Swell VC's Rusty Ralston shares that the most insightful LPs probe a GP's character, values, and personal history. For multi-decade investment relationships, understanding the person is foundational to establishing the trust, character, and integrity required for long-term success, surpassing the importance of typical fund metrics.
Answering "Why are you different?" requires deep thinking that connects strategy to operations. Han Shin of iFly explains that true differentiation is a cohesive system—his fund's thesis-driven research, concentrated portfolio, and large check sizes are all interconnected, enabling the deep, hands-on support that defines his value proposition.
The most valuable question a VC can ask a founder is, "Why are customers churning?" According to G2's Godard Abel, investigating what's not working provides the most critical insights for improvement. While founders naturally market successes, the real opportunity for growth and learning comes from understanding and addressing failures.