Build Relationships First: Drew Schiller’s M&A Lessons From 15 Years at Validic

In this episode, Logan Plaster talks with Drew Schiller, Chief Development Officer at ChartSpan and Co-founder of Validic, about what it takes to get a digital health company across the finish line. Schiller recounts the deals that fell apart, including one derailed by COVID while under letter of intent, and the ChartSpan acquisition that nearly died before closing in 2026. He explains why a sale process rests on storytelling, financial diligence, and operational diligence. He also shares how expense discipline and audited financials change the conversation with buyers, and why AI makes the question "what business are we in?" more important than ever.

This episode is an excerpt from a live StartUp Health Fireside Chat. The complete session, including live audience Q&A, is available only to StartUp Health members.

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