The new new commerce screenshot

With its emphasis on design, has become a go-to site for "product porn."

It’s that time of year again — time to log on to our favorite e-commerce sites, that is. They are sure to have another banner year. But it’s been an interesting last few years for a new breed of commerce sites that are gaining millions of users and boatloads of cash. These sites are distinctly different from their predecessors in that they have social, gaming and entertainment elements deeply woven into the user experience. They’re able to do so by leveraging the technologies and social graphs that were but a glimmer in the eye of the first commerce sites.

The first wave of e-commerce was built around the functional. Amazon, CDNow and others succeeded in putting the basic shopping experience online. It was hard enough for sites to translate our mouse clicks into packages that we’d receive, with all of the attendant systems, workflow and business processes that needed to be put into place. It was hard and expensive to get basic e-commerce order and fulfillment, and their attendant business processes, in place. At Live365, we spent more than a year and burnt more than a $1 million in 1999 building an online store to sell CDs. One could have the same front-end functionality today for $99 a month using Shopify. Ouch.

That’s not to say that the first generation e-commerce companies didn’t innovate. CafePress, eBay, Hotwire, and Priceline, among others, innovated on the business model front, but their sites tended towards the utilitarian, rightly eschewing anything that might distract the user and impact conversion rate.

“Here we are now, entertain us!” — Kurt Cobain

Enter the second wave of e-commerce

Not so the new breed of e-commerce sites. They obviously optimize for conversion. But their core value proposition is based on entertainment, gaming or social. To channel Maslov, now that we’re able to easily buy the stuff we want and need online, we look to fulfill our “higher” needs via commerce: To express ourselves, to identify and connect with one another, to be entertained.

Companies are popping up and getting funded in several categories:

Flash sales: Vente Privee, Rue la la, Gilt, JetSetter and their kin were probably the first to go for high production values in the presentation of their product. This high-gloss veneer combined with the urgency and serendipity of a flash sale clearly struck a nerve. is clearly on to something in this arena. As my friend put it, “It’s where people go for a little product porn during their lunch break.”

Crowd-sourced, user-created, demand-led: CafePress and Zazzle are the pioneers in this category. Threadless and its clone, Spreadshirt, have brilliantly built design-oriented communities with a game component. is taking a different approach by ensuring demand for their products before they get manufactured.

The new window shopping: Open Sky is a platform for celebrities and experts to curate things for us to buy. Others, notably Pinterest, Polyvore and Svpply, are taking the notion of curating to the logical next step by allowing us to roll our own lists of things we love, while FantasyShopper here in the UK, is introducing a game-like element to this.

Story-based commerce: As high-end brands have gone more and more mainstream, we increasingly desire other ways to express ourselves. Products with stories behind them are one way of doing this and Etsy, the platform for artisans, stands tall in this area.

S-commerce: Subscriptions, that is. ShoeDazzle, Birchbox and Trunk Club are high-profile examples of sites taking a subscription approach that gives their subscribers both cost savings and a “story” from the serendipity of what you get in your monthly shipment.

Big brands: Not to be outdone, the luxury brands are increasingly investing in entertaining their consumers online. Victoria Secret, with the annual runway show, is probably the pioneer in this area. But nearly all brands are investing heavily in rich media content including Ralph Lauren, Burberry and Hugo Boss.

This is by no means a comprehensive list of the models and activity in the space (unlike Elizabeth Knopf’s exhaustive analysis on Quora on why e-commerce is such a hot area in VC) but it hopefully gives a glimpse as to the “new new commerce.” It may well become the norm in the years to come as these new sites grow into their own, and as the incumbents respond in kind. We will simply expect our online shopping experience to be social, to be fun or to have beautifully presented products. As we’ve seen in music, there will be different curators in fashion, travel and other categories, from whom we will decide what to buy. Pinteresters, Polyvores and Svpplyers whose influence may well rival that of magazine editors and retailer buyers.

But in fact, the new new commerce isn’t so new: Artistotle is said to have noted that “Man is, by nature a social animal.” He was on to something. In fact, the fear of people and public places, agoraphobia, is literally “fear of the market.” Whether it’s the storytellers spinning yarns in the main market square in Marrakech or the flower sellers on Columbia Road hawking their wares in their Cockney accents or the auctioneer at the county fair, we have socialized and been entertained while shopping for centuries. And as long as we remain a social animal, it’s only natural that we will look for the same fix online

Rags Gupta, based in London, is currently on sabbatical from the online video company Brightcove, where he has been vice president, international. Prior to that, he was an executive at Live365 from 1999 to 2004 and is currently an investor/advisor at 8tracks. Follow him on Twitter: @ragsgupta