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Citizen Carlos

Anh-Minh Le | January 3, 2017 | Story Profiles

Carlos Watson and Laurene Powell Jobs are currently sharing the stage inside The Chapel, a San Francisco music and dining venue festooned with oversize snowflakes and bathed in red lighting. It’s mid-December and the longtime friends, who met about two decades ago while volunteering at Carlmont High in Belmont, are hosting a joint holiday party for their organizations: He is the CEO and cofounder of new-media business OZY, and she is the president and founder of the philanthropic Emerson Collective. Powell Jobs, the widow of Apple founder Steve Jobs, may be the more recognizable name, but on this crisp winter evening, Watson is exuding an equal amount of star power. The pair briefly takes turns congratulating each other’s teams for a job well done in 2016 before Watson, with his million-dollar smile on display, shouts to the crowd: “We’re gonna do great things in 2017!”

Watson’s charm is palpable, a trait that has undoubtedly factored into his rapid rise in Silicon Valley. His Mountain View–based company OZY, a digital magazine of sorts that is now expanding into television, has garnered $30 million from a mix of venture capitalists and angel investors that includes not only Powell Jobs, but legendary lawyer Larry Sonsini and Woodside’s GSV Capital. The latter—which has also invested in Twitter, Facebook, Dropbox and Spotify—participated in all three rounds of OZY’s funding. “Frankly, Carlos is the kind of person who you want to back in whatever he’s going to do,” says Michael Moe, GSV Capital’s chairman, CEO and chief investment officer. Like Powell Jobs, Moe has known Watson for years. But it was OZY’s unique position in the marketplace that most enticed him to invest. “Ozy’s really about what’s new and what’s next, done in a thoughtful, creative, high-caliber way,” he says.

Even if the coverage topics are what you might expect from a new-school digital publisher—a smattering of politics, culture, sports, tech and social issues—the OZY specialty is often more of a change-up than a fastball. “The Trade War That America Started—and Canada Won” looks at a tariff battle that started in the late 19th century. “Will Notre Dame Ever Land Its Dream Coach?” ponders the next move for the university’s struggling football program. “The Rise of the ‘White Guilt’ Book Club” examines liberals’ attempts to raise racial consciousness. “Iced Horchata Latte? Yes, Please” is an irreverent trend piece about Mexican-themed beverages. The regular “Rising Stars” profiles seek to highlight folks before they become household names (Simone Biles and Mike Pence were early examples). “While OZY does a good job of catching people up, we really want to vault you ahead every day,” Watson tells me in his office a few weeks before the holiday party. In talking about his company, he invokes some of the same descriptors as Moe. “We think that our curious, creative audience loves to discover the new and the next. And that might mean new people, new trends, new ideas. The stories have flavor; they’ve got sabor. Life’s too short. Who wants anything that’s kind of boring?”

In addition to a daily roundup of news that readers can receive in their inbox, OZY, which turned 3 last fall, delivers eight original features every day. The site attracts 20 million monthly unique visitors. “OZY’s geared toward what we call the ‘Change Generation,’ by which we mean the curious,” says Watson. “Some people assume that’s one and the same with millennials—and, sure, it includes them. Our audience is disproportionately millennials, but Bill Gates says we’re one of the two things he reads every day. And he’s not a millennial.” (Gates, along with another famous Bill—Clinton—has contributed content to the site.)

Although Watson declines to give financial figures, he says that OZY has been profitable since somewhere between its second and third years in business. Revenue is derived from three channels: advertising, including accounts with Rosetta Stone, Netflix and Volvo; live events such as its OZY Fusion Fest that debuted last year and featured a diverse lineup ranging from author Malcolm Gladwell and political consultant Karl Rove to musician and chef Alex Guarnaschelli; and, most recently, television partnerships. As part of a multimillion-dollar deal, OZY’s first TV series, The Contenders: 16 for ’16 , began airing on PBS last September. Each of its hourlong episodes compared two presidential candidates, spotlighting their differences and similarities. More programming is in the works, and OZY has signed on with Hollywood entertainment powerhouse Creative Artists Agency.

