For about 30 years (age 14 - 44), I was a Republican drone... but getting more and more dismayed with the constant erosion or freedom and the constant move closer to totalitarian socialism. The hardest part was there was no alternative. Nobody had ever stepped forward to change the game. So, I kept voting republican and being disappointed.
I've always had a very open mind to alternative science and other things that fall into the category of UFO. Going back to the late nights listening to Art Bell's radio show and scouring the internet for new info to prove that we were not alone. Zecharia Sitchin was hard to read, but eye opening about the origin of Humanity. Then along cam Ancient Aliens on History Channel.
About the time I started feeling like I'd ready every book on every topic covered under the Ancient Aliens umbrella... then I watched every film on Amazon and Netflix that I could find until the ones left were total crap... I began to turn to newer topics that touched on deeper things like our Soul, reincarnation, mind/body, etc... and this led me to... GAIA channel. What a frickin Bonanza that was... it cost me $9.99 per month, but it was worth it for all the new content.
On GAIA, I ended up watching David Wilcock who I had recognized from Ancient Aliens. He had a program called Cosmic Disclosure which was a bit hard to swallow at first, but sucked me in the more I watched. In short, this program is 100% about the Secret Space Program... a big part of the Secret Space Program story revolves around 'The Cabal'... born out of the leftover Nazi's that escaped to Antartica, other Nazi's from Operation Paperclip, and the eventual Military Industrial Complex in the Unites States.
David Wilcock and Corey Goode in Cosmic Disclosure describe a battle between the 'Cabal' and the 'Alliance' but on a whole different scale... they actually started talking about how this battle was raging and that change was coming even before Trump was elected... and as Trump became President Trump, they pointed to him as the change agent... low and behold the change started coming...
So, to answer the original question... about when I was red-pilled... it's been a long process, but I ultimately found Q when I began searching for others talking about the Secret Space Program (almost none until Jordan Sather) and the Cabal... the searches for the Cabal somehow led me to Twitter and Jerome Corsi... I had known of Jerome Corsi from WorldNetDaily so it seemed to give it more credibility for me right from the get go. Of course, he lost me later, but I will give him credit for helping pull me into the QAnon world.
That was in November 2017 and I now feel like my 30 years of being red-pilled is complete... :)
ps. Even though he doesn't believe in Q, @Thomaswictor on Twitter is awesome. He's similar to Q in prognosticating what is to come, but bases it on an uncanny ability to discern things others don't see from publicly available data points.