I recently profiled Matthew Goldberg, whose career started in sports journalism before he switched to business writing. Today, I bring you Jason Del Rey, whose career started as a breaking news and sports reporter at the Jersey Journal before he switched to business. Journalists like to say that three makes a trend, so I can’t officially declare that sports reporting makes a strong foundation for business writing. But based on the findings, it’s something worth watching.
After his sports stint, Jason worked at Inc., Ad Age and Recode, where he made a name for himself as an e-commerce expert. So, it’s no surprise that he wrote a book, the recently released “Winner Sells All.” It’s been described as “a riveting investigation of the no-holds-barred battle between Amazon and Walmart to become the king of commerce.”
I chatted with Jason about what led to his early career pivot, how his book came about and what’s next:
Dawn: Tell me about your new book.
Jason: I think of “Winner Sells All” as the inside story of the greatest business rivalry of our time: Amazon vs. Walmart. It’s also the deepest look, in my opinion, at Walmart’s battle to fight through the innovator’s dilemma that has turned so many titans of industry into has-beens.
Dawn: How did the idea come about?
Jason: I’ve covered both companies since 2013, so had developed great sourcing in and around both and knew them well. I also knew that while there have been some great books written about each, there hasn’t been one that explored all the ways their rivalry has influenced their strategies, offerings, and the way they run their companies. And all of that was fascinating to me.
Dawn: I hear from a lot of people who want to write books. What should they do?
Jason: Think long and hard about whether you are passionate enough about the idea to dedicate two to three years of your life to the project. It’s also wise to keep in mind that you might only make money from the book advance and not from the actual book sales, so don’t agree to an advance that you are dissatisfied with.
Dawn: Back to *your* book. What shocked you most about the battle for our wallets?
Jason: I always knew each company closely watched the other but still didn’t truly grasp how many of their strategies and initiatives were influenced by each other until reporting this book.
Dawn: Now, let’s go back in time. What got you interested in journalism?
Jason: I first wanted to be a sports anchor because I was obsessed with sports at a very young age, and watched ESPN’s SportsCenter religiously. I then dreamed of becoming a sports journalist because I loved reading Sports Illustrated and the sports section of the newspaper in middle school. Then in high school, a teacher encouraged me to get involved in the school newspaper, which I enjoyed. By college, I was committed to taking the few journalism classes my university offered, as well as interning during summers at my local newspaper. At that point, I had the journalism bug.
Dawn: What led you to business journalism?
Jason: I honestly fell into it. I took a business journalism class in graduate school and did very well, but when I graduated there were simply better business journalism opportunities than sports journalism opportunities. I also come from a family of small business owners and entrepreneurs, so I did have some general interest in the business world.
Dawn: What advice did you get from mentors along the way?
Jason: Sometimes you have no choice but to focus on the same story as your competitors. But it’s often better to zig when your rivals are zagging. Some of the best stories are those uncovered while all of your competitors are covering the same thing as each other.
Dawn: What advice would you offer to someone starting in the field?
Jason: Finding an opportunity where you can do original reporting — ideally for an editor you respect — can be way more important than landing a gig where you do little to no original reporting at a big-name publication. Also, be bold about cold-emailing/messaging journalists you admire.
Dawn: A lot of people are asking about ChatGPT and writing. What are your thoughts on whether it will put writers out of a job?
Jason: If your job consists mostly of rewriting or summarizing, your job will likely be at risk someday. But I believe there will always be a place for good or great original reporting.
Dawn: Looking back on your career, what would you have done differently?
Jason: I try not to look backward much but, if forced to, I’d say I would have spent another year as a sports reporter before applying to grad school to see if I could have landed a bigger opportunity in that part of the journalism world.
Dawn: What’s next for you?
Jason: I’m doing some writing on my own Substack, called “Already Shipped.” But I’m also talking to a variety of media companies about roles where I can do what I love the most: enterprise or investigative reporting, whether in text, audio or on TV.
If you’re reading this and have an opportunity that sounds like that, I’d love to hear from you.
Dawn Wotapka is a former Wall Street Journal reporter who loves to read and write. She lives in Atlanta with her husband and two children. She is a slow runner and an avid Peloton user. Be sure to connect with Dawn on LinkedIn.
