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He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor (Sierra)

He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor (Sierra)

38 segments available

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 *Transcript:* https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/168905359/my-biggest-takeaways-from-this-conversation *Where to find Bret Taylor:* • X: https://x.com/btaylor • LinkedIn: https://www.linkedin.com/in/brettaylor/ *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/ ...References continued at: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor _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.

Segments Timeline

1
0:00 - 0:41
0:41 duration183 words

The Shift to AI Agents

Bret Taylor discusses the future of the AI market, emphasizing a shift towards agents and outcomes-based pricing. He reflects on the challenges of selling productivity software and shares a personal story about a significant mistake during his early career at Google, which ultimately led to the creation of Google Maps. This segment highlights the importance of learning from failures and adapting to market needs.

"You're CTO of Meta. You  are a co-CEO of Salesforce,   you're chairman of the board at OpenAI. How do  you think the AI market is going to play out? The whole market is going to go towards agents.  I ..."

2
0:41 - 1:55
1:13 duration255 words

From Failure to Google Maps

In this segment, Bret Taylor recounts his early career at Google, where he faced a tough product review for Google Local. He shares how this experience shaped his approach to product development and led to the creation of Google Maps, which gained 10 million users on its first day. This story illustrates the power of resilience and innovation in overcoming setbacks.

"They gave me another shot to do the V2  of it that resulted in Google Maps. We   got about 10 million people  using it on the first day. What mindset contributed to you being  successful in such a var..."

3
1:55 - 2:22
0:27 duration96 words

The Mindset of Impact

Bret Taylor reveals the mindset that has driven his success across various roles, inspired by a lesson from Sheryl Sandberg. He emphasizes the importance of asking, 'What is the most impactful thing I can do today?' This segment explores how reframing his approach to leadership and focusing on impact transformed his career and decision-making process.

"conversation with a legendary builder. If you enjoy this podcast, don't forget   to subscribe and follow it in your favorite  podcasting app or YouTube. Also, if you become   an annual subscriber of m..."

4
2:22 - 4:10
1:47 duration286 words

The Power of Diverse Roles

Bret Taylor reflects on his diverse career, having held multiple roles from engineer to CTO and CEO. He discusses the value of flexibility in identity and how it has contributed to his success. This segment highlights the importance of adapting to the needs of a company and the various skills required to thrive in different positions within the tech industry.

"This episode is brought to you by CodeRabbit,  the AI code review platform transforming how   engineering teams ship faster with AI without  sacrificing code quality. Code reviews are   critical, but ..."

5
4:10 - 5:07
0:56 duration213 words

Learning from Management Challenges

In this segment, Bret shares a pivotal moment in his management career at Facebook, where he received direct feedback from Sheryl Sandberg. He discusses how this feedback helped him realize the importance of aligning his focus with the needs of his team and the organization, ultimately leading to greater success and fulfillment in his role.

"Bret, thank you so much for being  here and welcome to the podcast. Thanks for having me. My pleasure. There's so much that I want to  talk about. You've done so many incredible   things over the cour..."

6
16:01 - 18:57
2:56 duration523 words

The Power of Impactful Leadership

Bret Taylor shares a pivotal moment in his career when Sheryl Sandberg challenged him to raise his management standards. This conversation led him to shift his focus from personal interests to the most impactful actions he could take as a leader. He emphasizes the importance of self-reflection and adapting to the needs of the organization, ultimately finding joy in driving success through impact rather than just engineering or product design.

"I ended up with a very large group, 100 under  me and I was essentially running our platform   and mobile groups, products, design engineering. So I went from a handful of reports to, I don't   know, ..."

7
18:57 - 20:01
1:03 duration188 words

A Transformative Question

Bret discusses the transformative question he began asking himself daily: 'What is the most impactful thing I can do today?' This heuristic not only guided his actions but also opened him up to tasks he previously avoided, leading to greater job satisfaction and effectiveness. He credits Sheryl Sandberg for instilling this mindset, which has become a cornerstone of his approach to leadership.

"in the broadest sets of the words saying, "What  is the most impactful thing I can do today?" And   really thinking almost like, if you had an  external board of advisors telling you what   are the th..."

