The Road Not Taken

Similar to Robert Frost’s poem “The Road Not Taken,” entrepreneur, designer, and philanthropist Stuart Weitzman said he began his career in shoe design by going off the beaten path. “‘Two roads diverged in a wood, and I took the one less traveled by,’” Weitzman quoted from Frost’s poem. “That’s made all the difference. That’s how he ended the poem. And that’s how I began my career.” 

Delving into his philosophy on entrepreneurship and the history of his brand, Weitzman said gaining industry experience was crucial to founding his own company. “The worth of education—let’s say that’s one to 1000,” said Weitzman. “But experience is one to infinity.” 

Weitzman said he worked at a shoe company for five years before opening his own, where he gained valuable business knowledge. “It’s like I was not a startup,” he said. "I was already in business with all that experience.” Weitzman then discussed business truisms that guided him in growing his brand, the first being risk-taking.  

“Risk is your absolute best friend,” said Weitzman. “You can’t achieve great things without taking risks.” Weitzman also emphasized the importance of risk-taking in business, inspiring him to find a niche in the shoe-designing market. “I noticed on the red carpet, every actress was in a different dress, but many had the same shoe,” Weitzman said. “If I could create a shoe for all of them—that would be unique to them—maybe I could get my product in the public eye, on the red carpet. Maybe I could find my niche.” Designing and creating unique shoes for celebrities gave Weitzman’s brand the initial exposure it needed. As celebrities like Aretha Franklin gave Weitzman credit for his shoes, millions of viewers and celebrity stylists were introduced to his brand. 

Weitzman also emphasized the importance of originality and creativity in making business decisions. “Nothing could ever keep you more different and more competitive against your competition than your imagination,” Weitzman said. “You have to hang on to that.”

When he first entered the industry, Weitzman said he could not afford the models heritage shoe brands relied on for their successes. In marketing, Weitzman said he took the road less traveled by, emphasizing his brand and company image rather than his shoes in advertising. “Do something that’s yours, that’s unique, that catches attention,” Weitzman said. “It will pay off many more times than the cost of doing it.”

Weitzman also said using new and unique sources of inspiration was an important part of distinguishing a brand. “If you are looking for inspiration in the field you end up in, do not pay attention to what your competitors are doing,” he said. “That’s like a rotten apple in the basket … I looked past my competitors and looked for people who were not my competitors.” Weitzman said he looked to gladiator sandals from ancient Rome, Dr. Martens boots, and Julia Roberts’ boots from Pretty Woman as inspiration for his shoe designs. “It’s not limited to a fashion product,” he said. “It’s only limited to your imagination. And I’m sure in whatever field you’re in, you can think that way and create muses to help you be inspired.”

Weitzman said asking for help and insight is essential when starting a brand. “It’s so obvious you can’t do almost anything alone,” he said. “Or if you think you can, you can do it better with help elsewhere.”

Adapted from The Heights article by Madison Hoang '27

Co-sponsored with the Shea Center for Entrepreneurship.