What kind of ancestor will you be? For Gwendolyn (Gwen) Webber-McLeod, this is the central question that has guided her in her current era of legacy-building and a question she encourages everyone to consider. Gwen does not think of legacy as something that comes later; instead, she believes it is defined by the actions that you take over the course of your lifetime.
“I want to be known as a woman whose every step, every breath, left a gentle impression of good in the world,” said Gwen. “And I am already being remembered the way I want to be. This is evidence my legacy is in action.”
Born in Nuremberg, Germany, Gwen spent her early childhood traveling and living all over the world and United States with her military family before eventually settling in Watertown, New York, where her father was stationed after returning from Vietnam. Upon graduating from SUNY Potsdam as one of five Black women on campus, without knowing exactly what path her career would take, Gwen was certain that she would work only for companies or organizations that demonstrated commitment to women and people of color. That’s one of the reasons why, when a 24-year-old Gwen moved to Auburn, NY, the same place that Harriet Tubman had settled from 1859 until her passing in 1913, she was convinced it was no accident.
“My parents decided when they had four girls that they were going to teach us to take the world by storm,” said Gwen. “And they saw educating us, teaching us about philanthropy and community service, frankly, as a way to fight racism and sexism.”
Believing that the eye is the limit, Gwen’s mother and father made sure that their four daughters could see a future for themselves in which anything was possible, despite society’s expectations or limitations. Both parents grew up in the Jim Crow South and met while studying at North Carolina A&T, a historically Black college and university. Her father entered a segregated Army and her mother was a teacher. It is this keen awareness of the sacrifices and triumphs of her ancestors and family members that propels and inspires Gwen’s own fight for freedom and equality, particularly for Black women and girls.
Two years after enrolling in a graduate management program, and after a long period of personal grief, Gwen founded Gwen, Inc., a private sector leadership development company that would enable her to cultivate and inspire the same type of professional and organizational leadership that she looked for at the very start of her career. While this bold step into entrepreneurship did not come without personal and financial risk, it allowed Gwen to found a company that was big enough to hold all of who she is — mom, woman, leader, coach, mentor, wife, activist, philanthropist, civic champion — and became one of her
With the birth of Gwen, Inc., came the start of You Can’t Fail, a mentorship and leadership development program for women of color. One of Gwen’s mentees, Caeresa Richardson, gave Gwen the courage and inspiration she needed to incorporate You Can’t Fail as an independent nonprofit, and together they co-created a multicultural learning community for women and girls who have historically been excluded from certain careers. Caeresa served as the founding board president of the organization, the tagline for which is “You Can’t Fail… because your history says you can’t.”
Gwen and Caeresa met over a decade ago at a Christian women’s conference, where Gwen was a featured speaker and Caeresa was her host. Gwen saw her younger self in Caeresa and Caeresa saw a woman who embodied the type of bold leadership that she envisioned for herself. At the time, Caeresa was working as an engineer for a supervisor who labeled her as “overly ambitious.” With Gwen’s encouragement, Caeresa updated her resume and made a career move. Years later, Gwen considers Caeresa to be her “legacy in action.”
“It’s inspiring,” said Caeresa. “Hearing her say that just reaffirms some of the things that I feel already exist in me.”
An entrepreneur, activist and philanthropist in her own right, Caeresa launched an incubator program for Black entrepreneurs in Syracuse, which received grant support from the Community Foundation’s Black Equity & Excellence Fund in 2021.
Moved by a sense of historical obligation to give back, Gwen has decided to support this same fund through a legacy gift. A former board member of the Community Foundation, Gwen recalls visiting our building for meetings and envisioning the day when she would be able to make a significant, lasting and community-changing gift that would do for future generations what her ancestors since 1619 have done for her. That day finally came last year, when Gwen named the Central New York Community Foundation as a beneficiary of her life insurance policy.
“With strategic intent, I have designated my legacy gift to the Black Equity & Excellence Fund to ensure that the region remains an equitable place for my people,” said Gwen. “I hope my gift can be leveraged to give organizations serving Black children the opportunity to expose them to people, places and things beyond what could be limiting for them.”