I got the audio book version of the Bitcoin Standard so that I can listen while driving. I like that it gives the history of money so that people get a context for understanding the importance and impact that hard money can have. The why is important, then move to the "how".
I think the best way to learn is to have skin in the game. Get them stacking right away with an amount they’re comfortable with. They have the rest of their life to learn.
What I’ve found is, having bitcoin (and being able to take part in what we’ve witnessed this past week) often increases the desire to learn more. It’s like a flywheel.
If the price goes down, they’ll also learn a lesson that can’t be taught through content — how to hodl.
The early Andreas Antonopulos videos are great at conveying how revolutionary bitcoin is, the ethical implications of a neutral monetary policy + immutable, censorship resistant transactions, and why the status quo doesn't appreciate it. It's hard to watch them without getting worked up and excited for the possibilities. I would start somebody new there before getting into the technical details.
I would get them to look into the existing monetary system first. Inflation, currency debasement etc. see if they have any issues with it. then point them whatever guides books etc suit them.
It must feel great to help someone take the orange pill. Now comes, for me, the hardest part, keeping them motivated with Bitcoin.
There is a lot of good information and therefore choosing where to start is very complicated. So as @k00b mentions, you should assess their background and needs.
Maybe starting by showing them how Bitcoin can help them with a specific problem they have would be a good start.
The information would also depend on what is easiest for them to consume. VIDEOS OR SIMPLE GUIDES. For me, when I entered the rabbit hole, I read the My First Bitcoin diploma book, simple and practical. Then the Bitcoin White Paper, The Bitcoin Pattern and the @DarthCoin Guides have helped me with good practices.
But if it is a person who really wants Bitcoin and not just wants Bitcoin, it is different, they must learn something very important, you have to do a lot of PoW.
I have some pdf and epub books that range from beginner to advance level in such a way that its worth reading.
But, I'm not sure how to share with you?