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My name is Wesley Ismay. I have been a pro poker player for 21 years including winning over a million dollars. Enjoy. Or Don't. I'm not your boss.

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Chapter 4: Population: One—The Fedora Messiahs, The Art of the Neg, and The Electric Fence

Posted on February 8, 2026February 8, 2026 by wes

I eventually moved out of South Dakota—out of the trailer house I had declared my sovereign nation. Population: one. GDP: poker winnings. Culture: insomnia, message boards, and a profound, theoretical obsession with “The Game.”

It was my monastery. A digitally lit cave where I played poker, lurked on TalkingPoker, and slowly fermented into a person with loud opinions and no witnesses.

But poker wasn’t my only text. Like every other socially maladapted male with an internet connection in the mid-2000s, I found the gospel of Neil Strauss. I didn’t just read The Game; I studied it like Pot-Limit Omaha. I memorized the scriptures of “Mystery,” a magician in a fuzzy hat who taught that the key to female affection was “negging”—the art of the calculated backhanded compliment.

The logic was intoxicatingly stupid: lower a woman’s value just enough that she scrambles to prove herself to you. Tell her she has lipstick on her teeth or that her nails look cheap. I detested small talk, despised performative rituals, and would have found a vapid model boring within ten minutes. Yet there I was—a basic incel with a six-figure bankroll and zero social skills—memorizing scripts to entrap women I wouldn’t even like, just to prove the theory worked.

I needed social skills the way a starving man needs food, but I had no idea where to begin acquiring them. I had skipped every tutorial level everyone else seemed to get for free. So I experimented the only way I knew how: like a scientist dropping variables into a chaotic system to see what reacted.

I started going to bars alone. Not to drink heavily or to hit on anyone—I barely knew how—but out of sheer, directionless curiosity. I would walk in, scan the room, and just… sit down at a random table occupied by strangers. No opener, no plan. Just plop into an empty chair and wait to observe what happened.

Most of the time it was innocuous. A brief awkward silence, then someone would ask, “Do we know you?” I’d mumble something noncommittal and listen. People were surprisingly tolerant. They’d include me in small talk about sports or the jukebox. Nothing to be afraid of. Interesting, even—like watching a foreign culture up close. But nothing to connect with either. No spark, no recognition, no sense that I belonged in the same species. I’d leave after one beer, data collected, no closer to understanding how normal humans turned proximity into conversation into friendship or more.

One night in Las Vegas, I decided to actually try the scripts. I sat next to a woman at the bar—Asian, composed, minding her drink—and deployed a line I had rehearsed alone in my head like it was a clever theorem.

“Your hair’s too straight,” I said. “Why don’t you curl it, like any reasonable person would?”

She stared at me. Not offended. Not amused. Just… blank. As if I had spoken in a dialect meant for no one.

We sat there for ten minutes without saying another word, sipping our drinks in total silence. Then a man—mid-forties, white, confident in the way only the uncurious are—walked up, handed her a $100 voucher, told her she was beautiful, and walked away.

It dawned on me then. The voucher. The silence. She wasn’t a civilian; she was a professional. And the older man knew the one rule I didn’t: you don’t trick the dealer; you just pay the ante.

The universe had negged me so cleanly it felt surgical. I wasn’t the manipulator in that moment. I was the lesson.

Those evenings confirmed what I already suspected: the rules were written in a language I had never been taught.

The PUA scripts at least offered a phrasebook. But there was still the logistical problem: you had to leave the house. My arena was a dark room lit by dual monitors. I could study the theory of negging supermodels, but I had filtered real women out of existence. The strategy fell apart entirely when the only audience was a plastic Randy “Macho Man” Savage doll.

“She’s insecure, brother! Snap into a Slim Jim!”

So I turned to online dating, assuming my stats would carry me: wealthy, smart, “science-adjacent” attractive. But the digital marketplace had a filter Neil Strauss hadn’t prepared me for: the 6’0” rule.

I wasn’t six feet tall. Which meant I was erased. My carefully crafted openers vanished into the void. The few responses I got were from people who seemed less interested in living a life than in decorating one.

I resigned myself to the void.

Until yosoyveneno.

I didn’t find her on a dating site. I found her where I found everything else of value: the poker blogs. She played in Wil Wheaton’s weekly $22 tournament under the handle yosoyveneno—Spanish for “I am poison.” A rational man would have seen the warning label. I saw reprieve. Poison tasted better than nothingness.

She was thirty-seven. I was nineteen. When she invited me to California, I accepted immediately. I told myself “experience counts as experience.” That is the lie men tell themselves right before making a mistake that will haunt them for a decade.

I landed. She picked me up. I had not previously seen a photo of her.

The mismatch was total: she was nearly twice my body mass—I was a twig who had stress-starved himself into a new tax bracket; age, life stage, everything. The tequila was excellent. The sex was… educational. I did not climax the first time, which I blame entirely on the Jose Cuervo and only partially on the collision of fantasy with unairbrushed reality. But I acquired a story. And in the economy of the lonely, a story is the only currency that spends.

The trip included Disneyland, because of course it did. While waiting for Space Mountain, her ten-year-old daughter looked up at me and asked if I had kissed her mother.

“Yes,” I said, trying to sound sophisticated. “And more.”

To this day, that remains the most cursed sentence I have ever produced.

I used to be ashamed of that story. Now I see it for what it was: the perfect initiation for someone like me. I didn’t get romance; I got reality—the awkwardness, the desperation, the absurdity of bodies colliding without souls attached.

Will Rogers never misses: “There are three kinds of men. The one that learns by reading. The few who learn by observation. The rest of them have to pee on the electric fence for themselves.”

I didn’t just pee on the fence. I grabbed it with both hands, shook it, and waited for the shock to make me feel something.

And it did. It taught me that the isolation of my poker cave wasn’t a prison. It was a quarantine. But every time I broke it, I came back infected.

As I sat back down in the blue light of the monitors, the Macho Man doll watching from the desk, a new, cold nausea set in. I couldn’t tell anymore if I was disgusted by the chaotic world I had just visited, or by the desperation that had driven me to it. The chips were stacking up, the logic was sound, but for the first time, the sovereign nation didn’t feel safe.

It felt empty.

I started to question why a life built on winning felt so completely, terrifyingly hollow.

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