Three Cartoon Avatars

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

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

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

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

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

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

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

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.

Blake Scholl, founder and CEO of Boom Supersonic, is leading the boldest effort in decades to bring back commercial supersonic flight—this time with product-market fit.We talk about what went wrong with the world's first try at supersonic commercial aircraft (launched in the 70s), why Boeing hasn't introduced a new plane in over a decade, and how Blake's startup is building a jet that flies 2x faster than today's aircraft—without the sonic boom. This episode is a crash course in engineering ambition, regulatory dysfunction, and what it takes to defy gravity and incumbents.(00:00) Intro(00:40) The History and Evolution of Aviation(01:12) The Rise and Fall of Concorde(05:25) The Impact of Government and Founders on Innovation(08:57) Regulatory Challenges and Business Models(26:53) Boom's Vision for Supersonic Travel(47:10) Building Trust with Regulators(48:16) Challenges in the Aerospace Startup(49:36) Recruiting Talent from Unlikely Places(55:47) The Importance of Mission Success Events(01:01:52) Developing a Custom Jet Engine(01:22:54) Reindustrialization and Economic Strategy(01:34:42) Conclusion and Final ThoughtsExecutive 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

College sports are going through massive changes—from athlete pay drama to superconference realignment and transfer portal chaos, not to mention the giant class action lawsuit playing out now.Matt Brown, the publisher behind Extra Points and one of the top experts on the business of college athletics, joined the show to break it all down. We walked through the full history of college sports, the current money dynamics, and where things could be headed. (00:00) Meet Matt Brown: Expert in College Sports Business(03:09) The Origins of College Sports(06:31) The Evolution of College Sports Broadcasting(14:53) Title IX and Its Impact on College Athletics(17:53) The 1984 Supreme Court Decision and Its Aftermath(20:03) The SMU Death Penalty Scandal(22:19) Conference Realignment and the BCS Era(28:22) The Rise of Conference Television Networks(30:23) The Arms Race in College Sports Facilities(34:41) The Role of Boosters in College Sports(36:03) Financial Breakdown of Major College Sports Programs(37:04) Understanding Nonprofit Accounting in College Athletics(38:20) Revenue Generation in College Sports(40:34) Athletics as Enrollment Management(42:04) The Flutie Effect and University Applications(44:37) Conference Realignment and Financial Instability(48:58) The O'Bannon Case and Video Game Licensing(53:59) The Northwestern Unionization Attempt(58:19) The Alston Case and Educational Awards(01:02:11) Name, Image, and Likeness (NIL) Marketplaces(01:05:51) The Role of Collectives in College Sports(01:12:08) Dependability of Young Campaign Partners(01:13:03) Transfer Portal and Its Impact(01:15:56) Rise of NIL Agents and Handlers(01:17:40) Economic Incentives and Transfer Market(01:20:37) Challenges in NIL Enforcement(01:22:48) House Settlement and Future Implications(01:25:38) Allocation of NIL Funds by Universities(01:44:26) Potential Super Leagues and Investment Challenges(01:48:07) Concluding Thoughts on College SportsExecutive 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

In this episode, Derek Thompson (Writer, The Atlantic) delves into the tumultuous nature of Trump's trade policies, especially regarding tariffs, and how they impact American manufacturing and global markets. They discuss the constant changes in policy, the resulting uncertainty for industries like automotive and aerospace, and the mismatch between Trump's ‘madman strategy' and effective industrial policy. The conversation also explores the broader economic consequences, including stock market volatility, housing affordability issues, and the role of government in promoting economic growth and innovation.(00:00) Intro(00:20) Trump's Trade Policy and Its Implications(01:30) The Uncertainty of Tariff Policies(02:12) Impact on American Manufacturing(05:15) Stock Market Reactions(07:00) Debating the Effectiveness of Tariffs(10:02) Wall Street vs. Main Street(18:44) Housing and Healthcare Challenges(34:53) Historical Context of Housing Regulations(41:48) The Reality of Construction Jobs(42:35) The American Dream and Housing Costs(42:57) The 30-Year Mortgage and Its Impact(43:48) Comparing Home Ownership to Stock Market Investments(45:14) Political Reception of the Book 'Abundance'(46:17) Pro-Business Democrats and Government's Role(48:38) The Need for Aggressive Democratic Leaders(51:18) The Importance of Economic Growth(01:01:26) Debating Government's Role in Industrial Policy(01:03:34) Challenges in the Semiconductor Industry(01:13:19) The Housing Problem in New York City(01:15:26) Conclusion and Final ThoughtsExecutive 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

