The Mayor of the Internet Has a New Mission

Erlich?

“It has been said that there was inspiration there, but I don’t see it at all,” Ohanian says. He explains that some viewers drew parallels between Erlich Bachman’s fictional travel-booking startup Aviato and Huffman and Ohanian’s real-life endeavor, the travel site Hipmunk. “I was like, ‘That doesn’t make any sense,’” he says. “I don’t see that at all, but whatever.” (The character comparisons he does see: that the late Peter Gregory character is part Paul Graham, one of Ohanian’s first supporters, and part Peter Thiel, Tan’s former boss.)

Rise of Reddit

Ohanian’s actual personal arc is far too dramatic and silly even for a Silicon Valley script anyway; it’s like something out of an earnest “By age 35 you should …” meme. His rise to prominence was so sudden — Reddit was only 16 months old when Ohanian and Huffman sold it to Conde Nast and became multimillionaires at age 22 — that his success feels both wildly aspirational and weirdly achievable, at least in a “well, if he can do it …” sort of way. Even his early setbacks felt relatable to media types: In 2010, when he left Reddit and spent a few months living in Armenia, it was practically a rite of passage. You haven’t truly made it in New York City, after all, until you’ve quit a Conde Nast job during a recession and headed abroad.

And then there was his relationship with Williams, whom he met in 2015. One minute Ohanian was just some nerd visiting Rome to speak at a tech conference; the next he was the type of guy who attends a royal wedding, is followed around by HBO cameras, and sits down with Stephen Colbert. (Ohanian points out that his appearance on “Late Night” in May, while “rad,” wasn’t the first time he’d met the host: Back in the day he went on “The Colbert Report,” an experience that he remembers being “the hardest interview I’ve ever done … they’re like, ‘Don’t try to be funny.’”)

Ohanian has always had a flair for the dramatic: In We Are the Nerds, a book published in October that details the rise, fall, and rise of Reddit—the title refers to something Ohanian once hollered in a fit of happiness at a mid-aughts party—Ohanian is referred to by a colleague as “Chief Bullhorn.” Cutler says that when it comes to the two Initialized founders, “Alexis likes to say that Alexis is the sizzle and Gary is the steak.” In a recent interview about personal finance, Ohanian sheepishly revealed that he used to bring elaborate flower bouquets to every first date. As it turned out, this unapologetic corniness turned out to be an asset when it came to Williams. The couple’s origin story is circuitous and cute, involving a cameo by Kristen Wiig and a poolside rat hoax, but hinges almost entirely on Ohanian’s bold decision to treat an offhanded “you should totally come see me play sometime” courtesy offer from Williams—“an L.A. invitation,” as he calls it — as a legit excuse to actually show up in Paris for the French Open.

Still, during this time, Ohanian managed to piss off many of the people around him. After returning to the increasingly mutinous Reddit as executive chairman in late 2014, Ohanian oversaw a troublesome time for the company. “The second act really helped me see what it would take,” he says, “to bring a company not from zero to one, but from one to 10.” When he unceremoniously fired Victoria Taylor, a popular community manager, in July 2015 it was bad enough. It was worse that Ellen Pao, the embattled interim CEO, shouldered much of the blame.

“It was my decision,” Ohanian later wrote in a Reddit comment. “And the transition was my failure and I hope we can keep moving forward from that lesson.” Sam Altman, the head of Y Combinator and a Reddit board member, answered questions from users the same day. “Free speech is great and terrible,” he wrote in response to one question. “I think figuring out how technology can encourage empathy is one of the more interesting and important open research problems in the world right now.”

Growing up in Maryland

Ohanian grew up in Columbia, Maryland, and long before he was watching his wife play tennis and naming his baby daughter after himself, he was watching the Washington Redskins and making plans to name a future baby after a different man. “Son or daughter,” he wrote in the acknowledgements of his 2013 book Without Their Permission, “I’m naming him or her Robert Griffin Ohanian.” When I remind him of this almost instantaneously dated reference and ask his thoughts on the current state of the franchise, he sounds legitimately aggrieved. “I don’t even want to talk about it,” he says. “I’m so over it.”

