It's a great service, I've been using for a couple weeks now. I'd pay 4.99 a year for it.
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You've just summed up why it'll never go anywhere apart from acquisition: $4.99/year/user is not enough to run any sort of business.
It's a very hard concept to scale, both business wise and tech wise.
I'm not incredibly familiar with their setup, but as a consumer i can say with confidence that is not a service that i would pay a cent more than 0.99/mo