Daniele recounts how Faire capitalized on the overlooked potential of brick-and-mortar retail with a 'try before you buy' model that quickly validated product-market fit. He contrasts today’s volatile startup landscape with the more stable environment of 2017, then traces Cash App’s origin from a risky Hack Week experiment to a secure, scalable platform powered by machine learning and proactive fraud detection. This experience informed depthfirst’s mission: using AI to secure open source software by identifying real vulnerabilities with minimal false positives. AI is transforming security, enabling deeper code analysis and context-aware testing through reinforcement learning and AI agents. While attackers gain efficiency from AI, defenders benefit more through superior context and transparency. The future lies in hybrid systems where humans maintain oversight, making faster, confident decisions within secure frameworks—blending operational rigor with innovation.