How a 16 Year Old Turned $20 into $20,000 in Poker (Part I)

Author’s note: ¹

The Story of Pete the Poker Player

It’s 1989 and I’m born. I am told I was a well-behaved baby. Then like 14 years pass by and I’m kind of this big disappointment. Not above average at anything. I’m in non-honors classes (other than math) and I get mediocre grades. I don’t participate in any extra-curriculars like sports, music, or art. I play a lot of video games but I’m not good at any of them. I don’t have any close friends. I’m too online. My parents and teachers reiterate to me that I am actually very smart, which I did believe, but it doesn’t motivate me much nor prevent me from dozing off in class all the time. My father yelled at me a lot. There were some anger issues. I didn’t get into trouble most of the time but I didn’t keep a clean record either–a few suspensions for fighting did occur. Young Pete did not check any boxes for the model Asian-American boy–disciplined, polite, good at school, good at tennis or golf, good at piano. Not sure we have a good trajectory going here.

Then I discovered poker and everything changed.

One summer night while staying up late way too late, I stumbled upon the 2003 WSOP Main Event playing on ESPN2. I didn’t know it at the time but this would be the most historically significant WSOP ever played–the first one with hole card cameras to broadcast live hands, the first one with online qualifiers, the first actually won by a qualifier, an underdog amateur aptly named Chris Moneymaker². This WSOP is the ground zero of the early 2000’s poker boom. I watched every episode and every hand. There’s just something incredibly compelling about intense competition with serious money at stake. Poker then became my life’s obsession as I studied it non-stop–it was the first time in my life where I sustained any kind of high self-motivation. I’d start playing in all these local home games ran by older students and I opened accounts across multiple online sites.

My first real online poker account started with $20 in 2005 on Pokerstars. I told my mom I needed to buy some Pokemon cards on Ebay so she transferred some money into Paypal³. What I actually did was pay some random guy $25 through Ebay for him to transfer me $20 to my aznboi997⁴ account on Pokerstars. That’s all you needed back then to get started. I did not need to verify my identity nor that I was even old enough to gamble. It was a different time back then.

I went bust the first time. I played micro-stakes limit poker and no-limit sit-n-go’s (SNG, also known as single table tournaments) and just bled out to zero. Devastating. I’m lying in bed at night wondering if I’m destined to be average for the rest of my life.

It can’t end like that.

I re-loaded. Traded another $25 on Ebay for $20 on Stars.

I had to make this work. I scoured the internet on the secret to winning at poker. There was a big “a-ha moment” that changed my game–Ed Miller’s post on Twoplustwo forums that was titled something like “Why aren’t you crushing these games?” More on that later.

I read books. I analyzed countless hand histories. I kept detailed stats on my opponents’ tendencies. I created a foundation of evaluating my play–basically crunching numbers and determining whether my line was +EV (expected value) based on certain heuristics. That was the old school way of improving. An entirely new philosophy and ecosystem of poker training developed in the next 20 years. More on that later.

I rapidly improved my limit poker game to turn the second $20 into about $100 over a couple months. Then on magnificant summer day, around the 2 year mark since the 2003 WSOP enamored me with the game, I caught my first major break.

I won a $3 buy-in multi-table tournament (MTT) with a 1st place prize of just over $1,000. The only thing I remember from that 6? hour marathon tournament was that my winning hand was 97 off-suit.

That first $1000 win? Holy fucking shit, does it have me on cloud-nine. I want to scream my lungs out in triumph but I can’t because my family is sleeping. I take a walk to some nearby vending machines to buy a coke and I feel like I was flying. I’m skip-hopping and fist-pumping all over the quiet suburbs at well past 1AM. I take that first sip and it’s the greatest sip of my life. Ahh. I love playing good. I love winning.

you never forget the final hand of your first major tourny win

Just like that, I had 10x’d my bankroll and no longer had to keep grinding at the lowest micro tables. I moved up to $.50/1 and $1/2 stakes. The next year or so, all I’m doing after school is clocking in cash game sessions, while convincing my parents that it’s harmless fake-money and that it won’t affect school performance–if anything, it will help me with my math skills? I’m mostly a limit specialist and once I’m past the $2,500 mark, I start playing $2/4, $3/6, and $5/10 though I occasionally mix in some SNGs and MTTs too⁵. I encourage my cousin Arthur, who has become my main poker buddy, to play SNGs on my account and he adds another $2-3k in profit. I don’t try to be a hero and take shots ⁶. We’re responsibly grinding and we’re thriving.

