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What does it really mean to give without keeping score? Brad Feld has built a career by answering that question differently than almost anyone in venture capital. In this episode of Remarkable People, Guy Kawasaki sits down with Brad to unpack the philosophy behind his new book Give First, a mindset that has shaped startup communities, mentorship culture, and long-term trust across the tech world. Brad explains why generosity isn’t naïve, why mentorship works best when it becomes a peer relationship, and how founders can build enduring success without transactional thinking. This conversation challenges many of Silicon Valley’s most sacred assumptions—and replaces them with something more human. 00:00 Effective vs. Ineffective Mentorship 00:42 Introduction to the Guest: Brad Feld 02:23 Brad Feld's Early Apple Experience 05:22 The Concept of 'Give First' 08:56 Mentorship Dynamics and Philosophy 16:47 Finding and Being a Good Mentor 26:55 Brad's Approach to Mentorship Requests 35:50 The $500 Pitch Review Experiment 36:48 The Importance of Setting Boundaries 37:22 Gatekeepers and Boundaries in Business 38:09 The 10-Slide Pitch Revolution 39:37 The Value of Donations Over Payments 42:18 The Reality of Meritocracy and Value-Added Claims 43:43 The Flaws of Pattern Matching in Entrepreneurship 46:38 Essential Characteristics of a Great Founder 51:22 Handling Disagreements with Founders 56:30 The Five Whys Technique 01:01:16 The Power of Effective Mentorship 01:03:36 A Heartfelt Conclusion and Acknowledgements #Mentorship #LeadershipSkills #ProblemSolving #StartupAdvice #Founders