Podcasts about Redpoint Ventures

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.In this episode, I sat down with Logan Bartlett, Managing Director of Redpoint Ventures. We explore the evolving landscape of venture capital and startup investing and dive deep into the challenges facing unicorn companies post-2021, the transformative potential of AI, and the critical factors for successful startup investments. Logan shares insights on identifying promising founders, navigating market uncertainties, and the importance of adaptability in both founding teams and venture capital. Key takeaways include the need for founders with rapid learning capabilities, the potential disruption and opportunities in AI, the changing dynamics of startup valuations and exits in a challenging market environment, and so much more.About Logan BartlettLogan Bartlett is a Managing Director at Redpoint Ventures, where he leads early-growth investments in enterprise software, with a focus on infrastructure, SaaS, and AI. Since joining Redpoint in 2020 after six years at Battery Ventures, Bartlett has backed high-growth companies such as Ramp, Cribl, Cyera, Monte Carlo, FloQast, Crossbeam, and Workato. His work has earned him recognition on both the Forbes 30 Under 30 and the Midas Brink lists.Beyond investing, Bartlett hosts The Logan Bartlett Show, a podcast featuring in-depth conversations with top founders, operators, and investors. The show offers insights into startup growth, market cycles, and venture capital strategies, and has become a respected resource within the tech ecosystem.Redpoint Ventures, founded in 1999, is a venture capital firm that partners with visionary founders to create and redefine markets. The firm invests in startups across various stages, from seed to growth, and has backed over 578 companies, including industry giants like Snowflake, Looker, Kustomer, Twilio, and Netflix. With 181 IPOs and M&A exits and managing $7.2 billion across multiple funds, Redpoint's expertise in guiding businesses toward success is well-established.Timestamps:In this episode, we discuss:* Logan Bartlett's Path into Venture Capital (1:46)* The 2021 Unicorn Logjam and Future Outlook (4:38)* AI's Role in Reshaping Legacy Companies (8:32)* Liquidity Challenges and Growth Stage Investing (11:16)* Portfolio Construction and Risk Balance (17:16)* Underwriting Series B Investments (22:41)* Portfolio Composition and Risk Appetite (26:36)* Evaluating AI Companies and Revenue Durability (30:01)* Forecasting and Macro Underwriting (35:32)* Key Investment Decision Criteria (40:11)* Traits of Successful Venture Investors (45:28)* Final Thoughts and Takeaways (49:58)I'd love to know what you took away from this conversation with Logan. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you'd like to be considered as a guest or have someone you'd like to hear from (GP or LP), drop me a direct message on X. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

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

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

Rish Gupta has had a long, winding journey filled with unexpected turns, painful challenges, and exhilarating wins. He has built and exited companies and is currently riding the incredible momentum and hype in the artificial intelligence world of AGIs. Rish's latest company, Spot AI, has attracted funding from top-tier investors like Redpoint Ventures, Scale Venture Partners, Bessemer Venture Partners, and StepStone Group.

