Legendary Reddit Thread: Yishan Wong's 'Hypothetical' Long Con to Reclaim Reddit, with a Cameo by Sam Altman

Level 1: Taking Back Your Toy

Imagine you had a favorite toy that you and your friend made together. You ended up giving it to a big older kid (let’s say, an adult or a big company) because you thought they could take care of it. But the big kid didn’t really understand the toy or play with it well. You start to feel like giving it away was a mistake. So, you and your friends come up with a sneaky plan to get your toy back.

First, you get one of your buddies hired as the toy’s manager in the big kid’s house. This friend acts super helpful and says, “Hey, to make this toy even cooler, we should let other kids have a share of it!” The big kid agrees, and now a bunch of your friends each own a small piece of the toy. That means the big kid’s own share of the toy gets smaller. Next, your other clever friend (let’s call him Sam) and some pals say, “We’ll also help take care of the toy if you give us some shares.” The big kid, who doesn’t really get what’s happening, says “Sure.” Now even more of the toy is owned by your crowd and your friend Sam even gets to sit in on the toy’s “decision meetings.” Finally, your buddy who was the manager suddenly quits on the spot, causing a big panic. The big kid freaks out because now the toy has no leader. Your friend Sam uses this moment to say, “Hey, why not let the original kids (you and your friend who made the toy) come back to run it? They know it best!” Desperate, the big kid agrees. Boom – you and your friend are back in charge of your beloved toy! The big kid is left owning only a tiny piece of it and can’t boss it around anymore.

Now here’s why it’s funny: after pulling off this whole secret mission and basically outsmarting the older kid, your friend Sam just casually says to the buddy who quit, “Cool story, bro… thanks for doing all that work, haha.” It’s like one friend spent hours setting up an elaborate prank, and another friend just smirks and says, “Eh, that was easy for me, but thanks for helping!” The humor is in how over-the-top the plan was — it sounds like a cartoon plot — and how nonchalantly they talk about it afterward. It’s funny and satisfying because the little guys (you and your friends) used a clever trick to get your toy back from the big clueless owner, and then they joke about it as if it was no big deal. It’s basically a tech world version of a kid’s heist story, where the geniuses win and then wink at each other in the end.

Level 2: Rescuing Reddit 101

Let’s break down what’s going on in simpler terms. This meme is a screenshot of a Reddit Q&A thread (AskReddit) where someone asked, “What’s the best ‘long con’ you ever pulled?” A "long con" means an elaborate long-term trick or plan to deceive someone. User yishan (who is actually Yishan Wong, a former CEO of Reddit) answered with a jaw-dropping story: basically, how Reddit’s original founders and their friends might have secretly plotted to get Reddit back after selling it to a big company. Reddit was sold to Condé Nast (a huge old publishing company) in 2006. Yishan’s comment describes a step-by-step startup_power_play – essentially a plan to rescue Reddit from its new owner. Here’s what he claimed happened (with some ManagementHumor in the telling):

1. Recruit an insider CEO: The Reddit founders and Y Combinator (Reddit’s early investor/incubator) helped install a friendly CEO (chief executive officer) – in this case, Yishan himself – to run Reddit. Alexis Ohanian (Reddit’s co-founder) was on the hiring panel and made sure to pick the one guy in on the plan.
2. Demand employee equity: This new CEO insists that to hire top engineers, Reddit needs to offer equity (shares of the company) to employees. That sounds normal for startups, but here it was a tactic: giving employees shares would dilute Condé Nast’s ownership (meaning Condé Nast’s percentage of Reddit would shrink because others now own pieces).
3. Bring in new investors: As Reddit kept growing, the CEO then raises money from Silicon Valley investors, led by Sam Altman (who was President of Y Combinator). When a company raises money, new shares are given to investors – further reducing the old owner’s share. Sam Altman also got a board seat (a position on Reddit’s board of directors – the group that makes big decisions like hiring/firing CEOs). This gave the Silicon Valley crew more control and a say in Reddit’s future.
4. Stage a leadership crisis: Now the sneaky part – the CEO and team create some kind of leadership turmoil (imagine sudden resignations or conflicts at the top). This chaos makes the board scramble to find new leadership. Since Sam Altman is on the board, he uses that power to suggest bringing back Reddit’s original founders to steady the ship. Essentially, the people who created Reddit (like Alexis Ohanian and Steve Huffman) are invited to take over again as leaders.
5. Founders regain control: In the end, Condé Nast (the old owner) is left with only a minority stake (less ownership than the combined others) and no longer calls the shots. The founders are back in charge of their “baby,” and the company is run more like a tech startup again rather than a media subsidiary.

