How to Build AI Agents That Fix Themselves When Something Goes Wrong ft. Keith Gillespie

That Real Estate Tech Guy · May 28, 2026 · 41m

This week I'm joined by Keith Gillespie, founder of REI Automated, a Marine Corps veteran who spent eight years on active duty across 13 countries, missing the births of both his kids, and came home with one obsession: building a real estate investing business in 1 to 2 hours a day. That constraint forced him to build SOPs that became systems, systems that became software, and software that 5 years ago became REI Automated, a three-pillar platform combining education, CRM, and coaching for investors under 50 deals done on their own.

What started as a personal solution has grown into a fully…