Substack Is at the Gambling Stage of Desperation

Substack is at the Gambling Stage of Desperation Subscribe Sign in Substack is at the Gambling Stage of Desperation Big tech's political agenda is coming for you, and your wallet. S Peter Davis Feb 27, 2026 60 6 33 Share Some men are probably coming to break Chris Best’s legs. That’s the best explanation for why Substack is entering an exclusive partnership with Polymarket as announced in a comments-disabled post from Substack’s Official Substack, a newsletter that has nearly 6 million subscribers. The post got fewer than one thousand likes. It didn’t even crack 800. This is an unpopular thing, is what I’m trying to get across. It’s not as unpopular as Substack’s numerous Nazi-related PR disasters, like when it sent a push alert with a swastika on it to a bunch of people’s phones, but the general sentiment swirls around somewhere between negative and confused . If you’re in the confused camp you might be someone who doesn’t really know what “Polymarket” is. I was one those people. It’s an app that lets you participate in “prediction markets,” which is also something a lot of people don’t understand. So here’s the basic 101 about prediction markets: What the hell is a prediction market? It’s betting. No, really, that’s it. It’s a gambling app. It’s just unregulated gambling, the internet equivalent of a smoke-filled basement with a bunch of people screaming “di di mau!!” at you. It was literally illegal in the United States until late last year when Donald Trump legalized it in exchange for adding his son to its advisory board . How many good things can you think of that were illegal until Donald Trump legalized them in order to enrich himself personally? What’s the track record on that? Prediction markets are functionally literally identical to what we call sports betting except that they aren’t limited to sports. I hate to abuse the word “literally” but I don’t want to give you the impression that there is any nuance: It is literally betting in the same way that a dog is literally a canine. Now, with one click of the mouse, you can insert a widget into your newsletter that allows your readers to place a quick bet on, for example, when the USA is next going to kill a ton of people in a foreign country. Isn’t this fun and not grim at all? This is just a screenshot, I’m not going to actually do the link embed, screw that noise. So why are so many people confused about this? It’s probably because, in no way, shape, or form does Substack, at any point, describe it as such. Instead, it prefers to describe it as “an emerging technology that aggregates real-time estimates of what will happen in the future.” Furthermore, “Polymarket lets people trade shares of future events, like elections, economic trends, and scientific breakthroughs. The price reflects a market estimate of how likely an outcome is to happen.” That’s like saying “facilitating the controlled release of surplus solid assets from a stakeholder into downstream processing infrastructure in conjunction with multi-phase remediation strategy” to describe the act of taking a shit. Fuck you. It’s betting. Every place on the internet that has no skin in the game including Wikipedia just matter-of-fact calls it betting, as a synonym. But Chris Best, Substack CEO, wants to ease you into the idea that it is, in fact, sweet child, actually, a stock market . You’re not betting on, for example, when the next broad-daylight ICE murder is going to occur—actually, you’re trading shares of a future event , namely, the next broad-daylight ICE murder. See the difference? But, friends, prediction markets are not markets. The very term itself was devised by a marketing firm and voted on in a boardroom from a short list of phrases to best trick the target demographic into thinking this is not gambling. Polymarket and their competitors came up with the term “prediction market” specifically to dodge gambling laws . It’s not some new buzzy Silicon Valley tech concept. That’s why they did it . There are at least 33 countries , including mine, that see through this very obvious ruse and have banned Polymarket for refusing to abide by gambling laws. Until Trump, the USA was one of them. Here’s the main difference: In the stock market, you’re actually purchasing a stake in a company. True, for the average individual the stake rounds down to nothing, but it’s like gravity—there is a reciprocal force, even if you will never feel the pull that you exert upon the Earth, the actions of shareholders as a total mass can make or break a company. If enough people sold their Tesla shares right now, they could actually weaken Elon Musk to the point where he could be in federal prison, where he belongs, by next Friday. When you’re “””buying shares””” on whether Erika Kirk gives birth to JD Vance’s love child this year, you’re not actually purchasing anything. You are not, in any kind of way, exerting any force whatsoever on the chances of that happening. What you are doing is that you are putting down money on a thing happening, and if the thing happens, you get more money, and if the thing doesn’t happen, you lose the money you put down. What’s that called? Oh, it’s on the tip of my tongue, starts with a G. Guacamole? Substack added a gambling widget to their app. Now you can just seamlessly drop a link to a sportsbook between the lines of your newsletter to entice your readers to quickly place a bet on that thing you’re talking about. Midterms are coming up and a lot of political newsletters are going to start discussing candidates and hey, while we’re on the topic, why not drop a few quid on your fave? It’s super easy now. And just to be clear— literally everybody hates this . Everybody. You can even drop a gambling link in a post on Substack’s