To fly from the USA, he will need to sign a statement that he complies with one of the 12 categories for a general licence under the US Office of Foreign Assets Control (OFAC). He will obtain his tourist card from the airline, or from an agency that works with the airline. In most cases, the tourist card can be bought at the airport in Miami, or it can be ordered in advance. He should check with the airline that he plans to fly with.
The only difference between the tourist card you will get and the one he needs is the colour. His will be pink, indicating that it was issued by the Cuban Consulate in the USA. Yours will be green.
There is a detailed explanation of travel from USA to Cuba at FAQ #19 at the following link:
Edit: ps. John beat me to it with posting the link.Edited: 12:15 pm, March 30, 2017
-:- Message from TripAdvisor staff -:-
This topic has been closed to new posts due to inactivity. We hope you'll join the conversation by posting to an open topic or starting a new one.
To review the TripAdvisor Forums Posting Guidelines, please follow this link: http://www.tripadvisor.com/pages/forums_posting_guidelines.html
We remove posts that do not follow our posting guidelines, and we reserve the right to remove any post for any reason.