He made 0 sales for the first 8 months. Now he does $200M+ ARR. | Ryan Anderson, Founder of Filevine

Episode notes

Ryan was a successful lawyer with a massive problem. He couldn't find a task management tool that worked for his firm, so he built one himself. He thought he'd solved the problem, but for 8 agonizing months, he couldn't sell a single subscription. In this episode, Ryan breaks down the gritty reality of bootstrapping Filevine into a $3B legal tech startup doing over $200M in revenue. He shares how a random Instagram ad campaign ended his sales drought, how he fought off a Tiger Global-backed competitor built on Salesforce, and how he's completely rewriting his company's architecture to win the AI legal tech war against the likes of Harvey and Legora. Why You Should Listen How 8 months of zero sales almost broke him. Why building customizability into your core product is the ultimate defense. How to recruit top engineers when you have zero funding. Why SMBs often have "beer money but champagne tastes." How to pivot from SaaS to AI.