A while back I heard Bill give a great breakdown of his time at ESPN and how he came to rise through the ranks at the company, as well as how he grew what’s now an enormous digital footprint with sites he’s created that have driven millions of unique visitors a month, millions of Twitter followers, appearances on nationally televised shows, and so on. Since I thought the content was really valuable, we wanted to reproduce it here in transcript form for those interested in growing a digital brand (find the original podcast, along with all of the Bill Simmons Podcast here if you’re interested). The transcription starts as Simmons launches into his time at ESPN, the Wesley referred to is his former co-worker Wesley Morris whom he later interviewed bit.
Wesley’s coming up in a little bit. Have a bunch of things to talk about with him. I wanted to talk about espn.com 20th anniversary. They’ve been celebrating it all week on espn.com. Had a couple pieces. I want to talk about my experiences with espn.com just…I get this email all the time. “How did they find you? Where did you come from? What’s your story?”
I just thought I’d put it in podcast form for 15 minutes, just once and for all. You can just hear it from me. I graduated from college in 1992, and then I went to school for journalism. Graduated 93 from BU, and I wanted to get a sports column. I just assumed, I’d had a column in college for four years at Holy Cross, pretty much the entire time. I got it when I was a freshman in college. It was called “The Ramblings.”
Somewhere along the line I though maybe it’s something I wanted to do for a living. Went to journalism school, and just assumed I’d come out and I’d get a column. I got a job working as an intern/high school reporter for the Boston Herald coming out of grad school.
Answering phones, doing Chinese food orders, answering calls from volleyball coaches like, “Eh, [inaudible 2:37] two sets to nothing,” and just get who had the most hits and stuff like that. Gradually, I started covering a little bit more, and the next year, became their lead high school guy.
I was doing football. I was doing basketball and baseball and doing some features on things. I wrote a couple of op-ed pieces.
My third year at “The Herald,” I started writing a lot of stuff for “The Boston Phoenix,” which was a weekly at the time. I was also looking at the landscape for how The Herald worked. I just could not figure out how I was going to get a column, because, at that point, the newspapers were run by unions.
I just didn’t see anybody leaving. I was just looking at the landscape and just thinking, “How am I going to get to where I want to go? I’m going to go crazy.”
At that time, I had taken a job with benefits, where I was working on the copy desk, copy editing stuff and handling different [inaudible 3:45] on the scoreboard page and all this different stuff. I was working a lot of nights and not writing as much as I wanted. I’d really put my eggs in the Phoenix basket, and they changed editors. All of a sudden, they didn’t want sports.
Everything just came together in late March/April ’96, where I was just like, “I’m going to be here three years from now doing the same thing. I don’t know how to get to where I want to go.” There’s really no Internet at that point. The Internet was underground, and people had email. I don’t even think I got an AOL account until the summer of ’96.
I made the decision to leave. I was going to try to freelance, and it was going to go great. I was going to freelance for “Boston Magazine” and Boston Phoenix, all these places. Three months pass. I don’t get a single freelance job other than…I got one feature for “The Worcester Phoenix.”
At this point, I’m 26 years old and my writing career has just gone down in flames. I’ve no idea what I’m going to do. I start bartending because I need to make money, because I have an apartment in Charlestown. I need to pay the rent somehow. I’m getting too old to ask my mom for money.
Bartended for the next year, and I didn’t really write anything. I’d created this stupid TV show, and I wrote a bunch of episodes for it. I’d no idea what I was doing. I was writing the episodes in Microsoft Word. It’s got to be terrible. I’m afraid to look at it.
Was bartending, I was getting up at 1:00 in the afternoon every day and staying up till 3:00, 4:00 in the morning. I was hanging out with all people who worked in different bars and just going out and just being a putz.
At some point, I realize that I wasn’t ready to give up the writing thing yet and there was a site in AOL called the Digital City Boston. AOL had broken out all the cities into digital newspapers. They had this guy he was called The Movie Guy, he was called Boston’s Movie Guy. His name was John Black I think. I think his name is John Black.
