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Ryan Penneys has a work experience which includes roles at One William Street Capital, Starwood Property Trust, and LNR Property LLC. At One William Street Capital, they started as a Vice President in October 2016 and later became a Senior Vice President in January 2022. At Starwood Property Trust, they were a Senior Analyst from July 2014 to February 2016 and an Associate from March 2016 to October 2016. At LNR Property LLC, they worked as an Analyst from January 2012 to June 2014.

Ryan Penneys attended Ransom Everglades School, but it is unclear what degree or field of study they pursued. Later, Ryan Penneys enrolled in Washington University in St. Louis and completed a Bachelor of Science in Business Administration with a focus on Finance, General. The specific start and end years for both educational experiences are not provided.