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

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.Had a great conversation recently with Tomasz Tunguz Founder and General Partner at Theory Ventures. We dug into how AI is reshaping venture capital and everyday life, from the rapid advancements in the space to what it all means for startups and the broader market. We covered everything from the declining cost of training AI models to the open vs. closed-source debate and how enterprises are starting to adopt AI in real ways. A really insightful discussion—hope you enjoy it.About Tomasz TunguzTomasz Tunguz is the Founder of Theory Ventures, where he invests in early-stage technology companies with a focus on SaaS, data infrastructure, and machine learning. Renowned for his deep analytical insights and data-driven approach to venture capital, Tomasz helps founders navigate growth, product-market fit, and scaling challenges.Prior to founding Theory Ventures, Tomasz was a Managing Director at Redpoint Ventures, where he led investments in several high-growth software companies. He is widely recognized for his blog on SaaS metrics, startups, and venture capital, which serves as a valuable resource for entrepreneurs and investors alike.Tomasz holds a degree in Mechanical Engineering and Economics from Dartmouth College. His passion for technology, strategy, and helping companies succeed has made him a respected voice in the venture capital community.Theory Ventures is an early-stage venture capital firm focused on investing in transformative technology companies across sectors like SaaS, data infrastructure, AI, and machine learning. Founded by Tomasz Tunguz, Theory Ventures combines deep analytical expertise with a founder-first approach, providing hands-on support to help startups achieve product-market fit, scale operations, and drive long-term growth. The firm is committed to backing visionary entrepreneurs who are building the next generation of technology solutions, offering both capital and strategic guidance to turn bold ideas into successful businesses.Timestamps:In this episode, we discuss:* AI's Impact (1:18)* Cost Reduction in AI Training (2:18)* Impact of DeepSeek on Market Dynamics (5:01)* Open Source vs. Closed Source AI (10:57)* Enterprise Decision-Making in AI (13:19)* Defensibility of AI Applications (17:27)* Efficiency in Growing Companies (21:01)* The Path to AGI (25:46)* Impact of AI on Labor Market (28:58)* Excitement and Concerns About AI (30:55)* Non-Consensus Views on AI and Final Thoughts (33:29)I'd love to know what you took away from this conversation with Tomasz Tunguz.Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you'd like to be considered as a guest or have someone you'd like to hear from (GP or LP), drop me a direct message on X. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

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

Carl Quintanilla and Courtney Reagan broke down today's market set-up after President Trump laid out new tariff threats for 3 key industries: Autos, Pharma, and Semiconductors. Stocks under pressure as earnings from a number of sectors disappoint: Toll Brothers results hitting the homebuilders, Bumble plunging double-digits, and Etsy citing consumer headwinds… But that said: some green shoots in energy, from Solaredge to Occidental.  Within the hour: the team talked top tech picks with Wedbush's Dan Ives, fresh off a channel check in Asia; the state of the AI arms race with Logan Bartlett of Redpoint Ventures; broke down one sector still licking its wounds post-DeepSeek sell-off; and discussed Trump's decision to keep Biden-era rules around merger reviews - with one former FTC Commissioner who says that's not a bad thing.  Also in focus: Saudi-backed Future Investment Institute kicking off its “Priority Summit” in Miami, with President Trump expected to attend – David Faber brought a live read from the ground, and broke down expectations with CEO Richard Attias.  Squawk on the Street Disclaimer

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

Cyera, a data security startup, raised $300 million in a Series D funding round, increasing its valuation to $3 billion within seven months. The funding round, led by Accel and Sapphire Ventures, follows a previous $300 million Series C round that valued the company at $1.4 billion in April 2024 and a $100 million Series B round in June 2023 that valued it at $500 million. Founded in 2021, Cyera has raised a total of $760 million, with participation from Sequoia Capital, Redpoint Ventures, and Coatue in the latest round. Cyera integrates AI into its cybersecurity services to help businesses assess data security, privacy, and compliance risks. The recent funding will enhance platform development, recruit talent, and support strategic acquisitions. This fundraising event marks the largest in the cybersecurity sector this year. Learn more on this news visit us at: https://greyjournal.net/ Hosted on Acast. See acast.com/privacy for more information.

