Weston was raised in Milwaukee where his first job was working concessions at Uihlein Soccer Park.

[2] During his undergraduate studies, Weston organized an abs class that met three times a week in order to combat obesity.

[3] He also worked in various residence hall leadership positions and chaired the Lawrence University Community Council's Judicial Board.

[6] He helped create the county's online COVID-19 dashboard to track cases, hospitalizations, deaths, and other data to inform the public and shape decision-making.

[7] As a result of his advocacy, Weston was selected as a member of the Milwaukee Business Journal’s 40 Under 40 2021 class.