Reading Arena magazine and watching TBPN makes me think that the media is pretty bad, but crypto media is even worse. 

I can't think of a consistently high-quality outlet that helps people keep up to date with the space in an entertaining and uplifting way.

Unsure if it's the content's fault, bad execution, or a mix.

two issues i see:

1. too few people with interesting opinions

2. too few interviewers who ask good questions

bad execution is consistently of high-quality at the media outlets

No one who can do this at the level of those outlets is willing to 

Boys Club maybe the only one

Late Night Crew

RIP /latenightcrew

Agreed there's a gap here, threadguy was a decent v1

Tldr.tech/crypto does a pretty good job at keeping people (or at least me) up to date in an uplifting and informative (although maybe not necessarily “entertaining”) way