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

Andrew Rising, CEO of Encore Ventures Labs.As someone who believes deeply in the opportunity for Cleveland's future, I find Andrew's journey to be an inspiring and optimisitc one… …Deeply rooted in the heart of Cleveland's west side where he grew up before embarking on a decade-long adventure in the Bay Area—a place where innovation and venture capital converged to create world changing technologies. Andrew has spent his career at the intersection of talent and venture capital — from Google to Addepar to Redpoint Ventures — ultimately carving out a unique path that led him to co-found and successfully exit a startup to Human Capital in one of the most competitive ecosystems in the world. But despite his success on the West Coast, Cleveland was always home.In a full-circle moment, Andrew returned to his hometown in 2022, bringing with him a wealth of experience and a vision to bridge the gap between Cleveland's rich industrial heritage and its promising industrial future. Today, he's leading the charge as the founder of Encore Venture Labs, a venture studio dedicated to revitalizing the region's legacy by harnessing current macro trends with the region's unique attributes.Andrew's story is one of return, reinvestment, and a deep commitment to driving the next wave of growth in Northeast Ohio. As soon as I met Andrew, I knew one day he'd come on the podcast when the time was right, and it's exciting that time has come. I'm proud to consider Andrew a friend and am excited to share some of his reflections and experience-----LINKS:https://www.linkedin.com/in/andrewrising/https://www.encoreventurelabs.com/-----SPONSORS: John Carroll University Boler College of Business || Impact Architects & NinetyJohn Carroll University Boler College of Business: https://business.jcu.edu/ As we've heard time and time again from entrepreneurs on Lay of The Land — many of whom are proud alumni of John Carroll University —  success in this ever-changing world of business requires a dynamic and innovative mindset, deep understanding of emerging technology and systems, strong ethics, leadership prowess, acute business acumen… all qualities nurtured through the Boler College of Business!With 4 different MBA programs of study — spanning Professional, Online, Hybrid, and 1-Year-Flexible — The Boler College of Business provides flexible timelines and various class structures for each MBA Track — including online, in-person, hybrid and asynchronous — to offer the most effective options for you, in addition to the ability to participate in an elective International Study Tour, providing unparalleled opportunities to expand your global business knowledge by networking with local companies overseas and experiencing a new culture.The career impact of a Boler MBA is formative and will help prepare you for this future of business and get more out of your career. To learn more about John Carroll University's Boler MBA programs, please go to business.jcu.eduThe Boler College of Business is fully accredited by AACSB International, the highest accreditation a College of Business can have.Impact Architects & NinetyLay of The Land is brought to you by Ninety. As a Lay of The Land listener, you can leverage a free trial with Ninety, the platform that helps teams build great companies and the only officially licensed software for EOS® — used by over 7,000 companies and 100,000 users!This episode is brought to you by Impact Architects. As we share the stories of entrepreneurs building incredible organizations throughout NEO, Impact Architects helps those leaders — many of whom we've heard from as guests on Lay of The Land — realize their visions and build great organizations. I believe in Impact Architects and the people behind it so much, that I have actually joined them personally in their mission to help leaders gain focus, align together, and thrive by doing what they love! As a listener, you can sit down for a free consultation with Impact Architects by visiting ia.layoftheland.fm!-----Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.Past guests include Justin Bibb (Mayor of Cleveland), Pat Conway (Great Lakes Brewing), Steve Potash (OverDrive), Umberto P. Fedeli (The Fedeli Group), Lila Mills (Signal Cleveland), Stewart Kohl (The Riverside Company), Mitch Kroll (Findaway — Acquired by Spotify), and many more.Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/Follow Jeffrey Stern on X @sternJefe — https://twitter.com/sternjefeFollow Lay of The Land on X @podlayofthelandhttps://www.jeffreys.page/

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

Karim Atiyeh is the co-founder and CTO of Ramp, a finance automation platform that helps businesses spend less time and money. Founded in 2019, Ramp powers the fastest-growing corporate card in America and enables billions of dollars of purchases each year on the heels of nearly 10x year-over-year growth. Valued at $8.1 billion two years after launch, Ramp has raised hundreds of millions in equity from backers including Founders Fund, General Catalyst, Redpoint Ventures, Thrive Capital, D1 Capital Partners, Spark Capital, Coatue Management, Iconiq, Goldman Sachs, and Stripe. A Lebanese entrepreneur, Karim previously built and sold Y Combinator-backed Paribus to Capital One in 2016. This episode is brought to you with the support of Netsuite, download their guide at netsuite.com/scale --- Support this podcast: https://podcasters.spotify.com/pod/show/uncharted1/support

