Note: I previously commented on here[1] and I am reposting a similar response to what I posted earlier

Having previously dealt with a chicken-and-egg issue when I launched an online advertising company, I understand some of the problems you are facing.

Similarly having visited Yoink, I noticed you asked immediately to signup via Facebook, I’d remove that and let users just browse (I did manage to skip the signup process by clicking signup by email as it didn’t ask me for one) it would significantly improve the user experience. Moreover, I’d make it clearer the posts users are seeing are for “New York” as it is a little small.

Likewise, since you’re initially targeting New York users I would place a landing page & ask users to signup via email to express their interest – you can use browser detection to ask them for their region OR simply just ask them.

In terms of acquiring users & growing Yoink itself then, I would implement the following strategies:

- SEO

This is a HUGE section but, I would definitely look at your On Page SEO to making it more “Local” & to improve some issues. For instance I would probably have Yoink operating from /new-york or /nyc – you should have a look at how Gumtree.com (eBay owned) are operating their site structure for “Cities” in particular.

SEO should be driving a large volume of traffic to your website which is why, I was emphasising the importance of HUGE in terms of the depth for this comment & the importance to Yoink.

- Social

Once again this is another strategy you should be using more effectively yet it feels like it’s an addon to Yoink rather than fully baked into the product. You should work on making it more baked into the product by encouraging people to post to Twitter/Facebook/StumbleUpon etc when they’re offering something, encouraging them to post when they’ve “Yoinked” something (in fact I don’t know if you do this but you should offer to “integrate” the services & provide the option to auto-tweet when they post on Yoink or Yoink something but give users a Yes/No option) or offering a leaderboard or something “This Month’s Top Sharers/User Referrers” etc you’d be amazed what people will do even for a $10-$25 voucher!

Likewise, you only have Twitter & Facebook – you should add Pinterest, StumbleUpon etc as well to encourage sharing & even a send via email to your friend’s option as well.

These are two strategies that are extremely important to the success of Yoink however, there are others you should integrate because; if there is an algorithm update etc you don’t want to be losing the bulk of your traffic overnight.
As a result you should look to implement the following options into your growth & user acquisition strategy

- Advertising & Partnerships With Sites In Your Niche

- Bloggers & Other Webmasters Within AND Outside Your Niche

An example would be to use Guest Posting – since you’re targeting New York only look for popular blogs related directly to NYC or read by a lot of NYC users.

- Offline Marketing

Word of Mouth will be your biggest source of traffic which is why you need to encourage your friends to tell everyone about it as well as, even produce flyers & network with Students (the biggest lovers of all things free!)

- Online Communities

Go to where your audience is and leverage them discover relevant forums, blogs etc and leave thoughtful comments and participate in their communities then leverage them to grow yours!

- Social Media Channels - Twitter, YouTube etc

- Email

You noted that Freecycle send too many emails but a daily/weekly email with site updates & cool favourite new postings etc will encourage people to come back to your site and us the service.

- Effective Site Branding

- Have a Blog

As well as guest post, create a blog & post interesting but relevant content which will have people engage with your posts from inside/outside of NYC (adding a landing page & getting their email address as highlighted earlier is another reason to try and grow this as large as possible). Posting posts such as “10 Things You’d Never Believe Are FREE But Are!” and highlight things offered by Yoink users would encourage it to be shared (it the things are cool or shown to be cool – I saw an “underground dinner” highlighted when I was browsing that sounded cool to users!) which will aid in the growth of your service.

[1] https://twitter.com/Yoink/status/269142284522635264