Founders in Arms

• Inside David Gu’s $38M Raise: The Pivot That Put Recall.ai on the Map

  David Gu is the co-founder and CEO of Recall.ai, building conversation recording infrastructure that powers over 1,000 AI companies. Fresh off announcing a $38 million Series B led by Bessemer, David shares the journey from a Winter 2020 Y Combinator call recording tool to becoming the backbone of AI conversation intelligence.What you'll learn:How David pivoted from application to infrastructure after spending 80% of engineering time on recording problemsWhy the social shift toward recording acceptance created a massive infrastructure opportunityThe systematic approach David used to learn enterprise sales with zero experienceHow Recall's desktop recording SDK eliminates the need for bots in meetingsWhy Series B fundraising still requires a 100x growth vision even at scaleThe framework David uses to validate new products and channels before investing timeHow Amanda Gu built 45,000 LinkedIn followers and turned social media into a lead generation engineWhy David records and reviews every sales pitch to improve his closing rateThe mental shift from seeking external validation to embracing continuous failureHow the conversation data revolution will transform every B2B software applicationIn this episode, we cover:(00:00) Introduction and David's Y Combinator background(01:30) Announcing Recall.ai's $38M Series B funding round(03:18) The pivot from call recording app to infrastructure platform(09:42) Why recording infrastructure became their nightmare and salvation(15:36) Learning enterprise sales as a technical founder(22:13) Amanda's LinkedIn growth and social media lead generation(28:26) Systematic approach to testing new products and channels(34:52) Why Series B still requires 100x vision and growth story(42:17) The social transformation that made recording acceptable(48:23) Working seven days a week for three years in the early days(53:05) The framework for embracing failure as a learning tool

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• Building and Selling in "Impossible" Markets with WePay's Bill Clerico

  Bill Clerico is the founder and former CEO of WePay, which he sold to JPMorgan Chase for $400 million, and is now founding managing partner of Convective Capital, investing in wildfire risk management and physical resilience technologies. Starting WePay during the 2008 financial crisis when VCs said "no one makes money in payments except PayPal," Bill built one of the pioneering fintech companies alongside Stripe and Square.What you'll learn:Why VCs avoiding entire sectors often signals the biggest opportunitiesThe unconventional partnership strategy that led to WePay's $400M JPMorgan acquisitionHow to position strategic partnerships as pathways to acquisition rather than just revenueWhy WePay's delayed pivot from consumer to developer APIs cost them market leadershipThe specific tactics for getting enterprise buyers excited about acquisition vs. partnershipsHow to navigate the early fintech landscape without established banking infrastructureWhy timing strategic decisions matters more than perfecting the original planThe 12-18 month timeline required for enterprise acquisition conversationsHow crisis-driven industries create first-time openings for technology adoptionBill's contrarian thesis on investing in utilities, insurance, and government sectorsIn this episode, we cover:(00:00) Introduction and Bill's journey from investment banking to entrepreneurship(08:13) Starting WePay during the 2008 financial crisis in Boston(12:00) Getting into Y Combinator and the early pivot struggles(17:37) The acquisition strategy and JPMorgan partnership approach(24:38) Lessons on founder burnout and sustainable company building(36:19) Convective Capital's thesis on physical risk management(42:38) Building an insurance company for high-risk California properties(46:35) The future of wildfire risk and climate resilience investing

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• Frugality, Grit, and Scale: Inside Joris Poort’s Founder Playbook

  Joris Poort is the CEO of Rescale, a digital engineering platform that provides supercomputing capabilities for engineers and scientists designing rockets, drugs, and computer chips. Starting from Y Combinator in 2012, Rescale has grown over 14 years to serve major aerospace and life sciences companies with over 200 employees and a platform that combines high-performance computing with AI physics capabilities.What you'll learn:Why "Default Alive" means cash flow positive, not just having runway or theoretical profitabilityHow to avoid false trade-offs by asking "why not both?" instead of accepting either/or decisionsWhy the biggest startup mistakes are always people, especially bad executive hiresThe hidden advantages of grinding through difficult early years versus overnight successHow to maintain frugal company culture while scaling from 4 to 200+ employeesStrategic approaches to long-term R&D investments, including AI physics and Department of Defense contractsThe difference between executives who built systems versus those who just ran themWhy promoting internal talent often works better than external executive hiresHow to structure resource allocation decisions to force proper prioritizationThe psychology of founder endurance and why some businesses are intentionally harder to buildIn this episode, we cover:(00:00) Introduction to Joris Poort and Rescale(01:04) Meeting Raj at Paul Graham's place in England(04:36) What Rescale does: supercomputing platform for engineering(08:02) How modern AI impacts scientific computing and physics(12:31) Building for 15 years: the ups and downs of long-term company building(14:20) The moment of becoming "Default Alive" and what it really means(16:49) VCs versus founders on spending and growth philosophy(22:03) Implementing frugal culture and budget discipline at scale(26:56) The challenge of promoting internal talent to executive roles(32:28) Interviewing every hire up to 200 people and building relationships(34:30) Rapid fire: riskiest bets, biggest mistakes, and hard-won lessons(42:31) AI investments, Department of Defense contracts, and strategic moats(48:45) Why the hardest path often creates the strongest business

