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Brett Taylor

From building Google Maps to leading OpenAI’s board, a career of innovation and leadership

Bret Taylor is one of the most accomplished leaders in tech, with a career spanning roles as co-CEO of Salesforce, CTO of Meta, chairman of OpenAI’s board, and co-creator of both Google Maps and the Facebook Like button. A three-time founder (including FriendFeed and Quip), he is now CEO of Sierra, an AI agent company transforming customer service. Taylor has succeeded at every level, from engineer to C-suite, and across disciplines including PM, engineering, product, operations, and executive leadership.

Episodes (1)

Insights (9)

Google Local Failure Led to Google Maps Success

case studies lessons

Google Local copied yellow pages and flopped despite homepage traffic, leading Brett to pivot to Google Maps which drew 10 million first-day users and reshaped mapping.

4m

Three AI Market Segments: Avoid Foundation Models

strategic thinking

Brett outlines frontier models, tooling, and applied-AI agents as the three meaningful markets, warning startups to avoid capex-heavy foundation models.

52m

Outcome-Based Pricing Aligns Vendors as Partners

leadership perspectives

Brett argues outcome-based contracts turn software sellers into genuine partners because revenue depends on delivering the customer’s goal.

1h 5m

Sierra's Outcome-Based Pricing Model

growth scaling tactics

Sierra earns a set fee for each AI-resolved call, directly tying revenue to the $10-$20 cost a customer avoids per deflection.

1h 4m

Building Things to Predict the Future

leadership perspectives

Brett says he lives by Alan Kay’s idea that building things yourself is the surest way to shape what comes next.

1h 25m

Agent Is New App

strategic thinking

He states that "agent is the new app", forecasting agent companies will evolve like SaaS and win by workflow value rather than model tech.

55m

Like Button Origins: Clearing One-Word Comments

case studies lessons

To clear one-word replies on Friendfeed, Brett introduced a neutral one-click ‘Like’ after rejecting a heart icon so discussions could focus on substantive comments.

1h 25m

Choose Go-to-Market Model Based on Buyer Behavior

strategic thinking

Brett outlines developer-led, product-led growth, and direct sales models and urges teams to pick the one that matches how their buyers evaluate and purchase software.

1h 17m

Agents Will Drive Next Major Productivity Wave

leadership perspectives

He believes fully autonomous agents will spark economy-wide productivity gains similar to the 1990s ERP revolution.

59m