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This one is a fun part. He talks about an old, defunct BBS - Communitree (tried to find a trace of it but there's some other stuff now with this name) - which core idea was freedom of speech. Well, liek imageboards, no? But some users wasn't interested in "adult conversation" but in "fart jokes" and obscenity. And they flooded the BBS with their inane bs. So in the end the message board was killed off by its administration. It was shut down by people logging in and posting, which is what the system was designed to allow.
Then he goes to other examples and related ramblings to turn back to the structures: groups need rules, and rules about making rules, constitution, a baseline they can orient themselves. He really can't wrap his head around a place which is unmoderated.
And to be honest he is kinda right in that. Even imageboards have some rudimentary moderation. Maybe those which only run on onion service can ignore this, but on the clearnet it's not that simple. However compared to an average forum IB moderation tend to be very lax - no matter how much some users complain (the usual pitfall here is consistent moderation, and oftentimes it's hard to draw a clear line what is allowed and what isn't). And imageboard discussion tends to be all over the place, if it's flame war then it is. On the other hand chans rarely have a goal which the users should work towards.