Although best known as one of the primary members of Achievement Hunter, appearing in numerous Let's Plays and videos, Ryan previously worked in the studio with Monty Oum, Lindsay Jones, and Kerry Shawcross.
He is also known for his regular appearances on the Rooster Teeth gaming podcast, The Patch, as well as a prominent role in the live-action production Ten Little Roosters. He co-hosted Free Play alongside Meg Turney. Additionally, he voices Lieutenant Smith in Red vs. Blue and the Mad King in X-Ray and Vav. The latter character is one of five in the superhero show to be voiced by their creator; two of the other four are the titular duo, voiced by Ray Narvaez Jr. and Gavin Free respectively.
As of October 6th, 2020, Ryan no longer works for Rooster Teeth  due to multiple allegations of sexual misconduct.
- Ryan was hired by Rooster Teeth co-founder Geoff Ramsey through a Craigslist ad.
- In "The Badge and The Burden", Ryan's character, Professor Port, keeps a Boarbatusk captive; fans have likened this to Ryan keeping a cow named Edgar trapped in a hole under his house in the Achievement Hunter Minecraft Let's Plays. However, according to Kerry and Miles Luna, this was coincidental, the episode having been written months before the first appearance of Edgar.
- A likeness of Ryan appears in RWBY as part of the fictional group The Achieve Men, a poster for which hangs in Team RWBY's dorm room.