Bill Simmons (ESPN) and Will Leitch (Deadspin): Stories of a Sports Blogger

Use your ← → (arrow) keys to browse more stories
Bill Simmons (ESPN) and Will Leitch (Deadspin): Stories of a Sports Blogger
Rob Loud/Getty Images

Not too many blogs make money. In fact, almost none do. The thing with blogs (or any website) is that you need lots of readers and lots of readers who click ads to make money. In my almost 15 years of web-surfing, I’ve never clicked on an ad. And most readers are like me. I’m guessing that less than five percent of people who read blogs have clicked on an ad in a blog.

So, to be financially successful, a blog needs millions of readers. Not tens of thousands of readers but tens of millions.

Two of the most influential sports bloggers who have achieved the readership to be successful were Bill Simmons, “The Boston Sports Guy,” who now writes for ESPN, and Will Leitch, co-founder of Deadspin, who is now a contributing editor at New York magazine.

As the Internet allows anyone with an Internet connection to create a blog, including myself, how did Simmons and Leitch separate themselves from the pack and make it?

The Love of Sport

If you don't love the sport, don't bother covering it. While the tagline of my personal blog reads, "A basketball blog for those who don't like basketball," I am being a bit facetious and love the game that I cover.

Most of us first get into sports because our fathers were sports fans and took us to loud, crowdy and exciting sporting events as children. Even if you're too young to understand the game, you understand that when other people around you yell, curse, clap and high-five, whatever is going on in front of you is special. It also doesn't hurt that scantily clad women are running around, people are shooting t-shirts into the stands with cannons and there is a laser light show before the game even starts.

While laser light shows were not around when I first started watching games, my fondest memories as a kid were going to 76ers games at the Spectrum and feeling like you were part of something big. Even if that something is cheering like a rabid dog for Scottie Brooks to throw it down with Mark Price during a 76ers/Cavaliers playoff game.

To some extent, the same thing happened with Simmons and Leitch. Simmons' dad was balancing his young son on his knee as Havlicek led the Celtics to the 1976 NBA championship. Simmons has recalled with fondness looking down onto the tunnel that led players from the locker rooms to the Boston Garden parquet and seeing some of the greats of the time up close and personal. With experiences like these, it's no surprise that Simmons would eventually grow up to become the Boston Sports Guy.

Leitch’s indoctrination into sports was not quite as idyllic as Simmons'. Instead, Leitch's father, fearing that his son was a little bookish and gay, took his son to Busch Stadium to watch his beloved Cardinals play in an effort to push him into manlier pursuits. To the surprise of both, Leitch was hooked.

Pursuit of Happyness and Early Success

Along with having a love of sports, you also need to have some idea how to write—and write engagingly—to be successful.

I have a frenemy who works as an editor and is one of the most technically sound wordsmiths I know. He would probably catch 10 grammatical errors in this sentence alone. The frenemy desperately wants to be an author, but after reading some of his drafts, I've realized the frenemy has no clue how to tell a story in any sort of interesting manner.

Simmons and Leitch are engaging and entertaining writers, and both were recognized as being excellent writers from an early age. Simmons has relayed an anecdote where his seventh grade teacher offered to become his agent—after reading something Simmons had written for class—when Simmons attained his goal of becoming a sports columnist at the Boston Globe.

Similarly, Leitch was playing Oregon Trail in his talented and gifted programs before deciding to major in journalism at the University of Illinois.

In college, Simmons and Leitch had their first real taste of newspaper writing, and both of them excelled. At Holy Cross, Simmons had his own column at the Crusader, the college paper, eventually becoming the editor of the paper. Leitch experienced similar success at the Daily Illini, where he too would become the editor of the paper.

Both Simmons and Leitch could write, and they rose to the top of their respective college papers.

Failure Part I: Dashed Dreams

When you're a recent college grad, you have a lot of optimism and dreams heading into your first job. When I graduated law school at the age of 26, I landed that six-figure law firm job in San Francisco that I dreamed of having when I first applied to school. Moving out West, I thought I was set. I had a great apartment, fancy office and I even had a secretary.

