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Ryan O'Leary's work experience includes serving as Director of Operations at TC Restaurant Group starting in March 2023. Prior to that, they were the General Manager at Luke's 32 Bridge from April 2022 to March 2023 and at FGL House from April 2021 to May 2022. Ryan also worked as the General Manager at Backyard Kitchen & Tap from July 2018 to February 2021. Before that, they were a General Partner at Double Deuce/Whiskey Ranch Entertainment LLC from July 2008 to January 2020. Ryan also served as the General Manager at Volcano Rabbit/RMD Group from December 2016 to July 2018. Their earliest experience was as a Multi-Unit General Manager at Fred's Mexican Cafe & Moose McGillycuddy's from April 2001 to September 2008.

Ryan O'Leary holds a Bachelor's degree in Business Administration and Management, General from the University of Northern Colorado. No specific start or end years were provided for this educational experience.