Six years later, who does Patreon serve best? Some 125,000 creators use the service, and according to the data-tracking site Graphtreon, they draw in more than 5 million pledges monthly. One of Patreon's top-earning clients, grossing $139,000 monthly from 31,000 patrons, is the bitingly funny leftist-politics podcast Chapo Trap House, whose cohost, Will Menaker, has praised Patreon's small-­donor model as essential to the show's existence and integrity. (Thanks to Chapo's patrons, no Dollar Shave Club ads need interrupt the socialism.) The most popular musician on Patreon is the extremely online singer­-songwriter Amanda Palmer, who has more than 15,000 patrons and doesn't disclose her earnings.

In predicting whether an artist will succeed on Patreon, Conte says, “the most important thing isn't media or genre or platform—it's how much do you love your fans, and how do they love you back? Are you making a thing that gives people all the feels, and do they just fucking love you?” This is not strictly a matter of artistic merit. “I don't think Björk would do well on Patreon,” he explains. “Arguably, her fans think she makes great art. But does she love her fans, and do they love her back? I don't know.” By and large, he says, Patreon privileges those creators who tend toward higher-­frequency output and whose fans regard them as (mistake them for?) dear friends. “Amanda Palmer loves her fans and they love her,” Conte adds. “They actually feel love for her. That's a particular type of artist. Not every artist wants that vulnerable, close, open relationship with their fans. Like, really tactically: Do you run fan-art contests? Do you respond to comments on Twitter? Do you sell soap—do a weird fun thing with your fans then send them a thing in the mail, thanking them for what they contributed?” If not, don't count on making your rent via Patreon.

In many ways, Conte is still figuring out how to transform from Pomplamoose Jack into CEO Jack. This process has involved “three executive coaches” and all kinds of growing pains that correspond, roughly, to Patreon's own evolution as a global audience-management service. These days, the range of people who want to cultivate audiences on Patreon extends far beyond bedroom musicians. They also include more controversial and ideologically charged creators, like the makers of a new Jeffrey Epstein-focused podcast called TrueAnon (2,600 patrons contributing $11,000 a month to support the hosts “in capturing the pedo elites”) or the right-wing online magazine Quillette (2,100 patrons contributing $15,000 monthly). Which means that the basic question he once invoked as the company's true north—“What would Jack Conte want out of this platform?”—has grown less useful.

It also means that Patreon has faced many of the same content moderation dilemmas that have vexed much larger platforms like YouTube and Facebook. The company's system for reporting abuse, for example, has at times become a shooting gallery for online agitators seeking to defund their political enemies. Within the span of a week in 2017, Patreon shut down the accounts of both a far-right Canadian YouTuber named Lauren Southern and an anarchist news site called It's Going Down; both had been the targets of coordinated campaigns flagging them for violations of Patreon's community guidelines.

Predictably, Conte's attempts to run a neutral platform have pleased no one. People on the left accused Patreon of shuttering It's Going Down just for the sake of balance, to appease trolls on the right. And last December, after Patreon booted another right-wing account for violating community guidelines against hate speech, prominent right-leaning figures like Jordan Peterson and Sam Harris left the platform in protest of its supposed left-leaning political bias. “It's not a matter of politics for me, to be super clear,” says Conte, who was vocal on Twitter during 2016 in his distaste for Donald Trump. “We've taken down ultra-left groups for the same reasons as ultra-right.” All communities set rules, he says. “The difference is scale. When your community is 2 billion people, and your decisions affect the global consciousness, these decisions shouldn't feel arbitrary.” A funny riff on a toy piano, this is not.

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Conte has also struggled to avoid alienating his core users as he chases new revenue and brings his platform up to scale. In March—partially in response to Facebook's launch of a distinctly ­Patreon-ish product called Fan Subscriptions—Patreon announced that it was scrapping its longtime policy of collecting a flat 5 percent of the income creators got from their patrons. Now, in addition to a bare-bones Lite plan at 5 percent, it would restrict certain features and services to creators willing to pay for Pro and Premium accounts, topping out at a 12 percent take. In response to this fee hike, a popular YouTuber named Dan Olson posted a thread on Twitter arguing that the greed of the company's venture capital backers had finally kicked in: “Investors who demand geometric growth are about to demand Patreon eat itself.” The thread went viral. When I mention it, Conte takes several minutes to list some of the operating costs that Patreon must increase revenue to meet. “I get pressure from VCs, but I get more pressure from creators,” he says. “Creators get furious when we don't do what they want.” (Facebook's Fan Subscriptions service, for its part, takes as much as 30 percent.)