Weisman graduated from Francis W. Parker High School, in Chicago, Illinois. 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. After starting out producing supplements for the pen and paper role-playing game Traveller. FASA later produced the successful BattleTech and Shadowrun franchises.
With funding from FASA and from a Japanese investor, Jordan founded Environmental Simulations Project — later renamed Virtual Worlds Entertainment — in 1990, the company that produced the BattleTech Centers. Working with Incredible Technologies, VWE created the world's first immersive networked location-based virtual reality gaming centers. VWE was a critical, though not a commercial success.
In 1995, Weisman founded FASA Interactive to personally take over the development and production of the hit MechWarrior PC games. The franchise is one of the top-selling PC games of all time, with sales of over 9 million units worldwide. In 1999, Microsoft acquired FASA Interactive and moved the 40-person development team to Redmond, Washington. As part of the deal Weisman became Creative Director for Microsoft's entertainment division.
In 2000, he founded WizKids, which produced the games Mage Knight, Heroclix, and Pirates of the Spanish Main. WizKids grew rapidly and went from start-up to over $30M in annual sales in just two years. The company focused on miniature figure games that use a combat dial (also invented by Weisman) and are easy to learn for younger players. WizKids was sold to Topps in 2004.
In 2003 he founded 42 Entertainment, a design company in the new field of the alternate reality game or ARG's. 42 has created multiple ARG's, including, "I Love Bees" to promote the Xbox game Halo 2, and "Year Zero" to promote the Nine Inch Nails album of the same name.
In 2007 Weisman founded Smith & Tinker (named after the characters in The Wizard of Oz). Smith & Tinker has licensed the electronic entertainment rights to Crimson Skies, Shadowrun, MechWarrior and other FASA properties that had belonged to Microsoft.
The same year Weisman co-founded the start-up Fyreball with Pete Parsons (formally of Bungie Studios and currently serves on the Board of Advisors along with Ed Fries). The company is now operating under the name Meteor Solutions
On May 27, 2009 Weisman's Smith & Tinker announced their first game had been released to public beta. Nanovor is an online battle game targeted to 7 - 12 year olds. In support of the game, Smith & Tinker is releasing episodic cartoons, graphic novels, comic books, figurines and more.
On June 9, 2009 Weisman and J.C. Hutchins released Personal Effects: Dark Art (Griffin). On the same day Weisman along with Russ Bullock announced that the MechWarrior franchise would be seeing a relaunch.
Jordan is currently an Adjunct Professor in the Interactive Media Division at the USC School of Cinema-Television. In 2012 he started to raise money, through Kickstarter, for Shadowrun Returns, a new video game adaptation of Shadowrun.
Design credits 
Weisman's design credits in paper RPG game design include:
- Aerotech 2, Revised Ed. (BattleTech) (2004)
- MechWarrior: Dark Age (2002)
- Earthdawn (1993)
- Shadowrun (1989)
- MechWarrior: The Battletech Role Playing Game (1986)
- Star Trek III: Starship Combat Game Box Set (1984)
He also served as production manager and/or graphic designer on a long series of titles, and is co-author with Sean Stewart of Cathy's Book, a young-adult novel with ARG components.
- "The intricate plot behind 'A.I.' Web mystery". USA Today. 2001-06-28. Retrieved 2010-05-07.
- "Smith & Tinker is pleased to announce that it has licensed from Microsoft the electronic entertainment rights for Mr. Weisman's previous creations...". 2007-10-15. Archived from the original on 2007-12-13. Retrieved 2008-02-07.
- "Connect, Collect & Battle with Nanovor". 2009-05-27.
- "MechWarrior Q&A - The First Details". 2009-07-09.
- "Not Your Father’s MechWarrior". 2001-09-11.
- "Shadowrun Returns". 2012-04-04.
- Smith & Tinker
- Weisman's rap sheet at MobyGames
- Escapist Magazine's biography/article on Weisman
- John Cook's Venture Blog at SeattlePI.com