An Interview with Stuart Weitzman

It was a bit of an enigma as to why he had chosen to speak at Caltech. A world famous luxury shoe designer, Stuart Weitzman, seems an unlikely visitor. After graduating from the Wharton School in 1963 at the University of Pennsylvania, Weitzman pushed his job offer at Goldman Sachs to pursue women’s shoe designing. In 2019, UPenn named its school of design after him, and now seven years after stepping down from creative director, Weitzman travels around the country lecturing at various universities— and Caltech was next on his list. His story—one that champions creative risk-taking over conventional paths—carries particular resonance in this institution where innovation is currency.

Here stood a celebrity designer who had been on the red carpet numerous times– his brand name known by women worldwide– and his first impression of Caltech was Club Room 2 in the basement of Red Door. Plastic chairs and concrete walls aside, his warmth and genuine engagement offered a striking departure from the often merit-focused, technical conversations that dominate life at Caltech.

“When you work at your hobby, there is no retirement,” Weitzman smiles ruefully as he tells me about his beginnings and inspirations. While many end up at Caltech through years of intensive study and careful planning, Weitzman’s entry into shoe designing came through serendipity—despite growing up with a family shoe factory, it was an unexpected detour that shaped his future. His journey stands in stark contrast to the calculated trajectories typical of Caltech students, and maybe there is something to learn from loosening our grip on the steering wheel.

He explains how he had painted stage backdrops throughout college for the theater troupe, but only for fun, “What can I say? I ended up in my hobby? Design was my hobby. I was artistic. I made things, built things. I was no Picasso, so I wasn’t going to make a life out of it. But in the end, I did.” A classmate, noticing Weitzman’s artistic talent, made an introduction to his father who was a shoemaker seeking fresh designs. After studying the manufacturer’s style, Weitzman produced twenty sketches, to which he received a strange response. The craftsman selected one design, tore it to pieces, then turned over another paper. Pointing towards the blank page, he challenged Weitzman to recreate the design again, believing Weitzman had copied the shoe design from somewhere else. “I use this in all my interviews, ” laughs Weitzman, “Two out of five designers have failed this for their portfolios.” When Weitzman successfully reproduced the torn design, the shoemaker made his offer: $20 for each design, except the destroyed one. It was Weitman’s first taste of his potential in the industry. He had never made so much money for just an hour of his time.

“It’s been my mantra, ‘two roads diverged in a wood and I took the one less traveled by and that has made all the difference’,” Weitzman tells me, referencing Robert Frost’s poem, “The Road Not Taken”. The poem, which we both had to memorize in high school, became his lifelong mantra and inspired the title of his evening talk. “I will say that taking the road less traveled by in all aspects of my life and my business, has made all the difference,” Weitzman wonders to me. After he continued to sell shoe designs throughout college, and making more money than his tuition cost at the time, Weitzman decided to push back his job offer at Goldman Sachs in lieu of creating shoes. “So many people, they see the finish line and they run to it, just on the same path everyone else has. But if you can get there this way. It’s fun. You come along the way, you pick up ideas that you wouldn’t find on the traditional route. It’s why the experience of a career is really invaluable, as much so, or more so, than the education.”

His anecdotes about the industry reveal all the careful steps he’s taken along his path towards building a fashion house to rival giants like Prada. Weitzman served as both the CEO and creative director of his company- roles that are typically split between two people in traditional fashion houses like Prada, Chanel, Gucci, and Coach. Starting small meant Weitzman had to develop both skill sets along the way. “I did learn to be a businessman, and to be an entrepreneur. That’s different than a businessman, you see,” explains Weitzman, “I think of the guys who run Proctor and Gamble as businessmen, but the people who run smaller companies in niche industries- they’re entrepreneurs. They do it right.” While Weitzman defied convention by wearing multiple hats, but he didn’t do it entirely alone. Barbara Kreger, Weitzman’s business partner of 46 years, is the Vice President of Design & Sales and of Product Development; together they have navigated their way onto the playing field of industry giants like Chanel and Valentino. Their easy dynamic becomes apparent through the evening.

“There would be no Stuart Weitzman without Barbara,” Weitzman states.

Kreger, who has personally tested every shoe pattern they’ve designed together, brushes off the praise with an easy familiarity. “Don’t say that,” she counters. “Of course it still would’ve happened. It would just be different.”

