Notwithstanding all of the money already invested in security and privacy: privacy as surveyed is in decline and global communication infrastructure is increasingly insecure. Why is this so, and what can we do about it? Three concepts explain the problem of relating capital to security and illuminate the path to improved results: 1) definitions and outcomes of investments in privacy and security have been risk based and speculative. 2) expenditures for speculative risk abatement tend to compete poorly with alternative allocations, such as spending on quantified risks and spending for profit. 3) product budgeting has yet to fully embrace the notion that privacy and security are core to form and function. Security and privacy have not been monetized as elements of brand. This paper explains these concepts, relates them to the allocation of investment capital, and recommends actions for companies, their R & D executives, and boards to enhance success in the market.