He went to the Merchant Marine Academy and briefly attended University of Illinois at Chicago, before leaving school to pursue his business interests.

In 1980, Weisman founded role playing game publisher FASA Corporation (short for the Freedonia Aeronautics & Space Administration, named after the fictional country in the Marx Brothers film Duck Soup) with partner L. Ross Babcock.

[1]: 119  FASA agreed in August 1981 to publish the magazine High Passage, with Weisman and Babcock responsible for the layout and editing.

[1]: 120  FASA published a game involving battling mechanoids called Combots (1983), by Weisman and Fawcett.

[1]: 122  Working with Incredible Technologies, VWE created the world's first immersive networked location-based virtual reality gaming centers.

[1]: 128  Smith & Tinker licensed the electronic entertainment rights to Crimson Skies, Shadowrun, MechWarrior and other FASA properties that had belonged to Microsoft.

[5] The same year Weisman co-founded the start-up Fyreball with Pete Parsons (formerly of Bungie and currently serves on the Board of Advisors along with Ed Fries).

[citation needed] On June 9, 2009 Weisman and J.C. Hutchins released Personal Effects: Dark Art (Griffin).

[12] Shortly after, on September 10, 2013, Jordan's company launched a Kickstarter for its first tabletop game, Golem Arcana.

[citation needed] In June 2018, it was announced and completed Harebrained's acquisition by Paradox Interactive for a fixed purchase price of US$7,500,000.

[16][17] Weisman has won more than 100 awards, including election to the Hall of Fame by the Academy of Adventure Gaming Arts & Design.