Making a Craigslist competitor for home rentals

    This post is part of a series about failed projects. I have almost a decade's worth of failed and abandoned projects in my dropbox folder, each with a load of random assets that other people might find useful.

    The plan is to share the details about what went wrong, and why the project never went anywhere. I hope it's interesting!

    Codename: Spaces

    The tentative name for this project was Spaces. On a whim I tried to get but the owner wanted six figures for it.


    I don't actually remember the true origin story for this project but judging by the last modified date on the files (2012) in my dropbox folder, and what I was doing around that time (moving), I think it's safe to say that this project was likely inspired by the nightmare that is trying to find an apartment in the Bay Area.

    If I had to guess I'd estimate that a large percentage of the population has considered making a Craigslist competitor at some point. With Craigslist looking the way it does, it's a pretty easy project to talk yourself into.

    The obvious problem is figuring out how to overcome the chicken and egg problem. You can build the most beautiful, fully featured Craigslist competitor imaginable, but without people listing things, you'll never be able to attact an audience, and without an audience you'll never be able to convince anyone to list anything. Every two-sided marketplace has this problem at the start.

    I thought I'd come up with a solution.

    Solving the Chicken and Egg Problem

    In addition to the marketplace, the plan was to try and offer a service that was so useful to Realtors and people making apartment listings that they'd be silly not to use it.

    The service would do two main things.

    1. We'd take professional, well-lit pictures of every room and detail in the home with a wide angle lens.
    2. We'd professionally write the listing, including all the important details, distance to attractions, walkscore, distance to public transport etc.

    The goal was to try and provide both of these services for under $100, saving people a huge amount of time and dramatically increasing the number of leads they'd get.

    The photography was going to be the most labor-intensive and expensive part of this. In 2012 Airbnb had just started paying local photographers $50 to swing by a listing and take photos of every room. So it was a possible goal to achieve, I think. Not easy, and a huge logistical challange for sure, but possible.

    Writing the listing would be easier. I wanted to build out a system that would automate as much of this as possible. By typing in the address of the listing, a lot of information could be pulled from some different APIs and parsed into natural-sounding language. I realized the descriptions that Realtors write are relatively formulaic after reading a lot of them.

    There would need to be some human input too, but a decent chunk of the heavy lifting could be done with software.

    The point of all this was to inject Spaces at the top of the funnel when realtors listed new homes. If they came to Spaces first to create the listing, we'd have a great source of high-quality listings flowing through the marketplace, hopefully making it easier to attract eyeballs looking for a new home!

    Quantifying good photography

    I was pretty confident that listings with good pictures would get a lot more interest, but I wanted to quantify how much more.

    To do this I listed my own apartment on Craigslist twice: once with so-so pictures taken with an iPhone, and once with higher quality wide angle pictures.


    The picture on the left was taken with a cellphone. The picture on the right was taken with a camera with a wide angle lens.

    The difference was staggering. The listing with good pictures got literally 10x the number of inquiries. That number would make for a pretty convincing sales pitch, I think!

    Why this project never went anywhere

    It didn't take long to realize how big of a logistical challenge running a company like this would turn into. It's very operations-heavy and as much as software could help, it would still be a huge undertaking.

    After revisiting this idea with a fresh set of eyes, I think it would be much more viable if the photography and marketplace parts were cut completely and the focus was just on building software that helped write and automate a lot of writing a home listing. If it worked well and saved Realtors time it would definitely be worth paying for!


    I have a few design files for the different pages that were never used that I put up for download if anyone is interested.

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    Jon-Paul Wheatley

    Jon-Paul Wheatley

    Product focused founder. Brit in the USA.

    San Francisco

    Making a Craigslist competitor for home rentals

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