By Susan Lahey
Special Contributor to Silicon Hills News

Nicholas White, CEO of The Daily DotOne of the first stories that ran in The Daily Dot: The Hometown Newspaper of the World Wide Web, was an obituary.

Most obituaries for Angelica Marie Schaaf Rayl talked about her as a wife, a mother, even a soap maker. The Daily Dot focused on her founding Etsy Bitch, a forum for artists and craftspeople who sell their work on the Etsy website. Schaaf Rayl had built an online community of more than 500 people who were passionate—not always in a good way—about Etsy.

That’s what The Daily Dot does.

The new, online, Austin-based paper covers the web like a city full of unique communities whose citizens are intensely engaged with each other. Cities have school districts, development corridors and business communities; the web has Etsy, Facebook, Reddit and World of Warcraft. The Daily Dot covers politics, entertainment, culture and business, like other newspapers. But its focus is exclusively on how these play out online. The fact that the Internet address was for sale might be a blurb in some papers; but it’s big news in The Daily Dot. A kid who garnered worldwide support from a YouTube video about being bullied was doubly covered by the Dot when he followed that up with a smug video about not really needing peoples’ support. He had played fast and loose with the global community.

It’s written in internet speak, with no apologies for terms like “twee” which, according to the urban dictionary, means excessively sweet. No explanation of ‘spambots’ or ‘uniques. ‘

The Daily Dot is led by CEO Nicholas White, an idealistic, poster child for a liberal arts education. The product of six generations of journalists from a family that now owns 10 newspapers and 12 radio stations, White naturally was committed to do anything but journalism. He studied film, earned a master’s degree in American Studies and recently completed his master’s in positive psychology. He also has two certifications in film, and for awhile that was his career of choice. He studied at Haverford College in Pennsylvania, where he met Joshua Jones-Dilworth, Daily Dot cofounder, who was studying English and philosophy. The pair created Eighty-Watt Theater, a student theater company “dedicated to pushing the bounds of common perceptions about theater.” That turned into Eighty-Watt Cinema where the pair, with other partners, made films to wake people up.

But one day, while on the elliptical machine–“This was all very symbolic” White said—he was struck with a serious doubt.

“I was wondering if it was possible that no matter how much the movies I make are a wake-up call, I am still supporting something, an industry and a culture, that does the opposite.” He’s not sure he thinks that anymore, but it was enough to send him back to his roots, to become a reporter at a family-owned paper, the Norwalk Reflector in Norwalk, Ohio.

He fell in love with journalism, especially the newsroom banter about heroes, villains and the bizarre cast of characters that comprise the newsmaking body of a community, including the amusing behavior of business moguls and favor-currying politicians.

What he didn’t like was the fact that very little of that extremely colorful comedy/drama ever made it to the pages of the paper. He didn’t like the mentality of many journalists that the paper’s job was to publish what people needed to know and turned a blind eye, in some ways, to what people wanted to read about. He thought the industry should change to woo readers back.

He also didn’t like how reluctant newspaper folk were to embrace the internet. Because he pushed his paper to enter the 21st century, he was given the honor to drag it there. He taught himself to program and created interactive media programs first for his paper, and eventually for the whole chain. By the time he left, he held the title of Vice President of Audience Development in the Midwest Division.

Where many newspaper people saw the internet as the usurper of advertising dollars, White saw it as an invitation to evolve. Instead of expecting readers to stick around because it’s the right thing to do, it was the job of newspapers to attract customers and advertisers.

“There was just so much opportunity to do cool, interesting stuff….”

The idea for the Daily Dot, though, came from a different direction.

Nova Spivak was a serial entrepreneur and friends with White’s partner-in-film, Joshua Jones-Dilworth. When White went into journalism, Jones-Dilworth went into marketing. In addition to his role on the Daily Dot, he runs a public relations firm that specializes in working with startups. It was Spivak who had the idea, Jones-Dilworth liked it and soon they hit upon the person who would be ideal to run it: Nick White.

They tossed it around for awhile, played with business plans, and soon learned that nobody wants to invest in content. Investors, White pointed out, holding his hands around an imaginary object, want a “thing. ” And they want to know they’ll get their money back. True, Huffington Post just sold for $315 million. But that’s the exception for a content business. Moreover, the founders of The Daily Dot have no plans to sell it. No easy exit plan that helps investors see the payoff.

So instead they did an F Round of financing, meaning friends and family. And about $600,000 later, in August of 2011, The Daily Dot was born.

The Daily Dot lists about 10 communities it covers, including blogs as one community. The company sells banner ads through Federated Media and Martini and lists ad rates of $18 to $40 per thousand impressions. The minimum monthly is $500. The paper had 170,000 unique visitors as of December 9.

Now, White said, he thinks they have a “thing” investors can see as an opportunity. So they’re getting ready to seek financing.

From an editorial perspective, The Daily Dot is still forming. Its founders want it to be the small town newspaper for the web and they talk a lot about old school journalistic standards. But it’s not intuitive, covering this kind of community.

“At first,” said Owen Thomas, founding editor, “we thought we’d have one reporter for Facebook, one for Twitter….. But then you take something like politics, now we’re more interested in how a political community is across these networks. That’s our challenge.”

Daily Dot reader Jason Stoddard thinks it might be too much of a challenge to overcome.

“Any time you try to organize and formalize any kind of a union, because of so many hard preferences, fragmentation is inevitable,” said Stoddard, entrepreneur and founder of Stagira Marketing. The internet is one such union with too many people having hard preferences to be united.
“What a local newspaper is supposed to do is be the hub voice, the central voice of a culture,” Stoddard said. “They say the internet is the last free market on earth, but it’s not really on earth….it’s very difficult to hedge the niche.”
Too much of the paper’s coverage, he believes, is fluffy. It covers the viral blog, but not the back story of the blogger. “It seems a little too glib, almost an apology because they don’t’ want to take themselves too seriously. You can’t go halfway on it. If you’re going to put a stake in the ground, put it in the ground.”

He quoted Arthur Hays Sulzburger: “Obviously, a man’s judgment cannot be better than the information on which he has based it….” The information in a daily paper informs people’s judgments and decisions. The Daily Dot operates in the culture of “Likes” which lends itself to popular information more than valuable information. That makes it too shallow to inform good judgments, Stoddard said.

White has great visions for the social impact of the Daily Dot. He wants the paper to provide a venue for discussing the global issues that the world can’t address without a compassionate dialogue. He paraphrased Karen Armstrong of the Compassion Project saying compassion begins when you’ve put yourself in the other person’s shoes so much that you can say “I can understand saying that” about something you ordinarily would hotly dispute. And The Daily Dot promotes a lot of internet communities’ altruistic side. Various communities raise vast amounts of money for causes both public and private and the paper covers those efforts regularly. But the paper also wants to be “The alternative to Fox News. ” And in the vast compassionate conversation, it seems unlikely Daily Dot staffers can see themselves saying something like “Vote for Perry.” Readers who are not hip, liberal internerds may not feel the love.

David Matthews does, though. A self-proclaimed “startup guy” who is currently working on a startup called Sponsorfied, he’s an active member of the Reddit community. But if he misses a few days, he doesn’t feel lost now, he said, because Digital Dot will be on top of it.

“That’s the value for me,” Matthew said, “they give me a summary of all the things that are going on.”

The Daily Dot’s plan? To become THE Internet newspaper.

“It’s a dauntingly crazy ambition,” acknowledges Executive Editor Owen. “But what other kind of ambition is worth having?”

(White wrote this blog post for PBS Mediashift on 5 Lessons Learned Building The Daily Dot.)