Schengen Visa - Date of Departure after first intended stay
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You must apply for an Italian D-Visa (Long term/Residence permit) that allows you to work.
A Schengen C-Visa (Short term) only allows 90 days in a 180 period.
As part of your Business, state you you must travel periodically back to the US. That should be no problem.
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Source: stackoverflow.com
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