I actually hadn’t heard of iheartradio before, but after checking it out, it seems like as you mentioned it’s as much a podcasting/music streaming site as it is a radio network. And even then, it looks like it’s the biggest “internet radio” company in the US with a market cap of $250 million. Mark Cuban’s internet radio company was sold for $5.7 billion in 1999… which would be over $10 billion today. So I’m standing by my original statement that he absolutely fleeced Yahoo.
The concept is fine, and I’m not begrudging people who use it. But purely from a financial perspective it’s not worth anywhere close to what Cuban sold it for ($5.7 billion in 1999 for a single company that had effectively no revenue by comparison). From my other comment - the biggest US internet radio company has a market cap of $250 million today and that number has pretty much only gone down.