Initially, Montgomery planned to transfer to The University of Texas at Austin after a semester or two at Angelo State University. When his diehard Aggie roommate took him along for a few road trips to College Station, though, Montgomery started singing a different tune. “Texas A&M had this small-town feel I liked,” he said. “But then on Saturdays in the fall, the whole place just lit up.” It would take another few focused semesters at Angelo State and Blinn College to get his grades up to snuff, but by the spring semester of his sophomore year, Montgomery was an Aggie.

Beyond his amateur landscaping business, Montgomery demonstrated a knack for entrepreneurship throughout his adolescence, selling candy he bought in bulk at Sam’s Club to classmates and even starting a modest baseball card business. Naturally, his salesman instincts and go-getter attitude made him a perfect fit for Mays Business School. Or so he thought. “I found out there was a lot to do outside of attending class,” he said, “so I didn’t get off to the best scholastic start.” Worsening matters, Montgomery signed up for his classes out of order and found himself in upper-level courses that “might as well have been taught in French.”

All in all, he spent more time at the Dixie Chicken than in lecture halls during his first year at Texas A&M University, and it showed. When Mays inevitably suspended Montgomery, he rushed back to San Antonio in a panic to prevent his parents from reading the official notice in the mail. “I told them I was there to meet a girl and take a break from school to assistant-coach my high school baseball team,” he recounted, laughing. Montgomery could not be called a complete liar; he did go on a date and get a coaching job after the fact. Inwardly, though, he recognized it was time to put up or shut up if he was going to make a meaningful life.

The scene was utter pandemonium backstage at MTV Studios. It was the height of the boy band era, and the Backstreet Boys were performing on “Total Request Live.” One lowly production assistant stood between a mob of teenage girls and America’s teen heartthrobs. That assistant was Brent Montgomery, and it was his first day on the job. At first, his assignment was to manage which fans could access the studio based on a guest list. The problem was, 14-year-old girls do not usually have a government ID, and desperate mothers were trying to bribe their way past him.

“Eventually, the crowd got settled in, and I thought, ‘Alright, we did our job,’” Montgomery remembered. “But then someone pointed at me and said, ‘Hey, why don’t you go buy a bunch of water?’ Now, I didn’t have that much money, so I never bought bottled water. They gave me $100, and I bought as much as I could carry, about 60 one-liter bottles. Later, I walked away from the set during a commercial break, and I heard expletives over my walkie-talkie. ‘What idiot bought carbonated water?!’ The girls had gone crazy during the performance, and the set was soaked. I ran around the other side of the building and hoped the person in charge wouldn’t remember me.” Thus marked the beginning of Montgomery’s illustrious production assistant career, during which his lofty dreams of telling stories on screen took a backseat to running errands and living at the bottom of the proverbial totem pole. He knew New York was where he needed to be, but he was itching to make something he could call his own. In 2002, he and his business partner, fellow former student Colby Gaines ’97, established Leftfield Pictures with the initial goal of pitching and producing unscripted television shows.

“We like to say we came out of the gate hot,” Montgomery said. “We didn’t sell a show in our first seven years.” Instead, the duo took the camera gear they had scrounged for and shot weddings, bar mitzvahs and infomercials—whatever work they could do to cover their overhead. “It was just hustle, hustle, hustle.” In 2008, they finally produced their first greenlit series, but it was promptly canceled after less than a year on air.

Ever resilient, the Leftfield Pictures team went to work developing the series that would dig them out of their hole for good. They say what happens in Vegas stays in Vegas, but Montgomery and Gaines found a phenomenon in Sin City that would reach across the world and back.

Rick Harrison did not dream of being a TV star, but he knew that good press meant good business. He and his father, Richard “Old Man” Harrison, founded the World Famous Gold & Silver Pawn Shop two miles north of the Vegas Strip in 1989. Every time the shop found its way onto local and national airwaves, Harrison watched his sales numbers go up without fail. At one point, he even secured a deal with HBO for a show centered on the business, but it fell through when he rejected the network’s proposed creative direction.

