Jimmy expanded his early career of selling radio sponsorships for the San Francisco Giants and 49ers into station ownership. He co-founded the six station radio group Evergreen Media, personally managing three of the stations in top ten markets, creating innovative brand campaigns and initiatives to accelerate their rise from last place to first in all key demographics and revenues.
Through strategic acquisitions and partnerships, he grew his six stations into 465, forming the company AMFM, Inc., the largest group in the country in the late nineties, generating over $2 billion in annual revenues. He served as Vice Chairman and CEO, overseeing the 64 million listener base, nationwide marketing group, internet division, and multi-platform distributions.
His interest in the convergence of traditional media and the internet led him to eventually serving as president of AOL Interactive, where he was credited with launching one of AOL’s most successful products to a member base at the time of 33 million.
He subsequently launched his own content focused national syndication company, the Content Factory. Jimmy hired Dan Patrick from ESPN and in just six weeks, de Castro had signed over 80 stations to the Dan Patrick show. In two years it was sold to DirecTV with distribution to over 200 affiliates in digital, T.V. and publishing platforms.
At the request of Tribune Media president and good friend Larry Wert, he stepped away from his company to accept the position of president of WGN AM. The station faced multiple challenges with declining revenues and morale. Jimmy restored staff momentum and returned the station to profitability, extending the rights of the Chicago Blackhawks, Northwestern Football and Basketball.