Ben Horowitz: Why Hesitation is a CEO’s Worst Enemy

The a16z Podcast • September 12, 2025

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In this conversation from Lenny’s Podcast, Ben Horowitz joins Lenny to discuss the psychological muscle every founder needs, why hesitation can be fatal for CEOs, when it’s time to replace a founder, and how to normalize failure while building confidence. They also explore the Databricks founding story, investing in Adam Neumann after WeWork, whether AI is in a bubble, where the real opportunities lie, and Ben’s work with the Paid in Full Foundation supporting hip-hop pioneers. The result is a candid look at leadership, product management, and what it takes to build enduring companies.

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