Building AI for Legal Tech: From CEO of a Failing Startup to New Founder (+ Offering Fractional CTO Services)

Hey Indie Hackers! 👋

I'm Michael, founder of Autojuris AI—we're building AI-powered contradiction detection for legal document review. Currently awaiting Microsoft's approval to launch our Word add-in to the marketplace.

The Journey:

I spent 20 years in the Marine Corps, then pivoted to software engineering. Worked my way from IC → Manager → Director → CEO at PreAct Technologies (LiDAR solutions company). That company didn't make it—I stepped in as CEO to wind it down gracefully, which taught me more about leadership than any success ever could.

Now I'm applying everything I learned (the wins and the painful lessons) to Autojuris AI, where we're using LLM/RAG pipelines to help lawyers catch inconsistencies, contradictions, and risks in legal documents.

The Product:
Iris: Microsoft Word add-in + cloud backend that analyzes legal documents in real-time. Think: Grammarly for legal contradictions. Currently in Microsoft's approval process for the Office marketplace.

We're bootstrapping, building in public, and learning fast.

Why I'm Posting:

Looking to connect with other legal tech founders or anyone building AI-powered document tools. Happy to share what we've learned about LLM evaluation, RAG pipeline design, and security-first architecture for sensitive documents.

Offering fractional CTO services through my consulting company, Hemlock Labs. If you're an early-stage founder who needs help with:

0→1 product architecture
Building/scaling engineering teams
AI/ML product strategy
Cloud infrastructure (AWS/Azure/Cloudflare)
Someone who's been through the full IC → CEO journey

I'm available for fractional engagements. I've made all the expensive mistakes already, so you don't have to.

Questions I'm Happy to Answer:

Building AI products (LLMs, RAG, evaluation frameworks)
Leading through company failures and wind-downs
Transitioning from IC to manager to executive
Cloud architecture and microservices
Hiring and building technical teams

Also: If you're in legal tech or have insights on selling to law firms, I'd love to connect!

📧 [email protected]
🔗 autojuris.ai | hemlocklabs.ai