It was at Compound Media. Ryan was kind of a "wack packer" for Pat Dixon's New York City Crime Report, where he started off doing joke reporting as "Asian Pat Dixon" and would literally just do a perfect impression of Pat Dixon but he was Asian. He would do other random impressions and stuff, those shows had a lot of fan and guest contributions, but he seemed to have a history and friendship with Dixon, probably from hanging out at Comedy Clubs and whatnot.

He also seems to be a part of the whole Opie & Anthony NYC comedy fan scene, but I had never seen him before on Compound Media until he was immediately in the first few episodes of the Crime Report. After that, I'd see him on a bunch of other shows in the audience or contributing randomly, and I imagine hanging out around the shows lead him to join the Proud Boys with other fans, and I do recall him sporting Proud Boy gear early on in their formation.

Eventually, he put on a fake beard and guest hosted as "Asian Gavin McInnes" on Gavin's show when Gavin was away on vacation and had a bunch of guest hosts for a week, including the infamous Mike David from Red Bar which started a whole shitshow of drama later on; Ryan actually called into that show pretending to be Bill Burr.

TL;DR Ryan was a Pat Dixon/Compound Media groupie who joined Proud Boys early on and got to know Gavin there. His admittedly impressive impression skills are the only thing that separated him from other weird hanger-ons.