Everyone loves an underdog. But in 2012, when Jaime Rogozinski founded WallStreetBets, the rowdy but resourceful subreddit dedicated to sharing the trials and tribulations of playing the stock market, he created an army of them.

Most Americans learned about the power of that army nearly a decade later, when it led a financial rebellion against Wall Street bigwigs by bulk-buying shares of GameStop. Fueled by a steadfast belief in the company’s promise, the Reddit legion managed to send GameStop soaring, so much so that Robinhood was forced to restrict trading on the stock. In the end, hedge funds like Melvin Capital abandoned their short positions while leaving scores of average joes significantly better off. It was a David and Goliath story that flummoxed the business press, exposed the perils of parking cash in Robinhood, and shed light on the newfound, disruptive potential of the retail investor.

But the full story of WallStreetBets, as Nathaniel Popper writes in his new book, The Trolls of Wall Street, began long before all that. Popper, a former New York Times journalist who covers the intersection of finance and technology, argues that the movement found its roots in the aftermath of the 2008 financial crisis—a time, he writes, of “distrust and cynicism,” in which lonely, laddish young men were able to find solace together in online trading.

In speaking with Rogozinski as well as countless moderators of WallStreetBets, Popper traces the community back to its salad days, when members would take out risky options contracts and perversely delight at the sight of their bank balance dwindling. Things took a turn in 2013, when Robinhood—in many ways, dangerously—set out to democratize the playing field for retail investors, leading to the subreddit’s transformation into a full-fledged market-mover. As the site grew in tandem with the rise of divisive figures like Donald Trump and Elon Musk, managing its internal fracas proved a perpetual challenge—particularly when it came to hate speech and crypto. But the site held together. And by February 2020, when COVID crashed the stock market—which many WallStreetBetters leveraged into a windfall—it was becoming clear that this young crowd of upstart investors was far more sophisticated than their forebears. “The new world of online money,” writes Popper, had “given rise to a bunch of self-described trolls and degenerates with an unprecedented knowledge of the levers that make the economy work.”

In an interview with Vanity Fair, which has been edited for length and clarity, Popper talks about the “complicated factors” behind WallStreetBets’ rise to prominence, why the internet’s “law of attention” has insulated Robinhood from bad publicity, and how the legacy of the GameStop saga continues to animate the hottest trends in institutional trading. “The way the general public thinks about [a] company is now very important to the financial success of that company,” he says. “There’s this whole new element in the financial world now that Wall Street didn’t see coming.”

Vanity Fair: What inspired you to write the book, and what informed your reporting process? I feel like with any subreddit, there’s just this endless wealth of online material to sift through. So how did you decide who to talk to and what to pick out?

Nathaniel Popper: This started as a book about GameStop. And, as I dove into it, I realized that Gamestop was too narrow a lens to look at this through—that there was this much bigger story here that I and most people had missed. And it was this story of generational change in the way that young people related to the markets and stocks and the financial world. What I realized is that there’s this movement that young people had become part of youthful pop culture in a way that most people who were above the age of 35 weren’t really aware of. Because you have this social media record—all of this documentation—you could tell the story of the growth of this community and this new, strange online world in real time. It was like somebody was there filming the whole thing as it happened. As I looked around, I felt like there are not very many people who have taken advantage of the opportunity that social media offers to tell histories of these movements. It’s a really candid window into this whole world.

I was really struck by how you didn’t even get to Gamestop in the book until page 180. There’s this whole sociocultural lead-up that you outlined in the book with things like the manosphere and 4chan and [Occupy Wall Street]…

And Trump.

And Trump. Talk about why you made that narrative choice to start well before 2012.

Yeah, this really goes back to the financial crisis. Millennials sort of came of age during the financial crisis. And in the years right after the financial crisis, there was this idea that young people were going to be forever estranged from money and finance; that was the moment where socialism seemed like the ascendant ideology. Young people just were not interested in the stock market. What I realized is there was, like, this crazy journey in which that was totally turned on its head over the next decade to where they are trading and investing and spending more time on the stock markets than any young generation that has before. And, you know, now you meet any 15- to 17-year-old boy, and there’s, like, a 50% to 75% chance that they’re going to have Robinhood and Coinbase on their phone. And this is what they talk about with their friends instead of, like, the NBA or video games. This is the new youthful obsession.

