He Helped Usher in the Reality TV Era. Now He’s Writing a New Hollywood Playbook

The founder of an entertainment company with ABC late-night star Jimmy Kimmel on board as a partner, Montgomery produces content for traditional TV networks and streaming services such as Netflix and Hulu. He also backs internet celebrities and manages talent.

His company, Wheelhouse Entertainment, sold 20 TV series this year, its highest number ever.

The portfolio at Wheelhouse spans Kelly Ripa-hosted ABC show “Generation Gap;" “Love and WWE," a relationship show headed to Hulu starring married wrestlers; Brooklyn Beckham’s cooking-show, and managing TikTok stars such as Nicky Champa (13.1 million followers) and Jack Wright (11.4 million followers).

In the entertainment cosmos, cable and broadcast TV, streaming and social-media platforms orbit each other but haven’t yet collided. Montgomery, with an eye for the absurd and a keen sense of how consumer tastes are evolving, travels among all of them, aiming to maximize the commercial potential of each.

He previously turned a family of Las Vegas collectors into “Pawn Stars," parlayed that into a reality TV production powerhouse with credits including the “The Real Housewives of New Jersey," and sold it for nearly $400 million.

In his view, the future of entertainment stretches far beyond content creation: Producers will be financially and operationally entwined with talent, helping them create business opportunities and build their brands. Talent doesn’t want to be work-for-hire—they want a partner that will help them expand their brand beyond a single project.

In addition to producing fees and royalties, Wheelhouse has sought stakes in the businesses whose stories it tells. It negotiated a stake in Goldin Auctions, the firm at the center of its Netflix show “King of Collectibles: The Goldin Touch," and secured profit participation with The Agency, the luxury real-estate firm featured in Wheelhouse’s reality series “Buying Beverly Hills."

Brandon Riegg, Netflix’s vice president of nonfiction series, said Montgomery “has done a good job reinventing what a modern production company should do. You see it all coming to fruition."

Wheelhouse’s partnership with celebrity chef David Chang and his Majordomo Media is a model of Montgomery’s approach. Wheelhouse and Chang initially co-produced the Hulu cooking-competition show “Secret Chef" and are now teaming up on new content and investments in consumer cooking products.

Across Hollywood, some media companies are trying to buy all or parts of production companies to diversify the range of shows, film and creative talent they develop.

Elisabeth Murdoch’s Sister studio takes stakes in production entities, while former Disney executives Tom Staggs and Kevin Mayer launched Candle Media, acquiring several production companies to create a programming portfolio. Few make content and invest in the subjects of it across legacy, streaming and new media formats the way Wheelhouse does. (The Murdoch family is a large shareholder in The Wall Street Journal’s parent News Corp.)

“Content has to do more than just attract viewers. It has to generate additional revenue streams," said Ed Simpson, Wheelhouse’s chief strategy officer. Montgomery recently raised a $50 million first-time fund focused on consumer and tech companies that Wheelhouse can amplify through its projects.

Programming about real people doing things—from the mundane to the profound—has proved to be compelling across generations. Videos on TikTok and YouTube featuring internet celebrities have become something of a cousin to reality TV.

Montgomery knows that young audiences’ attention has shifted away from 30-minute or hourlong TV shows in favor of shorter videos on social media.

“The next wave of talent is coming from the phone, and many will not necessarily have the appetite for long-form content or the staying power of long form," he said. His stable of shows and investments positions him to benefit from the new and old media worlds simultaneously.

Montgomery became intrigued with the creator economy several years ago when actor and Wheelhouse producer John Stamos introduced him to YouTube stars Casey Neistat, famous for stunts such as snowboarding through the streets of New York, and David Dobrik, whose prank and challenge videos helped him attract nearly 18 million followers.

“Their superpower was owning their voice and direct reach to their audience and converting content to commerce," Montgomery said.

Wheelhouse now manages social influencers and often participates in stars’ commercial ventures, such as soccer jerseys sold by top Twitch streamer Nick Bartels, who runs soccer-focused channel RunTheFutMarket. Bartels is known for his smarts on player trading.

One of Montgomery’s regrets? Not landing social-media star Charli D’Amelio as a management client. She became famous for posting dance videos on TikTok, boasting 151.6 million followers, and has appeared in several reality and other TV series. She has also launched fashion and makeup lines.

The company has become known for its frequent gatherings of industry executives, athletes, actors and influencers that are half party, half networking events. Attendees have included Netflix Co-CEO Ted Sarandos, boxer and YouTube star Jake Paul, WWE Chief Executive Nick Khan, Al Pacino, John Mayer and Peyton Manning.

Montgomery bounces between Los Angeles, New York and Wheelhouse’s headquarters in Stamford, Conn., where he developed a $75 million waterfront media complex dubbed The Village, which is a short drive from WWE’s headquarters.

He has poured tens of millions of his own money into Wheelhouse and expects to turn a profit in 2024. The inspiration for the name is Walt Disney’s “flywheel" sketch, which outlines how the company’s famous characters drive the creation of content and commerce via films and television, comics, music and merchandise.

Montgomery’s relationship with Kimmel started in the old fashioned Hollywood way—an agent introduced them. Kimmel said in an interview that he had been considering life after late night and was interested in setting up his own production shop when he met Montgomery.

“It aligned with what I wanted to do," he said. The pair hit it off, and one of their first projects involved creating live versions of old sitcoms including Norman Lear’s “All in the Family" and “The Jeffersons."

Along with the shows, Kimmel’s Kimmelot media company partnered with Ryan Reynolds’s firm, Maximum Effort, to create retro commercials for Kool-Aid, Heinz and Oscar Mayer. Kimmel said he enjoys using his creative instincts to craft campaigns and promotional strategies.

Disney Television Executive Vice President Rob Mills said Kimmel joining Wheelhouse in 2018 as a partner “supercharged the operation."

Today, Montgomery is “making a mini-major studio," Mills said.

Write to Joe Flint at Joe.Flint@wsj.com