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Interesting Showbiz Tales

A Story of Generosity: How a Woman’s Daily Kindness to a Homeless Boy Was Repaid 20 Years Later

That hallway was always cold, even in the dead of summer. I never could figure out why. Maybe it was the way the wind always found a way to whistle through the cracked windows, or just how that tile floor seemed to suck the warmth out of everything.

Whatever the reason, that spot became mine. It was a little corner tucked behind the apartment dumpsters on 53rd Street in Chicago, wedged right between a broken-down fence and a pizza joint that had seen better days. I was only eight years old when my whole world just fell apart. My mom, Claudia, she passed away from a seizure while she was sleeping.

One minute, she was right there, singing in our kitchen, her big gold hoop earrings swinging. The very next thing I remember is staring at paramedics, watching them try to bring her back to us. She never woke up. It wasn’t long after that my father, Marvin, remarried. Her name was Rhonda, a woman from Birmingham.

She walked into our lives all smiles, bringing her two kids, Yvette and Jerome, with her. It didn’t take long at all for that sweet smile to twist into something ugly. I went from being a kid mourning his mom to being their live-in help.

Rhonda made it crystal clear that I wasn’t part of her family. The food in the refrigerator? That wasn’t for me. The clothes in the laundry? I wasn’t allowed to wash mine unless I was already washing everyone else’s load.

I became their maid, their cook, their janitor, and their errand boy, all rolled into one. She’d wake me up at five in the morning to mop the floors before I even left for school, and she’d scream at me if the lines from the mop weren’t perfectly straight. Then at night, she’d just dump a pile of greasy dishes on the counter and tell me to get to scrubbing while her kids sat in the living room playing video games.

And Marvin, my own father, he just sat there in his recliner, watching football like nothing was happening, like he couldn’t see any of it. Four years went by just like that. From the time I was eight until I was 12, I survived on crumbs, slept on a single thin blanket in the laundry room, and I got really, really good at making myself invisible.

The hunger, though… that was the worst part. Days would just stretch on where I had nothing but tap water. If I got lucky, I’d find some stale crackers. There were times I had to sneak leftovers out of the trash can when Rhonda’s kids didn’t finish their plates.

I remember this one Tuesday afternoon. I was standing outside the train station, just… waiting for nothing in particular. I’d skipped school again. My stomach was growling so loud it felt like a lion—just this sharp, hollow, angry noise. My shirt was stained with old sweat and probably something I’d eaten two days before.

Both of my shoes had holes clean through the soles, and my socks were two different colors. My hair hadn’t seen a comb in weeks; it was matted in some spots and just dry and brittle. I looked like a ghost of a kid, the kind of person you walk right past and don’t even see.

And that’s when I saw her. She was a Black woman, looked to be in her mid-50s, with skin the color of deep mahogany. She had braids streaked with gray pulled back into a tidy bun, and her forearms looked strong, like she’d spent years lifting crates and handling produce. Her hands looked like they had worked hard every single day of her life, but her eyes… her eyes were soft.

Her name was Miss Gloria. She ran a small fruit stand just a couple of blocks down the street. It was really just a folding table set up on the corner. There was no fancy canopy, no bells or whistles, nothing like that.

She sold apples, oranges, pineapples, and cucumbers. It wasn’t anything extravagant, just good, fresh stuff. She’d arrange it all in neat little piles, with handwritten price tags taped to the edge of the table. She used old cardboard boxes for storage and had the table propped up on a couple of old milk crates.

On some days, she’d have gospel music playing quietly from a little Bluetooth speaker. And on that particular day, she noticed me.

She saw the way I was staring at those apples, like they were gold bars locked behind a glass case. She watched me just hanging around, shifting my weight from one foot to the other, trying to pretend like I wasn’t looking too hard. Then her voice cut right through the street noise. It was calm, low, and had this rich southern drawl.

“Boy,” she said, “when’s the last time you ate?”