He was [inaudible 5:57] movie reviews and he has this little page and he was like, “Boston’s Movie Guy!” and he was basically branded as their movie guy. I thought, “Wow, I could be Boston’s sports guy. This is great!” I grew up here, I love all the teams, I live in Boston now, I’ll create a sports column for them.
I started badgering the editor of this site. A couple of months passed, and he’s interested, I met him, and it might happen, and now they’re going to build the site. Now we’re talking it’s spring of 1997. At that point, Digital City Boston it is only available AOL only and that’s it.
We make a deal, he’s going to give me a chance for three months and I’m going to make 50 bucks per week for three months which I didn’t care because I was making enough money working at a restaurant. I was like, “I’ll do anything for a chance.” Another month passes, “Are they going to build the site, what’s going on?” I’m badgering.
Finally, in May, the site is ready and I had this whole plan for other stuff I want to write. My idea at that time, if I’m going to go down in flames, I’m going to go down in flames like me. I’m not going to try to write like a traditional newspapers columnist. I’m going to try to write from a fan’s perspective. I’m going to write about the stuff my buddies and I talk about.
I know I wanted to do a mailbag. David Letterman was a huge idol of mine growing up and I knew there’s some way to involve readers much like Letterman use to involve his viewers. It bounced off the readers and in my head, I was like, “Go send me emails and I’ll use them, and then I’ll write funny responses.”
I had that. I knew I had the ramblings which now is basically turned into Twitter but at that time it was a one-liner column which I use to love. [inaudible 7:49] used to do those in the daily news in the ’80s and I always was, “I’ll write a one-liner column.” I knew I want to do NFL picks because I loved Pete Axthelm who wrote a games column for Inside Sports.
At that time, somebody in the Globe had an NFL picks column where they just picked every game. I can’t remember who, it wasn’t very good. I thought I can do better than that guy. Then I knew I want to write a lot about NBA because I love the NBA, been going to games. I knew I was going to write about the Boston teams and I knew I was going to write a ton of pop culture.
I had this whole plan. My first column was about the Celtics who had just, I think lost the Duncan lottery. It was like a behind the scenes dialogue piece with the Celtics. It wasn’t very good. I started writing more and more, and I remember the NBA finals where that era’s [inaudible 8:45] Karl Malone. I had a lot of columns like, I put this column, “Malone, [inaudible 8:51].”
It was not a lot different than what I was doing now or what I would do now. By the summer, I got my feel for it and I remember that summer I wrote a piece about the 30 worst sports movies ever. They ended up putting it on the AOL main page, and all of a sudden I got a lot of traffic for it. At that time I was AOL only.
Eventually, I figured out what I was doing and they gave me a different contract. Then at some point, they gave me a year-long contract. I think in summer of ’98, but for the first 18 months I was doing this site and I was also doing all this stuff I’m doing at the restaurant.
In the fall of ’97, we had an NFL picks contest and I picked nine people to go against me in NFL picks for that year. I would make the picks, I wrote my picks column then we had this separate piece with nine other people making the picks and the winner got something. I can’t remember.
Two of the people in that picks contest ended up getting married. Another person in there was a 15-year-old kid who was really funny named, Jamie Agen, who ended up we became friends, he became one of the best people on my mailbag. When he graduated college, he became my first intern at espn.com and then eventually moved out to LA because I introduced him to Jimmy Kimmel and got a job there.
It’s just kind of funny, all this different stuff that happened for that one picks contest. In the summer ’98 the Boston Globe wrote a piece about the site and about me. This guy Howard Manley wrote a piece. It was the first kind of big break I’d gotten, where it was like, “Somebody had noticed the site.”
At that point, I was pretty hard on the media people because that’s what you do when nobody sees you. You always take shots at everybody who’s doing better than you.
I was doing a lot of that too. Part of his piece was about me going after WEI, which was the local radio station, which was terrible and it’s still terrible. Me taking a lot of shots at them. The piece about that.
