Depends entirely on the friend.
If he's a goldbug he'll have different blind spots than a cryptography nerd. If he's a traditionally trained economist books won't help, you'll have to go to church and pray for him.
Discussion
Lol. He's neither, a good well rounded dude that loves psychology, philosophy and is a local community builder. He's also a black belt in Japanese Jujutsu and just generally hates government. He's a reader so seems like the natural form factor for him to get into Bitcoin
Resistance.Money
written by philosophy nerds
Maybe something from nostr:nprofile1qqsf9jl9scw0c5snmkylpfhkppzgd7z7dupul6ms5yl52kfcz9jr8wqpzamhxue69uhhyetvv9ujuurjd9kkzmpwdejhgtcpzdmhxue69uhhqatjwpkx2urpvuhx2ue0qy28wumn8ghj7un9d3shjctzd3jjummjvuhsmqezp2? I'm currently reading one and it focus a lot in the societal and philosophical ideas, without requiring a lot of prior knowledge.
I think the important in the beginning is more to make him curious than to give him an overview. If the economics part really clicks (just got Broken Money and looks great for this), then he'll probably have questions about how bitcoin works and fixes the issue. Then he might question why governments cant't stop this and need something about the game theory (maybe Gradually then suddenly by Parker Lewis). Then he might find proof of work inneficient (for that I would give him nostr:nprofile1qqsxu35yyt0mwjjh8pcz4zprhxegz69t4wr9t74vk6zne58wzh0waycpg3mhxw309aukcursw35nwercdd3hzatxv56xkvnhx3cxxvnkxvmhwanr0pehvefhdfhkc7nwd9chzcmy095hvutsw9kx2vmvd9jzummwd9hkutcpzamhxue69uhkzarvv9ejumn0wd68ytnvv9hxgtcpr9mhxue69uhkgetjva5kw6fwdehhxarjxyhxxmmd9ux59hxq's Bitcoin is time). And so on.
Bitcoin is multidisciplinary so I don't think there's a sequential approach. Find what interests him the most, and feed the curiosity when the questions innevitably come up.
YO 🤘🏼 GIGI THIS IS CORRECT, IT DEPENDS ON HIS CONVICTION AMD CURRENT STANDING ON BITCOIN AND STACKING SATOSHI'S...
SOME PODCASTS AND CHANNELS MIGHT BE A LITTLE MUCH DEPENDING ON WHERE HE CURRENTLY IS ON HIS CONVICTION...