I just shrugged, and my eyes dropped right down to the sidewalk. I felt this wave of shame just cling to me, thick as sweat. Without saying another word, she reached deep into the pocket of her apron and pulled out a neatly folded $20 bill.

It was soft and worn from use, but it was still good. She handed it right to me, just like it wasn’t even a question. “Here,” she said. “Go get yourself a real meal, and you come see me tomorrow.”

“I’m here every day.” I just blinked, feeling like I’d just seen someone perform a magic trick. My voice cracked when I finally managed to ask, “Why?”

Miss Gloria just smiled, a small, knowing kind of smile. “Because I was hungry once too,” she said. “Now go on, before I change my mind.” And just like that, that was the beginning of everything.

Every single day after that, I went back to Miss Gloria’s stand. And every single day, she’d hand me a $20 bill, like it was just our routine. Some days, she’d add an apple, sometimes it was a banana. I even remember one time she had a peanut butter sandwich all wrapped up in foil for me.

On really hot days, she’d slip me a cold bottle of water. I remember once she saw my toes peeking through my shoes, and she gave me a new pair of clean socks. She never asked me a bunch of questions, never demanded I explain myself, and she never told me to clean myself up or insist I call her ‘ma’am.’ She just… gave. It was consistent, unconditional. There were no strings attached and not a trace of pity.

After a while, I started looking forward to more than just the money. Our little chats on the sidewalk became my daily dose of warmth. She’d tell me stories about her younger days growing up in rural Georgia, about how she raised three kids all by herself after her husband left, and how much she hated traffic but loved listening to gospel quartets.

She swore up and down that strawberries were heaven-sent, but she couldn’t stand the fuzzy texture of peaches. I’ll never forget her laugh. It was deep and came from her chest, the kind of laugh that made strangers on the street turn their heads and smile, too. It reminded me of a kind of joy I hadn’t felt in years.

I started calling her Miss G, and she never corrected me. For years, I held onto those memories like they were gold coins in a secret pocket. I kept them even after I turned 13 and finally ran away from that place I was supposed to call home. I held onto them through all the nights on shelter cots and in cold stairwells.

Even when I was hustling for spare change and working odd jobs at gas stations, I carried Miss Gloria’s kindness in my heart like it was a suit of armor. When I was 16, I managed to borrow a busted-up school laptop that barely worked. I took it to the public library and just started watching videos on YouTube. That’s how I learned basic coding: HTML, JavaScript, just understanding how websites were put together.

Then one night, I stumbled across a video about cyber security. It was all about how systems get compromised, how they’re protected, and how firewalls operate. Something just… clicked. I became obsessed with locks. Not just the metal ones on doors, but the digital ones.

I dove into everything: passwords, encryption, backdoors, how people found ways to break in, and, most importantly, how they could be stopped. The whole idea of protecting something, of keeping danger on the outside, it fascinated me. It felt like I was learning how to build a home that no one could ever kick me out of again.

By the time I was 19, I had taught myself how to code. I didn’t learn it in a school; I never had the money for that. It was all built on late nights at the public library, hovering outside cafes to “borrow” their Wi-Fi, and watching endless free tutorials on a cracked old laptop that someone had literally thrown in the trash.

I practiced by taking websites apart and putting them back together, one broken line of code at a time. I started picking up small gigs online, little jobs helping local hotels secure their booking systems. I’d remove unwanted programs from computers at family-owned shops or install cheap digital security systems in sketchy motels that couldn’t afford the real stuff.

Eventually, I even started designing my own lock system. I called it SafeSnap. It was a smart lock system designed to detect any forced entry attempts, send an immediate alert straight to the homeowner’s phone, and contact the authorities, all in under ten seconds. It was simple, it was clean, and it was effective.

I didn’t have a company yet. All I had was a vision and that same old hunger. By the time I was 23, after saving every single dime and living like I was still broke, I finally had enough money to register a business. It was nothing fancy. Just a name, a basic logo I designed myself, and a simple website so people could see how the lock actually worked.

