AMAs
Legal Tech AMAs
I moderate r/legaltech, where I've grown the community from 15,000 to 19,000+ members. These are the AMAs I've facilitated with legal AI leaders - along with my unfiltered takes on what they said.
Harvey Co-founders: Valuation, Hallucinations, and Why Legal AI Doesn't Need to Be Perfect
The most candid conversation I've seen from any legal AI unicorn. Winston and Gabe didn't dodge the hard questions - they addressed the $8B valuation skepticism, the former-employee engagement allegations, and the hallucination problem head-on. What struck me most: their intellectual honesty about what AI can and can't do right now.
Avaneesh Marwaha: The Six-Minute Dilemma and Why Legal Tech Keeps Failing
Avaneesh returned as Litera CEO after a two-year hiatus, walking back into an industry transformed by AI. His framing of the 'six-minute dilemma' - lawyers will abandon any tool that doesn't prove value in six minutes - explains why most legal tech fails. The AMA was a masterclass in enterprise legal tech strategy from someone who's scaled a company from $16M to $250M ARR.
Max Junestrand: Engineering-First Legal AI and Why He Wants the Taste of Blood
Max is 25, has no legal background, and built a $675M legal AI company in under two years. The AMA showed why: he's relentlessly focused on product, dismissive of traditional planning cycles, and refreshingly competitive. 'We wake up with the taste of blood' isn't typical founder-speak - it's a statement of intent.