Jason Feifer, EIC of Entrepreneur Magazine: There’s such a thing as “right idea, wrong time.”

Just because you can’t execute an idea at one moment doesn’t mean it’s a bad idea, or that you’re a failure

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I first had the idea for this novel when I was in my 20s, more than a decade ago. I tried and failed to write it many times. It wasn’t until much later, when I was married to a novelist, that I finally had a partner who could help make this book a reality. Here’s the takeaway for people: There’s such a thing as “right idea, wrong time.” Just because you can’t execute an idea at one moment doesn’t mean it’s a bad idea, or that you’re a failure. Sometimes it’s just not the right time.

I had the distinct pleasure to interview Jason Feifer. Jason is the editor-in-chief of Entrepreneur magazine, and host of two podcasts: Pessimists Archive (iTunes, site), about the history of unfounded fears of innovation, and Problem Solvers (iTunes, site), 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 cowrote with his wife, Mr. Nice Guy, came out on October 16, 2018, from St. Martin’s Press. Jason lives in Brooklyn. Jason is available to speak at events about how to get press for your business, conduct fireside chats, and moderate panels about subjects of interest to entrepreneurs. 

Thank you so much for joining us! Can you share a story about what brought you to this particular career path as the Editor-In-Chief of Entrepreneur?

Honestly, it began by a desire to get free CDs and entry into concerts. My first “professional” writing, so to speak, was for a local music magazine in Florida when I was in high school. It gained me access to lots of my favorite musicians at the time, which felt amazing, and I realized: Wow, being a journalist is like having an all-access pass to the world. People just let you in and talk to you. Of course, as my career developed, my sensibility and sense of mission matured. Now I feel fortunate to speak to the smartest entrepreneurs and business leaders every day. I learn a lot from them personally, and pass as much of it along to my audience as I can.

Can you share the most interesting story that occurred to you in the course of your career at Entrepreneur?

Oh boy. There are too many. But when I look back upon this part of my career, I’m sure that the most interesting thing will be how I learned to go from being a magazine editor to a public “thought leader” — someone that people interview (like right now!) and ask to speak on stage and so on. That took a real adjustment; I wasn’t comfortable with the role at first. But I’ve since come to love it, and am excited to inspire entrepreneurs every day.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

This probably isn’t a funny mistake, per se, but I remember something very embarrassing from my first job as a reporter at a community newspaper. I was interviewing some local high school student who won a poetry contest, and she’d told me that most of her poems end up the trash — she just keeps writing and throwing them out until she hits something she likes. So I opened the story with something like this: “[The girl’s name] writes poetry for the trash.” Then I went on to explain the whole thing about her throwing poems out. It all seemed fine to me, but a few months later, I ran into the girl’s mom and she yelled at me because her entire family had read that “writes poetry for the trash” line as an insult, and it really upset them. It made me realize the power that writing can have, and how you cannot be casual or dashed-off about it. You have to be careful and intentional.

What are some of the most interesting or exciting projects you are working on now?

The most recent project is a novel called Mr. Nice Guy that I wrote with my wife. It’s a romantic comedy set in the world of New York City media, and is about two people who each week sleep together and then critically review each other’s performance in a magazine. It’s lots of fun. Kevin Kwan, the author of Crazy Rich Asians, even wrote us to say, “I COULD NOT PUT THIS BOOK DOWN!!!” Literally just like that. All caps and three exclamation marks. We were thrilled.

Can you share the most interesting story that you shared in your book?

We share a lot about what it’s like to work in the media world, and the crazy egos and excess you encounter along the way. A few reviewers have said it’s the most accurate portrayal of the industry they’ve ever read. So if you’re curious at all about that, definitely check it out.

What is the main empowering lesson you want your readers to take away after finishing your book?

I first had the idea for this novel when I was in my 20s, more than a decade ago. I tried and failed to write it many times. It wasn’t until much later, when I was married to a novelist, that I finally had a partner who could help make this book a reality. Here’s the takeaway for people: There’s a such thing as “right idea, wrong time.” Just because you can’t execute an idea at one moment doesn’t mean it’s a bad idea, or that you’re a failure. Sometimes it’s just not the right time.

Which people in history inspire you the most? Why?

I have a history podcast called Pessimists Archive, which investigates why people oppose new innovations. Past episodes have included the bicycle, recorded music, chess, and the novel. The people in history who inspire me are always the ones that are aware of their place in history — that can see beyond the momentary panics or short-sightedness, who appreciate that the people of their day can’t possibly know everything, and who are clear-eyed about the wide possibilities of the future. I love running into records of people like that. I hope one day in the future, someone thinks the same about me.

Which literature do you draw inspiration from? Why?

I’m always inspired by excellent storytelling, and writers who are able to capture a time and place and characters. One of my favorite novels is The Thousand Autumns of Jacob de Zoet, by David Mitchell. It’s just beautiful from start to finish.

How do you think your writing makes an impact in the world?

It’s not really my place to say; it’s for my readers to say. But I am constantly thrilled and heartened by the emails I regularly get from people who say that my work lifted them up, gave them comfort in difficult times, and inspired them to keep going. That’s amazing.

What advice would you give to someone considering becoming an author or journalist like you?

Constantly develop new skillsets. Learn to write in your own voice, but also to adjust it for new mediums: Be a newspaper writer, a magazine writer, a podcast writer, a speech writer, a short-form social media writer, and so on. The world of media is ever-changing, and you want to become as versatile as possible.

You are a person of enormous influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

That’s so hard to say. But for what it’s worth, here’s an idea I’ve been kicking around: We could solve a lot of our country’s political problems if no elected official was ever allowed to run for re-election. Every elected position would be a one-term position, by law. Constant new ideas, no entrenched interests, no playing to a base, no re-election campaigns. I would love to see that movement begin.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

If I answered that in full, it would take me a week. So here’s just one quickie: 

I wish someone told me to start collecting all information. I’ve met so many amazing people during my career, but I didn’t systematically keep their names and email addresses. So many of them are just lost to time. I started making a more concerted effort to collect everything about a year ago, but I still have a lot of catching up to do.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this, especially if we tag them 🙂

I honestly don’t have an answer to this! 

I’m fortunate to meet a lot of amazing people.

How can our readers follow you on social media?

I’m @heyfeifer on Instagram and Twitter. And people should definitely sign up for my monthly newsletter, The Feifer Five, which is five inspirational insights about entrepreneurship. They can find it at my website,

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