I couldn't attend, so thank you for posting the transcript on your site. It wasn't what I thought. From the title, I thought maybe by 'weirdness' you meant some of the silly (or even snarky) comments in code and odd little jokes and easter eggs in the UI like the games built-in to Emacs.
It seems that when you say weirdness, I should interpret it as an attitude of aloofness, causing an unwelcoming or even hostile culture to those who are on the outside. We are too attached to being underdogs; addicted to a life is quieter in the margins. We secretly enjoy holding the keys to esoteric knowledge and revel in our assumptions that, when we see some upper executive using Windows, we are superior to our superiors. We say they should all try Linux and LibreOffice, but don't really want that because it would put us and them on the same level. This is the wrong attitude. This is not how we bring nobler ideas to the world. Of course, no-one admits to thinking like this -- these things creep into our consciousness when we aren't paying attention.
We need to let go of every notion of "Us and Them", but to do that we also need to let go of the desire to feel superior and the fear of losing. This isn't meant to be a secret society; this is not what secret societies do. Even the Masons aren't secret anymore. Time to let go; this baby is grown. Trust that the open-source movement is strong enough to survive the greedy paws of business and non-tech users, and maybe it will bring some enlightenment to a world ruled by money.
You can say "Hello World" in any language,
it's the open-source world that says, "Hello, you!"