The site was building enough momentum that I realized that I could probably leave all the other stuff I was doing and just throw myself into this site.
That’s what I did for the next, basically, two-and-a-half years. Right around ’99, I started to figure out what my voice was. I remember there was two different columns, I think it was in March of ’99.
One was the first column I ever wrote about going to Vegas with my buddies. It was about the whole weekend being in Vegas with them. This epic gambling run we had at Treasure Island on a Saturday night, me and my buddy Bish.
At that time, I had no money. We were at $10-table, I’m betting $25 and it was the craziest bet we could make because there were real stakes. If you lost eight hands, you’re done for the weekend. We just had this crazy one when you’re getting drunk and we were winning our bets…
At some point, I go to the bathroom and the Undertaker’s in there, the wrestler. We were just peeing next to each other and I’m wobbling, I’m drunk.
He finishes and he’s walking away and I just muttered to myself something like, “Wow, I’m up $800 and I’m taking a piss next to the Undertaker, doesn’t get any better than this.” We were the only ones in the bathroom, there was four second pause and all the sudden he goes, “Mm, sounds like it,” and walks out.
I wrote this whole story, and that was one of the key stories in that. Just in general, to kind of capture what it was like to go to Vegas when you have no money in your late 20s. It was one of the first times I was like, “I feel like this could be something bigger. I felt this could appeal to more people than just Boston.”
The other piece I wrote at that time was something about the passes, entourages. The NBA was big. Everyone had an entourage in the NBA back then. I wrote I was like, “What’s the key to being in an entourage?” It was more of a mainstream piece than a Boston piece.
Gradually, over the next two years I figured out how to blend the mainstream stuff with the Boston stuff, the pop culture stuff and all that stuff. I was working my butt off.
I was waking up every morning, at 7:00 in the morning I was doing this thing called the Daily Links. I go through all these different websites, the whole day, and I would pick the pieces I liked and I would put them, and I would release them around lunch time so people could read 15, 16 pieces that I really like from that morning.
The thing was, at that time there was 28k modem. The sites would load really slow, it wasn’t like it is now, you just click on the site and it comes up. If you would click on espn.com, it would take 30-45 seconds to load. I would watch TV shows as I did this. I think for two straight years I was watching either 90210 or ER because they were rerunning 90210 and ER constantly.
I always wanted to have something that wouldn’t distract me too much, but would also keep my attention as I was sitting there watching my stupid computer load.
I would just watch the 90210 in cycles. They would take six months to finish, or four months, whatever it was. Then it would start over again, they were like juniors in a high school, and I would just re-watch that again, same thing with the ER, they would just rerun them.
That’s what my life was like. I would do those things in the morning, I would go to lunch, I would get a big coffee and I would go to Sorrells Pizza in Charlestown, I would come back and I would try to write my column as fast as possible. I write three or four columns a week at that time.
That’s all I did. All week, every week, Monday through Friday. Just everything I could do trying to get noticed.
In 2000, espn.com launched page two. They were talking about not just sports but pop culture too. They had Hunter, and then they had Ralph Wiley and Halberstam and a couple of other people. They had never asked me or approached me or anything.
At that time, I had probably, I would say, maybe 10,000 loyal readers per day. I left out one part. When we were AOL only there was no way to get to the site from the Internet.
My buddies at work couldn’t read my pieces unless I forwarded it to them. I would forward my AOL pieces to my buddies and then they started forwarding them to buddies.
Over the course of a year-and-a-half all of a sudden there was this email chain where people kept asking me to be on the distribution list. I had this whatever distribution list of friends and friends of friends that I would send them out.
I would send out the column and I remember a couple of times, the column that get forwarded back to me like, “Hey, you should read this piece on some stupid movie” or whatever, I was like, “That’s my piece! You guys are mailing this back to me, how did this happen?”
Anyway, when AOL, the Digital City Boston finally went out to the Internet, then it enabled a lot of people to see my stuff. By a summer of 2000, page two was launched.
