EP 150: Bret Taylor (CEO, Sierra): A New Class of Software Winners

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.

Logan is joined by Marc Benioff, the legendary co-founder and CEO of Salesforce, for a wide-ranging conversation on the rise of AI in enterprises. Marc explains how Salesforce has become the testing ground for its own “agentic” technology, using AI agents to handle customer support, boost sales, and transform marketing. He also shares his perspective on what’s hype vs. reality in the AI race, the opportunities for startups, and why the future is about humans and agents working together. (00:00) Introduction and Salesforce's Lead Management (00:35) Reflecting on the Last Eight Months (01:14) The Impact of AI on Salesforce Operations (02:15) AI's Role in Customer Support and Sales (03:45) Salesforce's Vision for an Agentic Enterprise (05:00) Public Market Sentiment and AI Adoption (06:15) Salesforce's Data and Application Foundations (08:13) The Future of CRM and ITSM Markets (12:57) Managing Agents and Human Workers (17:45) Salesforce's Growth and AI Product Line (19:38) Pricing Models and Customer Success Stories (23:26) The Role of AI in Different Market Segments (28:51) Salesforce Ventures and Startup Investments (36:05) Advice for Young Professionals and Future Trends (41:04) Dreamforce Executive Producer: Rashad Assir Producer: Leah Clapper 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.

Joe Hudson is the founder of The Art of Accomplishment and has worked with many top leaders in Silicon Valley, including Sam Altman and executives from Apple, Google, the NBA, and more. He coaches the research and compute teams at OpenAI and works with all the major AI companies. With a background in international stock lending and venture capital, and now a reknowned executive coach, Joe brings a unique perspective on business and the world. In this conversation, he shares many of the principles he uses to help top leaders adopt to maximize impact and achievement. (00:00) Intro (00:36) The Journey of Self-Inquiry (02:30) Impact of Self-Reflection on Coaching (03:50) Defining the Role of a Coach (07:23) Emotional Clarity vs. Emotional Intelligence (11:22) Achieving Emotional Clarity in Leadership (15:20) The Art of Accomplishment (18:33) Time Horizons and Incremental Improvements (21:18) Common Challenges for High Achievers (27:21) Self-Reliance and Team Dynamics (31:10) Coaching in the AI World (34:51) Reflections on AI and World War II (37:07) Skepticism and Trust in AI (42:30) Embracing Change and Transformation (50:04) The Importance of Experimentation in Business (57:45) Self-Awareness and Leadership (01:02:14) Practical Steps for Personal and Organizational Growth Learn more about Joe’s work: - Learn more + complimentary transformation guide: artofaccomplishment.com - Art of Accomplishment Podcast (Spotify / YouTube) - Daily insights on Twitter: @FU_Joehudson Executive Producer: Rashad Assir Producer: Leah Clapper 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.

Chris Degnan is one of the most legendary CROs of this generation. He joined Snowflake as employee #13 and the 1st sales hire. He scaled the sales org from 0 to over $3B in ARR, spanned four CEOs, and retired as CRO after 11 years. In his first podcast post-retirement, Chris opened his CRO playbook, from early enablement to hiring rigor and fending off threats from competitors. He also reflects on lessons from working with leaders like Frank Slootman, John McMahon, and Sridhar Ramaswamy. If you’re a founder or running sales at a startup, this one is for you. (00:00) Introduction to Chris's Journey at Snowflake (01:47) Navigating Leadership Changes (04:39) The Importance of Sales Methodology and Enablement (10:22) Near-Death Experiences and Company Resilience (13:39) Building a Strong Sales Organization (27:25) Hiring and Scaling the Sales Team (34:52) Board Dynamics and Mentorship (44:29) The Influence of John McMahon (46:22) Leadership Styles and Intuition (46:56) Launching Snowflake Japan (49:39) Learning from Leaders (55:10) The Importance of Competitive Moats (59:12) Snowflake vs. Databricks (01:07:45) Public vs. Private Markets (01:14:03) Sales and Marketing Synergy (01:26:17) Final Thoughts and Future Plans Executive Producer: Rashad Assir Producer: Leah Clapper 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.

