I saw the Wikileaks stuff very early on (Assange spoke at the 2010 Oslo Freedom Forum so was paying attention) but didn't explore it more deeply until 2013 when I went to Ephemerisle and met folks very passionate about Bitcoin. One of them got us involved with a Bitcoin fundraiser for Ukrainian activists. I was still a bit skeptical though and didn't fully grok what was happening until 2017-2018.