Beginning his career at DWANGO as Vice President of Development before being hired to lead marketing and publishing at id Software in 1995, Wilson has subsequently co-founded multiple independent video game publishers, including Gathering of Developers, Gamecock Media Group, Devolver Digital, Good Shepherd Entertainment, and DeepWell DTx.
In 2019, he called on the industry to start grappling with the reality of video game addiction and begin taking active measures to curb its effects through "being more intentional about the content we create.
[8] He also currently sits on the advisory board of Take This, a non-profit dedicated to raising awareness about mental health issues for video game professionals within the industry.
[14] Wilson began his career in his early 20s as Vice President of Development for DWANGO, an early online gaming service based in the United States, which pioneered the use of a nationwide network of dial-up servers to host multiplayer sessions of Doom, Quake, Duke Nukem 3D, Shadow Warrior, and Heretic, and other popular video game titles.
[15] Following the platform's explosion in popularity, Wilson left DWANGO in 1995 to join Doom developer id Software to bolster the company's first forays into game publishing.
Wilson left id Software at the beginning of 1997[17] to join John Romero and Tom Hall for the launch of the game development company, Ion Storm.
[21][better source needed] Wilson has continued to produce multiple feature-length and short-form film projects via Gone Off Deep in recent years, including 2011's Austin High [22] and 2016's Stand Up Empire.
After the release of Serious Sam 3: BFE in 2011, Devolver decided to shift its focus from larger development cycles to the emerging indie gaming scene.
[26] Since 2017, Devolver has released more than 50 new game titles, including Hotline Miami 2: Wrong Number, Gris, Reigns, My Friend Pedro, and multiple installments of the acclaimed Enter the Gungeon and Shadow Warrior franchises.
In 2020, Devolver announced its first television project with an adaptation of My Friend Pedro, to be written and executive produced by John Wick creator Derek Kolstad.
[34] Their catalog includes the Transport Fever series, Semblance, Phantom Doctrine, and Where the Water Tastes Like Wine, which features voiceover work by Grammy Award-winning musician Sting.
In March 2018, Wilson was appointed to the board of Take This, a Washington-based non-profit organization founded in 2013 by video game journalists Russ Pitts and Susan Arendt and clinical psychologist Dr. Mark Kline.
Founded in 2023 by Wilson, and backed by Nanea Reeves and Terry Gross, the company's primary aim is to show users "how to use media more mindfully.