Maybe it was fall or December, I can’t remember, they hadn’t asked me to be on and Fox Sports had come after me at one point but then they all of a sudden cooled off. I did three years and I really felt like I was good at this.
I felt like I had real fans. I couldn’t figure out why there was some piece missing. I was like, “Am I crazy? I feel like I could do this for a living, I could have fans. I don’t understand, there’s something missing. Why hasn’t this working out for me, is this a conspiracy?”
Maybe late summer 2000, I remember going to dinner with my girlfriend at the time, who’s now my wife, and my mom and my step-dad, who is in commercial real estate.
Seriously thinking about, it might be time to give this up. I just turned 30, I’m about to turn 31, nothing seems to be happening, I’m freelancing for all these different places but I’m making 32,000 a year, 35,000 a year.
I have friends who are making three, four times as much money as me. I don’t know what to do. Is it maybe time to say, “This didn’t work out.” Everybody convinced me, “No, no, you got to give it one more year.”
In February 2001, the SPs and I did a running diary at the SPs. Running a diary was another thing that I used to do all the time.
A guy named Norman Chad used to write for “The National.” He would do running diary sometime or just watching the game. I really like that format. I took that format, which is really smart, time stamps, try to blow it out, and make it a much bigger, longer piece.
I didn’t care about the length of my columns because I grew up reading Peter Gammons and some people like that. It took 15 minutes to finish a Peter Gammons’ column. I used to look forward to that. 15 minutes, that’s great.
This is going to be a great 15 minutes for me. I never cared about the length of column because I figured if it was good enough, somebody would be excited that they had something to do for the next 15 minutes.
I did an SPs diary in 2001. It was the second time I had done it. I had done one in 1999. That wasn’t as good. This one in 2001, I really knew what I was doing at this point. It was good. It started getting forward around the ESPN headquarters.
A guy named Vince Doria, who just retired, who is a legend, who ran the “Boston Globe” and ran ESPN, he ended up seeing the thing. It started getting forwarded around the offices. I was not [inaudible 19:10] a spin in this piece, but I was also justified because the show was terrible.
Eventually, John Walsh saw it. He just became obsessed with, “Who is this guy? This is interesting. How can we…?” whatever. He started reading me. Then he told the “Page 2” guys to give…He was like, “You got to try this guy out.”
Now, John Walsh is a legend and ended up becoming one of the most important people in my life, but I didn’t know that at the time. He had launched “Inside Sports,” which is my favorite magazine growing up. He became the guys who revitalized, rejuvenated, and recreated “SportsCenter.”
He had launched ESPN Magazine. Now he’s basically launched Page 2 and had gotten heavily involved in espn.com. End of March, I had just done Bob Lobel show in Boston, which was the best 11:30 Sunday sports show.
I wasn’t very good, but it was a big moment because there is a little bit of a credibility that went with that, that at least, I was good enough to be on Bob Lobel show, or at least, I was well known enough locally to be in Bob Lobel show.
Then I got this email out of the blue from Kevin Jackson. It was one of the Page 2 editors at that time, asking me if I wanted to write a piece about Nomar, who had just blown out his wrist. He’s done for the season.
I ended up writing the Nomar redemption, which was about how Red Sox fans loved Nomar and Pedro. We’ve been losing for decades and decades, but we’re holding on to this hope and then tied it in to the Shawshank, which is funny because this probably one of about 70 columns, where I somehow worked Shawshank into it.
It’s a good column. It was a lot different than anything that was on espn.com at that time. When it went out there, they led the page with it. They might have even led espn.com with it. It did really well. They asked me to do another one.
The second one I did for them, it was an NBA awards…No, the second one was “Is Roger Clemens the anti-Christ?” That was the second one. That was the second and third one. I did one with an NBA column with awards, movie awards.
By the third one, they decided they wanted to potentially hire me or start using me more, but I was also getting approached by the “Boston Herald,” who wanted me to come back, basically take my website and move it to the Boston Herald, and write for them.