Debate between Keith Rabois and Zach Weinberg on what tariffs are actually trying to accomplish. One core theme: Tariffs aren't fully about “bringing back factories,” but rather a negotiation tool to eliminate foreign trade barriers - ultimately aiming to increase free trade, not restrict it.We also got into:- What each of them would do if they were in charge- Whether the trade deficit is a meaningful metric or just a misunderstood talking point- If tariffs could be part of an initiative to replace income tax — shifting toward a more consumption-based tax system- If tariffs could successfully be used as a non-military tool to reduce drug supply to the US- If there's a major disconnect between the new administration's rhetoric and the actual economic goals behind the policyOne of the deepest economic conversations from the show's recent history — and a rare debate where both sides had real logic behind their views.(00:00) Introduction and Host's Biases(00:46) Keith's Perspective on Tariffs(03:05) Zach's Perspective and Clarifying Questions(05:14) Debating Tariff Strategies(07:45) Economic Implications and Free Trade(13:31) Trump's Tariff Policies and Goals(16:57) Global Trade and Protectionism(25:52) Final Thoughts on Tariffs and Trade(29:16) Discussion on Trade Tariffs and Partners(30:17) Impact of Tariffs on GDP and Debt(31:20) Political Coalitions and Trade Policies(32:00) Tariffs as Consumer Taxes(33:30) Debate on Trade Deficit and Tariff Rates(36:53) Regulatory Reforms and Economic Policies(47:25) Fentanyl Crisis and Trade Negotiations(51:06) Closing Remarks and Future TopicsExecutive 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

In this freeform episode, Logan sits down with Zach Weinberg (Co-Founder and CEO of Curie.Bio) to break down two of the biggest storylines in tech: tariffs and AI.They banter through the core arguments for and against tariffs, including national security, domestic employment, and negotiation power. Plus, they revisit what's happened in past trade wars and share predictions on the real economic consequences this time around.Logan and Zach also discuss OpenAI's $40B raise and the broader race for AI dominance—can OpenAI maintain its lead against tech giants like Google and Apple? They debate the limits of product defensibility, the power of platform defaults, and the strategic moves OpenAI might need to make to stay ahead.Topics include:The arguments for and against tariffsWhat happened during past U.S. tariff cycles—and how this one comparesWhether OpenAI can maintain its edge in a world of native AI platformsA possible playbook for OpenAI to build user lock-in beyond utilityWhat this era of AI competition means for the U.S.—and what could derail ithttps://fdra.org/wp-content/uploads/2025/03/Trade-War-Lessons-from-the-Past-2025.pdf?utm_source=newsletter&utm_medium=email&utm_campaign=newsletter_axiosmacro&stream=business00:00 Intro01:35 Liberation Day and Global Trade02:13 Freeform Discussion on Various Topics02:44 Podcasting and VC Life03:32 Debating Tariffs and National Security11:26 Arguments Against Tariffs22:19 Historical Context of Tariffs26:58 Economic Predictions and Stagflation33:39 The Forgotten Lessons of Recessions36:02 The Fixed vs. Growth Mindset in Economics37:17 The Democratic Party's Shift on Economic Policies42:33 The Rise of Populism and Its Impact50:28 OpenAI's Explosive Growth and Challenges54:28 The Competitive Landscape of AI58:33 The Future of AI and Consumer Behavior01:07:20 The Role of Social Networking in AI's Future01:10:43 Wildcard: The Role of XAI and GrokExecutive Producer: Rashad AssirProducer: Leah ClapperMixing and editing: Justin HrabovskyCheck out Unsupervised Learning, Redpoint's AI Podcast: / @redpointai

Box CEO Aaron Levie joined the show to share his perspective on how AI is reshaping the enterprise landscape. He shared what his customers are actually thinking about when it comes to AI, the shift from closed to open-source models, and why the biggest opportunities might not be in flashy consumer tools but in workflow automation and data-rich enterprise applications. Aaron also shares his take on the changing business model dynamics in B2B, including the rise of usage-based pricing, and what it means for the next wave of software companies. 00:00 Introduction to AI in B2B and Consumer Worlds 00:32 Conversation with Aaron Levy: AI in the Enterprise 01:10 Defining a Model Company and AI's Role 02:19 Challenges and Opportunities in AI for Enterprises 03:44 Open Source vs. Commercial AI Models 05:40 The Future of AI Agents 11:42 AI's Impact on Business Models and Pricing 15:16 AI's Potential to Transform Industries 27:14 Comparing AI and Cloud Adoption 30:05 Strategizing AI Implementation 31:08 Customer Adoption and Resistance 32:59 Practical Considerations and Challenges 34:58 Building Flexible AI Architectures 37:57 Exploring Agentic Workflows 41:57 Future of AI in Enterprises 43:36 Rapid Fire Questions on AI Impact 53:20 Exciting AI Features at Box 55:53 Conclusion and Final Thoughts

