The Logan Bartlett Show
The Logan Bartlett Show
by Redpoint Ventures
EP 150: Bret Taylor (CEO, Sierra): A New Class of Software Winners
1 hour 8 minutes Posted Sep 12, 2025 at 10:00 am.
) Introduction and Recent Milestone
) AI Market and Historical Comparisons
) Competitive Landscape and Business Models
) Outcome-Based Pricing and Value Creation
) Technological Shifts and Business Transitions
) Adoption Challenges and Forward Deployed Engineering
) Early Investment in Snowflake and Cloud Strategy
) Enterprise Software Market Dynamics
) AI Agents and Implementation Costs
) Democratization of Software Development
) The Future of Software Companies and AI Agents
) Consumer Behavior and AI Agents
) The Role of AI in Customer Experience
) Career Advice in the Age of AI
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Show notes
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.
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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.