Why Nice Guys Win: Jules Maltz on The Power of Imperfection in Venture Capital

In the very first episode of Don’t Be a Jerk, host Healey Cypher sits down with legendary investor Jules Maltz, the VC behind investments in iconic companies like Slack, Dropbox, Grammarly, Zendesk, and more.Jules breaks every stereotype of the typical cutthroat investor. Known for his kindness and humility, Jules reveals why authenticity, vulnerability, and imperfection are strategic superpowers.In this honest and insightful conversation, you’ll discover:Why perfection can actually make people trust you less—and how embracing your imperfections deepens connections and increases likability.Powerful stories from Jules’ experiences, including how Slack’s Stewart Butterfield instantly created trust by leading with authenticity and humor instead of a traditional pitch.How Jules’ humble upbringing — from Eugene, Oregon, to feeling out of place at Yale — shaped his unique approach to business, life, and investing.Why Jules naturally chooses humility over status signaling (like driving a 2010 Prius and wearing a $20 Casio watch), and how this genuine approach has unexpectedly helped him build trust and rapport in Silicon Valley.Practical advice for founders on exactly when and how to show vulnerability to investors… without losing credibility.Insights on the crucial balance between warmth and competence—and why many entrepreneurs underestimate the power of warmth in leadership and pitches.Jules’ personal reflections and experiences, including the painful lesson of passing early on Slack and the surprising value of openly acknowledging and discussing mistakes.Why genuine authenticity is increasingly important in an AI-driven world that prioritizes polish and scripted perfection.Communication and negotiation insights, including how to remove neediness from conversations, build genuine confidence, and achieve dramatically better outcomes.Why founders who openly acknowledge challenges and imperfections often become more investable and successful in the long run.If you’re tired of superficial bravado and looking for a radically honest, thoughtful take on leadership, venture capital, and building real trust, this episode is a must-listen.Join Jules and Healey as they redefine success and reveal why kindness, humility, and authenticity might just be the most powerful competitive advantages you can have, both in business and in life.

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