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

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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.

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