Douwe Kiela, co-founder and CEO of Contextual AI and co-inventor of Retrieval-Augmented Generation (RAG), shares insights on revolutionizing AI systems for enterprises. He dives into the origins of RAG, its often-misunderstood role, and the critical innovations at Contextual AI. Douwe discusses the importance of addressing hallucinations in AI, how to align AI with business value, and offers advice for founding AI companies. He emphasizes the need for adaptability in entrepreneurship and outlines the challenges of successfully deploying AI technologies.

The security industry has a math problem: 12 million job postings, only 7 million qualified professionals. The solution? AI. Edward Wu spent nearly a decade at ExtraHop, pioneering AI-driven security detection. But instead of just alerting security teams about potential threats, he saw a bigger opportunity — what if AI could act as an actual security analyst? That question led to Dropzone, a company that’s not just throwing AI at security but strategically using it to solve one of the most overwhelming problems in the industry — alert fatigue. In this episode of Founded & Funded, Edward and Partner Vivek Ramaswami dive into: The "aha moment" that led Edward to leave a successful career to start Dropzone  Why most AI security startups will fail, and what it takes to stand out How Dropzone landed UiPath as a customer—without a single cold email  The future of security in an AI-first world Watch/Listen to the full conversation for insights from Edward on what it takes to build in one of the most competitive categories in security today. Transcript: https://www.madrona.com/dropzones-edward-wu-security/   Chapters:  (00:00) Introduction (01:40) Edward Wu's Journey into Security (02:48) The ExtraHop Experience (05:10) The Leap to Entrepreneurship (07:59) The Aha Moment: Founding Dropzone (10:28) AI's Role in Security (16:30) Navigating the Competitive Landscape (19:15) Marketing and Customer Acquisition Strategies (21:30) Landing a big-name customer without cold outreach (25:40) Push v. pull when selling into security (28:25) ChatGPT was startups' greatest marketing gift (30:18) Lessons Learned as a Solo Founder

Jonathan Frankle, Chief AI Scientist at Databricks and co-founder of Mosaic ML, shares his insights on transforming AI hype into practical solutions. He discusses the crucial mistake AI startups make when selling to enterprises and how to bridge the gap between research and market needs. Frankle emphasizes the importance of effective storytelling and adapting AI systems to customer requirements. He also highlights opportunities often overlooked by startups and how early wins at Mosaic ML can inform future directions in AI and data intelligence.

Thinking about leaving Big Tech for a startup? In this episode of Founded & Funded, Madrona Managing Director Tim Porter sits down with Bhrighu Sareen, who took the leap from Microsoft to Highspot and has been leading AI-driven product innovation ever since. They talk about the realities of transitioning from a massive company to a high-growth startup, scaling AI-driven teams, and how Bhrighu’s helping transform sales enablement through automation and intelligence.  His insights on navigating change, working with founders, and executing at speed are a must-listen for any leader considering the leap from stability to startup chaos. Tune in now for practical strategies and an inside look at how AI is reshaping go-to-market execution.  Transcript: https://www.madrona.com/big-tech-to-startups-highspot-bhrighu-sareen Chapters: 00:00 Introduction 03:01 Bhrigu Sareen's Journey at Microsoft 06:52 Transition to Highspot 10:00 Working with Founders and Building Trust 16:31 Increasing Product Velocity and Efficiency 21:12 Cross-Team Dependencies and Offshore Strategies 23:02 Starting the Journey at Highspot 23:31 Navigating Economic Uncertainty 24:21 Expanding Talent Pool in Vancouver 25:37 Establishing a Development Center in India 27:54 Challenges and Surprises in Transition 29:50 Innovating Through Economic Challenges 31:01 HighSpot's AI and ML Innovations 33:03 AI-Powered Sales Training and Coaching 36:14 Future of AI in Sales and Marketing 43:31 Balancing Data and User Experience 47:28 Looking Ahead: AI Agents and Productivity Gains

What does it take to go from engineer to founder, from startup CEO to scale CEO? In this special live episode of Founded & Funded, Madrona Managing Director Karan Mehandru sits down with Mohit Aron, founder of Nutanix and Cohesity, to uncover the lessons behind his success. Mohit shares his unique hiring strategy, how to identify product-market fit, and the power of balancing vision with execution. Whether you’re navigating your first company or scaling your third, Mohit’s advice is a masterclass in resilience, grit, and building a legacy. Full Transcript: https://bit.ly/42xnyD9 Chapters:  (00:00) Introduction  (02:04) Traits of Successful Founders  (05:03) Challenges in Transitioning from CTO to Startup CEO to Scaling CEO  (07:51) Effective Hiring Strategies (13:42) Defining Product-Market Fit 15:55 Balancing Vision and Focus  (17:48) The Importance of a Bigger Vision  (20:12) The Role of a CEO Post Product-Market Fit  (22:00) Delegation and Leadership Strategies  (24:23) Generative AI: Hype vs. Reality  (27:09) Crafting a Vision and Minimum Lovable Product  (28:56) Choosing the Right Investors and Building a Board  (32:15) Framework for Startup Success

