Friday, June 13 – Chicago, IL 🇺🇸

The dream isn’t free.
It’s just discounted for those who never stop working.

And Tasha Reed? She hadn’t stopped working in years.

By day, she managed a customer service team at a mid-sized insurance firm downtown.
By night—and every spare second on weekends—she ran her candle business: Southside Glow.

It started as a creative outlet.
Something soothing after her shifts.
Lavender and cedarwood scents, hand-poured into recycled glass jars, sold on Etsy and at farmers’ markets.

Then came the followers.
Then the custom orders.
Then the boutique in Hyde Park that wanted to stock her next collection.

And still, Tasha packed every box by hand in her apartment kitchen at midnight—knowing full well she didn’t have the time, capacity, or capital to grow.

But quitting her job? That felt reckless.
She had rent. Bills. No generational wealth safety net.

Everyone told her,

“Keep your benefits. Be smart. Wait until the business is ‘ready.’”

What no one could tell her was what “ready” actually looked like.

When Growth Becomes a Grind

By the time she hit her third back-ordered month, Tasha knew something had to give. Either she’d scale Southside Glow, or she’d burn out with it.

She didn’t want to bootstrap into exhaustion.
She wanted to build intentionally—but she needed a cushion.

Something to soften the leap from paycheck to profit.
Something more reliable than a tax refund and good vibes.

She Googled small business loans. Denied.
Asked about accelerator programs.

“We love your product, but you’re too early-stage.”

She tried crowdfunding. Got $300. Spent $100 on shipping.

Then, during a pop-up market in Bronzeville, another vendor handed her a sleek black business card with silver ink.

“You trying to scale?” the vendor asked. “You need to meet the guy behind the money.”

The name on the card?
Mr. Grant Money.

The Exit Plan You Don’t Learn in Business School

He met her the next week, right on time, at a coffee shop near the lake.
Charcoal suit. Clean notebook. Not a drop of condescension.

“You’re overleveraged in energy and undercapitalized in equity,” he said after scanning her sales sheet and growth calendar.
“You’re ready. The problem is you’ve been looking at the wrong kind of capital.”

Tasha raised an eyebrow.

“So… what kind should I be looking at?”

He leaned in.

“The kind you don’t have to pay back.”

The Grants No One Tells Side Hustlers About

What followed was an education.

Mr. Grant Money laid out a strategy built for entrepreneurs exactly like her—Black women founders growing real brands outside of tech, without inherited networks or startup equity.

He outlined:

• The Neighborhood Opportunity Fund (City of Chicago): supports small businesses on the South and West sides with grants for expansion, equipment, and buildout.

• The Fearless Fund: a platform providing grants and mentorship for women of color building consumer goods brands.

• A microenterprise grant via the Women’s Business Development Center: up to $10,000 to help part-time entrepreneurs go full-time.

• The ComEd Energy Efficiency Grant: a niche program that could fund workspace retrofits—perfect for eco-conscious retailers and candle production upgrades.

“You’ve already proven your market,” he told her. “Now we turn that proof into power—and we fund your leap instead of gambling it.”

From Clocking In to Scaling Out

Over the next six weeks, they met twice a week—building her grant applications, tightening her budget, forecasting inventory and fulfillment strategy.

Mr. Grant Money redlined every paragraph of her pitch letter until it read like a strategic vision, not a sob story.

• The first grant hit: $15,000.

• Then another: $5,000.

• Then a sustainability fund covered a studio upgrade.

Tasha didn’t quit her job overnight.
She transitioned—part-time first. Full-time within four months.

By autumn, Southside Glow had:

• Doubled its monthly revenue

• Landed two retail contracts

• Hired a part-time assistant

And her first full-time founder paycheck?
Exactly what she used to make in corporate—minus the 6 a.m. train ride.

Mr. Grant Money Doesn’t Just Fund Hustle. He Funds Liberation.

He didn’t throw Tasha a lifeline.
He built her a bridge.

Because side hustlers don’t need more hustle.
They need structure. Strategy.
And someone who knows where the capital lives when the banks say no.

Today, Tasha mentors other first-gen founders looking to take the leap.
She still pours candles—but now she pours confidence too.

Because when she stepped into her full-time role as CEO, she didn’t fall.
She landed.

And the man in the sharp suit?
He didn’t just believe in her dream.
He backed it—with dollars, direction, and a folder full of keys.

✅ Discussion Questions 

1. What are the biggest financial and emotional barriers that keep side hustlers from going full-time?
   How can we better identify “readiness” outside of traditional startup metrics?

2. Why do you think so few people talk about grants as a pathway to entrepreneurship?
   What needs to change in how we define capital?

3. How can local communities and ecosystems better support founders who don’t come from traditional startup backgrounds?
   What programs or partnerships are missing?

4. What role does mentorship play in helping first-generation entrepreneurs navigate funding and growth?
   Should it be part of every grant cycle?

5. If you had a grant to leave your 9-to-5 and build something, what would you create—and who would it serve?
   And what would your “leap” actually look like?

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