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Long before building the first

prototype of Snapchat, in 2011, Spiegel and cofounder Bobby Murphy worked on a platform called Future Freshman, which helped prospective college students manage the application process. Spiegel was the designer. Murphy was the engineer. Together, they worked 18-hour days for weeks, side by side, living off takeout, sleeping on-site, and ultimately building a product that flopped. “Despite that going nowhere, we really enjoyed working together,” says Murphy. “Partly, we were friends. But we also had different skill sets coming into our project, me being more on the development side and him being much more on the design side.”

The handoff that needs to happen between design and engineering was “super easy,” Spiegel attests. “We were sitting at the table together. Literally, you don’t have to try—it just happens, right?”

That dynamic worked when Snapchat was two people, and even when it was 20. But between 2015 and 2016, the staff ballooned from 600 people to almost 1,900. All those new folks, while talented, lacked the Spiegel-murphy shorthand.

Spiegel adapted poorly. As has been widely reported, he turned inward. If he aspired to be the next Steve Jobs, he seemed to have adopted the worst parts of the archetype, demanding full strategic oversight and creating a culture of secrecy. Snapchat was still a fun-loving viral sensation on the outside, but Spiegel came to realize that he had built an organization he didn’t recognize, something that was making him personally miserable.

Spiegel—the same CEO who once told a 38-year-old journalist confused by Snapchat’s user experience, “You’re not really the target”—embarked on a quest for self-improvement. “I mean, obviously I’ve never done this before,” says Spiegel, jocularly, of becoming a CEO at 21. “I think I’ve basically had to learn everything.”

He began by enlisting CEO adviser Steve

Miles to become both a personal mentor and a coach to the executive team. Miles, like most people I talked to within Snap, describes Spiegel as an open-minded tester and questioner. “He’s very Socratic,” Miles says, describing the first 90-minute walk that he and Spiegel took together on the Santa Monica beach.

Spiegel also started consuming the kind of management books people buy at the airport, including Loonshots, by Safi Bahcall, and The Power of Positive Leadership, by Jon Gordon. Following a wave of user revolt over Snapchat’s redesign, he rallied the troops in a 6,600-word memo in September 2018 that included the passage, “And Jon Gordon writes, ‘We are not positive because life is easy. We are positive because life can be hard.’ Positivity is what we use to overcome challenges and negativity. Being positive requires hard work. Being positive is a choice.”

Not everyone wanted to make that choice—or Spiegel made it for them. Ten senior leaders left over the next four months, including two who were fired for their role in an inappropriate relationship with a contractor. The exodus looked bad, but it was necessary to repair the company. For Snap’s next phase, Spiegel assembled a new executive team with more experience, including chief strategy officer Jared Grusd (a Huffington Post and Google veteran), CMO Kenny Mitchell (Gatorade and Mcdonald’s), CFO Derek Andersen (Amazon), chief communications officer Julie Henderson (21st Century Fox and Newscorp), and chief product officer Lara Sweet (AOL).

Outside, the doubters crowed, but inside Snap, the worst was over.

Gradually, Spiegel began to figure out where

he had gone wrong, deconstructing how he had organized Snap from the beginning. He had tried to model Snap on Apple’s early days, where one or two men appeared to invent everything. As a result, Spiegel had created a hub-and-spoke model. He, of course, was the hub; the spokes were the executives and managers across the company, whom he’d meet with individually and who weren’t necessarily privy to what the others knew.

Was there a reason that Spiegel championed private, one-on-one meetings?

