Founded & Funded

Fyxer.ai is an AI-powered assistant that helps users reclaim hours of their day by managing their inboxes, writing replies, and taking meeting notes. But Fyxer didn’t start with AI. It started with a decade-long executive assistant agency that gave them a treasure trove of data and insight that became the foundation for integrating AI. Fyxer CEO and Co-Founder Rich Hollingsworth joins Madrona Managing Director Karan Mehandru on this episode of Founded & Funded to share how Fyxer went from $1M to $10M ARR in six months with just 30 employees. In this episode, Rich shares: Why great startups start with real-world pain How there is still room for disruption with email Why quality data matters more than quantity The PLG-to-enterprise playbook that actually works The rowing team mindset that drives their decision-making Whether you're a founder, operator, or investor, this is a masterclass in AI execution, startup focus, and scaling fast without breaking. Full Transcript: www.madrona.com/fyxer-ai-productivity-tools-for-email-and-meetings Chapters (00:00) Intro  (01:00) From EA Agency to AI Assistant (03:00) Lessons from Building Workflow-Driven AI (04:00) Growth: $1M to $10M ARR in 6 Months (05:00) Planning for Success vs. Failure (06:00) Frameworks for Prioritization (07:00) PLG + Enterprise Motion (09:00) What's Broken in AI Productivity (10:00) The Quality of Data Edge (12:00) Hiring: Execs Who Do the Grunt Work (14:00) Building with Family: Founding with His Brother (16:00) The Co-Founder Pitch That Landed Matt (18:00) What Startups Get Right vs. Big Tech (19:00) Founder Self-Work: Execution vs. Promotion (20:00) The Kindest Thing

Thompson and Austin Hay, co-founders of Clarify, the startup that’s pioneering the idea of autonomous CRM. Their vision? A CRM that actually does the work for sellers of driving outreach, managing pipeline, and surfacing insights without constant manual input. Patrick and Austin share: • Their journey from Iteratively, Ramp, and Amplitude to founding Clarify • Why the CRM market is ripe for disruption with AI • How Clarify’s unique pricing model flips the script (free CRM, pay only when the AI agent works for you) • The concept of autonomous GTM teams and the rise of the Go-to-Market Engineer • Lessons in building culture, hiring talent, and embracing the “beautiful mess” of startups If you’re a founder, sales leader, or builder rethinking your revenue stack and curious about how AI will transform the way teams sell, this conversation is a must-listen. 👉 Subscribe for more conversations with founders and leaders shaping the future of technology. Full Transcript: www.madrona.com/autonomous-crm-how-clarify-is-reinventing-a-100b-category Chapters:  (00:00) - Introduction (01:33) - What is Clarify? Tackling CRM Frustrations (02:11) - Lessons from Previous Startups and the CRM Problem (03:47) - Applying CDP Lessons to CRM (04:56) - Why Now? The Opportunity in CRM and AI (05:24) - Overcoming Legacy Systems and the Joy of New Tools (07:04) - Product Vision: Reducing Friction and Increasing Joy (08:44) - Business Model Innovation: Usage-Based Pricing (10:52) - Autonomous CRM: What Does It Mean? (12:12) - How Clarify’s AI Agents Work in Practice (14:35) - All-in-One vs. Best-of-Breed: Customer Feedback (16:09) - Autonomous GTM: The Rise of the Go-To-Market Engineer (18:17) - Data Strategy: Intent Data and Customer Insights (20:37) - Structuring Data for Automation and Analytics (22:10) - Team and Culture: Hiring and Building for Success (24:30) - Lessons in Leadership and Relationship Building (25:50) - The Future of Go-To-Market Teams (27:00) - Advice for Founders (28:32) - Embracing the Messiness of Startups

Rolanda Fu, an investor at Madrona, has a fascinating journey from playing violin at weddings to evaluating dynamic startups. She discusses the vibrant investment ecosystem in Seattle and emphasizes the advantages of a generalist perspective in venture capital. Rolanda shares what traits she values in entrepreneurs, especially in the AI-first landscape. Her insights provide founders with a clear understanding of what makes them stand out, making this a must-listen for anyone looking to navigate the VC world.

In this episode of Founded & Funded, Madrona Partner Vivek Ramaswami sits down with Jared Palmer — designer, developer, and founder of Turborepo (acquired by Vercel), and former VP of AI at Vercel. Jared walks through his unique path from Goldman Sachs to Vercel, and how he combined finance, design, and engineering to create beloved developer tools like Formik, TSDX, and Turborepo, and v0. The two dive deep into: Why vertical integration is the future of AI-native dev platforms The founding and launch of Vercel’s v0.dev How Vercel is positioning for a world with 700M code-generators, not just 28M developers What makes teams and products move fast Why “text-to-app” will soon become “text-to-business” Whether you're a founder building dev tools, a product leader thinking about AI-native apps, or a developer curious about the future of your craft — this episode is packed with lessons and foresight. Subscribe and listen now! Transcript: https://bit.ly/4kQWVig Chapters:  (00:00) Introduction (01:40) Jared Palmer's Early Career in Finance (04:40) Transition to Design and Freelancing (07:12) Building a Career in Open Source (11:46) Creating TurboRepo (13:47) Joining Vercel (15:27) Adjusting to Corporate Life (17:37) The Power of Transparency in Teams (17:50) Building a Thriving Team Environment (19:08) Origins of v0 (19:29) Early Development and Challenges (21:38) Key Innovations and Prototypes (22:58) Launch and Rapid Growth (25:32) Navigating a Competitive Landscape (30:02) Future of AI and Software Development

In this episode of Founded & Funded, Madrona Investor Rolanda Fu is joined by Dedy Kredo, the co-founder and chief product officer of QodoAI — formerly CodiumAI, a 2024 IA40 winner and one of the most exciting AI companies shaping the future of software development. Dedy and his co-founder, Itamar, are entrepreneurs who have spent their careers building for developers, and with Qodo, they're tackling one of the most frustrating problems in software engineering — testing and verifying code. As AI generates more code, the challenge shifts to ensuring quality, maintaining standards, and managing complexity across the entire software development lifecycle. In this conversation, Dedy and Rolanda discuss how Qodo's agentic architecture and deep code-based understanding are helping enterprises leverage AI speed while ensuring code integrity and governance. They get into what it takes to build enterprise-ready AI platforms, the strategy behind scaling from a developer-first approach to major enterprise partnerships, and how AI agents might reshape software engineering teams altogether. Transcript: https://www.madrona.com/engineering-ai-era-qodo-dedy-kredo-on-ai-powered-sdlc Chapters:  (00:00) Introduction  (01:12) The Future of AI in Software Development (01:58) Dedy's Journey in Tech (03:02) The Genesis of Qodo (03:53) Qodo's Unique Approach to AI Coding (05:13) Exploring Qodo's Product Features (06:42) Code Review and Verification (08:53) Customizing AI Agents (11:02) Vibe Coding and Code Review (13:27) Developer Love vs. Enterprise Needs (15:33) Enterprise Adoption (17:51) Future of Software Engineering (22:13) Balancing Developer Love and Enterprise Sales (24:05) Advice for Founders 

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