Building in the Era of AI Workarounds with Jake Jones

We dive into the machine room of AI-native legal tech with Jake Jones, co-founder of Flank (formerly Legal OS) – a designer-turned-entrepreneur who's building digital colleagues to serve as the front line between corporate legal teams and the businesses they support.

What makes this episode essential listening is Jake's ability to demystify complex concepts that many of us encounter but few truly understand – from RAG (Retrieval Augmented Generation) to context windows and vector databases.

"We're in the era of workarounds," Jake explains, describing how companies are building complex technical solutions that will likely become obsolete within 12-24 months as AI capabilities advance. His breakdown of how these systems actually function – chunking documents, creating embeddings, and using similarity search – provides a rare glimpse into the machinery behind today's AI applications and why this technical debt is both necessary and temporary.

The conversation takes fascinating turns as Jake drops provocative insights throughout: "I think SaaS is going to die," he declares, predicting that today's point-and-click applications will seem as primitive as telegrams once model-based applications become the norm. "We will look back in 20 years and think, how did the older generations manage to get anything done?"

We venture into unexpectedly philosophical territory when Jake reflects on why interactions with AI can sometimes feel spookily conscious: "What we're seeing is our own consciousness projected into it and being reflected back." These moments of introspection reveal why building in this space requires not just technical expertise but a willingness to confront existential questions about intelligence and humanity itself.

This episode embodies exactly why we started Law://WhatsNext – to capture raw, unfiltered conversations with the people building our future while it's still being shaped. Jake's candid admission that he initially "metamorphosed into fear" about AI's implications before finding a more optimistic path forward mirrors the journey many of us are on.

Whether you're a legal professional trying to navigate the AI revolution or simply curious about the machinery behind the magic, Jake's insights will help you separate signal from noise in a rapidly evolving landscape. And fair warning: his hot takes on everything from hiring practices ("a single marketer who understands how to use AI can do the work of five") to the future of autonomous agents might just fundamentally change how you think about technology's role in legal practice.

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