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Meet Alicia Jessop of Ruling Sports in Santa Monica

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Today we’d like to introduce you to Alicia Jessop.

Thanks for sharing your story with us Alicia. So, let’s start at the beginning and we can move on from there.
Growing up in Denver, CO the only child of a sport loving father, sport quickly became a central focus of my life. By the time I was 14-years-old, I was competing in–and winning–fantasy hockey leagues filled with adults.

A natural storyteller, writing was something I excelled at. With sports such a central piece of my life, as a high school freshman I decided I wanted to be a sports writer. In 1999–like today–there weren’t many female sportswriters. So, when my high school gave students a day off of school to shadow someone in a job we wanted, I spent the day with a male sports editor of the now defunct Rocky Mountain News. Some 20-years later, all I now remember about that day was the man giving me every reason why I shouldn’t become a sportswriter: long hours, difficult assignments, little pay. I walked out of the downtown Denver office that day and when my mom picked me up, I distinctly remember telling her, “Well, I guess I’m going to law school.”

After graduating with a degree in Economics from the Colorado School of Mines, I went straight to law school at Chapman University in Orange, CA. Giving up–or so I thought–on becoming a sports writer, I decided I was going to become an entertainment lawyer. In law school, I worked for the Screen Actors Guild and Warner/Chappell Music, where I learned about representing and advocating for the rights of artists and creators. I graduated from law school in 2009, at the start of the economic recession. Long story short, when the recession hit creating stopped and there were few jobs for newly minted attorneys in the entertainment industry. I paid for law school on my own–and thus, had student loan debts coming due–so I couldn’t take a low-paying job at an agency to break into the industry. I needed a job–and a well-paying one at that. So, I became a corporate litigator at a mid-sized firm in Orange County representing Fortune 500 companies in their contractual matters.

As new attorneys across the country fight to find full-time employment, I was grateful for a job that allowed me to live blocks from the beach in Corona del Mar and provided health insurance and a 401k. But, I was dying a slow death. The job didn’t provide the outlet for creativity and collaboration that I subconsciously craved. I knew I needed to make a change and with the economy still sputtering, I knew that if I wanted a new career, it was going to have to be built with my own hands.

I did some soul searching and realized what really motivates me is storytelling. I have always loved learning where people come from, why they do what they do and making connections between events that on the surface seem totally random, but with some thought, come together to tell a story. I had a unique education as an attorney that I wanted to continue utilizing but in a different way. Putting these pieces together, I decided to start what was initially a sports law website but has emerged into a sport business media company, Ruling Sports.

I started Ruling Sports on July 1, 2011. I caught some luck when the NBA locked out its players the same day and I was positioned as a sport law expert to discuss and analyze the news. In the months that followed, I would sign a broadcasting agent and obtain my first professional writing position with Forbes. In the years that have followed, I have been credentialed for events like the Super Bowl, NBA Finals, Final Four and more. I have written for publications like The Huffington Post, CNBC and SI.com, The Washington Post and am currently under contract as a writer for The Athletic. In 2013, I left the full-time practice of law to enter academia as a professor at the University of Miami. Presently, I am a tenure-track professor at Pepperdine University, where I teach Sport Law and Sport Marketing.

We’re always bombarded by how great it is to pursue your passion, etc – but we’ve spoken with enough people to know that it’s not always easy. Overall, would you say things have been easy for you?
I count myself very fortunate that every day I get to wake up and pursue a career I am passionate about. With no formal journalistic training, I do not take it for granted that I have been a professional sports writer for nearly ten-years who has covered some of the biggest sporting events in the world. Overall, my path has been very humbling but open and giving. I count myself very lucky that I have obtained the opportunities I have in a relatively short timeline.

I attribute this to several things. One: I wake up every single day ready to work. I have devoted my life to my craft and spend hours each day writing, reading and interviewing. I believe my hard work has paid off in the opportunities I have received. I also attribute the opportunities I have received to the great people my path has crossed. Being a woman in a male-dominated industry is never easy. There have been times in my career where it has been made abundantly clear to me by others–whether intentionally or not–that I am a minority. However, those moments pale in comparison to the people who have opened doors for me and supported my career. One thing that has made my road smoother is the strong relationships I have made with sport industry leaders, both male and female.

One of the greatest struggles I have faced in my writing career is fighting to tell the stories I think matter. The stories that interest me the most center around the human condition and highlighting individuals overcoming adversity. Early in my career, I was told by an editor that people don’t care about these stories and they don’t matter. In that moment, I could’ve given up and begun writing how most journalists at the time were, which was writing in a way that focused on the negative. Ultimately, I lost my job at that publication because I did not conform to this method of storytelling. I was without a contract for two years, but in my heart, I knew there was a place for stories showcasing the potential of people and corporations. In June 2019, my belief was confirmed when the former Editor in Chief of Sports Illustrated called me to say that while in 2011, when I started writing, there may not have been a natural place for my style of writing, the landscape had changed. This man, Paul Fichtenbaum, would ultimately offer me a position with The Athletic.

We’d love to hear more about your business.
Ruling Sports is a sport media platform that covers the business of sports. Over the last eight years, I have established myself as a thought leader in identifying and dissecting emerging trends in the sport industry. I seek to provide readers with timely information that takes them in-depth into how teams, leagues and athletes prepare to win and obtain championship-level success. What sets me apart from others is my constant desire to go in-depth into any story that I cover. Most journalists tell readers about the who, what, where and when. This is good, and I seek to do the same, but what sets me apart is my dedication to the “why” of a story. I am most proud of my constant commitment to getting to the root and reason for a story.

What were you like growing up?
My entire life has been marked by my fascination for life and interest in the things around me. There are some people who pick one thing in this world to be fascinated by and become great that one thing. That is not me. My dad often says I have “rabbit feet”–I am constantly jumping from one thing to the next.

As a kid, I swam, golfed, danced, played tennis and danced. I played the piano, recorder, handbells and had a brief stint with the trumpet. I wrote short stories, turned my grandparents’ kitchen into a science lab of sorts where I’d mix different ingredients to see what would form, and built websites for fun. If I had to sum me up then–and now–I have always been cautiously curious. I never dive “all-in” to the wacky ideas I have–in my heart, I am very entrepreneurial. Rather, I slowly build projects that come about first because I am curious about something. Then, I work steadily to learn all I can about that thing and grow my involvement in it until I achieve what I want from it.

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