Billed as learning from the masters (ostensibly in a subject you are trying to master), I find it more interesting as evidence of what sorts of people become masters of their craft + I use it to help me build out models of people who I admire enough to make part of my...shoulder brigade?
(For a number of them, I think they saw it as maybe a way to share their story/what they’ve learned about life, more than just their job; it’s a bit like they’ve done portraits of the people rather than their subject.)
I’d start with David Sedatis, then maybe Ken Burns (he’s way more epic than I suspected). I also enjoyed Frank Gehry, the architect, and appreciated his views on the value of a person creating something that’s uniquely them.
Many others are interesting without being “my people” Annie Leibovitz, Jimmy Chin, Bob Iger, Doris Kearns Goodwin, etc.
(Annual subscription is ~$100 and they periodically have a "give one, get one" deal for e.g. Christmas or Father's Day or whatevs)