September 12, 2025
Bret Taylor is the CEO of Sierra and Chairman of the Board of OpenAI. He previously served as co-CEO of Salesforce. I sat down with Bret to explore how the AI revolution compares to previous platform shifts and what it means for both startups and incumbents navigating this transition.
(00:00) Introduction and Recent Milestone
(00:38) AI Market and Historical Comparisons
(02:30) Competitive Landscape and Business Models
(06:02) Outcome-Based Pricing and Value Creation
(13:52) Technological Shifts and Business Transitions
(26:32) Adoption Challenges and Forward Deployed Engineering
(37:21) Early Investment in Snowflake and Cloud Strategy
(38:02) Enterprise Software Market Dynamics
(38:38) AI Agents and Implementation Costs
(41:06) Democratization of Software Development
(43:35) The Future of Software Companies and AI Agents
(49:36) Consumer Behavior and AI Agents
(58:56) The Role of AI in Customer Experience
(01:01:25) Career Advice in the Age of AI
Executive Producer: Rashad Assir
Mixing and editing: Justin Hrabovsky
Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA
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About the Show
Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.
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