'Undercover Boss' finds out struggling employee is neck-deep in debt — then gives him life-changing gift

The show "Undercover Boss" is known for spotlighting hard-working employees who rarely get recognition. In such an unforgettable episode, a maintenance worker’s quiet strength and relentless work ethic led to a moment that changed his life forever. Randy, a maintenance employee at Diamond Resorts, believed he was training a new hire when cameras followed him through his daily duties. Randy had no idea that the man working beside him was actually Stephen J. Cloobeck, the company’s CEO, as shown in a YouTube video by Dabl. Randy had been walking the executive through a few repair jobs around the property when their small talk took a more personal turn.

Cloobeck asked where he was from, and Randy explained that he had moved to the area four years earlier from Flagstaff, Arizona. He then revealed that he once owned a successful RV repair business. But things didn’t go as planned. He explained, "They just filed for bankruptcy. They owed me about $240,000. I was planning on that for retirement." Instead, Randy found himself taking on two jobs to stay afloat. He continued, "My wife’s a teacher, but she’s working at Home Depot. She took a second job there. I work for UPS, unloading trucks in the mornings. Two jobs. Trying to get things back in order. It kind of threw us for a loop."

Despite the long hours and financial strain, Randy never once complained. He kept a positive attitude throughout the episode, even after nearly starting a fire and accidentally damaging a gas line during a repair. Cloobeck admired his perseverance. At the end of the episode, once Cloobeck revealed his true identity, he told Randy, "You have such a great attitude." When Cloobeck asked if Randy had any mortgage, he said, "About $150,000." Then came the surprise.

Cloobeck said, "You told me about that bad business deal you made, and you’re hurting. So I’m going to pay off the mortgage. Diamond Resorts is going to take care of that." Randy could barely process the words. But Cloobeck wasn’t finished yet. He also said, "You’ve taught me so much. And I’m going to give you $50,000 in cash." Overwhelmed, Randy broke down in tears. He said, "There are no words. It’s an unbelievable breath of fresh air." He immediately called his wife to share the news. "He is paying off our mortgage. You don’t have to work two jobs anymore," he told her.

Cloobeck’s gift came as a life-changing gesture to someone who had kept going despite setbacks. People were touched by Cloobeck's wholesome gesture and took to the comments to praise his generosity. @BRNardy wrote, "'You don't have to work two jobs anymore.' That hits hard." @Jgreen_919 said, "When he’s on the phone with his wife, you can see just raw emotions. Stories like this make me feel good. Some CEOs just do the bare minimum, some go all out. Massive respect for this one." @gigga143 commented, "This was one of the best CEOs I’ve seen come on this show. What he did for this employee was amazing." @SquirrelTheater added, "Now that is a true leader. Someone who actually recognizes a valuable member of his company."