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.
Jack Newton: The Billable Hour is the Real Blocker and Why Context is King
Jack Newton brought the receipts. The Clio founder addressed everything from the controversial Scorpion partnership to why billing flexibility is harder than it looks, to his vision of AI replacing the billable hour entirely. After 17 years building Clio and fresh off acquiring vLex and ShareDo, Newton delivered the most complete picture yet of where practice management meets AI-powered legal intelligence.
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.