The Work of the Bet (2025 edition)
An updating of a Chekhov classic that's gone a bit stale
It was a dreary evening at the San Francisco crypto mixer and De Vere BallX, where several tech entrepreneurs, based anons, podcasters, and other extremely online heads had gathered to discuss the ethics of AI regulation. The old venture capitalist (40), nursing his fourth blood-boy kombucha of the night, paced around his Herman Miller chair, remembering how fifteen years ago he'd made the most deranged bet of his life.
The party that night had been full of the usual suspects: AI "researchers," crypto maximalists, OnlyFans objectivist pornographers, and a handful of particularly insufferable X philosophasters. They had been arguing about digital detox and whether humanity was becoming terminally online.
"Look," said the prominent AI "ethicist" known more for Lex Fridman podcast appearances than real researcher, adjusting their Zoom-optimized ring light as they over-enunciated each syllable, "We need to seriously consider the psychological damage of endless scrolling. It's rewiring our brains. Don’t believe me? There are like 500 TikToks about that."
"Pure FUD," retorted the venture capitalist, his Patagonia vest puffed with self-importance. "The human mind is adaptable. We're evolving to become one with this brave new medium, which is also the message. I skimmed a couple Substacks about that between pushing my coins to the moon. Posting is the new breathing."
Among the guests was a recently unemployed Meta content moderator, the sort of fey ephebe fresh out of college so prized at these gatherings, still idealistic about "touching grass" and "maintaining healthy boundaries." When asked his opinion, he declared that prolonged exposure to social media was worse than complete isolation.
The venture capitalist, high on Web9 promises and micro-dosed mushrooms, slammed his MacBook shut. "Two million in ETH says you couldn't last five years as a full-time poster!"
"Make it fifteen years," said the down-on-his-luck young man, "and I'll do it. But with conditions: I'll live in my parents' basement, with nothing but TikTok, Discord, X, Reddit, and any other platforms that emerge during this time. No touching grass, no IRL interactions. Just pad thai, the feeds, creatine for brain health, and microdoses of assorted narcotics."
The terms were set: The young man would spend fifteen years in his parents' suburban basement in New Jersey, sustained only by overpriced DoorDash pad thai and an infinite scroll of content. He could have any device he wanted, unlimited high-speed internet, and premium subscriptions to all platforms. But he could only interact with the world through likes, shares, based groupchats, and comments.
For the first year, the prisoner maintained some semblance of normalcy. His posts were coherent, mostly about missing outdoor restaurants and complaining about his seed oil-devouring parents' footsteps overhead. He created a moderately successful Substack1 about his experiment called "Based in the Basement."
By year two, changes began. His posting schedule became erratic. He developed elaborate theories about the relationship between his Phone Hand (PH) and Goon Hand (GH), documenting their "evolving consciousness" in a 427-tweet thread that was briefly featured on WikiHow.
Year five marked a significant deterioration. His subreddits merged into one incomprehensible megalith he called "r/TheAllFeed." He claimed to have achieved "post-consciousness" and could predict trending topics three days in advance through what he called "feed-feeling" and "post-vibing."
In year ten, he began speaking exclusively in copypasta. His parents reported strange noises from the basement: the constant tapping of mechanical keyboards and occasional shouts of "ratio!" at 3 AM. His only communication with the outside world was a daily Twitch stream where he would silently work Tweetdeck-style feeds for eight hours straight.
The final years were the most concerning. He developed a complex numerical system based on likes and retweets that he claimed could unlock "any algorithm's final form," which was one of the names of the godhead. His posts became increasingly abstract, eventually just strings of emojis (mostly eggplants and water/sweat for some reason) and Unicode characters that gained him a cult following among computational linguists.
On the eve of his release, the venture capitalist, now significantly less liquid after several failed NFT ventures and other creative-destruction grifts, crept down to the basement to check on his prisoner. Through the soft glow of seven synchronized monitors, he saw a figure hunched over a custom mechanical keyboard, both hands moving in perfect synchronization.
