S14E7: Building the AI Layer for Legal Work with Scott Stevenson, Co-Founder and CEO of Spellbook

In this episode of The Room Podcast, we speak with Scott Stevenson, CEO and Co-Founder of Spellbook. Spellbook is an AI-powered platform helping lawyers draft and review contracts faster using generative AI directly within their existing workflows.

Spellbook enables legal teams to accelerate contract creation and negotiation by embedding AI into workflow tools allowing for real-time drafting, editing, and comparison against market data. The company sits at the intersection of legal tech and AI infrastructure, transforming how contracts are created by shifting from slow, manual workflows to intelligent, data-driven systems. This conversation explores how startups are fundamentally a pursuit of truth, how AI is reshaping legal work, and why building enduring companies requires deep conviction in a problem over many years.

Scott shares the core insight behind Spellbook: lawyers don’t need entirely new tools. Rather, they need dramatically better versions of what they already use, seamlessly integrated into their workflow.

We also discuss:
• Growing up in Newfoundland and developing an outsider’s perspective on innovation
• The philosophical lens of “competitive truth-seeking” in startups and investing
• Why early product iterations failed despite traction and how the team stayed disciplined on product-market fit
• The generative AI breakthrough moment inspired by GitHub Copilot
• Why most vertical AI companies overcomplicate their tech stack and how leveraging foundation models creates leverage

Learn more about Scott on LinkedIn and explore Spellbook at https://www.spellbook.legal/

(03:13) Scott’s background growing up in Newfoundland
(05:13) Did Scott always see himself becoming a founder?
(05:58) Scott’s philosophy background and metaphysical idealism
(12:13) How music and creativity led to Scott’s first company
(14:33) Why Scott chose to build in legal tech
(16:13) How Scott navigated early product-market fit struggles
(18:23) The pivot moment into generative AI
(22:33) Who was Scott’s first investor?
(24:43) What drove the early growth and waitlist explosion
(27:43) How Spellbook thinks about its tech stack and AI strategy
(30:43) What’s next for Spellbook
(34:03) A woman who had a profound impact on Scott’s life and career

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