Business Crush: Aimee Cheshire of Madison Plus


On the list of things I love in this world, here are a few for ya: entrepreneurship, fashion, "real" women, not having to imagine every squeezing myself into a size zero (or even imagine how little I'd have to eat to ever be a size zero) and people who see a need in the world or the marketplace or their own closet, and instead of relying on someone else to create it, they do it themselves.

Well meet Aimee Cheshire of Madison Plus, because she embodies every one of the items on my "things I love" checklist, and is therefore the topic of this week's Business Crush post.

Aimee is the fashion entrepreneur and trailblazer behind the online universe that is Madison Plus (I just don't feel calling it an online store is enough - she's got editorial, trend coverage, exclusive sales, a blog and more).  Chances are if you've opened a magazine or flipped on a morning show you've seen them.  Aimee's success has been amazing and it made me wonder, in a world where most clothing lines and fashion sites rely on models that more closely resemble hangers instead of real women, how did she manage to do what she does so quickly and so well!  Instead of wondering, I went to the source, Aimee herself!

Below, find my exclusive interview with Aimee Cheshire of Madison Plus as she talks "a ha moments", entrepreneurship, plus size fashion, how to run a successful online retail business & more!

Though we can probably guess the “why” tell us the story of Madison Plus (MP) in your own words:  What was your “a ha” moment?  When and why did you realize to take the big leap and risk that starting a business entails? has been a lifelong project. Even though I didn’t always know it would eventually be expressed in the form of MP, I was born with the “a ha” moment. At a young age (I’m not sure when exactly) I came to realize that there was a problem with the restrictive nature of women’s fashion. Somewhere between only being able to shop men’s jeans and having to buy an adult women’s size for my communion dress, it dawned on me that I should not have to go through so much to buy a simple outfit.  I knew then that I had to do something to insure that no one else would have to experience such exclusion.

I carried those childhood memories with me and continued to question the industry as I grew up. Mainly asking, what are the reasons for the lack of clothing size 12 and up? In a quest to find out I made it my personal mission to understand and participate in all aspects of the industry. I lived it from modeling and styling to product development. As far as I know I am one of the few people out there who has experienced and worked in all aspects of the plus industry and seen it from all perspectives.

The moment I was struck to get my act together and create MP I was working in Product Development for plus sizes. I was presenting to my bosses a collection of harem pants and a knit motorcycle jacket, pieces that were fashion forward and flattering for the curvy silhouette. They were looking at me like I had two heads and that’s when I thought, “I will never impact anything staying here!”  Their only focus was on finding the next million dollar v-neck tee, not uplifting plus women and providing more options for us.  That’s when I knew it was time to launch something like MP and if I didn’t do it right away someone else would beat me to it.  I also wanted to take advantage of the recession since the economic downturn was a perfect time to create a company. I wanted to develop the website so that when retailers and brands started looking for new sources of money I would be there ready. I saw an opportunity to help jump start the redevelopment of the plus industry.
MP: How long had you been thinking and planning MP before you put the plan into action and launched?

The majority of work started in 2008, figuring out what business model would be the best platform and further researching the plus market. My initial impulse was to create a clothing line, but being all too familiar with the ins and outs of inventory and the upfront cost of creating a line, I felt it would be better, considering the market place, to build Madison Plus slow and steady. So many companies come out of the gate kicking and screaming, whereas I wanted to lay a foundation and create a brand that customers would come to know and trust.
Did you have experience in the fashion or online retail business already or was this entire venture a “learn as you go” journey?

I went to college at LIM and got a degree in fashion merchandising after having earned a bachelor in Psychology at James Madison University. I was immediately hired in product development , for a plus size catalog company. I spent many years working for them and learned so much about the corporate side of plus to gained a better understanding of the restrictions and difficulties of developing clothing for plus size women.

While in college I was a plus model and landed in the pages of Marie Claire but most importantly I gained an understanding of what it means to be in front of the camera. That being said, no amount of preparation can get you ready to launch your own business. It’s learn as you go almost every moment. The brand is developing at a rapid pace and I am quickly learning what my customer loves and figuring out how I can deliver it in the most efficient way possible.

What was the biggest hurdle in your early days as an entrepreneur?  How did you overcome it?

The biggest hurdle was the first one, just deciding to do it and stop talking about doing it. For many years I spoke about my desire to create something more for plus women, for many years it was undefined. Once I was able to take that leap of faith and start developing MP, it just took off.

What would you say are some keys to running a successful online retail website?

Stay true to your customer, keep the offering fresh and exciting and always look forward at what is next while keeping your feet firmly planted in the present.

Do you feel tied to the “real beauty” and realistic beauty image movement (real women in America don’t really all come in a size 0) because of the company you run.  Do you see yourself falling into a role larger than running your business, i.e. speaking to and for women who don’t fit the traditional beauty ideal that society and the media carefully craft?

I hope so. I believe that I’m at my best when I get to meet with a small group of women and chat about their thoughts and feelings about the fashion industry as a whole.

For a long time women believed that the lack of inclusion was due to discrimination and what I have found is that the lack of inclusion stems from a general lack of know-how in the industry when it comes to how to best include and execute plus fashion. The plus industry is vastly underdeveloped in comparison to the mainstream fashion industry.

I want women to leave my site feeling equal to those body types frequently featured in magazines. For so long we have been fooled into thinking that the size of your body equals happiness, dating life, and attitude and I know that they have little or nothing to do with each other. I still deal with the same issues now that I dealt with when I was a hundred pounds heavier. In the world of fashion I think its important to maintain the caliber of exceptional beauties that they feature. Aspiration and inspiration are so important but I just want to see more beauty in a variation of sizes, not just plus or the infamous size 0.

I want to impact the industry from the inside. I want slow and steady change. If it comes on too quick I believe it will only be sensational or end up a short-lived trend. The inclusion of more body types in magazines and in the fashion world has to be gradual and long-lasting.

What are some of your favorite features on Madison Plus?

I love our Straight to Plus feature and our Model Off Duty. I love showing off the styles of all the fabulous plus models. Staight to Plus shows our viewer how to get celebrity looks in their size and it’s important to attempt that even though you may currently not have the same amount of clothing choices that your straight size counterparts do. It’s crucial to buy and work with what is currently available or else retailers won’t see the demand.

Where would you love to see your brand go in the next five to ten years?

I would love for it to be the main destination for all things plus fashion from shopping to advice, a taste maker and an industry leader in the fashion world. I want MP to be the spark that illuminates the dialogue around plus fashion as well as a fabulous platform for voices representing the plus community to launch from.

For you, what’s the most satisfying thing about being an entrepreneur?

Playing by my own rules! I quickly realized when working in the corporate world that always conforming to the preferences of others was not for me.
What tips do you have for others reading this interview who may want to start their own businesses?

Be smart and pace yourself. Research and understand your market and how your voice is unique from all the others out there. Don’t quit your full time job until you know you can stand on your own two feet with your upstart. Developing a solid business usually takes longer than you think, but don’t get discouraged. It all starts with making that first leap.