
He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more
🤖 AI Summary
Overview
This episode features Bret Taylor, a tech industry legend whose career spans co-creating Google Maps, inventing the Like button, leading as CTO of Meta, co-CEO of Salesforce, and chairing OpenAI. Now the founder of Sierra, an AI agent company, Bret shares insights on his career, the future of AI, and lessons learned from both failures and successes. Topics include the transformative potential of AI agents, the evolution of coding, outcome-based pricing, and strategies for navigating the AI market.
Notable Quotes
- The whole market is going to go towards agents. I think the whole market is going to go towards outcomes-based pricing. It's just so obviously the correct way to build and sell software.
— Bret Taylor, on the future of software.
- The best way to predict the future is to invent it.
— Bret Taylor, quoting Alan Kay, reflecting his entrepreneurial ethos.
- If you think the thing you've been doing your whole career is the way to fix your problem, it's at least 30% likely you've chosen that because of comfort and familiarity, not truth.
— Bret Taylor, on avoiding bias in problem-solving.
🗺️ The Creation of Google Maps and Lessons from Failure
- Bret shared how his early failure with Google Local, a lackluster product, taught him the importance of differentiation and innovation.
- This failure led to the creation of Google Maps, which redefined mapping by integrating local search, driving directions, and satellite imagery.
- Key lesson: Avoid simply digitizing existing solutions; instead, create entirely new experiences native to the platform.
🧠 Mindsets for Success Across Roles
- Bret credits Sheryl Sandberg for teaching him to ask daily, What is the most impactful thing I can do today?
This mindset transformed his approach to leadership.
- He emphasized the importance of flexibility in identity, adapting to what the company or role needs at any given time.
- Founders and leaders should avoid defaulting to their comfort zones and instead focus on intellectual honesty and diverse perspectives.
🤖 The Future of AI and Agents
- Bret predicts AI agents will replace traditional SaaS products, enabling businesses to achieve autonomous outcomes.
- He outlined three key AI market segments:
1. Foundation Models: Dominated by hyperscalers due to high capital requirements.
2. Tooling: Risky but valuable for specialized needs like data labeling and evaluation tools.
3. Applied AI (Agents): High-margin opportunities where agents autonomously solve business problems.
- He believes agents will drive measurable productivity gains, akin to the transformative impact of early computing.
💸 Outcome-Based Pricing in AI
- Sierra’s pricing model charges customers based on outcomes, such as resolving customer service issues, rather than usage.
- This approach aligns vendor and customer goals, ensuring measurable value.
- Bret contrasted this with usage-based pricing, which can misalign incentives and fail to reflect true value.
📚 Coding, Systems Thinking, and Education in the AI Era
- Bret advocates for learning computer science to develop systems thinking, even as AI transforms how code is written.
- He envisions a future where coding involves operating code-generating machines, requiring a deep understanding of systems rather than syntax.
- For children, he encourages integrating AI tools like ChatGPT into learning, emphasizing their potential as personalized tutors.
AI-generated content may not be accurate or complete and should not be relied upon as a sole source of truth.
📋 Episode Description
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
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Where to find Bret Taylor:
• 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/
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In this episode, we cover:
(00:00) Introduction to Bret Taylor
(04:10) Bret’s early career and first major mistake