Cinchifieds’ Simple, Grand Plan To Disrupt The Classified-Ad Space

Watch out, Craigslist: Cinchified aims to match buyers and sellers in a ridiculously simple way.



Eric Berry is one of the untold thousands of people who’ve tried (and failed) to sell his stuff on Craigslist.

“Every time tried to make a genuine listing, take photos, and write copy, it was really frustrating, because I’d get an offer for, like, $4, and then the listing would expire,” he tells Fast Company. And while he owns up to his assortment of “random junk,” items like computer speakers, monitors, and lamps shouldn’t be that difficult to unload. 

Most people would have cursed a few times and dumped the stuff off at Goodwill. But Berry is not most people.

With undergraduate and masters degrees in computer science and electrical engineering from MIT, Berry (who also happens to be a lawyer) thought about building a new and better way to sell through classifieds. Sharing his frustrations with then-colleague Shaun Zacharia, the two former Appnexus executives are now attempting to turn their negative experience into a solution. Called Cinchifieds, the soon-to-launch platform is geared to simplifying the sales process for both buyers and sellers.

What will set Cinchifieds’ solution apart is the platform’s ability to pair buyers and sellers according to demand. “On Craigslist, the seller creates a listing without any sense of what the demand is,” Berry says. With no built-in metrics for matching demand, especially for out-of-season merchandise, Craigslist fails its users, he adds.


The way Zacharia and Berry envision Cinchifieds, a buyer or seller need only list the name of the item. For example, to sell a television, the user logs on and lists “32-inch flat screen TV,” along with their email address. The back-end architecture of Cinchifieds makes a match, putting potential buyers in touch with the seller directly via email. That’s it. 

Trying to shift all those complexities off the user isn’t going to be easy, Berry acknowledges. “I’ve worked on the human genome project, so this huge dataset world is pretty familiar to me,” he says. However, linguistics is a discipline he and Zacharia have had to learn as the business progresses. 

Berry explains that there are a significant number of semantic hurdles to overcome if their matching process is going to be as user-friendly as it sounds. Bigrams–two words together that mean a very specific thing, such as “New York”–need to be seamlessly incorporated into Cinchifieds’ search functions. Otherwise, someone typing “New York Yankee ball cap” into the search bar is going to get results with any item having the words “new” and “york” in its name. Berry notes that when you add in the fact that there are regional differences in the way people speak, there isn’t one even one standard language model to build on.

Then there’s the problem of asynchronous matching. Just because the seller has that 32-inch flat screen doesn’t mean there’s a buyer right away. Without making an immediate connection, Berry says it’s possible that users will get discouraged and the Cinchifieds marketplace won’t be as robust as it needs to grow. This, he says, will be Cinchifieds’ toughest problem, even if it offers its service for free.

Currently, there’s a vast network of buyers and sellers with (possibly grudging) loyalty to the existing marketplaces. Craigslist–and to an extent, Oodle–haven’t seen too much competition (other than in specific niche channels) because of the sheer size of their respective user bases. Partnering with Facebook and Twitter solidified Oodle’s marketplace, by putting people who are already socially connected in touch to sell goods and services.


The bright spot in all this is that Cinchifieds caught the attention of the Entrepreneurs Roundtable Accelerator (ERA). As part of its second class of startups, all participants get a $25,000 investment, office space in Times Square, and access to ERA’s group of more than 200 mentors. Last year’s class scored funding from such high-profile VCs as First Round Capital, Lightbank, and RRE Ventures. 

Berry says Cinchifieds is not nearly as developed as its officemate Appy Couple, but he’s taking it one day at a time. “We feel like we have a compelling offering and we are giving it our earnest and best effort. Three months is enough time to get something together for [the mentors] to invest in if they want to,” he says adding, “It’s a work in progress.”

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[Image: Flickr user Mark Brown]

About the author

Lydia Dishman is a reporter writing about the intersection of tech, leadership, and innovation. She is a regular contributor to Fast Company and has written for CBS Moneywatch, Fortune, The Guardian, Popular Science, and the New York Times, among others.