Yishan ended this detailed saga with a big “JUST KIDDING”, as if to say “ha ha, of course we didn’t actually do that.” 😉 It reads like a suspense novel about a boardroom coup (a coup is a sudden takeover), and if you’re new to StartupCulture, it might sound far-fetched. But here’s the kicker: Sam Altman himself replies in the screenshot, basically confirming the story with a side of snark. Sam’s reply in the yellow box says, “Cool story bro. Except I could never have predicted the part where you resigned on the spot :) Other than that, child’s play for me… thanks for your service as CEO.” Let’s unpack that:

• “Cool story bro.” – This is a meme-y, sarcastic way to say “Nice tale,” often used when someone tells an unbelievable story. Sam starts with this to be tongue-in-cheek.
• “I could never have predicted the part where you resigned on the spot :)” – In real life, Yishan resigned abruptly as CEO in 2014 (meaning he quit suddenly, surprising everyone). Sam is teasing that out of all the complex plotting, the only twist he didn’t foresee was Yishan quitting unexpectedly. The smiley face :) emphasizes it’s a light-hearted jab.
• “Other than that, child’s play for me.” – “Child’s play” means something very easy. Sam is facetiously bragging that aside from Yishan’s surprise resignation, the whole scheme was easy for him to pull off. In other words, this long con was no big challenge. This is classic IndustryIrony – he’s jokingly flexing that these high-stakes maneuvers were just routine.
• “Thanks for the help. I mean, thanks for your service as CEO.” – Ouch! Here Sam basically says “Thanks for playing your part, Yishan.” “Thanks for your service” is a phrase often used formally (for example, to someone leaving a position), but here it’s dripping with irony. It implies Yishan was just a helpful pawn in the plan. Sam is half-joking, half-roasting Yishan by implying the only reason Yishan was CEO was to execute this plot and then bow out. It’s a very pointed way to thank someone, and in context it’s quite funny because of the audacity.

For a junior developer or someone new to TechHistory, what’s funny is the sheer ridiculousness and boldness of this story – and the fact that the people involved are commenting about it openly on Reddit. Imagine reading a serious-sounding insider story about how a company was taken over from the inside, and then seeing one of the key people go, “Yep, pretty much – we did that, thanks dude!” It’s an industry in-joke because it references real events: Reddit’s tumultuous journey from being owned by a big traditional company back to being run by its founders with startup investors. Folks who follow StartupCulture recognize the pattern of seller’s remorse (founders regretting selling their startup) and loved seeing it described as a cheeky heist. The meme blends TechHistoryAndIndustryAnalysis (the factual background of Reddit’s ownership changes) with ManagementHumor (boardroom tactics presented like a comedy sketch). Even if you don’t know all the names, the idea of a “long con” to take back a beloved product from clueless owners is a relatable narrative in tech. And Sam Altman’s cool, cutting response is the comedic punchline that makes everyone go “wow!” and laugh at how casually these power moves are treated.

Level 3: Startup 4D Chess

This meme digs into Silicon Valley corporate intrigue with a tale so elaborate it borders on Machiavellian satire. In true StartupCulture fashion, a former Reddit CEO (Yishan Wong) wrote a detailed "long con" scenario on an AskReddit thread, describing how Reddit’s founders and allies might have outsmarted a 100-year-old media conglomerate (Condé Nast) to wrest back control of their company. The strategy reads like a playbook for boardroom 4D chess: secretly plant a friendly CEO, dilute the parent company’s stake under the guise of hiring incentives, bring in sympathetic investors (led by Sam Altman, then Y Combinator’s president) to gain board influence, and finally stage-manage crises that pave the way for the return of the prodigal founders. It’s a TechHistory caper mixing Startup hustle with CorporateCulture cunning—a story that hits home for veteran techies who remember all the exit-then-regret sagas of the Web 2.0 era. Reddit’s 2006 sale to Condé Nast was widely seen as premature, a classic case of a vibrant online community languishing under an old-media owner who “didn’t understand it.” This made the imagined conspiracy especially juicy: it addresses that itch every startup founder feels after selling out too early—the dream of a daring take-back.

What really sells the humor is the deadpan way it’s delivered and confirmed. Yishan ends his dramatic exposition with a tongue-in-cheek “JUST KIDDING. There’s no way that could happen.” Enter Sam Altman in the comments with the ultimate mic-drop IndustryIrony:

samaltman (9 years ago): "Cool story bro. Except I could never have predicted the part where you resigned on the spot :) Other than that, child's play for me. Thanks for the help. I mean, thanks for your service as CEO."

In one swoop, Altman turns a wall-of-text industry in-joke into a roast. His reply essentially says “Nice long con, exactly what I’d do — with one surprise twist.” ManagementHumor shines through as he jabs at Yishan’s abrupt resignation (an actual event in Reddit’s turbulent leadership saga) that even the master schemers didn’t foresee. For seasoned engineers and founders, the exchange is hilarious because it’s both wildly audacious and plausibly true. It’s like discovering that the conspiracies whispered in startup bars were real all along. The meme captures that cathartic blend of schadenfreude and vindication: seeing savvy Silicon Valley insiders pull off moves that make boardroom drama feel like an open-source project—complete with commit history in a Reddit thread. It’s an insider laugh at how StakeholderManagement sometimes involves Trojan-horse CEOs and boardroom_4d_chess. In short, the humor comes from recognizing this as the ultimate tech long con: a mastermind level stunt that StartupCulture veterans half-joke about but rarely see spelled out (and confirmed!) in public.