I think of this moment probably once a month and I don’t know how to make it stop.

Hmmm, I have been skeptical of AI, but it looks like it’s getting smarter.

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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

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.

Is it just me, or is this graph (first graph in the article) completely unintelligible?

The X-axis being time is self-explanatory, but the Y-axis is somehow exponential time but then also mapping random milestones of performance, meaning those milestones are hard-linked to that time-based Y-axis? What?

Yes, but it’s legitimately different when you are a huge company versus a struggling artist. A company like Nintendo has the capital and staying power already to reap generational rewards from embedding their IP into a culture.

I’m in the same boat. The only reason I’m considering getting a Switch 2 now is because the first gen consoles always end up the easiest to hack.

Don’t worry, I’m sure the FTC will investigate this obvious and pernicious false labeling bait-and-switch scheme!

I switched to Rust Desk after I got repeatedly flagged for commercial use of Team Viewer and access disabled. I was doing nothing of the sort, but it happened after I accessed my personal computer on my personal phone while at work. They must have IP address checks that are extremely aggressive.

I followed their process to “verify” I was non-commercial, which was invasive and insulting, and then was flagged again.

Rust Desk works great, no problems, never using Team Viewer again.

I’m like, “Is this what normal people in 2025 watch?” I feel like an alien on earth, except the planet changed and not me.

Tried this on a private window, and yes, that’s what it looks like. Thought I’d click on Shorts and let the first 3 seconds of the opening auto-play video play. Then back to the home page and wow, full of absolute trash.

All very good points.

He keeps trying. He seems to think that can be done by just putting his thumb on the system prompt, and then we end up with obvious nonsense like that South African white genocide preoccupation. It’s fortunate the Musk isn’t smart enough to figure out how to do it subtly.

The article says an iOS app was released to testers.

Guess I’m an outlier. For me, games were the way to disconnect from the stress of relationships. I’ve been an introvert since the beginning, and so games’ positive associations for me are a safe place away from social pressures.

I also imagine every “retro” generation thinks its games are the best. Like, there was a meme post about joy at finding a PS2 torrent recently with strong implied nostalgia, and that’s ok. People usually experience video games at an age where the games teach them archetypical feelings of intellectual pleasure, the first time they experienced joy at solving complex problems for example. That becomes a core association through life.

So I think we’ll all have strong feelings linking the systems we played at our formative years. And again, that’s ok. That we can form such strong associations is an expression of the basic human value of video games, as an art and modern cultural necessity.

Yup, the entire culture of Google has nearly changed. It used to be coder- and innovation-driven, and open-source was a natural thing to support. Make more money by growing the pie, creating markets with new tech.

Now it seems it’s middle managers and MBAs calling the shots, and their strategy is generic business zero-sum mindset - lock down, restrict, extract. They still see the PR value in open-source, but that’s it.

Just becoming 1990s Microsoft or 1980s IBM.

This looks like Microsoft committed exactly one toe to testing the water.

Tip in case I’m not the only one: If the captcha isn’t working in the app, log in via a browser and turn off ad blockers to check out.

Ah, the grand circle of enshittification.