The Whitchurch town councillor, aged 25, has delighted fans with his one-liners during his stint on the hit BBC One show, but was given his marching orders by Lord Alan Sugar after his team flopped in the task of creating children's cartoons.
Despite the disappointment, Gregory, a former Sir John Talbot's School pupil, said he enjoyed the majority of the experience.
"It has been really fun," he said. "You are not going to enjoy every moment of it. It's challenging when you have to defend yourself in the boardroom.
"The days are long. But you meet people who you would never meet otherwise. I met a bunch of great people."
On his team's cartoon disaster, Gregory said he did not want to contribute negatively in something he had no experience in, but ultimately being too quiet was his downfall.
"It was tough," he said. "I have no experience in this industry. I felt the others had more experience in this.
"I do strongly believe that when you say something, there should be a certain intention and conviction based on facts and experience. I didn't feel I had any of those things.
"It fell down for me because I didn't say as much as I could have."
Gregory said that Lord Sugar was "ten times" as scary as he appears on TV, and it was "emotional" to say farewell to his fellow contestants and take the dreaded taxi ride away.
But how does the terror of the boardroom measure up to the rough and tumble of Whitchurch Town Council meetings?
"It's equally intimidating!" said Gregory, with a smile. "I felt quite fortunate that I had been to council meetings. It's not a million miles off.
"Obviously it's different topics you're discussing, and the big difference is the council meetings are a regular thing, but with Lord Sugar, it's infrequent. You don't know what to expect."
Now Gregory will be returning to his beloved Shropshire, running his Raven Yard Antiques in Whitchurch, as well as his commitments as a councillor. But, the military history buff is hoping his experience on The Apprentice may open the door to make historical documentaries.
"It's definitely something I would like to get involved with," he said.