They gave me an offer. It was benefits. I was like, “I have to do this.” At that point, I was engaged. I was ready. I had taken the site as far as I could go. The Digital Cities had fallen apart. It just seemed like something needed to happen. I announced that I was shutting down my site in June. I was thinking about going to Herald. I told my Page 2 editors that.
The next thing I know, I’m going to Bristol and I meet John Walsh. My buddy, Gus, who worked at ESPN at the time, who had been trying to get them to look at my stuff for years, like nobody was really that interested.
Walsh was, however, he saw it was the first one who really pushed them. I met with him. I was told, “Walsh is somebody. He waits you out. He’ll stare you down. He’ll use silence as his weapon.”
I met him and just started talking about Inside Sports. We just hit it off. He’s like, “Look, we want you here. We love what you do. We want to give you a column on Page 2 three times a week,” offered me this contract, which in retrospect was probably the worst contract in the history of media.
It wasn’t the money figure as much as they had the option after the first year and after the second year. They basically owned me for three years. I had no ability to get out. I was so happy to get any offer, I just grabbed it. The only thing I asked for was the chance to take off five weeks before I started.
I wrapped up my site mid-June. I took five weeks off and just basically planned out how I thought the column would work because at the time, nobody had any success whatsoever as a national columnist. Everything was local, which is everything.
All right, so what are the reasons for that? If you’re a local columnist, you can use all these references and this historical database of all the local teams.
You’re in Boston. You get all these jokes and references you get to pull from Red Sox’s history, Celtics, Patriots. You get to be really hyper-specific. When you’re national, you have to try to appeal to as many people as possible. It’s a different task.
I spent those five weeks. I took two weeks off. My buddy Bish got married. I went to California with my girlfriend-fiancée. I spent the next three weeks really hashing out what I wanted to do. During that time, I wrote a piece about Lenny Bias that I was really proud of for espn.com.
Then I disappeared and spent probably three solid weeks sketching out how a column would work to try to appeal to national people. One of the things I thought was pop culture could replace the local sports part, that I could use the pop culture side, much the way I used Boston sports to appeal to local people.
Everyone follows the same movies, TV shows, all that stuff. I’ll do that. I knew I could do mailbags. I knew I had the ramblings. I knew I had NBA to have a constant NBA presence. I knew I want to do NFL picks. I just hashtagged how it would go and how a typical week would go.
I knew I wanted to blow out sports movies, cover every sports movie release like it was a huge thing. I figured it out. I knew the mailbag was going to be a huge part of everything. By the time I launched in July, I had a real plan.
Fantasy was the other thing because ESPN had no fantasy at that time. One of the things I wrote in August, a month after I started, was a fantasy football, “Idiot’s Guide to Your Fantasy Football Draft” or something like that. Then I did something like a rankings thing, too.
Nobody wrote about fantasy anything at that time. It was just for nerds, Dungeons and Dragons people. A lot of it was a good spot because people are all writing about sports a certain way. The Internet was drifting another direction.
Also, the stuff did stand out at the time, which was good for me. It was going, but the big thing was, especially that summer, they were editing jokes out. They were cutting stuff. I was really starting to feel like I just sold out and that it was a dumbest move I ever made.
I remember I did an “Idiot’s Guide to Gold Club Trial,” which is this great trial that happened at the time at a strip joint, probably one of the eight or nine funniest things I’ve ever written. They took out 12, 13 jokes. I just remember being just devastated. I was like, “Oh, my God. This is the biggest mistake I’ve ever made in my life. Why am I with this?”
Eventually, as the end of summer and September, October went along, I didn’t really understand this is happening because I’m trapped in Boston. The column started to take off. That gave more leeway and more control over the proceedings.
I was able to write the column I wanted to write. After about a year, I knew the column was doing well, but I didn’t know how well. I could tell they were promoting me every time I wrote.
