Building a VC-Funded Fashion E-Commerce Company: Weddington Way CEO Ilana Stern (Part 1)

There aren’t that many venture-funded fashion e-commerce companies out there. The main reason is that the venture capital business is dominated by men, and typically, women happen to be more in tune with fashion. Ilana Stern is building a very interesting fashion company focused on bridesmaid dresses as the starting point.

Sramana Mitra: Let’s start with your personal story. Where are you from? Where were you born and raised and in what kind of circumstances?

Ilana Stern: I’m originally from Los Angeles. I was very close with my family. My dad is actually an entrepreneur of sorts. I was inspired by his hard work and passion for what he does. When I was 18, I left LA and went to the University of Pennsylvania for undergraduate studies. I loved the life on the East Coast so I ended up staying there after I graduated. I moved to New York to work as a buyer for Bloomingdale’s. I had a phenomenal experience there. I really got a lot out of my time on the East Coast, but I ultimately decided to make my way back to California when I was accepted by Stanford for business school.

Sramana Mitra: What year are we talking when you were finishing business school?

Ilana Stern: I was finishing business school in 2010. I graduated from undergrad in 2005. Then, I worked at Bloomingdale’s as a buyer for a little over three years.

Sramana Mitra: What happened after you graduated from Stanford in 2010?

Ilana Stern: I started working on Weddington Way full-time. When I was at Bloomingdale’s, I absolutely loved what I was doing. I was young, in my 20’s, and had P&L ownership, and a budget in the high tens of millions. Around 2007, some really interesting stuff was happening at the intersection of fashion and technology. Some players were cropping up and disrupting consumer experiences around fashion, leveraging technology. I became really excited about that. While I was getting a lot out of my experience at Bloomingdale’s and really enjoyed being there, the focus was definitely not on the intersection of fashion and technology. I realized that if that was where I wanted to focus, I needed to leave. That was what prompted my going to Stanford for business school.

As fortune would have it, at the Stanford admissions event in New York, I met Andy Dunn who is one of the founders and CEO of Bonobos. We were both passionate about the intersection of fashion and technology and really hit it off, and we kept in touch throughout my first year at business school. As I was trying to figure out what I was going to do with my summer between my first and second year, I reached out to Andy. Bonobos, at that time, was at an interesting growth period. I was lucky enough to get an opportunity to do an internship there. He basically gave me the freedom while I was at Bonobos to spend some of my time doing special projects for him.

During that summer when I was tinkering with ideas, one of the industries that I became really interested in was the wedding industry. While I was completely single and didn’t have any personal experience as a bride, I was in graduate school amongst students in their mid to late 20’s. Everyone was target audience in that they were recently married, getting married, or attending weddings. It was just an observation really that a lot of my peers seemed to be deriving a lot of joy out of weddings, but they also seem to complain about it a lot. It was that complaining that got me interested in the wedding industry and got me starting to dig that summer before my second year. What I uncovered that summer was basically just a really large industry in the US. It’s a $100 billion industry that is largely undisrupted. A lot of it has stayed the same for decades now in terms of how it operates.

This segment is part 1 in the series : Building a VC-Funded Fashion E-Commerce Company: Weddington Way CEO Ilana Stern
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