The Logan Bartlett Show

Eran Zinman entered a crowded category, out-executed everyone, and scaled monday.com into a $14B public company. In my latest conversation with him, he details their unique metric tracking system (dubbed Big Brain) that allows them to do the same amount of work with ½ the people, along with their relentless focus on cash over other metrics, and the little tactics that brought significant ROI (like sending everyone—including investors—a daily SMS with yesterday’s metrics).(00:00) Introduction to the Logan Bartlett Show(01:12) The Philosophy Behind Monday.com(01:29) Building a Flexible Platform(04:12) Competing in a Crowded Market(06:21) The Evolution of Monday.com(13:43) The Importance of Cash Efficiency(14:22) Big Brain: The In-House Analytics Platform(23:54) Performance Marketing Strategies(29:47) AI Integration and Future Prospects(38:51) Founder Mode and Company Philosophy(40:53) Learning from Mistakes and Adapting(43:04) Customer Success and Service Philosophy(46:53) Building a Strong Company Culture(51:10) Interviewing and Hiring Best Practices(54:49) Going Public and Investor Relations(01:03:38) Co-CEO Model and Partnership(01:08:34) Future Vision for Monday.com(01:11:07) Embracing Failure and Continuous Improvement Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Glenn Fogel, CEO of Booking Holdings, has built a $170B travel empire that includes brands like http://Booking.com, Priceline, Kayak, and OpenTable. Glenn shares insights into how Booking has grown into a global powerhouse, weathering challenges like tsunamis, wars, 9/11, and the COVID-19 pandemic. We dive into the strategy behind the transformative acquisition of http://Booking.com, which now drives 90% of the company’s revenue, and the key lessons Glenn has learned about M&A success. Glenn also discusses how AI could revolutionize travel, from automating customer service to creating seamless traveler-first experiences. (00:00) Intro(01:37) Overview of Booking Holdings(02:31) Early Days of Priceline and Joining the Company(03:33) Dot-Com Boom and Financial Challenges(07:28) Travel Industry Resilience(07:47) Cultural and Economic Factors in Travel(09:17) Stock Splits and Employee Incentives(13:34) Acquisition of Booking.com and Active Hotels(24:20) Growth and Integration of Acquired Companies(29:11) Artificial Intelligence in Travel(30:57) Future of Travel and AI Integration(38:54) The Greatest Acquirers in History(39:16) Teamwork in Business Acquisitions(40:48) Challenges in M&A and Regulatory Hurdles(41:49) Patterns in Successful and Failed Deals(46:06) Cultural Alignment in Mergers(50:31) Brand Management and Integration(54:14) Regulatory Environment and Smart Regulations(01:00:11) Post-COVID Business Travel Trends(01:08:24) Leadership Through Crises(01:15:33) Technological Advancements in Travel Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Ali Ghodsi, CEO of Databricks (now a $61B company), has become one of the top minds in AI, evolving from researcher to leading one of the biggest AI-centered private companies. In our conversation, he broke down the AI hype cycle in detail and made bold predictions for the future. He also shared his biggest operating lessons from scaling Databricks to a market leader and pivotal moments in his journey. (00:00) Introduction to AGI and AI Challenges(01:00) Ali Ghodsi's Journey in AI(01:38) The Evolution and Impact of AI(03:59) AI in Enterprises and Consumer Adoption(05:25) Specialized AI Systems and Data Advantage(07:32) The Hype Cycle and Future of AI(08:22) Scaling Laws and Compound AI Systems(19:52) AI Use Cases and Industry Applications(28:29) Early Days of Databricks and Spark(38:43) Taking Over as Interim CEO(39:00) Focusing on Enterprise Sales(40:42) Innovating in Open Source(41:08) Challenges and Pivots in 2015(44:31) Building and Scaling New Products(47:57) Leadership Evolution and Advice(54:45) Hiring and Promoting Leaders(01:10:44) Future of AI and Databricks Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Eoghan McCabe returned to the CEO seat at Intercom with a mission to shake things up. Over the past two years, he's been reinventing the company’s culture, leading