Founded & Funded

In the latest episode of Founded & Funded, Madrona Partner Vivek Ramaswami sits down with Harley Sugarman, founder and CEO of Anagram, to unpack how one pivot, a flood of cold outreach, and relentless focus on behavior change transformed a niche tool into an enterprise platform serving companies like Disney and Pfizer.   From landing enterprise logos off of nothing but wireframes, to outmaneuvering the 800-lb gorilla in a legacy industry — Harley's tactics are a masterclass for any founder trying to stand out in a crowded market. Transcript: https://www.madrona.com/how-anagram-landed-disney-with-cold-outbound-security-awareness-training Chapters:  (00:00) Introduction (01:53) Harley Sugarman's Background and Journey (03:24) Founding Anagram (04:21) Initial Vision and Pivot (05:50) Challenges and Market Realities (06:54) Customer Feedback and New Direction (09:25) Executing a Startup Pivot (11:31) Cold Outreach Success (14:20) Security Awareness Training that works (18:52) Competing in a Crowded Market (24:48) Enterprise Sales Strategy (27:04) Fundraising Journey (28:54) Choosing the Right Investors (33:32) Advice for Founders (36:33) Future of Security Training

What happens when a scientist becomes a VC? We sat down with Madrona’s Joe Horsman to find out. In this episode, Joe shares his journey from late nights in the lab to helping biotech founders bring life-changing science to market. You’ll hear: Why Seattle’s biotech + AI ecosystem is heating up What founders need beyond funding to commercialize world-changing science. Why weekend adventures fuel Monday creativity

In this Founded & Funded episode, Madrona Managing Director Soma Somasegar sits down with Charles Lamanna, Corporate Vice President at Microsoft, to unpack his journey from startup founder to corporate leader. They dive into what it takes to build a successful AI-transformed organization, how the nature of business applications is evolving, and why AI agents will fundamentally reshape teams, tools, and workflows. From "customer obsession" to "extreme ownership," Charles delivers insight after insight for startup founders and enterprise leaders navigating the age of AI. They dive into: Why business apps as we know them are dead How AI agents and open standards like MCP and A2A are reshaping software The shift toward generalist teams powered by AI What startups are doing today that enterprises will follow in 3–5 years How to focus deeply on a few high-impact AI projects instead of chasing 100 pilots Transcript: https://www.madrona.com/the-end-of-biz-apps-ai-agility-and-the-agent-native-enterprise-from-microsoft-cvp-charles-lamanna Chapters: (00:00) Introduction (01:20) Charles Lamanna's Entrepreneurial Journey (01:39) Customer Obsession and Ownership in Startups (03:54) The Future of Business Applications with AI (05:56) AI-Powered Business Agents (08:22) The Role of AI in Modern Business (11:11) Startups Are the Blueprint for the Future of Work (14:33) Industry-Wide AI Adoption (18:32) Driving AI Transformation in Enterprises (21:51) Maintaining Agility in Large Companies (25:03) Personal Impact of AI on Daily Life (27:55) Conclusion and Final Thoughts

Entrepreneurs often ask: When do I know it’s time to scale? Or, how do I lead when I wasn’t the original founder? In this week’s Founded & Funded, Madrona Partner Chris Picardo sits down with Eleanor Lightbody, CEO of Luminance, who shares how she took a promising AI product and built a company culture, go-to-market motion, and product strategy that’s scaled 6x in just two years. Eleanor’s candor and tactical insights on hiring, selling, and navigating founder dynamics make this a must-listen. Transcript: https://www.madrona.com/building-ai-that-sells-scaling-smarter-with-luminance-ceo-eleanor-lightbody/ Chapters: (00:00) Introduction (01:29) Eleanor's Career Journey (03:22) Joining Luminance and Initial Challenges (05:46) Navigating CEO Role and Company Dynamics (11:01) Transforming Luminance's Growth Trajectory (19:03) Balancing Innovation and Core Product Delivery (24:42) Building a Collaborative Culture (28:44) Challenges and Rewards of Scaling a Company (34:57) Future of AI

