Jump to the best parts:

• (04:09) → Success comes from many small decisions, not one big moment: Progress comes from stacking difficult but correct choices, even when each feels insignificant on its own.

• (10:15) → Great leaders run toward fear, not away: The muscle CEOs need most is acting decisively in difficult situations, rather than hesitating in the face of equally bad options.

• (24:54) → CEOs don’t make people great—they find people who make them great: Surround yourself with world-class talent that pushes the company forward; don’t try to “fix” low performers.

Brought to you by:

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Ben Horowitz is the co-founder of Andreessen Horowitz, Silicon Valley’s largest and most influential venture capital firm, with over $46B in committed capital across multiple funds. He took Loudcloud public with just $2 million in revenue (dubbed “the IPO from hell”), sold it for $1.6 billion, and has backed companies from Facebook to Stripe to Airbnb to OpenAI to Databricks (now worth more than $100 billion). His management philosophy—forged through near-death experiences and refined through coaching hundreds of CEOs—contradicts most conventional startup wisdom.

In our conversation, Ben shares:

1. Why “founder mode” is half right and half dangerously wrong

2. The story behind “Good Product Manager/Bad Product Manager” and why it went viral despite being written in anger

3. Where the biggest AI startup opportunities remain

4. Why you need to run toward fear, never away

5. The one trait that predicts that a founder will fail as CEO

6. Inside Paid in Full, Ben’s nonprofit awarding pensions to pioneering hip-hop artists

Where to find Ben Horowitz:

• X: https://x.com/bhorowitz

• LinkedIn: https://www.linkedin.com/in/behorowitz/

• Website: https://benhorowitz.com/

• Andreessen Horowitz’s website: https://a16z.com/

In this episode, we cover:

(00:00) Introduction to Ben Horowitz

(04:09) Important leadership lessons from Shaka Senghor

(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

Referenced:

• Shaka Senghor on The Joe Rogan Experience: https://open.spotify.com/episode/79neOSawKbrxY6Tl2wV1Kx

• 1999 Martha’s Vineyard plane crash: https://en.wikipedia.org/wiki/1999_Martha%27s_Vineyard_plane_crash

• John Reed: https://en.wikipedia.org/wiki/John_S._Reed#

• LoudCrowd: https://loudcrowd.com/

• Marc Andreessen on X: https://x.com/pmarca

• Ali Ghodsi on LinkedIn: https://www.linkedin.com/in/alighodsi/

• Databricks: https://www.databricks.com/

• Ion Stoica on LinkedIn: https://www.linkedin.com/in/ionstoica/

• Hadoop: https://hadoop.apache.org/

• The Sad Truth About Developing Executives: https://a16z.com/the-sad-truth-about-developing-executives/

• Mark Zuckerberg on Facebook: https://www.facebook.com/zuck/

• Sam Altman on X: https://x.com/sama

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• Brian Chesky—Founder Mode & The Art of Hiring: https://www.youtube.com/watch?v=aFOGlNL39xs

• Bob Iger: https://en.wikipedia.org/wiki/Bob_Iger

• Larry Page: https://en.wikipedia.org/wiki/Larry_Page

• Kanye West: https://en.wikipedia.org/wiki/Kanye_West

• Diddy: https://en.wikipedia.org/wiki/Sean_Combs

• Arsalan Tavakoli on LinkedIn: https://www.linkedin.com/in/arsalantavakoli/

• Good Product Manager/Bad Product Manager: https://a16z.com/good-product-manager-bad-product-manager/

• Netscape: https://en.wikipedia.org/wiki/Netscape

• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang/

• David Weiden on LinkedIn: https://www.linkedin.com/in/davidweiden/

• Raghu Raghuram on LinkedIn: https://www.linkedin.com/in/raghuraghuram/

• Adam Neumann on X: https://en.wikipedia.org/wiki/Adam_Neumann

• WeWork: https://www.wework.com/

• Cluely: https://cluely.com/

• The Next Bubble—Don’t Get Fooled Again: https://steveblank.com/2011/06/15/the-next-bubble-dont-get-fooled-again/

• Evite: https://www.evite.com/

• Paul Krugman: https://en.wikipedia.org/wiki/Paul_Krugman

• Stargate: https://openai.com/index/announcing-the-stargate-project/

• Elon Musk on X: https://x.com/elonmusk

• Salesforce: https://www.salesforce.com/v3/

• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff

• Cursor: https://cursor.com/

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• Anthropic: https://www.anthropic.com/

• Sebastian Thrun: https://en.wikipedia.org/wiki/Sebastian_Thrun

• Waymo: https://waymo.com/

• Product lessons from Waymo | Shweta Shrivastava (Waymo, Amazon, Cisco): https://www.lennysnewsletter.com/p/product-lessons-from-waymo-shweta

• Mao Zedong: https://en.wikipedia.org/wiki/Mao_Zedong

• Pol Pot: https://en.wikipedia.org/wiki/Pol_Pot

• Nicolae Ceaușescu: https://en.wikipedia.org/wiki/Nicolae_Ceau%C8%99escu

• Joseph Stalin: https://en.wikipedia.org/wiki/Joseph_Stalin

• The Declaration of Independence: https://www.archives.gov/founding-docs/declaration-transcript

• The Constitution of the United States: https://www.archives.gov/founding-docs/constitution-transcript

• The Paid in Full Foundation: https://paidinfullfoundation.org/

• Eric B. & Rakim—“Paid in Full”: https://www.youtube.com/watch?v=E7t8eoA_1jQ

• Rakim Allah on X: https://x.com/officialrakim

• Scarface: https://en.wikipedia.org/wiki/Scarface_(rapper)

• Roxanne Shante on Instagram: https://www.instagram.com/imroxanneshante/

• Grandmaster Caz: https://en.wikipedia.org/wiki/Grandmaster_Caz

• Kool Moe Dee on Instagram: https://www.instagram.com/koolmoedeenyc/

• George Clinton’s website: https://georgeclinton.com/

• Kool G Rap’s website: https://koolgrap.com/

• Grand Puba on X: https://x.com/iamgrandpuba

• Jalil Hutchins on Instagram: https://www.instagram.com/jalil.whodini/

• The Legend of the Blind MC: https://a16z.com/the-legend-of-the-blind-mc/

• Erik Torenberg on LinkedIn: https://www.linkedin.com/in/eriktorenberg/

• Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o

• Sinners: https://www.imdb.com/title/tt31193180/

• Technivorm Moccamaster: https://www.amazon.com/Technivorm-Moccamaster-Coffee-Brewer-Polished/dp/B002S4DI2S

• Follow the Leader: https://en.wikipedia.org/wiki/Follow_the_Leader_(Eric_B._%26_Rakim_album)

• Stillmatic: https://en.wikipedia.org/wiki/Stillmatic

• One Nation Under a Groove: https://en.wikipedia.org/wiki/One_Nation_Under_a_Groove

Recommended books:

• The Hard Thing About Hard Things: Building a Business when There Are No Easy Answers: https://www.amazon.com/Hard-Thing-About-Things-Building-ebook/dp/B00DQ845EA

• How to Be Free: A Proven Guide to Escaping Life’s Hidden Prisons: https://www.amazon.com/How-Be-Free-Escaping-Prisons/dp/B0DXD5KKBF/

• The WEIRDest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous: https://www.amazon.com/WEIRDest-People-World-Psychologically-Particularly/dp/0374173222

• Writing My Wrongs: Life, Death, and Redemption in an American Prison: https://www.amazon.com/Writing-My-Wrongs-Redemption-American/dp/1101907312

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:...