Rob McElhenney is betting on himself

Rob McElhenney is, quite literally, wearing many hats.

The 47-year-old actor, writer, showrunner, and entrepreneur is holding a polite grimace as he balances five fedoras atop his head in a Culver City studio, Imagine Dragons pumping in the background.

He places a sixth on top of the stack, slowly draws his arm down, and poses. The crowd — in this case, a photographer and a handful of assistants, publicists, stylists, and groomers — goes the Hollywood equivalent of wild (the photographer shouts, "You're amazing!").

McElhenney's posture is lighter as he strolls over to the photographer's monitor to check out the result, six hats still balancing on top of his freshly coiffed brown hair. His nerves? Gone. That grimace? A distant memory. He's on to the next shot.

Over more than two decades working in Hollywood, McElhenney's approach has been similar: the ambitious plan, the windup, the execution, the comedown. Then, the next ambitious plan. "It's not magic," McElhenney tells Business Insider a few weeks after his photo shoot. "It's just putting one foot in front of the other, getting the work done, and aligning yourself with the right people."

In today's entertainment landscape — one in which every celebrity seems to have a book club or a liquor brand, and many have broken into the ranks of writers, showrunners, and producers to make up for shrinking residual checks — multihyphenates are everywhere. Reese Witherspoon isn't just an A-list actor; she's built an entertainment empire with her production company, Hello Sunshine, by adapting female-focused books into movies and TV shows and selling them to streaming services. Kevin Hart has so many ventures (a tequila brand, a restaurant chain, a series of self-help books, partnerships with companies like Lyft and JPMorgan Chase) that it's easy to forget he's still doing standup comedy.

But not every workhorse can create the longest-running live-action American sitcom, as McElhenney did with "It's Always Sunny in Philadelphia," which is prepping to film its 17th season. And not every ideas guy can sell a cable network on his plan for a sports docuseries that also serves as free advertising for his businesses, then turn that show into a critical and commercial success, as he did with "Welcome to Wrexham," which is about to conclude its third season. To McElhenney, every story is a business, and every business is a story.

McElhenney's new company, More Better Industries, clearly lays out his ambitions. It includes a production arm, More Better Productions, to support projects like "Wrexham" and his AppleTV+ series "Mythic Quest"; a creative consultancy, More Better Advisory, to do things like integrate McElhenney's Four Walls whiskey into "Wrexham" and get it sold at Citizens Bank Park in Philadelphia; and an investment arm, More Better Ventures, to back sports teams, tech companies, and other businesses that slot neatly into McElhenney's interests. He has, essentially, commodified every public aspect of himself, folding in layer upon layer of potential cross-promotion and profit, all in a way that feels — as much as is possible with these kinds of things — organic.

It is, those close to him say, a very Rob McElhenney thing to do. "If you need to overcome a problem or manifest a miracle," says his good friend and "Wrexham" costar and coowner Ryan Reynolds, "tell Rob it's impossible."

But McElhenney is adamant that he isn't doing more for the sake of it. "That is an empty, unfillable cup in the center of your soul," he says. "You have to find something that you love and devote yourself entirely to it. Otherwise, you could've made a billion dollars and wasted your life."

Most Rob McElhenney projects start with a crazy idea. In the case of "Always Sunny," the template for the show's lovable-yet-despicable characters began with McElhenney's idea for a darkly comedic scene: A guy knocks on his friend's door asking to borrow some sugar, only to learn that the friend has cancer. Instead of being sympathetic, the guy just wants to grab his sugar and run.

McElhenney shot the scene, along with a few others, with his actual friends, Charlie Day and Glenn Howerton. All three were struggling actors in their late 20s living in Los Angeles, so their characters were, too. They put together a pilot that was picked up by FX, but the network had a key note: Change the location and the characters' jobs. (No one wanted another TV show about struggling actors.) McElhenney offered up his hometown of Philadelphia and a local pub where the gang would work. When the first season of "It's Always Sunny in Philadelphia" aired in 2005, McElhenney was 28 and the youngest showrunner in Hollywood. Nineteen years later, the show is still delivering the boundary-pushing comedy fans know and love while taking the occasional ambitious dramatic swing.

In theory, McElhenney could have ridden the success of "Always Sunny" into the sunset. But spending the pandemic lockdown bingeing sports documentaries gave him an idea for his next venture. Inspired by shows like Netflix's "Sunderland 'Til I Die" and the meritocracy of the English football league, where teams are promoted and demoted based on their record each season, McElhenney came up with a plan: Buy a struggling team for dirt cheap. Get a TV deal to document said team. Use the TV money to upgrade the team, which would make for a compelling Cinderella story. On paper, the plan was "insane," says Reynolds, whom McElhenney met about four years ago after the two struck up a DM friendship. "In reality, it's still completely insane."

