September 20, 2017 04:45 PM

Though President Donald Trump announced he wanted to run for the nation’s highest office in June 2015, Big & Rich’s John Rich first heard about Trump’s bid four years earlier when the country star won the Celebrity Apprentice

“So I win Celebrity Apprentice, all of the confetti falls out of the ceiling, I’m standing there next to Mr. Trump,” Rich — who won season 11 of the reality show, raising a record $1.4 million for St. Jude Children’s Research Hospital — tells PEOPLE Now.

Continues Rich: “And he’s got his arm around. We were taking pictures and he leans over to me and he goes, ‘You know I’m thinking about running for president.’ And I’m going, ‘Yeah I heard about that.’ And he’s like, ‘What do you think?’ I went, ‘I think you ought to go for it man. Why not?’ and he goes, ‘Good. Thanks. Congratulations.’”

The singer-songwriter, 43, admits that looking back at that moment he never imagined he would be “hanging out with the future president” while appearing on the television series.   

“Being around him on the show is not dissimilar to what you see now with him — which is you never know what he’s going to say to you,” explained Rich. “It’s how he keeps everybody on the edge of their seat.”

Now, Rich, along with bandmate Big Kenny, are busy with the release of their new album Did It for the Party.

“We were just walking through Times Square a minute ago and I stopped Kenny and I said, ‘Remember when we walked, I think it was about right here and we dropped at like 2 o’ clock in the morning, and did push ups in the middle of Times Square with our Crown and Coke sitting right next to us’ — which I’m pretty sure was not allowed,” Rich said of the duo’s craziest party moment.

He added: “But we’ve always had a great time with our music and with our lives just coming at it with everything we’ve got. All of the great things that ever happened to us — and it’s probably the same for a lot of people — happen when you’re out there just living life to the fullest. Great things happen.”

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