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On the other hand, if 90% of my friends sign up for the $1000/year plan, and I cannot afford that, they just lost a user.

Would the people willing to pay a high amount make up for the loss of the lower-tier levels? (Keep in mind that this is the kind of decision that you cannot ctrl-z out of.)

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Good question. I wonder what a good strategy would be for figuring out the near optimal pricing plan? The strategy would need to start off w/o painting yourself into a corner. In other words the initial pricing can't constrain future pricing adjustments by much. Also you'd want a strategy that allows for frequent adjustment down the road. Something like the Google "search algorithm" frequent tweaking.

Perhaps an increasing sequence of additional tiers could work? Start with just free. Then free or $10. Then free or $10 or $25 and so on. This avoids users feeling like they've been punished for being an early-adopter. Also users who aren't happy with their current tier can simply upgrade.

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