College and More, Inc.
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Professional Educational Counseling
Dr. Gay Stebbins Pepper
Founder and Director

Dr. Gay Pepper is one of America's leading experts on the college admissions process. Having worked as an Associate Dean of Admissions at an Ivy League school, a college counselor at several private schools, and an independent college advisor, she brings that rarest of all skills to the admissions task: perspective. She has experienced the admissions process from every possible angle, and brings all of that experience to bear on her work with students, parents, individuals and groups.


B.A., With Distinction, Stanford University, CA
M.A., Washington University in St. Louis, MO
Ed.D. Columbia University, NY
Post-Doctoral Study, Oxford University, England


Dr. Pepper worked as Associate Dean of Admission at the University of Pennsylvania for five years before becoming a college counselor. She served as counselor for 23 years in leading secondary schools, including: The Dalton School (NYC), Greens Farms Academy (CT), The Community School of Naples (FL), Shorecrest Preparatory School (FL), and Crystal Springs-Uplands School (CA). She was founder and director of The Scholar’s Workshop (PA) in 1980 before founding College and More, Inc. (CT) in 2005.

Dr. Pepper concentrates on high school students who seek admission to colleges that are the best fit for their talents, interests, and needs. She has worked with admissions professionals at highly selective colleges throughout the country to gain admission for her clients.


Benjamin Franklin Medal for Outstanding Service to the University of Pennsylvania

Byrnes Foundation Fellowship to Design the Finger Lakes Summer Seminar in Experiential Learning

Johns Hopkins’ Gifted and Talented Program for High School Families, Wesleyan University Guest Speaker, 2003- 2008

Editorial Board, The Fiske Guide to Colleges 2001 to present

Educator of the Year, Gulfshore Life, Collier County, FL

English Speaking Union Summer Fellowship, Oxford University

Noyes Foundation Environmental Fellowship, Columbia University


Making the Match: The Key to Successful College Admissions

Understanding Financial Aid and Meeting College Costs

Weathering the College Process: What Parents Need to Know


Finger Lakes Seminar

Project Santa Fe: An Adventure in Cultural Anthropology
“I cannot overstate Gay Pepper’s powerful influence on the success of our children. Gay’s ability to instantaneously read people and match them with colleges is extraordinary, reflecting her expertise as well as her sensitivity and insight. Everyone trusts Gay because of her egoless compassion, impressive intellectual alacrity, and her seemingly limitless sagacity. Gay is passionate about the wellbeing of students and understands the needs and sensitivities of parents. In addition to her innate intellect and magnificent education, Gay draws on great inner strength, insight and compassion in her work with families, making her superbly effective.”
Head of Independent Day School, and Parent

“Dr. Gay Pepper is an extraordinary educator and consummate professional whose expertise in college counseling give you enormous confidence. In addition to serving as an Associate Dean of Admissions at the University of Pennsylvania, Gay has traveled to colleges throughout the United States and abroad to meet with admission deans to discuss the unique features of their college. Her greatest gift is the wisdom and empathy she brings to her work with families. She is both mentor and friend. Gay has an uncanny way of inspiring students and guiding them to colleges that are ideal matches.”

                                                                                                                               Parents of Sons at Reed College and Tufts University

“The college guidance process is more art than science. Many have mastered the statistics but not grasped the nature of the student. Others have mastered the student but are clueless as to the appropriate choice. In Gay’s case, we got the rare combination of both. Our son was gifted but had a different learning style, presenting a challenge to find the right path and the right fit. Not only did Dr. Pepper help our son design an appropriate college program but also was a tremendous resource, a strong ally and a needed confidante in this stressful process. We are enormously grateful, knowing that our child is the direct beneficiary of a remarkably well thought out roadmap”

Parents of a Son who completed two music programs before attending an Ivy League College.

“Having Dr. Pepper guide us through the college admissions maze was one of the smartest decisions we have made as a family. Gay takes college counseling to a new level of sophistication. Her approach is state of the art. Analyzing the innate abilities of the student as a starting point, she combines these insights with the values, interests and goals to provide a framework for building the college list. Gay was an inspiration, giving us good counseling at each stage. She always went the extra mile, whether it was making that phone call to an admissions dean or providing application strategies. Dr. Pepper brings an extraordinary range of talents to her work, along with boundless energy, positive encouragement, and personal warmth. We give her
our highest commendation”

                                                                                                                                                 Parents of a Sophomore at Duke University

What they have to say about Gay Pepper
Dr. Gay Stebbins Pepper, Founder and Director
Winter Office (December 1-April 30)
7032 Pelican Bay Blvd. #104
Naples, Florida 34108
Summer Office (May 1-November 30)
2301 East Avenue
Rochester, New York 14610
With age comes wisdom, so I'm told... yet having known you for nearly two decades, I am more certain now then ever, that educators with true brilliance at the secondary level are, simply put, few and far between, and that age and experience never guarantee wisdom or brilliant performance. Having known and worked with you, I have been "in the presence" of a rare combination of intellectual brilliance, wisdom, and your nurturing heart. You are, dear friend, a rara avis.   You have personally "lifted" so many kids, transformed people's lives in such profound ways, that you remain an inspiration for those who have the clarity of vision to recognize someone of your extraordinary gifts.

I do not know any one else in my career who comes to each session with a student with more openness, more convivial elan, and with such a fundamental personal appeal that lets a kid know that you are fully present, willing to serve, and ready to give voice to aspirational thinking.  I used to observe you in such meetings, initially to ensure that you could deliver... but over time, I recognized that I was observing simply to watch a masterful performance as you worked your magic.

Alas, we are no longer together...  but who knows just where the journey  will lead us. With gratitude, love and respect,

James Landi, former Head of Community School of Naples