The Medium Short — Dumb Money

William J Hammon
10 min readSep 25, 2023

I will fully admit that I’m not a financial expert. My late mother was a payroll accountant for 25 years, and through her I learned how to balance a checkbook and do my taxes. For me, that’s basically good enough. I had a 401(k) when I worked for ESPN, one where I contributed 4% of my income, because that was the max I could deduct and still get a partial match from the company, so that a total of 6% of my salary went into an investment profile. But since my market knowledge isn’t great, at the time I simply decided to allocate everything into low-risk mutual funds that had a steady yield. When I left the company and moved out west, it took so long to get a job that I had to cash out the account and take a tax penalty in order to keep afloat. And for what it’s worth, the fund did well. I had over the course of about seven years put in about $14,000 and when I withdrew, it was worth about $23,000. That’s the biggest financial win I’ve ever had. If I ever have a steady job again where I can make use of such benefits, I will, and I’ll use the same strategy. At best it’ll result in a couple of years’ worth of extra income if and when I ever get to retire, and I’ve made peace with that.

That’s about the extent of my knowledge on how investing works. What I do know, however, is how to construct a game. My literal job is writing and formatting game shows. Depending on my role in a given production, sometimes one of my actual duties is creating the rules, a series of parameters for how the contest is supposed to flow. This also involves trying to break the game so I can anticipate loopholes and other contingencies in case something goes wrong or a contestant lodges a complaint, or worse, tries to sue. The vast majority of those circumstances are highly unlikely, but I have to put myself in that headspace and try to preemptively counter them.

Because of this, I’ve learned to spot the signs to see when a game is unfair or rigged against the players, and even without specific knowledge of the minutiae of the financial industry, it’s plain as day that when it comes to any sort of wealth creation or management, the game is well and truly rigged. We see and hear about it every day. Prices go higher, rents are unsustainable, wages for workers don’t rise in anywhere near the ratio they do for executives, and all the while, the wealthiest among us never miss an opportunity to declare that they’re better than us, often publicly delighting in how they buy political influence and pit the poor against one another to create what is quickly becoming a permanent wage slave class.

So when the little guys do appear to get one up on their corporate overlords, especially by exploiting the very technicalities that the elites do, it can feel cathartic, if not outright inspiring, even if you aren’t one of the beneficiaries. There are times where it feels like we’re on the brink of another French Revolution when it comes to class warfare, so any small victory comes off like a glimmer of hope that we might not hit such an extreme, and that economic equity could be within reach without drastic measures. On the other hand, when we can watch in real time how the powers that be cheat to subvert that tiny moral win, it’s even more dispiriting.

This is the backdrop for Dumb Money, directed by Craig Gillespie (I, Tonya and Cruella) and written by Lauren Schuker Blum and Rebecca Angelo. Based on the Gamestop short squeeze of 2021, the film takes a hyperactive, almost bombastic approach to the incident, basking in the viral craze of the moment while also attempting to expose the bad actors who never play by the rules (which on a meta level is a little bit rich coming from the director of a Disney remake prequel and which is co-produced by the Winklevoss twins).

On the surface, this is a great idea, especially given the timeliness of the story, which had the double effect of temporarily sticking it to the suits while also providing a moment of levity during the COVID pandemic. And to be clear, this is a good movie. However, you can’t help but compare this to The Big Short, which was groundbreaking on this very subject just a few years ago, and is one of the best films of the last decade. On that level, this falls a bit short, but if you can set that aside, you’re going to enjoy yourself.

For those unaware of the newsworthy event, here’s the redux. A non-executive financial worker named Keith Gill (Paul Dano, giving another excellent performance), who keeps up a YouTube channel on the side, sees signs that Gamestop — the well-known retail store for video games — was trading below what he felt was its true value, and through online communities (chiefly Reddit’s WallStreetBets discord), he basically told people that he liked the stock, and that encouraged “retail investors” (individuals and non-financial people) to buy it up, thus raising the share price significantly, including a huge surge in January 2021. Gamestop had been trading at just a few dollars when the whole thing started, but it eventually peaked at over $400.

This made a lot of small-time traders richer than they’d ever been, and increased the company’s value by billions. It also pissed off hedge fund managers, who had “shorted” the stock, causing them to lose a ton of money. Again, setting the nuance aside, especially because Adam McKay explained it so much better, essentially “shorting” a stock is a convoluted way for investors to bank on a company losing value, because nothing says “America” like profiting by betting against industry and on human suffering. As such, much chicanery and shenanigans ensued, culminating in Congressional hearings about the malfeasance of the wealthy interests.

That’s the story in a nutshell. What really matters is how it’s told. The film basically plays the events through three concurrent threads. There’s Gill’s life, both with the stock and his family (particularly Shailene Woodley as his wife and Pete Davidson as his brother), there are the reactions from the wealthy fund managers trying to navigate this peasant uprising (Seth Rogen as Gabe Plotkin, Nick Offerman as Kenneth Griffin, Vincent D’Onofrio as Steve Cohen, and Sebastian Stan and Rushi Kota as Robinhood founders Vlad Tenev and Baiju Bhatt), and there are the “real life” experiences (i.e. composite characters who may be very loosely based on actual people) of the retail investors “holding the line” on the stock (America Ferrera as a nurse, Anthony Ramos as a Gamestop employee, and Myha’la Herrold and Talia Ryder as college girlfriends).

