I'm intentionally value-agnostic about whatever makes Colin happy in the post. As long as operating businesses suboptimally is not in fact his terminal value, there exists a transition between Tarsnap and Tarsnap' which makes him
even happier. Everybody wins, especially Colin, which strikes me as a happy outcome because I like seeing when geeks are suitably rewarded for creating substantial improvements to the world, which Colin has done.
If running Tarsnap as a free public utility is the light he wants to bring to the world, the outlined Tarsnap' is better at that than his Tarsnap is. Charge businesses more, invest in better UX, subsidize non-business users straight to "free." If he wants to lay on a beach sipping iced cocoa, this is more beach and more cocoa. If he wants more time with his family and less time in the inbox, this is a trivial modification away from that. ("Make money, buy your way out of inbox.")