After unveiling 45 new product announcements this week, Zoom CEO Eric Yuan joined the show to share how he's thinking about the future of work. He shared how he prioritizes which features to build, his approach to rebuilding company culture, what he'd do differently if he were starting Zoom today, and much more.Chapters0 Introduction to Digital Twins and AI in Zoom59 Zoom's AI Innovations at Enterprise Connect115 The Evolution of AI Companions174 Zoom's Open Platform and AI Integration234 Democratization of AI Features293 Optimizing AI Infrastructure353 Zoom's AI and Vertical Services412 Voice Recorder and Calendar Management470 Bottom-Up Innovation at Zoom529 Customer Feedback and Innovation589 Problem-Solving Framework at Zoom648 Zoom's Scope and Adjacencies707 Integrating with Calendars and Third-Party Systems767 Custom Solutions for Diverse Customer Needs828 Zoom's Shift to an AI-First Platform887 Leveraging AI for Workplace Efficiency943 Exploring Zoom's AI Features1001 Zoom Docs and Zoom Clips1059 Zoom Team Chat and Customer Education1116 Innovation Speed and Customer Discovery1174 Future of Meetings and Immersive Experiences1233 Digital Twins and AI in Meetings1293 Understanding Digital Twins1353 Developing Digital Assistants and Twins1413 Resource Allocation for Future Innovations1471 AI and Data Privacy at Zoom1527 Zoom's Commitment to Data Privacy1586 Customer Feedback Influencing Product Direction1643 Adapting to Customer Needs in AI Development1701 Eric Yuan's Hands-On Leadership Style1760 Zoom's Culture and Customer Obsession1819 Maintaining Culture Through Growth1877 Zoom's Pandemic Growth and Cultural Challenges1936 Rebuilding Zoom's Company Culture1995 Continuous Improvement and Self-Reflection2053 Zoom's Commitment to Customer Happiness2112 Daily Self-Reflection for Personal Growth2167 Navigating Hybrid Work Challenges2226 Strategies for Effective Hybrid Work2283 Supporting Hybrid Work with Zoom Features2341 Improving Hybrid Conference Room Experiences2398 Eric Yuan's Founding Insight at Zoom2456 Zoom's Video-Centric Approach2514 Ensuring Consistent Video Experience2576 Lessons from Cisco and Engineer Collaboration2635 Early Competitive Landscape and Audio Focus2695 The Importance of Audio in Video Conferencing2753 Timing and Market Entry for Zoom2810 Surviving the Market as an Early Mover2868 Lessons from Visa Rejections2927 Perseverance and Never Giving Up2986 Maintaining Confidence and Resilience3046 Early Non-Scalable Approaches3104 Lessons from Third-Party Partnerships3164 Bottom-Up Team Building at Zoom3224 Hiring for Self-Learning and Motivation3282 Prioritizing Potential Over Experience3339 Advice for 2011 Eric Yuan3398 Learning from Funding and Growth3457 Being Aggressive with Capital Deployment3517 Long-Term Planning and Vision3575 Reflecting on Strategic Decisions3634 Choosing the Right Investors3690 Building Lasting Partnerships3749 Future of AI in Industry3809 AI's Potential in Healthcare3867 Closing Remarks

As tariff drama continues to heat up, Ryan Petersen, CEO of Flexport (one of the hottest freight forwarders in the world) came on the show to unpack the impact. Ryan also dives deep into the hidden world of US shipping, opportunities for AI automation in logistics, reflections on building Flexport, and some supply chain conspiracy theories.(00:00) Intro(01:16) Flexport's Mission and Operations(02:28) Impact of Tariffs on Businesses(05:15) Navigating New Duties and Regulations(09:19) Flexport's Strategic Response(14:39) Challenges in U.S. Shipping Policies(28:21) Union Influence on Port Automation(40:35) National Security and Trade Negotiations(41:06) Tariffs and Business Planning Challenges(42:16) Investment Opportunities in Ports(44:02) Port Automation and AI Integration(45:09) Flexport's Big Tech Launch(47:02) AI's Role in Supply Chain Management(53:14) Digitizing Freight Contracts(58:18) Lessons from Flexport's Growth(01:09:13) Conspiracy Theories in Shipping 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

Yamini Rangan, CEO of HubSpot (a $40 billion leader in the CRM space) shares how AI is transforming go-to-market strategies, the key lessons Yamini has learned as a first-time CEO, and the sales tactics she's mastered.She also discusses the challenges of navigating major business pivots, including how companies can successfully transition into AI-first businesses and what it takes to stay competitive in an evolving landscape.(00:00) Intro(00:56) Yamini Rangan's Background and Career Journey(02:33) Joining HubSpot and Early Challenges(03:49) Transition to CEO and Leadership Insights(07:33) Strategic Planning and Long-Term Vision(15:15) AI Transformation and Product Innovation(18:57) AI's Impact on CRM and Future Prospects(28:51) Content Strategy and Customer Engagement(37:34) Contextual AI Features for Better Usage(38:13) Human Expectations and AI(39:36) AI in Daily Productivity(42:54) The Art and Science of Sales(51:05) The Role of Curiosity and Resilience in Sales(53:23) Evolving Company Culture(55:27) Leadership Style and Management Lessons(58:27) Scaling Startups: Lessons from Workday(01:02:54) The Future of AI and Incumbents(01:14:10) Concluding 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