By the end of 2006, the account sits around $20,000. Pete is no longer average (or worse) at literally everything, he’s now demonstrably good at this one thing. More importantly, he can see that hard work and dedication to learn with an open mind will lead to powerful and positive consequences. That’s the story of Pete the poker player—whichs peaks right there before anticlimactically losing steam as he nears legal adulthood.

During senior year of HS, my playing volume tapered off. I made more friends and started to enjoy the social life that I never had. I spent more time on academics so I could get into a decent university. Lastly, my view of the game changed kinda changed for the worse. I would seldom play in college and withdrew everything in 2008. I got lucky to get out when I did because three years later, Black Friday happened and it completely halted the online poker economy. People couldn’t get their money out.

Poker becomes too much of a grind. It’s not what I thought it would be when I first started playing–more on that later. It gets harder to struggle through the extended periods of negative variance. My precious money becomes the only proof that I’m good at anything. I feel like I’m protecting it by not playing. I don’t dare withdraw the money to spend it. It’s meant to be grown in perpetuity, poker or otherwise.

Looking back on it, poker became the skeleton key that unlocked the rest of my life’s trajectory.

This $20,000 would later fund my first Interactive Brokers trading account and my second trading account at Speedtrader. Those two accounts would grow into combined mid six-figures while trading the great OTC rush of 2013-2014⁷. I hit 7-figures by 2016, achieving financial independence while still in my 20’s. Now in 2026 with a family, we are at 8-figures across index funds, pre-IPO SPV’s, college 529 plans, home equity, IRAs and more. That $20,000 poker bankroll, made before the age of 18, grew into everything that I have right now. There’s also the intangible value of spending multiple decades constantly thinking about probabilities, behavorial patterns and risk management. It’s the power of compounding–not just money but knowledge and skill.

Home Games and An Early Dream

Prior to 2003, the only time I ever played poker was either Chinese poker (pai gow) with my grandma and great aunties during Tet or playing simple five card draw with other kids for snacks and candy. Post-2003 WSOP, the game of Texas Hold’Em became an unexpected cultural phenomenon–every teenage boy either owned a chip set or knew a guy who owned a chip set. All the cool kids would hold their own home poker games⁸. I’d hear about home games from 3 cities over where my sister would have to drive me an hour.

Tony Pham. He was a couple years ahead of me in my sister’s HS class. Tony ran the biggest local home games in the Orange, CA area–usually no limit tournament style–that I cut my teeth on, prior to online play. The games usually compromised a mix of preppy overachiever type-A students from our high school and Tony’s less-refined Viet friends from Garden Grove⁹. I was always the youngest one there, as a freshman playing with juniors and seniors. I didn’t know what I was doing but I embraced the fundamental idea of playing the man and the context, rather than just speculating the board with your own cards. I enjoyed the creative freedom within the game–the many paths one could take to winning the pot. I would hyper-focus on every hand to remember each player’s tendency–so I could later exploit it.

That right there, was the core appeal of poker for 14-year old Pete. I yearned to feel superior to others. I’m shit at computer games. Sadly not athletic enough for sports even though I love watching them. Not enough of a nerd to be top of the class. This will be my defining talent now–this little card game that’s about psychology and money. I develop this naive, romantic dream about what poker could be for me—a new image of myself I could daydream about instead of paying attention in lit class. I’m totally in the zone, not giving anyone an inch. I’m playing in an underground nosebleed games with all these stone cold world-class professionals, and I’m just ripping moves without any fucking fear. They are in awe of me.

And it all started with making moves against Tony and all his friends. I loved trapping. I loved bluffing. I would float¹⁰ long before floating became a mainstream poker term. Usually Tony’s less-refined Viet friends were a little tougher to play against. I remember a guy named Dennis Nguyen who thought he was the next Scotty Nguyen, putting on some table talk and deducing my bluff. Then he called me with some weak-ass shit that he absolutely should’ve folded and I had to sit there and seethe. Did that ever stop me from going at him again? Nah. Meanwhile, these preppy A-students who aced AP Calculus were often the worst players of all. Ironically, they would never use math and would try to rely on intuition. I usually had them dancing on a string, unable to keep up with me. Too much time studying for the SAT over studying Theory of Poker. You go make your $90,000/yr at Washington Mutual, I’m gonna win millions in the WSOP Main Event one day.

