Same as me and very close to same age. Started with TWiT podcasts plus Buzz Out Loud with Molly Wood and Tom Merrit. On my iPod nano second gen. Got exposed to John through TWiT and startd listening to No Agenda, and still do. I massively disagree with the politics of John and Adam and frankly find some of what they say to be hate speech, and don't endorse their podcast because of that. But I still listen to it in the background and skip the problematic parts because I frankly just like hearing their voices after listening to it twice a week for 20 years.
I think John is a product of his generation and environment. Adam too. I don't think they're bad people, but very misguided in some ways. Despite that I am very sad to see John has passed. I really admired his dedication to the show and schedule for so long. He was a true professional in his craft.
I owe a lot to Adam and John in terms of entertainment, comfort, and contributions to my worldview from a young age.
In 1984, while arguing that Apple’s new Macintosh might fail, Dvorak wrote:
“The Macintosh uses an experimental pointing device called a ‘mouse.’ There is no evidence that people want to use these things.”
It's a shame John didn't live to see his prediction come true - I think we're very nearly there as AI starts to do most of our interfacing with computers instead of mouse and keyboard.