In this episode, Carlos interviews General Stanley McChrystal, a distinguished military leader with 34 years of experience commanding at a four-star level, including significant roles in Iraq and Afghanistan. They discuss General McChrystal's career, including his extensive awards like the Defense Distinguished Service Medal. General McChrystal shares his post-military endeavors, including founding the McChrystal Group and teaching leadership at Yale. The conversation delves into General McChrystal's books, particularly 'Leaders' and 'Team of Teams', exploring how writing these books shaped his views on leadership. Key themes include: - understanding the complexities of leadership; - the interplay between leaders, followers, and context, - and the role of character and self-discipline in effective leadership. The episode also covers practical insights on managing and transforming organizational cultures. General McChrystal shares personal anecdotes and reflections on leadership mistakes, personal development, and mentoring. 00:00 Introducing General Stan McChrystal 01:26 General McChrystal's Career Evolution and Achievements 01:48 Discussion on Leadership 07:15 The Three Myths of Leadership 09:58 The Role of Followers and Breaking the Cycle 13:15 Leadership Evolution and Organizational Dynamics 16:58 Challenges in Leadership and Adaptability 20:52 Team Dynamics in Startups and Large Organizations 23:40 Adapting Leadership Styles and Overcoming Mistakes 30:09 Commander's Dilemma: Vehicle Maintenance and Leadership Challenges 31:48 Leadership in Counter-Terrorism Operations 32:35 The Importance of Character in Leadership 35:42 Defining and Reflecting on Character 39:43 Personal Development and Daily Routines 45:26 Mentorship and Learning from Mistakes 55:54 Military Traditions and Cultural Questions 57:37 Conclusion and Final Thoughts Show Notes: General Stan McChrystal - linkedin.com/in/stanmcchrystal Carlos Espinal - linkedin.com/in/carloseduardoespinal mcchrystalgroup.com seedcamp.com General McCrysyal's books - mcchrystalgroup.com/about/books