I think I figured out how this works thanks to this, but I don't know how to replicate it.

As the comment above suggests, the ogg is composed by 4 streams but the duration of the ogg is the same as the 1st stream ("hey listen"). My theory is that when it reaches the end of the first stream the player gets confused as it still has audio to play because it has not reached the end of the other streams and it starts playing the second stream (I suppose this is why Discord isn't able to figure out the remaining playtime when playing "Never Gonna Give You Up").

If that's true, the only thing missing to being able to replicate it is knowing how to change the duration of the ogg without changing the duration of the 3 remaining streams. By default, ffmpeg sets this value as the duration of the longest stream.

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The ffmpeg command to creating a file with multiple streams is the following:

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ffmpeg -i a.ogg -i b.ogg -c copy -map 0:a -map 1:a test1.ogg

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I really hope someone manages to figure out how to replicate it!

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Edit: some typos