If content is the raw material of generative AI, it only makes sense that an AI-driven contract automation platform would want to acquire the world's largest database of contracts and clauses. That is exactly what happened recently when SimpleDocs, a company with an AI contract drafting, redlining and review platform, acquired Law Insider, which claims to be home to 5 million contracts and 20 million clauses spanning more than 50 languages.
One aspect of this acquisition that makes it particularly interesting is that both companies were founded by the same person – and that person, Preston Clark, is our guest today. In that sense, you might say this isn't a typical acquisition story, but more the deliberate convergence of two complementary businesses that were built separately over more than a decade, each with its own DNA, but always with an eye toward this eventual combination.
In an AI market increasingly criticized for being "just GPT wrappers," Clark and his team are betting that workflow-specific tools powered by real contract data will deliver the precision and ROI that legal departments and law firms are demanding.
In our conversation, Clark walks us through the strategic thinking behind this acquisition and how this combined entity plans to differentiate itself in an increasingly crowded legal AI market. He also shares his vision for the future – one that extends beyond contract drafting and review into adjacent workflows that could reshape how legal teams interact with contracts altogether.
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Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.
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Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner).
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Eve, taking care of the tasks that slow you down so you can operate at your highest potential
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