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October 18, 2025 16 mins
In this episode, we unpack how small business ownership represents both hope and hardship in Black Chicago’s economic landscape. Through the voices of Charisse Bennett, Akilah McCord, Marquinn McDonald, Chris Davis, and others, we explore the impossible calculations entrepreneurs face, the ripple effects on nonprofits and service providers, and the unique community spaces—like barbershops—that anchor neighborhoods. From federal pressure and debates on immigration to grassroots block clubs and the struggle against gentrification in Bronzeville, this episode reveals how survival, resistance, and innovation come together in a city at the crossroads of crisis and possibility.

Sources and Methodology: This investigation is based on original interviews conducted in September 2025 with Chicago residents, community organizers, nonprofit executives, and small business owners. Additional reporting drew from Chicago city budget documents, Illinois state employment reports, federal Community Violence Intervention funding allocations, Cook County housing data, and real estate market analysis. Some sources requested anonymity due to employment restrictions or safety concerns.

Primary Interviews: Marquinn McDonald (WatchGuard Chicago), Akilah McCord (The Answer Inc.), Chris Davis (educator/entrepreneur), Charisse Bennett (small business owner), and additional community members.

Malachi Webster is a freelance producer and writer covering community organizing, economic development, and social justice in Chicago.

*This work was made possible in part by funding from the Alliance Matters campaign, an initiative of Chicago Independent Media Alliance (CIMA) and the Field Foundation.

https://www.cnwmedia.com
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Episode Transcript

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Speaker 1 (00:01):
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(00:22):
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your voice, your news.

Speaker 2 (00:31):
Welcome back to Cornered, the series telling the stories in
Black Chicago's fight for survival, equity, and community strength. Today
we explore the delicate balance small business owners face and
economically constrained neighborhoods. This episode dives into the broader challenges
black entrepreneurs face, the ripple effects on nonprofit and community

(00:52):
support services, and the tensions created by external political pressures.
We'll also hear how grassroots solutions like block clubs and
innovative funding models are changing the landscape. Let's begin. This
is Cornered, presented by Chicago News Weekly, and we recognize
we shouldn't have left you without a little something to
step to, but we hope you're ready for today's installment.

(01:16):
The business of survival. Small business ownership represents both opportunity
and vulnerability in black Chicago's economic landscape. Seris Bennett, running
a service based consultancy, faces the impossible calculation that defines
entrepreneurship and economically constrained communities. Do I set my price

(01:37):
to what I know it's worth, or do I set
a lower price because I know the work helps people.
When eggs a four dollars picardan, feeding your family ranks
higher than building your confidence, Bennett's dilemma reflects broader challenges
facing Black entrepreneurs. Since twenty twenty, she's observed greater appreciation

(01:59):
for small businesses and grassroots organizations, but also donor fatigue.
People care, but they're more cautious with their giving and
want to see clear measurable impact. This tension between community
need and market sustainability affects every sector. The Cord's nonprofit

(02:21):
work illustrates the phenomenon at a larger scale. Organizations provide
essential services but remain perpetually unstable due to funding structures
that prioritize short term metrics over long term community building.
The ripple effects extend beyond individual businesses. As McDonald notes,

(02:43):
everything's about profit, profit profit, and you really don't give
a damn about the people people people. When community resources
are evaluated purely through market logic, essential but unprofitable services disappear,
from violence intervention to youth mentorship to Eldercare. Davis bridges

(03:04):
this gap through his barbershop, where community building an economic
activity interseect. I definitely put in work at Bubshop, getting
to know the clients and in feel for who they are,
building relationships and networking with them. The shop functions as
an informal community center, information hub, and economic anchor, roles
that formal institutions often fail to fulfill. While small businesses

(03:29):
and nonprofits wrestle with funding and sustainability, larger forces weigh
heavily on Chicago's communities. Federal pressure has intensified local debates
around immigration, crime, and resources, heightening tensions and complicating long
term solutions. The Trump Administration's renewed focus on Chicago has
added federal pressure to local challenges. Presidents trump deployment of

(03:53):
National Guard troops to address crime statistics that don't support
his claims have prompted Mayor Johnson to sign executive orders
protecting resident rights and limiting federal intervention. Trumbled to come
to Chicago not because of violence, but because he's targeting
cities with black mayors. McDonald argues the writings on the wall,

(04:14):
there's a racial divide in this country that's never gone anywhere.
Chicago doesn't rank among the top ten most violent cities nationally,
yet it remains a political target. McDonald sees this attention
as part of a as part of broader efforts excuse
me to destabilize black political leadership and economic progress. The
federal focus has intensified local debates about immigration and resource allocation.

