EP 122: Okta CEO Todd McKinnon on Scaling to $13B, High-Stakes Decisions, and Market Dynamics

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.