But anyone who knows McElhenney knows he doesn't take big swings without a plan. McElhenney's wife, Kaitlin Olson, who met her future husband when he cast her on "Always Sunny," says witnessing his work ethic on the show was "definitely when I started to fall in love with him." When McElhenney pitched Olson on "Wrexham," she was instantly on board. "He's someone I would always bet on. His ideas always are so fleshed out and so thoughtful," she says. "It wasn't just about like, 'Oh, let's buy a team!'"

McElhenney brought his pitch to John Landgraf, the chairman of FX Networks, who agreed to pick it up for two seasons. It didn't matter that McElhenney had never made a documentary or that he knew hardly anything about English football and hadn't yet chosen a team to follow. "I did it because I trust Rob," Landgraf says. "The guy is a magnet for excellence."

Picking the right team was about more than tapping one lucky club to infuse with cash. To reverse engineer what McElhenney called "the ultimate underdog story," the team had to be as rich in narrative potential as it was in need of resources. The British comedian Humphrey Ker, a writer on "Mythic Quest" and an avid English football fan, suggested Wrexham AFC, and something clicked. The down-on-its-luck club, situated in a postindustrial Welsh town, reminded McElhenney of his working-class upbringing in South Philadelphia. As the oldest English football club in Wales and the third-oldest professional team in the world, it offered a unique blend of legacy and opportunity: After sinking to the lowest position in its 150-year history, the only way to go, for both the team and the town, was up.

The fact that "Welcome to Wrexham" is a well-made, engaging documentary underscores McElhenney and Reynolds' insistence that helping the team rise through the ranks is about more than sheer capitalistic ambition. The coowners anchor the show as famous yet naive interlopers hoping to learn about English football and Welsh tradition. But the series also makes welcome forays into character study, highlighting fans like the singer of a local band called the Declan Swans, who's undergoing cancer treatment, and the team's volunteer disability liaison, who uses a wheelchair.

So far, the formula has been good for everyone involved. "Welcome to Wrexham" was recently renewed for a fourth season, and Wrexham AFC has been promoted twice and now sits two leagues away from its goal: the internationally renowned, massively lucrative Premier League. The docuseries has helped spike sales of Wrexham merch. Local businesses, including the team's regular pub, have become tourist attractions. And McElhenney and Reynolds have never been busier, engineering publicity stunts that pull triple duty as personal branding, advertising for "Wrexham," and extra exposure for the team's sponsors (some of which are their own companies).

From a different angle, however, the Wrexham gambit can feel a bit cynical. Landgraf has seen "snarky, sometimes bitter tweets" from opponents' fans suggesting that Wrexham recruiting players from higher leagues constitutes cheating or buying its way to the top. As the team advances through the leagues, the Hollywood influence on its growing profile has become even harder to ignore. When Wrexham announced its partnership with HP, it wasn't just McElhenney and Reynolds who appeared in cheeky ads for the information-technology company: Wrexham players did, too. There's also the clear class divide between the average Wrexham fan and the Hollywood celebrities who arrive in their working-class town with a camera crew in tow. No number of friendly pints with the locals can change the fact that McElhenney and Reynolds' efforts to revitalize the team and the town were made possible by their fame, wealth, and connections.

That fact isn't lost on McElhenney. While "Wrexham" takes pains to emphasize his blue-collar upbringing in South Philadephia, he's aware of the complicated dynamics at play. "I have to recognize that I'm no longer in the position that I was growing up," he says. "So I don't feel that I have the right anymore to fully understand what someone's going through. The only way that I can truly understand it is if I listen and listen and listen and listen more, and then try to synthesize that information and do with it what I believe is right."

All that listening doesn't seem to be an empty promise. Early scenes in "Wrexham" show McElhenney taking in the unfiltered thoughts of fans, some of whom are less than pleased with the celebrity takeover. "I don't like conflict, and yet I recognize that without a differing point of view, I'm just going to continue on the same path," McElhenney says, weaving in a tangent about President Lincoln's decision to fill his Cabinet with political rivals. "I won't learn, I won't grow, and I won't be able to understand where the world is headed."

Soaking up information is a core part of McElhenney's business strategy. He describes how he educated himself about everything from investing to running a company to buying a sports team by striking up conversations with people who knew more than he did.

While working on "Wrexham," McElhenney reached out to the Philadelphia Eagles owner, Jeffrey Lurie, and the team's general manager, Howie Roseman, to understand their perspectives on owning and running a team. He also talked to the former Philadelphia Eagles center Jason Kelce and his brother, the Kansas City Chiefs tight end Travis Kelce, to get the player's perspective. To Olson, curiosity is her husband's strong suit. "He doesn't see it as weakness to not understand something," she says. "He's perfectly willing to go, 'Wait, hold on, back up. Explain that again.'"