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• Building in Defense Tech and Sovereign AI with Mattermost's Ian Tien

  Ian Tien is the co-founder and CEO of Mattermost, an open-source collaboration platform that has evolved from a Slack alternative to essential infrastructure for government and defense organizations worldwide. Starting from a failed HTML5 gaming platform at Y Combinator, Mattermost now serves over 4,000 contributors, employs 120 people, and operates profitably while powering sovereign collaboration for national security agencies.What you'll learn:How Mattermost pivoted from gaming to defense tech through bottom-up adoptionThe concept of "sovereign collaboration" and why governments need independent AI systemsIan's framework for hiring executives with "scar tissue" from diverse experiencesWhy he regrets spending $270,000 on internal swag after taking VC moneyThe unique language and procurement challenges of selling to government customersHow open source enables PLG motion in highly secure environmentsThe difference between "butts and seats" contracting vs. commercial off-the-shelf solutionsWhy most successful founders are in their 30s and 40s, not college dropoutsIan's "daddy daughter days" approach to work-life balance as a CEOThe emerging landscape of sovereign AI and national security technologyIn this episode, we cover:(00:00) Introduction and Ian's Tools for Tech Leaders podcast(04:05) Mattermost's evolution from Slack alternative to sovereign collaboration(08:09) Bottom-up adoption in national security environments(14:23) Learning to sell to government customers and navigate defense acronyms(24:49) Executive hiring philosophy and building long-term relationships(30:47) The sovereign AI landscape and government investment trends(38:53) Defense tech opportunities and getting started in the space(42:57) Palantir's business model and government contracting dynamics(51:18) Rapid fire: Walt Disney as tech founder inspiration and personal lessons

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• Building Enterprise AI That Actually Works with Glean's Arvind Jain

  Arvind Jain is the founder and CEO of Glean, building enterprise AI that connects to all internal company data, and co-founder of Rubrik, which recently went public. Starting as an enterprise search company in 2019, Glean has evolved into what Arvind calls "a more powerful version of ChatGPT inside your company," now approaching 1,000 employees and serving the world's most iconic companies.What you'll learn:How Glean evolved from search to conversational AI without pivoting by riding AI model capabilitiesWhy making it easy for customers to leave can be a competitive advantage in enterprise salesThe challenges of competing against every major software company building similar productsHow to recruit from FAANG companies when you can't match their compensationThe difference between building for established markets vs. creating new product categoriesWhy enterprise buyers are tired of AI overpromising and prefer honest positioningHow to stay close to product development while scaling to 1,000 employeesThe transition from Google engineer to startup co-founder and the skills you have to relearnWhy customer success and shared roadmaps are critical for complex AI implementationsThe decision framework for staying independent vs. acquisition when building at scaleIn this episode, we cover:(00:00) Introduction to Arvind Jain and his journey from Rubrik to Glean(01:27) Lessons learned building two different types of enterprise companies(03:09) How Glean works as enterprise search and AI assistant(06:00) The natural evolution from search to conversational AI(08:00) Navigating the AI hype cycle and competitive landscape(11:04) Competition strategy and staying ahead of major software companies(16:40) Honest positioning vs. overpromising in AI sales(20:01) Building enterprise reputation and customer relationships(24:41) Motivation for continuing to build after previous success(26:56) Staying close to product at scale and avoiding bottlenecks(31:08) Using Glean internally and rapid iteration cycles(32:18) The decision to stay independent vs. acquisition(37:24) Transition from Google to startup founder(43:45) Rapid fire questions and leadership lessons(48:31) Uncomfortable feedback about constraining team speed

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