Moe credits Watson with assembling OZY’s impressive, and ever-growing, list of partnerships. “With young businesses, there’s just no way all of this happens—unless you have Carlos having the belief that they need to be part of it,” says Moe. “He’s got a compelling personal story. He’s got a compelling personality. He works like nobody I’ve ever seen. And I think that force of nature, combined with his vision, is creating something that’s extremely exciting.”

Watson shares more
than just a name with his father, Carlos Watson Sr. At an early age, the two bonded over their love of the news. “My dad was raised in a small little countryside village in Jamaica, where they would listen to the news on the radio,” says Watson. “And he used to say that listening to the news was the only thing that gave him hope that his life was going to be different. Because he could hear other people’s lives, and he could hear other people doing things. So he didn’t have to think: The only thing I can do is what I’m seeing in this little village of a couple hundred people. He didn’t just have an intellectual relationship to the news; he had an emotional—an aspirational—relationship.” (His dad later immigrated to the United States and studied at Ohio State University.)

Carlos Watson Jr. is the second of four children, the only boy in the family. He comes from a long line of educators, including both of his parents. His father taught sociology, mainly at the university level, while his mother, Rose, was primarily an English teacher. Growing up in the working-class Miami neighborhood of Homestead, Watson started volunteering in the local schools and initially dabbled in journalism as a teenager, penning the Watson’s Wide World of Sports column for his high school newspaper. While earning a degree in government from Harvard University, he devoted his summers to interning at The Miami Herald and Detroit Free Press. “The Miami Herald is what we always read,” says Watson, recounting his first published article—a front-page article, no less—for his hometown paper. “So you can imagine how proud my dad was to see my name [in print]. I don’t know how many newspapers he bought that day at the 7-Eleven, but he bought a lot of them!”

After college, Watson spent a year entrenched in politics, serving as a campaign manager and chief of staff for Florida Rep. Daryl Jones before enrolling at Stanford Law School. “While I was in law school, out here in the Valley,” Watson recalls, “I started thinking about business more than I had before.” Despite summer stints with prestigious firms such as Wilson Sonsini, upon earning his J.D., Watson headed to McKinsey & Company for two years. Then, in 1996, he decided it was time to scratch that entrepreneurial itch: Achieva was borne out of his volunteering days. “I realized that most schools didn’t have a lot of counselors, but they had thousands of kids,” he explains. “We built software, books and workshops that big cities could use to help students prepare for and apply to college.” According to Watson, Achieva worked with 100 school districts, in half the states in the United States. In 2002, he sold the company to The Washington Post Co., and Achieva has since merged with Kaplan.

Watson next spent six months traveling, mostly in Asia. Then the TV news world came knocking. It started with guest appearances as a political analyst. He was especially sought-after during the 2004 election. “Most people offering commentary were conventional-wisdom types,” he observes. Watson was young, intelligent, articulate and charismatic—precisely what the networks were looking for. He hosted an interview show for CNBC. He then joined CNN as a regular contributor. Eventually, Watson anchored a one-hour MSNBC program called Live with Carlos Watson. Along the way, he won an Emmy and was named to Peoples “Hottest Bachelors” list. (He’s unmarried, but does have a girlfriend.)

Professionally, Watson was thriving in New York. But about six years ago, his personal life suffered a major blow—one that would ultimately lead to the founding of OZY. “The full truth is, unfortunately, my mom got really sick,” he says. For the first time during our conversation, that wide smile disappears. His mother, he tells me, was diagnosed with late-stage kidney cancer and unable to live on her own. So, with his mother residing in Mountain View, Watson returned to the Bay Area in 2012. “I had never had someone I was that close to get sick,” he says. “And I don’t mean to sound hokey, but I really started to think hard about what I wanted to do, and what mattered, and I kept coming back to the thoughts that I had had around building a new kind of news source—something that might make people see the world differently.”

And that something was OZY. “What was out there was OK, but not great,” says Watson of the media landscape. “There was a chance for someone to build the Apple, the HBO, the Tesla of this space—by which I mean something that’s smart and colorful and breaks from the norm in an important way.” He officially launched OZY in 2013. A year later, Rose Thomas Watson—who, ever the educator, was a driving force behind the company’s internship program—passed away.

