The Passion

In 2001, Leslie Singer was a creative director at a successful branding and marketing agency and had a teaching post at New York City's School of Visual Arts. But she had been trained as a graphic designer and always dreamed of developing a fashion brand based on her own designs.

The Plan

Inspired by the pattern-focused designs of Burberry and her obsession with accessories, Singer, 51, was determined to turn her black-and-white psychedelic patterns into a high-end line of scarves, gloves, belts, and bags.

The Strategy

Once her collection was ready to sell, in 2004, Singer started holding trunk shows. She figured her unique designs would get noticed by buyers from boutiques and department stores across the country. If she sent some samples off to celebrity stylists, she thought, she could probably also get a red-carpet boost.

What Went Wrong

Singer got great responses from dozens of boutiques across the country, but they all placed small orders, amounting to no more than a couple dozen scarves at a time. Singer needed higher-volume orders. But the big stores were hard to crack. When she did get meetings, they usually told her she was too small for them to take a chance on her. Or they would ask her to redesign her collection to match that year's trends -- in green, for example, or leopard print -- changes that she felt compromised her vision. Trendsetting magazine editors weren't any easier to persuade. After spending four years and $500,000 of her own money, Singer mothballed the business and went back into branding and marketing.

Lesson Learned

Singer admits she failed to do her homework on large-volume fashion retail: "I never looked at the retailer side, at how they buy, what the decision process is based on, who the gatekeepers are." She also thought -- mistakenly, as it turned out -- that her achievements would translate into open doors in the fashion world. "I was used to having a certain stature and status within my peer group," she says. "Not getting that with something so personal was a crushing blow to my ego."

What She's Doing Now

Singer is co-founder of the branding firm HS Dominion.