For me the key take-away is that he couldn't recreate his success later.
"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."
"One Million People" - Huh, well I never. I had a similar idea, inspired by the Million Dollar Home Page, but 5 years before "One Million People".
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! :)
Well, in this case if was because of something he did.
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.
They allow sponsored content they're just really restrictive about it.
For example I couldn't wear my work shirt (with logo) during a 2 minute piece on a kids TV program. However, watch whatever is on on a Saturday night, guest appearance from some "star" and the host's question will be "so, you've got a [media product] coming out", with a promo image of the book/movie/CD/whatever. Or if it's a movie then they'll often show a short clip (aka advert).
If you watch a cooking show then it seems it's fine to promo a restaurant as long as it's high-end - here's such-and-such chef, fresh from his Michelin starred restaurant at Poshtown. It's quid pro quo but waiving [part of] an appearance fee in order to get publicity surely counts.
It's curious, some kids shows are all black-tape over the carton being used to make a craft project but then they have an "inside the factory" series which is a massive promotional piece - though probably not paid - for the companies with branding clearly shown. You might argue not "sponsored" but "we'll let you do this filming if you show our factories in a good light and keep our name and logo in the show" seems sponsored to me.
Makes you wonder though. The story about the million-dollar page is pretty interesting but there's nothing special about the Calm app, yet more than half of the article is about it.
"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."