I think you have a powerful opportunity here. Yes, he is a billionaire, but that means he is also human. Communication is a powerful tool, so this will be a great learning experience regardless of the outcome.
I would just reach out to him and let him know all of the things that you learned on your projects, what you did to try to save them, what you are interested in now, and then tie that into what he is doing (do your homework). If you tell him how you can fix HIS problem then he will be open to your work.
Worst case scenario, you are in the same situation. This is just a good way of acting in a place of diplomacy. Boldness, yet humbleness.
Also, because you are feeling the way you are about this particular individual, I would challenge you to start having conversations with "power players" on a weekly basis. This will help you to get out there, get some bumps and bruises, and play in the arena.
I can help you come up with a full "grand strategy" if you are interested.
