[yakult]

It's a bootstrapping problem. People would only fork over that kind of cash if all the cool kids are already on it.

It might work if the founders are already movers and shakers at the center of that world, and they use their personal influence to sign up a lot of high value people they know all at once.

Alternatively, maybe you hire a few professional trolls to flaunt their (not necessarily real) wealth in the most obnoxious ways possible, get Gawker's spiritual successors to write some clickbait about it, and attract actual rich kids with the free notoriety.

Alternatively #2, maybe it's a front for a high-end escort service, or drugs, or some other service of questionable legality. The trick being you have to sign up online and go through some other backchannel to get the actual service. So you can sign up and get plausible deniability with the money changing hands.

[harperlee]

They can also gift "1000$/month" subscriptions to a group to bootstrap. That both seems like a huge gift if they are already charging that amount to other people, so the receivers are moved to use it, and it is super cheap for them as real marketing expense - that can perhaps even write off as the full dollar amount.