James Smith

James Smith had 150 students, five English classes, and a standing Sunday appointment with a pile of marking that never got smaller. So at 25, with barely two paying customers — both friends of friends — he quit his job and bet everything on fixing a problem he knew better than anyone. That was two and a half years ago. Today, Mark My Words is an AI-powered writing assessment platform in schools across Australia and New Zealand, with 200 new schools onboarded in the first five weeks of this year alone — and conversations underway in the US and UK. In this episode, James walks us through the quit-your-job moment, the $80 wake-up call that shaped his entire tech architecture, and the scrappy $9.99 pricing hack that cracked open the school market from the bottom up.