#72: Concept to acquisition with Chris Tilkov, DocuSketch

#72: Concept to acquisition with Chris Tilkov, DocuSketch

December 2, 2025 · 20 min · Season 2 · Episode 72

About this episode

Chris Tilkov discusses his journey from concept to acquisition in the tech industry.

Many entrepreneurs dream of scaling a niche product, achieving market dominance, and ultimately securing a successful exit—but few actually make it happen. How do you take an idea from concept to acquisition, and what key lessons can other business leaders, including marketers, take from that journey? 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 Ask AiME, a platform that was successfully acquired. But his journey didn't start in tech—he began his career as a carpet cleaner before transitioning into the world of technology and entrepreneurship. About Chris Tilkov Chris Tilkov is a director at DocuSketch and is the founder of Ask Aime, an InsurTech that simplifies estimating and quality assurance for the insurance restoration industry to settle claims quickly and accurately. With over 25 years' experience from flood technician to nationally held positions, Chris works with companies to provide the training and education needed to produce fair and consistent estimates through collaborative technology. In 2023…

People in this episode

Host: Greg Kihlström

Guest: Chris Tilkov

Topics covered

Keywords

Mentioned in this episode

Organizations: DocuSketch, Ask AiME

Places: Palm Springs

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