Placed a huge futures bet on Pittsburg to win the Super Bowl in August 2008. They defeated the Cardinals Feb 1st, 2009. It took 4 weeks for 4 payouts, after arguing with the casino's owner Big Tony every day; luckily a sportsbook ranking site called SBR helped, who had quite a bit of influence on governance of the off-shore gambling space. The winnings were tax free as it was offshore. I took all the money and bought various stocks. The market bottomed 4 days later in March. I didn't bet on anything for another 2 years. When I tried again, I found out I was banned by Western Union and Moneygram permanently. And that's how I was introduced to this thing called bitcoin. Online offshore gambling was actually the first illicit marketplace for bitcoin, not SilkRoad. Big Tony was kidnapped and murdered shortly after—for his bitcoin.