‘Undercover boss’ pays $150,000 mortgage for struggling employee


undercover boss is becoming a popular look at the world of work for people online today. While it’s been around a decade since some episodes of the show aired, but snippets of moments from the show become fodder for the algorithm that many pick up on.

A recent clip from early August amassed a million views in just over a month, and it really shows the heart the show brings to viewers. This clip is about Diamond Resorts CEO Stephen Cloobeck and his experience with Randy at one of his premises in Las Vegas.

The pair make repairs around the station and bond for a bit while nearly taking the roof on fire. But then it’s revealed that Randy is working at Diamond Resorts and another job, his wife also doing double duty, all to get even after a bad deal. He was owed $200,000 for the sale of his business and then ended up with a $150,000 mortgage on a new house.

The moment Cloobeck reveals that the mortgage will be taken care of and that he is also giving Randy some money to help him get back on track triggers a wave of emotion. Randy is in tears, calls his wife with the good news and the episode ends. It’s the perfect piece of positivity and reality editing to make anyone feel a little better about the boss at the top of the company.

Cloobeck appeared twice on undercover bossonce in the Season 3 premiere and again in Season 4, Episode 4. Both aired in 2012. Cloobeck has since resigned as CEO of Diamond Resorts after it was acquired by Apollo Global Management, LLC in 2016.

He also apparently had a bit of a PR snafu following his first Undercover Boss appearance. According to the Las Vegas Review-Journal, more than 100 people who claimed to be members of the Diamond Resorts vacation ownership system wanted refunds and other “financial remedies” for their investment in the business and the property. They cited a quote from the Las Vegas Review-Journal where Cloobeck said he would reimburse disgruntled timeshare owners. Rising bills and repair costs levied by the homeowners association led angry homeowners to seek a way out, send angry letters and open a website to gather information about the problems with the company.

“We empathize with the needs and circumstances of each owner and member,” Cloobeck said in a statement at the time. “As resort managers, we are in regular contact with owners and members, and we have worked to ensure that the plans put in place have the least possible impact on owners and members, both in terms of use of the station than of financial responsibility.”

Cloobeck recently been embroiled in a nasty legal battle with OnlyFans model Stefanie Gurzanski. The pair were in a relationship until Cloobeck found out she was posting nude photos to the page instead of just “modeling.” It’s a saga that is still playing out at the end of 2021.


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