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Ben and Jacob met in Calculus class in 10th grade, and tried founding a startup in high school — it didn’t go anywhere. During high school, Ben lead the frontend team for the World Health Organization’s COVID-19 App Team. After high school, Jacob went to Apple and Ben went to college. When there was an opening on his team, Jacob had Ben apply, and Ben left UChicago to go work at Apple. They spent about 2 years at Apple as Senior Engineers in the Conversational Engineering Department, before leaving to found Freestyle. Freestyle is directly inspired by what they saw as their failures of the tech they worked with at Apple.