Jason Feifer '02, editor-in-chief at Entrepreneur Magazine (Photo by Rachel Pradhan)

Jason Feifer ’02 on Clark, writing, and the next Big Idea

Entrepreneur Magazine editor to speak March 31
March 27, 2017

The most valuable lesson Jason Feifer ’02, editor-in-chief at Entrepreneur Magazine, learned while a Clark University student? Question everything.

The advice has served him well as he’s navigated a writing and editing career through media outlets like the Worcester Telegram & Gazette, Boston Magazine, Men’s Health, Fast Company and MAXIM. He’s also freelanced for publications like New York magazine, The New York Times, The Washington Post, GQ, ESPN the Magazine and Salon, and hosts a podcast called Pessimists Archive.

On March 31, Feifer will return to Clark as the keynote speaker for the Innovation and Entrepreneurship Program’s 10th anniversary celebration. The event kicks off with an evening reception March 30 and continues the next day with Feifer’s presentation, alumni workshops, mentoring, and a networking lunch.

We caught up with Feifer and asked him about how his Clark experience helped prepare him for his work, the changing definition of entrepreneurship and from where he thinks the next big idea will come.

How did your time at Clark help prepare you for your current position as editor-in-chief at Entrepreneur Magazine?

At Clark, I came to understand what I like to do best — and where I can best do it. The most significant experience I had at Clark was with WheatBread Magazine, a student-run magazine that doesn’t exist anymore. It was a small, scrappy, occasionally obnoxious operation, run by a small group of students with no formal training and an enthusiasm for experimentation. I took it over in my senior year, and loved the awesome responsibility of shaping its voice and mission. From then on, I always preferred work environments that weren’t fully hardened, and that were still flexible enough for me to help shape. I don’t ever want to just carry the ball. I want to create.

Was there a particular experience at Clark that helped you grow?

Besides WheatBread, I also interned at the Worcester Telegram & Gazette during my senior year, and that experience helped shape the early part of my career. It was the first time I worked with professional editors; it was the first time I saw professional reporters on the job. They made me go live on cable news, and I was so scared that I vowed to get comfortable in front of a camera (which I now have). I never loved sitting in a classroom, to be honest. I hated it in grade school, and wasn’t fond of it at Clark either. But Clark provided many opportunities for me to actually do the things I wanted to do, and not just sit there hearing about them. That’s what mattered.

Do you consider yourself an entrepreneur? If so, do you think more writers and bloggers should see themselves as entrepreneurs?

For decades, the word “entrepreneur” just meant small-business person. Under that definition, no, I wasn’t one. But the definition has changed. Today, an entrepreneur is an identity and a badge of honor; it’s adopted by anyone who hustles and takes risks and makes things happen for themselves. By that definition, yes, I certainly am. I wouldn’t be where I am without having taken big chances, and I’m constantly hustling. I run the magazine, but also created and host a podcast called Pessimists Archive, am writing a novel with my wife, am co-developing a new website, and more. Writers should absolutely see themselves this way — because you can’t just do one thing. You have to be constantly exploring, trying, building, and growing.

Can you cite a single quality that sets the truly successful entrepreneur apart from the pack?

Adaptability. I always think it’s fascinating to hear from successful serial entrepreneurs, because their businesses often seem to have nothing to do with each other. But in fact, there is a common thread: They were the right businesses for the time they were created in. Today’s entrepreneurs must deal with constant change — in technology, the economy, the marketplace, and consumer tastes. The ones that succeed are the ones willing to constantly evolve with the world.

In your New York Times wedding announcement, you’re quoted as saying, “Being a writer is both your job and your passion.” How early did it become your passion and what advice can you give to others about making it your job?

Writing is hard, and making a living at it is harder. You have to really love it; that’s what I meant in that quote. I don’t think of it as a passion, to be honest. It’s just what I do. It’s what’s always felt natural—from drawing comic books in elementary school to printing music zines in high school. And I always had goals. When I got my first reporter job, I decided I wanted to work at The New York Times. At my second reporter job, I decided I wanted to be a columnist. Neither came true, but after a few rounds of this, I developed a way of thinking that helped me succeed, and perhaps it can help others as well. Here it goes: Don’t think about your destination; think about your skillset.

I took a job at Boston magazine. I didn’t care about Boston, but I knew I’d learn to be a magazine writer. I took a job at Men’s Health. I didn’t care about health, but I knew I’d learn a kind of magazine editing called “packaging.” Then I went to Fast Company. I’d never read the magazine, to be honest, but I knew I could learn to be a long-form editor there. And so on. At every job, I focus on what skills I’m deficient in and what I can learn—because that, more than anything else, will enable me to keep succeeding in a fast-changing media world, where you need to be multi-skilled to survive.

You’ve written articles about topics as varied as sex, selfies, germs on flip flops, ham radio and Hanson. Which one did you enjoy researching and writing the most?

When I started in journalism, I thought I’d enjoy having a beat. But I discovered that I get bored covering the same subject too long. However, I never get bored of writing a certain style of story, which is this: I love stories about things that at first seem weird or funny or un-serious, but that, if you’re willing to spend the time taking them seriously, turn out to be revelatory in some way. I always look for those stories, no matter the subject.

Do you think entrepreneurship will still look the same in 20 years as it does now, or will a shifting economic landscape in the U.S. and abroad change its nature?

There’s an explosion of entrepreneurship today — both in terms of the numbers of businesses that people start, and the number of people who identify as entrepreneurs. That, I think, is the result of our economy. Large companies are shedding employees, and we’re moving away from a world of predictable careers. People want to control their own futures. In a generation from now, of course, our economy could look very different once again, and people will react accordingly. Tools and technology will certainly change. Government policy will change. But some things don’t change: Entrepreneurs are daring visionaries that alter our world — they were before, and they will continue to be. The only question is, what will they be responding to next?

If you had to make an educated guess, from where do you think the next Big Idea is coming?

In the 1800s, New York City was in a full-blown horse manure crisis. Horses were the main mode of transportation, and were producing hundreds of tons of poop every day. It stunk. It caused health problems. It was awful. The greatest innovators of the day couldn’t solve the problem, though. Know what did? Cars — a technology that wasn’t designed to eliminate horse manure, but did exactly that. We can never know where the next great innovation will come from, or, for that matter, how it will ultimately improve our world. I’d be foolish to guess. But that’s what makes covering business so exciting. Every day, I hear from people with big, ambitious ideas, and I think: That’ll either fail, or change everything. The best I can do is encourage everyone to keep trying.

Photo at top: Jason Feifer '02, editor-in-chief at Entrepreneur Magazine (Photo by Rachel Pradhan)