But as many of you working people know, the dream job that you envisioned, is often very different from the dream job that you have.

For the first three years of my dream job, I performed crap jobs and research assignments. I wore a suit to work but was in the office very little as I was usually sent to some dusty warehouse to review thousands of dusty wage statements held in hundreds of dusty boxes. I had to clean my five suits weekly as they were usually caked with dust by the end of each day.

For the next three years, I pretty much performed the same tasks only this time I stopped wearing suits to work.

After graduating from Holy Cross, Simmons earned a Masters Degree in Print Journalism from Boston University and then began his dreams of sports writing by working at the Boston Herald. Like most young newspaper writers, Simmons covered high school sports and had other mundane assignments. Simmons wasn’t exactly in the Celtics’ locker room, but he was writing for a newspaper and covering sports.

However, Simmons was soon miserable. Simmons described the Herald as being a “horrible experience.” Simmons never got along with his sports editor, never got the assignments he wanted and felt that the unions were keeping inferior talent ahead of him—thereby preventing him from ever even having a shot at the plum assignments. Simmons would stay at the Herald for three years, but he knew he had to get out.

After graduating from Illinois, Leitch was chosen by U. Magazine—along with three other recent graduates—to move to Los Angeles and run a magazine as they saw fit. The four graduates were basically handed the keys to a magazine and were given free rent to an apartment in the heart of Santa Monica. And Leitch had a great time.

Then Leitch experienced a personal setback as his college sweetheart and fiancé literally dumped him hours before an appearance on a game show. Leitch then dabbled a bit in drugs and dabbled some more in alcohol until his one-year internship with U. Magazine ended. After the internship, Leitch experienced professional setbacks as he applied for writing positions covering film and television, and he even tried to follow up on his dreams of becoming a film critic. However, all of these fell through.

Failure Part II: No Audience, No Money, No Hope

What do you do after losing a job without a real clear path of what's next? You delude yourself into thinking that it won't be that bad, and that you can make ends meet by freelancing or doing some other creative endeavor.

The reality is, not that many people, outside of your parents, are interested in what you create.

When I quit my law firm job to become a professional sports blogger, I deluded myself into thinking I would achieve a huge following by merely recapping the games from the previous night. What I didn't consider is why anyone would want to read my amateur recaps when they can get video highlights, box scores, play-by-play breakdowns from ESPN, Foxsports or any other website.

It's after these delusions end, that you have to deal with the realities of being unemployed. This is where I'm currently at in my blogging career.

After Simmons gave his two-weeks notice to the Herald, his plan was to support himself as a freelance writer. He tried this for three months and was eventually broke and bartending. Simmons would bartend for a year, while continuing to take on freelance writing jobs. It was at this point that Simmons seriously considered “new media” or web publishing. Having had a terrible experience writing for newspapers, Simmons believed the Internet was the only real opportunity available to a self-described 25-year-old wannabe sportswriter.

At the time, AOL was beginning an electronic newspaper called Digital City. There already were a few columns on Digital City including a Movie Guy column, and Simmons badgered the editors of Digital City into giving him a sports column. Simmons succeeded, and he now had his own "Sports Guy" column.

But the column did not mean success for Simmons. It was not a clear line from Digital City to ESPN where Simmons currently sits.

For the first 18 months at Digital City, Simmons’ audience basically consisted of his hundred friends to whom he emailed his column. Approaching 30-years-of-age, earning $50 a column and having never earned more than $30,000 a year, Simmons considered giving up on sports writing to become a real estate broker as he was beginning to believe he could not earn a living writing about sports.

Leitch would also turn to new media. Unable to find the right position in Los Angeles, Leitch moved to St. Louis where he wrote for the Sporting News online edition. Leitch was relatively happy at the Sporting News, but he experienced big-fish-in-small-pond syndrome and left to take a job in New York writing for the New York Times Arts and Living section. Leitch only stayed at the Times for four months, when he decided to throw his hat back into new media, writing for Ironminds, an online magazine.

