Investors probe the origin of the first few customers. Hearing about crashing trade shows or intercepting people at coffee demonstrates a founder's determination and ability to get things done without a large budget or existing brand.

To get past a founder's polished pitch, ask about their core motivations (like ambition) multiple times throughout the diligence process, using different phrasing. This repeated, layered approach can reveal inconsistencies and expose their genuine life goals versus what they think investors want to hear.

Employees at large companies who independently work nights and weekends on projects outside the roadmap, driven by customer obsession, are exhibiting the key traits of a founder. This behavior, while potentially disruptive to their team, signals a strong, innate entrepreneurial drive ready to be unleashed.

A compressed diligence process relies heavily on projections. A superior approach is building a relationship over 1-2 years, which allows an investor to witness the company's actual execution against its stated goals, providing far greater conviction than any financial model.

VCs with operational backgrounds value execution over credentials. They screen for founders who show an instinct to act and build immediately, such as launching a splash page to test demand, before raising capital. This "dirt under the fingernails" is a stronger signal than pedigree.

Move beyond slide decks to gauge a founder's true passion and product quality. By installing and using a product live during a pitch, investors can ask deep, contextual questions and observe the founder's unscripted responses, revealing a level of genuineness a presentation cannot.

To gauge a founder's drive and potential for greatness, ask if they have ever been in the top 1% of any field, even an esoteric one. This unconventional question serves as a powerful proxy for ambition and the willingness to push through challenges, regardless of their professional background.

Ask a founder what they'd do on a Monday morning after they've made a billion dollars and fulfilled all their fantasies. This thought experiment strips away financial incentives and reveals their core drive. An inability to answer suggests they haven't thought beyond the exit.

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.