Dennis is an audiophile and he's having issues playing music from smartphone using Google Chromecast. It wants him to upload all his music to the cloud first. Leo says that his casting app may be corrupted. He should try another one, like AllCast. From the chatroom - Google requires you to upload your music to the cloud before casting with Google Play. That's what it's designed for: to play from the phone at home using the Google Home App.
Jamie wants to know how she can listen to her favorite comedians on her phone while she's driving. She's been playing the YouTube channel but that's eating up her data. Leo says that TuneIn, iHeartRadio, and other streaming audio channels have comedy channels that she can stream.
Chip listens to iHeartRadio on an internet radio called the Logitech Squeezebox. He's recently lost a lot of stations after an update, though. Leo has a hunch that many of those stations simply dropped out of streaming because of the cost of bandwidth for every single listener who is tuning in. It's a completely different model than broadcast because there's a hard cost. Its more like magazine publishing. But it could also be that iHeartRadio could be blocking the station.