This article explores the enduring relevance of Theodore Roosevelt’s ‘The Man in the Arena’ speech for modern business leadership, strategy, and entrepreneurship. Drawing lessons from Roosevelt, the author highlights the significance of courage, risk-taking, resilience, and perseverance as essential virtues for business success. Through real-world examples such as SpaceX and Apple, the article demonstrates how leaders who dare greatly and embrace failure can drive innovation and long-term achievement. Actionable questions and book recommendations are provided to encourage readers to embody these principles in their own entrepreneurial journeys.