This podcast episode explores the history, challenges, and opportunities surrounding asset tokenization. It discusses why asset tokenization failed initially and highlights the factors that may contribute to its success now. The episode discusses the advantages of on-chain assets and the rise of stablecoins as the first successful example. It also examines the legal and regulatory challenges associated with tokenizing real-world assets, including distinctions between securities and non-securities and the need to understand securities law when dealing with tokenized financial assets backed by non-dollar assets. The episode concludes with predictions for the future of tokenization, including the tokenization of various financial assets and the potential of blockchain technology to revolutionize asset management.