Andy is the founder of Artisanal Ventures and Artisanal Talent, one of Silicon Valley's top search firms. He's helped build leadership teams at companies like Databricks, Snowflake, Confluent, Abnormal Security, AcuityMD, and many more.In this episode, he shares…- How founders can differentiate in the talent war today- Maximizing the success rate of executive hires- Why interviews are a waste of time- The best ways to do references- How to choose the right search firm& more (00:00) Intro(02:02) Andy Price's Background and Career Journey(03:20) The Role of Founders in Hiring(04:32) Challenges in Early Stage Hiring(10:08) Importance of Venture Capital Brand(12:14) Effective Search Processes and Candidate Evaluation(23:27) Backchannel References and Networking(29:10) Identifying Key Players in Sales Growth(29:44) The Importance of Minimal Disruption(30:40) Effective Founder-Executive Relationships(30:57) The Role of Soak Time in Differentiation(31:52) Hiring Strategies for Rapid Growth(33:42) Common Failure Modes in Hiring(34:32) Aligning Founder and Executive Expectations(38:26) Building a Strong Talent Acquisition Team(40:51) The Talent Wars and Hiring Choke Points(44:24) Balancing Skill Sets and Company Culture(47:29) Evaluating and Upleveling Team Members(49:59) The Importance of Forecasting and Planning(51:34) Handling Executive Transitions Smoothly(59:09) The Art of Firing: Best Practices(59:32) Handling Employee Terminations with Dignity(01:02:19) Negotiating with Candidates: Tips and Tricks(01:06:31) Understanding Compensation Trends(01:08:18) Avoiding Common Founder Mistakes(01:11:28) Scaling Operations in Hypergrowth(01:15:00) Navigating the Current VC and Talent Ecosystem(01:23:34) The Importance of Specialized Search Firms(01:28:03) Adapting to the New Market Realities(01:30:46) 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

The recent controversy between WordPress and WP Engine put Matt Mullenweg (Co-Founder of WordPress, CEO of Automattic) under intense online scrutiny. In our conversation, he shared lessons from the controversy and managing through crisis, as well as this thoughts on the future of open source AI and more.(00:00) Intro(01:17) Controversy with WP Engine(03:36) Understanding Open Source and Trademarks(04:36) Automattic's Role and Contributions(08:26) Navigating Legal Battles and Community Relations(18:27) Leadership and Personal Resilience(21:49) The Impact of Social Media on CEOs(31:22) Future Outlook and Reflections(32:42) Exploring the Quinn Model and Open Source Innovations(33:17) The Evolution of AI Interfaces and User Interactions(35:36) AI as a Writing and Coding Partner(38:07) The Power of Open Source in AI Development(40:00) Commoditizing Complements: A Business Strategy(41:39) The Battle with Shopify and Open Source Models(42:33) The Impact of Open Source on Market Dynamics(43:55) USB-C Transition and Gadget Recommendations(47:53) The Benefits of Sabbaticals(53:34) The Future of WordPress and Automattic(59:12) Employee Ownership and Liquidity Programs(01:04:33) 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 

Two weeks after Oura CEO Tom Hale started tracking and improving his sleep, he recalls, “It was like walking out of a black-and-white movie into a 4K technicolor movie… I've been missing this for 30 years.” The experience of feeling 20 again every day inspired him to apply for the Oura CEO role. Now, nearly 3 years into the job, he sat down to discuss what all founders and CEOs should consider when it comes to avoiding burnout and maximizing health and productivity. We covered his experiences with tools like continuous glucose monitoring, his thoughts on the future of wearables, and how AI insights will help us take better control of our health. (00:00) Intro(00:53) The Journey with Oura Ring(01:47) Sleep Optimization and Health Trends(05:06) Behavioral Changes for Better Sleep(09:33) Tom Hale's Professional Background(12:47) Challenges and Opportunities at Oura(22:50) The Importance of Sleep(26:05) Health Benefits of Quality Sleep(28:38) Oura's Unique Position in the Market(36:47) Consumer Choice and Healthcare Disruption(40:59) Unexpected Insights from HSA and FSA Spending(41:36) The Future of Insurance and Wearable Data(44:40) Preventative Care and Employer Incentives(47:21) The Impact of Small Choices on Health(48:52) Artificial Intelligence in Healthcare(54:08) The Role of Continuous Glucose Monitors(59:50) Expanding Oura's Market and Product Strategy(01:12:04) Navigating Leadership and Company Culture(01:19:22) Future Opportunities and Global Expansion(01:23:43) Closing Remarks 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

Jay Chaudhry is the definition of a self-starter. Born in the Himalayas with no running water or electricity until high school, Jay has now scaled Zscaler to a $30B public company. He and his wife went all in many times over—betting their life savings and quitting their jobs to launch their first venture, Secure IT, which became a huge success. Jay then parlayed that into building multiple more self-funded, successful cybersecurity companies before founding Zscaler.In this episode, Jay shares his playbook for building disruptive companies, how he picks a market, and insights on using AI to combat modern breaches—plus his perspectives on life, family, and money. 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

