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Joined 2 years ago
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Cake day: June 22nd, 2023

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  • Yeah, this post started as a reassurance that Tailscale wouldn’t enshittify. But it turned out to just be an argument about how to avoid enshittification that boiled down to two principles:

    1. You shouldn’t make your product worse because it’ll eventually harm the company; and
    2. Founders are magic and need to never turn over control of the company to others (be it new CEOs or VC) to resist enshittification.

    Both are partially right and partially wrong.

    For #1: Yes, making your product worse eventually harms the company. No, you can’t expect CEOs to accept that as a reason to not make their product worse because even if it harms the company, short-term incentives that lead to enshittification are eventually going to become irresistible. His comment about reaching “zen” with leveled growth and profit will never stop VCs from calling in demands and favors.

    For #2: Yes, founders typically “get it” more than their VC- or failure-initiated replacements. No, that doesn’t mean founders are uniquely resistant to enshittification. This is your point too, and it’s why I don’t believe this person - they lose credibility here because they don’t acknowledge they aren’t special. Every tech bro out there thinks they’ve cracked the code to permanent tech hegemony. That exceptionalist thinking turns into enshittification, since the product-worsening or overcharging is easier to justify as temporary/necessary/not-a-big-deal (until it isn’t).

    And all of this doesn’t explain why Tailscale specifically gets immunity if the principles are true.

    So interesting post, and a lot more self-awareness than most founders which is still a little reassuring, but a lot of warning signs too.

    Edit: clarity







  • Sometimes I do it for comments, and it’s just because I don’t really like what I wrote. I read it and it’s just banal, and I’m like, “you’re not moving the discourse forward at all.”

    What annoys me are people who did that to thousands of their posts after leaving Reddit. They’re their posts, they have the right to do it, but I’m like, c’mon, Reddit isn’t suffering from it. They’re selling the data for the same price with or without, and they have all the backups. No, all the users who are googling a one-place-on-the-Internet solution to their extremely specific problem are suffering.

    I think that’s like getting angry at your boss and taking it out on your family.