Shari grew up in Milwaukie, Wisconsin in a working class, black neighborhood where she played with friends in the streets until dark. She has an intense pride in her Midwest upbringing and the value of work ethic and strong values. She majored in Philosophy in college and is fascinated by how systems work. Shari became a lawyer, then a TV news anchorwoman, then was recruited to run Dress for Success in Portland. She credits her childhood lemonade stand as the entrepreneur experience that has started her obsession with innovating.