Toronto’s Shop My Clothes sells high-fashion, but needs a website infrastructure update

In 2009, Craigslist was the world’s most popular online marketplace.

2009 was also the year Jonathan Elias saw an opportunity to offer something similar, but targeted to a niche audience. A Torontonian with years of retail experience as a merchandiser in San Francisco, he envisioned an online shop for people to buy and sell designer clothing directly to each other.

“I’d been in fashion for so long, I had all these excess clothes. I tried to sell them on Craigslist but it was horrendous,” says Elias, who holds an MBA from the University of Toronto. “When you’re posting clothes you don’t want it to be a chore.”

So Elias decided to launch Shop My Clothes, an online marketplace dedicated to fashion.

It’s a free site where men and women can buy, sell and trade high-end pieces of clothing – everything from Louis Vuitton shoes to Marc Jacobs shirts and Burberry scarves. The site’s successful, with about 4,500 posts and 1,200 transactions a year. Postings are free, with revenue coming through paid advertisements.

But, despite its popularity, a combination of bad programmers and a poor choice of platform — Microsoft’s cumbersome .net framework — has turned the venture’s back-end into a nightmare. Delays, which started at the site’s inception in 2009, have left its digital infrastructure severely outdated.

Shop My Clothes does work fine, for users anyway, but few programmers know how to work with the .net framework. This makes updates slow and expensive, and the search for reliable help difficult.

“I wanted to do something that was user-friendly, different, community based and free,” Elias says.

Those lofty ideals only made programming more complicated. The browsing experience had to be more intuitive and functional than Craigslist, with personalization options so users can follow their favourite posters and flag others for poor quality.

“The minute we started working on it there was delay, delay, delay,” says Elias.

The search system – key to any ecommerce site – was optimized for ease of use and to retrieve relevant data quickly. It was also horribly complicated to code.

“The search system is relatively advanced, it doesn’t look that way, but behind the scenes there’s a lot going on,” explains Dave Lauer, Elias’s brother-in-law, Shop My Clothes’ chief technology officer and a financial services advisor to the U.S. federal government. Introducing paid advertising, which required a custom management system to control rates and the positioning and timing of ads, also took longer, and cost far more, than Elias and Lauer expected.

All that work culminated in six months of delays and a non-functioning website. So Elias fired his contract programmer. The replacement was competent, but unable to devote enough time to the project. A year-and-a-half later the website was working for users but had little in the way of a back-end — a programmer was still needed to change user passwords or items on the website’s front page, for example. Elias changed this by outsourcing the coding to India . This was expensive — Elias has now burned through his personal savings and no longer has the cash for updates moving forward — but got a fully-functional website online within months.

Cheesan Chew works at Idea Couture, an international brand consulting firm with offices in Toronto. She says Shop My Clothes made a mistake common to small startups by underestimating the amount of communication required between an owner and vendor – be it a programmer, graphic designer or copywriter. She says it’s important to ask questions about integrating social services, payment options, and a site’s level of security and visual appearance. Had the Shop My Clothes team asked these questions, she says, they may well have avoided delays by choosing to build their site on a different platform.

Still, the bulk of the site design is finally finished, and Shop My Clothes now has a hybrid development model, says Lauer. A programmer is kept on retainer, and the company outsources whenever the need arises. But that .net framework still makes every update an exercise in frustration because so few programmers know how to use it.

“Most of the younger generation is interested in open technologies because of the low barrier to entry to build a website,” says Lauer.

Chew acknowledges that creating a website today is easier than it was four years ago, when Shop My Clothes started.

“For the major platforms, there are plug ins and technologies that have been built to address things likes security, payments, location based services, and personalization,” she says.

Lauer says he and Elias are now working on plans to transition the website out of the .net framework and on to something open source, which will make it easier and much less expensive to update in the future. They also want to create a mobile app so shoppers can browse and buy anywhere. However, without the necessary funds in hand, they don’t yet have a set timeline for their goals.

This isn’t a problem for the time being, because the website is doing well despite its back-end issues. In 2011, Facebook fans grew from 1000 to 5000, the site sees 15,000 visitors monthly, and it’s gaining even more publicity through promotional partnerships with Levi’s and eLuxe, another online shopping site.

The only question is how long this success can last without the site needing a major update that its owners can’t pay for.

“It’s been a rough couple of years,” says Elias. But, he adds, “it’s definitely a struggle I’ve enjoyed.”