How This Former Investment Banker Became An Entrepreneur In The Fashion Business

Sculpting an enduring career in the menswear industry — a space not known for its luck or generosity — is no easy feat. Add to that the leap between finance and fashion, and success is far from guaranteed. In this regard, Zachary Prell’s achievements could be considered extraordinary.

The 47-year-old Southern Californian-turned New Yorker tells BOND OFFICIAL about his youth on the West Coast, early days in investment banking and venture capital and the inspiration that led to the launch of ZACHARY PRELL, his eponymous menswear brand.


Growing up in Southern California:

“I loved growing up in Southern California. I grew up skateboarding, and surfing near my home in Pacific Palisades. I was a California kid! I haven’t surfed in a while, but I had an active childhood, and I think it prepared me well for my later years.

I travel back to California once every three months or so for store visits and events with our department store partners such as Nordstrom and Bloomingdale’s. When I have free time, I visit my mother, Ellen, who still lives in the house I grew up in. She’s an incredibly resilient woman who faced a lot of adversity as a single mother raising my younger sister and me. She went back to college in her early 30’s to complete her undergraduate, and graduate degrees in order to start a new career as a teacher for special needs children – a job she loved doing for over 20 years. She’s a caring, thoughtful, and inspiring woman who taught me to always follow through, and find the positive in every challenging situation. Her father — my grandfather, Irving – also inspired me growing up. Irving was a true entrepreneur, a self-made man who never attended college, yet founded and operated a successful drug store in Los Angeles for over 40 years. He started from scratch and successfully grew his business, in part by connecting with his customers and team with his warm personality. He inspired me to become an entrepreneur and follow my dream.

From the West Coast to the East Coast:

Growing up, I didn’t travel a lot beyond California. When I was considering universities, I thought leaving the comfort of L.A. and moving to the relative unknown of Boston would be a memorable life experience. This was a perfect opportunity to learn more about myself and become immersed in a highly diverse, international collegiate environment. At Boston University, I studied both communications and liberal arts, and spent my time there working on dual degrees.

During my junior year, I lived abroad in London, where I had a chance to work for the international environmental organization, Greenpeace. My interest in the environment stemmed from my surfing days, when I got sick after swallowing polluted water. As the lone American in the office, I saw firsthand how a major environmental organization tried to slowly effect change. I even participated in a protest on Parliament Square. It was a unique time in my life where I felt empowered to try different experiences.

After graduation, this sense of adventure continued, leading to a move to New York City. I had a lot of friends moving there and applying for jobs in investment banking Analyst programs. I had no idea what these programs entailed, but I was intrigued, and thought this kind of position right out of college would provide a great foundation for experience in the business world.




Post-Grad Challenges & Rejection:

I was rejected from every single Wall Street firm I applied to! I didn’t have the required experience compared to others who studied finance. It was humbling because I excelled in college, and I hadn’t experienced that kind of universal rejection.

I went back to the drawing board and cold-called my way into an internship at an investment bank called Merrill Lynch, where I spent nearly a year working for free and soaking up as much knowledge as possible. I leveraged that experience to secure my first corporate job at Credit Suisse First Boston, a prominent investment bank in New York.

Once at CSFB, I joined the Mergers & Acquisitions Group as an Analyst. It was a highly competitive environment, and I spent many all-nighters learning how to write presentations and build complex financial models. I remember this being an incredibly stressful period in my life, but when I look back, I realize it helped me develop a strong work ethic.

Sparking an Interest in Entrepreneurship:

I began to favor working with smaller, more entrepreneurial start-ups, where I could help make a direct impact with growing businesses. With this in mind, I transitioned from investment banking to venture capital. I spent five years in VC, most recently with Polaris Venture Partners. It was a great opportunity to work directly with founders and management teams and gain a better understanding of how companies are formed and financed, industries are evaluated and products are made. I started to understand what it took to get a company started and was inspired to start my own business.

Polaris had a business casual dress environment. I’d been wearing button-down shirts to work for years that were comically oversized and fit me like a giant bed sheet! To add insult to injury, I was spending all this money on brands that I felt didn’t understand me as a consumer. I’m a regular guy, fairly trim, and everything was hanging off me. I started to wonder if I could address the fit problem, solve it from a consumer’s point of view and completely reimagine the perfect men’s sport shirt.

I got excited about this concept and decided to go back to business school to change careers and launch a new menswear brand. I attended Columbia Business School and over two years wrote my business plan, made lots of samples and pressure tested my ideas with classmates and professors. I took every entrepreneurship course that CBS offered.  

