

That’s some quality conspiracy thinking!
But there are too many people who could have been early adopters and have any number of random motives for this to be “likely.”
Heck, I was watching Bitcoin when it was like $0.002 a coin and someone spent 10,000 (presumably home-CPU-mined) BTC to buy a pizza. There were a ton of people there at the beginning, the barrier to purchasing a ton was very low, and unlike me, a lot of them certainly had $20,000 to spare and believed in it enough to buy.
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:
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