“Your ideas are intriguing to me, and I wish to subscribe to your newsletter.”
-Homer Simpson
Why Substack?
This is all Bill Simmons’s fault.
It’s not his fault that I need the money, which is really why I’m doing this, but it’s his fault you’re reading these words right now.
For those of you who don’t know who Bill “The Sports Guy” Simmons is, he was a sports writer who rose to fame writing for the Page 2 section of ESPN’s website. Page 2 was the place you could find articles, opinion pieces, and (for lack of a better word) shtick about spots that was not just the hard sports news and statistics that made up the rest of the site.
Simmons, who is an unapologetic Boston native, got his start writing for newspapers, then his own AOL site (a sort of turn of the century ur-blog) which led to him writing for Jimmy Kimel Live, and then for ESPN. He garnered a strong following by writing long pieces full of hard facts, insights from an obsessive life long sports fan, pop culture references, and wink and a nudge perspectives from an inveterate gambler. The end result of his style was that he made sports make sense by reframing the nuance of various games and players via pop culture analogy.
In the mid to late 00s he launched his podcast The BS Report (through ESPN), which featured sports guests, celebrities of all kinds, and a collection Simmons’s various friends. The BS Report (see the self-aware joke in the title…) became one of the early juggernauts of the podcasting world and presented his personality and charisma to the world in a more consumable way than just long jokey think pieces about sports. His podcast and writing, including two best selling books, led to ESPN branching out to creating Grantland, a sports and pop culture magazine that just so happened to be a website.
Co-founded by Simmons and essayist Chuck Klosterman, it launched with its own burgeoning podcasting network, and a collection of established and up-and-coming cultural voices. Named after sports writer Grantland Rice (who I know nothing about) Grantland (a money pit ESPN never really knew what to do with) ceased existing when Bill Simmons was fired from ESPN after publicly challenging, accusing, and otherwise feuding with NFL Commissioner Roger Goodall over the NFLs overall conduct and desire to sweep problematic elements of its existence under the rug.
Following his termination Simmons partnered up with HBO to launch The Ringer, a less intellectual version of Grantland, featuring articles specifically designed to be read on your phone while on the toile. The Ringer also launched with a podcast network that saw many former Grantland employees follow their old leader to his new endeavor.
In addition to The Ringer, Simmons’s partnership with HBO included the launch of his televised talk show Any Given Wednesday. This was not Simmons’s first televised appearance, as part of what made his battles with Goodell so public and potentially damaging to ESPN and their relationship with the NFL was his presence on ESPN’s various basketball broadcasts and surrounding shows, as well as his role in co-creating and producing ESPN’s critically acclaimed 30 for 30 documentary series. At the time of his termination he was more than a funny writer with a large following, he was a breakthrough new media content creator, and that gave him the leverage to pick a fight with the most popular sports league in America and still land on his feet.
If you’re wondering how he’s responsible for me being on Substack, well, The Press Box is a Ringer podcast that focuses on the media side of media and sports. It moves in and out of politics and current events while interviewing various writers, sportscasters and other news-people, and is hosted by Bryan Curtis and Dave Shoemaker.
Dave is also known as “The Masked Man”, a nom de plume he used while writing the Dead Wrestler of the Week articles for Deadspin (written at a moment where it seemed like once a week professional wrestler was dying before their time), which got him hired by Bill Simmons to write about professional wrestling and host a podcast for Grantland and then The Ringer.
I started listening to The Press Box because there was a while where I was voraciously consuming tons of Grantland and then Ringer podcasts, and as I particularly enjoyed Dave’s perspectives on professional wrestling, I was very excited for The Press Box, which as stated features various media personalities, some of whom have, you guessed it, Substack accounts.
So the road map goes Simmons -> Shoemaker -> Substack.
And really, I know I said it was Simmons’s fault you’re reading this, but that’s not entirely accurate. You see, it’s really professional wrestling’s fault.
