The real story here is Conor's wealth isn't anywhere as large as he wants people to think it is. This sentence is worth 1,000 words:
"This has sparked a flurry of legal activity in recent weeks, as Mr McGregor’s lawyers try to prevent the disclosure of his tax and other data, which they say is designed to embarrass and “harass” him over his “celebrity status”."
Connie is going to go broke, and his bag of tricks has all but run out. Now you know why he's trying to pimp his business ventures so hard.