I had no office and no staff. It was just me, working from the corner of a friend’s couch. I started reaching out to investors, emailing every single address I could find, filling out countless online forms, and sliding into LinkedIn inboxes. I cold-called companies that barely even answered the phone. I even went to networking events where I didn’t know a soul, just on the off-chance I could shake the right hand.

Ninety percent of the time, I was completely ignored. Some people hung up on me. Some called me “ambitious,” but they didn’t mean it as a compliment. A few straight-up laughed in my face. They told me I needed a team, that my idea would never scale, that I looked too young, and that I looked too broke.

But two people didn’t laugh. One was a woman named Hannah, an investor based in Seattle. She had grown up poor herself and saw something in me that reminded her of a little brother she had lost. The other was a man named Tunde, a Nigerian-British entrepreneur in London. He had built two tech startups from scratch and respected grit a lot more than a fancy resume.

They both told me the exact same thing: “We believe in you.” And then they backed up those words with real money. It was enough capital to help me finally manufacture units, build up an inventory, and start marketing my idea to real buyers. After that, everything changed.

Hotels started placing orders for SafeSnap in bulk, dozens at a time. Then apartment complexes in Chicago and Miami started placing orders. Word of mouth began to spread, and it spread fast.

Homeowners wanted peace of mind, and that’s exactly what I was giving them. The product was good. The support we offered was even better. SafeSnap just blew up. In less than two years, it went from a side hustle I was running from a couch to a seven-figure business.

I hired five people, and then 10. I moved into a condo downtown, bought myself a used car, and finally got a decent bed to sleep in. And for the first time in my life, I didn’t have to wonder where my next meal was going to come from.

But even with money in the bank and my face starting to show up in magazines, my mind didn’t go to my father. It didn’t go to Rhonda or Marvin or any of the people who had let me down so badly. My mind went straight to Miss Gloria.

I hadn’t seen her in years, but I never, ever forgot her kindness. I never forgot the way she looked at me, like I actually mattered. I never forgot the way she always had that $20 bill ready, like clockwork, just so I wouldn’t starve.

I felt like I owed her everything. I went to go find her fruit stand. It took me three weeks and a whole lot of walking around those old streets.

She had moved about three blocks down, a little closer to the main intersection now, but the stand looked exactly the same. There were the old wooden crates stacked with apples and cucumbers, the pineapples laid out on the folding table, and that hand-painted sign that just said “Fresh Fruits.”

And there she was. Still standing, still selling, and still smiling. She didn’t recognize me at first. “Can I help you, young man?” she asked, adjusting the scarf she was wearing.

I smiled. “You already did… about 20 years ago.”

She tilted her head to the side, squinting at me. Then, her hand flew up to her mouth. “Jamal?” she whispered. I just nodded.

Miss Gloria’s eyes filled up with tears. “Look at you. You got so tall… and you look so clean. Lord have mercy.”

We hugged, right there on the sidewalk. Cars kept passing by. People stared at us. Neither one of us noticed or cared. The next day, I picked her up and took her out to lunch.

And I don’t mean fast food. I took her to a real sit-down restaurant, the kind with white tablecloths. She ordered the catfish and a sweet tea.

I told her everything. I told her about Rhonda. About the hunger. I told her about coding until the sun came up. About finding the investors. About SafeSnap.

She didn’t interrupt me once. She just sat there and listened, her glass of iced tea sweating onto the table. When I finally finished my story, I looked at her and said, “Miss G, I didn’t come back just to say thanks.”

“I came back to change your life.”

“What do you mean, baby?” she asked, her voice low.

I reached into the leather bag I was carrying and pulled out a folder. Inside that folder were real estate papers, a business license, some bank statements, and a set of car keys. “I bought you a store, Miss G,” I told her. “Not a stand. A real grocery store, with walls, and bright lights, and a freezer section.”

“It’s already stocked with food. All the licenses are paid for and in your name. You won’t have to haul those heavy crates anymore. You’ve got staff now.”

