The Rise & Rise of Brent Montgomery

Photography by Kyle Norton • Wardrobe Styling by Jamie Eisenberg • Hair/Beard Style by Christian Lannucci, Doorbell Barbers • Grooming by Lydia Arroyo

Ever since a quirky pawn shop off the Vegas strip changed his life, reality has been pretty good to this guy

In 1998 Brent Montgomery arrived in Brooklyn to seek his fortune in the TV production business. Or, if not his fortune, then basic food and shelter, for New York proved to be a hard, cold place for a Texas kid with no entrée into the Oz-like fortresses of network television.

“I couldn’t get a minimum-wage TV job to save my life,” Montgomery remembers. A light snow is falling upon the marsh grasses outside his Shingle-Style Greenwich home abounding with gables, peaks and turrets; we are sitting at the rear of the house, in a sleek but cozy man-cave with a gleaming bar and a very large TV. This house is the fruit, or a fruit, of having achieved wild success as a television entrepreneur, first with the reality series Pawn Stars, which he cocreated, then as the man in charge of such seismic reality hits as Queer Eye, Fixer Upper and Duck Dynasty, and finally as the founder and CEO of the Stamford-based media octopus Wheelhouse Group. But we are getting ahead of the story. “In the beginning, I’m shooting bat mitzvahs, which we didn’t have growing up in Texas. I’m shooting weddings in languages I don’t understand. Anything and everything to scrape up extra money—the clock was ticking down.”

Montgomery never let hard times get in the way of his dreams. Indeed, if you believe Jimmy Kimmel, the host of Jimmy Kimmel Live! and his business partner at Wheelhouse, Montgomery’s qualities are so extraordinary that nothing could hold him back. “Brent reminds me of a young Leo DiCaprio,” Kimmel tells us by email. “He is talented, driven and, from a physical standpoint, hotter than an eskimo in hell. Who wouldn’t want to be around that every day?” (To be slightly more specific, Montgomery is a solidly built man of forty-five with blue eyes, a close-cropped beard, and reddish-brown hair combed back neatly from his forehead.) On April Fool’s Day 2002, Montgomery and his Texas A&M roommate, Colby Gaines, founded their own production company, Leftfield Pictures, in an unheated basement on 2nd Street between Avenues B and C in Manhattan. This was the beginning of, well, not very much.

“It was like opening a lemonade stand on a road that was closed down for construction,” says Montgomery. “There were four of us when we started; there were two of us by year three.”

Still, as a student of media history, Montgomery knew about other legendarily unpromising beginnings, notably that of his business idol Walt Disney. Disney’s first animation studio, Laugh-O-Gram, went bankrupt in a booming 1923 economy. Though Disney started his eponymous studio the same year, prosperity did not come until 1928, when he and his chief animator, Ub Iwerks, created the short film Steamboat Willie featuring a new character called Mickey Mouse. As for Montgomery and Gaines, “we each had to go back to full-time work.” They were, however, climbing the TV ladder as segment producers for The Bachelor, the ABC reality show in which a bevy of beauties competes for the affections of a single guy. (The series is still going strong, after eighteen years and five spinoffs.)

In 2008 everything began to change. For starters, Montgomery married Courtney Napurano, a petite blonde from Trumbull whom he met three years prior when both were producing at MTV. So inevitable was the attraction that Brent had to ask his boss for a waiver from MTV’s strict no-dating policy: “I couldn’t hold out from asking her on a date.” (Today they have three young children.) Then Montgomery and Gaines sold their first two reality series, The Principal’s Office, to TruTV, and Bridal Bootcamp, to VH1. The former was an amusing look at young miscreants sent to the principal for offenses ranging from cheating to skateboarding in the hallways; the latter (Courtney’s idea) documented brides-to-be desperately shedding pounds in order to fit into their dream dresses on the appointed day. Neither series caught on, but at least Leftfield had entered the game.

Also in 2008, Colby Gaines held his bachelor party in Las Vegas. Since Vegas is a famously oddball town, and since reality TV was heating up, Montgomery and Gaines resolved to scavenge Sin City for ideas. Gaines said they should do a series about the life of a quickie wedding chapel. (Montgomery agreed, and the show materialized as Happily Ever Faster: not a hit.)

