I like the jailtime app, helps me to decide whether to shoplift music or just download it.
They might as well add a iLawyer app, with a virtual lawyer at your side, who needs to spend money defending yourself against the RIAA?
You do the same thing everybody else does, show them what you have done, and what you can do for them.
The fact that you were involved in startups and managed to stay afloat last 7 years is an asset to you, not a liability.
I am not sure it's a good idea. You have time to think and edit what you write on Twitter and FB(I hope!), but being tracked real time is more like a compromise of personal space. Also, I think Skype already have a feature to share screen.