I won my fair share. Older kids told me that they hated being in a hand with me, which I took as a badge of honor. I had a lot of fun. Whenever you approach a new game, this is always the most enjoyable phase. It’s that honeymoon phase where you’re just endlessly absorbing as a newbie and you have an inkling of an idea of how to be good at it, but not too much knowledge that you’re discouraged by how much you don’t know. You don’t worry about optimization, min-maxing, or trendy strategic metas–you just let yourself play. It awoke something deep inside of me that I never knew was there as a do-nothing chronic underachiever. It’s a man’s basic desire to make something of himself.

A Slice of Poker Education in 2004

Speaking of Sklansky’s Theory of Poker… let’s talk about poker education and self-improvement. For years, my dad would take me to Barnes and Nobles once a week to read whatever I want for hours on end. Could be fantasy sports magazines, could be Calvin & Hobbes anthologies, could be John Grisham law thrillers. At one point in my life, I kept buying these video game strategy guides that would let me “hack” my way to finishing the game. It was to compensate for the fact that I wasn’t great at playing them on my own. This created an early insight that the best way to hack into something you want to improve at was to read the most popular books on it and lo-and-behold, this Barnes and Nobles had a gambling section!

You had Phil Hellmuth’s book. You had the Tom McEvoy and TJ Cloutier tournament books. You had the supposed grand daddy of ’em all: Doyle Brunson’s Super System. Then there were these esoteric “2+2” textbooks that often had a handgun (???) on the cover, usually written by a guy named David Sklansky, who had far less name recognition as a poker professional than the other authors.¹¹

I combed through all of them. There was a time where I thought Phil Hellmuth was the poker GOAT so I based all my decisions off his book’s strategy. But then other books would contradict his advice. So what to do then?

This led me to a secondary insight–it’s not enough to just read the books, you have to know the good books from the bad, which requires a bit more work into vetting them via review & feedback from real actual players. To find clarity, I plow through all the poker forums–not just Twoplustwo forums (because, y’know, they could be biased for their namesake), but also PocketFives, FTR, and rec.gambling.poker and even talking to a few ambitious players I met in real life. It was near-unanimous among serious players that 90% of the books out there were utter crap–especially the Phil Hellmuth book! Super System, once considered a breakthrough, was now badly oudated even in 2005. 2+2 books were considered rock solid due to their robust mathematical foundation. Sklansky was a prominent math guy before becoming a pro gambler, so it checked out. That’s when I decided to make those books my core curriculum and discard everything else.

Back then, poker teachings were a lot of loosely tied together heuristics about how to play common situations. Pre-flop was pretty simple but post-flop examples would gets fragmented into a few situations for a game with nearly unlimited sub-variations of such a situation. A 1990’s poker book, even a good one from 2+2, would have chapters like this:

When to induce a bluff
When to take a free card
Playing weak hands
How to play pairs
Check-raising

Modern poker players might ask me…

But why not watch training videos and turn decision-making into pattern recognition? Bro, Youtube ain’t even a thing yet.

But what about hand ranges and staying balanced, and following a top-down strategy? We’re like four years away from that right now.

But what about game theory optimal play and using solvers? We’re like twelve years away from that right now.

At first, I struggled a bit. The problem with applying classics like Hold Em’ For Advanced Players (published 1999) to the 2005 micro stakes games was that they assumed this slower 1990’s live casino playing conditions. The mathematical concepts remained sound but actual execution of strategy had to be adapted to the current online landscape ¹², which I was unable to do due to lack of experience. Despite reading the supposed best books out there, I failed on my first try. Because of my immaturity and youthful ignorance, I made a lot of silly excuses.

This has to be rigged. These sites will generate an action card on the river for bigger pots and bigger rakes.

Players are too dumb here, pre-flop strength never holds up into showdown. I need to move up stakes where they respect my raises.

At this point, I scoured the 2+2 forums to try to get feedback from current players. Maybe they’d agree with me that .05/.10 was unbeatable and I need to move up to $5/10 to play real players. In the small stakes sub-forums, what I saw were all these garbage theads from newb posters who echoed the same sentiments above. It was like reading my own internal thoughts.

The usual response from mods and forum vets? Troll these newbs and keep citing the same “holy grail” post to read. Read Ed Miller’s post and get gud, ya donkey.¹³

2+2’s newest and brightest poker author Ed Miller had this widely read and stickied post titled: “Why aren’t you guys crushing these Microlimit games?”

