What does it take to sell the company you spent 16 years building, and how does it feel the morning after?

Drew Schiller returns to CEO Pajama Time, this time from the other side of an exit. In June 2026, Validic, the platform he co-founded in 2010 to connect data from wearables and in-home medical devices into the healthcare system, was acquired by ChartSpan. In this conversation, Drew walks through the full arc of the sale, from the work his leadership team did to map the acquirer landscape 18 months prior, to the inbound offer that set things in motion, and the nitty gritty of managing an exit.

Drew talks about both the mechanics and the emotional reality of a strategic sale and shares advice for other founders. He explains why you can never tip your hand that you're a seller without losing all your leverage, why the conversations that went furthest came from prior relationships, and why lining up the right value proposition with the right executive at the right time is the hardest part. Drew talks through surviving an earlier near-exit that didn't close, and the roughly 75/25 split between running the sale and running the company, and how to successfully get through a diligence.

Then there's the morning after the close, when Drew says he felt 5,000 pounds lighter and realized just how much weight founders carry the whole way through.

About Drew

Drew Schiller is the Chief Development Officer & Board Director at ChartSpan. Prior to that he was the CEO and co-founder of Validic (founded in 2010 with his co-founder Ryan), a platform that connects data from wearables, in-home medical devices, and health apps into the healthcare system, which was acquired by ChartSpan in 2026.

Presented by Aytza

Resources

Bought not sold: positioning your company for exit optionality

M&A Is Hard to Get Right