Logan sits down with Bipul Sinha, CEO and co-founder of Rubrik and former VC at Lightspeed and Blumberg Capital. Bipul shares what he learned transitioning from investor to founder, why intuition beats expertise, and how he built Rubrik into a category-defining business by betting on uncool ideas. They talk product-market fit in the AI era, what most VCs get wrong today, and why the enterprise IT market is still just getting started. It’s a conversation packed with hard-earned wisdom and bold takes on building lasting companies. (00:00) Intro (01:42) Transitioning from VC to Founder (02:27) The Genesis of Rubrik (03:30) Navigating Uncertainty in Business (06:57) Product Market Fit and Early Success (08:56) Evolving with the Market (13:14) AI and Data Security (18:53) Leadership and Intuition (28:34) Building a Transparent Culture (31:52) Handling Tough Questions in Board Meetings (33:28) Changing Perspectives Over Time (34:57) Traits of Successful Entrepreneurs (36:46) The Future of Venture Capital and Startups (40:38) Balancing Forward and Lateral Motion in Business (42:35) The Impact of AI on Various Industries (01:00:28) The Evolution of Work and Technology (01:02:52) Fostering a Collaborative Company Culture (01:04:56) Looking Ahead: The Future of Rubrik Executive Producer: Rashad Assir Producer: Leah Clapper 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.

Rick Smith (CEO, Axon) joined Logan to share the 30-year journey of building a nearly $50B public company behind the TASER, police body cameras, and now AI-powered tools like Draft One. He talks about taking Axon public in the early 2000s, navigating intense public scrutiny, and evolving from a controversial hardware startup into a software and AI pioneer. Rick also reflects on leadership lessons, regulatory battles, and his long-term mission to make the bullet obsolete. It’s a candid and compelling conversation with one of the most unconventional founders in tech. (00:00) Intro (01:31) Axon: Reducing Violence Through Technology (02:12) The Evolution of Axon: From Taser to Body Cameras (04:56) Challenges and Triumphs: Going Public and Beyond (07:17) The Impact of Ferguson and the Rise of Body Cameras (11:16) Navigating Cultural and Business Shifts (17:04) The Role of AI and Future Innovations (25:26) The Taser: Technology and Purpose (34:17) Making the Bullet Obsolete: Future of Law Enforcement (37:10) Consumer Market Evolution (37:59) Proving Taser's Viability (40:17) Targeting Gun Owners (41:45) Taser-Related Deaths and Media Perception (48:07) Employee Taser Experience (50:59) Impact of Body Cameras (52:43) AI Innovations in Law Enforcement (56:15) Challenges in Product Development (01:04:27) Regulatory Hurdles (01:11:31) Leadership and Company Culture (01:14:58) Future Vision for Axon Executive Producer: Rashad Assir Producer: Leah Clapper 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.

Logan sits down with Jeffrey Katzenberg, Hollywood legend and co-founder of DreamWorks, and Sujay Jaswa, former CFO of Dropbox - together, the duo behind WndrCo. They talk about building enduring companies, bridging tech and media, and what makes a great CEO partnership. The conversation also touches on storytelling as a business superpower and lessons from scaling at different stages. Whether you're a founder or a media nerd, there’s something here for you. (00:00) Intro (04:26) The Genesis of the Partnership (13:06) Building and Investing in Companies (20:27) The Team and Their Roles (26:52) Decision-Making Process (33:25) Balancing Dreams and Skepticism (35:06) The Dynamics of Partnerships (37:25) Transitioning to Tech (38:45) Cultural Differences in Industries (41:26) The Value of Failure and Success (44:37) Excitement in Emerging Technologies (48:23) The Venture Capital Game (56:42) The Dropbox Talent Network (01:01:20) AI's Impact on Media and Creativity (01:06:18) Transitioning to CG Animation at DreamWorks (01:08:39) Embracing Change in the Intelligence Revolution (01:11:52) The Role of AI in Enhancing Productivity (01:14:11) Building a Consumer Cybersecurity Business (01:23:49) The Mission to Protect Children Online (01:35:17) Reflections on Partnership and Innovation Executive Producer: Rashad Assir Producer: Leah Clapper 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.