with zero apologies, and transforming Intercom into an AI-driven powerhouse. In my latest conversation, we dive into Eoghan’s journey back to Intercom after a two-year break, his blueprint for turning a software company into an AI leader, and the tactics he uses to keep Intercom running like a high-intensity startup. Eoghan also shares his thoughts on personal freedom and his controversial endorsement of Donald Trump. [0:00] Intro[1:33] Eoghan McCabe's Return to Intercom[3:01] Challenges and Learnings[10:44] Cultural Reset at Intercom[29:23] AI and the Future of Customer Service[31:11] Adapting to AI and Market Changes[43:00] Competitive Landscape and Strategy[48:29] Future of AI in Customer Service[50:24] The Evolution of Work[52:18] Challenges and Rewards of Leadership[56:45] Media and Public Perception[1:00:40] Political Endorsements and Reactions[1:10:11] Freedom Club and Cultural Influence[1:12:33] HR and Company Culture[1:29:35] Fundraising and Investor Relations[1:33:01] Final Reflections and Advice  Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

What does it take to scale a company from an idea to a $13B industry leader? In my latest episode, Okta CEO Todd McKinnon dives into the essential lessons he’s learned on high-stakes decision-making, managing up to the board, and competing against tech giants like Microsoft.Todd also reflects on his journey to founding Okta, his bold choice to team up with a co-founder he hardly knew, and the motivations that have fueled him for over seven years as a public company CEO. Some key takeaways… [0:00] Intro[0:33] Todd McKinnon's Early Career and Founding Okta[1:38] Challenges and Psychological Shifts in Leadership[2:49] Decision Making and Company Culture[6:10] Milestones and Early Successes[18:03] The Importance of Market Timing[30:34] Hiring and Building a Strong Team[39:22] Setting Expectations with Board Members[40:50] The Shift in Board Dynamics[41:41] Maintaining Context and Strategic Input[43:15] Navigating Public Company Governance[45:21] Trusting Instincts and Founder Mode[47:11] Breaking Out of the Echo Chamber[51:00] The Importance of Prioritization[53:05] The Loneliness of Innovation[1:05:33] The Role of a CEO in Decision Making[1:18:17] The Journey to IPO and Beyond  Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Nine months into his role as Snowflake’s CEO, Sridhar Ramaswamy sat down for a candid discussion on the journey so far & what’s ahead.He uncovered details about his transition to Snowflake CEO, the operational changes he’s put in place to accelerate product development, and his bold predictions for AI’s future—along with how he’s guiding a vision for Snowflake to fit into that landscape.Sridhar also reflects on how his leadership has evolved, from leading a major Google unit to founding Neeva (acquired by Salesforce) and now running Snowflake. [0:00] Intro[0:56] Sridhar’s Journey to Snowflake[3:37] Snowflake's AI Vision and Cortex AI[10:35] Innovative Uses of AI at Snowflake[15:49] Challenges and Future of AI in Business[21:27] Snowflake's Long-Term AI Aspirations[25:04] Predictable and Unpredictable Aspects of AI[26:20] Autonomous Agents and AI Predictions[27:01] Market Consolidation in AI[29:54] Journey into AI and Early Experiences[31:21] The Evolution of AI Models[32:06] Building Neeva and AI Search Engines[36:16] Leadership and Product Development at Snowflake[40:45] Setting Goals and Accountability[43:25] Leadership Style and Cultural Foundations[47:25] Career Advice and Finding Your Path  Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Evan Goldberg has been leading NetSuite for 26 years and counting. In this episode, Evan reflects on the journey of building NetSuite—from launching it with Larry Ellison’s support, to scaling through its IPO, and eventually being acquired by Oracle for $9.3B. He shares his leadership philosophies around humor and empathy, lessons learned from Larry Ellison and Marc Benioff, and why he still feels passionate about the business after all these years. [0:00] Intro[1:13] Lessons from Economic Crises[2:22] The Importance of Existing Customers[4:24] Founding and Early Days of NetSuite[6:32] The