This story appears in the March 2021 issue of Entrepreneur. Subscribe »

The scene opens in hell. We see flames. We hear screams. Then the camera closes in on Satan himself — big horns, giant pectorals, bright red skin — as he slumps over on his throne. His phone buzzes. He glances at the screen. “You’re a match!” it says. Satan perks up, eyes wide in amazement. The dark lord, it appears, is looking for love on Match.

Cut to: a bridge underpass, in a park on Earth. There are trees. It is quiet. Satan waits to meet his date. A woman approaches. “Hi, Two-zero-two-zero?” Satan says to her. “Please,” she replies, “call me 2020.” Then it’s montage time: Satan and 2020 picnicking in an empty football stadium, doing yoga in an empty gym, stealing toilet paper and hanging out by a Dumpster fire, and generally setting their hearts aflame as they watch the world burn.

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When this ad for Match debuted online in December 2020, it triggered an instant lovefest online. Ryan Reynolds expected as much. He cowrote and produced the spot for his marketing company, Maximum Effort, which has become one of the hottest in the advertising game. “I would have paid for [the Match ad] myself just to make sure we got it done,” Reynolds says. “I felt pretty confident that it would work. And when it did work, then I would go bill them back.” He laughs. But don’t worry about his compensation: He’s also on Match’s board.

Reynolds used to dislike marketing. He saw it as an obligation. And anyway, he was an actor; the marketing was for other people. But then, he spent a decade trying to turn the oddball Marvel superhero Deadpool into a movie — and even when 20th Century Fox finally got on board, the studio remained skeptical of its potential. So he teamed up with one of the studio’s marketing execs, George Dewey, who’d spent 15 years at the giant ad agency McCann, and they launched a ridiculous guerrilla campaign that stirred up so much excitement that Deadpool became the highest-grossing R-rated movie of all time. (And so did its sequel.)

“We started to look at marketing as a completely different tool we had in the shed, and something we could really tell stories with,” Reynolds says. “Everything is storytelling; if you’re not paying attention to that, then you’re just broadcasting and not engaging.” He and Dewey joined forces to build Maximum Effort, which has since produced consistent viral gems for a range of projects, including companies Reynolds owns (most notably Aviation Gin and the low-cost wireless company Mint Mobile). “Now I look at marketing as one of the great joys of my life and my business.”

Recently, while shooting a film in Vancouver, Reynolds stepped away to share what he’s learned about pushing the boundaries of what’s creatively possible — and pushing himself (and his team) to constantly reinvent.

Tell me about your creative process. When you sit down to come up with something like that Match ad, where are you starting?

You know that line about how Shakespeare smuggled poetry into popular works? Well, we’re kind of the opposite. We really feel like, when somebody is watching an ad, there’s no reason it cannot feel extremely entertaining and inventive and fun.

We want to bend, not break. We want to be able to comment on something like 2020 without being disrespectful to the grimness of that situation. So you’ve got to give yourself some guardrails — and we love guardrails. Problems are our best friends, because they really inspire ideas and ways to create. Even if it’s just “Our budget has to be X.” We can still get the job done, and we have to think outside the box in order to deliver something that is of great quality. I mean, showbiz will teach you that. If you keep throwing money at a problem, that problem is only going to be exacerbated.

I’m reminded of something I’ve heard you say before — that you’re happy Aviation Gin had a smaller marketing budget than its large competitors, because it forced you to be scrappier with your marketing.

If somebody says, “You have $10 million to go shoot an ad,” the reflex for most people would be to say, “OK, so let’s start with some helicopter shots. The city’s in peril, a superhero comes and lands and uses a skyscraper to block out the alien ship.” Immediately, your brain goes to scope and scale. But scope and scale can be character, too.

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This lesson was driven home to me while shooting Deadpool. Every time the studio took money away from our budget, we replaced whatever set piece we lost with character. Eventually that became the hallmark and defining characteristic of that property. People don’t remember saving-the-world kind of nonsense. They remember what he said, or how he reacted to a moment. To me, that lesson is worth its weight in gold, because you can penetrate the zeitgeist and make an impression without spending a ton of money, without busting the bank.

I mean, we live in a world that’s so reactionary, so there’s a lot to play with. But here’s a tenet of our work: We don’t want to be divisive. There’s enough of that out there. I know it sounds super saccharin, maybe a little nauseating, but when we talk about our company’s M.O., we talk about bringing people together. So when we talked to Match.com and they were nervous about this pitch — Hold on, your lead characters are Satan and a woman named 2020? — we had to reassure them that we’re not here to divide. We are here to embrace something and bring people together over a common experience. When people have an emotional response to something, or find something incredibly funny, it travels.