At first glance, these dynamics are meant to establish the average joes that the elites playfully refer to by the film’s titular epitaph, implying that commoners are too stupid to properly play the market, and as such their cash is free for the taking. However, whether intentionally or not, the way it ends up working best is in how the picture shows that regardless of class status, everyone involved is a fuckup to some degree. On Gill’s side, he’s barely able to make ends meet, and he’s gambling a lot of his savings on this investment, as he’s the first of his family to graduate college and thus has the best opportunity for social mobility. This is contrasted with the fact that his brother Kevin is a complete washout, working as a Doordash driver who actively eats the food his customers order because it’s not like their small Massachusetts suburb is bursting with delivery options, especially in a pandemic. For the other investors, no matter how noble their intentions are or how committed they are to winning one for the working man, they are all betting their financial futures on one guy’s hunch and a slew of TikTok videos.

And then there are the moneyed interests, where the film comes closest to achieving the satirical heights of its spiritual forebear. Active steps are taken by Griffin, Cohen, and others, all of whom basically hate each other, to fix the outcome and prevent people from buying Gamestop stock so that their shorts will pay off. Despite their mutual disdain, they feed off each other, needing one another’s backing in the most parasitic of fashions in order to maintain the status quo and keep themselves in luxury (Rogen’s Plotkin, for instance, begins the film by yelling into a phone about why his pool hasn’t been converted into a tennis court yet so that he can invite more wealthy people over to his mansion and leech off of them for capital).

It goes even further when it comes to Plotkin, Tenev, and Bhatt. All three of them, to different extents, see themselves as outsiders who worked their way into the inner financial circles. Plotkin tells a family anecdote about his grandfather working his way up the ranks at a grocery store to becoming a manager, which paved the way for him to get into Northwestern and eventually become a multimillionaire investor. Tenev and Bhatt promote Robinhood as the outlet for anyone to invest and live the American dream like them as immigrants. But at the end of the day, they’re still beholden to the likes of Griffin and Cohen, old money, who control the game and see them as just as disposable of pawns as the unwashed masses trying to keep a video game store afloat. The visual irony of all this (coupled with some truly hilarious scenes relating to their remote Congressional testimonies) truly reinforces this idea that all of this is basically chance. The problem is that those at the top get to commandeer the best odds for themselves.

A lot of this works because of the cast giving it all they’ve got. Dano (despite looking more like Vlad Tenev than Keith Gill; seriously, look at the source footage reveals during the credits) is incredibly expressive and genuine in his performance. Ferrera tugs at the heartstrings at just the right frequency. Even Pete Davidson, for what is likely the first time ever, got a few laughs out of me. It took a LONG time in the movie for it to happen, but eventually even that rampaging asshat got a few chuckles because he kept selling Kevin’s character the right way. Credit where it’s due. Trust me, I was as shocked as anyone when the “HA!” escaped my lips.

Where the movie falters is in its lack of eloquence. Maybe that’s sort of the point, because the people involved aren’t supposed to be all that polished, but there were moments and elements that just rang false for me, especially when put in the same conversation as The Big Short. That film had fun, creative asides to teach the audience the nuance of all the fuckery in the financial industry that led to the 2008 crash. This picture, on the other hand, has a couple of offhanded lines of dialogue about how the common man is getting screwed, but most of it is drowned out by a ton of montages of social media clips and commentary, Gen-Z slang, and some of the whitest people you could ever meet rapping along to Kendrick Lamar and Megan Thee Stallion. Even the few minorities in the cast can’t pull this off, as no one for even a single second would buy America Ferrera saying, “Bitch, sit down. Be humble.” And I’m sorry, can we get off of “WAP” already? It’s a shit track, performed shittily, that only has shitty novelty value, and its lifespan was artificially inflated by fake controversy from shitty pundits. I’m not saying you can’t like it, but I am saying it has no reason to be in two separate movies this year so far (the other being Joy Ride), performed by actors who have no business doing so. You guys do realize putting Doja Cat in Elvis was a BAD idea, right? That it shouldn’t be replicated… right?

Anyway, my point is that Adam McKay’s flick took the time to ensure the audience understood just how badly they were being bled dry, and in doing so found a way to make all these villains funny, thereby creating a positive experience in the face of criminal tragedy. Dumb Money, on the other hand, seems to be more performative, paying lip service to society’s ills enough to make you want to revisit the Occupy Wall Street movement, but not really showing their work about why we should laugh while still being righteously pissed. It comes close fairly often, but it never quite gets there. Because of that, while we can engage with and enjoy the material, there are parts that also feel hollow, like posting the net worth of fictional characters at the beginning and end of the movie. Like investing in crypto, there’s nothing really there, no matter how much fun it may feel in the moment. This is a good movie, one I’m still recommending, but it sold its shares just shy of being truly great and essential.

Grade: B

Join the conversation in the comments below! What film should I review next? How vast is your knowledge of the financial markets? No seriously, though, where is this generation’s Madame Defarge? Let me know! And remember, you can follow me on Twitter (fuck “X”) and YouTube for more content!

Originally published at on September 25, 2023.



William J Hammon

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