The Scalability Paradox: What Black Entrepreneurship and Elite Tennis Have in Common

Winslow Sargeant was 12 years old when he figured out arbitrage.

He'd ride down to Boston's North End, buy bricks of firecrackers from Italian vendors for $3, then sell individual packs for a quarter. Forty packs per brick. Ten dollars profit per trip. Not bad for a kid who just wanted money in his pocket.

Everyone loves this story. Young Black kid, no resources, pure hustle. Becomes a PhD electrical engineer. Venture capitalist. Eventually gets appointed by President Obama as Chief Counsel for Advocacy at the Small Business Administration.

The American Dream in action.

Here's what nobody asks: Why did a 12-year-old have to figure it out alone?

Why wasn't there a system teaching kids in his neighborhood how business works? And why, 40 years later when Sargeant is running the Small Business Administration, are 96% of Black-owned businesses still operating with no employees?

This article examines a pattern. Black entrepreneurship. Junior tennis development. 180 years of educational reform. Same problem, different contexts.

The problem isn't individual effort.

The problem is we keep measuring the wrong thing.

The Wealth Gap That Shapes Everything

In 2017, I spent an afternoon walking through Frisco, Texas with Sargeant and Clement Aboge, an African entrepreneur who founded Bridgestage Capital. They were discussing the statistics nobody wants to examine too closely.

For every dollar of white household wealth, Black families hold about three cents.

That's not a gap. That's a different economic reality.

When startup guides talk about "friends and family" capital, they assume you have friends and family with $25,000 to invest in your idea. When your entire extended family's combined net worth is $6,000, you're not starting the race behind.

You're running a different race.

Here's the other number: 96% of Black-owned businesses have no employees. National average is around 80%, already high. But 96% means almost nobody is scaling. Two million Black-owned businesses in America. Overwhelming majority are solo operations.

Sargeant and Aboge spent that walk diagnosing the problem. Access to capital? Mindset? Burnout from discrimination? Lack of experienced mentors?

Yes.

And none of those are the actual problem.

The actual problem is we have no systematic infrastructure for transferring business knowledge to people without existing networks. We have outliers who succeed despite the system.

We don't have systems that make success reproducible.

What Integration Took Away

Before desegregation, doctors lived next to janitors in Black neighborhoods. Not by choice. By law.

But that forced proximity created something unexpected. Visible success.

Kids saw what doctors, lawyers, and business owners looked like every day. Money circulated within the community because it had nowhere else to go. When the doctor needed his house painted, he hired someone from the neighborhood. When the painter needed medical care, he went to that same doctor.

The informal mentorship happened naturally. The janitor's kid could see what a professional life looked like because professionals couldn't leave.

When they could finally leave, they did.

Wealth left. Role models left. The transmission system for knowledge about how success works disappeared.

Sargeant's firecracker hustle worked partly because he grew up in an integrated Boston neighborhood where he could see multiple models of success. Many kids growing up after integration in concentrated poverty never got that exposure.

This isn't an argument for segregation. It's an argument for being honest about what happens when you destroy systems without replacing their function.

Aboge said something during that walk that stayed with me. When Black professionals moved out, "your role model may not have been the best role models." He was talking about what happens when the visible successful people in your neighborhood aren't doctors and business owners anymore.

Nobody rebuilt the infrastructure that segregation had accidentally created. We celebrated integration as moral progressâ€"which it was. We pretended it didn't create new problems.

The money left and the visibility left at the same time. The pathway to opportunity got narrower from both ends.

The Market Trap

"We tend to segment ourselves," Sargeant said. "Focusing exclusively on the African American market. Other groups do not do that. They're selling to the entire country."

Walk through the Bronner Brothers trade show. Biggest Black hair care industry event in the world. Look at who's selling supplies to Black business owners running hair salons.

Vendors from large East Asian supply chains dominate the wholesale booths.

Here's the trap. Target roughly 13% of the population, you've capped your growth before you start. Ignore your community, you lose the authentic connection that makes you valuable in the first place.

Those aren't choices. That's a vise.

I'm living this right now. Writing about infrastructure failure for an audience that includes people who lack infrastructure. Building systems that solve communication barriers while testing low-friction access models so price isn't the gate. The people who most need what I'm building are the same people the market tells me can't scale my business.

That's not just my problem. That's the problem.

Economic isolation compounds social isolation. When both your customer base and your knowledge networks are constrained, scaling becomes nearly impossible. Limited visibility creates limited networks. Limited networks create limited markets. Limited markets reinforce limited visibility.

Round and round.

I've seen the exact same pattern in elite junior tennis for 35 years.

The Tennis Architecture

One coach can't maintain meaningful Socratic dialogue with 12 kids simultaneously on a tennis court. That's not a limitation of effort.

It's a limitation of human attention.

So we default to what scales. Standardized drills. Mass instruction. One-size-fits-all programming.

Not because it develops better players. Because it's all we could do with available resources.

About 90% of junior tennis players never develop into college prospects. Not because they lack ability. The method that works requires intensive individual attention. Observing each player's specific patterns. Adapting guidance in real-time.

That kind of individualized knowledge transfer doesn't scale through traditional coaching labor.

Coaches who focus exclusively on their own academy's players protect their immediate business but limit their influence. Coaches who try to help everyone spread themselves too thin to be effective with anyone.

Same structural failure. Both junior tennis and small business ecosystems depend on non-scalable individualized attention that can't be systematically delivered.

Neither strategy scales.

