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Jordan Ravka runs Casualkiss, a dating site that recently converted their free memberships to a paid subscription model. Jordan was nice enough to share an overview of the experience, which I have posted here with only light editing. If you are a free dating site looking to convert to a paid sub model you’ll want to read this. Feel free to chime in with a comment, this is a hot topic and I think we all need to be discussing the issues surrounding free-paid conversion, because Jordan wasn’t the first, and he won’t be the last to face this daunting task.

After being free for years, Casualkiss converted to pay format last September. Price point was $5/month – $29 for entire year.

Casualkiss attracts a young Canadian demographic which make it difficult to convert members.

To keep traffic high during the transition to pay, they gave 3 month free accounts to all current members with the restriction that they cannot contact any newly joined members unless they upgrade.

Two months into the program, Casualkiss was hit with large DDoS attacks which took about three weeks to resolve. To re-earn trust with its members, they gave away lots of free memberships and extended the early adopter program.

The early adopter program was discontinued on February 28 with the idea that credit card Christmas blues ended and disposable income was on the rise.

According to Casualkiss, this was a terrible mistake. While sales increased by about 30% for a few weeks, traffic plummeted by 50%. It became such a problem that current subscribers were canceling their paid accounts as they found less members to interact with. Even worse, a few weeks into the cancellation, sales dropped to below normal.

After much debate, Casualkiss re-instated the free early adopter program 6 weeks later. Getting the users to come back has been difficult, specially with Hotmail’s spam filters. Fortunately, traffic has slowly started to rebound as word is starting to spread as have sales. Casualkiss has since come to realize that the early adopters provide word-of-mouth advertising and increase the value of the service for new members.

They initially worried that re-implementing the free program for early adopters would make paid subscribers feel “ripped-off”. The opposite has happened. Subscribers are grateful that more members are around and feel the $5/ month is worth it for full contacting privileges.

In conclusion, trying to sell something that was previously available for free is next to impossible, even if the service you offer is unique and cheap. Its not the money, its the mental transaction costs.

One other note, while the average age on Casualkiss is 23, the average age of paid subscribers is 29.