Pivot to Business Software[10:26] NetSuite's Growth and Customizability[20:26] AI and the Future of NetSuite[32:24] The Role of Customizability in NetSuite's Success[38:49] Balancing Profitability and Growth[40:46] Leadership Evolution and Management Philosophy[46:59] The Importance of Empathy in Leadership[48:42] Navigating Hypergrowth and Tough Decisions[51:11] Consumer Quality in Enterprise Software[52:31] Oracle's Transformation and Redwood Design System[55:57] Maintaining Focus Amid Distractions[59:39] Company Culture and Humor[1:03:03] NetSuite's Unique Position within Oracle[1:10:15] Involvement with the V Foundation[1:13:52] Reflections on Founding and Leadership[1:16:38] Conclusion and Final Thoughts  Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Drew Houston has now been CEO of Dropbox for over 17 years. In my latest conversation, he opens up about the pivotal leadership lessons he's learned, the mistakes that shaped the company, and the true challenges of going head-to-head with big tech. We also dive into the highs and lows of fundraising, how valuations can make or break a company trajectory, and discuss the opportunities AI presents for the future of work. [0:00] Intro[0:44] AI Opportunities for Dropbox[5:57] Dropbox's AI Principles[7:52] Introducing Dropbox Dash[9:18] AI Enhancements in Search[12:33] Personal Productivity with AI[17:10] Memo-First Culture at Dropbox[22:15] Reflections on Leadership and Growth[31:21] Early Challenges and Viral Growth[48:22] Facing Fierce Competition[51:51] Strategic Shift to Collaboration[53:20] Navigating Internal Challenges[55:18] Reevaluating Productivity[1:03:07] The Birth of Dash[1:16:32] You Don't Want to Feel Like a Victim[1:30:29] Closing Thoughts and Lessons Learned  Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Will Gaybrick joined Stripe as CFO after investing in the company at Thrive Capital. Over the past 9 years, now as President, he's helped grow Stripe's into one of the world's largest private startups. In this episode, we explore his impressive career journey—from Harvard Math to software engineering, Yale Law, venture capital, and now his leadership role at Stripe. Will shares key insights on capital allocation, crypto, AI, investing, leadership, and more. Some takeaways:(00:00) Intro(01:09) From Academia to Venture Capital(02:01) Joining Stripe: The Unexpected Journey(02:09) Career Philosophy and Decision Making(05:23) Building Hack Yale and Teaching(08:15) The Role of a Polymath at Stripe(09:31) Learning Techniques and AI Insights(16:15) Operational Shifts and Growth Strategies(20:36) Hiring and Leadership at Stripe(28:08) Organizational Systems and Processes(31:40) Migrating Users to New API Versions(32:07) Challenges in API Refactoring(33:57) The Rise of Stablecoins(34:07) Stripe's History with Crypto(35:51) Stablecoins: Use Cases and Adoption(41:30) AI and Machine Learning at Stripe(47:59) Risk Management and Compliance(53:21) Empowering Innovation with AI(57:14) Decision-Making Frameworks at Stripe(01:04:07) Stripe's Product Evolution(01:09:31) Exploring the Fun and Challenges of Product Space(01:10:20) Stripe's Organizational Structure and Strategy(01:12:12) The Importance of Technical Unification(01:13:13) User Demands and Capital Allocation(01:14:18) The Role of ROI in Early Projects(01:15:53) Stripe's Unique Approach to Titles and Levels(01:18:36) Insights on Organizational Design(01:21:36) Effective Leadership and Decision-Making(01:24:18) Reflections on Influential Leaders(01:33:25) The Value of Venture Capital(01:38:29) Future Prospects and Motivation at Stripe  Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Parker Conrad has spent the last 8 years building Rippling into a $13B company, marking his redemption after being ousted from Zenefits. In his second appearance on the podcast, Parker and I discussed Paul Graham's "founder mode" essay and how he operationalizes it at Rippling. He also reflected on the key lessons he's learned throughout his career, highlighting the differences in how he ran Zenefits compared to Rippling today. Additionally, Parker shared his candid views on the challenges of having investors as board members and why he believes much of VC "value add" is overrated.