Reddit’s users love to complain about Reddit. They also love to use it.

This week marks the deadline for the company’s most loyal posters and moderators to preregister for the chance to buy shares in Reddit’s impending initial public offering, before they start trading on the open market. There will be space for about 75,000 users, according to a person familiar with the matter. The move is intended to give the people who moderate Reddit’s forums and write its content for free the chance to reap some financial rewards.

So far, the reaction on the platform has been skeptical. The site’s r/WallStreetBets forum has threatened to bet against the stock, with many people noting that the company still loses money two decades into its existence. (Reddit lost US$90.8 million last year, down from $158.6 million the year before.) Some have complained that the invitation to invest fails to make up for the unpaid labor they’ve invested making the site work. The complaints echo another fight last year, when many forums protested Reddit’s decision to raise prices for access to its data, complaining that the move made it too expensive to build apps for the platform.

But while Reddit’s users may not always like it, the number of people on the site continues to grow. That will be one of the key factors investors focus on when the company stages its long-awaited IPO. Daily active unique users grew 27 per cent in the final quarter of 2023, the most of any of the last seven quarters. The platform had 267.5 million weekly active users in the last quarter (the viral chatbot ChatGPT by comparison has about 100 million). And according to Similarweb data, Reddit is one of the 10 most-visited websites in the US.

Reddit is “a unique asset and a very popular portion of the internet community,” said Matthew Kennedy, senior strategist at the IPO research firm Renaissance Capital. “I don’t think they’re going away. There are reliable users.” Kennedy noted Reddit’s stocks forum was mostly bearish on the company’s IPO: “I think users accurately see that this is not likely to have a huge pop.” But with this stock, he added, anything could happen.

The company’s IPO plans have been in limbo for more than two years as the tech startup world stumbled. Now, Reddit is set to be the first high-profile tech offering of the year, potentially setting the stage for a larger rush to go public. Led by co-founder Steve Huffman, the social media giant could be valued at as much as $6.5 billion. After a halting path toward IPO, that the company is going public at all is a testament to its durable cultural power.

Every social media site — X,  Facebook and TikTok to name a few — has to contend with hard-to-please users, but Reddit’s plight is unique. Its users are fiercely loyal, and they can be singularly combative. They have launched revolts over everything from racism on the platform to executives’ staffing decisions. Some users post toxic content, forcing the company into difficult moderation debates. And as a group, Redditors have wielded considerable power over the world at large, often in unpredictable ways.

Most famously, in 2021 the platform’s WallStreetBets forum ignited a meme-stock frenzy, propelling skyward the stocks of nostalgic but struggling companies like GameStop Corp. and AMC Entertainment Holdings Inc. and sending shockwaves through the financial industry. The saga inspired the movie “Dumb Money,” released in 2023.  When it goes public, the platform that invented meme stocks runs the risk of becoming one itself.

Reddit noted the possibility as a risk in its IPO filing. “Given the broad awareness and brand recognition of Reddit, including as a result of the popularity of r/wallstreetbets among retail investors,” the company warned that its stock could “experience extreme volatility … which could cause you to lose all or part of your investment if you are unable to sell your shares at or above the initial offering price.”

Users on WallStreetBets got a kick out of the fact that the company listed the forum as a risk factor, posting about it with a sly smiling emoji. The company declined to comment for this story.

Despite the risks posed by retail investors — particularly the ones on Reddit — the company has made giving shares to its users a central part of the story around its market debut. Starting Feb. 22, when the company filed its paperwork, Reddit began sending invitations to power users who would be eligible to pre-register to participate in the IPO. The first batch included unpaid moderators who participate in community programs, which are Reddit’s efforts to have moderators collaborate with company employees on efforts such as beta testing new tools, features and policy changes.

“Our users have a deep sense of ownership over the communities they create on Reddit,” CEO Huffman said in the company’s filing. “We want this sense of ownership to be reflected in real ownership — for our users to be our owners. Becoming a public company makes this possible.”

Reddit’s public listing was never a certainty. In 2005, the company was among the very first batch of companies at Y Combinator, the most famous startup accelerator. More than two dozen YC companies have since beaten Reddit to the public markets.

“Having seen a lot of startups and invested in a lot of startups, I’ve never seen such a winding path,” said Jessica Livingston, co-founder of Y Combinator. Reddit “survived so much because the users love it.”

Reddit’s circuitous route to IPO included a 2006 acquisition by New Yorker-owner Conde Nast. It spun off again in 2011. Reddit then cycled through a number of other CEOs in quick succession. These included Sam Altman, for the span of just days. He was succeeded by Ellen Pao, a former venture capitalist at Kleiner Perkins, who was the subject of racist memes posted on the site. Huffman, Reddit’s current CEO, left after the acquisition and returned to helm the company in 2015.

When Pao left as interim CEO, she wrote, “I have just endured one of the largest trolling attacks in history.” Pao’s harassment on the very platform she ran showcased a dark side of the company — and an issue that remains a risk ahead of the IPO. For years, Reddit, which relies on unpaid moderators to tame its forums, has been criticized for harboring hateful content. The company introduced a hate speech policy in 2020 and has internal teams dedicated to safety.

Despite the challenges, the company still sees its user base as a wellspring of future revenue. In its filing to go public, the company said it’s “in the early stages of monetizing our user base,” and that it’s “still scaling our advertising revenue model,” which accounts for the bulk of its sales.

How its users will react to the monetization is an open question. Once the company finally goes public, Reddit will have lots of reasons to try to keep them happy.

“Reddit is one of the internet’s largest corpuses of authentic and constantly updated human-generated experience,” the company said in the filing, adding that it would like to ensure that the company’s actions “do not conflict with our values and the rights of Redditors.”