Videos by OutKick
Every online writer starts somewhere.
For me, I started writing online in 2004 when I moved to the U.S. Virgin Islands and discovered that DirecTV’s NFL Sunday Ticket was not available in my new home.
I was upset.
So I did what every reasonable person would do — I embarked upon a fifty day pudding strike to demand that the Virgin Islands receive the NFL Sunday Ticket. During that time I ate only pudding. My pudding strike became a viral sensation before anyone knew what being viral meant. It was everywhere. You can probably track down your own articles via a Google search, but here’s a Pulitzer worthy interview and column on my pudding strike from the Orlando Sentinel.
After the pudding strike ended — we succeeded in snagging a pirated feed of the NFL Sunday Ticket from Puerto Rico — I decided I’d enjoyed writing humorous pieces online and wanted to do more of it.
But, go figure, there wasn’t much of a market for pudding strikers. (Although I do submit that my daily pudding diary was some of the finest pudding related literature to ever be created. Online, anyway).
So I decided to start a humor website with several buddies, the funniest guys I knew from high school, college, and law school. We were an interesting lot of characters, a lawyer in the Virgin Islands, a Subaru salesman who used to play basketball at Colorado, Josh Townsend, a pro basketball player overseas, my buddy D.J. Harrison, the 27, a Florida lawyer who already hated big firm life, and the man who built our website and made everything click, a PhD student from Maryland named Chris Shaw who I met in freshman year of college.
Our idea was pretty simple — be funny every day for people like us who sat in offices looking for entertaining things on the Internet.
In early 2005 the sites that did that best were few and far between. There was CollegeHumor.com, Fark.com, and a few other decent-sized sites that we all visited for periodic daily entertainment when we were supposed to be working.
There were no popular sports blogs and the idea of “social media” was foreign to us. Facebook was just beginning to spread across college campuses, Twitter was still a couple of years away, the most entertaining content mostly spread via email.
We had no idea what we were doing.
Yet, we brainstormed via email for weeks searching for the right name that would encaspsulate exactly what we wanted to do.
We settled on DeadlyHippos.com for two reasons: 1. it was available and 2. because I was entranced with the idea that hippos, who are considered so cuddly, are actually one of the most ferocious animals on the planet.
Our tagline at the top of the new site?
“The only website that combines biting social commentary with cutting-edge hippopotamus research.”
On the day we launched, in January of 2005, we sent out emails to everyone we knew, come check out new site!
A couple of hundred visitors arrived.
That would be the largest daily readership we’d see for several months.
Yet we kept grinding.
We all wrote at DeadlyHippos.com for two years before writing a book, Man: The Book, that was so ridiculous and absurd it was the perfect capstone for the era. (In a perfect ending, Man:The Book was a bestseller in England, not the United States.)
DeadlyHippos.com was a complete and total labor of love because we made no money off the site — in fact we actually lost money in hosting costs.
But I found out something important, I loved every minute of it. We bounced ideas off each other via email, shared drafts, ridiculed each other, praised really funny lines. Those emails were the most exciting parts of my workday as a young associate grinding away on the billable hour. And some of our columns were dropdead hysterical, bouncing all over the Internet’s most popular sites back in the day. Of course, some weren’t very funny at all, the execution didn’t work right, the premise was sound but the humor didn’t translate on the page. There are any number of ways an Internet article can give up the digital ghost.
Along the way we all learned an important lesson when it came to writing for any segment of the public, even the small audience we had — if you can string together basehits — and try to minimize your strikeouts — the doubles, the triples, and the homeruns will come.
And so will the readers.
I get asked for advice a great deal by young writers these days, people graduating from school with hopes of writing about sports but no real clue what the future holds, kids still in high school. They all want to know how to do it. How do you turn a passion for sports — something that many of us share — into a living?
The simple answer is there isn’t any one path, we’re all different. Hell, if the NFL Sunday Ticket existed in the Virgin Islands, who knows what I’d be doing for a living now?
I doubt the pudding strike will work for you too.
But my consistent advice to young writers is threefold: 1. be smart 2. be original 3. be funny.
Then work your ass off.
I wrote for CBS Sports — CBS, a multi-billion dollar company! — for over a year for free.
Three columns a week hammered out while I was practicing law full time.
Not one dollar in return for the work.
Then I wrote for another year for CBS for $100 a week, $33 a column.