But there are also darker elements to this. Can you talk a little bit about the ways that informs some of the culture in WallStreetBets and also continues to inform some of the stock market gurus of the present?

Part of the reason I went back to the financial crisis is that the crisis created this sense of alienation and distrust, that has informed everything that’s come since and that has informed so much of online culture. It was parallel to the way distrust gave rise to Donald Trump. So these were not hopeful movements. These were not movements that were about some positive vision of the future; all of this online ferment was about not trusting older people and not trusting the ways that we used to do things. The rise of social media just put that into overdrive.

This all began with a rejection of the ways that previous generations had come to think that you should do things, that there was a polite and normal way to do politics and a polite and normal way to deal with your money. And the polite way was, you responsibly put your money into index funds and just wait for it to grow and you don’t take risks. And this new generation was just was drawn to the idea that of like, Fuck that; the safe, responsible way is just not appealing to us. And there are many complicated factors behind that. But, again, I sort of keep coming back to this idea that so many of those complicated factors are the same ones that lead people to embrace this presidential candidate who was positioning himself as the antipresident. To understand that is to understand so much of online culture. You know, it’s no surprise that here we are now, in this moment where Trump is getting surprising levels of support from young voters and minority voters—all of this is a swirl of distrust that is just incredibly pervasive right now.

Yeah, I almost feel like Donald Trump did to politics what WallStreetBets did to Wall Street. It wasn’t like capital c Conservatives dominated WallStreetBets. They just felt spurned by the financial crisis and wanted to upset the powers that be and felt like Donald Trump was their antiestablishment rabble-rouser who could turn everything upside down.

Yeah, it’s this chaos agenda, as I think Derek Thompson referred to it [in The Atlantic]. It’s just this idea that the only thing you can do is be disruptive—that that is the easiest way to feel powerful in this world where so many people just feel powerless.

I want to get to the whole GameStop saga. I was also struck by the amazing portrait you paint of the internecine battles that were playing out in WallStreetBets [at the time]. I just felt like a lot of the media coverage was all about Wall Street versus WallStreetBets—when, really, there was just as much, if not more, conflict happening within the subreddit about what type of speech was allowed, what type of financial products were allowed to be talked about, etc. Do you think you could talk a little bit more about why you focused so much on the internal fractus?

What I wanted to capture was how these new, decentralized online communities work. Because these communities—whether they’re subreddits or Facebook groups or Discord servers—are where young people are spending their lives. This to me was like an anthropological visit to a commune in the ’60s or ’70s, right? With communes, they were, like, the far edge of how people were experimenting with how you should live your life. And to me, that told you something about mainstream culture.

WallStreetBets is not just this website where people post things and then people write answers below it. It was a community that had personalities and people talking to each other, but then it also had this universe of chat rooms, where hundreds of thousands of people were talking, throwing ideas back and forth. So understanding how this new kind of community is governed feels very essential to understanding how young people are living their lives. It’s messy, just like those utopian communes were back in the ’60s and ’70s. They’re fighting for power, they’re fighting for ideas and what they stand for and what they should stand for. And so there were these constant battles between the moderators over what this community should mean, as well as the constant petty human side of it that’s always there.

It can’t be understated just how important the rise of Robinhood was for this community—in terms of “democratizing” the playing field for the retail investor and—and how it allowed average joes to explore riskier types of trades. [In reading your book], I was reminded just how much reputational damage Robinhood suffered when they halted trading on GameStop. Why do you think Robinhood was able to come out of that pretty unscathed?

One of the things I learned was that Robinhood just had crisis after crisis. Every year when they were recruiting in 2015, their backend systems would just break down. But each crisis seemed to only make the app more popular, and give them more customers. It meant, to me, that Robinhood could turn a crisis into an opportunity for growth.

