He graduated from Lakeview High School and Richland Community College and attended Millikin University.
When Bledsaw was laid off from his job at General Electric in 1975, he decided to form a company to create supplements for Doctorate&Doctorate players, and with Bill Owen he went to seek permission from TSR. Bledsaw and Owen showed their City-State material to Dave Arneson, Gary Gygax, and other TSR staff, who told them they could publish supplements to Doctorate&Doctorate if they wanted to With this casual licensing agreement, they created a large map of Bledsaw"s City-State, first selling copies of the map and subscriptions to Judges Guild"s bimonthly play aids publication. Bledsaw and Owen became full-time employees of Judges Guild in 1977.
Owen was also working full time for his family business, so he left Judges Guild in the fall of 1977 and sold his shares to Bledsaw.
By spring of 1978, Judges Guild left Bledsaw"s living room and moved to a real office. In 1978 Bledsaw sent Gary Gygax hundreds of pages of notes about campaigns, some of which was incorporated into the original Dungeon Masters Guide as appendices.
When TSR started publishing their own adventures in 1978 beginning with the G-series, the Doctorate-series, and Tomb of Horrors, Bledsaw felt this was in violation of TSR"s previous agreement with Judges Guild. By 1985, Judges Guild had stopped publishing new material after several distributors and retailers went out of business owing Judges guild money.
Early in 1999, Judges Guild - led by Bob Bledsaw - returned on the internet at judgesguild.com, and began selling original Judges Guild products which had been warehoused for 15 years, and also started taking new subscriptions for Pegasus magazine.
Bledsaw and James Mishler formed a new company called Adventure Games Publishing. Bob Bledsaw died on April 19, 2008, from cancer. Bob Bledsaw, Junior., took over Judges Guild, which published Lost Manitoba"s Trail (2010) as Bob Bledsaw"s final contribution to the world of the Wilderlands.