Every domain where strategic capability matters faces this same constraint. What works best requires resources we can't replicate through human labor alone.

The 180-Year-Old Precedent

In 1834, in the same city where Sargeant would hustle firecrackers 140 years later, a schoolteacher named Bronson Alcott proved that Socratic dialogue works better than lecture-based instruction.

Ask questions rather than providing answers. Observe each student rather than standardizing curriculum. Adapt in real-time rather than following rigid lesson plans.

His students showed remarkable results. His principles became foundations of progressive education.

His schools failed.

Not because the method didn't work. Because it required being Alcott. You couldn't train average teachers to replicate his observational capability. You couldn't systematize his ability to ask exactly the right question at exactly the right moment.

You couldn't scale genius.

Nine years later, Horace Mann created the Common School Movement. Age-based cohorts. Standardized curriculum. Lecture-based instruction. Testing for compliance.

Not because it develops capability better than Alcott's method.

Because 100 average teachers could deliver it to 3,000 students without requiring individual genius at every point of contact.

We're still making that choice. Scalable adequacy over effective but unscalable excellence.

Exceptional entrepreneurs succeed through individual networks and hustle. We don't build systematic infrastructure for teaching entrepreneurship.

Exceptional coaches produce champions through intensive individual attention. We don't build systematic infrastructure for scaling that attention.

Same pattern everywhere you look.

Until now.

The constraint that forced Mann's choice in 1843 was industrial-era economics. Maximizing output through standardized processes and interchangeable labor. What worked for factories worked for schools. What worked for schools worked for every system that needed to scale human development.

But we're not optimizing for industrial throughput anymore. The economy that's emerging rewards exactly what Alcott was teaching: adaptive thinking, strategic capability, entrepreneurial decision-making in environments without playbooks.

After two centuries of colliding with human bandwidth, we can now offload pieces of observation, memory, and tailored prompting to communication tech designed for dialogue. Not content dumps.

And the technology finally exists to deliver what he proved works. Individual observation. Socratic dialogue. Real-time adaptation. Without requiring genius at every point of contact.

For 180 years, we couldn't have both effectiveness and scale.

That constraint is finally cracking.

What Made Success Rare

What made Sargeant's success rare wasn't work ethic. Wasn't intelligence.

What made his success rare was the absence of systematic infrastructure for transferring the knowledge he had to learn alone. He succeeded despite the system, not because of it.

That's why his story gets celebratedâ€"because it's exceptional.

What made Alcott's method unscalable was human cognitive bandwidth. One person can't observe, adapt, and respond to 50 people simultaneously with genius-level effectiveness.

The method worked. The delivery mechanism couldn't scale.

What keeps Black businesses small isn't just capital or discrimination. When 96% of businesses have no employees, you don't have an ecosystem. You have isolated operators without the systematic knowledge transfer that turns individual success into reproducible patterns.

For 180 years, in every domain where strategic capability matters, we've faced the same constraint.

What works best requires resources that can't scale through human labor alone.

So we've celebrated outliers while accepting that most people won't get access to what actually develops capability.

From Outliers to Infrastructure

Aboge said something during that walk that crystallized the problem. "The challenge is to make it systemic, so that even the average people within the average spectrum can learn it. So it's not just outliers."

Sargeant selling firecrackers was brilliant problem solving. But the fact that a 12-year-old had to figure out business principles through trial and error instead of learning them systematically?

That's the gap. No transmission system.

My grandfather was Harvard Class of 1925. Valedictorian of his high school. Full scholarship. Still had to live off-campus in a rooming house because dormitories weren't integrated yet.

He succeeded despite the system.

That's three generations of outliers in my family. All succeeding despite infrastructure gaps, not because of systematic support.

How many potential Sargeants never sold firecrackers because they didn't figure it out alone? How many students with my grandfather's capability quit before overcoming obstacles that shouldn't have existed?

We celebrate survivors. We don't count the casualties of broken infrastructure.

We measure outcomes without measuring the potential that never manifested because the transmission systems weren't there.

That's why 96% of Black businesses have no employees. Not because 96% of Black entrepreneurs lack capability.

Because the system for teaching people how to actually grow businesses doesn't exist for people without existing networks.

What We're Actually Measuring

The pattern shows up everywhere once you see it.

Black entrepreneurship: We measure success stories like Sargeant. Miss the infrastructure gap that keeps 96% of businesses from ever hiring their first employee.

Tennis development: We measure champions produced. Miss the infrastructure gap that means 90% of players never develop their potential.

Education: We measure test scores. Miss whether we're actually developing capability.

We measure outcomes. We ignore transmission. We lose potential.

Sargeant at 12 with his firecrackers. My grandfather living off-campus at Harvard. Alcott's students thriving in Temple School.

All proof that the method works.

None scalable through the resources available at the time.

What's Changing

Some architects are exploring whether communication infrastructure itself might be the missing piece. A systematic ability to translate insight into adaptable dialogue. Not content dumps. Dialogue that observes, adapts, responds.

Not in some distant future. In pilot programs running now.

Picture that 12-year-old who won't have to figure it out alone. Who'll have systematic access to the knowledge that Sargeant had to piece together through individual brilliance.

Who'll succeed not despite the system, but because the architecture finally exists to transfer what works.

The Alcott Dilemma is 180 years old. We know what works, but we can't scale it.

Maybe it's time to question whether that's still true.

Duey Evans has spent 35 years coaching elite junior tennis players and observing what separates systematic development from random success. He's currently exploring whether the constraint that forced us to choose between what works and what scales might finally be changing.