Now some of you might be thinking, “I knew it, I knew this would come down to wrestling,” and you’d be right, but not in the way you think. You see…
Bill Simmons entered my life in the summer of 2005 when I saw The Vengeance Scale in an issue of Maxim Magazine. This was one of Simmons’s first pieces that broke into the larger mainstream, and while The Vengeance Scale has grown to mammoth size, at first it was a 1-10 scale of degrees of vengeance based on sports and pop culture. The scale landed with me because I enjoy the concept of vengeance as a whole, but more so it included several notable pro wrestling references that told me Simmons was also a wrestling nerd.
I’d seen the article and thought it was funny, but it wasn’t until a friend of mine saw it and mentioned it to me, that Bill Simmons started taking up more space in my life. This buddy and I had grown up together and shared a love of pro wrestling, but as we got into our earlier 20s, he and another friend started to get back into pro sports. While I’d been a basketball, baseball, and hockey fan in middle school, I’d fallen off to a large degree in high school.
Part of me falling off was me trying to cultivate an outsider image for myself and pointedly not enjoying the things the “preppy dickheads” I went to high school with liked, but I also hadn’t had cable since I was 16, so there was some limited access to the same volume of sports content. But since two of my closest friends (who I also played Dungeons and Dragons and LARPed –Live Action Role Playing- with) were getting back into it, fuck it, that meant so was I.
And Bill Simmons helped me do that.
His writing helped me reacclimatize myself and grow as a fan, and he helped me think about sports differently and in a larger social and pop cultural context. The way he engaged with the topics he talked about, from movies to sports, resonated with the way I thought about and engaged with pop culture as a whole. It was more than that though, the way he wrote, a sort of ADD infused, reference and context laden, jokey nerd ramble that strove to say something thoughtful, and sometimes sincere, while embracing “low art”, showed me how I could better communicate.
I don’t just mean in terms of writing, or providing a template or style to ape, I mean Bill Simmons showed me through his work how I could better “pretend to be normal”.
Some of you might be reading his and thinking “Wait, a jokey sports writer taught you how to mask your socialization issues?” and yes, yes that’s exactly what happened.
First, learning about sports, and being the compulsive nerd that I am, getting super into the things I enjoy, meant that when I started watching a lot of basketball and football, I also started reading a whole lot about both sports. This meant that at house parties I could talk to “the normies” about those topics, history, stats, rosters, and all sorts of other stuff, not just movies they probably didn’t know a bunch about, or hope they also were into comics.
But being able to talk about sports, and also say funny and interesting things (many of which were concepts stolen from Simmons) while making small talk with customers at the video store I worked at (combined with a few years of having to walk up to people on the sales floor and try to sell things to them while they were browsing), helped me to figure out how to have innocuous small talk in general.
Here’s the thing, when all your friends are people you’ve known for years and years, who you share tons of specific niche interests with you, and you only generally socialize with other nerds and weirdos of a similar ilk, you learn a very different mode and style of conversation. Talking to other nerds is a process of sharing specific opinions, quoting esoteric facts to support your opinions, and then over-explaining the things you enjoy because in those circles knowledge as a reflection of dedication and passion is social currency, not likability or charm.
(In many ways it’s the same with die hard sports fans, but there were more layers of casual fandom and engagement with sports due to its mainstream dominance.)
To this day I struggle with prolonged small talk or general conversation that isn’t unfettered discourse about big topics, but I’ve figured out how to pretend to be a normal dude for about ten minutes at a time, and yes, that tends to give people the wrong impression of who I am… usually around the assumption that I actually have some chill, which lets face it, if you’re reading this, you know I in fact have no fucking chill whatsoever.
So yes, I had to learn how to execute performative small talk as to not just be a handsome weirdo in conventional social settings, and Bill Simmons was a huge part of that.
Simmons also showed me that I could do what he did, and to due to my own high opinion of… well… my own opinions… and wanting people to like me… writing entertaining bullshit on the internet is something I’ve wanted to do since I started reading entertaining bullshit on the internet.
