Unreadabe Episode 4: Will Leitch

Unreadable is back, and our first guest is Sports on Earth writer and Deadspin co-founder Will Leitch. It’s a rip-roaring conversation, covering his childhood as a budding artist lacking all practical skills in Mattoon, IL, all the way through a failed engagement on the even of his appearance on Win Ben Stein’s Money, to New York, where he made his name as the co-founder of Deadspin, got screamed at by Buzz Bissinger, and went on to work for New York Magazine and Sports on Earth. Will’s one of the most fascinating guys in sports media today, a pioneer in many ways, and I think I did a little dance when I read his email agreeing to be on the show. Check below for time stamps.

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0:00 – Introduction all by myself, some stuttering
1:20 – Will scoffs at the notion of himself as a “youth infusion”
1:45 – Predictions for what Gregg Doyel will be like at age 70
2:30 – The notion of online personalities always seeming young
3:40 – Will’s childhood in Mattoon, IL
4:30 – Living up to a dad with practical skills you lack
7:00 – Will’s relationship with his dad, and the book “Are We Winning?”
8:30 – Trying to prove to his dad he’s not a moron- the endless battle
10:30 – Will’s work ethic, and where it came from and how it started
11:30 – Growing up with Tim Grierson, dreams of becoming film critics
13:30 – His first job in NYC, how it failed, and answering phones at a doctor’s office
14:40 – Getting over the early-20s feeling of being special, and moving on
15:00 – Meeting AJ, and the romantic feeling of being collective failures
19:20 – College at Illinois, living the newspaper life and missing out on the fun
22:10 – Will’s first engagement, appearing on Win Ben Stein’s Money hours after it ended
27:00 – Leaving LA, moving to St. Louis and working for the Sporting News
29:00 – His first site, Ironminds.com, gets bought, and it’s off to NYC
30:00 – Knowing standard sports journalism wasn’t for him, and where that began
32:10 – Meeting A.J. Daulerio, and why he’s so successful, and their early days
36:00 – How Tommy Craggs runs Deadspin
36:50 – How Craggs and Daulerio solidified Leitch’s legacy as co-founder of Deadspin
38:50 – Black Table.com, which began in 2003, and how that created the Deadspin opportunity
41:00 – Leitch’s memo to Lockhart Steele and Nick Denton that started it all
42:00 – How Will became the no. 1 man at Deadspin, and the team he formed
45:40 – He turns Deadspin into a success, the early days, the Orton/Leinart posts
47:30 – Relationship with the mainstream media, the unexpected journalism culture war
48:10 – The realization that Deadspin was a flashpoint, and was controversial
51:20 – The sensitivity of sports journalists, and the role tv plays in that
53:30 – Will’s appearance on Costas Now, and being yelled at by Buzz Bissinger
59:40 – Moving to New York Magazine, and why it was the right time to leave Deadspin
1:04:30 – Will gets married, releases his book in 2010, and how that writing is different
1:06:40 – Fatherhood, what it’s like, how it affects being a writer, why NYC is a terrible place to raise kids
1:08:45 – Working for Sports on Earth, how the site had early missteps, and how Will is leading the site in a new direction
1:10:00 – Why the Internet requires a different voice, and why he’s infused young people into SoE
1:14:20 – The standard question: What’s your advice to young writers?
1:16:25 – Why “wanting it” is so important as a writer
1:17:20 – Will compares himself to Josh Brolin

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