We're just speculating here, Monksdream, so here's my thoughts.
Matt had worked at S.I. first, and was a geek. When he left S.I. he started Ihub, I think at 21 yrs old. I believe it was as he got more involved in Ihub, a site that attracted the 'wrong' type of investors due to its penchant for penny stocks, that he was perhaps approached and succumbed to the lure of easy money -- success beckoned, wine, women, lambos. How could any twenty-something-year-old resist?
Newly