In this episode, Marc Benioff (CEO, Salesforce) responds to Satya Nadella's recent predictions and shares his thoughts on the current reality of Agi. He dives into the rise of digital labor, the multi-trillion-dollar potential of agentic technology, and what the future split between software and agentic revenue might look like. Marc also discusses why CEOs need to stay grounded in delivering actionable solutions, and he emphasizes the moral obligation businesses have to retrain employees and invest in communities as AI continues to evolve.(00:00) Intro(01:45) Salesforce's AI Impact on Business(03:03) The Future of Digital Labor(05:28) Agentic AI and Customer Success(07:42) Salesforce's Competitive Edge(11:48) Marc Benioff's Response to Satya Nadella(14:16) The Role of AI in Enterprise Software(20:14) The Balance of AI and Human Labor(28:34) Salesforce's Philanthropic Efforts(36:24) The Future of AI and Regulation(40:24) 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

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

(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

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

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: Sam Dewees and JR Bohannon Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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: Sam Dewees and JR Bohannon Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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[25:20] Voice Interfaces and Data Transformation[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: Sam Dewees and JR Bohannon Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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: Sam Dewees and JR Bohannon Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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: Sam Dewees and JR Bohannon Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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

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

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

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

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

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

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

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

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 Overview01:03 Market Reflections and Ramp's Growth04:01 Artificial Intelligence in Business10:09 Ramp's AI Implementation: Toby the Slack Bot16:49 AI's Impact on Business Models and Hiring31:15 The Future of Organizational Structure31:36 The Evolution of Bookkeeping33:49 The Impact of Automation on Bookkeeping Jobs35:31 Streamlining Expense Management with Ramp37:00 The Concept of Self-Driving Money38:09 AI Integration in Ramp's Services39:38 Zero Touch AI and Customer Experience40:54 Agentic AI and Practical Applications49:15 Balancing Autonomy and Centralization in Organizations56:09 Developing New Products at Ramp01:04:01 Resource Allocation in Organizations01:05:00 Creating Conditions for Success01:08:37 Balancing Existing and New Products01:11:02 Hiring for Curiosity01:16:09 The Pursuit of Perfection01:21:21 The Joy of the Process01:24:37 Building a Timeless Product01:33:15 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

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

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

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

Since 2017, Bill Shufelt (CEO, Athletic Brewing) went from hedge fund trader to the CEO of the leading producer of non-alcoholic craft beer. Unlike the typical tech-focused chats, this one centers around a product many have fallen in love with. In the conversation, Bill tells stories of the unscalable but crucial strategies he used to build a brand, push past rejection, and redefine the non-alcoholic beer industry. (00:00) Introduction to Athletic Brewing(00:52) The Early Days and Breakthrough Moments(01:15) Celebrity Partnerships and Brand Building(03:16) The Philosophy of Brand and Movement(07:33) The Non-Alcoholic Beer Market(10:46) The Entrepreneurial Journey and Personal Sacrifices(18:22) Scaling the Business and Marketing Strategies(28:20) Navigating Regulations and Health Trends(39:07) The Importance of a Tech Co-Founder(39:31) Home Brewing Beginnings(40:13) Innovative Brewing Process(41:13) Food Safety Challenges(43:24) Raising Funds and Building a Brewery(44:24) Vertical Integration Benefits(45:33) Early Sales Efforts(46:56) Investor Relations and Accountability(51:14) Long-Term Vision and Focus(01:00:10) Cultural Differences in Non-Alcoholic Beer(01:02:35) Health Considerations and Alcohol(01:10:38) The Sensation of Drinking(01:12:50) Reflections on the Entrepreneurial Journey(01:14:46) 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

In the midst of meme stock craziness, Robinhood CEO Vlad Tenev shared his most eye-opening insights from running the company that transformed the game for retail investors. He talks about Robinhood's new Gold Card, his views on crypto, the media side, how artificial intelligence could change finance, and more. (00:00) Intro(03:27) The Origin of the Name 'Robinhood'(08:43) Navigating the GameStop and Meme Stock Saga(10:52) Rebuilding Trust and Brand Impact(19:10) Crisis Communication and Leadership Lessons(23:54) Industry Insights and Future of Trading(31:00) AI and Financial Services(33:34) Crypto and Regulatory Challenges(40:14) The Viral Launch of Robinhood(47:01) The Gold Card Launch and Customer Strategy(50:08) The Vision Behind Robinhood's Credit Card(53:50) Building vs. Buying: The X1 Acquisition(56:12) Integrating X1 into Robinhood(57:11) The GM Structure and Its Benefits(58:42) Challenges and Trade-offs of Decentralization(01:01:08) Financial Modeling and Customer Economics(01:04:48) Navigating Remote Work and Returning to the Office(01:09:14) Managing Stock Price Expectations(01:13:23) Hiring and Retaining Talent(01:17:11) Fundraising and Investor Relations(01:31:09) Launching Sherwood Media(01:38:56) Reflections and Future Aspirations 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

