Saylor isn't the person I'd choose to introduce someone to Bitcoin with. He has some good talks about finance, but I don't think he knows as much about Bitcoin as most think. He also isn't the most captivating speaker when it comes to crypto.
If I were going to recommend a more fun and knowledgeable way for you to introduce someone to Bitcoin, I would go with Pomp's Best Business Show podcast. It's a lot of fun to watch and they have some really great analysts and guests on there quite frequently. I think it's entertaining and educational, as well as being a bit more youthful and likely to catch your friend's attention.
Yes... There are few captivating speakers who really know every angle. The learning process is usually quite a long journey, and there are many ways of beginning, as well as progressing through.
Saylor has influence for his reputation and following because Microstrategy has always interacted with a wide variety of other business models. In that sense I would think he is more of a generalist, and would maybe just motivate listeners to find other sources, looking from their own specific point of interest.