How did he make his millions? Presumably via the usual 'street pharmaceuticals' business model of ruling through fear and getting lots of people hooked on his merchandise. He learned from the master, Miguel Angel Felix Gallardo, known inevitably as 'The Godfather' and the world's most powerful cocaine smuggler even after his arrest in 1989. El Chapo ('Shorty') is better at avoiding jail: despite a $5m bounty on his head, he's still at large in Mexico. Basil Fawlty may have been an inspiration: Guzman escaped a maximum-security prison in 2001 by hiding in a laundry basket.
The secret of his success? Innovation and hard work. He is believed to have built an elaborate network of tunnels under the Mexican-US border, ensuring his drug-runners remain literally under the American authorities' radar.