How to be convincing

I finally have the ear of my Bosses Boss and I'm struggling to get him to see things my way. He's a super busy exec and doesn't have much time or patience for the IM problem which has traditionally been our defense for getting funding for IM -- the loss of corporate memory, legal risk or disposing of the wrong information, the invasion of privacy of disclosing personal info, etc. So I've got to figure out what he wants and show him that my suggestions are the only viable solution. So much fucking pressure!
The other part of me doesn't want to care. Put myself out there, only to be slammed. He's an IT guy, IM is a thorn in his side that I'm sure he'd love to be done with it. How did we go from a budget of 1 million to less than 20% of that? How did we go from a team of 7 to 4? It's pointless. I'm horrible with rejection too. When I really care about something and put myself out there, I can't help but take it personally when my ideas go no where. But then again, I should take a risk. If I don't make a case for change that I really believe in then I have no right to complain. I got up early this morning to outline the business case that was swimming around in my head last night. I'm going to do this.