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(30) Legal AI Live, May 2026, Part 2

Legal AI Live

This Episode’s Top 5 Takeaways:

  1. Proof of humanity in AI-generated content. Shorter, burstier writing with natural quirks (typos, run-ons, personal style deviations) signals authenticity. Long, perfectly structured posts are increasingly read as AI slop.

  2. Open source vs. enterprise AI is a false dichotomy. Tools like MikeOSS aren’t eating Harvey’s or Legora’s lunch; they’re expanding the market to users who could never afford enterprise licenses. Different tools serve different addressable markets.

  3. Vibe coding is accessible but unpredictable. Mathew built a custom app using Perplexity in ~3 hours for $15, orchestrating AI tools against each other. The cost and time savings are real, but the process is nonlinear and can break.

  4. Human taste and expertise still matter. AI output is “pretty good,” but the value-add is curation and judgment (Nick’s 83-year-old father reviewing an AI-drafted lease addendum). The shift may be toward “service as a service” — humans guiding AI rather than just using software.

  5. AI is transforming education. Nick highlighted that AI has made learning more accessible than ever, particularly for people with learning differences like dyslexia, calling it the best educational experience of his life.

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