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Well, the E-2 is an option if he can find an Italian company that is at least 50% owned by Italian's in E-2 or that could be classified as E-2. Here is a link:
He can also invest around $200,000 himself in an active business himself and get his own E-2 through his own investment. It may not need to be $200,000, but the law says substantial investment and few attorneys takes cases for less than $200,000 because since the investment has to be at risk, they don't want to lose a case and the owner be forced to sell everything to recoup the investment and go back home.
If he owns a business outside of the U.S. for more than 1 year and will continue to run that business, he can invest $100,000 or more in a U.S. business (doesn't have to be the same business, but must be related by ownership) and he can try for an L-1A visa. Here is a link to that, but keep in mind that both businesses have to be run and should be successful. He can't just come to the U.S. and forget about the business outside and let it die:
The H-1B is another option. The information on the H-1B is basically that he must have a job offer, the job offer must be for a company that is offering a position that is related to his degree and experience. The position must also normally require a bachelor's degree or higher. The company must have a need for someone in that position and must have the resources to be able to pay him what is normally paid to someone in that position. All these things must be provable with financials, business plan, etc. Also, because they are used up for this year, he will need to apply on April 1, 2016 to start working on October 1, 2016 or later. The exception is if he applies for a cap-exempt job and those are at an institution of higher education or its affiliated or related nonprofit entities or a nonprofit research organization, or a government research organization. Those are not subject to this numerical cap.
Here is an official link to the H-1B:
Here is a link to the cap:
The F-1 and J-1 are also possibilities, but for F-1 he would not be able to work and for J-1, many of those require him to go back home for 2 years before he could get Residency and marriage to a U.S. Citizen does not erase that requirement. Here are some links:
So there are options, but they are limited.
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