What do you do when lawyers tell you the thing you're building probably isn't possible?

Demetri Karagas co-founded Thirty Madison in 2017 with no healthcare background, a consumer business playbook, and a conviction that a one-stop shop for telemedicine and prescriptions was obviously better for patients, even if the lawyers weren't sure it was possible. He and his cofounder had a vision for a platform of multiple deeply specialized brands of which “Project Samson” (the early working name for their flagship brand Keeps) was the first.

In this conversation, Demetri talks about early structural decisions, like which pieces of the value chain to own vs partner, why controlling that first patient touchpoint was worth a slower launch, and how Thirty Madison pioneered asynchronous telemedicine. Demetri opens up about the hubris trap after K ...