Interview with Jason Feifer

Today, we are interviewing Jason Feifer. Jason is the editor in chief of Entrepreneur magazine, and host of three podcasts: Pessimists Archive, a show about why the pessimists of the past were wrong and how to be optimistic about the future; Hush Money, about the way money makes life awkward; and Problem Solvers, about entrepreneurs solving unexpected problems in their business. He has been an editor at Men’s HealthFast CompanyMaxim, and Boston magazine, and has written about business and technology for the Washington PostSlateNew York, and others. His novel Mr. Nice Guy, which he wrote with his wife, is currently being developed for television. Jason lives in Brooklyn, New York.

Question:  What important truth do very few people agree with you on?

Jason: Change can be good, and new is not inherently bad. That may not sound controversial, but now apply it to technology and people’s fears about social media—and you see how many people naturally equate new with bad. I spent a lot of time studying innovation and change in my podcast Pessimists Archive. I also see the patterns in the most successful entrepreneurs I meet through Entrepreneur magazine. The result is clear: When you embrace change, you win. When you don’t, you let everyone else pass you by.

 Question: How were you as a student?

Jason: Disinterested. The classroom was never for me.

Question: What is the one thing you would like to change about yourself or improve on? 

Jason: I should learn to stop and appreciate the moment more. I’m often too focused on building for tomorrow.

Question: What habit do you have now that you wish you started much earlier?

Jason: Building upon work. I used to do something, put it out into the world, and then move on to something completely new. Now I look back on that and think about all the wasted contacts, ideas, and opportunities. If you’re not building upwards, you’re letting things fall into nothingness! I now think of everything that I do as part of one continuous build.

Question: Who would you most like to sit next to on a 10 hour flight and why? 

Jason: Nobody! I do some of my greatest work while I’m flying—free of distractions, free of incoming emails, free of people popping into my office (during normal times) or my kids interrupting me (during Covid times). I never get wifi on the plane. I just pick a big project, and I spend hours getting through it.

 Question: For you, what’s the best and worst thing about getting older?

Jason: Best thing: I know more, and I’m more confident. Worst thing: I get tired so early!

Question: What one question can you ask someone to find out the most about them?

Jason: In college, a friend of mine would sit down with people and say, “Tell me a story.” I always liked that. I never do it now, but I suppose I never have to. When you run a magazine, everyone immediately wants to tell you their story.

Question: What is your motto for life?

Jason: When I was in my 20s and focused on building my career, I kept telling myself this: “I’m not fucking around.” I don’t say it to myself much anymore, but I still feel it every day.


Twitter: @heyfeifer

Instagram: @heyfeifer

LinkedIn: linkedin.com/in/jasonfeifer/

I’m not fucking around.