300% Year-Over-Year: The AI Content Machine for Law Firms (John Fly)

We Built It Because We Had To - Tech Founder Backstories · May 4, 2026 · 14m

In this episode, I'm joined by John Fly, CTO of FirmPilot — a VC-backed AI platform automating marketing for law firms. John shares how 30 years in tech (starting as a 15-year-old coding for a mortgage software company) led him to team up with founder/CEO Jake on a simple idea: "get the ego out of marketing" and let programmatic AI handle the blogs, social media, Google Business Profile posts, SEO touches, and ad campaign management that law firms today pay agencies $25K–$30K/month for. FirmPilot does it for $7.5K–$10K, and the economics are working — they've raised over $20M through a Series…