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I don’t know about progressive, but he’s definitely something.

Here’s his last in-person RailsConf keynote: https://youtu.be/VBwWbFpkltg

He’s promoting anarcho-communism in a RailsConf keynote.

Odds are if the conference told him to keep it on topic... he would decline to show up ever again!

Now imagine he was offered 6 months pay to not show up ever again!