During a pitch, if you ask about a perceived weakness and a co-founder other than the CEO confidently takes the question, it's a strong positive signal. It shows the team has self-awareness and leverages individual strengths effectively.

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.

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.

An investor can gauge a founder's depth by their preparedness. If a VC's questions during a 60-minute pitch reveal strategic holes the founder hasn't already considered, it's a strong negative signal about their level of obsession and foresight.

The best founders, especially in complex fields, don't give superficial answers to secure funding. Instead, they demonstrate deep passion and expertise by enthusiastically pulling investors into the intricate details and underlying principles of their domain.

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.

Draper filters founders by asking, "Why are you doing this?" He looks for a deeply personal, obsessive drive to solve a problem—a mission that "bursts out of their chest." This raw passion, rather than a desire for money, is his key indicator of a founder who will succeed against all odds.

To truly understand a founder, Katelin Holloway bypasses typical pitch questions. She engaged one founder in a conversation about wormholes and the time-space continuum. This abstract dialogue revealed how his brain worked and his core values, giving her conviction in him as a person, not just his idea.

Great founders turn a pitch into a collaborative discussion by asking investors to identify business weaknesses. This signals curiosity, strength, and a desire for genuine feedback over just presenting a perfect picture. It demonstrates a coachable leader who is focused on gathering data to improve.