When entering a new domain, don't feign expertise. Build trust faster by openly admitting "I don't know" and explicitly leaning on stakeholders for their subject matter knowledge. This positions you as a partner who values their expertise, rather than an outsider imposing solutions.

Howard Marks argues that declaring uncertainty is a sign of strength, not weakness. In important settings, saying "I don't know" signals that your ego is in check and thinking is robust. It makes people trust you more, not less, because it shows intellectual humility.

A founder must simultaneously project unwavering confidence to rally teams and investors, while privately remaining open to any evidence that they are completely wrong. This conflicting mindset is essential for navigating the uncertainty of building a startup.

True growth and access to high-level opportunities come not from feigning knowledge, but from openly admitting ignorance. This vulnerability invites mentorship and opens doors to conversations where real learning occurs, especially in complex fields like investing, which may otherwise seem like a "scam."

When a client offers harsh, fundamental criticism during a pitch, the best response is not to defend the work but to acknowledge the miss. One CEO won a pitch by immediately conceding the point and offering to re-pitch, demonstrating humility and confidence.

A founder asking an investor about their biggest blind spot during evaluation is a disarming and intelligent question. As shared by Maytha Agarwal of Defy, it forces the VC to self-audit their decision-making process in real-time, revealing their introspection and leading to a more honest, transparent conversation.

A young Ed Stack's transparent inexperience in buying meetings didn't lead to exploitation; it invited mentorship. By openly admitting what he didn't know, he transformed vendor relationships into partnerships. People were more willing to help him succeed rather than just sell to him, showing that vulnerability can be a powerful negotiation tool.

Reframe the pitch meeting from a judgment session to a mutual evaluation. Founders are selecting a partner for 7-10 years and must assess the investor for chemistry and fit, rather than just seeking capital from a position of need.

While it's crucial to listen to markets and clients, founders must also be prepared to stick to their convictions when investors, who may not be specialists in their niche, offer conflicting advice. Knowing when to listen and when to hold firm is a key startup skill.