On the day of the ChatGPT-4o announcement, Sam Altman sat down to share behind-the-scenes details of the launch and offer his predictions for the future of AI. Altman delves into OpenAI's vision, discusses the timeline for achieving AGI, and explores the societal impact of humanoid robots. He also expresses his excitement and concerns about AI personal assistants, highlights the biggest opportunities and risks in the AI landscape today, and much more. (00:00) Intro(00:50) The Personal Impact of Leading OpenAI(01:44) Unveiling Multimodal AI: A Leap in Technology(02:47) The Surprising Use Cases and Benefits of Multimodal AI(03:23) Behind the Scenes: Making Multimodal AI Possible(08:36) Envisioning the Future of AI in Communication and Creativity(10:21) The Business of AI: Monetization, Open Source, and Future Directions(16:42) AI's Role in Shaping Future Jobs and Experiences(20:29) Debunking AGI: A Continuous Journey Towards Advanced AI(24:04) Exploring the Pace of Scientific and Technological Progress(24:18) The Importance of Interpretability in AI(25:11) Navigating AI Ethics and Regulation(27:26) The Safety Paradigm in AI and Beyond(28:55) Personal Reflections and the Impact of AI on Society(29:11) The Future of AI: Fast Takeoff Scenarios and Societal Changes(30:59) Navigating Personal and Professional Challenges(40:21) The Role of AI in Creative and Personal Identity(43:09) Educational System Adaptations for the AI Era(44:30) Contemplating the Future with Advanced AI 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

After 18 years leading Guidewire (~$10B), Marcus Ryu made the transition from CEO to partner at Battery Ventures. In the episode, Marcus shares his journey of co-founding Guidewire in 2001, steering the company through its IPO in 2012, and building one of the largest vertical software businesses in the world. He shares his insights on how to build a durable company in troubling times, what he looks for in entrepreneurs, the future of vertical software, and much more. (00:00) Intro(01:31) The Philosophical Approach to Investing and Strategy(03:27) Unpacking the Strategy: Diagnosis, Market Definition, and Execution(04:31) The Intricacies of Investment Decisions and Entrepreneurial Insight(10:39) From Philosophy to Silicon Valley: A Personal Journey(12:29) The Dot-com Bubble and Lessons Learned(26:19) Guidewire's Founding: Identifying a Niche in the Insurance Industry(37:13) The Early Days: Building from Scratch(37:34) The Founder's Balance Sheet: Energy, Time, and Market Demand(37:54) Starting with Nothing: The Humble Beginnings of a Startup(38:14) The Power of Insight and Precision in Startup Success(39:58) Product Development and Market Strategy: The Binder's Role(40:37) The Brutal Reality of Go-to-Market: Rejection and Resilience(42:59) The Parable of the Horse: Navigating Startup Highs and Lows(45:23) Overcoming Legal Battles and Finding a Moral Purpose(48:37) The CEO Transition: Learning from Leadership Changes(50:49) Foundational Principles for Sustaining Founder Relationships(53:41) Cultivating a Company Culture Based on Core Values(01:01:31) The Journey from Founder to Investor: A New Chapter(01:03:53) The Role of a Board and Achieving Founder-Investor Alignment(01:08:25) Managing Founder Psychosis and Scaling as a Leader(01:12:52) The Founder's Journey and Commitment(01:13:27) The Philosophical Underpinnings of Insurance(01:14:03) Insurance: A Civilizational Necessity(01:15:01) The Impact of Insurance on Society and Innovation(01:19:32) Navigating the Complexities of Insurance Regulation(01:21:07) The Dark Side of Ad Tech and Its Societal Impact(01:28:41) The Challenge of Communication and Leadership(01:31:46) The Future of Software: Vertical Specialization(01:42:05) Evaluating Founders and the Essence of Entrepreneurship(01:45:56) Emerging Opportunities and the Specificity of Markets(01:48:53) Concluding Reflections on Authentic Leadership Executive Producer: Rashad AssirProducer: Leah ClapperMixing and editing: Justin Hrabovsky

After last week's announcement that IBM is acquiring HashiCorp for $6.4B, HashiCorp co-founder Armon Dadgar discussed a few behind-the-scenes elements of the acquisition and HashiCorp's full journey from the early days. Armon shares some of his biggest lessons from the journey, from fundraising to community building and more. (00:00) Intro(01:17) Explaining HashiCorp: Simplifying Cloud Infrastructure for Enterprises(03:24) Navigating the Acquisition: Emotions, Expectations, and the Future with IBM(09:01) The Founding Story: Choosing the Path of a Venture-Backed Business(10:59) Challenging Silicon Valley Wisdom: HashiCorp's Multi-Product Strategy(17:54) The Importance of Being Pragmatic: Adapting Products to Market Needs(32:27) Customer Trust and Commitment: The Foundation of HashiCorp's Success(36:27) Organizational Evolution: Adapting Structure to Strategy at HashiCorp(38:36) Exploring Product Verticals and Team Structures(39:16) The Evolution of Product Portfolio(40:46) Strategic Product Development and Market Fit(41:51) Transitioning from Product Expansion to Monetization(43:27) The Impact of Docker on Fundraising and Strategy(50:31) Navigating the Challenges of Multi-Product Strategy(55:33) The Significance of Branding and Product Naming(01:00:46) Understanding User vs. Buyer Dynamics in Open Source Monetization(01:09:17) The Founders' Journey: From University to HashiCorp(01:16:39) Navigating Leadership and Hiring Challenges(01:17:14) The Search for the Right Leadership: A Journey of Discovery(01:17:57) Realizing the Need for Specialized Roles(01:18:24) The Turning Point: Hiring Key Executives(01:19:57) Overcoming the Ego: Embracing Change for Company Success(01:21:18) The Final Decision: Bringing in New Leadership(01:22:45) Reflecting on the Hiring Process and Its Impact(01:28:27) Building a Culture of Execution and Communication(01:50:51) The Importance of Airline Loyalty for Busy Executives 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 

