The CEO of Diamond Resorts was so impressed by the resilience of his employee he wanted to help him.

After hearing his story, Stephen J. Cloobeck, the CEO of Diamond Resorts, was so blown away by his employee Randy’s resilience that he immediately jumped in to help him.

Viewers of Channel 4’s Undercover Boss USA saw the CEO reward Randy, the maintenance guy, for being a hard worker and persevering when things got tough in his life.

How the CEO of Diamond Resorts Helped a Struggling Employee

resort with a pool and palm trees
Photo by GERARDO MR on Unsplash

Undercover Boss shows bosses who go in disguise among their staff to see where their firm is excelling and where it needs improvement.

Randy shared with the undercover boss that he had moved to the area four years prior. He previously owned a successful RV repair business.

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Randy sold the business to fund his retirement, but as soon as it sold, the buyers filed bankruptcy. They owed Randy around $240,000.

“I was planning on that for retirement, so I had to go back to work,” Randy shared. “My wife is working too. She is a teacher but she’s working at Home Depot. She took a second job there and I got another job also working at UPS, unloading trucks in the morning. I work two jobs trying to get things back in order as it kind of threw us through a loop.”

After revealing who he really was, Cloobeck wanted to reward Randy for being such a resilient and positive guy to work with. “Randy I had so much fun with you. You have such great attitude,” Cloobeck said.

Cloobeck then paid off the $150,000 mortgage and gifted Randy and his wife $50,000 in cash. “You’ve taught me so much. I’m going to give you $50,000 in cash,” he said.

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Randy broke down into tears and immediately called his wife to share the good news. “It’s an unbelievable breath of fresh air,” Randy admits tearfully.

Randy and his wife can now breathe an air of relief and take a break after a long period of hardship. It just goes to show that good things come to people who persevere and having bosses like Stephen Cloobeck who really care about their employee’s lives are a blessing.


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