Will Leitch On His Career, Founding Deadspin, And Whether He Still Reads The Comments

Will Leitch is best known as the founder of Deadspin, the incredibly influential Gawker sports blog started in 2005.

He left Deadspin in 2008 for New York Magazine where he is now a contributing editor. He’s also a senior writer for Sports On Earth, and has contributed to The New York TimesEsquireThe AtlanticGQ, Bloomberg Businessweek, Fast CompanyParade, Glamour,The Nation, and writes movie reviews for Gawker. Odds are good that you’ve read Leitch’s work at some point, whether you realize it or not.

Leitch, who still reads Deadspin everyday, loves how the current site operates, even if it is completely different from how he ran it.

“When I ran it, it was kind of a niche site, but it needed to get bigger and do different things,” says Leitch. “I think they are doing incredible work. There’s obviously stuff that they do that I wouldn’t do, but that doesn’t mean I’m right. In fact, I’m pretty sure it means I’m wrong.”

For Part 1 of our Five to Thrive interview we discussed his career, founding Deadspin, and what it’s like to operate in a media climate he helped create.

– 1 –

SB: So tell me about your background before Deadspin. Did you always want to be a sportswriter?
WL: I’d never actually written a blog before. I went to journalism school at the University of Illinois and wanted to be a movie critic like Roger Ebert who was my hero. I always wanted to be a film critic but when I got to college I started covering sports on the side. I realized that everybody who covered sports is miserable. They hate their life and more importantly, hate sports. So I was like, ‘Well, I know I’m never doing that.’ So, I didn’t. I graduated in ‘97 and worked as a film critic for a while. I eventually moved to New York to try and make it as a writer. And for about five years I basically starved. I answered phones at a doctor’s office for two years because I needed the internet access.
My friends and I got really frustrated because we all moved to New York to make it as writers and nobody wanted our stuff. So we started our own website. It was a literary journalism site called The Black Table. It was four people, one of whom was AJ Daulerio, who took over for me as editor of Deadspin and then Gawker and then all that came with that. So that was our main project, we finally got tired of not getting any jobs so we started our own site. It was barely about sports, we only mentioned sports every few weeks. I wrote for it all the time. I wrote a column called ‘Life of a Loser’, which ended up being made into a compilation for a book. And nobody read it, but we got to do things our way which made us happier because we hated our day jobs.
In 2005 a site called Gawker got started and it was all about New York media. They were desperate for things to link to so they linked to our stuff a lot. They saw my writing and liked it and asked me if I  wanted a sponsorship for six months to run a gambling blog. I said, ‘Actually, I hate gambling, but you guys should do a sports blog.’ I based it on this idea that everybody I knew in sports was miserable and they didn’t write about what sports were actually about. I wanted to write about sports the way people actually talked about sports. I wrote this long pitch memo and they said, ‘You’re cheap and nobody knows who you are so we can get rid of you and no one will care, so, sure here’s six months, give it a shot!’  That site became Deadspin which was launched in September 2005, and it got a lot bigger a lot faster than anyone anticipated.

– 2 –

SB: What were the early days of Deadspin like compared to what it is now? What led to your decision to move on from the site you created in 2008?
WL: It was just me, but now they have a huge staff of people and they go to the office and they get a conference room. When I was doing it, it was just me getting up in the morning and writing all day and then going to bed and getting up the next day and doing it again.  To see what it’s become, I’m honored but it’s still a little bewildering. So I did that for about two and a half years and I enjoyed it, but one of the problems I have with media is that people reach a certain level and they only start talking to people that agree with them . I enjoyed doing the site but I felt like I was preaching to the choir in a sense. It was also about the time that people started monetizing this stuff, and I figured they were going to start making me do things I didn’t want to do. So I got out and went to work for New York Magazine and I worked there for five years and I’ve written a number of books and for numerous publications. But I still feel like I’m doing the same thing I was doing when I was writing Deadspin, I’m just doing it in a different format. It’s the same tone and the same style of writing.

– 3 –

SB: Deadspin was known for it’s vibrant and hilarious community of commenters long before most major sites had a comments section. What made Deadspin’s commenters so great, and how do you think that helped pave the way for bigger sites like ESPN to have comment sections?
WL: When Deadpsin launched, the word ‘blog’ was not allowed on ESPN. It was like a bad word in that world, so yeah I remember they opened up comments almost by accident on one SportsNation chat or something and I sent the Deadspin commenters there and it was like they all just got to play in the adult playbox and peed everywhere and it was hilarious!
One of the keys to Deadspin’s success was that I never wanted the site to be like ‘Hi, I’m Will Leitch and I have an opinion, now respond to my opinion.’ That’s never been what the site was about. I’m an idiot just like everyone else, I make no major claims to know anything more or be an expert. It’s stuff that’s fun to talk about. I think one of the reasons that the comments section was awesome was because people were waiting for a site that was not stupid. But I also think I tried to foster this idea that this is all in fun and we are all doing this together. It’s amazing to me that writers can’t believe these terrible things that people say online. Of course, a lot of these things are stupid, but I spent 10 years writing stuff every single day that was read by no one that I was desperate for people to comment on. I was just writing for myself and trying new things and getting stuff out there for years and years before Deadspin launched and nobody ever read any of it.
So the idea that now that I actually have readership, I find it amazing and an honor that anyone even cared enough to say anything. I remember for so long when nobody cared. It’s amazing to me in this day and age how many people get so offended by what people say about them online. It’s not real life and the idea that everybody hates you is not actually true. And secondly, this is good, it’s actual interaction with people. This is actually a conversation that I wanted the site to be about from the beginning. I always loved the idea that what came above the comments section and what came below the comments section were different, but one was not better than the other. That’s one of the reasons it turned out to be such a good comments section.

– 4 –

SB: There’s a new push to eliminate comments sections from major websites as they have become overrun with trolls and as social media has made them irrelevant. How do you feel about that?
WL: It strikes me as a colossal waste of time. I understand why people are doing it. I used to run a movie site for Yahoo! And you could put a picture of a bunny and the 10th comment would be about how Obama was a socialist, the 20th comment would be about how Bush took down the World Trade Center, and the 40th comment would be “First!”
Of course comment sections are ugly. I find it so weird that people have this notion that a bad comments section detracts from what people are commenting on. That’s crazy. If you don’t want to read the comments, then don’t read them. I swear to God, you don’t have to read them. You can go your entire life without reading comments if you don’t want to, but the idea that you think it gets a little ugly down there or people are saying things that you don’t agree with that you should shut them down, to me seems antithetical to the whole idea.

– 5 –

SB: Do you read the comments on your work now?
WL: I admit, I do not read the comments on my work anymore, not because I don’t think people should be doing it or that there isn’t value in what they say. Woody Allen has this saying about why he doesn’t read critiques of his work, where he says ‘You can’t believe the nice stuff and not believe the bad stuff.” For me, I have an idea of what I’m trying to say and everyday I write multiple pieces for a bunch of different places so I have a pretty good idea of how my voice works and what I’m trying to say. If I start thinking when I’m writing about what a commenter is going to say or about what they may say on Twitter, then I’ve already lost the battle.
I don’t read them but that’s not because I think everybody is an idiot. I actually think it’s great and even if 15 people are calling me an idiot, that’s 15 more people than ever read anything I ever wrote.
Worrying about how everyone is reacting to the work you’re doing all the time is distracting from the work. It turns it into something that is different from the reason most people got into this to begin with.
Check back on Monday for Part 2 of our discussion with Will.


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