8
20:01 - 22:06
2:04 duration393 words

The Dangers of Incorrect Storytelling

In this segment, Bret warns about the pitfalls of incorrect storytelling in product management. He explains how misinterpreting customer feedback can lead to misguided strategies and ultimately, business failure. He stresses the importance of intellectual honesty and understanding the true reasons behind customer decisions, rather than relying on surface-level explanations.

"Yeah. My biggest takeaway from this, which  is this question of what is the most   impactful thing I could do today? Such a powerful  heuristic just to keep in mind. To your point,   you may realize y..."

9
22:06 - 23:41
1:35 duration316 words

Self-Awareness in Problem Solving

Bret highlights the need for self-awareness among founders and product managers, particularly regarding their strengths and biases. He discusses how individuals often default to solutions that align with their expertise, which may not always be the best approach. This segment emphasizes the importance of questioning one's instincts and seeking diverse perspectives to address challenges effectively.

"And so, I think one of the things I've observed  with first time founders in particular is you're   often a single issue voter based on your skillset. So if you're a great engineer, the answer to   al..."

10
23:41 - 28:26
4:44 duration943 words

Learning from Failure: The Frontier Experience

Bret recounts his experience with Frontier, his first company, where despite having a talented team, they struggled to compete with Twitter. He reflects on the lessons learned from this failure, particularly the importance of market awareness and seeking external advice. This story illustrates the challenges of product development and the necessity of understanding distribution and market dynamics.

"they'll lie to themselves more often than  not. And it's a very challenging question   to answer. The question's interesting. Being able  to answer it accurately is actually the hard part. This feels ..."

11
28:26 - 30:24
1:58 duration364 words

Evaluating Advice: A Critical Skill

In this segment, Bret discusses the complexities of evaluating advice from others. He emphasizes the need for good judgment and understanding the context behind advice given. By asking 'why' and seeking to understand the reasoning behind suggestions, individuals can develop a nuanced approach to decision-making, rather than blindly following rules based on anecdotal experiences.

"Any heuristics or advice for people to  know whose advice to listen to? What do   you pay attention to when you're like, okay,  ignore this person but listen to this person? Yeah, that one's tough. It..."

12
30:24 - 33:40
3:15 duration586 words

The Future of Coding and Systems Thinking

Bret shares his perspective on the future of coding, emphasizing the importance of studying computer science beyond just learning to code. He argues that understanding systems thinking and the principles behind algorithms is crucial as software development evolves. This segment highlights the role of AI in transforming how software is created and the need for a strong foundational knowledge in technology.

"I think one is, it does come down to good  judgment, I think. I don't know how to teach that.  I'm a huge believer in good judgment. It's  one of the things I hire for. I just think   that's something..."

13
34:52 - 36:24
1:32 duration306 words

Designing for Reality: The Newsfeed Example

Taylor reflects on the challenges of designing Facebook's newsfeed, illustrating how real-world data often deviates from idealized designs. He emphasizes the need for systems that can handle messy inputs and create delightful user experiences, showcasing the importance of realistic design processes in product development.

"I am sure it's changed a lot since I left in  2012, but we made a system so designers had   to show their newsfeed designs with real  newsfeed data that was messy rather than   anything artificial bec..."

14
36:24 - 37:53
1:28 duration299 words

The Evolution of Programming Languages

In this segment, Taylor explores the historical progression of programming languages and the potential need for new systems designed for AI interaction. He argues that as coding becomes less about manual input and more about managing AI-generated code, the focus should shift to ensuring reliability and safety in software development.

"idea that you shouldn't study these disciplines,  it's like people say, I don't want to study math   because I'm not going to use it in my career for  X. Well, studying maths is quite important. It   ..."

15
37:53 - 39:46
1:53 duration297 words

Redefining Code Quality in an AI World

Taylor discusses the implications of AI-generated code on programming practices, advocating for a shift in how we evaluate code quality. He suggests that as the cost of writing code approaches zero, the focus should be on creating robust systems that ensure safety and reliability, rather than on the ergonomics of programming languages.

