I think they've regretted it since 2008. Best estimate I've ever seen was $6m. Know why they always ramble on about Google analytics while pooh-poohing Alexa and every other legit traffic analyzer? 'cuz the majority of their traffic is porn. Free. Porn. They really did give violentacrez a "pimp daddy" trophy. Say Craigslist wants to show you an ad. They need to render that ad page once and serve it to everyone. Say Reddit wants to show you a comments page. They need to render a unique page for every pageview. 500m valuation, negative revenue. But that's okay, Gold will save us all. Chris Poole ran 4chan out of his mom's basement. Even after he'd been voted Time's most influential person of 2009 he couldn't get a job. Also, speaking as a default mod, corporations don't have to kill to have access to one of the 30 most visited websites in the world. They just need to do an AMA. Somethingawful charges you $10 up front. But then, they're tiny compared to Reddit, and have been since about 8 years before Reddit existed. But hey - it makes Rich money. Think about it: Every page Reddit renders has an intricate vote and browsing history for the audience. Every page Reddit renders is utterly devoid of rich media. It should be a CDN's wet dream: plug that into your database and serve ads all day long. But nobody wants to advertise on Reddit 'cuz they look at the actual traffic reports and see porn and piracy. So Reddit has a choice: traffic or monetization. Get rid of the porn and piracy and you'll sell ads... but get rid of the porn and piracy and you're Digg 3.0. Do you think Conde Nast will in the grand scheme of things regret procuring reddit?
I mean, hell, it cannot have cost them much.
reddit is a massive headache to be responsible for, I'm sure.
Moreso than any website/company of a similar size.
And financially it ain't worth much, at least tangibly.
But I still can't shake the feeling that most corporations would kill to have access to one of the 30 most visited websites in the world.
If they can figure out a way to monetize it intelligently... and that's just the option that takes the least brainpower to think of.