Pierre Omidyar has issues. Several problems, actually.

The billionaire technologist, philanthropist, and publisher is stitching together a strategy for his weeks-old First Look Media group, and he’s grappling with some essential questions:

  • What’s the focus?
  • Will First Look be one big brand, or a confederacy of brands?
  • Will it serve a mass audience, or a niche audience?
  • Will it be “problem-pointers,” or problem solvers?
  • Can its journalism innovation match its technology innovation?

First Look Media launched in February with The Intercept, featuring Glenn Greenwald, who, while working for The Guardian last year, was the first to report on the National Security Agency’s far-reaching surveillance program. Greenwald practices what he calls "adversary journalism."

The hiring of Greenwald has framed the public’s view of First Look. Many people, include journalists, thought that First Look was Glenn Greenwald.

In fact, The Intercept, which focuses specifically on national security and privacy issues at this point is just one of several digital magazines that Omidyar envisions. Another, run by Matt Taibbi, a former Rolling Stone reporter and National Magazine Award winner, will use in-depth reporting to untangle America’s largely impenetrable financial system.

Omidyar and his team will unveil others later. Right now, they also plan to publish more traditional verticals around subjects such as politics, entertainment and other topics yet undetermined.

You might think this would be easy work for the founder of eBay, who created Honolulu Civil Beat, an online publication in Hawaii where he lives, and who supports a host of journalism-related projects through his Omidyar Network and Democracy Fund. (The Democracy Fund has provided grants to The Poynter Institute.)

It’s not.

And so Omidyar gathered, at his expense, several of First Look’s top executives and about a dozen high-profile editors, journalism educators, industry analysts, and former reporters last Saturday in Laguna Beach, Calif., to listen to his vision, dissect his emerging strategy and offer advice on both.

The only catch: The day was governed by what is known as the Chatham House Rule, under which participants agreed not to quote from the proceedings directly.

We sat in a U-shaped formation in a ballroom at Omidyar’s elegant Montage Hotel. The group spent eight hours asking questions, challenging First Look’s brass (and each other), and generally seeking to understand the burdens and opportunities that come when a billionaire decides to push $250 million toward a journalism venture for which he has extraordinary expectations.

Throughout the day, Omidyar, serious and polite in an open-necked sky-blue dress shirt, dark slacks, and rimless glasses, scribbled observations in a black notebook and asked lots of his own questions.

What became clear is that the brilliant, unassuming Omidyar is wrestling with the same questions that presumably dog many technology companies that practice journalism these days. What follows is a sampling of some of those issues:

What’s the focus?
When resources aren’t a problem, it’s easy to try to be everything. Omidyar gets that. Still, he and his team haven’t yet figured out their focus. Do they want to follow the model they’ve already begun with and add other magazines focused on critically important but complex issues? Climate change, for example? And how are they going to pick which verticals to build? Focus on areas that are currently undercovered? Or pick areas with lots of coverage already, and just try to cover those subjects better? Say, sports?

Omidyar recognizes this as a crucial issue in part because First Look’s focus will impact a host of decisions – from hiring to branding. And, of course, just as crucially, its focus will determine not just what it does, but what it doesn’t do.

Will First Look be one big brand or a confederacy of brands?
Clearly, with the hiring of Greenwald and Taibbi, First Look plans to attract big names. The question is whether those brands will fit neatly under the First Look brand, or whether they’ll be a loosely connected group of journalists who all happen to earn their paycheck from the same billionaire.

It’s an important issue.

If First Look is the big brand, then it will hire people based on a clearly articulated vision and set of values. It will find fledgling stars and make them First Look stars. It will bring people in who will do things the First Look Way, whatever that turns out to be.

On the other hand, in an industry that’s increasingly obsessed with personalities, does First Look have a choice but to become a confederacy of brands? The benefits are clear: credibility, (particularly with the fans of those personalities), attention and influence that might take years to build without those stars.

And the risks?

What happens if the star’s persona is a controversial one, even if his journalism is stellar (see Greenwald)? At some point, does that persona become a distraction? What happens if the star’s fans, for whatever reason, abandon him as swiftly as they embraced him? And can any organization build a coherent, compelling brand if it’s just a collection of loosely associated stars?

Will First Look serve a mass audience or a niche audience?
Throughout the day, Omidyar and his First Look executives said they intend to serve a mass audience. They also said they plan to produce high-quality content that impacts users and engages them as both audience members and citizens.

What’s unclear is what they mean by a mass audience. And is there a mass market for high-quality, high-impact journalism?

Several participants expressed skepticism, at least quietly.

One answer may be that First Look does both – cultivates a highly educated, civically engaged audience even as it serves more popular, mid-brow content to a broader audience.

First Look may decide that its digital magazines should provide content for the former and that its more traditional verticals cater to the latter.

If that’s the case, will First Look dilute its ability to impact its audiences? And will that make it harder for First Look to craft a clear identity?

Will First Look be about “problem pointing” or problem solving?
Let’s start with the answer: Omidyar and his editors want First Look’s journalists to do both.

The question really is, how?

Glenn Greenwald is known for his passion and blade-sharp intellect, and for lacerating his opponents. He’s not famous for laying out solutions. He’s famous for breaking news – and for breaking china.

And no one has necessarily called upon him to do otherwise.

But Omidyar and his team aren’t interested in just breaking stories, or just “problem pointing,” as one participant called it. Nor are they interested in just fomenting controversy. They want to provoke intelligent discourse that gives their audiences options for actually solving the problems that Greenwald, Taibbi and other First Look stars surface with their reporting.

Which only leads to more questions for First Look’s leaders: How does this desire to solve problems influence how they hire their stars?

First Look is being constructed around personalities who combine deep expertise and a distinctive voice to drive engagement. Can First Look also depend on those same personalities to guide an audience toward solutions for some of America’s (and the world’s) most complex problems?

And what are the risks First Look faces if that it wants to do that? And what opportunities will go wasted if it decides not to?

Can First Look’s journalism innovation match its technology innovation?
First Look is a technology company that does journalism.

Its founder created eBay, a first-of-its-kind business.

When Omidyar discusses technological innovation, he does so with an ease and authority that bespeaks the depth of his knowledge and experience.

Omidyar is far less at ease with journalistic innovation.

He heard several participants on Saturday tell him and his team that journalists want to innovate, but they’re afraid of failure. Omidyar was unsettled by this. He has a technologist’s mindset, which is to say, he understands that innovation and failure go hand in hand.

Participants sought to calm his fears. They told him that journalists are eager for leadership that’ll support innovation not just with words but with action and resources (which presumably won’t be an issue at First Look). He heard the group tell him to provide financial incentives to his journalists who innovate, and to hold everyone in the organization responsible for innovation. They told him he’ll need to stress that innovation isn’t just about technology; it’s about solving problems – all kinds of problems -- in new ways.

Omidyar, ever serious, nodded and scratched more notes. At the end of the day, he appeared stimulated, if weary, after eight hours during which he inched toward a few answers, but no doubt walked away with even more questions than he had when the day began.