"operating systems and time-sharing systems from  the invention of things like Unix at Bell Labs and   Berkeley, you ended up with the C programming  language, Fortran and a lot of higher level   progr..."

16
39:46 - 41:36
1:49 duration372 words

Leveraging AI for Complex Software Development

Taylor envisions a future where AI assists in developing complex software systems, emphasizing the need for new programming paradigms that prioritize efficiency and safety. He highlights the potential for AI to supervise code generation and improve the robustness of software, paving the way for more agile development processes.

"just because it's one of the most inefficient  programming languages of all time. If you know   the global interpreter lock and just slow. And  I've written a lot of high-scale web services and   it's..."

17
41:36 - 43:42
2:06 duration399 words

The Matrix of Software Development

In a visionary discussion, Taylor likens the future of coding to a 'Matrix-like' experience, where developers operate advanced code-generating systems. He expresses excitement about the possibilities this presents for creating complex software quickly and efficiently, while ensuring that the systems are robust and reliable.

"And so, the question is how do you enable humans  to have as much leverage as possible? Which means   using computers to do the work on your behalf. You  could have obviously the simplest form of this..."

18
43:42 - 45:10
1:28 duration279 words

Vanta: Automating Compliance

Taylor introduces Vanta, a company focused on helping businesses automate their security compliance processes. He discusses how Vanta supports startups in building trust through efficient compliance solutions, highlighting the importance of security in today's digital landscape.

"I feel like we're definitely living in the  future when someone like you is suggesting   that we build a matrix like experience and  that's going to be potentially the future   of coding and building...."

19
45:10 - 51:02
5:51 duration1041 words

Preparing Kids for an AI-Driven Future

Taylor shares insights on how he is preparing his children for a future dominated by AI. He emphasizes the importance of integrating AI into their learning processes and discusses the challenges educators face in adapting to new technologies. He believes that AI can democratize education and enhance learning experiences for all students.

"We appreciate you for doing  that. And you have a special   discount for listeners. They can get  $1,000 off Vanta at vanta.com/lenny.   That's V-A-N-T-A .com/lenny for $1,000  off Vanta. Thanks for t..."

20
50:44 - 52:06
1:21 duration292 words

Navigating Technology in Education

In this segment, Bret Taylor reflects on the challenges of integrating AI into education. He compares AI tools to traditional technologies like graphing calculators, emphasizing the need for adaptation in teaching methods. Taylor advocates for a thoughtful approach to introducing AI to children, distinguishing it from mobile devices, and viewing it as a utility for learning rather than a distraction.

"agency and I think that's very exciting. I'm  hopeful that there's a 11-year-old right now   who's going to start a really amazing company  10 years from now whose ChatGPT is going to   be their prima..."

21
52:06 - 53:36
1:30 duration304 words

AI Market Segmentation Insights

Bret Taylor shares his insights on the AI market, identifying three key segments: frontier models, tooling, and applied AI. He warns against startups attempting to build frontier models due to high capital requirements and consolidation risks. Taylor emphasizes the importance of focusing on applied AI, particularly in creating agents that enhance customer service and experience.

"I'm going to zoom out and let's talk about  business strategy AI. One of the biggest questions   a lot of founders think about these days is just  where should I build? What will foundational model   ..."

22
53:36 - 55:02
1:26 duration268 words

The Future of AI Tooling

In this segment, Bret discusses the tooling market within AI, likening it to the Gold Rush where companies provide essential services like data labeling and evaluation tools. He cautions that many tooling companies are at risk of being overshadowed by major infrastructure providers. Taylor highlights the need for differentiation and the potential for meaningful companies to emerge despite these challenges.

"a return on the investment for a model that  deteriorates in value so quickly. So, I think   that's going to end up probably no entrepreneur  should build a frontier model. That's my take. Unless you'..."

23
55:02 - 56:34
1:31 duration280 words

The Rise of AI Agents

Bret Taylor explains the significance of AI agents as the new product form factor in the software industry. He discusses how companies like Sierra are developing agents for customer service and other applications. Taylor predicts that as building agents becomes easier, a wave of new companies will emerge, similar to the evolution of SaaS, focusing on delivering business outcomes rather than just technological capabilities.