In general, espn.com wasn’t even close to what it is now. You’re talking 30 times less traffic, but I could tell when I wrote, there was a couple times where they lead with me over [inaudible 27:32]. I was like, “Wow, ‘Breaks’ is my favorite book ever. This is insane.”
Somewhere along the line, I completely melted down in April because first of all, I had this contract that was the worst contract ever, and outperformed it. They were gearing the Page 2 around all the stuff I was doing. I was not handling anything well, I’d fully admit that.
I just wanted more security. I was like, “I’ve killed it for you, guys. Can you give me a real contract?” Sign-up meeting with Walsh and John Skipper, who now runs everything.
They gave me a magazine column, which was 680 words, which actually was retroactively probably a mistake because I can’t even burp in 680 words, a little more security, all the stuff. They handled it great. From that day forward, I always loved Skipper because he didn’t have to help me out, and he did.
During that summer, the column was still going well. Jimmy Kimmel reached out to me. He wanted me to write for him. I should mention, going backwards, one other thing, New Orleans for Super Bowl Week. I wrote a piece making fun of New Orleans, just how lawless and crazy and insane it was to be there for the Super Bowl.
I loved it. I had just never been in a place like that. It was a little bit of a tongue-in-cheek piece. Within a day, everybody in New Orleans wanted to kill me. That was the first time I realized how much power and breadth espn.com had because I was getting death threats in my hotel room.
I’m like, “Oh, my God, what’s happening?” because my process hadn’t changed. I still had the same column writing process that I had had before, where you turn on your computer, you write something, and hit it in. Now all of a sudden, I was leading the news, like, “espn.com columnist kills New Orleans.” That’s when I realized that there was real power and breadth in the whole espn.com experience.
Fast forward to the summer, Jimmy Kimmel hires me to write for his TV show. I ended up leaving espn.com and moving to LA. I wrote every other week, basically. I could not do both. I loved writing for Jimmy’s show. I made unbelievable friends there. It was the best, but I was reaching a point where I couldn’t follow sports long enough to write my column, even on a limited basis.
There was this moment when I was at Mike Tyson…We went with Mike Tyson in the Harlem. He was feeding his pigeons. We were filming a piece for him because he was hosting the show for a week with Jimmy, when [inaudible 30:26].
I was on the roof with Mike Tyson. We were shooting for a video, but I really wanted to be writing a column about it. I was thinking about it as a writer, not as a TV person. That’s when I realized I need to go back to my column. I felt like I had an unfinished business with it.
Looking back, one of the reasons I probably went to Jimmy shows I was just burned out on the column. I’d been doing it day in, day out for five years and I think I just got a little burned out.
I ended up in April of 2004, went back to espn.com full-time. Stayed very close with Jimmy and a whole bunch of other people who was just…It was what I was meant to do. I felt like it was to write that column. At that point, espn.com was really starting to take off, and the Red Sox in 2004, that’s when they had their little run.
Everything snowballed in September and October that year when the Red Sox they beat the…They make the playoffs. They beat the Angels. Now they’re down three nothing to the Yankees. They lose one. Now we have game four, game five. The greatest two-day life experience I think I’ve ever had from sports where they fight back with the Dave Roberts game.
Then the next day, they come back, over and over again, and 25 innings over two days and just incredible, and we fend off the Yankees at Fenway Park. It was amazing. Leave that place at like 12:30. I go to have one beer before I go to try to write about what I just saw.
I’m running an old friend from Holy Cross, and we’re just talking about how amazing it was. Go back to my dad’s house in Beacon Hill. I remember I got a giant coffee, and I got a big thing of sour patch kids, and it was like 1:00 in the morning. I just started writing. I think I handed it like 5:00, 5:30.
It’s probably my favorite column I ever wrote, just because I was so drained emotionally from everything and I just didn’t have…my tank was on E. My brain wasn’t even working, and somehow, I wrote about everything.
