🎙️ This week we sit down with Shawn Curran, CEO of Jylo — for a conversation that starts where a lot of legal teams and law firms are quietly stuck: Now that almost anyone can build software, should they?

Shawn is unusually well placed to answer. He spent the best part of two decades as a technologist inside private practice — McGrigors, Latham & Watkins, Freshfields, then head of legal tech and later director at Travers Smith, before spinning Jylo out of the firm two and a half years ago. 

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He's watched the industry crawl from paper files 📄 to systems of record 🗄️ to systems of productivity ⚙️ and now to what he calls ”systems of intelligence” 🧠. So when he says the barrier to building software is ”literally on the floor” 📉, it lands with some authority. And he's thrilled about it. The open-source wave of lawyer builders democratising access to their products — Will's MikeOSS, Antti Innanen's Lavern — is, to Shawn, a long-overdue correction. Now the person who actually understands the work describes it in plain English and watches it take shape.

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This discussion plays out against a legal technology market that refuses to sit still. One week it's a new open-source release; the next, Kirkland & Ellis commits half a billion dollars to its own platform; the week after, a frontier lab ships a legal plugin. Shawn admits he loses a faintly ridiculous amount of time to ”is this Jylo for free?” emails. 

Which brings us to Shawn’s stand out observation from our conversation – we talk endlessly about ROI; Shawn would rather we talked about ROT (return on token). If a firm spends thirty grand vibe-coding something nobody ever opens, it hardly matters that it would have cost two hundred grand in engineers; it's still money set on fire. 

”Return on token. What's the return on token? 'Rot.' … There's a lot of rot out there.” 

Shawn warns that as token prices climb rather than fall, the honeymoon phase of trying everything is going to give way to harder questions about what's actually worth the spend. 

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Connect withShawn Curran — CEO of Jylo 

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For more conversations at the intersection of law and technology, head to⁠⁠⁠⁠⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠⁠⁠⁠⁠.