iHeartMedia, the largest radio company in the US, is exploring investments with several companies, including Apple, in advance of filing a reorganization plan with bankruptcy court, the Financial Times reports. The company has $20 billion in debt and filed for bankruptcy protection in March.

Sources tell Financial Times that Apple is one of several investors that have been considered, and iHeartMedia is looking for an equity stake worth tens of millions of dollars. An alternate source suggested that deal could look like a marketing partnership rather than a direct cash infusion into the company.

This could bring Apple Music’s Beats 1 to broadcast radio

If a deal were to come to fruition between Apple and iHeartRadio, Financial Times notes that this could deliver additional distribution to Apple Music’s Beats 1, bringing it to broadcast radio. Currently, Beats 1 is only available through the Apple Music and iTunes apps. The report also states that industry executives feel Apple Music’s flagship shows on Beats 1 helmed by DJs like Zane Lowe have not grown the service’s user base in the significant way Apple expected.

Apple has acquired a few music-based companies before, including song identification app Shazam, and its purchase of Beats, which laid the foundation for Apple Music. But investments into outside companies are more rare for Apple; the company has most recently taken stakes in the Chinese ride-hailing service Didi Chuxing and in Toshiba’s microchip business. But even with its debt and bankruptcy filing, iHeartRadio has dominance over the radio industry with over 850 stations, and commands considerable power with exposure for acts on big-name events like the iHeartRadio Music Awards.

Apple declined to comment.