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WATCH: Nate Berkus Shares His Craziest Oprah Stories: 'We Got to the Checkout and Oprah Didn't Have a Purse'

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A certain amount of chaos is to be expected behind the scenes of any TV show, but after 25 years on the air, it’s hard to imagine anyone ran a tighter ship than Oprah. We’d like to think the greatest stress on any given day at Harpo was how to park a hundred free cars in downtown Chicago.

Not so, according to Nate Berkus, who came up under the media magnate as a guest decorator and later, close friend. The interiors talent, now a mogul in his own right with a design firm, Target line and new TV show in the works, shared some of his craziest moments from his Oprah years with PEOPLE.

RELATED: Everything You Need for Your Home from Oprah’s Favorite Things

One family who received a redesign offered Berkus and his crew a soak in a hot tub they had hidden beneath a living room floor panel. “Of course, we were politely like, ‘no but have fun with your new bookshelves,'” he recalls of the unusual invitation.

RELATED: Lauren Conrad on Holiday Plans and Decorating a Home with Husband, William: ‘Everything Can’t Be Pink’

On another unglamorous occasion, the home they were making over was so far from Chicago that rather than return to the city for the night, Berkus and an Oprah producer slept in his car. The designer tells PEOPLE they, “woke up and went back on camera like two hours later.”

But perhaps best of all, is when the then-relatively-rookie decorator went on a shopping trip with Oprah herself, only to find out at the register that, like the president, Oprah doesn’t carry money.

“We got to the checkout and Oprah didn’t have her purse, so I had to pay,” Berkus says. “I was like, ‘Where is your money? Why do I have to pay for your shampoo?'”