By combining technology and a care model with the vision for scale, they applied their vision to a broad ecosystem. They believed they could create a sustainable national organization focused on health care in marginalized populations. Together they did just that. In her interview, Ajayi shares how luck, persistence, and a compelling mission statement were key factors in Cityblock's success.

With the benefit of hindsight, what advice would you now give yourself about successfully navigating the early stages of starting a business, particularly the fundraising process?

The early stages of any endeavor are hard. Certainly, because you're pitching a ton trying to convince people of your idea. You don't always have as many proof points as you want. It feels like it's you against the world very often, but it is also so wonderful and so sweet. In hindsight, I would have told myself to savor the early days. And to try to stay present in every stage. Because every step is really special and will be gone soon, so stop to just enjoy and reflect and savor those moments.

In terms of raising funds, I don't come from the startup world. This is my first venture into venture-backed company building; I don't know all the rules and games that people play. And so we actually got this one right, just because we didn't know any better. My advice is to be realistic about where you are, be transparent about what you know, what you don't know, and where you're going. Give your investors a clear sense of where you're confident and where you are still learning because the last thing you want to do is make promises that you can't fulfill or get too far ahead of yourself. We did this sort of intuitively because we're just not from this world. But I see other folks really struggle with that gap between what you aspire to do and what you are actually confident that you can do - it can sometimes get unwieldy if not well managed.

What's your approach to hiring and finding the right fit for the company?

We've gone through some iterative cycles with this process. Our approach is to start by anchoring in values and not just what the company does. In our instance, it is here to be a voice for folks who don't often have a voice. It's here to be a force for social justice and equity. It's here to create a different narrative about what it looks like to value and center the needs of people who often get left behind. We look for people who buy are into that mission.

We also look for people who buy into our ways of being. Our culture is rooted in kindness, collaboration, a desire to listen and learn, and openness to partner across disciplines. We look for people who have demonstrated a sense of humility and willingness to partner and an ability to take feedback, seek feedback, and be collaborative. That sets the bar; that is the minimum threshold for having any other conversations.

Let's talk about your co-founders; what was it like, founding the company together? And what are your group dynamics?

I feel so grateful to have co-founders, I see solo founders out there, and I don't know how they do it. Being part of a team, especially when you're doing something hard, to me, is so critical.

I think what helps us tremendously is that we have very different skills and experiences, yet we have a shared sense of our values and respect for each other. We also have an honest individual and collective desire for self-improvement. We have this ability to take feedback and to just keep going. We're all very resilient in that way. And it makes for a really productive partnership.

Intuition plays a significant role in leadership and is often undervalued in a way that can be detrimental.

A mission statement is instrumental to building the foundations of a company. How did you and your co-founders come up with yours?

Ours was very organic, truthfully. From the very beginning, it was clear to us not only why we were founding this company but also why we were building it the way we chose to build it. Our mission is to radically transform the health of the most marginalized communities across this country. It is expensive, it is big, it is bold, it is audacious. We deliberately anchored around this language, and there's intentionality for each word.

Radical invokes dramatic overhaul, and it speaks a little bit to our social politics. Transformation for us was about the scale and scope of the ecosystem. We want to not just change the experience for the members whom we are so fortunate to serve, but we want to transform the ecosystem around them as well.

The choice of the word health and not healthcare was also very intentional. Health care is what historically our system has done, provided you units of services that we call health care. Health, however, is wellbeing, and it is inclusive, your social health, your mental health, where you sleep, what you eat, who you talk to, your lived experiences - all of that contributes to your health.

How is success measured at your organization?

At a macro level, we are successful when we can engage, build trusted relationships, earn the right to have understood the needs of, and then deliver care for the members we serve. And our outcomes are measured by, did we do all those things and did it result in people being healthier.

The key measure for us in defining what healthier is is if we give people more healthy time in their homes and community, doing the things they value. So we measure days in the community. We measure how much time people spend out of the hospital, feeling well and going about their daily lives with as minimal discomfort as possible.

What mistakes did you make during your career, and what did you learn from them?

A big mistake I’ve made in the past was not listening to my intuition. I've often regretted not giving voice to things that concerned me or places where I had conviction, but I couldn't substantiate it.

Intuition is such a big and important amalgamation of experiences. It comes from pattern recognition, EQ, and picking up social cues that perhaps are not obvious. Intuition plays a significant role in leadership and is often undervalued in a way that can be detrimental.

What do you attribute to your success?

A lot of it is luck. It’s a lot of right place, right time. I would be lying if I didn't say that. Other things are: Having a really clear idea of where you can add value; Having alignment between where your skills are and the problem that you need to solve; And being able to communicate compellingly about the mission.

It also takes a lot of persistence. You just have to keep at it.

What's a career highlight, either to date or like an unexpected career highlight?

This really speaks to my personality. I don't think about stuff like that at all. I just don't. It's going to sound really cheesy, but every day is a highlight. I get to do work that fuels my soul with inspiring, kind, brilliant people.

Self-care is not just about fueling so that we can do more work. It's also about valuing ourselves as humans who deserve to feel whole and healthy.

Women on your radar?

Ashley Wisdom she's building a company called Health In Her Hue. It's tremendous. It's basically a network and a directory connecting black women to physicians and other healthcare providers who see them and understand them, and want to take their needs seriously.

Simmone Taitt, who is building a company called Poppy Seed Health. She provides digital supports to women during pregnancy and also women who have experienced a miscarriage. She is another black woman building a company tailored towards addressing the needs of this specific community of women who get left behind.

Nwando Olayiwola is a physician and Chief Health Equity Officer at Humana. She just got named one of Essence Magazine's seven women in corporate America to look out for. She is a dear friend and an inspiration to me. She's courageous, but she brings people along with her. She opens doors for folks. And it's modeling for me how you can use your privilege and position to create space and opportunity for others.

Do you have a productivity hack you would like to share?

My only productivity hack is self-care. Self-care is not just about fueling so that we can do more work. It's also about valuing ourselves as humans who deserve to feel whole and healthy. It's impossible to continue to work and build and lead in the way you want when you are depleted.