I don't think the article accurately represents anarchism / Marlinspike's philosophy.

The article seems to be trying to say that anarchist values are the root of Signal, but this is a barrier to pragmatism or general adoption.

It describes anarchism, or, the principles of it that Marlinspike adopted (which aren't inherently anarchist. Though Marlinspike is of course an anarchist), as "far out on the political fringe." It says explicitly "sticking to anarchism would imply an almost certain defeat." It implies Marlinspike agrees by dropping his quote on anarchist failure.

However, in the quoted article from Marlinspike, he absolutely doesn't imply something being anarchist relegates it to failure. From his article https://moxie.org/stories/promise-defeat/

> Anarchists are best known for their failures... And yet, far from trying to suppress these histories, these are the stories that anarchists recount. ... This is unusual. American Patriots do not speak, with a gleam in their eyes, of the incredible number of battles that George Washington lost (and he lost almost as much as anarchists do). ... The difference between the ways Nationalists and Anarchists talk about their histories seems critical.

> Will there ever be a night — one glorious evening — when the world is won? Where suddenly civilization, the spectacle, class, racism, and patriarchy all simultaneously topple and remain in ruins? ... It seems unlikely to happen in one moment. ... The George Washingtons of the world offer success. This is based on "realism" and the logic of quantifiability, where it is necessary to make compromises, pass laws, and assert control. Because these are the things that can be won; this is where success is found.

> Anarchy, by contrast, offers us defeat. ... Anarchists are such failures because, really, there can be no victory. Our desires are always changing with the the context of our conditions and our surroundings. What we gain is what we manage to tease out of the conflicts between what we want and where we are. ... Remember that success is a word used to measure. It describes dollars made, people counted, votes cast. In other words, it's a swindle. The rejection of quantification, the emphasis on the role of the individual, is what makes anarchism unique.

By my interpretation, the article is pulling a George Washington, trying to quantify the success of anarchism-in-software, or perhaps private communication, to whether signal can "go mainstream."

> For an idealistic engineer to succeed, he will have to build something that is useful to many.... Signal’s success depends on maintaining its principled anarchist commitments while finding a wide-ranging appeal to the masses

No, Signal is already successful, it's probably already achieved Marlinspike's goal of actualizing a "normal" way to do end to end encrypted private communication (and made it easy for his friends to do so), and it's absolutely achieved the general philosophical goal, through the popularity of the protocol, of giving people the chance to be in control of their surroundings.

If Signal "fails," I guess by not growing its userbase more, the anarchist solution is to build again for whatever the new context is. The Win is there, we'd have the memories of Signal, it existed and let us maintain control of our surroundings if even only briefly.

Example:

> Signal also doesn’t do a good job serving some of its core users. Activists and organizers deal with huge amounts of messages that involve many people and threads, but Signal’s interface lacks ways to organize all this information.

The solution is build again. Or, squat. If people can find a way to make Slack work to organize an antifascist protest, even if it means trading end to end encryption, then, that's a win.