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Cindy Speck started their career in 1995 at Baby Stepps, where they worked as a "When Diamonds Don't Last Forever." In 2011, they joined Maverick Trading as an Options Trader, where they received comprehensive education in trading and learned about fundamental and technical analysis and charting techniques.

Cindy Speck attended the University of St Thomas from 1974 to 1978. During this time, they pursued a Bachelor's degree in Fine Arts and a Bachelor's degree in Psychology, with a focus on Marriage and Family Therapy.