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

Today on  Equity, Devin Coldeway kicked off our Deals of the Week rundown with Piramidal, a startup which offers a foundational model for analyzing brain scan data that just raised $6 million, as his deal of the week. The premise behind the company is a fascinating one in that its technology aims to help complement the work of nurses and doctors in neural ICUs by helping identify signs of things like an epileptic episode, or a stroke.Mary Ann Azevedo wanted to talk about Comun, a neobank serving Latino immigrants in the U.S. with financial services and banking products. The fintech just raised $21.5 million a round led by Redpoint Ventures, not that long after closing its seed round. It's seeing fast growth — as well as a higher valuation.Rebecca Bellan dug into a scoop she had about Fluid Truck and recent drama there. The startup, which was founded to disrupt the commercial vehicle rental industry, has apparently ousted its sibling co-founders — CEO James Eberhard and chief legal counsel Jenifer Snyder — in what is being described as a hostile takeover.We then moved into the arrest of Telegram founder Pavel Durov, and whether or not tech executives can, and should, be held responsible for what happens on their platforms. And lastly, we dug into what's going at Inflection after Microsoft poached its co-founders. That move has drawn attention from antitrust regulators in the U.S. and U.K., who are now investigating whether Microsoft was anticompetitive. The Equity crew discussed whether or not companies are using acqui-hires to get around antitrust regulation.Honestly, we had so much fun we could've gone on for a whole other episode. Give it a listen!Equity is TechCrunch's flagship podcast, produced by Theresa Loconsolo, and posts every Wednesday and Friday. Subscribe to us on Apple Podcasts, Overcast, Spotify and all the casts. You also can follow Equity on X and Threads, at @EquityPod. For the full episode transcript, for those who prefer reading over listening, check out our full archive of episodes over at Simplecast. Credits: Equity is produced by Theresa Loconsolo with editing by Kell. Bryce Durbin is our Illustrator. We'd also like to thank the audience development team and Henry Pickavet, who manages TechCrunch audio products.

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

Larry Fitzgibbon is the co-founder and CEO of Tastemade, a global video platform with over 250 million monthly viewers. Under his leadership, Tastemade has created a vibrant community around its Food, Travel, and Home & Design programming, available across digital, mobile, streaming, and TV platforms. Larry helped raise over $130 million in venture capital from partners including Redpoint Ventures, Warner Bros. Discovery, and Amazon.Before Tastemade, Larry was a founding team member at Demand Media, leading the company through its 2011 IPO and growing its audience to over 140 million unique visitors. He also held executive roles at CitySearch and Intertainer, focusing on business development and distribution strategies.***CHA-CHING! Customers are rushing to your store. Do you have a point-of-sale system you can trust or is it (ahem) a real P.O.S.? You need Shopify for retail.Shopify POS is your command center for your retail store. From accepting payments to managing inventory, Shopify has EVERYTHING you need to sell in person. Get hardware that fits your business. Take payments by smartphone, transform your tablet into a point-of-sale system, or use Shopify's POS Go mobile device for a battle-tested solution.Plus, Shopify's award-winning help is there to support your success every step of the way.Do retail right with Shopify. Sign up for a one-dollar-per-month trial period at www.shopify.com/founderhour. Once again, go to www.shopify.com/founderhour to take your retail business to the next level today.***The Founder Hour is brought to you by Outer. Outer makes the world's most beautiful, comfortable, innovative, and high-quality outdoor furniture - ALL from sustainable materials - and is the ONLY outdoor furniture with a patented built-in cover to make protecting it effortless. From teak chairs to fire pit tables, everything Outer makes has the look and feel of what you'd expect at a 5-star resort, for less than you'd pay at a big box store for something that won't last.For a limited time, get 10% off at www.liveouter.com/thefounderhour. Terms and conditions apply. ***Follow The Founder Hour on:Instagram | www.instagram.com/thefounderhourTwitter/X | www.twitter.com/thefounderhourLinkedIn | www.linkedin.com/company/thefounderhourYouTube | www.youtube.com/@thefounderhour

