I recently sold a company I'd started right out of high school and slowly built up over the years . Is it going to be hard to be screened without any real work history and being "technically" unemployed even if I'm financial comfortable .

Not sure about 411 specifically, but if you lay out your situation, and are liberal with your personal information such as phone number and address, some gals will see you and they could then vouch for you with other gals and/or P411.

Tell them your situation and they'll suggest other info you can send them.  Worked for me