Freestyle

Freestyle's founders, Ben and Jacob, first crossed paths in their 10th-grade Calculus class, where they embarked on their initial entrepreneurial endeavor, a high school startup that ultimately didn't gain traction. Ben later led the frontend development team for the World Health Organization's COVID-19 App Team during his high school years.

Following high school, Jacob joined Apple, while Ben pursued higher education. When an opportunity arose on Jacob's team at Apple, he encouraged Ben to apply. Ben subsequently left the University of Chicago to work at Apple.

They both served as Senior Engineers in Apple's Conversational Engineering Department for approximately two years before departing to establish Freestyle. The creation of Freestyle was directly influenced by their observations of the shortcomings in the technology they encountered at Apple.