He's not above taking suggestions from complete strangers, either. In March 2023, Kelsey Trainor, a former entertainment lawyer, sent McElhenney a snarky Twitter DM about the Wrexham women's team playing their first game at the club's main stadium. "I said something like, 'Well, it's about time,'" Trainor says. A few weeks later, she was sitting on the beach in Turks and Caicos when she suddenly felt anxious about her plans to take a law-firm job and messaged him again. "I said, 'I just quit my job. I'm going to go make a lot of money, or you can hire me to work for your Wrexham women's team.' Two hours later he responded: 'That is the most badass DM I've ever seen. What's your number?'" Trainor is now More Better's chief strategy officer.

McElhenney's egoless hunger for collaboration may have started as a chip on his shoulder. As a kid, he struggled in school and was labeled a troublemaker who was always in detention. He was the only person in his class who didn't go to college. When he was diagnosed with neurodevelopmental disorders and learning disabilities at 46, his school years finally started to make sense. "It was truly revelatory," McElhenney says. He'd always thought he was trying his hardest in school, but "the way that the system was set up and the way that my brain worked just didn't line up for me to be successful."

In retrospect, he realized he wasn't actually a bad kid. "I just never felt like I could succeed. No matter what I did, I was going to fail, so why bother? So of course I started acting up."

Struggling in school wasn't just character building; it also was skill building. McElhenney references Malcolm Gladwell's book "David and Goliath" and his theory that people with learning disabilities are more likely to become innovators because they must work around a "strategic disadvantage." "In a lot of ways, I'm grateful for it," McElhenney says. "It helped me look at the world in a different way."

Having a family, too, has shifted McElhenney's perspective. After dating Olson first in secret, then openly on the "Always Sunny" set, the two married in 2008 and had two sons, Axel, 13, and Leo, 12. It may seem as though his various jobs bleed into every aspect of his life, but McElhenney has worked hard to keep parts of himself separate. He has one text chain with Reynolds and other Wrexham leadership about their business partnership, and one with just Reynolds that's strictly a friend chat. In between sending memes back and forth, they talk about how to strike a healthy work-life balance and how to show up as good partners.

One text in particular has stuck with McElhenney. Reynolds "said something to the effect of: 'Just make sure that, no matter what, you leave space for what's most important, which is your kids. And to be able to twirl Kaitlin on the dance floor,'" he says. "To see that written out? That felt poetic."

McElhenney cites his "Always Sunny" costar Danny DeVito and DeVito's wife, Rhea Perlman, as some of his and Olson's parenting role models. "The trick is not much of a trick at all," he says. "It doesn't matter if you are the poorest person in the neighborhood or the richest guy in Bel Air. If your parents give you unconditional love with boundaries and respect you and spend time with you, you're probably going to be OK."

Like the teams in the English football league, McElhenney's success may come and go. "Welcome to Wrexham" might have secured another season, but even Landgraf says there's no guarantee that the series will air indefinitely. Because reality dictates the narrative, the team's travails must remain interesting enough to document — a feat that might become more difficult as Wrexham sheds its dark-horse status. Not to mention the finances: The team's losses reportedly soared to $6.4 million in the 2022-23 season, partly due to increased player salaries, despite having big sponsors to help foot the bills. The owners acknowledged they might have to seek outside investors to get the team to the next tier.

But boundless curiosity and a bit of an underdog mindset have gotten McElhenney this far. Ultimately, he just wants to make the things — and invest in the people — he believes in. "If I could spend the second half of my life saying that to other people, and then putting my money where my mouth is and watching them go and build what they want to build," he says, "I feel like that's a life's worth living."

Credits:
Photography: Sheryl Nields
Creative Director: Bryan Erickson
Styling: Kelsey Ellstrom
Hair: Lesley Poling
Makeup: Corina Duran-Rabichuk
Producers: Nicole Hyatt, Rebecca Karamehmedovic, and Jennifer Laski for Sway NY
Photography Assistance: Danya Morrison, John Cizmas
Digital Tech: Embry Lopez
Design and Development: Jenny Chang-Rodriguez, Bryan Erickson, Rebecca Zisser
Editing: Claire Landsbaum, Joi-Marie McKenzie, Jonann Brady, Marisa Frey
Editing Assistance: Brea Cubit
Video: Yuelei Song, Brittany Stephanis, A.C. Fowler
Social: Virginia Alves, Victoria Gracie, Nicole Forero, Laine Napoli

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