EP 150: Bret Taylor (CEO, Sierra): A New Class of Software Winners
Fri Sep 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 AIExecutive Producer: Rashad AssirMixing and editing: Justin HrabovskyCheck out Unsupervised Learning, Redpoint's AI Podcast: <a class="link" href="https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA" target="_blank" rel="noopener noreferrer">https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA</a>🎙 Listen to the showApple Podcasts: <a class="link" href="https://podcasts.apple.com/us/podcast/the-logan-bartlett-show/id1606770839" target="_blank" rel="noopener noreferrer">https://podcasts.apple.com/us/podcast/the-logan-bartlett-show/id1606770839</a>Spotify: <a class="link" href="https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1" target="_blank" rel="noopener noreferrer">https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1</a>🎥 Subscribe on YouTube: <a class="link" href="https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1" target="_blank" rel="noopener noreferrer">https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1</a>Follow on Socials📸 Instagram - <a class="link" href="https://www.instagram.com/theloganbartlettshow" target="_blank" rel="noopener noreferrer">https://www.instagram.com/theloganbartlettshow</a>🐦 Twitter - <a class="link" href="https://twitter.com/loganbartshow" target="_blank" rel="noopener noreferrer">https://twitter.com/loganbartshow</a>🎬 Clips on TikTok - <a class="link" href="https://www.tiktok.com/@theloganbartlettshow" target="_blank" rel="noopener noreferrer">https://www.tiktok.com/@theloganbartlettshow</a>About the ShowLogan 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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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 AIExecutive Producer: Rashad AssirMixing and editing: Justin HrabovskyCheck out Unsupervised Learning, Redpoint's AI Podcast: <a class="link" href="https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA" target="_blank" rel="noopener noreferrer">https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA</a>🎙 Listen to the showApple Podcasts: <a class="link" href="https://podcasts.apple.com/us/podcast/the-logan-bartlett-show/id1606770839" target="_blank" rel="noopener noreferrer">https://podcasts.apple.com/us/podcast/the-logan-bartlett-show/id1606770839</a>Spotify: <a class="link" href="https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1" target="_blank" rel="noopener noreferrer">https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1</a>🎥 Subscribe on YouTube: <a class="link" href="https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1" target="_blank" rel="noopener noreferrer">https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1</a>Follow on Socials📸 Instagram - <a class="link" href="https://www.instagram.com/theloganbartlettshow" target="_blank" rel="noopener noreferrer">https://www.instagram.com/theloganbartlettshow</a>🐦 Twitter - <a class="link" href="https://twitter.com/loganbartshow" target="_blank" rel="noopener noreferrer">https://twitter.com/loganbartshow</a>🎬 Clips on TikTok - <a class="link" href="https://www.tiktok.com/@theloganbartlettshow" target="_blank" rel="noopener noreferrer">https://www.tiktok.com/@theloganbartlettshow</a>About the ShowLogan 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.