THE CONFIDENCE MAN

WORDS: CHRIS BAKER
PHOTOGRAPHY: RAINER HOSCH

Justin Kan had a crazy idea — he’d film himself 24/7 and somehow turn it into a company.

At his weekend home along Northern California’s rugged coastline, a place that Google Maps has yet to locate, Justin Kan gets away from his phone’s constant buzz and works up a sweat chopping down trees on his property or zipping around on his ATV. (They’re dead trees, so it’s not like he’s denuding Mother Earth or anything.) But during the week, the 33-year-old can be found mostly in his contemporary house in San Francisco’s Duboce Triangle neighborhood, where he checks social media constantly and works intensely with several startup companies who’ve set up shop in his home office. 

Some days he splits lanes on his Ducati Monster motorcycle to get to his other office down the coast in Silicon Valley. When he’s in city mode, Kan has to get his exercise in other, less photogenic ways. Most mornings he just heads downstairs to his garage, fires up some motivational music and climbs on his Exercycle.

As his legs are pumping, he points his phone at his face, grins and records a video. “What’s up, Snaps?” he says. “Getting my morning workout in. Fitness is the first step to greatness! The second step to greatness? Probably diet, but … I’m not on that step yet.”

His legs still moving, Kan reviews the video clip and hits post. He is doling out life lessons while he’s burning calories, and 10,000 eager Snapchat followers are tuning in to watch. In fact, there are a lot of people who’ve grown up watching Justin’s life unfold online.

In 2007, he turned himself into a reality show, filming everything that happened during his waking hours. Justin.tv’s “lifestreaming” proved to be unworkable as both a business model and a way to live. But it led to a platform called Twitch, which allows millions of people to stream a video feed out to the world, and made Kan very, very wealthy.

In a way, Snapchatting with fans who dream of creating their own successful company is coming full circle for Kan, who hustled his way through failure back when he was a scrappy kid, and drew on a deep well of confidence to maintain his sanity. Kan scrolls through the scores of questions that have come in from his followers overnight, looking for one to record a response to.

“I started getting into Snapchat in January, just f*cking around with it to distract me because I hate cardio,” he says as he stands up on the pedals. “I’d get bored after 10 minutes. Now I can answer questions for 40 minutes, and I don’t notice that I’m working out.” He finds a Snapchat question: “How do you stay focused while being active on social media?”

“It’s a huge distraction,” he concedes. “I mean, you’re being distracted by me right now. Most of my friends who are super successful are not very active on social media.” And thus, we arrive at the paradox of Justin Kan. Any life coach worth their exorbitant hourly rate would sternly warn you not to waste time on social media.

But Kan’s greatest successes have come from the fact that he lives transparently, giving an online audience glimpses of his daily life, his work, and his inner thoughts. “I’m on social media more than you should be,” he concedes, “but for me it’s a platform to reach an audience and educate them. That’s a worthwhile thing to do.” He wasn’t so high-minded when he first hit upon the idea to live transparently.

Kan fields pitches (in this case, ours) at his home in Sonoma County— check out his verdicts on our Facebook page. 

Back in 2007, Kan had an epiphany while he was riding around with friends and talking smack. Their conversation was so funny that he was sure that other people would enjoy listening to it. Maybe there was a way to capture the conversation and send it out over the internet? That’s how Justin.tv was born.

Back when GoPro was only offering a clunky camera that could take low-res 10-second clips, Kan literally strapped a webcam to his head and broadcast whatever was in front of him, all day every day.

The Justin.tv site gave an audience the ability to watch him, or to set up their own lifestream feeds. “For me, it was as much about pushing myself outside of my comfort zone as it was about business,” he says. “I was not very extroverted back then. Going out and trying to entertain people? That was hard as f*ck.”

He had already had a taste of professional success at this point. While he was still a student at Yale, he and eventual Twitch co-founder Emmett Shear created an online calendar service called Kiko. He downplays the quality of it now, but they managed to secure funding from Y Combinator, an incubator that helps out young startups in the hopes that they can reap rewards if they become massively successful.

Kiko did not, exactly, but the founders managed to score a quarter of a million dollars when they put it up for sale on eBay. Justin.tv was not an immediate success. He was generating buzz (including a Today show appearance) and garnering feedback, but the feedback was mostly exhorting him to go outside and do something more interesting.

Working out at his home three hours north of San Francisco includes wood-chopping. 

The platform taught Kan to be entertaining, but also that his everyday life was just not that watchable. “We didn’t know how to run a business, and we weren’t even good programmers,” he says. “We just had a really high opinion of ourselves, and we never gave up. We bumbled our way to success.”

They encouraged users of the site to start their own streams and quickly discovered that gamers were particularly receptive to making and watching streams of their play sessions. The site Twitch was soon spun off and its audience grew exponentially, Now there are over 1.7 million broadcasters on the site, livestreaming their play sessions and commentary for an audience of over 100 million viewers. Broadcasters can make money from ads on their streams, and even more money from viewer subscriptions. Many of the most popular ones now make their living from streaming.

“OUR COLLEGE SELVES COULD NOT HAVE DREAMED ABOUT THE LIFE WE’RE LIVING RIGHT NOW.”