Meanwhile, Montgomery noticed pawn shops scattered everywhere beyond the glitter of The Strip, and wondered, with lukewarm enthusiasm, if there was a show in them. “Just an idea,” he says with a light shrug. “And in my business, an idea alone means absolutely nothing. It’s about what you do with it. Do you spend the money it requires out of your own pocket to develop the idea? In this case, we didn’t have much money.”

Back in New York, Montgomery tasked his sister-in-law, Meredith Voges, an associate producer at Leftfield, with finding just the right pawn shop to try out on film, preferably a family-run one. “Families just have more drama and more chemistry—or lack of chemistry,” Montgomery says. Disappointingly, there were only two family-run pawn shops in Las Vegas. “There were a Greek mother and daughter whose English was hard to distinguish over the phone”—here an affectionate grin spreads across Montgomery’s face—“and then there were these fat bastards, the Harrisons.”

Rick Harrison is the canny proprietor of the Gold & Silver Pawn Shop; he co-owned the shop with his father, the dour Richard “Old Man” Harrison, until The Old Man’s death in 2018. Rick’s son Corey and Corey’s pleasantly dopey friend Chumlee round out the main staff. But when Montgomery went back out to film the Harrisons, he saw no future whatsoever in them. “I’m like, ‘I’m never coming back to this pawn shop again,’” he says. “I didn’t want to go back for the smoke alone. There was more smoke in there than a Mad Men episode.” Worse, the Harrisons were nervous. “We probably didn’t do a good enough job of making them feel comfortable; we were in such a rush because we had no money.” The goal was to condense the footage into a five-minute “sizzle reel” to entice a network to buy the series, but even after all the distilling, Montgomery didn’t see much sizzle. A British editor, Luke Spencer, then asked to take a whack at cutting the Harrison footage. “He put some great music into it, some Johnny Cash, and he cut it in a really cool way.”

As it happened, a perfect storm was gathering. In addition to the budding enthusiasm for reality shows, the economy had tanked, and people were looting their attics for objects to sell. The History Channel, meanwhile, was looking for ways to attract a younger audience; indeed, they had just rebranded themselves History (dropping the “channel”) with the tagline “history made every day” in order to cast a wider programming net. Though History considered Pawn Stars “downscale” in concept, they agreed to take a look. “At the time, the biggest star on History was Hitler,” Montgomery notes, adding that the channel’s audience was mainly men over fifty. “Their ratings would spike any time Germany was on.”

History’s executives liked how the objects that crossed the Harrisons’ transom told a story. The show was—is—a little like Antiques Roadshow in this regard. But unlike Antiques Roadshow, where we learn each item’s approximate value, Pawn Stars boasts the drama of commerce—the haggling and the buying, or the refusal to buy. Memorable Pawn Stars items have included, over the years, Greek coins dating to 325 BC, a 2001 New England Patriots Super Bowl ring, duckbill dinosaur eggs, elephant poop in a can (Chumlee grabbed it for $20), a gold bar from a sixteenth century Spanish shipwreck, a Stephen Stills-owned Gibson guitar, the white Bronco of O.J. infamy (Harrison passed on this, as he did on Saddam Hussein’s fingerprints); and John F. Kennedy’s Oval Office humidor, with poignantly unsmoked cigars in it. (This seller sought $95,000, but Rick haggled him down to $60,000—then sold it at auction for $575,000.)

Pawn Stars was not the usual History fare in 2009. “At the time, a lot of viewers were like, ‘What’s this crap?’” Montgomery says with a chuckle; But Rick Harrison proved to be a charismatic presence, combining regular-guy bonhomie with surprising erudition (as a child he suffered from severe epilepsy, and from the refuge of his bed devoured nonfiction books). “It turned out we hit the lottery with Rick Harrison,” Montgomery remarks. As Rick himself jokes, “They’ve come a long way from Hitler to Harrison.” Pawn Stars wears its history lessons lightly. “We stuffed more information into an episode of Pawn Stars than anything else on History,” Montgomery says. “But you walk away not realizing that we’ve put vegetables into what you’re eating.”