After three full years of writing online I’d made a total of about $7,000, barely two grand a year. Lots of y’all work full time jobs while you write in your spare time so you know the grind. You’re tired, you’re sick, what you’re writing doesn’t feel perfect, there’s no money in it anyway, no one is reading — those are all the demons that you have to battle inside your own head.
Writing is hard.
Suck it up.
I haven’t linked these old columns before, but many of you have asked for them. (In fact, one of my great disappointments about writing online is there’s no single respository for the seven or eight million words I’ve written online in the past nine years). But then tonight a reader emailed me a great gift, a link to a piece I’d written about attending my wife’s ten year high school reunion, one of my earliest online columns.
I’ve been reading the archives ever since.
This isn’t all the columns I ever wrote, but it’s a ton of them.
They’re fascinating to read nine years later because so many of them are so ridiculous. Was I really writing several thousand words on the 2005 televised movie, Spring Break Shark Attack?
Yes, yes, I was.
But that wasn’t all.
Far from it.
I was also writing on my allergies, my love for the video game The Oregon Trail, the time I wore a pink shirt to high school and was destroyed for doing so by my friends, missing white women on TV, 31 rules for enjoying an amusement park, and the aforementioned awkwardness of attending my wife’s ten year high school reunion.
From the official rules of wiffle ball to having a leg press feud with Pat Robertson, who claimed he could leg press half a ton, I wrote about everything and anything I thought might be entertaining. Including, I might add, the Napoleon Dynamite question on the Tennessee bar exam, racist dogs, and a letter to the producers of My Super Sweet 16 expressing dismay after they included a Super Sweet 18 party in the telecast.
I even wrote on serious issues, the growth of Southern mega churches that even had fireworks at the pulpit, the legacy of black quarterbacks in our generation, and Survivor’s decision to break all of its teams into four distinct racial categories.
Also, the most serious issue of all, the 50 most annoying Super Bowl party guests.
Along the way I filed away what worked and came back to the Internet writing laboratory again and again.
I was grinding away, loving what I was doing, but to what end? How could I turn this into a living and get readers coming back again and again?
Simple, by getting better, figuring out what writing worked on the Internet, both sports and non-sports. It took years. Hell, I’m still learning every day what works and what doesn’t.
You probably have to write a few hundred thousand Internet words to find out what tone works best for you. My voice was conversational, I wanted it to sound exactly like we were talking at a bar. As I’ve moved to radio one of the compliments I enjoy the most — aside from “your gay” — is that I write like I talk, that people can read my column and hear my voice when they do it.
The same is true of my Tweets now.
One of my favorite series of columns to reread was about a trip to Cincinnati I took with college friends. We went to watch the A-10 basketball tournament back in March of 2005. Over five consecutive days I wrote about our trip to the city. We were just fans, but the passion and fun of our experience translated much better than a stale game recap. I’d discovered people liked stories about the events surrounding a game much more than they sometimes liked actual games stories. This wasn’t rocket science, but in 2005, it was knowledge that most didn’t have.
I filed that knowledge away and it was the genesis of my decision to spend the entire 2006 season on the road in the Southeastern Conference.
Yep, “Dixieland Delight,” was born at the 2005 A-10 basketball tournament.
I wasn’t writing with any great access — I had none — or spectacularly unique ideas, I was just writing about my life — ridiculing myself along the way for getting fat or for my career as the world’s worst student basketball manager — hopefully in a funny enough way to keep people coming back for more. Thankfully, lots of you have. In fact, some of you guys and gals have been reading for nine years now. You’ve probably read me through school and on to marriage and, maybe even, the birth of your own kids. I’m flattered by y’all most of all, because you’ve grown with me.
Are all of these columns perfect? Ha, no way. Do some jokes fall flat and some entire column ideas not work, sure — no Internet trainee is perfect — but do I think many of you will detect a budding gay Muslim in training?
I’ve written millions of words on the Internet at CBS Sports, Deadspin, FanHouse, Outkick the Coverage — and now Fox Sports.
But every online writer starts somewhere.
For me, that place was DeadlyHippos.com, still the only website that ever combined cutting social commentary with cutting-edge hippopotamus research.
If you’re nervous about getting started writing, dive into my old columns that I wrote alongside a few buddies with an initial audience of zero. I think you’ll probably find out pretty quickly that there’s quite a bit of hope for you too.
Appreciate y’all indulging me and thanks as always for reading and sharing Outkick.
Nine years after I wrote that first DeadlyHippos.com column, I really can’t imagine doing anything more fun.
Thanks to you guys, I don’t have to.