(00:00) Intro(01:31) Parker's Leadership Principles at Rippling(02:16) The Importance of Anecdotal Evidence(04:09) Balancing Founder Mode and Team Collaboration(05:08) The Risks of Over-Extrapolating Founder Mode(06:56) The Reality of Sales Compensation(08:15) Hiring Founders for New Products(11:10) The Pace of Execution in a Company(11:21) The 'C on a Box' Dilemma(12:07) The Speed vs. Quality Debate(13:56) The Viral Tweet Incident(16:51) Governance and Board Dynamics(20:04) Choosing the Right Investors(29:57) The Role of Career VCs as Board Members(33:43) Misaligned Incentives Between Founders and Investors(35:43) Navigating Business Challenges(36:27) Sam Altman's Crucial Support(38:45) The Role of Venture Capitalists(40:06) The Value of Y Combinator(43:16) Fundraising and Valuations(01:00:39) Lessons from Past Ventures(01:06:05) Building Compound Software(01:09:33) The Future of Compound Software Businesses(01:10:04) Microsoft's Unassailable Approach(01:10:40) Building Narrow vs. Compound Software(01:12:16) Investment Decisions in New vs. Existing Products(01:14:42) Platform Development and Resource Allocation(01:16:32) The Journey from Chem Major to Software Visionary(01:18:34) Challenges and Strategies in Multi-Product R&D(01:25:32) Improving Customer Support Metrics(01:28:50) The Role of a Founder in Product Management(01:31:23) Hiring and Cultivating Executive Talent(01:39:07) The Motivation Behind Rippling's Success(01:41:58) Conclusion and Final Thoughts Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Many know Celsius as a top energy drink brand today, but few are aware of the tumultuous journey CEO John Fieldly took to get it here. In the episode, John shared how the company nearly went bankrupt multiple times, lost 50% of its revenue overnight and even got delisted from the NASDAQ.Despite these challenges, John stepped up to rebuild the brand to the nearly $10B company it is today. We discuss how he shifted focus from weight loss to broad-based energy, secured key distribution deals, landed a major partnership with Pepsi, and much more. (00:00) Intro(01:34) The Origins of Celsius(03:30) Going Public: The Early Days(06:07) Challenges and Lawsuits(09:17) Rebuilding and Rebranding(13:18) Strategic Shifts and Market Positioning(30:40) The Role of Influencers and Social Media(32:03) John Fieldly's Leadership Journey(33:34) Reflecting on the Stock Price Journey(34:12) Navigating Public Company Challenges(35:25) Distribution Deals and Market Perception(38:00) Strategic Moves and Competitive Advantage(44:08) Marketing Strategies and Consumer Engagement(52:35) Leadership and Company Culture(01:02:01) International Expansion and Future Goals(01:06:01) Conclusion and Final Thoughts Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Josh Wolfe, co-founder and managing partner at Lux Capital, is a master at quickly understanding complex, emerging technologies. In our conversation, Josh shared how he identifies the next big thing, his contrarian views on nuclear energy, biotech, and robotics, as well as his thoughts on the state of the venture capital market today.(00:00) Intro(01:02) Daily News Routine(05:28) Geopolitical Insights(07:03) Competitiveness and Curiosity(11:01) Investment Strategies and Risks(26:07) The Control Labs Story(33:48) The Founder’s Dilemma: Financial vs. Strategic Motivations(34:33) Geopolitical Concerns: Iran and Global Politics(36:31) Investments in Defense: Controversies and Convictions(37:36) The State of Society: Happiness and Social Dynamics(48:07) Artificial Intelligence: Trends and Predictions(01:02:22) The Future of Robotics: Beyond Humanoids(01:06:46) Ethical Implications of AI and Defense Technologies(01:11:29) Lux Capital’s Investment Strategy and LP Relations(01:12:43) ESG and Moral Impositions(01:13:30) Defense and Complex Moral Valences(01:14:19) Investment Ethics and Decision Making(01:16:46) Venture Capital Market Outlook(01:17:56) Challenges in Venture Capital(01:37:12) The Role of Storytelling in Venture Capital(01:43:20) Personal Reflections and Background(01:51:34) Partnership Dynamics and Trust(01:53:48) Conclusion and Final Thoughts Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Emery Wells is the co-founder and CEO of Frame.io, which he sold to Adobe in 2021 for nearly $1.3 billion. In our conversation, Emery shares his journey from NYC bartender to startup founder, including his agency work with Saturday Night Live that highlighted the pain points that led to Frame.io. We dive deep into his rejection of the lean startup concept, how he gets his team to obsess over design details, and the cultural reset at Frame.io that set the stage for its success.