On the strength of Pawn Stars, History’s audience ballooned from 2 million to 7.7 million and surpassed Jersey Shore as the most popular reality show on cable TV. Was Montgomery surprised? “Shocked,” he says. “I didn’t feel the show was big enough in scope [to be such a huge hit]. It wasn’t marketed, it didn’t have a big producer, it didn’t have big stars in it. But every week, just from word-of-mouth, it kept on building on itself.” He remembers an executive at History pulling him aside: “Your life is about to change,” she told him. In fact, Pawn Stars would serve as the foundation for everything that came after; it would be something like Montgomery’s own Mickey Mouse.

Where Walt Disney built his empire on fantasy, it might be said that Montgomery built his on reality. To some people, that might sound like a sketchier proposition. Reality TV is a mixed bag, certainly, but it began on a high note with the airing of An American Family in 1973. The twelve-part series on PBS documented the daily life of the Loud family of Santa Barbara, California, as it painfully unraveled. Margaret Mead, the cultural anthropologist, called the series “a new kind of art form” and compared it to the invention of the novel. Curiously, though, not much happened with the genre till 1992, when MTV debuted The Real World. Inspired by An American Family, The Real World put eight young adults in a house and let the cameras roll as relationships frayed and broke. “Ah, to be young, cute and stupid,” wrote TV critic Tom Shales in a negative review. But the show, immensely popular, also depicted serious struggles then unseen by most Americans, like that of Pedro Zamora, an openly gay man living with AIDS.

Then came the deluge. The Dutch import Big Brother and the Swedish import Survivor launched in 2000, and The Amazing Race debuted in 2001, followed by What Not to Wear, The Bachelor, Joe Millionaire, The Osbournes, American Idol, America’s Next Top Model, The Biggest Loser, Extreme Makeover: Home Edition, Deadliest Catch, The Real Housewives of Orange County, Kitchen Nightmares, Ice Road Truckers, Keeping Up with the Kardashians, on and on and on. Some “unscripted” shows, like the talent-search and food shows, were as heavily formatted as any game show of the past; others, like Joe Millionaire and Bridezillas, seemed ridiculously contrived, or “cooked,” as Montgomery would say. But some shows did capture what enticed people to the genre in the first place: a view into the real lives of others, even if “real lives” was something of an illusion. (But not always an illusion: In one episode of Deadliest Catch, to cite one example, a fishing boat captain has a stroke and is airlifted away, all caught on camera. He died a few days later.)

Montgomery, for his part, did not want his shows to appear cooked. There might be a formula to them, but vivid, surprising, unscripted life should still have room to play out within that formula. Among his own shows, his favorite is Alone—a survival series that feels much more authentic than Survivor. Ten survivalists are dropped in a remote wilderness with just a handful of tools, and the one who stays longest wins a grand prize of $500,000. But what makes Alone feel so original? For one thing, the viewer feels the psychic immensity of each person’s aloneness. In designing the show, “We thought, if we pull the crew out and we have these people document themselves, there’s not going to be any sort of ‘This is cooked, this is not real.’ We almost went too far.” The survivalists are given six cameras apiece and taught how to self-document; there’s no crew to rescue those in imminent trouble. In the first season (2015), Josh Chavez, a tough young cop from Ohio, was first to go. He’d been dropped on a beach strewn with fish heads, a sure sign of bear activity. A few steps into a dense, cold, rainy woods, Chavez trains his camera on a mama bear and her cubs staring down at him from the trees. That night, as he tries to sleep, two large black bears come snooping around his tent. That was enough; in the morning he calls for a rescue boat. As the episode goes on, the spooky howls of wolves are heard in the far distance, then closer and closer, until one unlucky survivalist hears them weaving through the brush…

Montgomery grew Leftfield Pictures at breakneck speed. (Gaines left in 2011, mid-ascent, to form his own venture.) “Looking back, this was pretty crazy,” Montgomery admits. “We took all of our chips and put them back in.” Caution be damned, he created the popular Pawn Stars spinoffs American Restoration and Counting Cars, as well as the series Oddities, which chronicled a Manhattan antiques shop. (There were also less successful series, such as Ball Boys, about a sports collectibles business in Baltimore, and the entertaining United Stuff of America, which took curious objects from history and fleshed out the stories behind them.)

