The story is all too common: I go onto Kijiji (a Canadian Craigslist clone) and find what I had been looking for: an iPad. I see the post’s price and presume it’s an “anchor” price, so I start off asking if the device is available and if they’d take a lower number. What follows is finding out the iPad posting was misrepresented as a “personal” sale, when in fact it was a business selling the product at a firm price, quoted without tax. Another asshole muddying what’s known as the “grey” market for the rest of us. Too many of these types of experiences, and you start to wonder if this can ever be improved past this level of a failed experiment.

The answer is no, of course. We’re probably doomed to let these sites fail, and fail hard. Something new and better will rise from the ashes. But, I thought, if I were to improve on them, what kinds of things could I build to improve upon this (now old) application?

The nature of tools like Craigslist requires a few very specific features that cannot be altered in any way, namely:

• Built-in anonymity. No person posting a product would have their identity, name, email address or other detail revealed by the system to any other user. Only by himself could these details be revealed. This is generally done today with sites keeping email messages behind a mail redirector with limited details passing through (such as a first name, or details in an automatic signature).
• The nature of being a market where individuals trade goods for cash needs to be preserved. These are the foundations of the system and have to be protected. While advertising might be allowed, I would remove all business-based product postings from the site. This is difficult to police, and too often, provides an incentive for sites like Kijiji to be paid so the listings are buried as posts. In fact, Kijiji is so bad at signalling business ads, that it feels like an effort to dupe users. So, do you think they’d work to remove businesses that abuse their system?

These two very important qualities make it near impossible to police the users because any sort of control of the payment process leads to an audit trail. For a site like this, you have to let the users decide how goods are paid for. That creates a conundrum that I think has kept Craigslist and Kijiji essentially stuck where they are. Now, years later, the world is changing and becoming more sophisticated (and connected). The next great tool needs to be built for that world.

How do I do it if I were building this?

1. Build a strong machine learning system. In fact, this would be the primary, ongoing development work of my site. The system would start, from the ground up doing simple computational work such as signalling accounts that create multiple posts that are the same. 1 I would then move to analyze all user messages and build recognition of patterns around people. Those that are clear assholes or who deal in bad faith, ban them. Those that don’t meet in public places, ban them. Those that are reported by others, ban them. Eventually, working toward predictive models that allow me to tell, for example, an account posting a specific type of products are likely to deal in bad faith and block them based on a specific behaviour.
2. Build a back-end of identity verification. This may be too far, but for those that may want to stand out, I may want to offer them the ability to verify their identity through a number of different metrics (Government ID, online details, other things). If the identities of users could be shielded from each other, and any government that might come calling, I might even implement this and force it on users.
3. Improve anonymity between users. Create a system that makes it very difficult to communicate outside the bounds of the site or mobile app’s messaging system. Yes, that means the website will have a messaging system. Attempts to use phone numbers or email addresses for external communications would be filtered out of messages wherever possible.
4. Offer users the ability to document in-person transactions. Either by post-sale reports or even uploading of video or audio of the sale itself. Encourage users to rate sellers and keep this information internal. Attempt to gather details about sellers and buyers in an effort to better understand practices. Again, targeting those who operate in bad faith and work to ban them. When appropriate, also report those who act criminally.
5. Remove any paid user tier. In fact, removing paid users, and even removing the ability to pay for ads that can be pinned. If the site is free, it needs to survive on other types of sponsorships or advertisements. Perhaps offering a paid renew-faster option might work, but keep that limited to verified users.
6. Control information that is specific to the most common products. Selling a 64 GB iPhone 6? Every detail about this phone’s specification is known, so pre-populate that on every post. In fact, I might even make the titles specific to the product also to create a more uniform searching or browse experience. For those that work to game the system with an injection of keywords in body text, they should find themselves banned by the identity system.
7. Make search actually useful. Searching these sites today is an experience of frustration. By building a great search engine and making sure the data is cleaner, users find more of what they’re looking for. This would eventually be extended by a browsing system and opening up to be better digested by search engines. With the machine learning work, t may also be extended by a recommendation engine for some accounts.

With some estimates of the grey market topping $2 Trillion, it’s a market that has not yet been acknowledged or dominated. This is a space ripe for the kind of application that could engender greater trust in the population, and reach those fearful of ongoing hassle in this space. This could be the gatekeeper for all localized transactions in North America. Possibly even build out to other unregulated currencies such as bitcoin or find a revenue stream from trusted shipping options.

The question is, who’s going to build the better mousetrap?