Millionaire Dresses as a Bum and Visits His Company on an Undercover Mission — Story of the Day

A homeless man enters an office seeking warmth but instead finds a life-changing moment that reveals the true character of those around him. Unbeknownst to them, he holds the power to transform their future—if only they show a little kindness.

Richard approached one of his company’s offices, the cold air biting at his skin as he pulled his coat tighter. The past month had been grueling and filled with disappointment.

He had visited every branch of his company, hoping to find someone who still embodied the values he had tried to instill. But each time, he was met with indifference, disdain, or outright rejection.

This branch was his last hope. It was managed by Tom, a young man Richard had mentored since his university days. Richard had poured his knowledge and experience into Tom, guiding him through the business’s ins and outs.

Now, Richard was about to find out whether his efforts had made a difference.

As he walked toward the entrance, his mind wandered to the past. He remembered how, in the past, his visits had been grand affairs. The staff would line up to greet him with champagne and warm smiles, eager to impress the company’s wealthy owner.

Lost in thought, Richard didn’t notice the man walking toward him until it was too late. They collided, and the man shot him a disgusted look.

“Watch where you’re going, you bum!” the man spat before disappearing into the building.

Richard didn’t respond. Over the past month, he had grown used to such insults because now, he was just Richie, a homeless man looking for a bit of warmth and kindness.

Disguised as someone who had fallen on hard times, he had been denied entry to every office he visited. This time, he prayed it would be different.

Steeling himself, Richard entered the office and approached the security guard, hoping this time would be different.

The guard looked Richard up and down with a scowl. “What do you want, bum?” he asked harshly.

Richard, keeping his voice steady, said, “I just need to warm up and maybe get something to eat.”

The guard shook his head. “This isn’t a homeless shelter. You need to get out of here. Now.”

Richard stayed calm. “I’m only asking for some food. Can you call Tom? I think he would help me.”

The guard laughed bitterly. “Tom? He’ll throw you out the second he sees you.”

“Please,” Richard said softly, hoping for a small act of kindness.

The guard sighed heavily, rolling his eyes as if the task was beneath him, and finally called Tom. While waiting, Richard glanced at the comfortable-looking couch nearby and thought about sitting down.

Just as he moved toward it, the guard barked, “Don’t even think about it. Stay where you are.”

Richard nodded, stepping back to his spot. Moments later, a young woman walked into the building. She greeted the guard with a friendly smile and was about to head toward the elevator when her eyes fell on Richard. She paused, taking in his worn appearance, and her expression softened.

The woman paused, concern in her eyes. “Sir, are you alright? Do you need help?”

Richard hesitated. “I just need to warm up, maybe get something to eat, and some water if possible.”

She quickly handed him a bottle of water. “Here, take this. Let me take you to the office. We have food there.”

Richard looked at the bottle. “But it’s your water,” he said.

“It’s no problem,” she reassured him. “Please, come with me.”

As Richard moved, the guard stepped in. “Tom said not to let anyone in without his permission.”

The woman frowned. “But this man just wants to eat. What’s your name, sir?”

“Richie.”

“Richie just wants to eat,” she repeated.

The guard crossed his arms. “Tom’s coming down now. Until then, this bum isn’t going anywhere.”

The woman’s expression hardened. “What disrespect! He’s a person just like you and me. Why should he be treated any differently?”

Before the guard could respond, the elevator doors opened, and Tom stepped out, irritated. “What’s going on here?” he demanded.

Richard spoke calmly, “Good afternoon, sir. I just wanted to warm up and have something to eat.”

Tom’s face twisted with disdain. “Do I look like a volunteer? Get out of here! Now! You’re ruining the company’s reputation. What if a client sees a bum in the office?”

The woman tried to reason. “But Tom, he just wants to eat.”

Tom turned on her sharply. “And what’s it to you, Lindsay? You’re just an assistant! Go back to work!”

Without waiting for a response, Tom barked at the guard. “Get him out. And you,” he pointed at the woman, “follow me.”

As she passed by Richard, she whispered quickly, “Go to the back entrance. I’ll take you to lunch.”

Richard barely had time to nod before the guard grabbed him by the elbow and roughly shoved him toward the door, throwing him out onto the cold street without a second thought.

Richard approached the back entrance, shivering slightly from the cold. After a few minutes, the same woman who had helped him earlier came out, carrying a warm smile.

“Let’s go. There’s a nice little restaurant nearby. It’s nothing fancy, but the food is really good,” she said, nodding toward the street.

Richard followed her, grateful for her kindness. “I don’t even know how to thank you. Lindsay, right?” he asked, trying to remember her name.

She smiled, shaking her head. “My name is actually Nancy. Tom never gets it right. He gives me a new name every day. I guess he thinks it’s easier that way. But really, there’s no need to thank me. It’s the least I can do.”

They walked in silence for a few moments until they reached the small restaurant. The waiters glanced at them with disapproving looks, but Nancy didn’t seem to care. She led Richard to a table and sat down across from him.

“Order whatever you want; it’s my treat,” she said, pushing the menu toward him.