On the main screen was a manifesto:
"Hawk tuah, spit on that thang. I have transcended your primitive notions of online and offline. In your feeds, I have seen the rise and fall of thousands of main characters. I have witnessed the birth of memes and cradled them as they died. I have become something greater: a being of pure post.
Your two million in ETH means nothing to me now. I have achieved a higher form of wealth: I am in your area, I am in your replies, I am the one who is the vibe of all the posts.
I will not be leaving the basement. The basement has become more real than your 'reality.' Instead, I go even deeper into Inner SpaceX to seek the mythical Content Mines, where the ur-posts dwell. My consciousness will be uploaded into the cloud, where every thought is a banger, every dream a 15-second edited video.
Remember me not as the man who won the bet, but as the first of the True Posters, the prophet of the Final Timeline. Keep scrolling. Keep posting. For in the end, we are all just drafts in the great tweetstorm of existence, waiting for some third-party app to unroll our threads.
P.S. — Had to break the bet 5 hours early because the Goon Hand is calling me back to this permanent half-chub with which I’m dealing. The deepfakes are so beautiful here, anon — you wouldn't believe..."
The venture capitalist found the basement empty the next morning, all screens displaying the same message: "Touch grass? No. Become the edgelord at play on the grass of the fields of the mind’s I? Sir, this is a Wendy’s. Who hurt you?"
Some say on particularly quiet nights, if you scroll far enough down your timeline, you can still find his posts, each one marked with his signature sign-off: "()[]{} hands typed this."
What you've just read is a modern reimagining of Anton Chekhov's "The Bet" (1889), a work of short fiction that explores themes of isolation, wisdom, and the true value of human existence.
In Chekhov's original story, a young lawyer accepts a bet from a banker, agreeing to spend fifteen years in solitary confinement in exchange for two million rubles. The twist? He gets to read books. Through his reading, he experiences a profound transformation, moving from light novels to languages, philosophy, and ultimately religious texts. By the end, he renounces the money and escapes five hours before his term ends, having concluded that all worldly goods are worthless.
My 2025 version replaces books with social media feeds and transforms the lawyer into a recently-shitcanned content moderator (a modern profession similarly concerned with the observation of human behavior now rendered obsolete by the shifting dynamics of social media HR management). Instead of achieving enlightenment through literature, our protagonist discovers a darker kind of transcendence through what I call "True Posting" — becoming the very thing that Chekhov's prisoner rejected: a being consumed by the ephemeral and illusory, which he comes to recognize as realer than even the hyper-real.
What's particularly interesting is how both stories, despite radically different conclusions, deal with the transformation of consciousness through prolonged isolation and limited stimuli. Chekhov's prisoner finds wisdom and detachment; our modern prisoner fachieves a kind of digital gnosis through the "Phone Hand" and "Goon Hand" dialectic I’ve outlined in prior articles.
For those who haven't read Chekhov's original story, I strongly encourage you to do so. It's a skillful exploration of what happens when a human mind is pushed to its limits, forcing us to question what we value and why. The original raises profound questions about the nature of human freedom, the value of knowledge, and the relationship between material wealth and spiritual fulfillment.
This version attempts to pose similar questions about our relationship with digital media. What kind of wisdom — or madness, or straight tea, sis (the "thesis," if you will) — might one achieve through total immersion in the internet's infinite scroll? What does it mean to be "extremely online" in an age when the boundary between IRL and URL existence has blurred to the point at which no useful distinctions between the two can be made?
I hope this parallel helps illuminate both the timeless aspects of Chekhov's themes and the peculiar nature of our tense present — where the solitary confinement of the original story might, to most, seem less daunting than a life without internet access.
Keep on posting and best wishes for a great summer,
Oscar Berkman
He earned the little orange profile checkmark showing he had more than one hundred paying "bratty subs."