Operationally-intensive businesses can be unforgiving if you don’t design for unit economics from day one. That’s why I was eager to dig into the playbook behind Thirty Madison and its approach to marrying operational excellence with disciplined financial fundamentals.
I sat down with Steve Gutentag, the co-founder and CEO of Thirty Madison, a healthcare company focused on widening access to specialized care for chronic conditions. The company’s product and operations choices offer a compelling case study for product leaders who need to scale real-world services without sacrificing margins or customer experience.
After previously starting two other companies with his co-founder Demetri Karagas, they launched Thirty Madison in 2017 with Keeps, a men’s hair loss solution. The team has since gone on to launch several new brands, including Cove (for migraines), Evens (for GI issues), and Picnic (for allergies). With the acceleration in telemedicine due to COVID-19, the company has tripled both their revenue and their team size in the past year, recently announcing $140M in Series C funding and a more than $1B evaluation.
We got into the realities of building an operationally complex business with a physical or real-world component. I’ve led product and operations through similar constraints, and I appreciated how Steve shares the lessons he learned from building his first two startups, and figuring out what he was uniquely suited to build. The throughline: pair a crisp problem definition with an operating model that earns its margins every day.
He also shares why they wanted to pick a business that worked with unit economics on day one, walking us through their methodical approach to figuring out if the idea for Thirty Madison would. From their conservative assumptions for each line item, to the unlocks that came from more inventive moves, Steve shares tons of pointers here — including why you should think of your own internal operations as a marketplace, and how unit economics won’t magically fix themselves at scale. In my experience, this is the difference between a growth engine and a leaky bucket.
We then moved to team design — the people mechanics that make operational complexity manageable. In the last part of our conversation, we get into building the team that’s pulling all of this complex work off. We talked about when to hire for industry experience versus a fresh perspective, as well as more granular hiring tactics such as the interview questions he asks to learn about a candidate’s journey as a manager. I shared my own approach: probe for judgment under ambiguity, appetite for continuous improvement, and the discipline to instrument every step of the customer journey.
My takeaway for product leaders: treat operations as a first-class product. Pressure-test the model with conservative assumptions, validate every cost driver, and identify the inventive moves that unlock margin at scale. Keep the customer experience and the P&L in the same conversation, and hire operators who think like product managers and product managers who respect operational constraints. That’s how you build an operationally-intensive business without ending up with upside down unit economics.
Inspired by this post on First Round.
Leave a Reply