Just how do you think Sonny is able to tell his parole office he is going to be investing in a startup, when his "finances had dwindled to zero" and "does not have the ability to pay a fine"? Possible, but extremely unlikely.
You do realise that in many start-ups not all of the equity owners invest capital and that even if they do it's often a token amount like $1.
Likewise, the consequences of violating a parole condition vary by jurisdiction as does whether or not parole can be terminated early.