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Ricky Ashenfelter has an extensive work experience, beginning in 2006 with an internship at Ameriprise Financial. In 2008, they interned at Lincoln Financial Group, and in 2009 they worked as a Senior Associate at ClearCarbon Inc., a Strategic Climate Projects Assistant at the U.S. Environmental Protection Agency, and an MBA Associate at Cambrian Innovation. In 2010, they became a Senior Consultant at Deloitte, and in 2014 they were an MBA Associate at NextEra Energy. From 2015 onwards, Ricky has been the Co-Founder & Chief Executive Officer of Spoiler Alert, a Boston-based enterprise software company.

Ricky Ashenfelter received their Master of Business Administration (M.B.A.) from the MIT Sloan School of Management in 2015, with a focus on Entrepreneurship & Sustainability. Ricky also holds a Bachelor's Degree from Georgetown University in Finance & Environmental Studies. Ashenfelter's educational background is completed with a High School Diploma from Great Valley High School. Ricky has also obtained two additional certifications: a ServSafe Manager from the National Restaurant Association in 2014, and an Open Water Diver from PADI in 2011.