"First, he tried Pixelotto, a spinoff of the Million Dollar Homepage selling advertising space, then PopJam, a social network for sharing funny content, and One Million People, similar to his first success, just with photos instead of advertisements. None succeeded the way he hoped."
I think mine was a bit more innovative, (but just as likely to have failed!) - rather than just a grid of faces, with users paying $3 to add theirs, mine was free, and was going to scale the images in proportion to traffic and likes for that user. The aim was to get users to promote their image (therefore the site) through social media. The user that drove the most traffic would share in a prize funded by ad revenue.
I wrote the shape fitting algo, then abandoned the idea! :)
I don't think that was dumb at all :) .
The initial page idea was great and almost inevitable to succeed: cute when you hear about the concept, very easy to implement, almost sure to attract media attention (and have stories bring in more interest), etc.
So, in a sense, the lotto was coming up with this idea, not that the idea succeeded.
The problem is that his other attempts where either rehashes of the same but with no novelty factor anymore, or not that interesting in the first place.