She just blinked, fast, not saying a single word. “And there’s more,” I added. “I bought you a house, just five minutes away from the store. There’s no rent. There are no bills to worry about.”

“And this,” I said, holding up the keys. “This is for your car. It’s parked right outside.”

Miss Gloria’s fork clattered onto her plate. “Boy, don’t you play with me,” she whispered.

“I’m not,” I said, gently taking her hand. “You gave me $20 every single day back when I had absolutely nothing. You fed me when the rest of the world forgot I even existed. You never asked for a single thing in return. But Miss G… I kept count.”

“That’s over $7,000 you gave me. And now, I’m giving it back to you, ten times over.”

That’s when Miss Gloria started to cry. It wasn’t loud. It was just soft, steady sobs. She covered her face with her hands, whispering, “Thank you, Lord. Thank you.”

Word spread like wildfire in that neighborhood. The store had its grand opening four weeks later. We even had a ribbon-cutting ceremony. The sign above the entrance said “Miss G’s Fresh Market” in big, bold white letters. Inside, it had everything: fruit, vegetables, frozen meals, snacks, and even a little smoothie bar in the corner.

Every employee got a free lunch every day. I made sure of that. Miss Gloria wore new clothes now. I’d see her in long skirts, soft cardigans, and nice gold earrings. She had a glow about her. A peace. It was the kind of peace you earn, not the kind you can just borrow.

People from the neighborhood would come by just to see her smile. Kids would drop in after school just to give her a hug. She became a legend on that block. People didn’t just shop at her store; they felt like they belonged there.

But the story didn’t stop there. Rhonda found out. So did Marvin. And so did my half-siblings, Yvette and Jerome. They saw me on a talk show, talking about SafeSnap. My photo was on some tech website. I had a fresh haircut and a clean smile. The headline said something like, “From Street to CEO: How One Man Beat the Odds.”

I can only imagine what that must have been like. Rhonda probably choked on her coffee. Marvin likely dropped his beer can. The kids must have gone completely silent.

Sure enough, about a week later, they showed up at my office. Marvin was wearing this really forced smile. Rhonda looked nervous but was clearly trying to act warm.

“We’re proud of you, son,” Marvin said, trying to sound genuine.

I didn’t smile back. “Funny,” I said. I just stood there, arms folded, wearing my suit. My voice was steady. “I don’t remember you ever being proud of me. Not when I was starving. Not when I was cleaning toilets for food scraps. Not when your wife treated me like I was dirt under her shoe.”

Rhonda opened her mouth to say something. But I just held up my hand. “I’m not here to fight. I’ve moved on. I forgive you. But don’t you think for one second that you’re getting a piece of this.”

Their fake smiles vanished.

“I came out of a living hell,” I told them. “The only angel I met along the way was a woman selling pineapples on a street corner. She’s the one who gave me hope. You gave me nothing. So let’s not stand here and pretend.”

They left without saying much after that. Yvette, my half-sister, messaged me once, trying to apologize. I saw the message, and then I just deleted it. I didn’t need revenge. I had peace.

And I just kept building. SafeSnap eventually went global. I started hiring kids coming out of group homes. I ran free coding classes at the local community center every Saturday. But Sundays? Sundays were for Miss Gloria. I’d go over to her new house and just sit with her on the porch, sipping lemonade and talking.

One day, she looked over at me and said, “You know what I’ve learned in all my years, baby?”

“What’s that, Miss G?” I asked.

“That kindness don’t cost much. But oh, it pays big.”

I smiled. “It saved my life,” I told her.

And it’s true. In a world that so often forgets about the hungry, the poor, and the small voices, one Black woman with a folding table and a few bags of fruit changed everything for me. It wasn’t because she had a lot. It was because she was willing to give what she had.

So, for anyone hearing this story, I just want you to ask yourself: What’s your $20 worth? Because to someone out there, it might just be the start of their everything.

What do you think about this story? Let me know in the comments below this video. Thanks for watching, and God bless.

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