Inside billionaire Joe Ricketts' dreams of media empire

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Joe Ricketts. (Courtesy Chicago Cubs.)
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Joe Ricketts, the Nebraska-born mogul, fiscally conservative political donor and founder of the online brokerage titan TD Ameritrade, spent much of his life on the plains, where everything is flat.

So when he decided in 2006, at the age of 65, to get a pièd-a-terre in Manhattan, Ricketts went for altitude, buying a condo on the 78th floor of the Times Warner Center's north tower for $29.2 million.

It was there, one night in December of 2009, that he hosted an intimate holiday party attended by the staff of DNAinfo.com, the curiously named neighborhood news website Ricketts bankrolls.

Some guests were surprised by the feel of the apartment. It lacked the overweening worldliness you might expect from a billionaire's pad 750 feet over Central Park. The warm wooden furniture and touches of Americana evoked an almost countrified homeyness resonant of Ricketts' Midwestern roots—perhaps a nod here or there to the style of his primary residence in Little Jackson Hole, Wyo. But the understated decor was offset by sweeping views of the starry Manhattan skyline.

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The party itself wasn’t an overly sophisticated affair, either, although there were plenty of drinks and hors d'oeuvres, including bison sliders, courtesy of High Plains Bison, another one of Ricketts’ entrepreneurial pursuits. (Ricketts would add a chocolate fondue fountain to the following year’s holiday bash.)

That night, DNAinfo’s journalists were getting an early taste of the paradox of Joe Ricketts in New York: Ambitious and adventurous as any of the city’s plutocrats, but without any concern for social cachet. Friendly chatter revealed a man with a grandfatherly mien, prone to talk about business and finance but also about the historical movies on his Netflix queue, or his frequent travels, which in recent years have included a cross-country motorcycle trip through Canada and a fly-fishing expedition in Chile. It’s a life full of the good things, but without any real gestures toward glamor.

Halfway through the evening, Ricketts’ few dozen guests gathered around him as he said a few words about his pride at the launch of the site. Sree Sreenivasan, then a dean at Columbia’s journalism school whom Ricketts had hired to help get DNAinfo off the ground, stepped forward with a token of appreciation.

In the Nov. 16 issue of New York, just a week after the site went live, “Hyperlocal-news provider DNAinfo.com” was featured in the magazine’s “Approval Matrix” graphic. It was sandwiched, roughly, between the latest album from Canadian hardcore band Fucked Up and Kate Winslet’s libel payout from the Daily Mail, in the lower left-hand corner of the quadrant that was the intersection of "brilliant" and "highbrow" (as opposed to "despicable" and "lowbrow"). Sreenivasan had gone to Jack’s Art Gallery on 111th and Broadway to have the page framed.

“If you’re in this quadrant after one week,” he recalled joking to Ricketts as he handed him the gift, “the only way you can go is in the other direction. But we’re going to do our best to stay up there.”

THE CONCEITS OF THE APPROVAL MATRIX AREN'T A PERFECT container for what DNAinfo has become in the nearly three years since it launched. Its editorial program is perhaps best described as neighborhood-centric local newspaper fare of a type that has never really been achievable by the citywide dailies in a place as big as New York City, even when they parachute into Flatbush or Woodside or Inwood for a slice-of-life moment. The coverage is exhaustive, reliable and fast—as likely to focus on the local debate over a sidewalk-cafe license on the Upper West Side as a shooting in Williamsburg.

“Check your parks/playgrounds and see whether the sprinklers are on,” wrote Billy Gorta, a senior editor who came to DNAinfo from the New York Post, in an email to staff on June 20. “Need outraged parents if they're off or pics of happy kids if they're on.”

The site’s initial strategy of placing reporters in just about every neighborhood on the island of Manhattan was accompanied by significant hires in strategic citywide beats with neighborhood implications. The reporter for Washington Heights can't spend all day in a lower Manhattan courthouse following a murder trial that has rocked his readers; and anyway, there are likely Washington Heights stories locked up in administration buildings all over lower Manhattan that require dedicated journalists to cover them. So with reporters assigned to the courts, the NYPD, City Hall and general breaking news, DNAinfo competes on an almost level playing field with the city dailies.

At the same time, the site has managed to evade the death spiral that's made the media industry such a lugubrious habitat in recent years, without availing itself of very much of the newspeak that surrounds the hyperlocal news movement. Rather, its editors speak the language of the traditional newspaper newsroom, and many of its recruits come from traditional journalism backgrounds. It's not an aggregator, it's not a viral-video machine, it's not a platform. It is, pure and simple, a local digital newspaper.

And it’s thriving, by all outward appearances. The newsroom headcount, including a growing collection of seasoned editors and reporters poached from the local tabloids, has more than tripled since launch. Earlier this year, coverage was extended to all five boroughs, and the site’s competitors have been in a sweat ever since DNAinfo entered the race with its frequent scoops and more nimble approach to breaking-news.

But the part of the operation about which Ricketts must be most excited is the list of advertisers—some 150 in the first quarter of 2012—who are paying to reach the more than one million users that DNAinfo says visit its website each month on average. (The site logged 597,000 unique visitors in June, up 21 percent from 493,000 a year earlier, according to the digital measurement firm comScore, which tends to skew lower than internal metrics.)

“Everybody is trying to figure out how to make money with information on the web,” Ricketts says in a short video about the site. (A spokeswoman for Ricketts said he was not available to be interviewed for this article.)

“Local news, community news, neighborhood news, is the perfect place for the neighborhood business to advertise. I don’t know of any other method of advertising for local merchants that would be so effective as we are.”

Developed amid the wreckage of the 2008 financial crash, DNAinfo was an experiment in counterintuitiveness. It entered the world at a time when even the mightiest media empires were being forced to rein in costs. In New York, McKinsey consultants were roaming the halls of Conde Nast, their eyes fixed on every redundant editorial assistant or complimentary bottle of Orangina. Around the corner at The New York Times, once impervious to the types of economic vagaries that could easily have sunk a less sturdy ship, dozens of journalists were tossed overboard as the paper weathered a precipitous advertising slump that persists to this day. For many smaller news outlets across the country that were hemorrhaging revenue as the recession cut into their budgets, the only thing to do was pray for the bleeding to stop.

There were some signs of life in the deepening bench of digital start-ups proliferating at the time. But most of these weren’t particularly interested in paying for high-quality original reporting. Instead, aggregation had come into vogue thanks to titles like The Huffington Post, Business Insider and Newser. They seemed to foreshadow a future in which all online journalism might take the form of search-maximized bite-size re-blogs.

Given this climate, to sink millions of dollars into a venture like DNAinfo seemed downright defiant.

“Joe had this idea that when things are bad, you push into the wind,” said Sreenivasan.

Now Ricketts is doubling down on his unlikely gamble: DNAinfo will soon debut in Chicago, creating the New York flagship’s first sister title, and marking the start of an expansion effort that could ultimately import the brand to cities across the United States. (The original is now officially called DNAinfo New York.) A handful of journalists have already been recruited, including veterans of The Chicago Tribune, the Chicago Sun-Times, and The Huffington Post, and the site is expected to launch sometime this fall. It’s a sign, according to the people running the place, that the ink won’t be red for much longer.

“If we keep going on the path that we’re on right now,” said Leela De Kretser, DNAinfo’s editorial director, “we’re pretty confident about being nicely profitable.”