Building the AI Insurance Giant From Scratch
- S2E52
- 43:42
- July 8th 2025
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
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