And this goes back, once again, to professional wrestling.
The first things I read on the internet were all wrestling related. In the late 90s as wrestling climbed to its cultural peak, and my wrestling friend and I both got the internet, we went all in on reading about wrestling. This included comedy pieces written by people doing a much less successful version of what Simmons would make his name doing just a few years later.
Wrestling writing in the early days of the internet paralleled what would become Internet Culture. The first time I encountered the idea of spoilers was in coverage of live-to-tape wrestling cards. Lists/listicles, think pieces, recaps, and live blogging/tweeting all occurred in the wrestling internet of the late 90s. Having opinions, and having been told that I was a good writer (and smart!) by teachers and friends (hence my stated high opinion of my opinions), I of course wanted to write for the sites that I enjoyed the most, and over a decade later I shared that same desire but for Grantland.
Of course that didn’t end up happening, and it wouldn’t have happened even if Grantland endured. When I made the choice to pursue writing as a career and my sole field of study when I went back to college in my late 20s, I also didn’t take any journalism or communications classes that would have set me on the magazine/internet/etc. writing path. So instead of trying to become something I wasn’t technically equipped to do, started a blog.
I wrote a few good things, and I wrote a few flat things, but I got some solid practice in. Then when The Ringer launched Facebook groups for their various podcasts, I had a chance to get some eyes on my written opinions from people that I didn’t already know.
At that time I was also logging a lot of time on my own Facebook feed, usually complaining about the shortcomings of things my friends liked, but when I had a chance to entertain strangers, I went all in.
Those Facebook groups, which I gradually left one at a time until just recently leaving my last and favorite of them all, provided a chance to go all in talking about movies, books, and TV, including a lot of conversation about Game of Thrones (in fact, if you google my name you’ll find one of my posts about the end of GoT that a friend copied with my permission to post in another place) and the MCU.
These groups, combined with my feed, gave me a chance to build my voice, find people to challenge my opinions, and opportunities to engage with perspectives that could compliment my own. It was a chance for me to entertain people by writing entertaining bullshit on the internet, and it worked!
In the years I was doing that, I was also developing the other side of my writing career, the one that actually pays me. But in that time there were many weeks where I spent more time critiquing the intellectual dishonesty of the MCU’s practice of making two hour long movie trailers for their next project and calling them movies than I did doing the work my clients had hired me for.
(This has nothing to do with depression or anxiety or any other mental health issues that might compel someone to make human contact and be appreciated and validated via social media… No, nothing to do with that, at all…)
I’ve been a professional writer (someone who is paid for their written words) since 2011, and now, ten years in, I’ve decided that those long ass opinion pieces about art and politics could be better served as essays, and since my words are proven to be worth money, and if I’m going to fuck around and write this stuff instead of doing my job anyway, I should probably monetize it.
Which is what Bill Simmons did.
So here we are.
-Back Matter-
Max, seriously, why would anyone want to pay you to read about the things you hate?
Good question. I have a literature degree, I’ve seen a few thousand movies, as stated I’m already a professional writer, and I’ve spent countless hours/days/years of my life studying the craft of story, the power and form of the written word, and I have a fairly well developed sense of humor, so I’m not just some guy shouting context free tirades into cyberspace.
Aren’t these fake QnA Back Matter pieces just you biting Simmons’s Mailbag?
No, it’s a play on making fun and enjoyable FAQs like the one I did for my work site, and that I’ve seen some of my work friends do for theirs. The Simmons Mail Bag was him taking actual questions from his readers and answering them, these are all hypothetical questions I am assuming a read may have.
Totally different.
So this really isn’t another stolen bit?
It’s also an homage to comics letter columns, and a means for me to recognize there are questions within these pieces that are tangential but not critical that I still want to address.
Really?
Okay, yes, this kind of cascade of answers/really? follow up questions thing is me stealing a bit.