"and others, but there's a lot of others that were  obviated by technology from the infrastructure   providers themselves. So those companies probably  are the most at risk for a developer day from one..."

24
56:34 - 58:07
1:32 duration305 words

Transforming Productivity with AI

In this segment, Bret reflects on the transformative potential of AI agents in driving productivity. He compares the impact of AI on jobs to historical shifts in the workforce, such as the elimination of draftspeople in engineering. Taylor argues that AI will enable smaller teams to accomplish more, fundamentally changing how businesses operate and measure productivity.

"market for them will be probably less technical. If you think about the purest form of software as   a service, it's not like you ask what database  do you use? It's really about the feature and   fun..."

25
58:07 - 1:04:02
5:55 duration1051 words

Outcome-Based Pricing in AI

Bret Taylor discusses the concept of outcome-based pricing for AI products, using Sierra as an example. He explains how this pricing model aligns the interests of AI providers with their customers by focusing on measurable outcomes rather than usage metrics. Taylor emphasizes the importance of being customer-centric and how this approach can redefine the software industry, making it more effective and transparent.

"other two markets. I'm particularly excited as  building agents becomes easier, to see a lot of   long tail agent companies come out. I was looking  at a website for the top 50 software companies in  ..."

26
1:05:32 - 1:06:43
1:10 duration220 words

Outcome-Based Pricing in AI

Bret Taylor discusses the innovative outcome-based pricing model at Sierra, emphasizing how AI agents can resolve customer issues without human intervention. He explains the concept of call deflection and how aligning business models with customer needs can lead to measurable outcomes, contrasting it with traditional usage-based pricing that often fails to reflect true value.

"So if an AI agent can take that call and solve  it, that is in the industry often called a call   deflection or a containment. And that essentially  means you saved, call it $15 because you didn't   h..."

27
1:06:43 - 1:08:43
2:00 duration385 words

The Flaws of Usage-Based Pricing

In this segment, Bret critiques the common practice of usage-based pricing in AI, using the analogy of coding productivity metrics. He argues that measuring success by tokens or lines of code can be misleading and emphasizes the importance of focusing on outcomes rather than mere usage, advocating for a customer-centric approach in the software industry.

"popular particularly in the infrastructure  space is closer to it. But I'm not sure a   token is actually a good measure of value from AI  either. I always use the analogy, like right now,   most of t..."

28
1:08:43 - 1:10:50
2:06 duration404 words

Improving AI Productivity Through Root Cause Analysis

Bret shares insights on enhancing AI productivity by implementing root cause analysis for coding errors. He highlights the importance of context in AI-generated code and discusses how Sierra is developing systems to ensure AI agents learn from mistakes, ultimately leading to improved performance and customer satisfaction.

"We've been chatting a little  bit about productivity gains.   There's a lot of skepticism in the headlines  these days of just like what is AI actually   doing? Is it actually helping people be more  ..."

29
1:10:50 - 1:12:56
2:06 duration395 words

Creating a Virtuous Cycle of Improvement

In this segment, Bret elaborates on how Sierra enables clients to create a virtuous cycle of improvement in customer service interactions. He explains the diverse applications of their AI agents across various industries and the significant automation rates achieved, showcasing the potential for high customer satisfaction through effective AI integration.

"the AI is actually very effective. Just think  about it this way, if you produce an AI agent   that's right 90% of the time, that's not that  great, but how hard would it be to make another   AI agent..."

30
1:12:56 - 1:14:06
1:10 duration240 words

The Future of Customer Interactions

Bret envisions a future where every customer interaction is instant, personalized, and multilingual, facilitated by AI agents. He reflects on the transformative potential of AI in customer service, aiming to replicate the personal touch of human interactions at scale, and discusses the implications for businesses and customer relationships.

"And so, for customers using platforms like Sierra,  yeah, AI agents aren't perfect, but we're creating   a system that lets customers create a virtuous  cycle of improvement. If you want to go from a ..."

