The Logan Bartlett Show

Author: by Redpoint Ventures

Startups grow faster and avoid costly mistakes when they learn from those who came before them. In each episode, we sit down with the people behind todays most important startups and extract the tactics, lessons, and frameworks theyve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.
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EP 150: Bret Taylor (CEO, Sierra): A New Class of Software Winners
Episode 150
Friday, 12 September, 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 🎙 Listen to the show Apple Podcasts: https://podcasts.apple.com/us/podcast/the-logan-bartlett-show/id1606770839 Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 🐦 Twitter - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow 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.