When the would-be sports site The Classical exploded into the Internet’s consciousness via Kickstarter last week there were, as much as there could be, cries of joy. For writers, journalists, and sports fans of a certain persuasion, it was like learning all your favorite musicians were getting together in a new band. It was The Raconteurs, or Damn Yankees, except with the likes of Tom Scharpling, Eric Nusbaum, David Roth, Lang Whitaker, Pete Beatty, and Bethlehem Shoals on lead guitar.

The Classical is marketing itself as a daily web publication and “a running, wide-ranging conversation between us and our readers about baseball, basketball, soccer, football and fighting, and about things that aren’t sports, too.” The pitch, or Kickstart in this case, is $50,000 to fund the site for a year. As fantastic as this all sounds, and since we’re in the business of the business of news, there’s still a big question to be asked: How is this thing going to work?

They’re aiming for something like The Awl, both in spirit and business model. That’s a noble goal, and perhaps smart since by most accounts The Awl is doing just fine. When I spoke to Shoals, he said they’re being purposefully ambitious but pennywise, since $50K, while a lot of money by Kickstarter standards, is not a large budget to start up a new business. “What is it — you spend money to make money,” Shoals said. “We’re asking for money to make money.”

That money buys time, to figure out a business plan, develop an audience, and try to make good on the big bet they’re asking readers to make. Since The Classical currently only exists in Kickstarter (and Twitter) form, they’re staking the future of the enterprise on their reputations, like saying if you liked us in X (say, on the pages of FreeDarko, where many Classical folks contributed), you’re gonna love The Classical. “We know it’s ridiculous for us to throw out a bunch of names and ask for money,” Shoals said. “But we hope the cumulative affect of our track record speaks for themselves,” he said. Which is why The Awl is such a good example, not just in the voice and variation in the writing (and writers). “I think what we all like about The Awl so much is that, from the beginning, Choire [Sicha] and [Alex] Balk said, ‘It’s not going to be stupid — we have good taste about what makes worthwhile content,” Shoals said. And both Sicha and Balk had established themselves with readers pre-Awl with stints at Gawker and elsewhere.

Another appealing element of the Awl model is its editorial independence. They want the ability, Shoals said, to do whatever they and the audience likes. “The thing about Kickstarter we like is it basically guarantees our independence,” he said. But another reason Kickstarter may be good in this case is as a proof: It sends a message (to potential advertisers, to other writers) that there are people out there to support what you’re doing.

For that $50,000, they’ll be running a tight ship, with that money splitting between the costs of setting up and running the site and payments to a couple of editors and to writers. They have a business person and a shadow publisher (who hasn’t been publicly ID’ed yet) guiding the early development of the site. “If you look at the names on the list, you can’t reasonably expect to have a legitimate web publication with those people writing regularly with no money coming from anywhere,” Shoals said.

That doesn’t mean fat checks for writers — $50K only goes so far — nor does it exclude the possibility of people writing for free. They’re planning to use a portion of that first-year budget in hopes of landing some big-name guest writers if possible. But writing for free, as Shoals and many others on The Classical’s roster know, is part of the new reality when it comes to online publishing. You do it for fun, for friends, for recognition, and for the idea that it could lead to taking that next step or next job. It’s a freelancer’s hustle: Give enough to get your due, but make sure the checks still come in. “The myth of the free internet is dogging us in the worst way possible,” he said. “Yeah, you can always do stuff for free, but it won’t be as good as possible.”

In order to do the things they want with the site, Shoals said they have to think like a business. Part of their first year (if they get the funding) would be committed to audience development and studying metrics — finding out the relevant data to take to market. Then they’ll begin to take on advertisers and, hopefully, have a better idea of the true cost of operating the site. It’s a business plan that might have seemed bizarre a few years ago, but it’s almost neotraditional by now: The startup money comes from the audience instead of investors with big checks. Which is why it’s so necessary to try and connect with an audience and give them reason to show a little faith. “It really is about being able to suggest to people that there is a light at the end of the tunnel somewhere,” he said. “That you have an audience and this might be something that will eventually lead to money.”

All of this may sound funny coming from a guy who ran a beloved blog that was long on great writing, but short on a readily identifiable business model. Of course, over its lifetime FreeDarko published two books, not to mention scads of fun merch (much of it designed by Jacob Weinstein, who created The Classical’s logo). Shoals said FreeDarko was an experience that offered plenty of lessons in both writing and the business of writing. Finding people to write because they love a blog — easy. Finding people to write consistently (and for free) — tougher. That experiences helped create the incentive to to nail all the little details of getting The Classical off the ground.

“Basically, FreeDarko taught me if you’re going to try and have something that is more than just a blog, you do need to have stability, structure, and commitment,” he said. “It takes money to do that.”