Terray Therapeutics CEO Jacob Berlin returns to Founded & Funded after three years to share how the company has scaled from an ambitious startup to an industry leader in AI-driven biotech. Learn how Terray's proprietary hardware combined with the world's largest chemistry data set is powering new discoveries in small molecule drug development.  Jacob also discusses how the company’s $120M Series B fundraise will prepare their internal programs for clinical trials and further enhance their AI platform. He shares insights on where he sees the future of AI and drug design and dives into how founders can balance internal innovation and high-profile partnerships. Don’t miss this deep dive into the intersection of AI, biotech, and innovation! Transcript: https://www.madrona.com/terray-jacob-berlin-on-the-ai-powered-future-of-medicine Chapters: (00:00) Introduction 00:39 The Evolution of Terray Therapeutics (02:08) Understanding Small Molecule Therapies (04:12) The Journey of Data and AI (07:58) Series B Fundraise and Future Plans (11:20) Biotech Platform vs. Product Debate (14:20) Building a Long-Term Vision (16:39) Deep Dive into Terray’s AI and Science (36:05) The Importance of Partnerships (39:20) High-Performance Culture at Terray

Imagine a future where healthcare isn’t just reactive but deeply personalized — where every patient gets the right treatment at the right time based on a precise understanding of their biology. This is the future Ovation is building, and on this week’s Founded & Funded, Madrona Partner Chris Picardo dives into it all with Ovation CEO Curt Medeiros. From transforming underutilized clinical data into rich multiomics datasets to forging industry-leading partnerships with companies like Illumina, Curt shares how Ovation is shaping the future of precision medicine. He also opens up about the challenges of building a scalable, privacy-first platform, the lessons he’s brought from leading large healthcare businesses, and why collaboration and diversity are key to solving complex problems in healthcare. Transcript: https://www.madrona.com/curt-medeiros-on-revolutionizing-precision-medicine-and-scaling-ovation Chapters: (00:00) Introduction (01:32) Ovation's Role in Precision Medicine(03:17) The Importance of Data in Precision Medicine(06:12) Challenges and Opportunities of Genomic Data (11:17) Privacy and Pharmaceutical Applications (16:42) Ovation's Unique Approach and Partnerships (17:00) Expanding Research Beyond Pharma(18:28) Recent Successes and Future Plans(26:36) Curt Medeiros' Journey to Ovation(29:56) Leadership Philosophy and Company Culture(33:21) Future of Precision Medicine

Marc Osofsky, CEO of Jama Software, shares insights on transforming Jama from a $20M ARR company to a $1.2 billion acquisition success. He discusses intentional strategies that challenge traditional growth norms, emphasizing improving win rates over rapid sales team expansion. Marc advocates targeting activated market demand instead of just size and reveals insights on achieving profitable growth to attract financial sponsors. He also highlights the importance of cultivating a high-performance culture focused on efficiency and customer success.

What does it take to move from cutting-edge academic research to launching a biotech company that could transform medicine? In this week’s episode of Founded & Funded, Madrona Partner Chris Picardo sat down with Jamie Lazarovitz, CEO and co-founder of Archon Biosciences, to uncover the story behind their groundbreaking protein-based biologics and their unique Antibody Cages (AbCs). From bootstrapping deep tech investments as a student to navigating the challenges of commercializing revolutionary science, Jamie shares the pivotal moments, tough decisions, and key lessons that led to Archon’s creation. This isn’t just a story for biotech enthusiasts — every founder can take away valuable insights on: 1) Asking for help and building teams with complementary skills — no founder succeeds alone. 2) Applying AI thoughtfully — it’s a tool, not a magic wand. 3) Patience — ensure your foundation is strong before scaling. 4) Partnering with investors you trust and who align with your mission. 5) Setting a high bar for talent and culture — great people build great companies. 6) Communicating your differentiation — make your value clear to all stakeholders. Full Transcript: https://www.madrona.com/archon-unlocks-antibodies-with-ai-jamie-lazarovits Chapters: (00:00) Introduction  (00:55) Jamie Lazarovitz's Journey from Deep Tech to Biotech (01:45) Early Ventures and Lessons Learned (05:03) The Motivation Behind Jamie’s Biotech Passion (07:40) Joining the Institute for Protein Design - David Baker (09:40) Meeting Co-Founder George Ueda and the Birth of Archon (12:46) Revolutionary Protein Design at Archon: Antibody Cages (AbCs) (25:23) The Role of AI in Protein Design (27:50) Building a Successful Biotech Company (38:47) Future Prospects

In this episode of Founded & Funded, Madrona Managing Director Karan Mehandru hosts Brian Raymond, founder and CEO of 2024 IA40 winner Unstructured. Unstructured turns raw, messy, unstructured data into something AI tools can actually process — a typically expensive and time-consuming process for companies hoping to save money with the tools themselves. Brian and Karan explore some of the biggest trends in AI, including moving from prototype to production, the rise and fall of vertical applications, the shift toward powerful horizontal solutions, whether the ROI will be there on all this capital investment into AI, and the trough of disillusionment and why expectations in AI often don't match reality. They also discuss how an unlikely source, the public sector, is driving AI innovation today. It's a conversation you won't want to miss. Full Transcript: https://www.madrona.com/prototype-to-production-ai-insights-unstructured-brian-raymond Chapters: (00:00) Introduction  (01:14) Trends in AI: From Vertical to Horizontal Solutions  (01:47) The First Mile of AI: Preprocessing and Data Ingestion  (03:43) Displacement of knowledge graphs for RAG  (06:19) The AI Stack: Layers and Competition  (08:55) Is the current level of investment in AI justified?  (11:19) The Speed of Change in AI(12:47) Public Sector vs. Private Sector Roles in AI Innovation(16:52) "Two completely incongruous narratives"(19:15) Advice for AI Entrepreneurs(21:49) Unstructured's Future