(00:00) Intro(01:34) Emery's Journey to Founding Frame.io(03:23) SNL Digital Shorts and Post-Production Insights(08:30) From Bartender to Entrepreneur(11:45) Building Frame.io: Challenges and Philosophy(23:14) Leadership and Decision-Making in Startups(28:40) Cultural Crisis and Turning Points(30:10) Understanding Company Culture(32:57) The Big Reset: Leadership Changes(34:16) Defining and Implementing Values(38:09) Hiring for Cultural Fit(39:18) The Importance of Design(46:06) Framework for Quality Execution(54:23) Building a B2B Brand(58:17) Effective Launch Strategies(01:05:36) Fundraising Lessons(01:08:30) The Art of Storytelling in Presentations(01:09:19) Meeting Key Industry Figures(01:10:06) The Acquisition Dance with Aaron Levy(01:16:04) Adobe's Acquisition Interest(01:18:12) Navigating the Acquisition Process(01:27:04) Lessons from Adobe's Culture(01:29:59) The Impact of AI on Creativity(01:34:16) Advice on Board Selection and Dynamics(01:41:40) Final Thoughts and Reflections Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Dara Khosrowshahi runs one of the most complicated businesses in the world, Uber. Since taking over in 2017 Dara has led the company to profitability against all odds. In this episode, we touch on a number of things including Uber’s position on the future of Autonomous Vehicles (AVs), the challenges that were overcome in making Uber profitable, and some of the operating principles that have stuck with Dara since his days at Expedia. (00:00) Intro(01:49) Uber's Economic Resilience and Consumer Trends(04:40) The Future of Autonomous Vehicles(14:27) Strategic Decisions and the Advanced Technologies Group(31:01) Uber's Expansion and Competitive Landscape(38:01) Living in the Suburbs: Practical Insights(39:23) Cultural Reset at Uber: A Necessity(42:39) Operational Efficiency: Lessons from Uber(46:56) Global Adaptations: Uber's Local Innovations(48:58) Leadership and Mentorship: Personal Reflections(51:32) Career Path: From Finance to CEO(01:00:14) The Importance of Constructive Conflict(01:04:47) Long-term Strategy and Board Governance(01:07:07) The Impact of Uber: A Global Perspective(01:08:54) Conclusion and Farewell Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Mike Maples is an 8x Midas List investor and founding partner at Floodgate Fund. In our conversation, we dive into his latest book, "Pattern Breakers: Why Some Startups Change The Future." Mike shares his frameworks on how top startups beat incumbents by redefining categories, and he reflects on his worst and best decisions. We also discuss what the future of venture capital may look like over the next decade - here are a few favorite takeaways on what makes outstanding startups from one of the industry's most influential names.(00:00) Intro(01:12) Meet Mike Maples: Venture Capital Icon(04:20) The Genesis of Twitch and Startup Pivots(07:51) Understanding Inflections in Startups(14:38) The Role of Insights and Ideas in Startup Success(22:13) The Importance of Movements and Founder-Future Fit(26:10) Case Studies: Quibi, Tesla, and More(43:41) The Trap of Mundane Startup Ideas(45:36) The Inflection Stress Test for Startups(47:06) The Twitter Success Story(52:40) The Rise of Seed Funding(56:55) Traits of Successful Founders(59:39) The Importance of Storytelling in Startups(01:05:47) Navigating the Challenges of Disruptive Startups(01:08:31) Reflections on Early Investment Decisions(01:13:57) Entering the Venture Capital World(01:20:25) The Evolution of the Tech Industry(01:22:47) Reflecting on the Dot-Com Era(01:23:06) The Evolution of Cognition and