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 Keeps hit big, adding 20-30 people a week in early scaling days, and how they lost (and then regained) some of the rigor that made the first brand work.

Finally, he dives into being on both sides of M&A - acquiring two companies and then exiting via acquisition to get to scale. M&A can leapfrog years of organic growth, but integration is hard. Demetri shares how the team kept multiple paths open until the very end, including seriously considering another acquisition before deciding that selling was the right move.

About Demetri

Demetri Karagas is a New York City–based entrepreneur. He co-founded and led Thirty Madison, a digital health company that grew into one of the leading specialty care platforms in the United States. Founded in 2017, Thirty Madison served millions of patients through brands including Keeps, Nurx, and Cove before being acquired by Remedy Meds in 2025. Prior to Thirty Madison, Demetri founded Get Maid, an on-demand home services marketplace that was acquired by Homejoy. After Google acquired Homejoy, he spent a brief stint working on Search Ads before returning to startup life. Today, he's experimenting with new ideas across healthcare and consumer technology while trying to keep up with his 10-month-old son.

Presented by Aytza