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 all credibility here because they doesn’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/justified/rationalized (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.