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He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more

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Jul 31, 2025

Guest

Bret Taylor

Bret Taylor, co-founder and CEO of Sierra, has a storied tech career including roles as CTO of Meta and co-CEO of Salesforce. He shares how a critical product review almost derailed his Google career, leading to the creation of Google Maps. Taylor discusses transformative AI agents poised to replace traditional SaaS products, innovative outcome-based pricing models, and lessons from early career missteps. He also reflects on the importance of coding skills in an AI-driven future and the vital question he learned from Sheryl Sandberg that maximizes daily impact.

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Episode notes

00:00 / 00:00

From Failure to Google Maps

Bret Taylor's early Google Local product was a disappointed attempt to digitize Yellow Pages.
This failure led to the creation of Google Maps, which launched with 10 million users on day one, revolutionizing local search.

00:00 / 00:00

Flexible Roles and Daily Impact

Adopt a flexible identity and embrace roles required by your company's stage.
Follow Sheryl Sandberg's advice: each morning ask, "What’s the most impactful thing I can do today?"

00:00 / 00:00

Question Your Product Assumptions

Question commonly accepted reasons for your product's failures to avoid false narratives.
Seek diverse perspectives and honest feedback to ensure you address the real problem.

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Lessons from Product Management Challenges

04:16 • 27min

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The Future of Coding in an AI World

31:26 • 12min

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Innovative Security Solutions for Modern Businesses

43:42 • 2min

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AI in Education and Business: Transformative Potential

45:27 • 28min

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Enhancing AI-Customer Interactions Through Context and Automation

01:13:28 • 4min

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Navigating GTM Strategies for AI Founders

01:17:03 • 8min

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Inventing the Future: Innovation and the Story Behind the 'Like' Button

01:24:40 • 4min

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#3655

• Mentioned in 7 episodes

Competing Against Luck

Clayton M. Christensen

David S. Duncan

Taddy Hall

Karen Dillon

In 'Competing Against Luck,' Clayton Christensen and co-authors introduce the 'Jobs to Be Done' theory, which posits that customers 'hire' products to solve specific problems. The book provides real-world examples and tools for entrepreneurs to innovate effectively and create products that customers are willing to pay premium prices for. It offers insights into how companies like Uber and Airbnb have successfully applied this approach.

#453

• Mentioned in 38 episodes

Endurance

Shackleton's Incredible Voyage

Alfred Lansing

This book details the almost two-year struggle for survival of the 28-man crew of the Endurance, which was beset and eventually crushed by ice floes in the Weddell Sea during the Imperial Trans-Antarctic Expedition of 1914-1917. The crew drifted on ice floes, salvaged lifeboats, and eventually reached Elephant Island. Shackleton then led a perilous journey to South Georgia Island to secure rescue, culminating in one of the most remarkable survival stories in history. Lansing's narrative is based on extensive research, including interviews with surviving crew members and access to their diaries and personal accounts.

Bret Taylor’s legendary career includes being CTO of Meta, co-CEO of Salesforce, chairman of the board at OpenAI (yes, during that drama), co-creating both Google Maps and the Like button, and founding three companies. Today he’s the founder and CEO of Sierra, an AI agent company transforming customer service. He’s one of the few people I’ve met who’s been wildly successful at every level—from engineer to C-suite executive to founder—and across almost every discipline, including PM, engineer, CTO, COO, CPO, CEO, and board member.

