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When Jonathan Elias moved back to Toronto from San Francisco, the self-described fashionista ran into a problem trying to sell high-end clothing he no longer wanted.

Traditional consignment businesses wanted commissions too high, he found eBay cumbersome to post, and listing and shipping fees too expensive, and Craigslist and Kijiji, he felt, were cluttered shopping experiences.

Based on the idea that necessity is the mother of all invention, Mr. Elias created ShopMyClothes in 2009, a free online marketplace to buy pre-owned, gently used high-end clothing and accessories.

To learn more about the business, I interviewed Andrew Macdonald, who joined ShopMyClothes last April as chief operating officer.

Q: How does the service work?

A: With ShopMyClothes, interested shoppers can browse the marketplace without signing up for an account. They can search using our advanced tools, such as filters to search by geography, categories (e.g. jeans), type (e.g. slim), size, and brand.

When they find something they like, they submit an inquiry via our site and, from that point, communicate with the seller directly, usually via e-mail, but sometimes text or phone.

Buyers and sellers usually meet up in person to complete the transaction (we suggest a local Starbucks or Tim Hortons), as this way items can be tried for fit, feel, and condition. Buyers get a great deal as well – items typically retail for 25 per cent to 30 per cent of their original sale price, and are without any taxes or shipping costs.

Though sellers must sign up for an account, the process is simple and posting items for sale is free. The listing tool is intuitive, and their 'for sale' listings reside in our database until the item is marked sold or removed from the site. About 30 per cent of items posted to our site to-date have sold.

Q: What market niche is it filling?

A: We are the only free, curated marketplace tool focused on local resale of the best brands in fashion. We are focused on building a community of fashion lovers, not merely bargain hunters.

A number of elements of this 'business definition' are important to us.

We are local. For resale of gently used fashion items, we think this is a crucial element to having a positive transaction experience. Users have told us they are most comfortable meeting up locally, so they can see the item in person, check its condition, and, most importantly for fashion items, try it on for fit and feel.

We look at every single item posted to the site on an hourly basis. If the brand does not fit our site's mandate for high-quality fashion, we gently ask the seller to de-list it, and if they don't comply, we remove it.

Additionally, authenticity is a huge concern of high-end fashion buyers, and we maintain a strict "no fakes" policy. If an item is listed as a "replica" or a "copy," we immediately remove it. If an item is suspected as fake by us in our manual screening process, we ask for proof of authenticity from the seller. If they can't provide it, their listing is removed.

Additionally, there is a feedback flagging system for the community to police itself, and we will be making this tool more robust in the coming months.

Q: What has been the reception so far?

A: With any marketplace business, there is a classic chicken-and-egg scenario. You can't promote the site to customers before there are sellers in the marketplace, because who wants to shop in an empty store? On the other hand, how do you convince sellers to set up shop before there are customers walking the grounds?

Fortunately, we had some advantages that helped us get past the 'critical mass' hurdle for the number of sellers on the site to attract customers. Not only was Jonathan able to seed the marketplace with a few hundred of his own items, he was also plugged in enough to the Toronto fashion scene to attract high-quality sellers. We're doing over 20,000 unique visitors a month, and recent growth has been 20 per cent to 30 per cent per month. Page views are close to 100,000 per month.

Q: What's the business model?

A: In the short-term, we are entirely focused on building and growing the community, and the value it offers to our members. In the long term, the business model will be to generate revenue primarily through advertising sales.

We take our responsibility to our community very seriously – our ads will be tasteful, targeted to our demographics and community interests, and unobtrusive.

The site will always remain free to use. We will also offer promoted listings for a nominal fee (i.e. listings at the top of the page), as there is value here – these tend to get four to six times as many views as non-promoted listings.

Additionally, we will look to partner with brands and companies that could serve our demographics well.

Q: What are some of the key lessons you've learned this year?

A: It's a long road, and, if you are to survive with your sanity and self-confidence intact, you need to take a long view. The best way to do this is through constant and obsessive goal-setting.

I have my daily to-do list; we have monthly target traffic and community statistics, and quarterly and annual goals. We also have categorized "on-going activities" charts tracking our progress across our Web development objectives, promotional programs, and so on.

It goes without saying that, as an entrepreneur, you need to be self-motivated. We all get that. But what I've learned is that you also need to train yourself to be self-critical, and, probably more importantly, self-congratulatory. This is not to say you need to be arrogant or brash – I think it's better to keep the boasting to yourself lest you struggle and end up eating your words. Rather, in the quiet moments after you've had a particular success, take a moment to enjoy it.

Special to The Globe and Mail

Mark Evans is the principal with ME Consulting, a communications and marketing strategic consultancy that works with startups and fast-growing companies to create compelling and effective messaging to drive their sales and marketing activities. Mark has worked with four startups – Blanketware, b5Media, PlanetEye and Sysomos. He was a technology reporter for more than a decade with The Globe and Mail, Bloomberg News and the Financial Post. Mark is also one of the co-organizers of the mesh, meshmarketing and meshwest conferences.

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