Olson was host of WAUK 540 ESPN's "The D-List," which aired weekdays from 10AM-1PM and featured Dan Needles, the longtime Sports Director at WISN-TV.
Olson was also a frequent contributor on the Bob and Brian morning show on WHQG The Hog to discuss Milwaukee Brewers baseball.
Pulled out of the intramural ranks to be the 10th man on a 10-man squad, Olson was rewarded with varsity letter for his efforts even though he barely played for the Panthers and did not score a basket.
After appearing on multiple radio outlets as a Brewers/baseball expert, Olson teamed with Needles on a Saturday morning show in the summer of 2004 and kicked off "The D-List" on Jan. 3, 2005.
When the show began, Needles' participation was limited by WISN-TV management and Olson worked with a variety of co-hosts including local broadcasters like Bob Brainerd, Daron Sutton and others.
The show, which airs before ABC's primetime college football broadcast, is a breezy 30-minute affair that analyzes the next day's Green Bay Packers game and features a "Stump Rainman" trivia segment, debate and coverage of other sports.