Founders can accurately gauge an investor's future helpfulness by their actions during the pre-investment courtship phase. If an investor is unwilling to provide value when they are most motivated to win the deal, they are unlikely to be a helpful partner later on.

To truly understand a potential financial partner, the Chomps team went beyond the supplied references. They found a founder whose company didn't succeed under the PE firm's investment. His positive review of the partner's character, despite the negative outcome, provided the most powerful signal of trust.

David Cohen of Techstars advises founders to request references from a VC's failed investments. This reveals how an investor behaves during difficult times, providing a more honest assessment of their character and support level than speaking only with successful founders.

An investor's best career P&L winners are not immediate yeses. They often involve an initial pass by either the investor or the company. This shows that timing and building relationships over multiple rounds can be more crucial than a single early-stage decision, as a 'missed round' isn't a 'missed company'.

YC now provides founders an investor's conversion rate (meetings vs. checks). A low rate signals to founders not to prioritize that meeting, forcing VCs to abandon a "catch-all" meeting approach in favor of being highly selective upfront to avoid damaging their reputation within the ecosystem.

Limited Partners (LPs) value fund managers who are willing to listen and internalize market feedback, even if they ultimately follow their own strategy. This openness is a key positive signal, while a refusal to listen is a major red flag that often appears early in the relationship.

The strongest signal a VC can receive is when a founder they've backed asks to become a Limited Partner, especially after an exit. It proves the VC's value far exceeded the capital provided, demonstrating deep trust and authentic partnership.

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.

The most potent source of new, truly cutting-edge investment opportunities isn't inbound emails or demo days, but rather the networks of the exceptional founders and scientists you've already backed. These individuals are at the frontier and can identify the next wave of talent.