That seems to explain your marketing, which is often very simple. Most of the ads you produce are just a few people in a room, or you speaking direct to camera. And what you’re saying here is — a large budget can cause people to forget about human connections.

Yeah. I think audiences are numbed to spectacle. We’ve all seen superheroes save the day. We’ve all seen a city in peril. I mean, when we were working on our Peloton Aviation Gin ad, all we were doing is really just acknowledging the cultural landscape in that moment and doing it in a way that doesn’t attack Peloton. [For context: In 2019, Peloton released a cringe-inducing ad featuring a woman whose husband buys her a Peloton bike, and she becomes uncomfortably obsessed with it. Critics and consumers tore it apart, interpreting the ad as sexist or tone-deaf. Days later, Maximum Effort released an ad featuring the same actress, looking shaken, downing Aviation Gin martinis at a bar with two girlfriends and toasting to new beginnings. It was widely praised as one of the greatest ad moments of 2019.]

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I just thought there was such an interesting redemption to that. If we could find Monica Ruiz, the woman in the Peloton ad, we could give this a side B — a look at this person from a different perspective, in a way that acknowledges and plays with the cultural landscape and the zeitgeist but still is only there to have fun with it. Not to further divide. Not to wag our finger at anybody or vilify anybody. Just to acknowledge this thing.

We found Monica — I called her four or five different times because she was so nervous that this would backfire. It’s already so alienating when you’re the subject of all of that energy and attention. But we did it. It was really where we started talking about “fast-vertising” — doing things with a speed and agility that others can’t, because Aviation Gin is owned by me, so I don’t really have to go up some huge corporate ladder. I can just say, “Let’s do it.”

You just told two stories — Match and Peloton — in which you approached a potentially controversial subject and had to convince others that you mean well. What’s your strategy for talking people into seemingly scary ideas?

It’s convincing them that I’m as risk-averse, if not more than they are. You want to be able to do something where everyone feels like you’re being provocative but nobody feels vilified, attacked, or nullified. It always comes back to that same edict: Let’s bring people together. Let’s filter everything we do through a prism of joy, as opposed to cynicism or division. I mean, division is very viral, but it’s not our bag. And it’s boring.

Your ads can be self-referential or feature you as an overly confident dummy. Like the ad about Aviation Gin’s partnership with Virgin Atlantic. The setup was that you and Richard Branson were making an ad about the announcement, but you barely understood what was happening. Where does that instinct come from, to flip advertising on its head?

It just depends on what we’re doing. I mean, with the companies I own, I feel an obligation to be transparent. It doesn’t mean that transparency can’t be soaked in irony or self-awareness or silliness. When it’s me out in front, usually I’m playing with preconceived notions about celebrity or about the commercial space. We lean into the things a lot of people traditionally lean away from, which is “Hey, this is an ad. We are acknowledging and playing with the cultural landscape in this ad. And we are telling you that we’re doing that.” It allows people to be a part of it.

If I’m zooming out even farther, I look at our company, and our goal is to radically improve. But you don’t radically improve just on creative, because everyone is going to have great ideas. It’s our goal to radically improve in new and inventive ways. Rethinking things is our favorite thing to do, too. If I hadn’t second-guessed every decision I made since I exited the womb, I don’t know that I would be in the position I’m in. I think it’s OK to rethink things — even good ideas! I mean, if you’re satisfied with just making money, you’re not going to be a disruptor for very long.

As any entrepreneur knows, there’s a difference between wanting innovation and creating a culture that fosters innovation. How are you doing it?

I always say that you can’t be good at something unless you’re willing to be bad. And as I’ve gotten older, I’ve gotten way more comfortable with not having the answers. I think it’s such a great tool of leadership to be able to say, “I don’t know.” The worst leaders I’ve ever worked with or been around are the ones who are steadfast and indignant in their righteousness, and really worried about their image. So I love saying, “I don’t know.”

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Everyone at the company has different specializations and different interests, which we foster and want to grow. I want the people who work at Maximum Effort to feel like they’re the CEO. I want everybody pushing toward a direction that is really inspiring for them.

And that’s worked so far. I don’t pretend to know how exactly to run a company. But I think that people who run companies, they don’t know either! It’s great to stay curious and in the moment. Innovation is always born of curiosity.

You have an ability to stay a step ahead of culture — to engage with the next part of the conversation. What’s your advice on how to do that?

Well, you’d be a moron to not acknowledge the now. But as a company, we talk about 2022 right now. It’s just that balance of: We love culture. We know culture is typically very now. But we also love thinking ahead, and looking at where we would like to be, and what we would like to be doing, and trying to manifest that to the best of our abilities.

Source: Entrepreneur

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