Before Andrew Bialecki took Klaviyo public and scaled the company to $6B, he bootstrapped it to over $1M in ARR. In our discussion, Andrew reveals his philosophies around fundraising, finding the best talent, cultivating entrepreneurship inside Klaviyo, scaling culture, and more. (00:00) Intro(01:13) Klaviyo's Bootstrap Beginnings(09:37) The Strategic Pivot to E-commerce and Retail(15:02) Narrow Focus as a Catalyst for Growth(25:48) Building a Culture of Learning and Growth(34:02) The Entrepreneurial Path: From Engineer to Founder(37:09) The Commute to Innovation: A Startup Journey(37:57) From Performable to HubSpot: A Tale of Acquisition and Growth(39:26) Building Klaviyo: Lessons in Entrepreneurship and Team Building(40:40) Scaling a Startup: The Challenges of Leadership and Hiring(47:04) Fostering a Culture of Experimentation and Entrepreneurship(53:15) The Art of Hiring: Identifying Entrepreneurial Spirit(58:39) Chronological Resumes and the Power of Storytelling in Interviews(01:06:16) Embracing the Unsexy: The Philosophy of 'Eating Your Vegetables'(01:13:33) Klaviyo University: Training Future Founders and Leaders(01:15:25) Cultivating a Culture of Learning at Klaviyo(01:16:17) The Genesis of Klaviyo University(01:17:05) Core Curriculum and Electives: A Deep Dive(01:20:46) Adapting Learning Programs in a Remote World(01:21:56) The Art and Science of Effective Business Writing(01:28:35) Recruitment and Onboarding: Strategies for Success(01:38:05) Building and Sustaining Company Culture(01:41:28) Leveraging Boston's Ecosystem for Growth(01:47:06) The Future of Software: Productivity vs. Output(01:52:33) Closing Thoughts and Acknowledgements Produced: Rashad Assir & Leah ClapperMixed and edited: Justin HrabovskyExecutive Producer: Josh Machiz

After 23+ years in venture capital, Jeremy Levine has thrived in many eras, taking risks on now-iconic companies like LinkedIn, Shopify, Yelp, Pinterest, and more. In our discussion, Jeremy shared stories behind these investments and the mindsets he's developed along the way. We also explored how the VC landscape has evolved over the last 20 years and where the industry may head next. Plus, Jeremy shares insights from his journey into VC, along with foundational advice and principles that anyone aspiring to succeed in the industry may find valuable. Overall, an in-depth discussion for anyone who wants to nerd out on venture capital with us. (00:00) Intro(01:03) Exploring the Personal Motivations Behind Venture Capital(01:41) The Impact of Technology on Venture Capital(03:11) The Reality of Venture Capital Impact(06:45) The Ideal Venture Investment: The Donut Company Metaphor(07:30) Operator vs. Career Investor: The Best Venture Capitalists(09:57) The Dynamics of Choosing a Venture Investor(14:03) The Unique Paths to Success in Venture Capital(17:04) Authenticity and Adaptability in Venture Capital(26:33) Navigating the Complexities of Venture Capital Careers(34:11) Jeremy Levine's Journey to Bessemer Venture Partners(40:00) Navigating the Venture Capital Landscape: Insights and Strategies(40:30) The Competitive Edge in Early 2000s Venture Capital(43:26) Reflections on Career Paths and the Role of Serendipity(47:04) The Intricacies of Decision Making in Venture Capital(52:37) Evaluating Investment Opportunities: The Price Sensitivity Debate(55:22) Learning from Success and Failure: The Jet.com Story(01:08:26) The Evolution of Successful Entrepreneurs: Insights from Shopify and Yelp(01:16:22) The Strategic Advantage of Repeat Entrepreneurs in the Startup Ecosystem(01:19:38) Navigating Market Dynamics: Insights and Analogies(01:20:09) The Evolution of a Venture Capitalist: From Ideas to Impact(01:21:22) Pioneering User-Generated Content: A Venture Success Story(01:23:36) Exploring E-Commerce and the Power of Advertising(01:24:59) Innovative Investment Strategies: SaaS and Payment Processing(01:34:53) Bessemer's Legacy and Venture Capital Evolution(01:39:57) Expanding Horizons: Bessemer's Global and Diverse Investment Approach(01:52:35) Cultivating Talent and Embracing Industry Dynamics(02:02:36) Navigating Budgets and Investment Strategies in Venture Capital(02:03:55) The Importance of Accountability and Decision-Making Records(02:05:46) Investment Memo Strategies: Beyond Templates(02:08:43) The Dynamics of Voting and Decision Making in VC Firms(02:16:19) The Evolution of Venture Capital: Trends and Predictions(02:21:13) Building a Successful Venture Capital Firm: Culture and Operations(02:29:57) Mentorship and Individual Growth in Venture Capital(02:39:40) Navigating the AI Investment Landscape(02:41:36) The Debate on Announcing Funding Rounds(02:44:20) Closing Remarks  Produced: Rashad Assir & Leah ClapperMixed and edited: Justin HrabovskyExecutive Producer: Josh Machiz

