Ben Orthlieb of Blue Moon considers a founder asking to invest in his fund—even after just one meeting—the highest form of validation. This rare action indicates that the VC's approach and process are so compelling that founders see the firm itself as a valuable product worth backing personally, regardless of whether their own company receives an investment.
Eric Byunn of Centana Growth advises founders to ask VCs how they would approach picking an investor if they were in the founder's position. This question is a powerful due diligence tool. Beyond providing substantive advice, the investor's response reveals their personality, approach, and ethics in navigating the inherent conflict of interest.
Foresite Capital's Jim Tananbaum values LPs who probe the firm's long-range, macro-thematic vision over short-term performance. Questions about future trends (e.g., AI in healthcare) signal an LP's alignment with a thesis-driven, forward-looking investment strategy, which he sees as the core of the business.