Investors should view a founder's desire to learn skills like etiquette not as a weakness, but as a strong positive signal. It demonstrates humility, introspection, and a drive for self-improvement—key traits for a coachable and successful leader. The capacity for growth can be more valuable than pre-existing polish, identifying them as better long-term partners.

Chaddha's process prioritizes deep relationship-building over transactional speed. He requires at least 10 hours of interaction, including dinners, to gauge a founder's character, respect, and long-term partnership potential, filtering out those just seeking quick money.

To predict the future health of a partnership, intentionally have difficult conversations before any investment is made. If you can't productively disagree or discuss serious problems before you're formally linked, it's highly unlikely you'll be able to do so when the stakes are higher post-investment.

Formal cultural diligence can be staged. A more authentic assessment comes from informal settings. Observing how a target CEO and their team treat service staff reveals their true character and provides a powerful, unfiltered indicator of cultural compatibility or potential red flags for integration.

People are practiced and guarded during formal meetings. To understand their true nature, Negreanu suggests engaging with them in informal environments like a meal or drinks. This disarms them, making their reactions more authentic and revealing.

Beyond table stakes like hunger and vision, the most successful founders exhibit deep empathy ("people gene"), curiosity, and high emotional intelligence. They are secure, know their weaknesses, and often have a background in team sports, understanding that company building is a team effort.

A rising tide lifts all boats. The true test of a founder partnership emerges during downturns. Diligence should focus on teasing out traits like adaptability, humility, and accountability, which predict how a founder will react when plans inevitably go awry.

Interviews can be misleading as founders are skilled at presenting well. Venture investor Naveen Chaddha relies heavily on extensive back-channel references to create an "X-ray" of a founder's history. He believes that while founders can craft a narrative, they cannot hide from their past actions and reputation.

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.