The company was founded in 1996 by 23-year-old university student David Manga, originally with the sole purpose of publishing and distributing a single board game called All Canadian Trivia.

With nearly 50% of its annual revenue in bad debt and unrecoverable, Outset Media was bailed out with angel investments from family members and financing from the Royal Bank of Canada.

In 2003, Outset Media made its first appearance on the Profit magazine's annual ranking of Canada's Fastest-Growing Companies.

Cobble Hill puzzles are used as props for the retail store and are widely seen in the Theatrical release poster, as well as throughout the Official Movie Trailer.

[8] Outset Media has developed distribution partnerships with several European and American game and puzzle companies, including MindWare, Patch Products (now PlayMonster),[9] Fat Brain Toys, Royal & Langnickel, Late for the Sky, SmartLab Toys, Pressman Toy Corporation, Goliath Games, Popular Playthings, Cheatwell Games, Maranda, Monkey Business Sports, Cobble Hill Puzzles, and D-Toys Puzzles.