I Was Once A Writer

One man's journey into a content career.

What now feels like several lifetimes ago, I was in college.

I started out as a business major simply because I got into business school on a clerical error indicating I finished fifty-second in my high school graduating class of just under 1,000 students. In reality, I graduated in the fifty-second percent (closer to 502 than 52).

Seems like a big break, right?

I was kicked out of business school after one semester for achieving an impressively low .40 GPA. 

Not 4.0. Zero point four zero.

To keep a very long story short, suffice it to say after that first failed semester I went back home to Houston, Texas to live with my parents for a year in an effort to get my life together, and when I returned to school, I declared myself a journalism major for the sake of making it easy. Writing was always a personal strong suit, and something I very much enjoyed doing, so I figured journalism classes couldn’t be that difficult considering. I was correct.

A few years later, in 2010, I was set to graduate with a degree in journalism, but had absolutely no intention of becoming a journalist at some dying newspaper. No disrespect to journalists, but there aren’t too many real journalists remaining in this modern media hellscape anyway, and I doubt any of them are reading this. I did, however, want my first job to have something to do with writing.

A few weeks before graduation, after expressing my interest in writing while doing cocaine with an alumni of my fraternity who, unbeknownst to me, founded a virally popular college humor website, I accidentally landed my first job as a content creator with a whopping $22,000 annual salary. TFM.

I launched the written content offering for that website, wrote multiple columns every day for months, and eventually stumbled into the opportunity to write a book based on the popular humor brand. At 23 years old, I began writing that book. At 25 years old, I became a New York Times Bestselling Author the week “Total Frat Move” was released in 2013. Whoops!

From writing to podcasting…

Fast forward a few years, and my career evolved into podcasting when I decided it was time to explore other mediums beyond writing. I launched a Game of Thrones companion podcast titled “Oysters, Clams & Cockles” (henceforth referred to as “OCC”) in 2016 during season 6 of the HBO show, and quickly built a sizable listenership. OCC became a massive success, generating several hundred thousand downloads and upwards of $100,000 in advertising revenue by the end of our first season alone. 

I was hooked.

Podcasting became my life, and, as a result, writing faded into the background. I spent much of the next couple years recording at least seven hours of audio content per week. OCC continued to crush, I was also hosting a sports podcast, and, in 2017, I launched my self-titled comedy show “The Ross Bolen Podcast” (henceforth referred to as “RBP”) to ensure I had a place to discuss all the other things which interest me.

Then came 2019, when the company which employed me for the first eight years of my career became, despite my personal success, a failed venture from which I sadly had to walk away. But I was fortunate enough to leave with the IP for both OCC and RBP. So rather than go to work for another company which could leave my fate in the hands of higher-ups and result in disaster like the first time around, I decided to launch my own media startup and take the leap of self-employment with the pre-existing foundation of the aforementioned podcasts.

Bolen Media is born…

In 2019, Bolen Media was born of circumstance and an unwillingness to put my career in the hands of anyone else ever again.

Now, four years into self-employment, having recorded somewhere around 1,000 podcast episodes across several shows (600+ of RBP alone), I routinely find myself missing what got me into this content game in the first place. That, my friends, is what brings us here today.

Writing. I need a place to write, and you’re looking at it.

Since founding Bolen Media in 2019, my life has changed in too many ways to detail in one column. I survived a divorce and the pandemic at the same time, nearly died getting off antidepressants, started taking therapy really seriously, remarried and became a step dad, and, most recently, became a dad myself with the birth of my son. I have seen some shit, and now that my written work has a place to live, I’ll be publishing columns about said shit. You can expect writing on what I’ve learned from life, mental health, pop culture, sports, parenting and step-parenting, and whatever else strikes my fancy, frankly. As a 12-year veteran of the content game, I’ll definitely share some thoughts on modern media as well.

You can expect one free column per week, with the idea being that if I can write highly shareable stuff, perhaps my writing can serve as another potential thing through which Bolen Media’s audience can grow. If you subscribe, you’ll have access to one column per week that is exclusively for subscribers as well.

I appreciate you taking the time to read this today, hope you’ll share it with friends and family you think might enjoy it, encourage you to subscribe if you’re looking to read more from me, and look forward to hearing from you in the comments.

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