Currently, regulations try to limit unregistered sales of stock (private placements) to the “smart money,” either by informing investors through disclosure or excluding unsophisticated investors from the market. In theory, these smart-money approaches promote the dual goals of capital formation and investor protection. But in practice, regulators have struggled to craft effective disclosure or screening mechanisms. In light of these failures, this Article advocates for a new approach—investment caps that allow every investor a limited amount of “mad money” to invest in risky private placements. This mad-money approach can protect investors by encouraging basic diversification and liquidity, while advancing capital formation at least as well as alternatives.