microblogging social feed, Notes . There’s a button right there. There are people in recovery from legitimate serious addictions who are going to have to avoid the site now in case someone slips a Polymarket link in their feed like a roofie. I haven’t seen a single person who likes or wants this. Alex Dobrenko hates this. Alex Dobrenko` is practically the mascot of the website. This is like Mickey Mouse calling Bob Iger a fucking dumbass. Here’s what paid subscribers are reading right now: Sign up or upgrade here:. Subscribe So why would they do this? Let me break it down: If you’ve followed me for a while then you know, but if I may refer back to what I said just last year and also the year before that because that’s how long the cracks have been showing, the ultimate reason is these shitbags: Not just them, but they’re my favorite avatars of the general concept just because they look like such goofy ass comic supervillains but also because these two men are legitimately two of the worst human beings alive. Seriously, they’re way up there. That’s Ben Horowitz and Marc Andreessen, and together they are the venture capital dynamic duo Andreessen-Horowitz, frequently nicknamed “a16z” because there are 16 letters between A and Z and nobody gives a shit about any of them. Around a third of them are “E.” These are the guys who are getting ready to send a few goons down to Substack HQ with a crowbar to sort them out if they don’t make some changes fast. Stick with me, I’m going to explain this in the least dry way I can Venture capital is also kind of gambling. It’s basically rich people who keep a company afloat before it’s profitable. They’re paying your bills and your staff salaries while you get on your feet and figure out how you’re going to make money on your own. It’s not a loan, exactly, because they get private equity and don’t charge interest, but in principle it’s the same type of reptile motivation that drives almost everything—they give you some money with the mutual understanding that you’re eventually going to give them back much more money later. The thing is, even though venture capitalists are gambling, they also never really lose—because, you see, they’re the House. VCs like a16z fund startups like Substack under the condition that they’re either going to be paid back tenfold when the startup becomes massively successful, or else they’ll get something else beneficial out of the relationship. What those little toads up there need Substack to do is undergo what’s called a “liquidity event,” which is either going public or being bought by another company. That converts the VC’s stake in the company into money that they can cash out. But for that to happen, the company needs to be profitable. The more profitable, the better. Substack’s business model, as far as I can tell from public information, is still very far from being profitable. Its business model just isn’t very good—its no-fee-for-writers platform is extremely top-heavy with free and low quality blogs, rife with the free-rider problem that weighs down their infrastructure. This in combination with their taking a percentage cut from writer earnings instead of the flat monthly hosting fee that most other newsletter platforms charge means that they are not just relying on the whales—the biggest earners—to subsidize the platform, they’re also relying on the absolute loyalty of those whales. If Matt Taibbi, for example, is shedding five thousand dollars a month— rising with scale —into Substack’s coffers when he could be paying a flat five hundred a month to skip on over to Ghost (these numbers aren’t accurate, I’m just roughly spitballing) then there’s literally no reason to stick with Substack beyond brand loyalty, and as this gap expands exponentially, that’s a diminishing fuck-ton expectation of brand loyalty. Substack has no road to profitability through subscriptions alone. They’re scrambling for other revenue streams, and they keep saying they don’t want to insert a bunch of advertising everywhere, which is literally the only known escape hatch from this situation . They still have to keep Marc Andreessen happy enough somehow to keep the lights on. It helps if you pander to him by making Substack part of his shitty techbro worldwide social mindfuck experiment. So maybe if Substack can’t make money for itself, it’s still worth keeping around if it can make money for Polymarket. Andreessen-Horowitz are deeply evil, misanthropic ghouls During an interview between Substack CEO Chris Best and tech journalist Alex Heath , Heath asked whether Polymarket was paying Substack an assfuck-bitch-ton of money (my paraphrase) to embed their gambling tools into every inch of the Substack interface, and Best paused awkwardly before pleading “no comment” in the most obviously “yes” way in the history of human conspiracy. Polymarket is spreading its embeds all over the internet like a rash along with its rival Kalshi, to the extent that they can be called rivals because a16z is funding both of them . These guys are all about trapping you, me, all of us into a permanent state of braindead catatonia in which all we do all day is doom scroll and click buttons that send money to billionaires. The most reprehensible way that they do this is they turn ruining your life and giving your money to billionaires into a fun game for you to play. Here’s another startup currently being funded by horror movie villains Andreessen and Horowitz: It’s called Coverd : According to their pitch: We disrupt personal finance through gamification, starting by offering up to 100% cash back on any purchases with the Coverd Card. Coverd offers users comprehensive spending insights and thrilling games to win back their purchases: from covering credit card purchases to winning tickets