Back in 2003, Markus Frind had about 40 members to his then tiny dating site, Plenty of Fish. Today, the free dating site draws over 1.5 billion pageviews monthly. An article in Inc. gave an in-depth account of how Frind created a dating behemoth, solely through advertising. His strategy? Sell big sponsorship placements to competitive dating sites that charged.

Now, Frind thinks he's made a big mistake upselling his users to paid sites.

He wants to augment his business with some subscriptions. He's making it pretty clear on his blog that he's in the market to "acquire" a dating site he can grow into a subscription business:

Here's what he wrote on his blog:

I’m letting hundreds of millions of dollars in revenues slip through my fingers every year by sending people to competitors sites.   Given what everyone else in the market is doing now the only real choice we have is to acquire a mass market paid dating site or build one myself.   I am looking for something I can take and build into a huge site to rival the other top sites.    So if you are selling a site feel free to contact me!.   
I’m going to have a lot of work to do to figure out how to run a paid site properly.

1.  There are a lot of differences between free and paid,  on a paid site people expect limited high quality choices.   On a free site users expect unlimited choice.   This is why things like personality testing work so well on paid sites  and on free sites are considered more of a joke…  User expectation is so different.

2.  Site design for POF is fine as a free site,  but if i use that design on a paid site users would consider it a joke and not pay for anything.

3.  Paid sites require a lot of employees/customer service  and currently have little to no viral aspects to them.
At the end of the day paid sites are currently consolidating and the growth for the industry is flat,  especially in the US.  But within the paid sites category  the top few players continue to get bigger every year and all the others shrink.   I think there is a lot of opportunity right now and a opening to create a major paid site right now.