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This week, the legal AI story split three ways: who gets to regulate it, who gets to run it, and who gets hurt when it fails. Colorado’s new AI Act is already in court after xAI moved to block it, while Brussels is weighing whether ChatGPT now crosses the line into “very large platform” territory under the Digital Services Act. In Washington, the mood turned more operational: U.S. officials privately warned bank CEOs about Anthropic’s latest security-grade model and the cyber risk of putting vulnerability-finding AI inside sensitive systems. And the enforcement drumbeat kept moving as the DOJ touted its first conviction under the Take It Down Act, while a D.C. appeals court refused (for now) to pause the Pentagon’s Anthropic blacklist.

Our feature this week flips the lens from tools inside firms to firms built around tools: Conrad Everhard on Flatiron Law Group, and what changes when legal tech isn’t adopted: it’s the operating model.

On the customer story side: Nilay Choksi, General Counsel at Worksport, says Ruli AI is saving him 25–30 hours a month on contract review and its Monitor tool has even helped him spot when internal policies need updating.

Nilay Choksi, General Counsel at Worksport, evaluated over a dozen legal AI tools before choosing Ruli. The interface, the AI agent, the Word extension — all checked boxes. But it was the pre-sales customer service that closed the deal. Since signing on, he's saving 25 to 30 hours a month on contract review, and discovered use cases he never anticipated — like using Ruli's Monitor feature to flag when internal company policies need updating. For a solo GC with a growing workload, that's not just a time-saver. That's a career-changer.

Click here to continue reading the full customer story

➡️ xAI Sues to Block Colorado’s AI Act | Musk’s xAI is suing Colorado to stop enforcement of the state’s new AI Act, arguing it violates the First Amendment by forcing companies to make disclosures tied to the law’s anti-discrimination framing. Colorado’s law, effective Feb. 1, requires notice when AI plays a substantial role in “consequential decisions” (like jobs, housing, healthcare, and finance) and creates liability for AI-driven discrimination. State sponsors say it’s basic transparency and accountability, while the governor has previously pushed for tweaks to make the regime less burdensome.
^{Apr 13, 2026, Source: Competition Policy International}

➡️ Banks Warned About Anthropic’s New Cybersecurity-Grade Model | U.S. officials privately cautioned leaders of major banks that Anthropic’s new “Claude Mythos Preview” could heighten cyber risk if deployed inside bank systems, because its vulnerability-finding capabilities might be exploited by bad actors. Treasury Secretary Scott Bessent convened the briefing with Fed Chair Jerome Powell; Anthropic says the model won’t be released publicly and will be limited to a 40-company “Project Glasswing” group that includes JPMorgan.
^{Apr 10, 2026, Source: The New York Times}

➡️ ChatGPT Could Face Tougher EU Rules Under the DSA | Reported by Reuters The European Commission is assessing whether OpenAI’s ChatGPT should be classified as a “very large online platform” under the Digital Services Act after OpenAI published EU user numbers above the 45 million monthly threshold. OpenAI said its reporting shows ChatGPT Search averaged about 120.4 million monthly users in the EU over the six months ending September 2025, which could trigger stricter compliance duties if the designation is confirmed.
^{Apr 10, 2026, Source: Thomson Reuters}

➡️ Ohio Man First to be Convicted Under Take It Down Act, DOJ Says | The Justice Department says an Ohio man is the first person convicted under the federal Take It Down Act, signed in May 2025, which criminalizes posting nonconsensual explicit imagery, including AI deepfakes. Prosecutors said he used AI to create and distribute nonconsensual sexual images involving adults and minors and pleaded guilty to cyberstalking and related charges. The law also requires platforms to remove reported material within 48 hours.
^{Apr 8, 2026, Source: NBC News}

➡️ US Appeals Court Won’t Pause Pentagon’s Anthropic Blacklist Yet | Reported by Reuters A D.C. appeals court declined to pause the Pentagon’s supply-chain risk designation of Anthropic, keeping it blocked from Defense contracts as the case proceeds. Anthropic calls it retaliation over AI safety guardrails; the Justice Department says it’s about contract and operational reliability. The decision isn’t final and contrasts with a separate California ruling that blocked another Pentagon order.
^{Apr 8, 2026, Source: Thomson Reuters}

Most conversations about legal technology start from the same premise: law firms exist, and technology is introduced into them.

The question is usually how well those tools are adopted, how much efficiency they create, and whether they meaningfully change how lawyers work. However, a smaller, but increasingly relevant, question sits just behind it: what happens when a firm is built around the technology from the outset?

That is the perspective Conrad Everhard brings. As a founding partner of Flatiron Law Group LLP, he is not approaching legal tech as a buyer or evaluator of tools, but as someone designing a law firm where technology is part of the operating model itself.

We spoke with Conrad to understand how that thinking translates into practice, and what it suggests about the direction of the legal services market.

Looking at legal tech from the inside out

Flatiron is, on paper, a law firm. It focuses on high-stakes M&A and complex transactional work, led by partners with backgrounds in large firms. But the way Flatiron is described leads you to think less about what it actually does, and more about how it is structured to do it.

Rather than selecting tools to support existing workflows, Flatiron’s systems sit at the centre of how work is executed. Flatiron built an AI infused deal operating system called Deal Driver which manages all of the firm’s transactions from end to end (Deal Driver is used by Flatiron internally but may be separately commercialized in the future). The founders of Flatiron are also founders of a separate company called Deal Mentor, which has a built an AI training platform that simulates live negotiations in complex transactions and can be deployed for any learning purpose. Deal Driver and Deal Mentor provide the foundational architecture for Flatiron’s practice model. They are not layered onto practice but embedded within it.

Click here to continue reading the full interview

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