Then came Montgomery and Gaines. The pair stumbled upon the shop while hunting for show ideas during a Las Vegas bachelor party trip. When Harrison received the first call from Montgomery, he decided to play his cards closely. “Rick started negotiating with me,” Montgomery said. “He told me another production company was interested, and I had to come out with a crew in two weeks or else he would sign with them. I didn’t think he was telling the truth, but I didn’t have much of a choice.”

“Oh, it was 100% a bluff,” Harrison said. “I realized that no one in Hollywood wants you unless they know someone else wants you, so I dropped a bunch of names I knew from HBO and NBC Universal.” The bluff worked wonders. Montgomery arrived with his camera crew a week later and filmed a sizzle reel, a five-minute video showcasing the shop and its employees interacting as they would on air.

“I’d like to say I knew it would be a hit as soon as we started rolling, but that’s the farthest thing from the truth,” Montgomery said. Despite their usual charisma, the shop’s staff got stage fright on camera. Montgomery and Gaines worried about their return on investment. Luckily, with some editing magic and an enthusiastic sales pitch, the sizzle reel made a splash with the History Channel’s front office. The rest is, well, history.

“Pawn Stars” aired its first episode on July 19, 2009, but its popularity ballooned around Christmas later that year. Harrison remembers returning in January after a two-week holiday vacation to a line of people that stretched around his shop and down the sidewalk. “I had the fire marshal and the police department saying I needed stanchions down the road,” he said. “They were afraid the crowd was going to spill out onto Las Vegas Boulevard.”

In months, “Pawn Stars” became the highest-rated show on its network and the second-highest rated reality show in America. Rick’s down-to-business demeanor, his family’s natural chemistry and the show’s air-tight story structure made the production a smash hit. Seventeen seasons in, the World Famous Gold & Silver Pawn Shop and the “Pawn Stars” franchise are still going strong.

Rather than rest on his laurels, Montgomery took the money he made and used it as capital to produce more shows under the Leftfield Pictures banner, including other History shows such as “American Restoration” and “Counting Cars.” In 2013, he established the parent company Leftfield Entertainment, which eventually acquired other production companies and their shows, one of the most notable being “The Real Housewives of New Jersey.” A year later, he sold the company and its catalog to the British network ITV for $360 million. After years of ceaselessly hustling and keeping his head down, Montgomery looked up one day and saw himself at the top of the mountain.

And then, like a thief in the night, March 2020 came. New productions? Canceled. Bustling in-person events? Not a chance. But despite essentially stopping the venture in its tracks, the ever-optimistic Montgomery credits COVID-19 for giving his team something more valuable than money: time. “We were doing something fresh and new with Wheelhouse, and a lot of people wanted to be part of it,” he said. “It was starting to grow a little too fast. Quarantine gave us a chance to slow down and build a more solid foundation.”

Not like Montgomery ever truly slows down. Over the phone, he admitted to pacing circles around his office, almost instinctively opposed to sitting still. His former colleague, television producer Russ McCarroll, called him “indefatigable.” Despite the onslaught of correspondence he receives daily, Montgomery seldom fails to respond to a text or email within an hour. Even more telling of his character, he strives to build relationships with team members at every tier of production.

“He not only knows the names of everybody who works for him, but he also knows their story,” McCarroll said. “That’s unusual in the business world, but it’s about as rare as the Abominable Snowman in television.” Montgomery’s habit is impressive but unsurprising. After all, it was not too long ago that he was a frazzled assistant with dreams of one day hitting it big. In an industry where the golden rule is “it’s not about what you know, but who you know,” he unconsciously embodies a more profound truth:

At the height of the national lockdown, Montgomery and his wife, Courtney, were walking around their neighborhood when something caught his eye. It was his neighbor, a single mother, mowing her lawn. The sight alone took him back in time. For a moment, he could almost feel the rubber grip of his dad’s old mower. The lessons he learned walking back and forth in the Texas heat never left. To this day, he is still pushing forward.