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

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The wind cut through Richard’s worn coat like icy knives as he trudged toward the office doors. His fingers were numb, his face raw from the cold, but he pushed forward. This was the last branch. His last hope.

For a month, Richard had gone from one office to another—offices he once proudly owned—testing the people who worked there. He had given his life to building this company, pouring his values into it like a father raising children. But at every branch, he had only found arrogance, cruelty, and indifference.

Now, with his last bit of strength, he came here. This office was managed by Tom—a young man Richard had personally mentored back in university. Richard had taught him everything: how to lead, how to treat people, how to run a business with honor. Today, he would learn if Tom had remembered those lessons.

Once, Richard’s visits had been events. The staff would practically throw parties. Champagne, smiles, red carpets. Because Richard wasn’t just “Richard.” He had been the wealthy owner. But now, in rags and dirt, he was just “Richie,” a man everyone believed was homeless.

Lost in thought, he accidentally bumped into someone at the entrance.

“Watch where you’re going, you bum!” the man snapped before storming inside.

Richard said nothing. He had grown used to that word—bum. It hurt less every time, but deep down, he was still hoping someone, anyone, would look past the disguise and show kindness.

Inside the building, Richard approached the security guard.

The guard wrinkled his nose. “What do you want, bum?”

Richard kept his voice calm. “Just need a little warmth. Maybe something to eat.”

“This ain’t no soup kitchen,” the guard growled. “Get out before I throw you out.”

Richard tried again, softer this time. “Could you… maybe call Tom? I think he’d want to see me.”

The guard burst out laughing. “Tom? Please. The second he sees you, he’ll toss you out himself.”

“Please,” Richard whispered.

With an exaggerated sigh, the guard finally called Tom. Richard glanced toward a couch, thinking of resting, but the guard barked, “Don’t even think about it. Stay put.”

Richard nodded, shoulders slumping.

At that moment, a young woman walked in, smiling warmly at the guard—until her eyes fell on Richard. Her smile faded, replaced with concern.

“Sir, are you okay? Do you need help?” she asked gently.

Richard hesitated. “I just… I just need to warm up. Maybe a little food. Some water, if possible.”

Without hesitation, she handed him her own bottle of water. “Here. Drink this. Come with me, I’ll take you to the office kitchen.”

Richard blinked at the bottle. “But… that’s yours.”

“It’s no problem,” she insisted with a kind smile. “Please, come.”

But before they could move, the guard blocked their way. “Tom said no one goes in without his say-so.”

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

“…Richie,” Richard said quietly.

“Richie just wants to eat,” she repeated firmly.

The guard sneered. “Tom’s coming down. Until then, this bum stays here.”

Her eyes flashed with anger. “What disrespect! He’s a human being, just like you and me. Why should he be treated any differently?”

Before the guard could answer, the elevator dinged. Tom stepped out, his face twisted in annoyance.

“What’s all this noise?” Tom barked.

Richard spoke calmly. “Good afternoon, sir. I only wanted a little warmth. Maybe something to eat.”

Tom’s lip curled. “Are you kidding me? Do I look like I run a charity? Get out. You’re embarrassing us. What if a client walks in and sees a bum in the lobby?”

The woman tried to intervene. “But Tom, he’s just hungry—”

Tom cut her off, snapping, “And you—what’s it to you, Lindsay? You’re just an assistant. Go do your job.”

Richard noticed the young woman’s jaw tighten.

Tom turned back to the guard. “Throw him out. Now. And you—come with me.”

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

Moments later, the guard shoved Richard outside into the freezing air. His elbow ached from the rough grip, but he didn’t resist. He simply walked to the back entrance and waited.

Minutes later, the woman appeared, her smile a small ray of warmth against the cold. “Let’s go. There’s a little restaurant nearby. It’s not fancy, but the food’s good.”

Richard followed, touched by her kindness. “I… I don’t even know how to thank you. Lindsay, right?”

She laughed softly. “Actually, it’s Nancy. Tom never gets my name right. He gives me a new one every day. I don’t think he even cares enough to remember.”

Richard’s jaw clenched. Tom had become someone he barely recognized.

At the restaurant, the waiters eyed Richard with suspicion, but Nancy ignored them. She slid into a booth and pushed a menu toward him. “Order whatever you want. My treat.”

Richard looked uneasy. “Do they pay you so well you can just buy food for strangers?”

Nancy shook her head. “Not at all. Tom promised me a big salary during the interview. But when I showed up, he said it was too much for ‘a girl fresh out of school.’ I stayed because I needed a job.”

Her smile softened. “But it’s fine. My grandmother used to say, ‘Kindness is its own reward.’ I believe that. So helping you—it’s nothing.”

Richard’s throat tightened. He whispered, “Your grandmother was a wise woman.”

Nancy grinned shyly and ordered food. She even packed leftovers for Richard, insisting he take them. As he held the warm bag, he felt something stir inside him—something he hadn’t felt in months. Hope.

Back at the office, Nancy returned to an unusual scene. People were whispering nervously, gathering in small groups.

“What’s going on?” she asked a colleague.

The woman whispered back, eyes wide, “The owner of the company died. Since he had no family, no one knows who will inherit. Tom thinks it’s him. He’s practically celebrating already.”

Just then, the elevator doors opened and a lawyer stepped out. Tom hurried forward eagerly. “Finally! You’re here to see me, right?”

The lawyer brushed past him coldly. “I’m here for Nancy.”

The office went silent.

“M-me?” Nancy stammered.

“Yes. Nancy, I need a private word,” the lawyer said firmly.

Shaking, Nancy followed him into the conference room. As soon as the door shut, she blurted, “I don’t understand.”

The lawyer placed a folder on the table. “You’re the new owner of the company. Richard left everything to you.”

Nancy’s jaw dropped. “WHAT?!”

He slid her a letter. “This will explain.”

With trembling hands, Nancy unfolded the paper.


Dear Nancy,

Six months ago, I learned I was dying. The hardest part was knowing I had no one to leave my life’s work to. I had no family, no children.

So I traveled to every branch of my company, disguised as a homeless man, hoping to see the true character of the people working for me. I wanted to know who would treat me with kindness when I had nothing to give.

Everywhere I went, I was rejected. No one even let me through the door—until I met you.

Nancy, you gave me hope. You offered me your water, your time, and your heart. You treated me with respect when no one else would. That is what truly matters.

I leave this company to you. Lead it with compassion and wisdom, and you will succeed.

Yours truly,
Richard (or as you knew me, Richie)

P.S. Your first order of business: fire Tom. Or as I like to call him, Timmy.


Nancy lowered the letter, tears filling her eyes. In her heart, she knew Richard had seen something in her she hadn’t even seen in herself.

And in that moment, she vowed to honor his faith in her—with kindness.