Decentralized stock issuance, exemplified by tZERO, aims to revolutionize capital markets by tokenizing securities on blockchain, enhancing transparency and accessibility. However, liquidity challenges persist. tZERO's platform struggles with limited trading volume, as private securities inherently lack the robust secondary markets of public stocks. Regulatory constraints further complicate matters, restricting investor participation and slowing transaction processes. Despite offering innovative solutions like fractionalization and same-day settlement, tZERO faces hurdles in attracting a broad investor base, with only a few digital securities actively traded. The platform’s pivot from cryptocurrency to regulated securities reflects adaptability, yet the illiquid nature of private assets and evolving regulations continue to hinder seamless liquidity, underscoring the complexities of integrating decentralized finance with traditional markets.