So how big of a sports fan were you?
So in the mid 00s I watched parts of the NBA Finals in the back offices at different Blockbusters, broke the rules by putting various NFL games on the store TV, and lost a $20 bet to a teenaged customer when the Celtics beat the Lakers in the finals one year.
I got into fantasy football as a natural extension of my pedantic obsessions with things I enjoy, won my league one year, finished second another year, and made the playoffs every year I played except for my first and last seasons. I really fell in love with football for a goos solid decade, and then as the NFL continued to show just how malevolent an organization it was, it just stopped being something I could enjoy with any kind of passion or dedication.
As my desire to follow sports diminished so did my interest in Simmons’s podcast (he’s stopped writing regularly before his termination), especially as he really did lose his edge and become a rich white man (Simmons has some issues, but he also has taken a public stand on a lot of good things, I just don’t have the energy or interest to spend on him anymore).
Hold on, were you a Brady Era Patriots fan because of Simmons?
Actually, no. I dipped in an out of following football during my late teens and earlier 20s before going all-in and when your team was the pre-Russell Wilson era Seahawks, sometimes you just wanted to watch a winner.
Simmons being a huge Pats homer was just a happy coincidence, because seriously, Tom Brady is really good at football, and was fun to watch.
Fun fact, the 05-06 NFL season was the first season I followed as a serious football fan, so it was kind of amazing getting to watch the Seahawks go to (and then shit the bed in) their very first Super Bowl.
So you ‘found’ Simmons because of his wrestling references, then you found a wrestling writer you like because of Simmons, and that writer led you to this platform? So this really is a convoluted wrestling mess?
Oh, it’s even better than that.
I stopped watching wrestling regularly in late 2003/early 2004 because of work and a loss of interest on my part (and my buddy’s, though we did go to Wrestlemania 19 in 2003 when it was held here in Seattle). I caught bits and pieces over the years, but I was out on it, but generally speaking I was all the way out by 2005.
Then, CM Punk happened (that’s a whole article unto itself, he’s Stone Cold Steve Austin for people with depression), and wrestling got (kind of) cool again in the summer of 2011 (with certain crowds of lapsed fans).
Simmons, an admitted lifelong fan, started talking about it more, having wrestlers on his podcast, and that was when Dave Shoemaker got brought on to write about and talk about wrestling for Grantland.
Rest assured there’s going to be an article soon talking about my return to wrestling, but thanks to Grantland I started watching again in the beginning of 2013, and that led to an idea for a novel that’s maybe a novella, and certainly on a very far back-burner, and me taking a scholarly deep dive into wrestling that was more intense (and academically minded) than my original stretch as a fan.
So what’s that podcast/Facebook group you just left?
The podcast, The Watch (formerly the Hollywood Prospectus when it was part of Grantland before it got re-launched with The Ringer), is a twice-weekly pop culture criticism hosted by TV critic turned TV writer Andy Greenwald (Briarpatch) and Ringer Editor Chris Ryan. They are lifelong friends, former writers for Spin (the worst music magazine), and their tastes lean towards HBO prestige television. Their tastes play off each other well, and are very much grown up middle/upper middle class Gen-X college radio types.
Andy Greenwald, who was Grantland’s TV critic, has the same relentless critical eye that I do, and while my tastes don’t always intertwine with his, my critical sensibilities do. Of the two Chris Ryan is the everyman, but if the everyman’s favorite band was The Afghan Wigs and was super into Premier League Soccer.
The Facebook group initially attracted people with sensibilities similar to the hosts, who wanted to gather to have similar types of conversations as the ones on the podcast.
I found my time there deeply enjoyable, and have made some wonderful friendships through my participation there.
Wow, so the extended Bill Simmons universe really changed your life didn’t it?
You think that’s something, wait until I tell you about Brian Michael Bendis.
Why I've Taken My Talents to Substack
Thanks for sharing this! Glad we connected along the way.