A Conversation with Kentucky Confidential

By Dana Byerly

In a year where there is still so much uncertainty surrounding the Kentucky Derby contenders, one thing is certain about Kentucky Derby 137: there will be a LOT of media coverage. But this hasn’t stopped our founder, Jessica Chapel, from starting an intriguing new project called Kentucky Confidential.

The Kentucky Derby is one of the most heavily covered events in American sports, but rare is the outlet that treats it as a storytellers’ paradise.

That’s how we plan to cover the Derby.

The site, which is free for visitors, will be launching on April 26 and offer a broad spectrum content. Not only is Jessica collaborating with some of the most interesting turf writers, filmmakers and photographers, she’s taking an unusual approach to funding. Using a platform called Kickstarter, which allows independent projects to more easily get funding, Kentucky Confidential hopes to underwrite their ambitious project. Part of the incentive for backers, in addition to supporting a project they believe in, are rewards and Kentucky Confidential has lined-up some pretty enticing ones!

We asked Jessica to share a bit about what visitors can expect from the site and the decision to go with Kickstarer, here’s what she had to say.

R360: Congratulations on your exciting new project! You’ve lined up some excellent talent to bring racing fans a view of the Derby that we all want to see more of, the storytelling aspect. Without revealing any of your plans (too much!), can you talk about some of the approaches or storylines that readers might find at your site?

Jessica Chapel: We’ve drawn a great bunch of contributors. Everyone involved has a distinctive style or voice. While we have an idea of what we want the site to be, and we’ve assigned a few pieces, for the most part we’re letting contributors focus on the kind of stories they want to tell. There’s no lack of material at Churchill — John Scheinman called the Derby “the greatest storytelling platform in American sports,” a description I just love — what we felt was missing was the space for more original or reflective work.

I’m very interested to see what our videographer, the filmmaker Jeff Krulik, comes up with. If anyone can tap into the same Derby vibe as Hunter S. Thompson did years ago, I suspect it’s him.

John Scheinman, who’s collaborating on the project with me, will be handicapping (and writing about handicapping) the Derby and the undercard. Stats are a big part of breaking down the race — I don’t want to give away too much yet, but we’ll be publishing some really in-depth work into things like jockeys’ riding styles and trip analysis. Claire Novak will be doing profiles and historical features — I’m already looking forward to one about a forgotten figure from the 1930s — and we have Pete Denk for contender updates. We’re bringing “Blinkers Off” along — our anonymous correspondent will be filing humorous, chatty reports from the backstretch — and we plan to run a Louisville nightlife column called Bourbon Underworld written by Brendan O’Meara.

A big part of the site will be its photography — in addition to the usual shots of contenders and connections, we plan to publish more candid and unexpected pictures, photos that really bring the Derby scene alive and up close.

R360: Very exciting! No doubt creating content of this caliber takes money and I can speak from experience that advertisers are leery about backing if your product isn’t out there yet. Can you talk a little bit about your decision to use Kickstarter?

Jessica Chapel: You’re not kidding about advertisers being leery of a backing a new venture, with all the unknowns in play. Will the site get enough traffic? Will it draw the right sort of audience? We made it even tougher for potential advertisers, because Kentucky Confidential will only be active for two weeks. That didn’t scare away everyone we talked to — the Breeders’ Cup Betting Challenge is a charter sponsor — but it did quickly end a few conversations.

I’ve been trying to think of something for Kickstarter since a project using the platform called Art Space Tokyo made an impression last year. Crowd-funding is a really intriguing idea — that you can take a product or performance directly to its audience and make a connection from the start seems to have so much potential, especially for people working in the arts or media. I like that the model gives backers a risk-free stake in a project’s success.

Our limited run is what made me think Kentucky Confidential would be a good fit for Kickstarter. It’s an independent project, and a very defined project — not the content so much, because we’re giving contributors a fair amount of latitude — but in time and purpose. With its storytelling approach, the site’s something of an experiment in publishing. We’re trying to create something lasting out of an event that is so anticipated, so hyped, and then is over in mere minutes. For backers, I hope that means we’re a two-week pleasure to visit, and hopefully as memorable as whoever wins the Derby.

R360: I love Kickstarter and have backed several projects, including Kentucky Confidential! I have to admit that part of the fun of backing projects are the rewards. In addition to supporting an independent project, what incentives have you lined-up for potential backers? For example, what can backers expect from the subscriber-only Twitter feed, the commemorative DVD or the commemorative print magazine?

Jessica Chapel: The subscriber-only Twitter feed will include humorous overheard comments and candid photos. It’ll be a little taste of “Blinkers Off,” especially during training hours, as well as a forum for followers to give us feedback on coverage and make requests. We won’t be chasing breaking news, but if some comes along, the Twitter feed is where we’ll post it.

Jeff Krulik will be producing the DVD, which will include the Derby diary video he’ll be uploading through the week and additional footage. With the print edition, we’ll cull the best of what appears online during our two-week run and publish it as a handsome, full-color memento of the 2011 Derby.

Best of luck to Jessica, John Scheinman and all of the Kentucky Confidential crew! If you’re interested in backing Kentucky Confidential, or just seeing what Kickstarter is all about, check out their project page.