Radio played a crucial role in the lives of baby boomers, but the millennial generation seems to be losing interest. The popularity of radio stations has been waning with the onset of streaming and on-demand services. As a result, some radio companies are suffering–including one of the industry’s most powerful titans.

The radio station giant iHeartMedia Inc, which is based in San Antonio, is reportedly contemplating filing bankruptcy. It is currently negotiating a final agreement with the Securities and Exchange Commission regarding its debt. The company’s investors have agreed to grant the corporation more time to reach a final agreement regarding its debt before it files under Chapter 11. The media giant has a limited time to reach an agreement with the SEC. iHeart is unlikely to file for bankruptcy in San Antonio. The company indicated that it will file in the U.S. Bankruptcy Court for the Southern District of Texas.

A long, troubled road

This is not the first time that iHeartMedia has come close to insolvency. In 2008, the media giant was bought out by Bain Capital Partners and Thomas H. Lee Partners, two private equity firms based in Boston. iHeart, which at the time had $18.8 billion in assets and $5.2 billion in debt, was granted 70 percent of the company. Last March, it attempted to renegotiate its debt from $20 billion to $14.6 billion.

A new start for a radio giant

iHeartMedia is one of the radio industry’s largest and most influential corporations. It owns 850 radio stations throughout the country, including 63 in Texas. In addition, it syndicates the radio shows of major hosts like Rush Limbaugh and Ryan Seacrest. Declaring bankruptcy will help iHeart clear some of its debt, but in an increasingly digital world, the media giant’s future remains unclear.