Company: Draft Sharks
Launch date: June 1999
Became full-time operation: 2000
No. of employees: 4

Back before he co-founded the World Championship of Fantasy Football, Lenny Pappano launched his fantasy football content site, DraftSharks.com. Although much has changed throughout the fantasy industry since then and free content abounds, Draft Sharks has stuck to what it set out to do: direct its unique brand of fantasy football insight to a smallish, loyal set of paid subscribers. Pappano recently took the time to answer some questions for FSB.com.

1. What led you to create Draft Sharks back in 1999? Why did you settle on that name for your site?

At the time, I was working as a copywriter at a political fundraising firm in the D.C.-area (part of the vast right-wing conspiracy). It struck me that a lot of the fantasy sites that existed were being run by tech geeks and not by anyone who could write well or had any background in journalism. I convinced my wife to drain our bank account to build a site and put some ads in a couple fantasy mags. We got a fairly large and loyal following in the first few years, and the rest, as they say, is history. We came up with the Draft Sharks name because I also moonlighted as a hold ‘em poker player 4 or 5 nights per week (back in the day of no kids). So I went from being somewhat of a “card shark”… to being a “Draft Shark.” The name had a ring to it, and a friend of mine came up with a pretty sweet logo, which we still use today.

2. What led you to charge for access to Draft Sharks content when so many free sites exist?

Back in the late ’90s, almost every fantasy site was free. I guess I’ve always felt that our opinions and analysis were worth paying for. And I never wanted to have 100,000 people following us. I always envisioned our community being a bit more exclusive, and one way to do that is to charge. At bottom, if you’re giving advice to everyone for free, what good are you doing your readership? Anyone and everyone can come and read your stuff — and they’re competing against each other, so there isn’t a competitive advantage for your readership. I understand the free model, I’ve just never been a big fan of it.

3. Has it been difficult at any point to stay the pay route? Have you considered turning free?

Nope, never really considered it. It always seemed to me that counting on ad revenue to pay the bills was a bit too unnerving for my tastes. And again, I didn’t want a community of “anyone and everyone.”

4. What kind of costs (in time and money) went into launching the site? How did you go about introducing your site to the marketplace — to potential subscribers?

A lot and a lot. Our model was to have a small selective group of writers. The downside to that model is that it takes a lot of time to produce content. But I have to say that it is very gratifying. As for introducing the site to the marketplace, we dropped close to six figures in the first 2-3 years on advertising. Word of mouth also helped a lot.

5. Looking back, was there a particular event or time that indicated Draft Sharks had “arrived”?

Yeah, in the very first year, I wrote what has been become one of our marquee articles — our “First Round Bust Candidate.” We called out Steve Young, who was coming off a monster year in 1998, and warned our subscribers away from drafting him. That preseason, we started to get some emails from readers who loved the pick — and some flames from readers who thought we were nuts. I knew then that we were relevant and that folks were reading our stuff — and it was making them think outside the box. As I recall, Young got knocked out by the Cards on a Monday night game in Week 3 — and that concussion forced him into retirement. I actually cheered when it happened. I met Young 5 or 6 years later. And after talking to him for a few minutes, I didn’t feel bad for having cheered when he got hurt!

6. What other sources does the site derive revenue from beyond subscription fees? What kind of business partnerships have you had along the way, and what role have they played in revenue generation?

Our revenue beyond subscription fees is minimal. We’ve gotten a few advertisers here and there for 2010, but after trying to capture advertising revenue the past couple years, we’ve come to the conclusion that it simply wasn’t worth having the site look like a banner farm.

7. How important are the customized cheatsheets to your platform? How long did that system take to develop, and how quickly did it catch on with users?

It’s pretty popular, as we get quite a bit of positive customer feedback on it. The rankings are based on a Value Based Drafting system — which is to say, it measures relative player scarcity at each position based on the particular scoring rules of your league. Conceptually, it’s something that came from Rotisserie Baseball and was introduced to fantasy football by Joe Bryant. I think I’m right in saying that Draft Sharks was the first site to have a VBD tool, as it was part of our original site in 1999.

8. What was Draft Sharks’ relationship with the WCOFF when you co-founded the event and during your run as co-owner?

Ironically, there really was no relationship to speak of. The WCOFF advertised with Draft Sharks, but Emil (Kadlec) and I made a conscious decision not to co-brand our other businesses or to leverage those brands to help the WCOFF. One of the reasons is that I didn’t want to blur the line between Draft Sharks as a content site and what the WCOFF did. I’ve always been diligent in keeping Draft Sharks as a fantasy football content site only. Again, I want Draft Sharks to have the best fantasy football analysis and content available — but I’m not trying to be all things to all people. That might not be the smartest business model, but in the long run, I think it’s only fair to your customers to have a single focus.

9. How have things changed over the years in terms of what customers expect and what your site has to do to stay competitive? Have there ever been thoughts of expanding to include other sports?

People are far more tech and Web savvy then they were a decade ago. We took a long, hard look this offseason at where our site was in terms of design and functionality and found there was a lot to be desired. We did a complete redesign of the site this spring and just re-launched this week. So far, the response has been fantastically positive. As for doing other sports, we had a sister site for a few years that did fantasy baseball. In the end, we decided it was best to stick with just fantasy football — since that was our passion.

10. What do you envision for the future of DraftSharks.com?

Good question. I’ve seen a lot of changes in the industry since 1999, and my biggest concern is that the industry used to be defined by a bunch of regular guys who were passionate about fantasy football. What I see now is a corporate takeover of the industry. Look at how many sites have been bought out by billion-dollar, multi-media corporations. Look at how ESPN, NBC, CBS, and even the NFL itself, have entered into the marketplace. Maybe it’s me, but it just rubs me the wrong way at times. There seems to be a “sameness” that infects the landscape of fantasy football content. That said, maybe all the movement toward the corporatization of the hobby has helped more clearly define who we are at Draft Sharks. We don’t want to be everywhere on the Web. We don’t want to be all things to all people. We don’t want to become a mega-site that churns out words by the pound. In the end, we’re just a small, tightly knit group of writers who drink beer in the office, work crazy hours, and absolutely love what we do. I always tell our writers: “Think outside the box. Be bold. Make people think. Tell them something they don’t already know.” We’re a bit like the show LOST. If you get it, you’ll love it. If you don’t, you’ll walk away scratching your head. And, ya know what? I’m good with that.