Explore the challenges of implementing security strategies in startups through this 36-minute conference talk from BSidesSF 2018. Gain insights from Rafae Bhatti's experience as a startup CISO, learning how to navigate obstacles such as limited budgets, vendor fatigue, and talent shortages when operationalizing security. Discover the disconnect between textbook security principles and real-world challenges faced by security teams in smaller organizations. Examine illustrative scenarios that highlight common hurdles and receive practical advice on anticipating challenges, making sensible trade-offs, and effectively implementing security strategies in resource-constrained environments.