Welcome to Founder Frames.
Decoding the playbooks of entrepreneurs building category-defining companies.
Most people try to solve problems from a distance.
Dr. Toyin Ajayi took the opposite approach.
She built a company for the customers everyone else ignored, and even after becoming an executive, she never stopped showing up for them.
The Long Way Around
At 25, she launched a non-profit in Sierra Leone.
A country with 50 doctors for 7 million people.
She studied at Stanford. Earned an advanced degree at Cambridge. Graduated with Distinction from King's College London.
And then she went to where the problem actually lived.
As a practicing physician in Boston, her customers were the people the system forgot.
Living in poverty. Managing difficult situations. Navigating crises with zero consistent support.
She noticed something most people miss.
People weren't falling through the cracks because they were careless. They were falling through because no one had ever asked what was really going on in their lives.
She eventually rose to Chief Medical Officer overseeing 20,000+ customers.
But here's the part I find interesting.
Even as an executive, she kept seeing customers directly.
She didn't manage from a boardroom. She stayed in living rooms.
That proximity showed her something most executives never get to see.
The system wasn't broken by accident. It was designed to prioritize the wrong things.
What She Built
In 2017, Ajayi co-founded Cityblock Health.
The idea was simple but unconventional.
Build a company designed from the ground up for people in poverty. Not as charity. As a business.
Cityblock sends teams into communities and homes.
They don't just address surface-level issues. They ask where you sleep. Whether you're lonely. What your biggest daily challenge really is.
Then they build action plans in the customer's own words.
Not corporate targets on a spreadsheet. Real goals that real people actually care about.
The results tell the story.
The company took off faster than anyone expected.
Today they serve over 70,000 customers across six states. Revenue has tripled year over year
Ajayi became CEO in March 2022 with a goal to reach 10 million people in 10 years. Building Cityblock
In 2017, Ajayi co-founded Cityblock Health with Iyah Romm and Bay Gross.
The idea was radical in its simplicity. Build a healthcare provider designed from the ground up for people in poverty. Not as charity. As a business.
Then they build Member Action Plans: shared goals between the care team and the patient. Not clinical targets on a chart. Human goals in the patient's own voice.
Cityblock sends care teams into communities and homes. They don't just treat diagnoses. They ask where you sleep. Whether you're lonely. Whether your biggest daily challenge is finding enough food.
Total raised: $891 million. Over 70,000 members across six states. Revenue tripled year-over-year. They aimed to reach 10 million people in 10 years.
The Proximity Advantage
Most entrepreneurs try to solve problems from a comfortable distance.
Ajayi solved hers by refusing to leave the room.
I call this The Proximity Advantage.
Here's how it works.
Stage 1: Feel the Problem Before You Frame It
Ajayi didn't read a report about inequality. She lived near it. She couldn't unsee it.
That proximity created something no pitch deck can manufacture.
A reason to keep going when things get hard.
Think about your own situation for a second.
If your business idea came from a spreadsheet, it might make money.
If it came from something you can't stop thinking about, it might change an industry.
Stage 2: Stay Close as You Climb
This is where most entrepreneurs quietly lose their edge.
They get promoted away from the problem.
Ajayi could have stopped seeing customers when she became an executive. She didn't.
She kept showing up. She kept listening.
When you scale, your instinct is to zoom out.
The Proximity Advantage says zoom in.
The insights that build billion-dollar companies live in the details that executives rarely see.
Stage 3: Build a Model Where Proximity IS the Product
Cityblock's entire business model is proximity.
Teams in communities. Home visits. Plans written in the customer's voice.
By understanding that someone misses an appointment because they can't afford bus fare, Cityblock prevents a much more expensive crisis later.
Better service for complex customers means lower costs for the system.
Cityblock captures that value.
The mission isn't separate from the model.
The mission IS the model.
The Takeaway
Feel the problem first. The best businesses come from something you can't shake. Not markets you analyzed.
Stay close as you scale. Keep listening. Keep showing up. Distance kills insight.
Make proximity your model. Build a business where getting closer to the problem IS how you create value.
Ajayi didn't build a $6 billion company because she spotted a gap in the market.
She built it because she stayed close to a problem everyone else walked past.
Something I’ve Been Thinking About
When was the last time something really bothered you about how things work?
Not a small annoyance. Something deeper.
The kind of thing where you notice it once and then you can't stop noticing it.
That feeling might just be pointing you somewhere important.
Pay attention to it.
Know an entrepreneur who's close to a problem worth solving? Forward this to them.
Keep satisfying your curiosity.
Until next Thursday,
AP