Garrett Langley is the CEO of Flock Safety, a $4B company helping solve 10% of US crimes with AI-powered tech. Garrett offers an in-depth look into Flock Safety's ambitious vision to eliminate crime in America and all the operating lessons he's learned along the way, including how to build a strong and motivated team, keep people accountable, and leverage PR for rapid growth. (00:00) Intro(01:03) The Mission to Eliminate Crime with Innovative Tech(01:54) The Genesis of Flock Safety: A Response to High Crime Rates(07:48) The Evolution of Flock Safety's Crime-Fighting Technology(24:37) Impact Stories: How Flock Safety is Changing Lives(31:00) Navigating the Balance: Safety, Privacy, and Community Impact(36:58) Exploring the Universal Appeal of Safety Across America(37:38) The Role of Community Decisions in Public Safety(39:02) Addressing Misinformation and Enhancing Safety with Technology(39:58) Collaboration and Data Sharing Among Cities(41:26) The Impact of Technology on Policing and Public Safety(43:24) Innovative Solutions to Modern Policing Challenges(49:18) Flock's Vision for the Future of Public Safety(56:05) Building a Business on Solving Crime(56:38) The Importance of Team and Culture in Business Success(01:10:45) Navigating Growth and Maintaining Culture in a Scaling Company(01:12:33) Cultivating a Strong Remote Work Culture(01:12:46) The Power of Cultural Norms in Business(01:13:01) Building Accountability and Responsiveness(01:14:16) The Importance of In-Person Interactions in a Hybrid Company(01:14:50) Assessing Substantive Work Over Managing Up(01:17:50) The Strategy of Being a Macro Optimist and Micro Pessimist(01:20:16) Celebrating Milestones and Focusing on Impact(01:21:58) The Unique Dynamic of Working with Family(01:30:42) Reflections on Early Success and the Drive to Build Meaningful Companies(01:37:58) Overcoming Fundraising Challenges and Understanding Market Dynamics(01:46:55) Concluding Thoughts and the Future of Flock Safety  Produced: Rashad Assir & Leah ClapperMixed and edited: Justin HrabovskyExecutive Producer: Josh Machiz

In less than 8 years, Sanjit Biswas scaled Samsara from 0 to over $1B ARR. In our latest conversation, Sanjit shares all the lessons he's learned about running a hyper-growth organization, including all the changes he's made since growing and selling his first company Meraki to Cisco for $1.2B and going on to scale Samsara to $20B. A great episode for anyone who wants to continuously reinvent themselves within a rapidly changing workplace. (00:00) Intro(01:28) Samsara's Journey: From Startup to Billion-Dollar Valuation(06:50) The Evolution of Samsara's Product Line: From Temperature Sensors to AI(12:48) The Impact of ELD Mandate on Samsara's Growth(14:16) Expanding Horizons: Samsara's Multi-Product Strategy(29:41) Leadership Lessons: Scaling a Company and Rehiring Yourself(38:07) Insights on Hiring: Finding the Right Fit for Growth(40:56) Maintaining High Hiring Standards in Rapid Growth(42:21) Innovative Hiring Practices: Talent Calibrators and Bar Raisers(43:12) Embracing a Flexible Workplace Post-Pandemic(43:20) Navigating the Shift to Remote Work and Its Impact on Talent Acquisition(45:06) Evaluating Employee Performance and the Keeper Test(46:42) Lessons from Legendary Venture Capitalists and Building Board Relationships(50:16) Samsara's Journey: Building a Billion-Dollar Business(50:34) From Academic Project to Commercial Success: The Meraki Story(54:35) The Power of Direct Sales and Learning from Customer Interactions(01:14:24) Reflecting on Growth, Culture, and the Future of Samsara(01:24:08) Closing Thoughts and Advice for Future Founders Produced: Rashad Assir & Leah ClapperMixed and edited: Justin HrabovskyExecutive Producer: Josh Machiz Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA