In this “Lessons” episode, legendary venture capitalist Tim Guleri shares how investors can prevent misalignment with founders by performing deep personal diligence before writing a check. He reveals why surrounding first-time CEOs with experienced co-founders or advisors is essential for growth, and how ego and peer advice can often lead founders astray. By encouraging a learning mindset, filtering feedback based on experience, and building intuition through repeated exposure, Guleri outlines a clear path for both founders and investors to succeed, even when others get rejected.