Reddit is more popular than ever...and losing money.
They've asked their users to buy gold accounts.
The honesty is refreshing, and it might just work.
But I think there is a better model.
The amazing thing about gathering together such a strong, passionate, community is you can identify exactly what they want and sell such products to them.
Threadless thrives on this. They earn over $40m a year selling products to their community rather than finding communities for their products.
I'd be working on The Reddit Guide to Life (and other community-created 'Guide to' books), Reddit merchandise (t-shirts etc where members could submit their favourite quotes/ideas), organizing/facilitating Reddit events/activities around the world, and exclusive areas of the site members can pay to access.
There are no shortage of ideas for monetizing a community. Look to what other successful communities are doing and copy that. Mumsnet, for example, sells their guides, has an academy that sells courses on Ancient Greek, Jewellery Making, Writing Sex In Fiction etc..., hosts sponsored events, charges organizations to host competitions, and otherwise has a highly diversified income stream.
Reddit users have money. They've raised donated over $2m to charity in the last few years. They're willing to spend the money on things and ideas that match their community ethos. The challenge is to find the products they want to buy. The process of doing that is the most valuable part of monetizing a community.
Aside: If Reddit gave their top 10,000 members free Gold accounts for 1 year, my bet is a) the majority of them would pay to keep it and b) far more members would upgrade to gold account.