“Not a good reason,” he says, laughing. The alternative, as Spiegel saw it, was operating like a big, efficient corporation such as Samsung or Foxconn. “These giant organizations are incredibly good at execution,” he says. “They’re very hierarchical typically; they have a lot of process. But those types of organizations aren’t particularly good at innovating.” While Spiegel was working on himself, he was also studying how he could maintain Snap’s innovation while applying the appropriate amount of process. “I’ve been super lucky to meet a ton of people who have been unbelievably generous in sharing how they think about the world or how they structure their teams or just helping us solve problems,” he says. Ultimately, he concluded that the answer for Snap was to combine the way he loved working with Murphy with the effectiveness of a Foxconn. The CEO now spends half his time with his rapid innovation team, a group of 12 designers who work on his floor. They act as a collection of peers focused on developing the future of Snapchat. His rectangular desk sits at the far end of a long room of workbenches; no walls or soundproof glass separate him from his design peers. Inspired by Spiegel’s experience taking classes at the acclaimed Artcenter College of Design in Pasadena (while still in high school), the innovation team gathers every Tuesday and everyone is required to show work, Spiegel included, even if it’s their second day on the job. “Because everyone is in it together, making a bunch of stuff, it’s okay to be really open and direct with each other because you’re going to have a zillion more ideas tomorrow,” Spiegel says. “That combination of a super-high velocity of work, art-school style, plus a deep understanding of human beings is how the team works.” Spiegel’s new executive corps then helps implement these ideas throughout the organization. “People talk about an innovation culture all the time, all day long,” Spiegel says, “but actually what you need is an innovation structure.” Miles, who continues to work with Spiegel and his senior leadership team, says that Spiegel “used to be a secret guy who nobody saw or heard from, a master Evan. He’s really evolved to a much more open, transparent, distributed model of leadership.” Spiegel tells me that most meetings are now team meetings; one-on-ones are devoted to helping people with their personal growth. Change has been messy at Snap, but it’s also been relatively swift. Spiegel has executed this transformation in just three years, while running a public company and becoming a father to three children. When we meet, he’s technically still on paternity leave after his wife, model-entrepreneur Miranda Kerr, gave birth to their son Myles. For all these reasons, Spiegel says, he’s “infinitely” happier at Snap than he was a few years ago. “I’m the first one in the office every day. I love it. I run here,” he says, before qualifying his claim with a chuckle. “Some days I do school drop-off, but other than that, I’m the first one.”

To understand both the near and long-term

future of Snap, it helps to rethink the entire notion of “content.” Today, there are two main types of content on Snapchat. The first: videos to watch on the app’s Discover tab, the closest thing the digital realm has built to cable TV. Snap has turned its crowdsourced videos into series, such as Oddly Satisfying, which shows Snapchatters performing mesmerizing tasks like popping bubble wrap. The company has also developed its own original series, which are notable for how they speak to Snap’s predominantly 13-to-24year-old audience, how well they play with Snapchat’s functionality, and how impeccably they’re produced. A guilty pleasure called

Second Chance places two exes together. Only one wants to get back together, and drama, lies, laughs, and deep truths unfold in a matter of just a few minutes, a love story told for a high school attention span. Each 10-second clip ends with a cliffhanger.

The second form of content is a suite of digital effects that enhance communication between friends, increasingly emerging from Snap’s investment in augmented reality. Recent examples include being able to transform yourself into a dancing chicken meme (courtesy of a new product called Cameos, powered by technology Snap acquired late last year) and a game called Snappables, which challenges players to find eight objects within their actual world via Snapchat’s camera function.

Moving forward, Snap will mix the two together. Content “is the dominant use case of AR today,” says Spiegel. “Most of AR is content overlaid on the world, overlaid on your face.”

Sean Mills, the company’s head of content, says that one of his big challenges this year is bringing augmented reality into entertainment programming as “a necessary component.” In 2018, the aforementioned teen series Endless Summer gave fans the chance to open an AR portal within Snapchat that made a beach appear wherever they were standing, complete with the show’s cast enjoying a bonfire. “When I make a show, I control 100% of the pixels,” says Mills. “When

you’re doing something with AR, you’re giving over like 80% of the pixels to the audience to reshape the narrative. That’s going to be a very different experience.” But Snap also wants to create entertainment around your relationships with friends. In February, the company debuted a new series called Bitmoji TV. Bitmoji, which Snap acquired in 2016 (a year before Apple’s Animoji), is an app that allows users to make a Simpsons-esque caricature of themselves and use that quirky avatar as another tool for expression. Bitmoji TV now takes this a step further, casting your avatar and those of your friends as the stars of a 10-episode animated series, a playful riff on Saturday morning cartoons that also parodies such TV stalwarts as American Idol. The result is not only engaging but pulls users deeper into Snapchat. Snap is also working to expand augmented reality from applying filters to people’s faces—selfie mode on their phones—to the world around them as seen through the camera on the back. “Everyone’s face feels unique and relevant to them,” says Murphy, who as CTO oversees the technical development of Snap’s AR products. “So the same piece of content applied to my face looks and feels very different than if it’s applied to yours.” The hurdle with everything that’s not a face? The world doesn’t hold that same degree of familiarity. Late last year, new partnerships with Coca-cola and Mcdonald’s represented the first time that brands could buy an advertisement for Snap’s Scan feature, which debuted the previous spring. It allows users to aim the Snapchat camera at a can of Coke or a carton of Mcdonald’s fries to unlock secret lenses, such as a polar bear that appears on your table. It’s no coincidence that the first two companies to use Scan are among the world’s most recognizable brands. The more ubiquitous the partner, the more AR content for Snapchatters to find when they point their camera out into the real world. It’s a playbook that the company has executed successfully in the past. Snap enlisted omnipresent brands such as Gatorade to popularize AR lenses by allowing users to dump virtual tubs of fruit punch on their heads, and, yes, Mcdonald’s, to make location-based snaps commonplace by letting customers unlock french fry photo filters—but only when visiting the chain’s restaurants. “The challenge is, from a Snapchatter point of view, ‘How do I know that there is an experience there?’ ” Murphy says. He anticipates that we’re moving toward a world in which every object has a hidden AR component just waiting to be revealed. But “‘How do I unlock [it]?’ We need to set up some expectation with Snapchatters around what’s scannable and what’s not.”

