Startup Wisconsin Podcast: Shantanu Singh of Obviate.ai

In this episode of the Startup Wisconsin podcast, host Jacob Miller talks with Shantanu Singh, co-founder of Obviate.ai, a legal tech tool that "reads, analyzes and suggests risks to mitigate and gives you the edits…all without prompting and no typing."

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Shantanu says he built the product he wishes he’d had as a practicing attorney. It’s designed for small businesses, solo lawyers, and law firms, and aims to turn dense agreements into “clear actionable insights,” compressing work that usually takes hours into minutes.

Singh’s path to becoming a founder wasn’t linear. Before law, he studied cell biology at Washington University in St. Louis and did clinical research on Crohn’s disease and ulcerative colitis. He argues science training helps scaffold repeatable systems for navigating ambiguity, while legal training helps persuade through “the gray” because clients hire lawyers when “yes/no answers depend upon what side you’re on.” He also traces his early exposure to Natural Language Processing (NLP) to a 2014 hackathon project that identified risks in open-source licensing, which pushed him into tokenization and related technical concepts, eventually connecting to later side projects.

A key theme in this episode is his “dropping dots” philosophy: he tells people he mentors to get outside their comfort zone, try many things, and trust that the dots will connect later—building the “connective tissue” needed to do something meaningful.

He also distinguishes “automated” vs “autonomous” AI: most apps, in his view, do multi-step automation but still require users to supply “ingredients” (prompts). “Autonomous” is how much can happen without human intervention—yet knowledge work also requires explainability, which becomes a design constraint.

Trust-building with clients has come through testimonials describing the experience as “magic” and through observed usage patterns: some users ran many contracts through in a short burst, using the tool for sanity checks or deal closing—raising pricing-model questions because value is delivered so quickly. He identifies primary customer verticals as SMB owners, solo lawyers, and in-house lawyers.

Finally, Singh describes Milwaukee’s small, focused AI co-founder community: they meet via Slack and in coffee shops to review prototypes and discuss existential threats. He argues a small network can still create outsized impact, and he wants to grow the company in Milwaukee because impact can be “very visible right away.”

Watch the episode to find out more and keep your eye out for more videos from Startup Wisconsin on our pages

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Jacob Miller, "The Startup Wisconsin Guy" is Marketing & Brand Manager for marketing agency Headway in Green Bay, and State Wide Organizer for Startup Wisconsin a website and event series that digs up the best tech and startup events, accelerators, pitches, and resources in that state.