced me off the computer and into the car for a road trip to local colleges.

When we arrived at the campus of Westfield State College, the nearest school to our home, we were greeted in the parking lot by a staff member who was just about to begin a tour of the campus for prospective students. She asked us if we’d like to join, and I turned to my father with a grave expression. “If we don’t have to go on the tour,” I said, “and can leave and go to lunch, I will go to this school.” Surprisingly, that was good enough for him, and minutes later we were at Burger King, Whoppers in hand.

I had no business being at Westfield State, and I knew it from day one. On the first day, there was an attendance-mandatory dorm-wide meeting to go over rules and codes of conduct. When the resident advisors came around to make sure nobody had stayed behind in their rooms, I was hiding in a closet. I wasn’t going to blind out of the $530 WCOOP 6-max event for some dumb shit meeting.

But college wasn’t a total loss. The roommate matching system, against all odds, had placed me with a guy named Chad Walker, who was quite likely the only other serious and winning poker player at the school. I don’t think either of us had even mentioned poker on the questionnaire that was used to match roommates. During our first week at Westfield State, Chad and I had been invited to a dorm room cash game. Nick Petrangelo, who was not a student at Westfield, was there that night on the invitation of his friend who was hosting the game. I don’t remember all that much from the game except that Nick lost, Chad was the big winner, and I more or less broke even. I remember not being especially fond of Nick and I had guessed the feeling was probably mutual. I had no idea that night that both of these guys would end up being two of the most important people in my life and career.

(Chad and Nick in 2007)

Despite having found a genuine friend in Chad, I largely regarded college as a pain in the ass. Every night I pleaded my case to my father over the phone, and every night my begging fell on deaf ears. After one semester he finally relented, and I was released from academic drudgery and free to pursue my career as a professional poker player.

In early 2006, I was 18 years old and living on my own with all of the freedom I’d always craved. I had despised structure my entire life: the alarm clocks, the homework, the bedtimes, being told when to sleep and when to show up and what to learn. For the first time, my time was entirely my own.

When I left school, the staple of my income had been playing 4 tables of $5/10 6-max Limit Hold’em on PokerStars. I’d done some rough calculations and estimated that if I worked a 40-hour week, I should earn somewhere in the neighborhood of $60,000 that first year. Within weeks of dropping out, I began dabbling in Heads-Up Sit and Go’s and quickly realized I had a knack for them, as well as a far greater passion for the format than I did for Limit Hold’em.

Over the course of that year, I transitioned from mostly Limit Hold’em to playing the $100 and $200 Heads-Up SNGs full time. Unaware of the existence of HUDs or tracking sites like Sharkscope, I kept track of my results on sticky pad notes. I had a rudimentary appreciation for variance and figured that by tracking and analyzing my statistics, I could better understand the nature of my fluctuations in luck, as well as the progress I was hoping to see.

I kept a two-column results tracker. A match lost would earn a tally in the L column, a win in the W. At the end of 100 matches I would subtract the losses from the wins, multiply the difference by the buy-in, and then subtract 100x the rake.

I remember my confidence rising and falling dramatically with the results of each completed sheet.

I knew very little about this world I had chosen to build a career in, and I showed almost no interest in reading the various forums, books, or strategy material that were available at the time. I almost never discussed strategy with other players. I was a feel player to the max, and I wouldn’t have been coherent if I’d tried to explain my thought processes at the time. In the poker world, I was a lone wolf.

My days followed a rhythm that felt genuinely exhilarating. My work day came to a close around 3am, at which point I would jump into the shower for what was a sort of decompression ritual. As the water fell over me, I would think back on my day and consider how things went, what I did well and what I could have done differently. I would dwell on what my trajectory looked like given that day’s results. In that first year a very good day of poker might see me profiting two or three thousand dollars, and I vividly remember the joy and optimism that I felt on those nights. At the time, it manifested as the recurring jubilant thought: “How is this actually my real life?”

On the nights when I’d lost two or three thousand dollars, I would still end up in the shower, but my decompression ritual went very differently. As the water pummeled me, I was an emotional mess, angry at myself, frustrated by the repeated “injustices.” I oscillated between a shallow sense of entitlement and a deep feeling of shame. On those nights, that meant never letting my emotions show that I had been beaten. Absurdly, this self-imposed rule extended even to the moments when I was alone. If I were to express my anger or sadness either verbally or physically I would feel ashamed at my lack of restraint and ‘emotional control’, a concept which I had greatly misunderstood.

Strangely enough, this immature outlook led me to stumble into a practice that would work wonders for me for years. While I wasn’t allowing myself a healthy release over the anger and sadness that I felt towards my bad fortunes on the felt, I think on some level I was aware of a need for catharsis, for some emptying of my emotions before going to bed. At some point early on, I decided that to feel bad for myself meant I had lost perspective and was being an ungrateful little bitch. How fortunate I was to be forging a career in this game that I absolutely loved.

To really feel it, I would build the alternate life narrative in my head. One in which I was in college, on a very traditional path. I would picture myself studying for an exam in a class that bored the living shit out of me. Then I might imagine myself waking up tired in my 180 square foot three-person dorm room and having to bundle up to walk across campus to an intro to philosophy class which I had absolutely dreaded. I conjured up this life in which I was meticulously tracking my spending on food, and gas, and weighing whether or not each experience or purchase was worth the ding it would inflict on the three-digit balance in my checking account.

After 5-10 minutes of building this vivid alternate reality, I’d let myself awaken to the reality where I was taking this shower, in my own apartment, in which the worst thing that had happened to me was that I’d lost some of the money that I’d never dreamed I would have at this stage in my life. It worked like a charm. Out of some mixture of gratitude and ego swelling, I was propelled out of my misery and exited the shower truly buoyant.

This gratitude practice worked for many months, until it didn’t. The story began to feel redundant as I’d started taking my freedom for granted. A sense of entitlement towards my career had begun to take root, and the eventual nail in the coffin was my recognition of how self-indulgent the whole exercise was, little more than a celebration of how awesome I thought I was.

At that point, the story I told myself escalated. I began to picture the people closest to me dying in very sad ways. I’ll spare you the morbid details, but I played the scenarios out through the funeral and the ensuing weeks and months in which my life was forever changed. It always ended in a mess of tears, and I loved that. I had been out of touch with this part of myself for so long, and it felt great to cry my eyes out. These nights of loss kicked off a period of emotional growth that I desperately needed. Imagining the loss of my loved ones gave me and my backwards ass approach to emotions “permission” to cry. I thought I was crying for my loved ones, which was perfectly permissible and perhaps even admirable by my unwritten rules. It was only many years later that I would come to understand that I was actually crying for myself, working through the fear that I wouldn’t make it as a pro, the shame that I had made bad decisions and been out-smarted by my opponents, and the frustration that this game wasn’t fair, and that tonight justice was not dispensed because I had lost.

As the year went on, I fell into a comfortable rhythm, playing just shy of 2,500 Heads-Up Sit and Go matches and profiting nearly $60,000. On the side I was also playing occasional tournaments on PokerStars, as well as a private cash game in person. Between the three, I would finish my first year playing professionally with just over $82,000 in profit. I felt firmly entrenched as a professional player, and life was good.

If 2006 had been the year of steady profit, a year in which I’d found my bearings, then 2007 would be the year of extremes — a year that would school me on both the intoxicating heights and the crushing lows that define a poker player’s existence.

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_{A note of thanks to David K Lappin, whose generosity with his time, his insights, and editing instincts helped shape this writing.
I am extremely grateful.}