“Because we have all these amazing lenses

that people are using, you can start asking yourself questions like, Which of them would be 10 times better if the field of view is this big?” Spiegel says, raising his hands to eye level and spreading the distance between them from the size of a baseball to that of a Thanksgiving turkey.

Spiegel, like many of his tech CEO peers, believes that after smartphones, the next wave of computing will be some form of headset. But unlike, say, Apple or Facebook, both of which are reportedly working on AR goggles of some sort, Snap continues to develop its Spectacles AR sunglasses—in public. Spectacles 3, the company’s third iteration in as many years, adds a second camera to the headset, allowing the viewer to record the world in 3D and add effects with true depth.

The original Spectacles, which were released in November 2016, were a media sensation but, ultimately, a flop that would cause Snap to write off $40 million in unsold hardware. Still, the company knew it was onto something. “Anyone who had that data in front of them about where sales were going in the beginning,” argues Snap’s hardware director Steen Strand, “would [have found it] hard not to be seduced into this idea that you’re a runaway hit.”

Before joining Snap, in late 2018, Strand designed airplanes for Icon Aircraft— products, he says, that can have no “fat,” or they simply won’t fly. “A product like this?” he says, gesturing to Spectacles. “You can’t have fat either.”

This creates an interesting tension, because Spectacles—unlike the Microsoft Hololens, a bulky, hologram-filled headset that’s being marketed mostly to factory workers and enterprise customers—needs to be both fashionable and functional. At Art Basel in Miami Beach, in December, Snap worked with filmmaker and artist Harmony Korine (2019’s The Beach Bum), whom Spiegel personally recruited, to make a three-minute short shot entirely using Spectacles 3 and to create 50 hand-painted, limited-edition, Gucci-branded Spectacles that shimmer with an iridescent flare. They became a prized take-home for the creators at Art Basel who were gifted a pair, and their outré nature was the point: Making a wearable computer that’s actually cool is inherently risky. Strand and Spiegel readily admit that AR headsets are likely a decade away from mainstream adoption (a rare point on which Snap and Facebook agree. Facebook did not respond to a request for comment on this story). So why is Snap still making Spectacles at all? Why not let Microsoft or Apple (which is reportedly targeting a 2022 release) pump their unlimited R&D budgets toward AR headsets and then, when those hit the market, just swoop in with a similar product—and a stockpile of a million digital lenses to make them desirable? “The next 3 to 10 years are ours to lose, because we already have this huge community of people engaging with AR all the time,” says Spiegel. He grabs a paper and pen to illustrate his point. He draws a rectangle, divided diagonally into two triangles. On the left one, he writes “iphone.” On the other, the one that will soon push the first triangle into the corner, he writes “Spectacles.” “Over the next 10 to 20 years, iphone [usage] is going to migrate to Spectacles,” he says. “So the question is, on what timeline? What’s interesting, though . . . if we lose this [hardware] bet, it’s still okay, because we have the [digital] AR platform. We’ll still have a very, very large business. But what would it look like if we also win the hardware piece? Why wouldn’t you try?” That mantra applies to a lot of Snap decisions. Create an internet that can selfdestruct? Why wouldn’t you try? Produce original series in vertical format? Why wouldn’t you try? Build your own thing instead of selling out? Why wouldn’t you try? Leaving his office, I take another look at Spiegel’s desk and imagine him working there alone in this giant room, polishing his own design projects for Snap in the quiet, early hours before the rest of his team arrives. Behind his desk are dozens of framed prints and notes. One message stands out from the sea of ephemera. It says the one thing you’d think a 29-year-old billionaire who had just turned around his company would never need to hear: “You’re doing a good job.”