Building the AI Insurance Giant From Scratch

They didn’t sell to insurance brokers — they replaced them. Dakotah Rice didn’t build AI tools for the industry. He built an AI-first insurance company — and now Harper is scaling faster than they can handle. In this episode, Dakotah shares how Harper went from kitchen-table experiments to a high-growth, fully autonomous insurance brokerage. He breaks down the real bottlenecks, the AI architecture behind their workflows, and the bold bets that could reshape an entire industry. What you’ll learn: Why Harper ditched SaaS and chose vertical integration How to embed engineers directly in operational workflows The underrated bottlenecks to AI-first company scaling Why relationships are overrated in insurtech How to build trust with real-world customers — without mentioning AI The real limits (and future) of fully autonomous firms 📌 Watch now and subscribe for more smart, fast, founder-first interviews. Chapters 00:00 Introduction to Harper and Dakota Rice 00:38 Dakota's Background and Harper's Mission 02:13 Challenges and Pivots in Building Harper 04:29 Entering Y Combinator and Scaling Up 06:19 The Importance of Workflow Understanding 13:17 Lessons from Past Failures 18:34 Vision for AI in the Future 21:51 Building Complex AI Systems 22:49 Human Element in AI Services 23:53 Customer Perception of AI 27:37 Scaling Challenges and Solutions 35:14 AI's Role in Future Business Models 37:58 Future Predictions and Industry Insights 42:46 Conclusion and Contact Information 🎧 Listen on the go: Spotify: https://spoti.fi/4m2K7ah Apple: https://apple.co/4cZ8RMm My other YouTube Channel: https://www.youtube.com/@GJarrosson