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In celebration of our 15 years empowering women, we are excited to introduce a retrospective collection of success stories from previous EWI alumnae. One of EWI’s board members, Howie Feinstein, is the contributing writer for this series. 


For some, the entrepreneurial journey is linear: a goal defined; an obstacle overcome; and contentment – even empowerment – achieved.  But such is not the case with E.W.I. alumna Alyscia Cunningham, for whom one journey leads to a fork in the road, where another begins.


A native New Yorker Alyscia decided to leave the corporate, nine-to-five life behind and nourish her creative, entrepreneurial spirit. She candidly admits that it wasn’t easy:  

“When I first made the decision to leave corporate America in pursuit of my entrepreneurial path, reality kicked in when I first experienced hard times. The lifestyle I was living, based pretty much on a consistent paycheck, dissipated. But I wouldn’t give up the freedom of peace of mind and time spent with my husband and (three) children, for anything.”

Undaunted, Alyscia and her husband developed a Washington-area home improvement business, Uprising Builders, LLC, to which she still devotes considerable time.  A talented photographer, she took on assignments for National Geographic, Discovery Channel, America OnLine, the Smithsonian Institution, and other outlets.

But resting on her laurels was never an option for a woman with Alyscia Cunningham’s restless energy. She felt the call to explore a new creative plane, uniquely her own. She came to E.W.I. with her dream of countering the traditional, media-saturated conception of feminine beauty with her own vision, focusing on natural hair and baldness. And in the Entrepreneurial Training For Success classes, she was buoyed by the company of fellow would-be entrepreneurs, with whom she continues to stay in touch for mutual support.

Following the success of her exquisite, coffee table-style book, Feminine Transitions: A Photographic Celebration of Natural Beauty, she has continued her quest to free women from the clichés and pressures of the advertising world. Her portraits are unaltered by Photoshop, revealing women in their natural state, without the façade they often feel compelled to put on for others. She is a master of her craft, with a calm, accepting personality which allows her clients to open up and show their inner selves.

But the journey continues. Alyscia has taken the plunge into the highly competitive and expensive arena of film-making. Her current documentary-in-progress – “I Am Not My Hair: Bald and Beautiful Me” – is a deeply communal labor of love:

“There is an entire community of girls and women involved in my project, that are not only counting on me, but sincerely believe in the mission of my work – of our work. And if I give up, we lose. What is for me, shall be. What I am born to create has no option but to be created.”

The logistical and financial demands of her new venture are indeed daunting:

“As I continue my journey as a first-time filmmaker, I admit that it hasn’t been easy. I can’t help but notice the challenge of being a woman of color breaking into a new industry. At times, I’ve thought to myself ‘I give up.’ Then it hit me: I thought about my mom yesterday. She was 25, married with three children, two, four, and six. She had a brain aneurysm which caused her to have a stroke, leaving her paralyzed on the left side of her body. If she never made an excuse, how can I? I have no excuse, and giving up is not an option.”

Giving up is Not an Option for Alyscia Cunningham
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