Her Low-Income Patients Were Labeled 'Noncompliant and Defiant.' So She Raised $500 Million to Build a Healthcare Company That Put Them First. Working as a doctor, Toyin Ajayi witnessed how the healthcare system fails traumatized patients in marginalized communities-down to the language it uses to describe them. She started Cityblock Health to change the equation.
By Jessica Thomas Edited by Frances Dodds
This story appears in the October 2021 issue of Entrepreneur. Subscribe »

When Toyin Ajayi, MD, began practicing family medicine in Boston, she cared for a patient for several years. "She had a number of chronic physical health diagnoses and a long history of mental health challenges, and she was often hospitalized because she hadn't taken her medicines," Ajayi says. "One time, when I was following up with her after yet another hospitalization, she told me, "I just want you to know, I am not noncompliant and defiant.' In healthcare we develop language that is not person-centered, and is sometimes even disparaging, and she had heard people label her that way. That was really profound for me, and it helped me formulate ideas about what it looks like to earn the trust of people we serve. It also started me down a path of trying to understand how chronic trauma shows up in people's health needs."
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That path led Ajayi to cofound Cityblock Health in 2017 with Iyah Romm and Bay Gross. By March of this year, the company, which provides healthcare for historically marginalized communities, had raised $500 million, surpassed a $1 billion valuation, and grown to serve more than 75,000 members. Cityblock contracts with insurance companies to take on some of their most costly patients — typically low-income Medicaid and Medicare recipients — for a fixed cost per year. It provides members with comprehensive, often home-based healthcare services, particularly important for those dealing with mental health and addiction issues. Cityblock takes on the risk that those patients' care costs will surpass the annual fixed amount it receives from insurance companies. But if its model works correctly, it gives members a single resource for tackling health issues and helps them avoid costly hospital stays.
Ajayi was born in Boston to Nigerian parents who worked in international development, and their family moved to Nairobi when Ajayi was 2. So Ajayi grew up with an awareness of healthcare disparities on a global scale. "I felt really fortunate as a kid who had access to great schools and lots of resources," she says. "I felt an obligation to think about ways to contribute."
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After college at Stanford, Ajayi worked with HIV patients in San Francisco, went to medical school in England, then worked in Sierra Leone. Finally, she returned to the U.S. for her residency in Boston. "I kept bumping up against the ways our healthcare is broken," she says. "Particularly in ways that impact people who are marginalized, who are low-income, who struggle with disabilities, who have mental health needs, who have experienced lifelong trauma — who have lived in a society with systemic racism and structural bias."
While Ajayi might not have envisioned herself becoming an entrepreneur when she set out to study medicine, she says serving patients and leading a fast-growing startup aren't so different. "Being an entrepreneur requires commitment to a different outcome for a problem you've identified and can articulate in strong, clear, compelling, and numerically substantiated ways. Medicine teaches you a lot of that. It teaches you how to problem-solve."