Most startups bolt AI onto old products.  ⁨@ravennahq⁩  reimagined the entire workflow.  When we first met Kevin Coleman and Taylor Halliday, it was clear they weren’t just chasing the hype cycle. They were pairing AI-native architecture with deep founder-market fit, and rebuilding how internal ops work — from first principles. Their new company, Ravenna, is going after a $160B+ market dominated by legacy players. But instead of being intimidated by incumbents, they got focused, making some smart moves that more early-stage teams should consider: 1) Speak with 30+ customers before writing a line of code 2) Define a clear ICP and pain points 3) Build natively for Slack — where support actually happens 4) Prioritize automation, iteration, and real workflow transformation 5) Stayed radically transparent with investors and early customers At Madrona, we love backing teams that combine ambition with discipline — and Kevin and Taylor are doing just that. In this episode of Founded & Funded, they sit down with Madrona Managing Director Tim Porter and talk through their journey, what they’d do differently the second time around, and how they’re building a durable, agentic platform for internal support. If you're a founder building in AI, SaaS, or ops — this conversation is full of lessons worth hearing. Transcript: https://bit.ly/4ju2Cml Chapters:  (00:00) Introduction (00:23) Meet the Founders: Taylor Halliday and Kevin Coleman (02:05) The Birth of Ravenna: Identifying the Problem (03:05) The Concept of Enterprise Service Management (04:02) The Journey from Idea to Execution (04:31) Customer Insights and Market Fit (06:42) Building a Next-Generation Platform (10:43) Slack Integration and AI Automation (14:37) Partnering with Slack: A Strategic Move (17:13) Leveraging Slack for Knowledge Management (20:13) Balancing Focus and Vision (21:07) Discovering ITSM: A Hidden Market (21:40) Expanding Beyond IT: The Universal Help Desk (24:30) ServiceNow and the AI Revolution (27:03) Building a Transparent and Collaborative Culture (29:37) Recruiting Top AI Talent (31:59) Navigating Market Realities and Customer Focus (37:59) Advice for Aspiring Founders

In this episode of Founded & Funded, Madrona Managing Director Soma Somasegar sits down with Anoop Gupta, co-founder and CEO of  @SeekOut    — an AI-first company transforming how organizations discover, hire, and manage talent. They explore: 1) SeekOut’s evolution from LLM-powered workflows to the launch of SeekOut Spot, their agentic AI solution that delivers hires in as little as 3 days. 2) Why "service as software" is the future of recruiting. 3) How founders and talent leaders can reimagine hiring in the age of AI agents. 4) Lessons from building an AI-native company through market shifts. 5) The real business model shift from tools to outcomes. With customers like Discord, 1Password, HP, and even Madrona itself, SeekOut is redefining what fast, high-quality hiring looks like. Transcript: https://madrona.com/rise-of-agentic-ai-in-recruiting-seekout-anoop-gupta Chapters: (00:00) Introduction (01:56) SeekOut Background and AI Evolution (03:55) The Role of Agentic AI in Recruiting (07:59) Business Model and Flexibility (12:59) Recruiting Process and Efficiency (16:49) Navigating Challenges and Product-Market Fit (20:29) Focus on Outcomes not on Hype  (22:25) Do you Need a Data Moat? (23:45) Don't build a recruiting org too early (25:50) The biggest hiring mistakes (29:15) Agentic AI for recruiting is here

This bonus episode of Founded & Funded is a follow-up to Madrona Partner Jon Turow's conversation with Douwe Kiela, CEO of Contextual AI and co-inventor of RAG. In this quick chat, they dive into: 1) Why storytelling—not just GTM—needs to be vertical2) How to build a platform by showing what’s possible3) The tension between “doing one thing well” vs. building the whole stack 4) Multimodal content moderation at Meta & what it taught Douwe This 10-minute post-show chat is a must-listen for founders thinking deeply about where to plant your flag — and when to break the rules.

​Microsoft Chairman & CEO Satya Nadella sat down with Madrona Managing Director Soma Somasegar at Madrona’s 2025 Annual Meeting to discuss the key inflection points in his leadership journey, Microsoft’s AI strategy, and the massive economic impact AI will have on the world. From redefining company culture to betting big on AI and OpenAI,Satya shares deep insights into Microsoft’s transformation — and what’s next. Watch now for leadership lessons, AI predictions, and the future of innovation! Transcript: https://www.madrona.com/satya-nadella-microsfot-ai-strategy-leadership-culture-computing Chapters: (00:00) Introduction (03:34) Satya Nadella's Journey as CEO  (09:57) Cultural Transformation at Microsoft (14:03) The Influence of Cricket on Leadership (18:27) The AI Revolution and Microsoft's Role (28:30) The Future of AI and Economic Impact

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