Expert Mode from The Agile Brand Guide®

Expert Mode: Lessons in Growth to Acquisition from Boots-on-the-Ground Expertise

Jan 20, 2026

The prevailing narrative of the tech founder is a well-worn path. It usually involves a prestigious university, a brilliant idea conceived in a dorm room, a whirlwind of venture capital, and a relentless race to “disrupt” an industry, often from the outside looking in. This story, while compelling, overlooks…

#72: Concept to acquisition with Chris Tilkov, DocuSketch

#72: Concept to acquisition with Chris Tilkov, DocuSketch

Dec 2, 2025

Joining me today is Chris Tilkov, General Manager at DocuSketch, an automated estimation and documentation platform that helps homeowners rebuild after natural disasters. Before joining DocuSketch, Chris founded AskAiME, a platform that was successfully acquired. But his journey didn’t start in tech—he began his career as a carpet cleaner…