But getting on the field was the hard part for the former SuperPrep All-American from Parkway Central High School in St. Louis. Some academic issues nearly forced him to attend junior college. However, where others may have taken the easy route, Sheperd took the road less traveled to Stillwater.
First, he had to make a 3.5 grade point average in his final semester at Parkway Central High. He did so, but that just gave him a chance to earn a scholarship.
"Coach (Todd) Monken told me I had the opportunity to go to NEO (Northeastern Oklahoma A&M junior college) or I could come down here and take some classes, and I would have to make A's in both classes to be eligible," said Sheperd during OSU Media Day on Saturday.
So, during the summer of 2012, while many of the Cowboys' other incoming freshmen were attending summer school classes to get a head start on their college academics, Sheperd was catching the OSU bus. He would ride it to Stillwater High School where he was taking history and math classes to earn his final high school credits.
Since he was not officially a high school graduate, Sheperd was not eligible to receive scholarship money.
"I was like a walk-on essentially. I had to pay me own way," he said.
Sheperd completed all the necessary coursework, and earned the necessary A's, by the start of fall practice a year ago. "By the time I got to the fall I was on scholarship," he said.
He drew inspiration during his efforts to get eligible from his brother, Lamark Brown, who is in training camp with the NFL's Minnesota Vikings after spending a month on the practice squad at the end of the 2012 season.
"I had a lot of support from my older brother because he was doing a lot of big things, so he was a big role model for me. He encouraged me to believe in myself. He told me that if he could do it, I could do it," Sheperd said of Brown, who spent three years at Kansas State before playing his senior season at Division II Minnesota State-Mankato.
Sheperd is looking forward to being more involved in the Cowboys offense this season.
"I just expect to go out and make plays," he said. "I think people are going to be surprised at how many players we have who can make plays. I think everybody knows about Josh (Stewart) and Tracy (Moore), as far as what they've done in the past, but we have a lot of other guys who can make plays, and they have no idea how good they are."
Including one who has already proven he'll go the extra mile to get on the field.