In 2014, Amazon snapped up Twitch for the staggering sum of $970 million. That same year, another of Kan’s startups called Exec sold for an undisclosed but moderately gargantuan wad of stock. Oh, and another Justin.tv spinoff called SocialCam had already been sold to Autodesk for $60 million a couple of years before. “I was just joking with the co-founder of Twitch about this,” he says.

“Our college selves couldn’t have dreamed about this life we’re living now. It’s not so much about buying expensive shit, it’s just having the freedom to do whatever you want.” Back on the Exercycle, Kan is answering some highly technical questions about digital marketing with Facebook Ads and Google Adwords. He wipes the sweat from his forehead, then he embellishes his Snapchat clip with some businesslike emojis—charts and graphs and whatnot.

As he records his videos, he aims his phone’s camera at various toys in his garage that help emphasize his points. The contents here reflect his eclectic interests. There’s the stylish business-guy side, represented by his Mercedes SUV. There’s the jock side, represented by tennis rackets and mountain bikes. And then there’s Kan the Burner: the confetti cannon, the DJ equipment and the hulking speakers still caked in Playa dust from his last trip to Burning Man.

Soon. See you at twitch.tv/twitch. #PAXSouth2015 #PAXSouth

A post shared by Twitch (@twitch) on

He doffs his shirt as he scrolls through questions and picks another one to respond to: “I’m 17 years old, about to go into my senior year of high school. Any advice you can give to young investors?” “My main advice is don’t invest any money that you can’t afford to lose,” Kan replies. “Especially in tech companies.” “People know about successes like Twitch,” he says. “But successes like that are what happens 5 percent of the time, surrounded by 95 percent of struggle, of times when you’ve just got your head down and you’re working. Or when nothing is coming together and you just want to give up.”

The one thing I would tell people is that everything worth doing takes a lot longer than you think. Whatever your goal is—to make the next Twitch or be a doctor or a tennis pro—you have to gradually assemble the building blocks.” The sage wisdom he dispenses now is rooted in countless failures. And as he’s transitioned from builder to investor— he’s now a partner at Y Combinator, the incubator that gave him a chance out of college—the lessons continue. He’s invested $50 million in 25 different startups—some have led to major acquisitions, many others have foundered.

“SUCCESSES LIKE TWITCH ARE WHAT HAPPENS 5 PERCENT OF THE TIME, SURROUNDED BY 95 PERCENT STRUGGLE.”

“There’s no trick or hack to making it,” he says. “You have to have an idea that’s powerful and concise. You also have to be mindful and open about all of the challenges you will face and how you plan to deal with them.” Many of the companies Y Combinator chooses to work with are at an embryonic stage of development.

At that point, you’re gambling on the future potential of the team behind the product. “A lot of it is gut instinct,” he says. “Are these good people who work together well? That’s just as important as having a great idea.” What is the key trait to success? “Relentlessness is super important,” he tells me. “Are you going to give up when you hit a wall, or power through and figure out a solution?”

After he finishes his workout, he’ll be headed down the coast to coach some startups prepping for an event called Demo Day, a chance to publicly pitch their products to investors. It’s much like the pitch sessions you see on the HBO show Silicon Valley, of which Kan is a fan. He attests to the accuracy of the frivolousness and petty sense of entitlement depicted on the hit series. (For the record, when I ask him which character on the show he most resembles, he says, “A little bit of Erlich Bachman, a little bit of Peter Gregory, and a little bit of that douchebag guy who drives a Lamborghini.”)

Justin Kan's license plate

The vanity plate on Kan’s Mercedes proves he doesn’t lack certainty, though he admits to having struggled with being on camera 24/7.

Most of the advice Kan gives is not so much what to say but what not to say. “I’m always telling them to refine and refine,” he says. “Trim away the parts of the story that aren’t compelling and remember that no one will care about your product unless they know what problem it’s going to solve.” It goes against his normal Exercycle Snapchat procedure, but Kan asks me to pose a question to him directly so he can answer it for his fans. He points his phone in my direction before I have a chance to beg off.

“W- what have you learned about, uh, listening to your, um, audience?” I stammer, wishing I could sink into the floor. How the hell does he make living in public look so easy? “Listening to the audience is where the idea for Twitch came from,” he replies. “When we first started, we didn’t do any research, didn’t ask broadcasters what they liked, and we were working with an idea that was fundamentally horrible. But we saw people streaming themselves playing video games and we said, ‘Let’s do more of that.’ 

Busy reading YC applications 😎📖

A post shared by Justin Kan (@justinkan) on

If a bad idea like Justin.tv could turn into something successful, you have no excuse not to be relentless and keep trying. You have to be a fast learner, but I think the success that we had is achievable by a large number of people.” After he sends out the video, he tells me he’s convinced that there’s still huge untapped potential in streaming sites built around other activities besides games.

For instance, Live.ly is creating a community around live-music streaming. Twitch itself has launched a Creative channel for activities like painting, drawing, dance and cooking. “There’s a lot more innovation to be done in video,” he says. “People say, ‘Oh, it’s all been done by now.’ But every time you think that it’s over, something new comes along.” Kan sags on his bicycle seat and records one last message into his phone. “Alright Snaps, I’m gonna call it, I’m f*ckin’ beat,” he says. “So long! See you next time!”

Read more
11 2016 THE RED BULLETIN

Next story