In this episode, Lucas and Luna dive into Uber's self-driving car program, a project that burned through over $2.5 billion before being sold off in 2020. They explore why even a company with seemingly unlimited resources failed to deliver autonomous vehicles, the strategic mistakes that doomed the project, and three concrete lessons for CTOs and engineering leaders about moonshot investments, organizational incentives, and technology readiness. Drawing on public financial disclosures, the episode offers a grounded case study in managing high-risk R&D without destroying shareholder value. Whether you're a startup CTO or a corporate engineering manager, you'll walk away with a framework for evaluating ambitious technical bets.