Building the ZACHARY PRELL brand:

Our brand’s value proposition was simple: better fit, exceptional Italian fabrications, smart design details and versatility – all at a competitive price. One of my CBS classmates introduced me to an advisor at another fashion brand, who in turn introduced me to Li & Fung, the international sourcing firm based in Hong Kong. I became Li & Fung’s smallest client and they opened lots of doors to new factory relationships in China. Early on, email correspondence with the team at Li & Fung was difficult, so after graduating with my MBA, I packed a bag and headed off to China, where I worked on product development for 18 months.

Truth is, I got fired by my first two factories for being too much of a pain about quality and consistency. The small initial quantities didn’t win me any points either. Looking back, I really had no idea what I was doing, but I was deeply passionate about creating a new and better collection of sport shirts. I feel fortunate to ultimately have partnered with TAL Group, a major force in the industry and our shirt manufacturer since launching (TAL is also our strategic investor, having invested $15 million in our brand in a Series A equity financing in January 2014).

With manufacturing in place, I then cold-called all the major Italian fabric mills, such as Albini, Monti and Leggiuno, and the families of these legendary companies all generously supported my concept for a new menswear brand from the start.

 I launched our brand out of my 500-square-foot walk up in New York City. The first collection consisted of six solid color shirts – that’s it. At the time, my apartment served as our world headquarters – sales showroom, warehouse and customer service center!  The world has changed so much since then. Social media is so important now. Having a dynamic website with ever-changing, relevant content is key. Strategic product drops and collaborations keep customers coming back for special items. Being able to talk to your customer through the direct channel is also more important than ever before.

When I started, wholesale was the primary sales channel. Our very first wholesale customer was Nordstrom. They gave me a chance in just one location, Dallas at North Park, in the fall of 2008. The Nordstrom sales teams got behind our collection and the shirts began to sell. Despite it being a very challenging time in the retail market, our brand grew significantly. I’m proud to share that the one door has grown into nearly 100 Nordstrom doors today. That relationship led to seven years with Neiman Marcus, and longtime relationships with Saks and Bloomingdales.

Gauging Brand Success

I have a couple of personal measures of success:

Team: success to me is about building a dynamic and experienced leadership team. I’m blessed to work with people I respect, admire and love like family. Creating a corporate culture where everyone is inspired is very meaningful to me.  

Collection: I’m proud to see how our brand has grown to include all categories from a modest collection of six sport shirts. We think about the collection every day so our customers can live their own story – desk to dinner.

Distribution: having national distribution, where customers can see, feel and experience our collection firsthand is important. More than ever before it’s about comfort, fit, quality and versatility. The challenge — and significant opportunity — is conveying these attributes in a compelling manner across all of our digital platforms.

Am I happy waking up every day doing something that I absolutely love? Yes. I love making menswear that guys love to wear. I love the personal aspect of visiting a store, of meeting a customer and having that personal interaction where I can hear feedback directly and integrate it into our collection going forward.

That’s the measure of success for me. Progression, growth and evolution — and being able to share it with our team.


Thoughts on Being Labeled a Fashion Designer:

I consider myself as an entrepreneur — a guy who had an idea and simply went for it. I’m not a trained designer and don’t think I could have come out the gate with a full lifestyle collection. I focused on one product and tried to really nail it. With some traction, customers began asking what’s next. We listened and began introducing knitwear, sweaters, trousers and outerwear. Over the last couple of years, our brand has evolved into a full lifestyle collection. Essentially, we want to establish a new dress code for men.

Creating Opportunities for Aspiring Entrepreneurs:

I hope I can inspire other people to follow their dreams. As a brand, we champion other entrepreneurs and have created a Visionaries campaign across all our touch points to celebrate people making their mark in the world.

My advice: there’s always going to be self-doubt, but I think it’s all about setting bite-sized goals and making positive progress each day. After over 10 years on this entrepreneurial journey, I have a ton of experience and advice to share. I’m really involved in Columbia Business School’s entrepreneurship center and am an advisor for student entrepreneurs and other start-ups. I want to share my experience and hopefully inspire others to go for it.

The Future of ZACHARY PRELL:

Our brand occupies a large white space in the men’s market — we appeal to the classic as well as the modern guy. What we are trying to do now is anchor on what we are calling the new dress code.

We’re still focused primarily on the US market and continue to expand our digital channel. Increasing brand awareness is critical. We have opportunities for international distribution and selective retail is also part of the plan. It’s important to ultimately reach our customers across all distribution touch points.

I feel incredibly energized and positive right now. Our brand is growing and continues to evolve. At the moment, we’re launching our Fall 2019 collection at market, which will be in stores and on our website early August 2019.”

The ZACHARY PRELL collections launch four times a year: spring, summer, fall and resort.