Richard hesitated, then asked, “Thank you. Do they pay you so well that you can buy food for a stranger so easily?”

Nancy sighed, her smile fading slightly. “Not really. When I interviewed for the job, Tom promised me a much higher salary. But later, he decided it was too much for a girl fresh out of university.”

Richard clenched his fists under the table, anger boiling inside him. Tom had turned into someone Richard no longer recognized.

Nancy noticed his expression and quickly added, “But it’s no big deal to treat you. My grandmother always taught me that kindness is its own reward. Even if it’s not, I like helping.”

Nancy blushed a little and stammered, “Oh, that probably sounded insulting. I didn’t mean to…”

Richard reached across the table and gently interrupted her. “It’s alright. I do need help, and your grandmother was a wise woman.”

Nancy smiled warmly as she reached for her wallet, paying for the entire meal without a second thought. She then insisted that Richard take some extra food to go, packing it up neatly and handing it to him with a gentle smile.

Richard hesitated but accepted her kindness, feeling a warmth he hadn’t felt in a long time. As he looked at the young woman, he saw not just kindness but a genuine heart. In that moment, Richard realized that he had finally found what he had been searching for all this time—someone who truly cared.

Nancy walked into the office, her usual resolve in place to face another day of Tom’s insults. But something was different. The usual hum of chatter was replaced with frantic whispers.

People huddled in small groups, their faces tense. Sensing something was wrong, Nancy approached a colleague she trusted.

“What’s going on?” Nancy asked, trying to keep her voice steady.

Her colleague looked at her, eyes wide with shock. “The owner of the company has died. Since he had no children, no one knows who will inherit the company.”

Nancy felt a chill run down her spine. “What does that mean for us?”

“Tom thinks he’s next in line,” her colleague explained. “He was the owner’s protégé, after all. We’re all waiting for the lawyer to arrive and clear things up.”

As if on cue, the elevator doors slid open, and the lawyer stepped out. Tom, looking eager, rushed over to greet him, practically blocking his path.

The lawyer didn’t even acknowledge Tom’s enthusiasm. “I’m not here for idle talk,” he said, his tone brisk. “I need to see Nancy.”

A hush fell over the office as all eyes turned to Nancy. She felt her heart race, not understanding why she was suddenly the center of attention. “Me?” she asked, her voice barely above a whisper.

The lawyer glanced at her. “Are you Nancy?”

“Y-yes,” she stammered, confusion growing.

“Then you’re the one I need to speak with. Can we discuss this privately?”

Stunned, Nancy nodded and led the lawyer into the conference room. As soon as the door closed behind them, she couldn’t hold back her questions. “I don’t understand what’s happening.”

The lawyer’s expression was unreadable. “You’re the new owner of the company. Congratulations.”

“WHAT?!” Nancy’s voice echoed in the small room, louder than she intended.

The lawyer calmly placed a folder on the table. “Here are the documents, already signed by Richard. All you need to do is sign, and the company is yours.”

“But… I don’t understand. Why me?” Nancy felt overwhelmed.

“Richard bequeathed the company to you,” the lawyer said, reaching into his briefcase. “Oh, and there’s a letter too—I almost forgot.” He handed the letter to Nancy, who immediately tore it open, eager for answers.

“Dear Nancy,

Six months ago, I received the news that I was dying. It was a shock, and honestly, I’ve managed to hold on longer than I ever expected. What kept me going, what gave me the strength to continue, was the troubling thought that I had no one to leave my company to.

I had no wife, no children—at least none that I knew of. The future of the company I had built from the ground up was uncertain, and that weighed heavily on me.

About a month ago, I made a decision. I decided to visit each branch of my company, to see if there was someone, anyone, who could carry on what I had started. But I didn’t want to be seen as the owner.

I wanted to see the true character of the people working for me, so I disguised myself as a homeless man. I wanted to understand who they really were, how they treated those who seemed to have nothing.

To be completely honest, I was deeply disappointed. No one would even let me in the door. The kindness and respect I had hoped to find were missing, and I almost lost hope. That was until I met you.

Nancy, you and your kindness restored my faith. Despite your youth and inexperience, I see in you a heart full of compassion and a spirit of integrity. These are the qualities that matter most, more than any skill or knowledge.

Please stay true to who you are. Lead the company with kindness and wisdom, and everything else will fall into place as you go along.

Yours truly, Richard

(Or as you knew me, Richie)

P.S. Your first task as the new owner is to fire Tom and call him Timmy.”

Tell us what you think about this story and share it with your friends. It might inspire them and brighten their day.

If you enjoyed this story, read this one: While serving at a wedding, I suddenly spotted the groom—it was my husband, David. Seeing him with another woman, pretending to be someone else, sent my world crashing down. In that moment, everything I thought I knew about my life was turned upside down. Read the full story here.

This piece is inspired by stories from the everyday lives of our readers and written by a professional writer. Any resemblance to actual names or locations is purely coincidental. All images are for illustration purposes only. Share your story with us; maybe it will change someone’s life. If you would like to share your story, please send it to info@amomama.com.