In this conversation, you’ll learn:

1. The brutal product review that nearly ended his Google career—and how that failure led to creating Google Maps

2. The question Sheryl Sandberg taught him to ask every morning (“What’s the most impactful thing I can do today?”) that transformed how he approached every role

3. The three AI market segments that matter

4. Why AI agents will replace SaaS products

5. His framework for knowing whose advice to actually listen to—and how that came in handy during the OpenAI board drama

6. The counterintuitive go-to-market strategy most AI startups get wrong

7. Sierra’s outcome-based pricing model that’s transforming how enterprise software is sold (and why every SaaS company should adopt it)

8. What he’s teaching his kids about AI that every parent should know

—

Brought to you by:

CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny

Basecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lenny

Vanta—Automate compliance. Simplify security: https://vanta.com/lenny

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Transcript: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor

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My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168905359/my-biggest-takeaways-from-this-conversation

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Where to find Bret Taylor:

• X: https://x.com/btaylor

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

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Bret Taylor

(04:10) Bret’s early career and first major mistake

(08:24) The birth of Google Maps

(11:57) Lessons from FriendFeed and the importance of honest feedback

(31:30) The future of coding and AI’s role

(45:26) Preparing the next generation for an AI-driven world

(48:46) AI in education

(52:05) Business strategies in the AI market

(01:04:38) Outcome-based pricing in AI

(01:09:15) Productivity gains and AI

(01:17:35) Go-to-market strategies for AI products

(01:21:49) Lightning round and final thoughts

—

Referenced:

• Marissa Mayer on LinkedIn: https://www.linkedin.com/in/marissamayer/

• “Lazy Sunday”—SNL: https://www.youtube.com/watch?v=sRhTeaa_B98

• Quip: https://quip.com/

• Sierra: https://sierra.ai/

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

• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/

• Jim Norris on LinkedIn: https://www.linkedin.com/in/halfspin/

• Paul Buchheit on X: https://x.com/paultoo

• Sanjeev Singh on LinkedIn: https://www.linkedin.com/in/sanjeev-singh-20a1b72/

• Barack Obama: https://www.obamalibrary.gov/obamas/president-barack-obama

• Oprah Winfrey: https://en.wikipedia.org/wiki/Oprah_Winfrey

• Ashton Kutcher: https://en.wikipedia.org/wiki/Ashton_Kutcher

• PayPal Mafia: https://en.wikipedia.org/wiki/PayPal_Mafia

• Sam Altman on X: https://x.com/sama

• Warren Buffett on X: https://x.com/warrenbuffett

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

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

• C: https://en.wikipedia.org/wiki/C_(programming_language)

• Python: https://www.python.org/

• Perl: https://www.perl.org/

• Rust: https://www.rust-lang.org/

• Eleven Labs: https://elevenlabs.io/

• The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack

• Confluent: https://www.confluent.io/

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

• Snowflake: https://www.snowflake.com

• Harvey: https://www.harvey.ai/

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

• Larry Summers’s website: https://larrysummers.com/

• AutoCAD: https://www.autodesk.com/products/autocad/overview

• Revit: https://www.autodesk.com/products/revit/

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867

• Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://lenny.substack.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam

• Cursor: https://cursor.com/

• CodeX: https://openai.com/codex/

• Claude Code: https://www.anthropic.com/claude-code

• 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

• DirecTV: https://www.directv.com/

• SiriusXM: https://www.siriusxm.com/

• Wayfair: https://www.wayfair.com/

• Akai: https://www.akaipro.com/

• Chubbies Shorts: https://www.chubbiesshorts.com/

• Weight Watchers: https://www.weightwatchers.com/

• CLEAR: https://www.clearme.com/

• Stripe: https://stripe.com/

• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein

• Twilio: https://www.twilio.com/

• ServiceNow: https://www.servicenow.com/

• Adobe: https://www.adobe.com/

• Jobs to be done: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90

• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta

• Inception: https://www.imdb.com/title/tt1375666/

• Alan Kay’s quote: https://www.brainyquote.com/quotes/alan_kay_100831

• Jobs at Sierra: https://sierra.ai/careers

—

Recommended books:

• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867

• Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612

• Endurance: Shackleton’s Incredible Voyage: https://www.amazon.com/Endurance-Shackletons-Incredible-Alfred-Lansing/dp/0465062881

—

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.

To hear more, visit www.lennysnewsletter.com

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