In this episode, Logan is joined by Zach Weinberg (Co-Founder/CEO @ Curie.Bio) and Derek Thompson (writer at The Atlantic) for a candid discussion on the state of U.S. healthcare and scientific progress. They unpack what went right, and wrong, with COVID vaccine policy, the public backlash against mRNA technology, and the ripple effects on trust in science. The conversation also dives into the real reasons behind NIH budget cuts, the economics of drug discovery, and the business incentives in medical R&D. It’s a sharp, thought-provoking look at the intersection of policy, innovation, and public perception. (00:00) Introduction to Drug Pricing in the US (00:23) Broad Healthcare Topics and Open-Ended Discussion (02:37) COVID-19 Vaccines: Successes and Public Perception (06:21) The Evolution of COVID-19 and Vaccine Efficacy (07:59) Public Policy and Vaccine Mandates (13:10) Impact of School Closures and Public Sentiment (19:23) NIH Funding and the Importance of Basic Research (25:04) Challenges in Science Funding and Public Perception (35:19) Government vs. Private Investment in Science (36:40) Operation Warp Speed: A Case Study (39:07) Antibiotic Resistance Crisis (43:22) The Drug Pricing Debate (44:05) Challenges in Drug Discovery (54:06) Regulatory Hurdles in Medical R&D (58:06) The Future of Drug Development (01:04:19) Concluding Thoughts Executive Producer: Rashad Assir Producer: Leah Clapper 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.

Yotam Segev is the co-founder and CEO of Cyera, one of the fastest-growing cybersecurity startups in the world. In this episode, he joins Logan to talk about scaling Cyera from 100 to 550 employees in under two years, what it takes to operate at that speed, and why going slow can actually be riskier. They cover lessons from a tough go-to-market year, the emotional conviction behind choosing data security, and how Yotam thinks about platform expansion, hiring, and staying close to customers. It’s a candid look at the mindset and mechanics behind building an elite security company at breakneck pace.(00:00) Intro(01:23) Yotam's Journey in Cybersecurity(02:30) Scaling a Company with Core Values(05:02) Founding Cyera: From Military to Startup(07:59) Entering the Venture Ecosystem(18:19) Early Challenges and Lessons Learned(22:36) Achieving Product-Market Fit(33:01) Ambitious Goals and Rapid Growth(37:39) The Future of Cybersecurity(39:07) The Cybersecurity Paradigm Shift(39:47) Entrepreneurship and Innovation in Cybersecurity(40:25) The Cat and Mouse Game of Cybersecurity(42:47) Traits of Effective CISOs(43:55) Expanding the Cybersecurity Platform(52:36) The Role of AI in Cybersecurity(01:03:25) The Impact of the October 2023 Attack on Israel(01:08:27) Leadership and Company Culture at Cyera(01:12:33) Reflections on Success and Future Goals(01:21:37) Fundraising and Partnerships(01:26:07) Hiring and Company GrowthExecutive Producer: Rashad AssirProducer: Leah ClapperMixing and editing: Justin HrabovskyCheck out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎙 Listen to the showApple 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 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.

Ben Lamm, founder and CEO of Colossal Biosciences, joined the show to talk about the science (and business) of bringing extinct species back to life. Backed by top scientists and investors, Colossal is using advanced gene editing and synthetic biology to recreate animals like the woolly mammoth and dire wolf. Ben walks us through the technology, ethical considerations, and commercialization paths, including tech spinouts and conservation credits. It’s a wild conversation at the intersection of Jurassic Park and deep tech.