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“From Wardrobe Stylist to running a Software CEO ”

Ben Wolff didn’t set out to run a software company. He’s actually a Wardrobe Stylist in NYC who primarily dresses men and women business executives through his first company Re-Dress (Re-Dress.com). It was from trying to figure out how to grow Re-Dress that he came up with the idea for a better way to put outfits together and FasterPants (FasterPants.com) was born.

FasterPants is an enterprise software company in the Fashion/Tech/e-Commerce space and solves two big problems that online men’s clothing retailers face: Reducing inventory and Increasing UPT’s (units per transaction). This is done with a consumer facing engine that algorithmically sorts men’s clothing into 3 and 4 piece perfectly matched outfits ready for purchase creating the ideal environment for cross-selling and up-selling.


MO: Can you talk about how your idea for improving your first company, Re-Dress turned into an entirely new business venture?

Ben: Re-Dress has always been focused on using what the client already had in their closets. When I started Re-Dress I knew I never wanted to be just a Fashion Stylist or Personal Shopper. I believed that working with a person’s entire wardrobe to help define who they are and how they want to be seen in relationship to their careers was most important and soon became the mission statement for Re-Dress. That’s precisely why I call myself a Wardrobe Stylist. It was literally a rainy day in April about 2 years ago when I started thinking about how to grow Re-Dress. This process, as you can imagine, takes a while because there’s no clear cut answer to a question like that. The most important thing I did to find my answer was try and figure out what it was about Re-Dress (and me for that matter) that made us successful? The answer came back that not only do I work with my clients existing wardrobe, but I’m able to get at least 25 to 30 fresh new looks from that wardrobe without them having to purchase any additional pieces. That was the “AHA” moment for me and I thought what if I could make an electronic version of that? What if there was software that could automatically generate outfits based on a given inventory?!?!

MO: How did you go from being a Wardrobe Stylist to writing the mathematical algorithms that runs FasterPants? How did you manage to accumulate the knowledge to write your own software?

Ben: Let me answer that by saying I did not write the code. That is way above my pay grade. I have to admit to you also that I didn’t set out to write an algorithm either. I didn’t really know that’s what I was even doing at first. Once I knew that I wanted software created for generating outfits I knew I needed to breakdown the why and how individual items of clothing “Go” together to create an outfit so I can eventually explain what I wanted the software developer to do. What is it about color and pattern and type of clothing that can make a “Look” work or not? This was the problem I set out to solve.

After to talking with my friends and mentors (who eventually invested a bit of seed money) and telling them about my vision for a new company they suggested I start at the very beginning to find my answers. I went back to my roots in retail. I was very successful at many high end men’s and women’s clothing stores in NYC. I learned early that selling clothing wasn’t just about giving the client what they wanted but directing and guiding them to the right look by suggesting the best accompanying pieces to finish that look. For my bosses it was about up-selling and for my clients it was about Styling and in order to do that a great salesperson must know and understand how to do both.

The only way I knew to figure out what later became the Patent Pending algorithm was to go to my closet, pull everything out, lay it on the bed and start creating outfits to see if I could find a pattern in the chaos. Earlier I had bought some colored construction paper and cut out shapes in different colors so I could place them on each item of clothing as a makeshift labeling system (Very high tech!) and see what emerged. After many hours and days of this something happened. I discovered that clothing type, color and pattern and how an outfit was put together was the correct assumption for moving forward. It’s from there that I was able to write down the frame work for what later would be the algorithm.

MO: How does FasterPants work? What is your favorite feature of the site?

Ben: The FasterPants software takes a couple of complex problems like reducing inventory and increasing upt’s for the retailer and putting an entire outfit together for the consumer without having to page back and forth and makes both as simple as clicking a button. There are two parts to the software; The first is the enterprise component designed for online retailers of men’s clothing like; Macy’s, Bonobos, Casual Male, etc. and the second part is the consumer facing engine skinned to look like the retailers site where the “Outfitting” is done. Let me tell you how it works. In order for the FasterPants software to function the participating retailer sends us a feed of their inventory. We then “tag” each piece with a specific unique combination that allows the software to read and sort its specified outfit combinations according to the algorithm. So that’s the behind the scenes stuff for the retailer. What the consumer sees is once he clicks on the particular garment he’s interested in like a Blazer, for example, the FasterPants software will then show him every perfectly matched Shirt and Trouser combination that’s in the retailer’s inventory that goes with that Blazer and thus Outfits are born! This happens nearly instantaneously. The consumer also sees all the pieces displayed as an aggregate on a 3D Virtual Mannequin.

My favorite feature for the retailer is the “Real Trending” tool. This tool enables the retailer to get data on not only what individual pieces are selling, but in what combinations they are selling. This is huge and could potentially change the way the retailer will market to their customers and buy for their stores. I have a few favorite features on the consumer side including Style Filters and the ability to Filter by Clothing Type, but I think my ultimate favorite feature is The Virtual Mannequin (VM). The VM lets the users see what the outfit(s) will look like as an aggregate when put together before they buy it. It’s very cool.

MO: Where does your passion and style and fashion come from? Who or what were your early influences and inspirations?

Ben: My passion for style and clothing came to me later in life. Back when I first moved to NYC to study acting I had quite a few “Day Jobs” and one being in retail selling men’s and women’s clothing at Bloomingdales but it wasn’t until years later when I was working at Hugo Boss that I really fell in love with styling people. Something about the mixing and matching their clothing just made me happy and the clients I served as well. As for influencers and/or inspirations I can’t say I have anyone in particular. What I really love, and maybe these are the Influencers, are magazines like GQ, Esquire, Details, Vogue, Marie Claire, Lucky and on and on. I love looking at the way their stylists and photographers present each look. Each meticulous and beautiful. Each conveying a story. That’s what I try to achieve for my clients.

MO: You were recently part of a pilot episode of a new reality show called “Shop! NYC!” What was the most interesting or surprising part of the experience?

Ben: What I found to be most surprising was I didn’t get to choose my client for the Pilot. She was chosen by the producer and director so it meant that I would be flying blind until the day of the shoot. That could have gone terribly wrong. I didn’t know anything about her. What was her size? What was she looking for? How old or young was she? What if she just hated the clothing or the store or even worse me?!? I mean this is a reality show and you want drama so that was a little nerve wracking for me. Luckily besides having a great director we have a great cast. Fashion Stylist Luciene Salomone is no stranger to Reality TV. Her show, “Your Wearing That!?!” aired a while back so she’s a pro at this stuff and Kim Naci is such a funny, wonderful and accomplished NYC Stylist in her own right so I’m very lucky to be working with such pros. One last thing that surprised me was that you really don’t know what the final product’s going to be until you see it air. This is where you have to trust your director and his team. Our director, Daryl Goldberg, is pretty amazing and the way he approached the show is so unique in the world of Reality TV. You can really see it in the sizzle reel. I mean the comments we’re getting on our Youtube channel are awesome.

MO: What’s the most exciting thing on the horizon for FasterPants?

Ben: For FasterPants now and in the future innovation, business development and raising a seed round are on the menu. We’re in the planning stages with a couple of retailers who are looking to beta test the software and then roll it out on a larger scale. Once that gets underway we will get start coding the software for the women’s version (YES ,I said the Women’s version!!!). Then we’ll start exploring using the algorithm in other verticals. Also surrounding myself with the smartest people I can find to move FasterPants forward is exciting and important. People like Dan Marques our new CTO. Dan brings a wealth of knowledge, enthusiasm and 26 years of IT experience to the table. We’re so happy to have him on board. We’re always looking to build our team.

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