Ed basically went to town on all of us. If I had to re-write the post from memory, it was like this:

You’re not losing because you’re dumb. You’re not losing because you don’t study. If either were true, you wouldn’t be here. You’re losing because you’re a little bitch who’s scared. You’re nits who are too afraid of losing. So resigned are you to bad run-outs from these ultra loose 7-player showdowns, that you stopped trying to execute proper post-flop strategy. You have to keep pressing every single small edge. You have raise that nut flush draw when you have at least 35% equity against 8 other players, don’t be a little bitch and wait for the draw to hit to do it. All these fish players that you lament not being able to “outplay” with fancy check-raise bluffs? They are the value! They butter your bread! All these terrible books that tell you to play fit or fold poker? Well, that’s losing poker. It’s losing poker because the advice ignores the single most important variable: the size of the pot.

I’m probably not doing it justice. It really hit home. It hurt my ego and I knew that there was absolute truth to the post. There was no longer any acceptable response from me other than to put aside excuses and “get gud”.

So I challenged some previous assumptions I had. I bought Ed’s book “Small Stakes Hold ‘Em” which was more intentionally targeted for 2005’s looser online playing conditions. I poured through so many hand history threads where people would discuss how to play the hero’s line without knowing the final result¹⁴. Then I had to rip through my own hand histories with that same framework. What should I be doing *here in this specific situation* 100 times, with imperfect information? I’m playing a much different game now. I’m not making moves against Tony’s pals anymore. I’m pressing equity advantages in massive multi-way pots against faceless online avatars and the game is far from sexy.

What effectively happened was that my post-flop game completely changed. I went from being aggressive only when I thought I was a lock to win to being aggressive when I had any dominant share of equity in any given street. I ingrained in my mind the concept of reverse implied odds while holding medium or low strength hands, so I knew the situations to cut bait and save money.¹⁵

Then you had Pokertracker (PT), a must-have software for any serious online player. You had to keep your stats and your notes on players.

There was a PT triple slash line to measure every single player’s playing tedency at very generalized level. It was VPIP/PFR/AF.

VPIP = Voluntarily Put Money In Pot, the % of hands you pay to play pre-flop (which excludes free checks on blinds)

PFR = Pre-Flop Raise, which is the % of hands you’re raising pre-flop

AF = Aggression Factor, which was calculated as (bets+raises)/calls post-flop

So you have all that data and it allows you to put players in a box. Below is the classic looseness/aggression quadrant. You have to understand that almost all players become an archetype based on their tendencies–especially so at lower levels where amateurs lack the self-awareness and skill to change up their patterns. Once you have boxed a player down, you follow simple heuristics on how to adjust to their play.

55/40/3? That’s a maniac who’s trying to run you over. Gotta stand tall to his pressure, defend your hands into showdown.

90/10/1? That’s a guy who wants to play every hand. He’s terrible and easy to play against. Value-town him to death. Early/mid 2000’s limit poker was full of these types, which is what made the game so lucrative at the time.

22/15/2? That’s someone trying to play correctly (tight-aggressive). Might be good, might not be, but he’s far from your biggest edge at the table.

10/2/0.25? That’s an old man drinking his cup of coffee, scared to play anything but premium hands. If he’s aggressive, look out. You don’t really make money off them¹⁶, you just avoid losing to them because it’s obvious what they have.

I fixed some of the post-flop leaks where I came up short on extracting value. I understood which players to be involved with and attack, which required learning about the value of position. All of a sudden, the game had more easy buttons to press than when I started. $20 grew into $100. Then after the $1000 MTT windfall, that turned into $2,000 then $5,000 then $10,000. Pretty steady, don’t remember a whole lot of bumps in the road although it didn’t feel that way at the time.

Back then, this was what you needed to make a six-figure career with decent sharpe, off of online poker.

Pre-flop discipline (understand how position changes hand strength and then memorize charts)¹⁷
Post-flop fundamentals (understand some loose mathematical concepts, develop some feel for this with experience)
Pokertracker with HUD to datamine player tendencies as well as tracking your own habits
Study your hand histories under a proper mathematical framework to create a positive feedback loop
Sound bankroll management
Multiple monitors¹⁸
Table selection, although less important if you’re making up for it with volume

That last one, table selection, is a criminally underrated aspect of poker and it eventually became a big factor to how I boosted my profits. Because I only had one small monitor and I’m a slow processor¹⁹, I didn’t create a ton of extra volume from multi-tabling. It was common at the time for pros to be playing 12+ tables across multiple screens. So to create bigger margins while only playing 3 tables at most, I would hone in on table selection. The essence of that would be to seek out the absolute worst players and ensure maximum table time with them. More on that for the next essay, which I am tentatively titling:

Table Selection — Forget Being a Poker Virtuoso, Become a Bum Hunting Merchant Instead

How a 16 Year Old Turned $20 into $20,000 in Poker (Part I)

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