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Thank God for the Internet

SUCCESS STORY.

Conrad Engstrom
Gladwellian Success Scholarly Magazine
12 min readMay 18, 2016

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By Conrad Engstrom | Journalism Major

Four-year-old Bill Simmons did not realize the importance of what his father did when he cashed an income tax refund to buy Boston Celtics season tickets behind the visitors’ bench in the summer of 1973. Being the only child at the time with his father teaching at an all-girls boarding school while bar-tending at night and studying law school, when the tax refund came in Simmons’ father wanted something for himself. When Simmons’ mom shot down the idea of his father getting a motorcycle, the Celtics season tickets would do just fine. For four dollars a ticket, Bill Simmons would begin to go to Boston Celtics and fall in love with basketball.

Now Simmons is one of the most well-known sports personalities and Boston sports fans today, and if his father would have bought a motorcycle instead of Celtics tickets it probably would have never happened. Not long after the Simmons family became Celtics season ticket holders, Bill’s parents got a divorce (Simmons). This nine-year-old will soon become one of more popular columnist at ESPN. Bill Simmons used special opportunities, worked hard at his writing craft and the internet got popular at just the right time to tip things in his direction to become a multi-million dollar sports columnist.

Bill Simmons used special opportunities, worked hard at his writing craft and the internet got popular at just the right time to tip things in his direction to become a multi-million dollar sports columnist.

Special opportunities play a big role for any successful person in life. Malcolm Gladwell writes in his book Outliers that you don’t become successful off talent alone. Gladwell sites opportunity and taking advantage of opportunities as huge factors in making someone successful. He writes about how hockey players born in January have a better opportunity of becoming successful hockey players because the January first cutoff date for the leagues. Therefore those born earlier in the year are older, stronger and therefore get better training and coaching than those born at the end of the year. Not saying that someone born in July cannot become successful at hockey, that person would just be an outlier (Gladwell).

Simmons is no different. He wrote a 700-page book about basketball called The Book of Basketball. In the book he tells the story of the four dollar tickets his father bought to become a season ticket holder of the Boston Celtics. Let’s say for instance Bill’s father buys something else with the tax refund money. Bill probably doesn’t become as passionate about the Boston Celtics or basketball for that matter. He wouldn’t spend nights at Boston Garden with his dad watching the Celtics win championships. He probably doesn’t start writing columns and he definitely will not writing a 700-page book about basketball that ranks the best 96 players in NBA history.

The Simmons’ family are not the only people to have own season tickets to their local professional sports team. More went into Simmons becoming wildly successful than just going to Boston Celtics games as a kid, most of them he did not remember. However, the fact that his dad still has those same tickets gave Bill more opportunities to fall in love with sports than the average kid.

Simmons graduated from The College of Holy Cross with a B.A. in political science. As an undergraduate, Simmons started his writing career. He had a column in The Crusader which was the Holy Cross school’s newspaper at the time. His column was called The Ramblings and he kept that column for all four years as an undergraduate student and later became the sports editor of The Crusader.

Simmons liked writing his column and thought of it as something he wanted to do moving forward. After obtaining his master’s degree in journalism at Boston University, Simmons worked at the Boston Herald as a high school sports reporting, mostly answering phone calls and reporting scores. He thought he could work his way up the ladder to eventually getting a column with the Herald.

His work shifted more to writing for the Boston Phoenix which was a weekly paper in Boston at the time. However, with the landscape of everything that was going on at the Boston Herald, Simmons was unsure where he would fit in getting a column. In March of 1996, Simmons saw himself in a rut where he knew if he did not change something he was not going to become what he wanted. He was not writing as much as he wanted, the Boston Phoenix changed editors and it seemed like the new editor did not want sports, so with no internet yet Simmons did not have his voice.

He left the Boston Herald to become a freelance writer for the Boston Phoenix and Boston Magazine. Three months passed and Simmons only got one story to write. Simmons described his troubles in a podcast he did in April of 2015, “I’m 26-years-old and my writing career is going down in flames so I start bar tending because I need money and I was too old to start asking my mom for money,” (Simmons).

Simmons definitely hit his low point here. He’s been searching for a writing career and all the special opportunities have not gone his way at the moment. However, he seems aware about it at this moment in his life because he quits writing and journalism altogether to bar tend. Little did he know about this thing called the internet that was just about to become popular.

Gladwell, before he wrote his book Outliers on success, wrote a book called The Tipping Point: How Little Things Make a Big Difference. Gladwell in this book researched fads and how things become popular, and why.