(04:39):
Since twenty twenty two, Chicago has allocated over three hundred
and ten million dollars to support approximately forty thousand asylum seekers,
sparking tensions and communities already struggling with housing service shortages.
But housing advocates argue that these tensions miss the real issue.

Speaker 3 (04:59):
We have to crises, migrant crisies, and a housing crises,
explains one organizer, Before the first bus arrived from Texas,
Chicago already faced the shortage of one hundred and twenty
thousand affordable housing units.

Speaker 2 (05:15):
Escapegoating obscure systematic problems that predate recent immigration. Poor people
will under stress and pressure when they see somebody getting
resources while they've been denied space. They blame those folks,
notes community leader Curtis Washington. Both black and brown people
in these situations are suffering, but from these challenges arise

(05:40):
powerful community driven innovations. Neighborhood block clubs and nonprofit leaders
are forging new paths and violence reduction, resource sharing, and
sustainable service delivery, even as they guard against systematic co optation.
Despite overwhelming challenges, innovative pro which is are emerging from

(06:01):
community led initiatives. McDonald's Watch Guard Chicago has formed alliances
with neighboring block clubs Evans, Langley, Saint Lawrence, creating networks
that address violence, property crime, and community safety has holistically.
Before we formed a block club, shootings were routine, McDonald explains.
After violence dropped for years, we recover stolen properties, shield

(06:24):
each other when police are laid, and sometimes refused to
press charges, instead offering mentorships and jobs. These restorative justice
approaches challenge traditional law enforcement models. When young men attempted
to resume drug sales in McDonald's area, the block club
intervened directly. We didn't call police first, we talked. Since

(06:48):
that day, nothing the violent theffed risk it disappeared. McCord
identifies similar innovation in nonprofit management, where organizations develop high
funding strategies and shared resource models to navigate unstable budgets.
Leaders and advocates, state legislators who fight for appropriations, community pastors,

(07:13):
nonprofit founders have directly influenced my ability to keep programs
alive and expand services. The challenge lies in scaling these
community driven solutions without losing their grassroots character. McDonald warns
against co optation by large organizations that get resources but

(07:34):
don't do the work. Bronsville's ongoing transformation highlights the stakes
of these grassroots battles. Efforts to preserve affordable housing and
community legacy face daunting structural limits, while political engagement becomes
both a crucial tool and a complex challenge for change.

(07:57):
Looking at the Bronzeville Blueprint, Bronzeville's trains ination offers a
case study in both gentrification pressures and community resistance. The
neighborhoods that once house the Jones Brothers Number operation, the
precursor to state lotteries, now hosts developments with half million
dollar price tags alongside persistent affordable housing needs. McDonald credits

(08:18):
credits Alderman pat Dowell while with maintaining mixed income housing options.
If you find you have a little disengagement when I
stutter or lose your place, feel free to visit cnwmedia
dot com, where you can read Cornered directly and you
could even listen right along, pretend it's an audiobook. But

(08:39):
whatever you do, please give us a shout. I'm going
to go ahead and try to run that back one time.
McDonald credits Alderman pat Dowell with maintaining mixed income housing options,
but notes the delicate balance required. She has done a
great job keeping affordability in Bronzeville to the extent she can.
McDonald says the Wild Court's development exemplifies this approach, offering

(09:02):
apartments from roughly nine hundred and fifty dollars to eleven
hundred dollars while providing space for black owned businesses. Yet
preservation efforts face structural limits. Federal tax programs require only
fifteen years of affordability, after which housing can return to
market rates without permanent affordability mechanisms. Today's mixed income developments

(09:24):
they come tomorrow's gentrification drivers. If the number of wealthy
white people who want to live in Brownsville exceeds the
number of wealthy black people who want to live here,
it will no longer be a black neighborhood. One's Michelle
Kennedy lain and simple. The stakes extend beyond individual displacement.

