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

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.   Timecodes:  00:00 Introduction  00:22 The Psychology of Leadership & Decision-Making 02:41 Leadership lessons from Shaka Senghor 07.56 Struggle, Pain, and Growth as a CEO  10:15 Running toward fear and why hesitation kills companies 19:35 Who shouldn’t start a company 22:36 The Databricks story: thinking bigger 24:54 Managerial leverage and CEO psychology 28:06 When founders should be replaced as CEOs 31:20 Normalizing failure for CEOs 37:57 Counterintuitive lessons about building companies 42:31 “Good Product Manager/Bad Product Manager” 48:21 Product managers as leaders 51:16 Why a16z invested in Adam Neumann after WeWork 56:23 Is AI in a bubble? 01:02:43 The biggest opportunities in AI 01:12:51 Why U.S. leadership in AI matters 01:18:53 The Paid in Full Foundation for hip-hop pioneers 01:23:18 Lightning round: book recommendations, products, and life mottos   Resources:  Find Ben on X: https://x.com/bhorowitz Find Ben on LinkedIn: https://www.linkedin.com/in/behorowitz/ Watch more of Lenny’s Podcast: https://www.youtube.com/@LennysPodcast Check out Lenny’s newsletter here: https://www.lennysnewsletter.com   Stay Updated:  Find a16z on X: https://x.com/a16z  Find a16z on LinkedIn: https://www.linkedin.com/company/a16z  Listen to the a16z Podcast on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX?si=3E8B3qT9TyiwAHJ7JnaKbg Listen to the a16z Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Follow our host: https://twitter.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures. Stay Updated: Find a16z on X Find a16z on LinkedIn Listen to the a16z Podcast on Spotify Listen to the a16z Podcast on Apple Podcasts Follow our host: https://twitter.com/eriktorenberg   Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.