AI(01:24:03) Investment Strategies and Market Trends(01:25:56) The AI and Dot-Com Bubble Comparison(01:33:46) The Rise of Bitcoin and Crypto(01:37:02) Navigating Venture Capital Cycles(01:49:57) Advice for Aspiring Investors(01:54:09) The Importance of Authenticity and Specialization(02:03:20) Closing Thoughts and Reflections Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Josh Reeves has built Gusto into a nearly $10B company with over $500M in ARR, serving small businesses. In our conversation, Josh delves into Gusto’s 13-year journey, sharing insights on how they achieved product-market fit by initially targeting a very narrow niche. He also highlights the tactics they’ve used to build an intentional culture of humility and helpfulness, along with lessons he’s learned in hiring executives. We also explore the future of Gusto and the opportunities that lie ahead for the business.(00:00) Intro(00:36) Early Days and Product Market Fit(01:02) Building a Scalable Business(01:41) Gusto's Core Offerings and Customer Focus(02:51) Challenges and Strategies in Payroll(05:40) Expanding Gusto's Reach(10:11) Customer Feedback and Product Development(23:03) Hiring and Company Culture(29:23) Values and Leadership at Gusto(37:14) Sustaining Passion and Long-Term Vision(43:27) Balancing Growth and Sustainability(46:29) Balancing Competition and Kindness in Startups(46:38) The Importance of Team Collaboration(47:47) Navigating Feedback: Kindness vs. Niceness(48:25) Hiring for Ambition and Humility(49:57) Aligning Company Values with Success(53:11) Work-Life Integration at Gusto(56:11) Building a Long-Term Oriented Business(57:15) Mentorship and Learning from Other Founders(01:00:09) Structuring and Scaling Product Teams(01:06:16) Organizational Design and Leadership(01:08:31) Hiring Executives and Internal Growth(01:13:13) The Journey of Rebranding to Gusto(01:21:05) The Role of a CEO in a Growing Company(01:28:39) Fundraising and Investor Relations(01:33:14) Future Goals and Impact of Gusto(01:35:48) Conclusion and Final Thoughts Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Eric Glyman (CEO, Ramp) shared his operating playbook for leading one of the fastest-growing startups on his second appearance on the podcast. We also explored the unique ways Ramp leverages AI internally, strategies for startups to build moats in AI, and the concept of self-driving money. We concluded with one of the most profound and thoughtful discussions about hiring, motivations, and success I've ever had on the podcast. It was truly enjoyable to sit down with a seasoned portfolio founder.(00:00) Introduction and Episode Overview(01:03) Market Reflections and Ramp's Growth(04:01) Artificial Intelligence in Business(10:09) Ramp's AI Implementation: Toby the Slack Bot(16:49) AI's Impact on Business Models and Hiring(31:15) The Future of Organizational Structure(31:36) The Evolution of Bookkeeping(33:49) The Impact of Automation on Bookkeeping Jobs(35:31) Streamlining Expense Management with Ramp(37:00) The Concept of Self-Driving Money(38:09) AI Integration in Ramp's Services(39:38) Zero Touch AI and Customer Experience(40:54) Agentic AI and Practical Applications(49:15) Balancing Autonomy and Centralization in Organizations(56:09) Developing New Products at Ramp(01:04:01) Resource Allocation in Organizations(01:05:00) Creating Conditions for Success(01:08:37) Balancing Existing and New Products(01:11:02) Hiring for Curiosity(01:16:09) The Pursuit of Perfection(01:21:21) The Joy of the Process(01:24:37) Building a Timeless Product(01:33:15) Conclusion and Reflections   Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Klarna CEO Sebastian Siemiatkowski led the rise from a profitable business to their peak $50 billion valuation, in which they were burning $150 million a month. In my latest episode, Sebastian shares how he turned Klarna back to profitability and discusses Klarna’s ongoing pursuit of creating a digital financial assistant. He also reflects on their recent boardroom drama with Sequoia and outlines the operating principles and the repaired mistakes that have made Klarna the company it is today.