In Watson’s office hangs a large framed portrait of his mother, and her vision for the enterprise he co-founded continues to propel him. “A big thing for her was that OZY have a desire to be transformative,” says Watson. “Some news is just news. It’s just information. It’s just a ticker. But I think because she was a teacher, because she came from a place where she believed that people could learn and grow and develop, that that mattered. She wanted OZY to be catalytic in that way—to be substantive and open people’s eyes.”

In late November,
when Watson and I meet at OZY’s headquarters, the national press is still reeling from Donald Trump’s presidential victory, and a newly released 60 Minutes/Vanity Fair poll found that the media is the least trustworthy industry in America. Yet the mood at OZY is upbeat, as Watson proclaims that the post-election backlash is an opportunity for his startup. “A couple of things came out of the last month,” he says. “People realized that living in the echo chamber is a problem. And people realized that those who report too scientifically are worth listening to, but not worth listening to only.”

In other words, it’s time for different voices, like OZY’s, to be heard. Jeremy Rue, a lecturer of new media at the UC Berkeley Graduate School of Journalism, sees some truth in this sentiment—as well as a correlation between the ballot results and the state of the news media. “That’s sort of what the election was really about—a bending of the establishment and bringing a fresh perspective,” he says, noting that the traditional news background of the “OZY Tribe”—as the employees have dubbed themselves—bodes well for the company. “My hope is that people bring with them some of the core values of what journalism should be,” Rue adds.

Indeed, Watson considers the crux of OZY’s success to be its team—a combination of full-time staffers and an army of freelancers worldwide. “We interviewed over 750 people to hire our first 50 people,” he says. The second employee that Watson and co-founder Samir Rao brought on board was Stanford alum Eugene S. Robinson. An editor-at-large at OZY, Robinson previously worked for a number of magazines, including as editor-in-chief of Code and EQ. He was immediately struck by the fact that Watson “wasn’t interested in chasing the news,” says Robinson. “Because we’ll never be able to compete. You have what, over a hundred articles on So we’re going to distill it down to eight pieces, and they can’t be superobvious pieces.” And while OZY’s staff is encouraged to write about matters that are of genuine interest to them, “you still have to make a passionate case. You still have to go into a meeting and explain why we should do a piece on Mafia dump sites, why it’s useful.” (And, yes, he did cover that topic in a video series.)

Although a digital operation, OZY has an editorial process for in-depth features that is akin to a traditional magazine’s—with typical lead times of a month or two, says its deputy editor, Pooja Bhatia (like Watson, she has a law degree; hers is from Harvard). Prior to joining OZY, she spent several years as a foreign correspondent in Haiti. Cameo George, the deputy editor for video, came over from CNN and is an Emmy Award–winning producer. “Our belief in hiring the most talented people all around the world, being really global, is going to stay strong,” Watson says. “Our belief in not just focusing on what’s in front of your nose, but looking down the field, is only going to get stronger. And our belief in doing that in red states and blue states and purple states—and non-U.S. states—is really strong.”

In response to the election, OZY is embarking on a bus tour in early 2017 that will initially take its reporters through swing states such as Wisconsin, Pennsylvania, Michigan, New Hampshire, Nevada and Florida. The goal is to present varying perspectives. “The last thing we need is people telling the same stories over and over again,” says Watson. “We need to be able to see broadly and creatively. We need to be able to expect the unexpected. In this environment, people are going to want really thoughtful publications.”

Watson’s ambition is to build a business that endures, beyond his lifetime. On a trip to New York, after learning that Times Square is named after The New York Times, his eyes lit up as he envisioned an OZY Square in Mountain View. Aside from OZY, the Silicon Valley city he now calls home may be the thing he’s most effusive about. He is a regular at Xanh, a modern Vietnamese restaurant downtown. And the Le Boulanger on Castro Street, a short walk from OZY’s office, is where he conducts meetings and interviews of all kinds—including a portion of ours. “Samir and I started in a couple of chairs over there,” he says, pointing toward the front of the eatery that he simply refers to as “L.B.” Perhaps someday—like that garage where fellow Mountain View company Google began—this unassuming spot will become more widely known as the birthplace of OZY, the new-media platform that strives to, as Watson puts it, “make you a little smarter, a little sooner.”

Originally published in the January issue of Silicon Valley

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