The most significant founder mistakes often arise from abandoning one's own judgment to do what is conventionally expected. Jason Fried notes that these errors feel worse because you aren't just failing, you're failing while trying to be someone else, which undermines the core identity of your company.

After a massive failure with their domestic fund, WCM launched an international strategy staffed with an operations person with zero investment experience and a business school dropout. This counterintuitive bet on raw talent and a fresh perspective became the foundation for their turnaround and massive growth.

The most common failure mode for a founder-CEO isn't a lack of competence, but a crisis of confidence. This leads to hesitation on critical decisions, especially firing an underperforming executive. The excuses for delaying are merely symptoms of this confidence gap.

CEOs provide a curated view of their company's culture. To get an accurate picture, talk to people who have left the organization on good terms for an unfiltered perspective. Also, ask behavioral questions like 'What would you tell a friend to do to be successful here?' to uncover the real cultural DNA.

Orlando Bravo's first deals as a young PE professional were a catastrophe, with two going to zero. His mentor, Carl Thoma, gave him a second chance but with a crucial lesson: you can make mistakes, but you cannot make the same *type* of mistakes again.

All founders make high-impact mistakes. The critical failure point is when those mistakes erode their confidence, leading to hesitation. This indecisiveness creates a power vacuum, causing senior employees to get nervous and jockey for position, which spirals the organization into a dysfunctional, political state.

Experience taught Herb Wagner that great leaders consistently surprise on the upside. He now weights leadership quality far more heavily, assessing CEOs not by interviews or charisma, but by their verifiable track record and through trusted backchannel references who have worked with them directly.

To elicit candid answers from fund managers, the most effective technique is not the question itself but the silence that follows. Resisting the psychological urge to fill the space forces the manager to sit with the question, often leading to less rehearsed and more truthful responses.

The most driven entrepreneurs are often fueled by foundational traumas. Understanding a founder's past struggles—losing family wealth or social slights—provides deep insight into their intensity, work ethic, and resilience. It's a powerful, empathetic tool for diligence beyond the balance sheet.