(00:00) Intro(01:45) Personal Reflections on Alcohol and Family(03:03) The Journey to Sobriety(05:57) Milestones and Achievements(07:59) Understanding Company Success(10:54) Challenges and Pivots in Business(16:50) Building and Maintaining Company Culture(26:16) Leadership and Motivation(32:42) What Klarna Does(41:33) Reflecting on Leadership and Self-Development(41:48) Promoting Young Talent and Internal Growth(44:52) Balancing Autonomy and Standardization(46:29) Adopting Agile and Toyota's Influence(55:05) Navigating Regulatory Challenges(01:00:11) Klarna's Financial Journey and Market Expansion(01:10:38) Handling Valuation Resets and Layoffs(01:23:57) Evaluating Individuals in Business Relationships(01:24:22) Stability of Institutions and Individuals(01:25:40) Perverse Incentives in VC Firms(01:26:50) Hands-On Leadership in VC Firms(01:28:54) The Impact of Michael Moritz(01:34:52) Leadership Evolution and Self-Reflection(01:39:11) Facing Challenges and Finding Solitude(01:42:19) AI Integration at Klarna(01:52:03) Balancing Capitalism and Societal Impact(02:00:53) Creativity and Constraints in Problem Solving(02:05:41) Conclusion and Final Thoughts Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Olivier Pomel built Datadog into a $40B company while burning only $25M in capital. In our conversation, he shares the fundraising lessons, operating principles, and core insights that made this possible. He also discusses the pros and cons of building a tech company in NYC, how early-career professionals should approach learning AI tools, how Datadog is building a trusted relationship with their users around AI features, and much more(00:00) Intro(01:30) Datadog's Early Challenges and Lessons(04:32) The Core Insight Behind Datadog(05:20) Building the Right Product(07:46) Transitioning to Open Beta(09:38) Expanding Datadog's Product Line(11:26) Platform Vision and Modular Products(18:12) Empowering Product Teams(22:14) Acquisitions and Integration Strategy(33:18) Customer-Centric Approach(36:39) Bottom-Up Sales Strategy(46:04) Navigating Founder Challenges(46:37) Building a Collaborative Management Team(48:32) Staying Close to Customers(51:36) Maintaining a Culture of Discipline and Efficiency(56:26) Pricing Strategy and Market Positioning(01:01:24) Fostering a Low-Ego, High-Performance Culture(01:06:32) Hiring and Promoting for Long-Term Success(01:12:21) Fundraising and Investor Relations(01:16:03) Deciding Whether to Sell or Scale(01:18:26) The Impact of AI on Software Development(01:23:24) Choosing New York Over Silicon Valley(01:28:04) Final Thoughts and Reflections Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.

Steve Kaufer led Tripadvisor to multi-billion dollar success over a 20+ year run as CEO. He discusses getting acquired and spun out from IAC, becoming a public company CEO, and his biggest operating lessons from his decades-long journey. Steve also shares behind-the-scenes of his new venture, Give Freely, and reflects on his entrepreneurial path. (00:00) Intro(01:00)  Steve Kaufer's Journey with Tripadvisor(03:18) Handling Negative Reviews and Legal Issues(05:24) Psychology of Reviews and User Behavior(10:01) Impact of AI on Review Platforms(15:02) Graduation Speech and Key Lessons(16:33) Speed Wins: The Importance of Agility(22:46) Measuring Success and Embracing Change(28:40) Hard Work and Personal Growth(36:20) Management and Leadership Insights(40:23) Setting Company Culture(48:00) Adapting to Market Changes(51:45) Hiring the Right People(53:27) Identifying Red Flags in Interviews(54:51) The Importance of Self-Improvement(55:29) Curiosity and Adaptability in Candidates(56:36) Managing Through Crises: 9/11 and COVID-19(01:02:12) Lessons from Early Career and Centerline Software(01:05:02) Founding Tripadvisor and Its Growth(01:18:03) Tripadvisor's Acquisition and Integration with IAC(01:25:23) Transitioning from Tripadvisor to Give Freely(01:27:26) The Vision and Impact of Give Freely(01:37:10) Conclusion and Final Thoughts Show Notes:https://givefreely.com/  Executive Producer: Rashad AssirProducer: Leah ClapperMixing 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 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.