Winston has spent his entire life either attending or working at some of the most prestigious private schools in the country. As a result, he has experienced these schools in every capacity imaginable: as a student, teacher, coach, advisor,  and administrator. Moreover, he has worked at schools at the elementary, high school, and college level. Seeing schools from multiple perspectives has given Winston a well-rounded and balanced vision of what schools are and what they can be. Having worked on both sides of the table as a college counselor and college admissions officer, Winston can use this knowledge of what colleges and universities look at and care about most to promote prospective students to colleges in the most optimal way possible.

After growing up in Manhattan and attending St.Bernard's, a private all-boys school on the upper east side, Winston moved on to the Eaglebrook School in Deerfield, MA,  an all-boys junior boarding school, before finishing his high school career at the Pomfret School in Pomfret, Ct. While there, Winston kept busy by involving himself in several theater productions as a an actor, as the tenor section leader in the school chorus, as a proctor in a senior dormitory, and as the MVP and Captain of the Varsity Basketball team during his senior year. Winston then went just down the road to attend college at Connecticut College in New London, CT, majoring in International Relations and joining the all-male a cappella group, the CoCo Beaux, where Winston wound up receiving several regional and national awards as a vocalist.

Winston began his career in education in 2001, beginning with a one-year teaching internship at the highly esteemed Park School in Brookline, MA. Falling in love with teaching, Winston spent four years at the Fay School, a co-ed, junior boarding school where Winston taught 6th,7th, and 8th grade English, coached Varsity Girls Basketball and JV Boys Baseball, had advisees and was a dorm parent. Intrigued by admissions, Winston moved on to his alma mater, Connecticut College and was an Assistant Director of Admission before holding the same title for four years at The Williston Northampton School in Easthampton, MA. At that point, Winston switched into college counseling at Williston, spending another four years there as an Assistant Director of College Counseling. Winston spent a couple of summers during that time working at the St. Paul's School in Concord, New Hampshire, as the Co-Director of College Counseling, working one-on-one with 135 of the best and brightest public school students in the state of New Hampshire, and helping them navigate the college search and application process. In 2008, Winston completed his master's in Education at Lesley University in Cambridge, MA. In the summer of 2015, Winston was married to his wife, Kara, which coincided with a move to Indianapolis, IN due to a promotion that Kara received from her new company, Eli Lilly. Since that time, Winston has worked remotely as a college counselor with The Princeton Review, video-conferencing with students from all over the country, guiding them through the college process.