Leitch initially enjoyed success at Ironminds, but the magazines’ funding ran dry, and he was soon laid off. Leitch was unemployed for about a year with a delusion that a job would be handed to him. None ever came.

In this time, Leitch had to deal with the reality of bills, rent and no income. Leitch took on some freelance work, but most jobs fell through. Leitch even left New York for a period of time, returning to his hometown of Mattoon, Illinois, to work on a book about his Life as a Loser column and to ask his parents for financial help.

With his parents’ help, Leitch returned to New York, paid off his debt and began his job search in earnest. He applied to a variety of jobs, including at a movie theatre, and he was eventually hired as an editor of another online newspaper. But to his bad luck (and bad “first impressions”), Leitch was laid off again. Leitch then tried temping, including a gig stuffing envelopes. In his own words, Leitch described this time as:

“I just don’t know what the next step is. Perhaps that’s what temping really is for. For people who have no idea, not a goddamned clue, what they’re doing with their lives. People for whom a weeklong job is a huge commitment. People in limbo, between two phases in their life, neither all that appealing, treading water, waiting for life to tell them what to do next. Never thought I was one of those people, but, well, hey, I also never thought I’d be so damned good at stuffing envelopes, either.”

It was at this point, that both Simmons and Leitch would have to decide whether to continue writing or whether to pursue a new field to earn a steady paycheck.

Not Going to Law School, Covering Sports from a New Angle

To their credit, neither Simmons nor Leitch gave up on their dreams of becoming a writer. Simmons did not become a real estate broker, and Leitch did not follow his mother's advice and go to law school.

What they did do was create something different—something successful—that would change the face of sports writing.

Simmons wrote about sports from a fan's perspective. While this is commonplace today, no one was doing this in the late 1990s. Newspapers were the dominant voice, and the papers wrote in a certain detached and unbiased style. Simmons did the opposite and wrote as the hyper-obsessed fan. Simmons carefully cultivated the Boston Sports Guy persona, and he slowly began to attract an audience of fans who wanted to read stuff written by fans.

The hundred friends Simmons was emailing his column to, slowly began to forward the column to their friends, and their friends to their friends, and so on. It was a slow process, but Simmons, and his unique and engaging style, eventually attracted the attention of ESPN.

My greatest disappointment in reading Leitch’s Life as a Loser column is that he ends it a year short of when he starts Deadspin.

After temping for a short while, Leitch eventually got a full-time job as a writer covering the financial industry. Leitch enjoyed the job, primarily because it was a j-o-b offering a steady paycheck. I would have loved to read Leitch’s thought process heading into the creation of Deadspin and what he was thinking leaving a steady job to once again try a new online writing venture when he had experienced failure so many times already.

Like Simmons, Leitch did something at Deadspin that no other sports writer was doing. He approached sports from a papparazi-like perspective, writing about athletes’ private lives, their girlfriends, troubles and basically attacking the industry that he covered. This filled a void in sports coverage, and Deadspin immediately resonated in the TMZ era.

Researching Simmons and Leitch impressed upon me their drive, confidence in their own talents and love of writing. When all the signs were telling them to change careers, they stuck with it.

I'm not sure what I would do after 7-8 years of futility as a writer as both Simmons and Leitch experienced. I started my writing career about 10 years later in life than Simmons or Leitch, and I also do not have the journalism background (or reinforcement in knowing that I can write) that either of them possess.

After even one year of futility, I'm not sure I would be able to stick with this before trying to reenter the legal world.

I'd hope that I could be as strong, confident and motivated as Simmons and Leitch. From their experience, I know that while anyone (including me) can have a sports blog, the trick to be successful is to do something that no one else is doing.

What that is, I haven’t figured out yet.

Load More Stories

Follow B/R on Facebook

Out of Bounds