[DrewDevil]

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If I want to start an online service that also requires that people have an account on my site what are the legal issues I should be worried about and what kind of lawyer/people do I need to see?

Accounts may have more than $50k in them, we may have many users.

We may have many users and users would want to be able to deposit and withdraw easily.

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I would talk to a banking lawyer and an internet e-commerce lawyer... even if this is not a bank, you may be subject to banking laws regarding the holding of deposits, etc.