IMHO they should be a good steward and toss the Wireguard guy a mil considering Tailscale is pretty much Wireguard with a GUI on top.
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It’s a bit like saying Dropbox is just a GUI on top of TLS.
Well, it is. After all, for a Linux user, you can already build such a system yourself quite trivially...
https://hn.algolia.com/?dateRange=all&page=0&prefix=false&qu...
That said, I don't really understand the supposed misunderstanding you point out. It seems that dang argues that "the exchange was pleasant and successful." I've never seen someone claim otherwise.
Rather, I've seen it used as an example of how technical users can fail to recognize the complexity inherent in their workflows, and therefore may also fail to see the real-world business value in creating (and selling) simpler interfaces. See also a SMOP: https://en.wikipedia.org/wiki/Small_matter_of_programming