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

SaaStr 746: What's Really Happening in Venture Capital Today with Redpoint Ventures Managing Director Logan Bartlett There are a lot of haves and have-nots in the software industry today. Some companies have more people throwing money at them than they know what to do with, and others are struggling to raise any money at all. Logan Bartlett, Managing Director at Redpoint Ventures, shares their yearly “State of the Market” report to understand what is and isn't happening in venture capital today. 2024 is the tale of two markets, so let's get into some of the data on today's episode. -------------------------------------------------------------------------------------------- SaaStr hosts the largest SaaS community events on the planet. Join us in 2024 at: SaaStr Annual: Sept. 10-12 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Podcast listeners can grab a discount on tickets here: https://www.saastrannual2024.com/buy-tickets?promo=fave20 --------------   This episode is sponsored by Pendo, the all-in-one product experience platform. Pendo helps your users do the things you really want them to do. You can try Pendo for free at Pendo.io/saastr and check out Mind The Product, the community for product people like… us.

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

This Week in Startups is brought to you by… Hubspot for Podcast Network. Looking to up your marketing game? Check out HubSpot's Chatbot Builder:  https://clickhubspot.com/s0u Hubspot YouTube Channel is available on all your favorite podcast apps. Chatbot Tutorial here: https://clickhubspot.com/mfx DevSquad. Most dev agencies only offer developers. Why? Because product management is hard. Get an entire product team for the cost of one US developer plus 10% off at https://www.devsquad.com/twist Mercury. 90% of startups fail. Just 10 out of every 100 make it. Mercury exists to close that gap — helping companies succeed with banking and credit cards engineered for the startup journey. Join over 100,000 companies banking with Mercury at ⁠http://www.mercury.com⁠ * Todays show: David Weisburd hosts Logan Bartlett, Hunter Somerville, and Jason Calacanis to discuss the fundraising market (3:07), M&A (26:45), Google's huge investment in generative AI (58:15), and much more! * Timestamps: (0:00) David Weisburd intros Logan Bartlett, Hunter Somerville, and Jason Calacanis (3:07) Tiger's recent fund and fundraising indicators (11:55) HubSpot's Chatbot Builder - https://clickhubspot.com/s0u https://clickhubspot.com/mfx (13:26) The challenges and realities of venture capital (25:14) DevSquad - Get an entire product team for the cost of one US developer plus 10% off at https://www.devsquad.com/twist (26:45) Startup acquisitions, due diligence, and unethical behaviors in the industry (31:27) Selling partial positions in startups and structuring the selling of shares (37:18) Mercury - Join 100K+ startups banking with Mercury at http://www.mercury.com⁠ (38:20) Cendana and Kline Hill's $105M fund to buy stakes in seed VC funds (46:59) The correlation between capital consumption and equity value, and the dangers of excess capital (54:28) The role of private equity in tech M&A and the future of tech IPOs (58:15) Google's $100 billion investment in AI and competition in the AI ecosystem (1:06:30) The challenge of capacity in seed stage investing and the value of a strong community in portfolio management * Follow Logan: X: https://twitter.com/loganbartlett LinkedIn: https://www.linkedin.com/in/loganbartlett Check out: https://www.redpoint.com * Follow Hunter: LinkedIn: https://www.linkedin.com/in/hunter-somerville-2a24117 Check out: https://www.stepstonegroup.com/ * Follow David: X: ⁠https://twitter.com/DWeisburd⁠ LinkedIn: ⁠https://www.linkedin.com/in/dweisburd⁠ Check out: ⁠https://10xcapital.com * Follow Jason: X: ⁠https://twitter.com/jason⁠ Instagram: ⁠https://www.instagram.com/jason⁠ LinkedIn: ⁠https://www.linkedin.com/in/jasoncalacanis * Thank you to our partners: (11:55) HubSpot's Chatbot Builder - https://clickhubspot.com/s0u https://clickhubspot.com/mfx (25:14) DevSquad - Get an entire product team for the cost of one US developer plus 10% off at https://www.devsquad.com/twist (37:18) Mercury - Join 100K+ startups banking with Mercury at http://www.mercury.com⁠ * Check out the Launch Accelerator: https://launchaccelerator.co * Check out Founder University: https://www.founder.university * Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp * Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland * Check out Jason's suite of newsletters: https://substack.com/@calacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups * Subscribe to the Founder University Podcast: https://www.founder.university/podcast