to a dream event for as little as $1. What’s that? Is that the sound of vague and gimmicky marketing copy I hear? Could it be covering for something else? Perhaps… gambling? Yeah, it’s gambling. You know what you’re gambling on? Your fucking credit card debt . That’s right! Spend spend spend! Crank that lever and watch the reels fly. Don’t let your hand tremble as you buy those tokens with money you don’t have, they’re your eventual ticket out of financial ruin! Just keep on spending, just one lucky roll and all of this will go away. Ayy, I’m about to lose my house If that’s not the most ghoulish thing you’ve read today, then you’ve probably been reading the Epstein files again. Gamification (turning stuff into a game) is the hottest new philosophy in Silicon Valley, but also the far-right in general. The current craze began with Robinhood, the stock investment app. Investment drives these companies so they want everyone to do it, but it’s usually something only well-off people do because it’s boring, it feels like work, and it’s only appealing if you have a fair amount of disposable income. Robinhood gamified stock trading. It turned it into a fun game, made it appealing to people who wouldn’t ordinarily bother with it. It opened up more wallets and got more money flowing through Silicon Valley that would ordinarily be spent on material things. Guess who was behind Robinhood? That’s right! Andreessen-Horowitz. They discovered the infinite money hack for the Millennial brain was online gaming. So how else could they expand on this? Take everything that young people are into, that isn’t already a game, and gamify it. Gamify spending. Gamify debt. Make a TikTok for sports clips, and gamify it . Put microtransactions everywhere. Every time you read about something in the media there should be a button next to it that lets you place a bet on something. They gamified scrolling, they gamified social media. Now they’re gamifying newsletters. This is an insidious tool that has become intrinsic to the way that the modern far-right manipulate the populace: Make it a game. The whole thrust of the “Gamergate” movement that led up to Trump’s first election, which was groomed and fomented by Steve Bannon, was the gamification of Millennial antifeminist rage. They recognized that so many of these people were into games, and they channeled their anger into a game. Made online harassment into a game. Actually and literally This is psychological warfare We’re basically at a point where the glowing rectangles that we stare into all day have become the abyss that Nietzsche warned us about. Everything we interact with on the internet now is trying to control us in some way, and people like Marc Andreessen and Ben Horowitz and Steve Bannon and Elon Musk and Mark Zuckerberg and Jeff Bezos and the goddamn Ellisons who are taking over American media are united in one mission to groom your political beliefs, access your wallets, get the money flowing upward into the venture capital class. Substack is an easy mark. Even though they dominate the market for newsletters by far, other newsletter platforms like Beehiiv have a shorter road to profitability . Substack’s incredible momentum is powered by the very thing that makes it unsustainable—the fact that it’s free. As it becomes increasingly dependent on ghouls like Andreessen and Horowitz to keep it afloat, it will become increasingly amenable to their political and social agenda. Polymarket is just the beginning, and I don’t want this to sound like this problem is just a Substack thing, either. Substack is uniquely susceptible, which just makes them the canary in the coal mine. This bullshit is coming for the whole internet, and it’s coming soon. You can bet on it. On Polymarket, probably. I'm writing a book about how the emergence of Silicon Valley and the internet forged a generation of reactionaries that has led us to the resurgence of far-right politics that we are suffering through today. The working title is How Geeks Ate the World and I’m going to be dropping parts of the draft into this very newsletter as the project comes along—but only for paid subscribers. So if you want to read along in real time, please consider subscribing. Otherwise I’ll be keeping you in the loop. Check it out here: You can sign up or upgrade here! Subscribe Here’s what paid subscribers are reading right now: Why the Right Will Never Dominate Entertainment S Peter Davis · Mar 6 It’s plain to see that the carnival of horror clowns squatting in the United States government are attempting some kind of top-down cultural revolution by force, to replace the dominant western culture with nebulous “anti-woke” and thinly veiled white supremacist sensibilities. Read full story 60 6 33 Share Discussion about this post Comments Restacks Dmitrii Zelenskii 3d Liked by S Peter Davis That is _hilarious_. Kinda true, but also omits a very important factor. Many big names of Substack that have no particular enthrallment to a16z: Scott Alexander, Nate Silver, Bryan Caplan, Robin Hanson, the list goes on — love prediction markets for idiosyncretic reasons (basically, they love them as an epistemic tool not as gambling device; there's a reason Manifold, which is fake-money, is used by a number of them just alongside Polymarket and Kaishi). I imagine this is really as easy as "our whales love this feature, and Polymarket is ready to pay for it". Reply Share 1 reply NickS (WA) 3d Possibly of interest to some readers -- a simple way to build-your-own paywall. https://tedium.co/2026/03/08/minimal-paywall-setup-idea/ Reply Share 4 more comments... Top Latest Discussions No posts Ready for more? Subscribe © 2026 S Peter Davis · Privacy ∙ Terms ∙ Collection notice Start your Substack Get the app Substack is the home for great culture