I started from Antifragile and didn't regret it. If you feel like drawn toward the earlier ideas, read Antifragile -> Skin In the Game -> Fooled By Randomness -> Black Swan. This might also be related that I usually have more interest in starting with practical knowledge and then digging deeper into the theory/more basic knowledge.

Sure. Any references to concepts from earlier books can be easily googled and learnt. Most books nowadays are around 200/500 pages but the essence is contained in only 20/30 pages.