30. Charles Ergen
As viewers turn to streaming services, Ergen’s satellite TV provider Dish Network has seen subscriptions fall 3 years in a row. But Ergen, a former professional gambler, has been hedging his bets. Since 2008, Dish has bought over $21 billion in wireless spectrum licenses at auction from the Federal Communications Commission. In March Dish issued a report to the FCC discussing plans to build out a faster 5G network that could work with the growing number of devices connected to the internet.