We explored his unconventional approaches, like avoiding outside investors and bank loans to maintain creative control, as Weitzman slowly grew his company. “I never hired anyone from a business school,” Weitzman says. “I thought creatives could learn that with us, since we’re very good at business. I hired creative people. If someone’s creative, they’ll be a better marketer than someone who studies marketing in school.” His hiring philosophy was a stark contrast to my and other students’ experiences in the current job market: “You know, if you bring someone into your company who’s been somewhere else and learned their way and it doesn’t mesh with what you’re doing, it’s impossible to change them, really, the spots are already there on the leopard. So I like people who were leopards without spots, and then they would pick up ours.”

In explaining his deliberate, measured approach to growth, Weitzman reveals his Truisms, nuggets of wisdom, values, and” accepted truths” from his years as an entrepreneur:

“When you’re an entrepreneurial business, you live an entrepreneurial life also, and it’s just one in the same” and “If I live my life a little bit like I run my business, or vice versa, I end up having fun with both” along with “I did what wasn’t done” and “not cutting any corners”

A patient, and steadfast man, Weitzman’s commitment to sustainable growth and his vision remained consistent. “I went very slow. I had a CEO President once, got rid of him after nine months,” Weitzman exclaims, “He said he would have built this business five times as big in half the time to where it took me 10 more years. And I said, What would you have done? He said, ‘I would have bought one or two little companies to add to it. I would have borrowed so many millions from the bank to build’” But this did not align with Weitzman’s values. “I didn’t need to be the biggest guy on the block— I needed to have a solid business. I knew I was giving great jobs to great people, and also giving in general— we gave so much money to charity. AIDS was killing our industry. It was 40% gay designers and 30% gay employees, and the fashion industry took it [AIDS] on in an organization to raise hundreds and hundreds of millions”

As our conversation turned to paths not taken—specifically, regrets and his original plans for Wall Street—he shared his musings, “That’s what business can do too. You know how much excitement that gave me on the first order I got from Neiman Marcus. Well, the results of something I did in Boston Children’s Hospital with my daughter was triple the thrill of what Neiman Marcus gave me with my first order. It’s good how you can do it with your family.”

It is evident that his success flows naturally from his instinct to elevate others and share credit freely. Weitzman’s genuine commitment to supporting those around him explains why his achievements feel both earned and inevitable. “The truth is I couldn’t do this alone, so I had to engage other people outside of my company, even, and to get them to want to do it, not just to do it because they’re making a buck. Nobody needs people to take a job to make the money. We need people to take the job to help build our cathedral. They believe in the vision. They believe in the vision and help you build it. And there’s a way to get them excited about it. And that’s the entrepreneurial spirit.” He has assumed a more pedagogical role now after endowing the Stuart Weitzman School of Design at UPenn in 2019.

“When I got involved with the design school, I insisted that if they wanted to be named after me because they were seeking international business— and I have a worldwide brand— then we insisted that a third of their courses had to be taken at the Wharton School.” Weitzman goes on to explain how everyone in life is a salesperson. Every day and in our careers, we are selling ourselves. After hearing a brief explanation of Caltech’s curriculum, Weitzman responds, “Your students here are going to go into some world where they have to be entrepreneurs. And a school like this doesn’t really emphasize that, doesn’t teach it. You don’t have entrepreneurial programs. But you know something, we are all salespeople. You are a salesperson. You’re selling yourself every day, some way or another. And when you want a job, you’re going to have to sell yourself.”

The changes that he made to the curriculum at the School of Design have already led to results. “The students, they are great architects, and [when] they got out in the world…10 years ago, they try to open an office. They don’t know how to hire people. They don’t know how to lead people. They don’t know how to finance what they’re doing. They haven’t had experience in sourcing all the wonderful materials. Maybe they have to learn it as they go along. But now, now they graduate, and, oh wow, they have such success in opening offices and maintaining them.”

Now, Weitzman spends his days lecturing at universities about his entrepreneurship journey and mentoring students. He is a father of two daughters and an active philanthropist. He attributes his success to luck, hard work, and “laughing through life”. He has been extremely grateful for the successes of his passion, and in the solidarity and ability of the fashion industry to contribute as a force for good. he has numerous other philanthropic projects such as preserving the cave of La Garma, and building a Spanish-Jewish museum in Madrid, Spain where his shoe factory is based.

As our conversation drew to a close, Weitzman offered a piece of advice for the Caltech community. “Think about a mosquito in a nudist colony,” he laughs, his way of acknowledging the numerous choices that Caltech graduates have. “Think of, and be a part of the community. That is the way you will have the most fun.”