Bret Taylor

Co-Founder & CEO at Sierra / Former Co-CEO Salesforce

Co-created Google Maps, co-founded FriendFeed (invented the Like button and real-time newsfeed), became CTO at Facebook, founded Quip (sold to Salesforce for $750M), became co-CEO of Salesforce, chairman of the board at OpenAI; now co-founder and CEO of Sierra, an AI agent company.

The Visionary The Operator

Dimension Profile

Strategic Vision 90%

Execution & Craft 80%

Data & Experimentation 50%

Growth & Distribution 60%

Team & Leadership 60%

User Empathy & Research 60%

Key Themes

AI agents and outcomes-based pricing serial founding and building learning from product failure daily impact prioritization productivity software challenges AI startup opportunities

Episode Summary

Bret Taylor, one of tech's most prolific builders (Google Maps, Like button, FriendFeed, Quip, Salesforce co-CEO, Sierra), shares his conviction that the entire software market is moving toward AI agents with outcomes-based pricing. He discusses the mindset of daily impact prioritization that enabled his success across wildly different roles, why his biggest failure at Google led to Google Maps, and where the biggest remaining opportunities for startups lie in the AI era.

Leadership Principles

→ The whole market is going to go towards agents and outcomes-based pricing — it's so obviously the correct way to build and sell software
→ Wake up every morning asking 'what is the most impactful thing I could do today' — this mindset enables success across wildly different roles
→ Selling productivity software is extremely hard — learned this the hard way at Quip — which is why agents that deliver outcomes will win

Notable Quotes

"The whole market is going to go towards agents. The whole market is going to go towards outcomes-based pricing. It's just so obviously the correct way to build and sell software."
— On the future of software and AI agents

"I was the product manager for Google Local. Had a pretty tough product review with Marissa and Larry. To not do that well with a link from the Google homepage is embarrassing. They gave me another shot to do the V2 that resulted in Google Maps. We got about 10 million people using it on the first day."
— On his biggest failure leading to his biggest success

"Waking up every morning — what is the most impactful thing I could do today?"
— On the mindset that enabled success across Google, Facebook, Salesforce, and Sierra

Want to know how you compare?

Take the Assessment