31
1:14:06 - 1:15:55
1:48 duration318 words

Go-To-Market Strategies for AI Products

Bret shares valuable insights on effective go-to-market strategies for AI products, emphasizing the importance of understanding the buyer's journey. He discusses different models such as developer-led growth and product-led growth, and highlights the resurgence of direct sales in the AI sector, urging founders to align their strategies with the purchasing processes of their target markets.

"Got it. That is very cool. I hadn't heard of  people doing that, model context protocol,   makes sense. We've talked about productivity gains  outside TX. Just to give you a chance to share   how amaz..."

32
1:15:55 - 1:21:36
5:40 duration1031 words

Navigating Sales Challenges in AI

In this segment, Bret addresses the challenges many AI founders face in sales, particularly those without a business background. He stresses the necessity of mastering sales techniques and understanding the dynamics between users and buyers, advocating for a thoughtful approach to go-to-market strategies that can lead to successful AI product adoption.

"do so with really high customer satisfaction  scores. That Weight Watchers agent, I believe   has a customer satisfaction score of 4.6 out  of five, which is pretty amazing. And what's   interesting a..."

33
1:21:53 - 1:23:08
1:14 duration229 words

Books That Shape Success

Bret Taylor shares his top book recommendations that have influenced his career, including 'Competing Against Luck' by Clayton Christensen, which introduces the Jobs to be Done framework. He also highlights 'Endurance,' the gripping true story of Shackleton's expedition, emphasizing its lessons on grit and resilience for entrepreneurs facing challenges.

"Yeah, go ahead. What are two or three books that you find  yourself recommending most to other people? I don't read a lot of nonfiction, but probably  if I had to pick one in the area of the topics   ..."

34
1:23:10 - 1:24:39
1:28 duration294 words

Inception: A Movie Worth Discussing

Bret discusses his recent viewing of 'Inception' with his kids, praising Christopher Nolan's storytelling that sparks deep conversations. He reflects on the film's complexity and its ability to engage viewers long after watching, showcasing the impact of thought-provoking cinema.

"expectations for folks that  joined that famous newspaper- That ad. That newspaper ad. I don't know if  that's true. It's remarkable if that's true. Oh, it might not be true. I don't know. The interne..."

35
1:24:39 - 1:25:00
0:20 duration96 words

Cursor: The Future of Software Creation

Bret expresses his enthusiasm for Cursor, an AI tool that has transformed his software creation process. He discusses how this product aligns with his passion for building and creating, highlighting its potential as a transitional product in the evolving landscape of AI.

"I think that's the first time someone's  actually mentioned Cursor in this answer,   so might be the beginning of a trend. Michael  Trell was on the podcast and he actually   had a very similar messag..."

36
1:25:00 - 1:25:27
0:26 duration84 words

Inventing the Future: A Life Motto

Bret shares his favorite life motto, 'The best way to predict the future is to invent it,' attributed to Alan Kay. He reflects on how this philosophy drives his entrepreneurial spirit and his commitment to building innovative solutions.

"life motto that you often come back  to and find useful in work or in life? The best way to predict the future is to  invent it, which I think I attribute to Alan   Kay of Xerox PARC. He invented a lo..."

37
1:25:27 - 1:27:36
2:09 duration368 words

The Story Behind the 'Like' Button

Bret recounts the origins of the 'Like' button at FriendFeed, explaining the initial concept of a one-click comment feature. He discusses the challenges of choosing the right sentiment for the button and how it evolved to become a neutral yet positive acknowledgment, solving the problem of cluttered discussions.

"I feel like many people say this, I  feel like you've actually done this   so many times. You're really living this  motto. Final question. We talked about you   inventing the like button at FriendFee..."

38
1:27:36 - 1:28:30
0:53 duration196 words

Connecting with Bret Taylor

In the closing moments, Bret shares how listeners can connect with him and learn more about Sierra, his AI agent company. He invites those interested in customer service solutions or job opportunities to reach out, emphasizing the importance of trying out Sierra's offerings.

"Wow. I've never heard the story  before. It makes me think about   LinkedIn now. They're basically trying  to solve that same problem. They have   all these auto-reply pill tag things. I  don't think ..."