One example Gladwell gives in his book The Tipping Point about why things catch on is the stickiness factor. Things become popular because the trend sticks with people in a way that they remember it and want more of it. Gladwell explains through an example of the kid television shows Sesame Street and Blue’s Clues and how, since their product was sticky to kids that watched their show, they became popular (Gladwell).

Digital City Boston was the AOL digital newspaper on the internet at the time and Simmons saw an opportunity. When he saw that they had someone with the title Movie Guy that wrote movie reviews and had his own page, Simmons thought to himself he could be Boston’s sports guy and finally complete his goal of getting a sports column; only, it would be digital.

“I just started badgering the editor of the site,” Simmons said on the same podcast referenced earlier. “And after a couple months it looked like it might happen.”

It happened. Partly because of a special opportunity, partly because of the internet gaining momentum at just the right time, but mostly Simmons just willed his way to getting the job by never letting his dream go away. The spring of 1997, a full year had passed since it looked like Simmons’ writing career was down the toilet, and now it looks like there might be life if this digital website can get up and running for him. In May, the site was ready and Simmons had his first sports column since his days at Holy Cross.

Simmons did not write like the traditional newspaper columnist on the AOL website. He wrote from a fan’s perspective, answered readers’ emails in what he called mailbags, did running diaries with time stamps of information and also did NFL picks. Not writing like a newspaper columnist worked to Simmons’ advantage because he was not writing for a print newspaper, he was writing online and it was new to mostly everyone.

Simmons would pump out three or four columns a week on several sports and pop culture topics for the next two and half years. However, with the website being AOL it was impossible for his friends to see his columns unless he forwarded them to them via email. This started a big email chain of Simmons columns. So now Simmons has his column on the AOL site that people on AOL can see and is also sending them out to his friends who are sending him them out to their friends and so on. Imagine the leg up Simmons had on the competition of trying to get noticed when his columns are being sent around the internet constantly instead of being stuck in a newspaper where it cannot travel as fast. Simmons knew he had written a great column when the email chain would get all the way back to him with someone writing, “Hey check out this funny column this Sports Guy wrote.” And him being like, “That’s my piece!” (Simmons).

Simmons had that stickiness factor that Gladwell sited in his book The Tipping Point. Simmons started a trend of writing on the internet and blogging on the internet. If it were not for the internet or Digital City Boston at AOL giving him a chance, he would probably never have gotten his chance to become sticky. He used his column to find out what failed and what worked and would use the feedback he got from his fans and friends to improve his column and his writing.

Gladwell in Outliers states that it takes roughly 10,000 hours for someone to become an expert at something. For Simmons it’s no secret that writing three to four columns a week, most of them roughly 4,000 words or longer. Simmons reached or got close to 10000 hours of practice on his writing craft if you count the freelance work he was doing also (Gladwell).

Simmons’ opportunities were not over yet. In 2000, ESPN launched its page two website in which they wanted both sports and pop culture to be written. Well guess who has already been writing about sports on pop culture three to four a week on a website for almost three years when ESPN launched page two?

It took ESPN longer than he expected — in fact Simmons almost gave up writing entirely after he though ESPN was not even going to offer him a chance to write on page two— but Simmons got his chance to write a column for a national audience at ESPN. After a few test runs, Simmons got a job offer at ESPN to write for page two and took it.

Simmons became one of the first writers to have a national column and have it be successful. He took a break from his column at ESPN to write for Jimmy Kimmel and his show (Simmons). Simmons felt burned out from writing 10,000 words a week for the past five years and felt like he needed a break, but his break only lasted a year before he returned to his column at ESPN.

In Outliers, Gladwell writes that another key to successful people is the feeling of their work being meaningful. For Simmons, his meaningful work was his column at ESPN. The proof is in the all the work he had to do to get to ESPN. He almost gave up twice but each time came right back to writing columns because that’s who Simmons was and that felt like meaningful work to him.

Simmons led the blogging cult and made writing your opinions on the internet popular. Sports Illustrated did a story on Simmons in 2006 talking about Simmons’ process and the effect the internet has had on sports writing (Ballard). How did Simmons’ columns become so popular when he did not even go to most of the games he writes about? How did Simmons even create a national column that became successful and not dull and stupid? A column that actually had a following and had people talking and waiting for the next one? It’s because Simmons wanted it to be successful. He believed in his writing style. He worked hard, writing on this new thing called the internet that not a lot of people knew how to use properly. He had talent and took advantage of opportunities, including using Celtics season tickets that his dad still has.

