Substack doubles down on uncensored free speech with acquisition of Letter

Substack announced last week that it acquired Letter, a platform that encourages written dialogue and debate. The financials of the deal weren’t disclosed, but this acquisition follows Substack’s recent $65 million raise.

Newsletters are all the rage — Facebook launched its exclusive, celeb-studded Bulletin platform last month, and Twitter acquired the newsletter startup Revue earlier this year. Letter doesn’t publish email newsletters like Substack, but rather, it allows writers to engage in epistolary exchanges about fraught topics like Brexit, dating and the 2020 U.S. Presidential election. The idea behind Letter makes sense. Complicated conversations require nuance, yet these online debates too often happen on platforms like Twitter, where short-form tweets make it harder to have nuanced conversations.

“We could see that Letter, like Substack, was working in opposition to the ad-driven attention economy, attempting to change the rules of engagement for online discourse,” Substack wrote in its acquisition announcement.

But this acquisition may be cause for concern among those already troubled by the controversy Substack faced earlier this year, when news came out that the platform offered some writers up to six-figure advances as part of its Substack Pro program. The perceived problem wasn’t that Substack was incentivizing writers to join the platform, but rather, who Substack had hand-picked to pay an advance. Plus, Substack says that it’s up to the writer to disclose whether they’re part of Substack Pro, which creates a lack of editorial transparency, critics said.

As Substack grew, writers left jobs at BuzzFeed and the New York Times, lured by pay raises and cautious optimism. But as more writers came forward as part of the Substack Pro program, Substack was criticized for subsidizing anti-trans rhetoric, since some of these writers used their newsletters to share such views. Substack admits it’s not entirely apolitical, but the choices of which writers to subsidize, and its decision to use only lightweight moderation tactics, are a political choice in an era of the internet when content moderation has a tangible effect on global politics. Some writers even chose to leave the platform, as a result.

Substack faces backlash over the writers it supports with big advances

Annalee Newitz, a nonbinary writer who since left the platform, wrote on Substack, “Their leadership are deciding what kinds of writing and writers are worthy of financial compensation. [ … ] Substack is taking an editorial stance, paying writers who fit that stance, and refusing to be transparent about who those people are.”

So, when Substack described its new acquisition Letter as a platform that encourages people to “argue in good faith instead of dropping bombs for retweets,” it made the acquisition worthy of a deeper examination. Statements like this sound agreeable, yet this kind of language often appears in arguments that deem social justice a threat to free speech. But free speech shouldn’t mean endorsing hate speech.

Substack wants to position itself as a neutral platform, and for many writers, it’s a valuable way to make money, especially in an unstable journalism industry. But given that some users have already become skeptical of who Substack chooses to financially incentivize, it’s worth examining the implications of buying Letter, a platform that includes writers associated with the so-called intellectual dark web in its group of twenty “featured writers.” On Letter, some of these writers question the validity of childhood transgender identity and refer to the statement “trans women are women” as propaganda, for example. Substack already lost the trust of some trans and gender-nonconforming writers, and the content on its newly acquired Letter won’t help rebuild that trust.

In addition, Letter co-founder Clyde Rathbone wrote in support of a controversial letter published in Harper’s Magazine, which called for the “concerted repudiation of cancel culture.” But critics of the letter point out that free speech isn’t really at stake here.

The open letter had been signed by over 150 prominent writers — like Gloria Steinem, Noam Chomsky (a Letter author) and Malcolm Gladwell (a Bulletin author). It argued: “We need to preserve the possibility of good-faith disagreement without dire professional consequences.” These “professional consequences” echoed the predicament that J.K. Rowling — who also signed the letter — had put herself in. After denying that trans women are women, her reputation suffered. Some might call that “cancel culture,” but others might call it the refusal to continue to platform people who perpetuate harmful beliefs.

“The panic over ‘cancel culture’ is, at its core, a reactionary backlash,” wrote journalist Michael Hobbes. “Conservative elites, threatened by changing social norms and an accelerating generational handover, are attempting to amplify their feelings of aggrievement into a national crisis.”

Substack says it plans to use the acquisition of Letter to help writers collaborate, and that it won’t integrate Letter into its platform. Rather, the Letter team will relocate from Australia to San Francisco to “bring their expertise to help build more of the infrastructure and support.”

TechCrunch asked Substack if the anti-trans content on Letter is cause for concern within the company, given the recent backlash against the platform.

Is Substack really worth $650M?