But Montgomery’s boldest stroke was to gobble up other production shops. “Most people in my position, they really love making the shows,” he says. “And I love it, too. But then I realized, Wait a minute, this can be more than just a mom-and-pop shop. This can be a real business.” To this end, Montgomery hired mergers and acquisitions specialist Ed Simpson, a veteran of the European scene, where consolidation of production companies had already occurred. In this country, Montgomery notes, “it was still the wild west.” One $40 million bank loan later, Leftfield was the proud owner of Sirens Media (The Real Housewives of New Jersey), Outpost Entertainment (Forged in Fire) and Loud TV (Tiny House Nation, which would debut under Montgomery’s aegis in 2017). Leftfield Entertainment was now the biggest indie production company in America.

In 2013 the TV landscape was changing rapidly. People were jettisoning cable in favor of Netflix (which had just debuted House of Cards) and then other big streaming services, such as Hulu, HBO Now, YouTube TV and Amazon Prime Video; these, in turn, were backed by behemoths like Disney, AT&T and Google. If this was the new ecosystem, how would Leftfield compete in it? Montgomery was pondering this question early in 2014, when he moved his family to Greenwich. The plan had always been to go suburban, but Greenwich caused him some anxiety: The town represented a sort of emerald city of achievement. “A kid starting out in Brooklyn would never expect to live here,” he says. (In actuality, the Montgomerys found Greenwich friendly and accessible.) And he wasn’t rich, as he then supposed most Greenwichites were. Not until May. That’s when he sold 80 percent of Leftfield to British giant ITV for the majestic sum of $360 million. All at once, Montgomery had gone from being a $30,000-aire to a multi, multimillionaire. How did that make him feel?

“Scared shitless,” he says with a laugh.

We can happily report that a decade of gaudy triumph has not changed Brent Montgomery. His friends describe him as big-hearted, intellectually curious and refreshingly down-to-earth. Paul Buccieri, his former boss at ITV, says, “Brent is not one of those people who wears success on his sleeve, yet he’s built some of the biggest franchises in cable television.” When Buccieri joined A&E in 2015, requiring a move East, “[Brent] was one of the first people to reach out to me. He expressed his passion and his enthusiasm for the Greenwich community, and when my family and I visited we were hooked.” Buccieri, now president of A&E Networks Group, has lived here ever since.

Jon Owsley, comanager of the growth fund at Greenwich private equity giant L Catterton, met Montgomery through business (L Catterton is a Wheelhouse investor) but now counts him as a friend.

“Brent is the same great guy no matter what the situation—whether it be in high-powered business meetings with A-list celebrities or just a group of friends grabbing drinks,” Owsley says. “And despite his enormous success, he is equally kind, thoughtful and giving of his time and attention to just about anyone he encounters. He draws people into his world and then, with great generosity, opens that world up to them.”

Brent was raised modestly in San Antonio, Texas, the son of Jim Montgomery, an environmental engineer in the U.S. military and the Department of Defense, and his wife, Marcia, a schoolteacher. Nothing in his boyhood telegraphed monumental success; Brent was a typical sports nut who dreamed of pro athletic stardom. Later, at Texas A&M, his athletic dreams long since departed, he proved an unremarkable student: His business major sank away under the oppressive weight of Accounting 209. Taking a semester off, he interned at a local TV sports department and “fell right in love with it.” Still, a typical studio hand never gets all that far; we can imagine some Brent-like person rising respectably to the greater Dallas market. A quality that set this Brent apart, though, was sheer, unmitigated hustle. In grade school he’d buy wholesale candy at Sam’s Club and resell it at school for a profit “until the teachers caught me.”

Next came baseball cards. “I put an ad in the classifieds to buy collections, and my father and I would go to people’s homes and sit there right in front of them, going through their cards,” he says. “I was selling them first at school and started making enough money to reinvest, reinvest.” (His prize find was a rookie Pete Rose. We mention this to suggest that Montgomery was born with a hot hand, for even though the card market flatlined, a 1963 Pete Rose in mint condition still sells for around $70,000.)

