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