Walked away from over $1M revenue to go all-in on legal | Evan Wong

Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode! Evan Wong is the co-founder of Checkbox AI - the front door for legal teams, triaging and resolving requests before they ever hit a lawyer's desk. We dive into: Walking away from over $1M ARR Using a written memo to bring your team and investors on the journey What happens to engineering identity when nobody writes code by hand Why the goal isn't faster code reviews Harvey, Legora and the frontier labs - what's actually being adopted in-house? Build vs buy in 2026 How to get in front of senior buyers before you have a product Oh, and there's the company value formerly known as "No Mercy", plus a Swedish whisky that's apparently made with AI. Follow Evan LinkedIn: https://www.linkedin.com/in/theevanwong/ Checkbox: https://www.checkbox.ai Follow Dave Newsletter: https://subscribe.daveberner.me LinkedIn: https://www.linkedin.com/in/daveberner/ YouTube: https://www.youtube.com/@dave.berner Instagram: https://www.instagram.com/daveberner_/ X: https://x.com/daveberner_ Website: https://daveberner.me Parachute Website: https://goparachute.ai