The upselling habit continued with ITV. But instead of leaving with his millions, Montgomery stayed on as CEO of the newly created subsidiary, ITV America. This put him in charge not only of the Leftfield shows, but also of massive hits like Duck Dynasty, Hell’s Kitchen with Gordon Ramsay, and Fixer Upper. And he oversaw the launch of new series, including American Grit, Tiny House Nation and Queer Eye, a Netflix reboot of the old makeover show Queer Eye for the Straight Guy.

Queer Eye remains a singular phenomenon. Critics have noted the series’ addictive blend of consumerism and spirituality—the provocative notion of self-care as the beginning of soul refurbishment. Montgomery allows that great effort went into making the show a success. “With Queer Eye, which I helped launch right before leaving ITV, we threw the kitchen sink at it, almost unlike anything we’d done. We weren’t so focused on making a few shekels off of it, because we thought, Man, if this could be a transformative show for us, into the next wave of media… And thankfully it was that kind of show—it was Netflix’s first unscripted big hit.” (Queer Eye’s Fab Five have parlayed their TV fame into cultural-political weight, as they discuss social problems like child abuse, addiction and living with HIV.)

Back up. Did Montgomery just say he left ITV America?

Even while sitting on top of the world, it turns out, the entrepreneur in him never slept. So what sort of business does a $360 million man build from scratch? Montgomery refers us to a 1957 strategic business plan, laid out on one sheet of paper, by none other than Walt Disney. “Because he’s Walt Disney, he drew it—a single set of connected images that shows how he built his flywheel,” Montgomery says. A flywheel is a heavy disk that, once in motion, also turns its satellite gears (think markets), pushing the whole machine (think company) smoothly and unstoppably forward. At the center of Disney’s drawing is a large box containing the words “Theatrical Films,” and revolving around it are smaller boxes with “Disneyland,” “TV,” “Music,” “Merchandise Licensing,” “Comic Strips” and “Publications (Books and Comic Books)” written in them. Arrow lines connect all the boxes, and they’re adorned with doodles of Mickey Mouse, Donald Duck and Goofy, scurrying back and forth. Hand-lettered notations explain each line, such as the one connecting the “Theatrical Films” box to the “TV” box: “Provides interchange of stars.” This hyper-symbiosis was revolutionary in the fifties. Up to then, for example, film studios had no interest in television despite the obvious parallels. “They thought it was a passing fad.”

Montgomery thinks of Wheelhouse Group as a sort of baby Disney for the twenty-first century. It doesn’t sound like a baby anything, though. Jimmy Kimmel explains, with admirable compression, almost everything that Wheelhouse is up to: “We’re working on shows, films, apps, new marketing concepts, specials, live television events, toys, games, game shows, short-form video, and pop-up experiences. We may even start a religion, if we can figure out which one of us gets to be God.”

Montgomery credits Kimmel, the creator of Wheelhouse’s Kimmelot division, with “pouring jet fuel” on his start-up. Their friendship began with a dinner, then another, over which they shared a common vision of emerging opportunities. “Brent believes in connecting projects across multiple platforms,” Kimmel says. “That philosophy appealed to me in a big way.” Okay, but how are the two going to divide up the labor? “While I am focused on the ‘monkey,’” Kimmel says, “he is focused on the ‘business.’” (In fact, Kimmelot is off to a distinguished start: its Live in Front of a Studio Audience: Norman Lear’s All in the Family and The Jeffersons, using original seventies scripts, won the 2019 Emmy for Outstanding Live Variety Special.)

The Wheelhouse concept was slightly less ambitious at the outset, in January 2018, before Kimmel signed on. Montgomery had observed how certain reality stars cleverly flourished as businesspeople. The prime examples are Chip and Joanna Gaines, who used Fixer Upper to expand their original decorating and renovating business, then to create new ventures, such as an online market. Their Magnolia brands became far more profitable than the show. “They’re going to build a billion-dollar business” employing Fixer Upper as a marketing tool, Montgomery says. This leveraging dynamic now has the potential to explode for others. “Netflix and all these channels are global with the flip of the switch. It used to be that, maybe three or four years into Pawn Stars, it’s in India and other countries; but now everything is global overnight.”