Once upon a time, Ohanian’s first big purchase upon selling Reddit was to upgrade his father’s longtime nosebleed tickets to four sweet seats near the 50-yard line. Now, annoyed at both the team and the league, they have let the ticket subscription lapse. “I was raised a diehard,” says Ohanian. “I would have never imagined after 25, 30 years of indoctrination, feeling this ambivalent about it, but I really do.” When the Redskins signed Mark Sanchez in mid-November, Ohanian weighed in: “Am I too late to make the obvious @Kaepernick7 tweet?” Growing up, Ohanian thought the coolest thing in the world would be to own a pro football team. “And now, actually, instead,” he says, “I just own an esports team.”

Over the years Ohanian and Initialized have been a part of some extremely successful investments, like the crypto trading platform Coinbase and the increasingly omnipresent Instacart. But Cloud9 might be the objectively coolest venture they’ve backed. Cloud9, which counts among its properties the Overwatch League champion London Spitfire, was named the year’s top esports organization by ESPN.com and was also figured by Forbes to be the most valuable player in the growing esports ecosystem, based in part on its youth-focused strategy and its successful merchandising arm.

Cloud9 isn’t the only Initialized portfolio company to have racked up big wins in 2018; there was also a major victory in San Francisco’s hectic scooter wars when Skip, a scooter-share business, was awarded one of just two contracts to operate in San Francisco. For much of 2018, the standard operating procedure among competing scooter companies had been, basically, just to show up and deal with the details later, that tried-and-true ask-forgiveness-not-permission startup model. The result was sidewalks littered with devices and swift action by city board of supervisors to pass a law requiring permits.

“Three companies — Bird, Lime and Spin — unloaded hundreds of motorized scooters across San Francisco,” wrote the city’s irritated Municipal Transportation Authority in its decision to grant permits to none of the three. “I looked at this with delight,” says Ohanian of his competitors’ failed attempts to move fast and break things. “For a product and a business that requires you to work with governments and communities, it just seemed so obviously self-destructive.”

Skip’s deliberately collegial approach, sitting down with city planners to draft policy and incorporating community feedback into their scooter design, wasn’t rogue or cool, but it got the job done.

As an early-stage venture capital investor, Ohanian loves to be the guy who swoops in to write the “first check” to the enterprising souls behind some compelling new startup. But earlier this year, when Ohanian agreed to liaise with one particularly passionate group, it wasn’t because he had visions of hockey stick growth or tangible return on investment dancing in his head. “Working with Alexis was really a big deal for a small little startup organization,” says Katie Bethell, the founder of a nonprofit called PL+US that is dedicated to fighting for paid family leave in the United States.

Bethell knew that getting a response from Ohanian, to whom she reached out via a friend who had once met him at a dinner, was a long shot. But she also knew that Ohanian was a proud new dad with interest in the subject of paid leave, and wanted to see whether the famous founder would participate in a speaking engagement about fatherhood and family. He said yes, and the two chatted on stage for more than an hour this summer in San Francisco. “The thing I was most excited about,” says Bethell, “was his willingness to call for up to a year of parental leave in the U.S. I think as a business leader, that’s really bold, and shows how much he is putting kids and family at the center of his analysis.”

Having seen firsthand how debilitating the aftermath of a delivery can be, Ohanian gets riled up when he discusses the subject. “The statistic that was most alarming,” he says, “was that one in four American women are back to work after two weeks from having a kid. And that seems—it’s unconscionable.” Ohanian has engaged in various forms of political activism in the past, though the issues were typically technology-based: In 2012 he protested the federal privacy bill SOPA, which would eventually die in the house, and in 2014 he lobbied for net neutrality. “He’s got credibility both in the private sector but also just, like, at a national scale in terms of advocacy,” Cutler says. And he plans to use it: “You’ll probably be seeing me in a suit in D.C. next year, making the case for [paid family leave],” Ohanian says. “I really do think there are folks on both sides of the aisle in office who want this.”

Importance of Mental Health

For much of the year, Ohanian has also been delivering an adjacent message about mental health, burnout, and perspective. In March, ruminating about the 10-year anniversary of his mother’s death from brain cancer and the depression he’d felt as a result, he wrote: “As entrepreneurs, we are all so busy ‘crushing it’ that physical health, let alone mental health, is an afterthought for most founders.” He further expanded on this idea in November, speaking at the Web Summit conference in Lisbon. “Hustle porn!” he yelled. “This is one of the most toxic, dangerous things in tech right now,” he said. “This idea that unless you are suffering, grinding, working every hour of every day, you’re not working hard enough.”