Compare Bill Simmons to someone like ESPN personality Bomani Jones. He did a Ted Talk on “Freedom of Structure” in which he states in the opening that, “if you do what you’re supposed to do you can pretty much get away with whatever you want to do.” Unlike Simmons, Jones did not really know what he wanted and did not push for a column that Simmons or push to be on ESPN it just kind of happened for Jones.

Instead, Jones worked for a PhD in economics and failed. However, Jones said not getting the PhD turned out to be okay with him. “My work habits did improve I learned a lot of economics, my thought process was a whole lot more structured and I didn’t have to do calculus anymore,” Jones said. “And I’ll take not doing calculus over having a PhD any day (TEDxTalk).”

Jones made his own advantages, became a better writer and became successful because of it.

“My work habits did improve I learned a lot of economics, my thought process was a whole lot more structured and I didn’t have to do calculus anymore, and I’ll take not doing calculus over having a PhD any day” — Bomani Jones, ESPN personality

Simmons had his own “Freedom of Structure” way of doing things with how he wrote differently on the web than people were in the newspaper that made his work stand out and eventually got him to ESPN, to make his own website Grantland, to now after leaving ESPN starting his own little thing with HBO. Simmons had his work habits improve when he was pumping out three to four columns a week, working on his writing craft and getting his 10000 hours in to be a great columnist. He believed in his work and did not like it when his editors would take out jokes. Simmons’ freedom of structure got him to be a multi-million dollar sports personality and it was not by accident. From special opportunities like the Celtics season tickets and ESPN page two launching. To the internet tipping at the right time so Simmons could get a column in the first place where he could write and write a lot. Gladwell said it best when he wrote in Outliers, “Achievement is talent plus preparation.” And that’s Simmons, thanks to the internet.

Works Cited:

Ballard, Chris. “Writing Up A Storm.” SI.com. N.p., 27 Mar. 2006. Web. 11 March 2016.

Gladwell, Malcolm. Outliers: The Story of Success. New York: Little Brown and Company, 2008. Print

— -. Tipping Point: How little Things Can Make a Big Difference. New York: Little, Brown and Company, 2000. Print.

Simmons, Bill. The Book of Basketball. New York: Ballantine Books, 2009. Print

— -. “Welcome to Grantland.” Grantland. N.p., 11 June 2011. Web. 11 March 2016.

— -. “The B.S. Report with Bill Simmons.” Host Bill Simmons. BS Report — Wesley Morris. ESPN, 4 April 2015. Web. 6 May 2016.

TEDxTalks. “The Freedom of Structure | Bomani Jones | TEDxWestBrowardHigh.” YouTube. YouTube, 24 Mar. 2016. Web. 04 May 2016.

Photo by Taya Hillereod.

ABOUT THE AUTHOR:

Conrad Engstrom, a freshman from Maplewood, Minn., hopes to one day be a senior writer for Sports Illustrated. He plays on the Bethel University basketball team and is a sports reporter for the Bethel Clarion. Engstrom likes watching old NBA footage, cheesey-alfredo spaghetti sauce and making people laugh.

WHAT I’VE LEARNED:

Not every genius makes it.

If you are born in December and want to play a sport hockey should be your last choice.

Even when someone tells you you’re a good writer, you’re not.

Sometimes your success is out of your hands.

Is-ing and was-ing is disgusting.

When making something popular try and think what sticks, not what you think sticks. And if you don’t think context matters then you probably shouldn’t be in charge of anything.

Sometimes it’s the strip club gigs that make you good.

Usually when one suicide happens another one is near.

There are no real outliers. It’s just people taking advantage of opportunities. That’s called life.

Sometimes a great sports columnist needs to bar tend for a year before he feels like he truly fulfilled his dreams.

You can learn from your failures. The outcome might be negative, but your growth as a human is positive.

Even when you rarely show up on time and this is the fourth time you are having a professor this year you can still learn things about your writing and be better.

I loved reading about my hero and listening to his podcasts about how he became successful. When re-telling my hero’s story through Gladwell theories and scholarly research I found myself thinking and shaping my own success path. Who knows what kind of journalist I will be, but it’s fun to dream about it.

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Conrad Engstrom
Gladwellian Success Scholarly Magazine

future journalist despite my lack of spelling and grammar habits. bethel basketball