Most reality stars, however, lack the Gaineses’ flair for maximization. So Montgomery thought, what if he did it? What if, under one roof, he produced a film or TV series, marketed the stars and invested in their businesses? Thus began the new animal that he’s created: part content house, part marketing machine, part venture capital firm, all working in concert. (In addition, Montgomery created incubating parties—Wheelhouses, he calls them. These actual, physical houses, one in West Hollywood and the other in Tribeca, are convivial hubs where artists, athletes, musicians, show runners, media bigwigs and investors meet to party with intent.)

“We kind of vet them to make sure they’re open-minded about dancing with people outside their own little industry,” Montgomery remarks. The Wheelhouses created buzz before the company did. Last year The Hollywood Reporter visited the Spanish villa-style Wheelhouse in West Hollywood and noted the presence, among others, of Game of Thrones show runners Dan Weiss and David Benioff, comedian Kathy Griffin, actor Jon Hamm, artist Shepard Fairey, Kimmel, GoldieBlox toy company founder Debbie Sterling, and assorted investors.

But Wheelhouse rests upon a foundation of content—a hip word that basically means story, scripted and unscripted. “This may be the coolest time to be a content creator, because it’s an arms race out there,” Montgomery says, noting the streaming revolution now in progress. Wheelhouse’s content division contains five groups—Spoke Studios (Wheelhouse’s own in-house production label; upcoming is the scripted series Tiger Woods, based on Jeff Benedict and Armen Keteyian’s bestselling biography); Kimmelot; Portal A; Den of Thieves; and Campfire. These content arms embrace everything from reality series to concert films to documentaries to scripted dramatic films. The recently acquired Campfire, for example, founded by Ross Dinerstein, is known for producing such quality work as the documentary Jiro Dreams of Sushi and the John Grisham nonfiction crime series The Innocent Man. Portal A, in which Wheelhouse has a minority stake, focuses, by contrast, on making entertainment specifically for digital platforms—videos and branding you might see on HBO or YouTube.

In Montgomery’s expansionist worldview, all of this—the studios, the marketing, the investing, the elite gatherings—was not quite enough. Wheelhouse needed a proper home. Though it has offices in Los Angeles and New York, a headquarters called Stamford Media Village is now in the works, overlooking the water at 860 Canal Street. An architect’s rendering shows a reinvented four-story industrial building with exposed brick, tall windows, rooftop greenery and a waterside restaurant. “We wanted to create something significant enough and cool enough for talent to relocate to,” Montgomery says, adding that visual media people who already live here would relish commuting to Stamford instead of New York. (Courtney, who founded her own business, Wheelhouse Properties, to engage her passion for building and renovating, is overseeing the project.)

Wheelhouse will share Stamford Media Village with ITV America, with whom Montgomery still enjoys a close relationship. We are likely to see films and TV shows emanating from the Village, some of them filmed in the region using local crew. Wheelhouse and ITV together hope to employ up to 600 people in Stamford.

Montgomery praises the State of Connecticut for its role in making Stamford attractive. Among other things, it gives tax credits for unscripted as well as scripted work. This is unusual but makes great sense, Montgomery says: “You go make a film for six weeks and then the carnival moves on. But when you talk about shows I’ve managed like Cake Boss or Pawn Stars or Fixer Upper, they provide jobs for years.”

For now, everybody is watching Wheelhouse keenly. Will its great flywheel wobble, or will it gather Disneyesque strength and speed? “If it’s anything like what he did at Leftfield,” says A&E’s Paul Buccieri, “he’ll have built two major media companies and solidified a legacy of influencing and impacting popular culture.” Investors are likewise confident. L Catterton’s Jon Owsley says, “Brent is a visionary who can conceive of a sweeping, game-changing enterprise, while at the same time being tactical enough to understand what is needed to build the pieces in order to achieve that vision.”

Montgomery describes his capacities in simpler terms. “Fortunately, or maybe unfortunately, I don’t know how to do anything small.”

Brent in his home theater – photo on screen courtesy of Spoke Studios
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