Validic Co-founder Drew Schiller spent 15 years building a platform that connected hundreds of healthcare devices and apps, and he took three runs at an exit before ChartSpan acquired the company in 2026. In this StartUp Health Fireside Chat, Schiller, now Chief Development Officer at ChartSpan, joins Logan Plaster to explain why getting acquired is its own hard problem. He covers how black swan events derailed two earlier deals, why relationships built years in advance matter more than any banker, what buyers are rewarding in today's digital health market, and why founders should think twice before using AI to rebuild commodity software.

This video is a preview of an hour-long live session. The full conversation, including live Q&A, is exclusive to StartUp Health members.

🧱 Getting acquired is two hard problems: building a company worth buying, and then actually closing the deal. 

🦢 Expect a black swan event. Something almost always threatens a deal, so plan for it. 

🤝 Relationships drive exits. Every eventual acquirer came from a relationship Drew built himself. 

📉 Today's market rewards strong fundamentals or a credible AI-native story. Money-losing "standard" digital health is a tough sell. 

💰 Tighten expenses, get audited financials in order, and show a clear path to EBITDA-positive or cash-flow-neutral operations. 

🪑 A sale process has three legs: storytelling (the CEO), financial diligence, and operational diligence. 

🤖 AI lowers the cost of building, not the cost of maintaining. Focus it on your core value and proprietary data. 

🧠 Founder resilience matters. Keep deal knowledge on a need-to-know basis and keep the team building as if the deal won't happen.