Humans trying to be robots: It’s an instinct Ohanian can certainly understand, which is why he knows how damaging it can be. Last week, when the 34-year-old founder of HQ Trivia was found dead of a suspected drug overdose, another young founder, The Athletic’s Alex Mather, fired off a bunch of tweets about the importance of self-care. “[I] want to talk about founders, failure, and mental health,” he began. “I’ve been so happy to see @alexisohanian talk about this at length.”

In February, Ohanian pulled off one of his characteristically grand gestures. With Williams returning to tennis at the tournament in Indian Wells in Southern California, Ohanian welcomed her back to the game by setting up four billboards along I-10 that featured pictures of Olympia and Williams along with the words, “GREATEST MOMMA OF ALL TIME.” It was a touching tribute, and also happened to be a great way for Ohanian to do his ongoing due diligence on an Initialized portfolio company called AdQuick. By using the product for himself, he was engaging in a practice that is known as “dogfooding.” (Classic Business Dad move!)

There’s a certain shameless beauty to much of Ohanian’s strat. Earlier this year, when he and his friend Jennifer 8. Lee led a petition for interracial relationship emoji, the effort was also spearheaded by Tinder. Around Father’s Day this summer, Ohanian made the rounds to talk about fatherhood and fitness in a media blitz sponsored by Johnnie Walker, which led to some casual, normal statements like, “When I see that first little outline of a six-pack, I’ll be raising a glass and toasting a little bit of Blue Label to celebrate.” Ohanian’s daughter, who is mostly known as Olympia, although he usually calls her “Junior,” has more than half a million followers on Instagram; the account for Olympia’s baby doll, Qai Qai, has amassed 60,000-plus since late August. “It’s kind of silly,” Ohanian says, “but even watching the way that people interact with our child’s doll, there are these moments of real humanity that I think people have been really hungry for this year.”

It can be hard to hear that and not cynically wonder about Ohanian’s motivations, or scoff at the idea of the Reddit cofounder waxing sentimental about humanity. It can be hard not to side-eye Ohanian when he gets into full “as a father of a daughter …” mode. Even the company Papa — sweet, pure, empathic Papa — exists not to make intergenerational friends, but to make money. (Insurance companies find the business compelling because, by reducing isolation and loneliness, Papa has positive health benefits. This sounds like a win-win until you envision a future in which some poor soul has a health care claim denied because she didn’t spend enough hours relaxing with a Papa Pal that month.) When I describe “hustle porn” to Bethell, she has a thought-provoking perspective. “I think working moms,” she says, “have been operating under the tyranny of hustle porn since the ’80s.” She paraphrases the writer Amy Westervelt, noting that women are expected to parent like they don’t work and to work like they don’t parent. And viewed that way, it’s possible that Business Dad is just what happens when hustle porn reaches middle age.

Still, Ohanian is someone who has real social and economic clout, and he generally wields it thoughtfully. (In the cutthroat world of startups and seed money and overnight millionaires, even just the appearance of propriety can feel welcome.) At Initialized, 40 percent of the investing partners are women, and one of the fund’s recent investments was in an organization called The Mom Project that helps lapsed employees reenter the workforce. Initialized recently set up a panel discussion about mental health for its employees. New mothers and fathers alike are encouraged to take their full 16 weeks of leave, as Ohanian did when his daughter was born.

Ohanian hasn’t seen his wife and daughter in person for days, but when I ask what’s new with Junior he describes, in great detail, a video he just watched of the toddler performing her latest silly baby trick: summiting her high chair, solo. “She’s got a good little kick where she can handle stairs,” he explains of the curly-haired girl. “She’ll kick that leg up over the side no problem,” he repeats, “but I’d never seen a full climb, because you’ve really got to go vertical. It’s not just kicking your leg over the side, it’s lifting your knees straight up ahead of you and climbing up that high chair.”

I recognize his tone: Like most parents, Ohanian speaks of his offspring’s escapades in a manner that falls somewhere between a coach evaluating a quarterback and a mechanic admiring a sweet rig. Maybe at some point a machine will learn how to replicate that exactly, but it hasn’t happened yet. For now, it feels like a uniquely human thing.