It made me realize that there’s this new law of attention on the internet, in which it doesn’t matter whether the attention is bad or good; it just matters that you get attention. So the crises for Robinhood would make people more aware that Robinhood existed and make people and would draw in a new wave of customers that would make the app even bigger. This is another place where it feels like the parallels with Donald Trump are so obvious: Donald Trump has managed to figure out this system in which every scandal only makes him more popular because the internet just feeds on attention.

Jaime Rogozinski had an interesting quote in the book. He wrote, “Serious onlookers might feel indignation by what happens on WallStreeBets, but millennials are treating Wall Street for what it is—a huge casino made for them to play in.” Do you think that that perception has lasted about Wall Street—that it is just this system of legalized gambling and guesswork as opposed to sober professional adults doing financial analysis?

It’s a great question. Let’s put it this way: I think a lot of people have gotten drawn in by the way in which the markets feel like a casino or a game. That’s the first thing that had pulled in a lot of the characters in my book and made it seem fun. The markets were not fun before. The markets were not viewed as entertainment before the last few years, and now they have become a source of entertainment.

But then they realize, like, Oh, this is very interesting. When you’re betting on a stock, you’re making these decisions about how the economy works and how companies work. And people dive in, and it becomes this very engaging pursuit in a way that offers a real education. All of a sudden, you’re learning math and you’re learning how interest rates work.

I think the two-sided nature of this is part of what makes it so interesting, and is also very much a part of how the internet works now. I feel like we’ve entered his age of trolling, this form of interaction in which everything is a total joke and very serious at the same time.

And that’s an insane duality to rest upon for a community that’s putting millions and millions of dollars at stake. You don’t know if anyone who’s posting anything is being serious or just or just having a laugh, right?

Yeah, that is what’s so destabilizing about all of this is.

How do you think WallStreetBets changed the culture around short-selling in the industry? Do you think that institutional investors are a little more cautious these days when it comes to taking out short positions because of what happened with GameStop?

Yeah, absolutely. You know, there’s always this joking on WallStreetBets about the losses [they’re incurring] and the fact that they’re degenerates and that they don’t have any real power and that it’s the Wall Street banks that have the real power. One of the ironies of all this is that they have scared the shit out of hedge funds. Hedge funds have totally sort of realized the power of this movement. Wall Street has realized that when you put a stick into this beehive, you are going to get stung—it is going to hurt. Banks and hedge funds have totally backed away from the sort of heavy shorting that used to be common with companies like GameStop and Tesla. They’re very much aware of the power that this new movement has, and they’re very frustrated by it. They’re not necessarily happy about it.

And you talk in the book about how now the institutional investors are actually following a lot of the retail investors trading patterns.

Right. You saw this over the last few weeks with GameStop, where Roaring Kitty, [a Reddit user who made millions during the short squeeze], has come back on social media. It’s been these quant funds and Wall Street investment firms of various sorts that have been most eagerly chasing Roaring Kitty over the last few weeks. Wall Street has realized that they need to honor and follow this. And so that’s given rise to this whole new world of data firms that are tracking retail investors. So they very much realize the power of this young online world.

I think something that this whole GameStop saga really put a point on is [the difficulty] of trying to parse out what makes a company actually promising financially versus what people are just getting behind because they’re just getting behind a company. Is the Wall Street officialdom just now chasing what stocks they think will go up versus what stocks they actually think have good financial footing?

Yeah, I mean, look: Companies still do ultimately rise and fall based on how many widgets they make and how many widgets they sell. The long-term performance of companies is still going to be dependent on the basic financial calculations that Wall Street has always been focused on. But there is now a new element of the equation for the economy and for companies, which is that the way the general public thinks about the company is now very important to even the financial success of that company.

This is most visible in Tesla, where Elon Musk and the cult of personality that he has built up has allowed the company to raise money in a way that then allows the company to spend money to build cars, and get free marketing for those cars, in a way that makes the company succeed and do better than your basic financial calculations would lead you to think. Tesla was the ultimate example of this company that Wall Street hated and that these online crowds loved. And the sort of excitement of the online crowds was a self-actualizing loop, which allowed Tesla to raise money, which allowed them to build factories, which allowed them to sell cars, etc. That process can break down, but there’s this whole new element in finance in the financial world now that Wall Street didn’t see coming.