Went up the next day and I talked to the editor-in-chief, John Papanek, at the time and I was like, “I’m just burned out. I don’t know if I can write a game six column. I’m literally fried. I got nothing left.” He gave me this great speech about, “Our site’s taking off. This is the first time the Internet has really become a truly important part of the sports fan experience.
We are right there with everything. People around the country are reading what you’re writing about the Red Sox and you got to suck it up. This is something you probably would have killed for seven, eight years ago.” I was like, “You’re right. I got to suck it up. This is like I’ve been waiting my whole life for this.” I wrote game six, game seven and all through the next series.
The reason I’m telling that is because now espn.com, it’s at the 20-year mark. It’s 78 million uniques per month or whatever the hell it is. It’s easily the number one place. They’re doing video. The site has blossomed in a whole bunch of different ways.
It’s really interesting that once upon a time, it was this little…It just wasn’t a big place and it wasn’t a place that even seemed like it could develop the personalities that could reach all kinds of people.
I remember they hired Peter Gammons just to write his baseball column only. They stole him from “The Globe” in, I think, 2000. I thought that was the biggest moment in the history of sports coverage on the Internet because that was the first time you actually had to go to espn.com to read Peter Gammons.
You actually had to go to the Internet to read Peter Gammons. That, to me, was the all-time game changer because, once they got him, and once people like my dad had to figure out how to get to espn.com, that changed everything.
There’s some other stuff that happened. People could forward hyperlinks. People didn’t know how to do that in the late ’90s. People would just copy, paste columns and people didn’t know what a hyperlink was. Now people know how to share content. Social media, I think, in 2009 really, really changed the game in a lot of ways with how people can see your stuff.
In the late ’90s and early 2000s, it was really about trying to stand out, and stand out from other people, and figure out ways to get people to come to you and keep coming. I think espn.com, the brand was a part of it, but you had some really smart people there at the time that figured out all these different ways that the site could and should stand out.
To see where it’s gone now and to think that it’s been 20 years is…In a lot of ways, it feels like 50 or 60. In some ways, stuff like me being up at 5:30 in the morning writing that column, it feels like it was a month ago.
It’s certainly the place that gave me a chance, and I worked with some great people along the way — Jay Levinger and Kevin Jackson, Mike Philbrick, John Papanek, obviously Walsh and Skipper, Rob King, on and on. That David Schoenfield, who edited my column for a big chunk of the mid-2000s, and so on and so on.
I definitely got better as a writer and as a thinker just from working for these guys. I look at some of the stuff I did in 2001, 2002. I didn’t really know what I was doing. By about 2008-2009 I really figured out what I was doing. It was a decade long of just trial and error, trying to figure out stuff.
The reason I’m telling that story is because, first of all, already asked me like how I ended up here but, also, I really did almost quit twice. I almost quit in ’96 and I almost quit in 2000. I literally almost gave up. I always get emails from writers who are trying to figure out what to do with their life or they’re hoping for some break or whatever.
There’s really no way to help anybody. There’s no magic sentence to tell somebody. Really, it comes down to, “Are you willing to outwork everybody else? Are you willing to do whatever it takes to get a chance and, if you get that chance, how hard are you going to work once you get it?” That’s it.
There’s no magic comment other than that. It’s you just have to work harder than everybody else. You read any story about anyone who did well and I guarantee at some point in there, it’s something about outworking people.
For me, I almost quit twice. I easily could have. I probably should have. Then, when I got to espn.com finally, that was it. I knew that was my chance and I was going to work my ass off. I worked so hard that I probably got burned out. I was writing 10,000 words a week, every week for a year straight, and on top of my own site, and I just got burned out.
That’s my story, espn.com, 20 years. The most important person that whole time was John Walsh. We had a lot of battles along the way. I want to have him on a podcast at some point to talk about it, but, in a lot of ways, he was my creative conscience. We didn’t always agree, but I always respected his opinion. He always respected where I was coming from.
There’s no question that my career wouldn’t have gone the way it did if it wasn’t for him. That’s it. That’s my espn.com story. Wow, that was 40 minutes. All right.