Born and raised in central Virginia, Weston first began learning ASL in 2009 during his time at Maggie Walker Governor's School. After encouragement from the local Deaf community, Weston completed the interpreter training program at Reynolds Community College in 2015 while working as the program's technology assistant. Transferring to Gallaudet University in 2017, he received a degree in ASL/English Interpretation with a minor in linguistics in 2019 while also working as a program assistant and contract interpreter. He holds national interpreter certification (NIC).

Since 2020, Weston has been working in a variety of settings as an independent interpreter across the state and beyond. In his spare time he enjoys gardening, photography, biking and spending time with his husband and dog at their home near Ashland, Virginia.