(09:46):
We can't allow outside forces that do not mean well
for our people, our history, and our culture come into
our communities and remove us without our consideration. McDonald ark yes.
He goes on to say we have to fortify relationships and
put fire under leaders to get resources we need, and
not just beautify, but amplify Bronsville so people who who've

(10:10):
grown up, lived, built, and burst here can continue to stay.
As McDonald considers a potential run for higher office, he
embodies attention between grassroots organizing and electoral politics. His experience
illustrates both the necessity and limitation of traditional political engagement.
We've built relationships with our caps office district commanders, We

(10:34):
report emails and letters, do everything they ask. But when
constituents tell you kids are walking around with guns for
four hours without police response to the system isn't working.
The disconnect between political promises and community needs affects every
level of government. State, DEI programs hire twenty two interns,

(10:56):
while housing crises displace thousands. Federal CV funding reaches one
hundred million, while nightly violence continues. City budgets increase property
taxes while affordable housing shrinks. McCord's question as city leaders
remains unanswered. How do job creation housing policies reach grassroots

(11:18):
organizations and entrepreneurs rather than just large institutions. McDonald's proposed
solution emphasizes community accountability over electoral cycles. Follow the money,
but also follow the work. Some get resources, but it's
block clubs, mentors, and teachers who drive lasting change. As

(11:43):
we wrap this chapter, the persistence of Black Chicagoans shines
through building safety nets, economic opportunities, and pathways forward despite
daunting odds. Up next, we'll explore what it will take
for the city to move beyond survival towards true renewal
Tomorrow's Chicago. The voices in this investigation represent different sectors

(12:07):
of Black Chicago, but their experiences converge on common themes
systematic underfunding, policy implementation gaps, and community driven solutions that
emerge despite not because of institutional support. McDonald continues his
pre dawn patrols, building the safety infrastructure that official budgets

(12:28):
promise but rarely deliver. McCord navigates funding cycles that threaten
program certainty while serving families who need consistent support. Davis
creates mentorship opportunities and spaces where young people feel safe,
using his own resources to fill gaps and social services.
Jerise Bennett collaborates her business model between community need and

(12:50):
economic survival, embodying the impossible choices facing black entrepreneurs. Anonymous
sources across sectors, from municipal employees to nonprofit workers to
while business owners describe similar pressures doing essential work without
adequate resources, maintaining hope despite systematic failures. The solutions emerging

(13:12):
from these conditions challenge conventional policy approaches. Block clubs provide
safety services that police departments simply cannot deliver. Barbershops function
as community centers that formal institutions fail to create. Nonprofit
leaders develop funding strategies that transcend traditional grant cycles. Cornered

(13:33):
captures both crisis and creativity, communities pressed to the breaking
points that generate innovative responses. The question facing black Chicago
isn't whether residents can survive these converging pressures, but whether
the broader city can learn from the community driven solutions
before they're displaced or co opted. McDonald's reflection offers both

(13:54):
warning and possibility. We are in such a dire state
as a peace and as a city, you've got to
seriously over commit to really get things done. We don't
have time to play around. The work continues at four
forty five am. In grand applications and barbershop conversations, in

(14:15):
block club meetings and policy hearings. Black Chicagoans remain cornered
by forces beyond individual control, but not without agency, organization,
or hope. As McCord notes, the path to stability feels
a less certain despite more education and talent, but uncertainty

(14:36):
doesn't prelude action. In classrooms and communities, boardrooms and barbershop,
Black Chicago continues building the infrastructure for survival and perhaps eventually,
for something more than survival. The morning call will come
again tomorrow. McDonald will pull on his boots, Davis will
open his shop, Accord will navigate another funding cycle, and

(14:58):
then it will calculate worth versus a wordability. The city
beats on, heartbroken but never surrendered. At the crossroads of
crisis and possibility. This investigation is based on original interviews
conducted in September twenty twenty five with Chicago residents, community organizers,
nonprofit executives, and small business owners. Additional reporting drew from

(15:22):
Chicago City budget documents, Illinois state employment reports, Federal community
violence intervention funding allocations, Cook County housing data, and real
estate market analysis. Some sources requested anonymity due to employment
restrictions or safety concerns. A big shout to our primary interviewees,
Mark Owainne MacDonald of WatchGuard Chicago, the Quila McCord of

(15:43):
The Answer, Inc. And Chris Davis, educated entrepreneur and my barber.
You can check him out at Vanessa Bilion here Studio
on sixty third. I want to say, don't quote me,
I'm not a Chicago native, and a big shout tisheriz
bit At, a small business owner and all additional community
members who contributed. My name is Malachi Webster. I'm a
freelance producer and a writer covering community organizing, economic development,

(16:07):
and social justice in Chicago. This investigation was produced in
partnership with Chicago News Weekly and Public Narrative CIMA. Thank
you so much for listening and who knows you may
see us sooner than you think.
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