Pandora ($3.5B SiriusXM). Rhapsody/Napster — five ownership changes since 2001. Slacker → LiveOne. Rdio shutdown 2015. MOG → Beats → Apple. The pre-Spotify streaming graveyard and the on-demand-vs-internet-radio inflection that decided it.
Howard Stern was sued in 2017 over a broadcast IRS call. A federal judge dismissed the case in 2019. The dismissal is a footnote — the lawsuit is what the engines retrieve. A case study in shock-format media liability and the AI-citation gap.
Conan O'Brien has spent fifteen years moving to the next platform before the current one stopped mattering — Twitter in 2010, podcasts in 2018, a $150 million SiriusXM exit, the Oscars twice. The case study brands building for AI should be studying right now.
