Jason Droege discusses Scale AI’s evolution from autonomous vehicle data labeling to leveraging expert-driven training for advanced AI models, emphasizing that high-skill professionals are now essential for refining AI performance. He explains how reinforcement learning and human evaluations enable AI to act, not just respond, particularly in critical fields like healthcare. Drawing from his experience launching Uber Eats, he highlights the importance of understanding real business economics—like ingredient costs and gross margins—to create aligned, scalable solutions. Droege stresses independent thinking, avoiding hype, and focusing on urgent customer problems rather than occasional high-value ones. He shares lessons from failure, including overconfidence after early success, and underscores that 'not losing'—through disciplined risk management—is foundational to long-term wins. Effective hiring, mission-aligned teams, and resilience remain central, even as AI transforms workflows. The future, he argues, belongs to those who combine human insight with technological execution.