'Undercover Boss' Pays off Employee's Mortgage in Surprise Move

Undercover Boss is quite the popular look into the working world for people today. While the reality series has been around for a decade, and similar timing with some clips of the show, but moments from the show are becoming fodder for the algorithm that many are picking up.

A recent clip from the start of August amassed a million views in little over a month, and it truly shows the heart the series brings to viewers. This clip deals with Diamond Resorts CEO Stephen Cloobeck and his experience with Randy at one of his Las Vegas locales.

The pair are doing repairs around the resort and bonding a bit while nearly catching the roof on fire. But then it is revealed that Randy is working at Diamond Resorts and another job, with his wife pulling double duty too, all to get even after a bad business deal. He was owed $200,000 for the sale of his business and then ended up with a $150,000 mortgage on a new home.

The moment that Cloobeck reveals that the mortgage will be handled and that he is also giving Randy cash to help get back on track sparks a wave of emotion. Randy is in tears, calls his wife with the good news and the episode is brought to a close. It's the perfect bit of positivity and reality editing to make anybody feel a little better about the boss at the top of the company.

Cloobeck appeared twice on Undercover Boss, once in the premiere of Season 3 and again in Season 4, Episode 4. Both aired in 2012. Cloobeck has since stepped down as CEO of Diamond Resorts after it was purchased by Apollo Global Management, LLC in 2016.

He also apparently had a bit of a PR snafu in the wake of his first Undercover Boss appearance. According to The Las Vegas Review-Journal, over 100 individuals who claimed to be members of the Diamond Resorts vacation ownership system wanted refunds and other "financial remedies" for their investment in the company and property. They cited a quote from the Las Vegas Review-Journal where Cloobeck said he'd repay unhappy time-share owners. Rising bills and repair costs levied by the homeowners association led to angry owners looking for an out, sending angry letters, and opening a website to gather information about the company's issues.

"We are empathetic toward the needs and circumstances of every owner and member," Cloobeck said in a statement at the time. "In our role as manager of the resort we are in regular contact with owners and members, and we have worked to ensure the plans put in place have the least possible impact on owners and members both in terms of resort usage and financial responsibility."

Cloobeck has most recently been involved in a nasty legal battle with OnlyFans model Stefanie Gurzanski. The pair were in a relationship until Cloobeck reportedly discovered she was posting nude photos to the page instead of just "modeling." It's a saga that is still playing out as of the end of 2021.