Q&A: Jason Feifer is the entrepreneur journalist behind Entrepreneur

Jason Feifer is editor in chief of Entrepreneur magazine,  and host of two podcasts: “Pessimists Archive” about the history of unfounded fears of innovation, and “Problem Solvers” about how entrepreneurs solve unexpected problems in their business.

He was previously an editor at Fast Company, Men’s Health, Maxim, and Boston, and has written for New York, ESPN, Slate, GQ, New York Times, Washington Post, The Guardian and others.

A novel he co-wrote with his wife, Mr. Nice Guy, came out in the fall of 2018 from St. Martin’s Press.

Feifer spoke by email with Talking Biz News about his job running the magazine and how it caters to its readers. What follows is an edited transcript.

You joined Entrepreneur slightly more than three years ago. What attracted you to the magazine?

My first two national magazine jobs were at Men’s Health and Fast Company, and both were what I call “carrying the ball” jobs. My role was to essentially do what my predecessor in the same position did: to edit this section, or execute this concept, or assign these kinds of stories, and to maintain a consistency within the organization. I quickly lost interest in jobs like that.

I became more interested in molten environments—places that were in flux or hadn’t hardened yet, and which I could take an active role in shaping. Entrepreneur was exactly that: The brand in 2016 was looking for a major refresh, and its company leadership was very open to change and fresh ideas. That was the opportunity I jumped at, and I’ve found it to still be true today: Entrepreneur lives by its name and embraces change.

What have been some of the changes you’ve instituted since becoming editor in 2016?

The biggest change was the way we thought about ourselves. Entrepreneur had traditionally been a small-business magazine. The word “entrepreneur” had, for the past few decades, had a very small-business association, so that was our audience and that’s who we served. But the word has evolved in the past decade. An entrepreneur is now not just a traditional small-business owner, but really anybody who hustles and creates and makes things happen for themselves. The word “entrepreneur” isn’t a career designation; it’s now a mindset and identity.

So we moved the brand to where the culture was—talking to a far broader set of people about a far broader set of issues. Are many of them small-business owners? Yes, of course. We’ll always serve them. But now when we also talk about, say, motivational and inspiration and the emotional challenges of pursuing your own path, we’re also resonant in many other ways.

Who do you see as the magazine’s key readers?

Like any special-interest magazine, it’s a mix: Some of our readers are people dreaming of pursuing their own path, some are just beginning, some are many steps along their journey, and some are experienced entrepreneurs who read to stay current on what others are doing. I tend to focus on the thing all these people have in common, which, like I said before, is the emotional experience of entrepreneurship. You can get all these people in a room and they’ll all tell similar stories of feeling lonely and crazy.

When we live inside that space—getting super real about what entrepreneurship is, and giving people that sense of understanding and belonging—we serve them in a unique and valuable way.

What do you want to give to them in terms of content, either online or in the print magazine?

Usefulness. I know that nobody reads Entrepreneur—the magazine or the dot-com—just because they’re eager for some leisure reading. They’re looking to learn. They’re looking to build. They want stories and information that helps them. So my goal is to constantly be on the lookout for what people need.

How does Entrepreneur distinguish itself from its key competitors?

I think of us as the brand that reaches people on a human level. It’s right there in the name: Entrepreneur. People can say “I’m an entrepreneur”—which is not a sentence you can complete with any other business magazine title. We’re there to understand, to relate and to help. I see our competitive set looking at business from a higher level, focusing on specific industries or trends, covering business as if it’s a subject. I don’t think of it as a subject. I think of it as a life.

The magazine updated its cover design last year. What was behind that?

I wrote a column about it at the time, which has a lot more detail. But in short: Like any good entrepreneur, I want to always be asking myself why I’m doing the things I’m doing. Is it because that’s the way it’s always been done? If so, then surely there’s a better way. So one day I stepped back and started asking big questions about the cover—from how we were creating it to what its role was—and that led me to have a conversation with the marketing agency Huge, who proposed a big redesign.

The process was amazing, and the most startling part of it was when Huge told me this in a presentation: “You’re a magazine for and about entrepreneurs — the very people who seek out something new, different. They don’t want a regular business magazine because they don’t want to be regular business people. You have permission to be unlike any other magazine on the rack. Be an entrepreneur.” And I thought: Holy crap, they’re right.

What are the key issues in writing about entrepreneurs and start-up companies?

To me, the key issue is identifying the relatable moments. I don’t write about a company because it does something interesting. I write about a company because its founder made an interesting and perhaps counterintuitive decision that I think other entrepreneurs could learn from. Finding that is hard. Communicating it to the bazillion entrepreneurs and publicists I hear from is even harder.

How do your podcasts fit into Entrepreneur’s overall strategy?

We produce two in-house: “Problem Solvers,” which I host, and “How Success Happens,” which is a team effort. The strategy is simple. We want to be wherever our audience is, and serve them in whatever way is most valuable to them. And also, frankly, I just love podcasting and audio storytelling, and I get a lot of joy out of creating the show. Problem Solvers is weekly, and each episode is about how an entrepreneur solved an unexpected problem in their business.

We really zero in on it—this isn’t a sprawling interview show. Producing it has also been useful for me in other ways: I regularly take stories I hear on the podcast and put them in the magazine, or cite them when I speak at conferences.

How did you get the idea for The Feifer Five email newsletter?

From the many entrepreneurs I speak with! So many of them have personal newsletters, and told me I need to start one too. It’s basic audience-building: Although I speak with Entrepreneur’s audience all the time, many people want to connect with me directly, and there’s no better way to do that than through a newsletter, where you can reach people without an intermediary.

So I began about a year ago. It’s been a blast. I think of myself as an experiment in entrepreneurship: Just like Entrepreneur’s audience, I’m always building and experimenting and side-hustling—I have a personal podcast as well, I give keynotes, I’ve developed websites, and more—and when I share the ups and downs of that journey with people, everyone wins (including Entrepreneur).

You have a great reputation of responding to people who email you asking for advice, even if they’re not involved with the magazine. Why do you do that?

Why wouldn’t I? I hear this quite a lot—people are surprised that I’m so responsive—but I honestly don’t understand why other people in roles like mine don’t respond to everyone too, or why they make themselves so difficult to reach. Why would you do that? Because you think you’re so important? Come on. You’re not. Here’s how I see it: I’m incredibly fortunate to be in a position where people turn to me for advice or insight, and that I have the ability to brighten someone’s day just by communicating. I mean, it’s crazy—I reply to an email and then someone tells me it made their day to hear from me. Who am I? Just a guy who learned some stuff and got a cool job! The whole situation is silly and awesome. I always want to keep that perspective.

But I can also make the self-serving case. Responding to people is literally the easiest and fastest way to help yourself. First of all, it creates fans: When I reply to someone—and I do it by email, LinkedIn, Twitter, Instagram, Facebook Messenger, and I even have a chat function on my website where people can reach me—they are infinitely more likely to read the magazine, listen to my podcasts, and generally follow my work and support me.

It also helps with learning: I want to be constantly in touch with and aware of my audience’s needs, and there’s no better way to do that than to be always engaging with them. All it takes is a few minutes. I do it on the subway or before bed or whenever I have a spare minute. It’s literally the most value per minute of anything I do.