Depends on where he’s coming from

If he’s from a tech background, the “Inventing Bitcoin” will answer most of his technical questions, but the big gap will likely be economic, so Bitcoin Standard or Broken Money are great fundamentals

The Little Bitcoin Book incorporates many perspectives and is a good lead in to a choose your own adventure exploration like “21 Lessons”

If he’s a finance nerd, then “Why buy bitcoin” will provide familiar framing

“B is for Bitcoin”

“Sovereignty through Mathematics”

“The Internet of money (v1-3)”

“The bullish case for Bitcoin”

So many wonderful resources and starting points now; there is no one perfect place .. just start and let your friends know you’re around for questions 🤝