Startup Wisconsin Podcast

Building Autonomous AI for Legal Contract Review with Shantanu Singh of Obviate.ai


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Shantanu Singh didn't follow a straight path to becoming a founder. Cell biology researcher → prosecutor → AI startup co-founder. But every "dot" he dropped along the way prepared him for this moment. When ChatGPT launched, it felt like discovering fire.

In this episode of the Startup Wisconsin Podcast, Shantanu breaks down what makes Obviate.ai different from typical AI wrappers, why most AI products are automated rather than truly autonomous, and how Milwaukee's small but mighty AI founder community creates disproportionate impact.

Episode Topics
  • The founding story of Obviate.ai
  • How autonomous AI agents differ from traditional Gen AI
  • Patent-pending legal reasoning technology
  • The "Guided Autonomy™" approach to contract management
  • Challenges of building AI for the legal industry
  • Enterprise security and data privacy in legal tech
  • The future of AI in contract negotiation
  • Lessons for founders building specialized AI tools
Segments

00:00 Introduction
01:33 Meet Shantanu Singh & Obviate AI
02:45 From Cell Biology to Law to AI Founder
05:24 "Discovering Fire" - The ChatGPT Moment
08:03 The "Dropping Dots" Philosophy
12:34 How Obviate Works - Beyond AI Wrappers
18:41 Automated vs. Autonomous AI Explained
24:38 Building Trust & Going to Market
29:35 Co-Founder Dynamics & "Move Fast and Break Things"
36:35 Wisconsin's Ecosystem Growing Pains
46:04 Margin of Safety vs. Margin of Error
49:58 Milwaukee's AI Founder Community
55:20 The 3-Day Prototype Challenge
01:03:06 What's Next for Obviate AI

Connect with Shantanu

Shantanu on LinkedIn

About Obviate.ai
  • Obviate.ai Website
  • Contract negotiation platform powered by autonomous AI agents
  • Provides detailed contract review, risk analysis, and precise redlining
Inspiration Mentioned
  • Voyager Paper - Minecraft + Nvidia research on autonomous AI agents

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Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

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Startup Wisconsin PodcastBy Startup Wisconsin, Jacob Miller