Some of the stunts he pulled in between his BBS days and megaupload was to royally scam "letsbuyit.com" which he got convicted for and then he tried to open a "very high-wealth individuals" automatic trading system which obviously bombed. And back in the day he flamed the German CCC and loved to flash the word "hacker" as if he belongs. He sold a company he founded, DataProtect, to the renowned TÜV Rheinland and it turned out to be a scam and crashed. And before that he got caught dealing stolen calling cards.
He is and has been a trickster, an opportunist, a self-proclaimed "hacker" and above all an egomaniac who now, by sheer luck alone, finds himself on the more fortunate, romantic Robin-Hood side of things but his basic principles and ideas and greed haven't changed one bit.