Private Lender. Deal first or approach about financing first?

[Robert Fountain]

I'm looking at buying my second rental and this time I'm going to go with a private lender.  The good news is that I have some great connections from my previous job.  I have a great relationship with the previous owner of the company and he just happens to be a private lender.  

My question is, should I find a deal first before approaching him or should I ask him out for a cup of coffee and discuss my plan and see if he's on board?