Making The Most Of Change With Jason Feifer

They say that the only constant thing is change. If it happens all around us all the time, then why do people fear change? On today’s podcast, Dr. Diane Hamilton sits down with the Champion of Change, Jason Feifer. Jason is the Editor-in-Chief of the Entrepreneur magazine and the host of three podcasts – Pessimists Archive, Problem Solvers, and Hush Money. Tune in to this episode to discover why Jason considers change as an opportunity to be embraced and learn how you can make the most of it.

TTL 757 | Change


I’m glad you joined us because we have Jason Feifer. He is the Editor in Chief of Entrepreneur Magazine. He hosts three podcasts. He’s a former editor at Men’s Health, Fast Company, Maxim, you name it, he’s worked there. He’s got such an interesting background and we’re going to have a fun show.

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Making The Most Of Change With Jason Feifer

I am here with Jason Feifer, who is the Editor in Chief of Entrepreneur Magazine and host of three podcasts. Pessimists Archive, a history show about why people resist new things. Hush Money, about the way money makes life awkward, and Problem Solvers, about entrepreneurs solving unexpected problems in their business. He has written several books. He has an interesting background. I’m excited to have you here. Welcome, Jason.

Thanks for having me. I appreciate it.

I am looking forward to this because I get many entrepreneurs on the show. I have many people interested in entrepreneurship. Entrepreneur Magazine is definitely one of the top magazines but you’ve also been the editor at Men’s Health, Fast Company, Maxim, and Boston Magazine. I was looking at your background. How do you get into that level of success? I want a little backstory on you.

First of all, it’s a funny thing about words in bios. You did something that I’ve noticed almost everybody does when they’re working off of my bio, which is that they drop the word and in “and editor at Men’s Health, Maxim, Fast Company, etc.”

It says “the” in the bio in front of me.

I don’t know, that keeps happening. It’s a funny quirk of how a single little word makes a difference. I didn’t run those magazines but I was a senior editor at those magazines. The answer to my bio is that I’ve always focused on everything that I’ve done, thinking about what I’m learning and how it can develop into something else. I have this philosophy about work called, work your next job. The idea is that, in front of you, me, and everybody who’s reading at any time right now, we have two sets of opportunities in front of us. Opportunity set A and opportunity set B.

Opportunity set A is everything that’s being asked of you at your job, everything that you’re being evaluated by. Opportunity set B is everything that’s available to you that nobody’s asking you to do. That could be something that’s at your job, getting involved in something that’s not a core part of your job but is there and it could be a great thing. It could be learning how to podcast at home in your spare time, whatever the case is. I have always found that opportunity set B is more important. It sets you up for a future. You may not exactly know what it’s going to look like but you know that it can be bigger and different from the thing you’re working on. Whereas I’ve always felt like opportunity set A only sets you up to do the thing that you’re already doing and I’m always looking to do more.

I’ve watched one of your interviews. It was the GoDaddy interview where they gave you the three choices of what you agreed with most on cards. You picked a comfort zone is a beautiful place but nothing ever grows there. You said you pick that one because you see successful entrepreneurs are able to push themselves into this uncomfortable place. That’s important because with my work with curiosity, I’m trying to get people to go to that uncomfortable place. As you said, it no longer becomes uncomfortable.

That’s a scary place to be. A place where you’re so comfortable that it’s too comfortable to leave. I’ve always pushed myself to not stick around too long once I feel like I know what I’m doing. At that point, I feel like I would stagnate and I’d become unhappy. There’s just something in me, I don’t know what it is but at about the 2.5-year mark in every job I’ve ever been, I get itchy and dissatisfied. I start looking around for other things to do.

I’ve been at Entrepreneur for longer than 2.5 years but the reason that I’m able to manage that constant sense of what’s more to the discomfort is because this role enables me to learn and challenge myself in many other ways. Podcasting, public speaking, book writing, these are all things that have become available to me because of my role. While I’m excited to continue to make the magazine and to be a great steward of Entrepreneur, the brand, I’m also always pushing myself for what else is out there.

I’m like that too. I was Editor in Chief for a website a long time ago. I’m curious how you got into that. What was your background in education? Were you an English major? Was there something that made you better at writing or editing? What was the foundation for that?

[bctt tweet=”Work your next job. ” username=””]

I was an English major. I don’t think that it did anything for me, to be honest with you. Being an English major like many academic subjects is largely about approaching the subject in an academic way instead of in a practical way. I was never into that. Why am I reading all these books? What am I supposed to be getting from this? I couldn’t figure it out, but there was no other subject that interested me. I knew that my raw material, I thought of it as writing at the time, now I think of it as storytelling.

I was interested in figuring out where to put this thing. I felt like I was walking around with something that was raw but good. I had started in high school. I started a blog before the word blog existed. I was writing for local music magazines. I had a sense that I knew how to communicate in a way that felt intuitive and that people responded to. I didn’t know what to do with that. I was an English major. I was also a philosophy minor, which I had a lot more fun with.

The great thing about philosophy is that it challenges you to think extremely logically about something and also to appreciate language. A lot of philosophy is oriented around what exactly this or that means, because if we can establish that, then we can extend the thought. I found that to be a useful way of thinking about the world. I then became a newspaper writer out of college. I kept trying to figure out how big I could build my skillset. That is essentially how I came to stop thinking of myself as a reporter, and then stop thinking of myself as an editor. I start to think of myself as someone who tells stories in their own voice. To establish my own voice and understand that the thing that I’m good at is taking in information, and then translating it into something that’s useful for other people.

A lot of people can do that either in the spoken word or the written word, but you’re great at both. I was watching you as a speaker. You’re so enthusiastic. It’s such an entertainment to watch you. You don’t think of an editor or and editor.

In this case, I can be just the editor.

In the past ones, you were an editor. I got it.

This is what we’re talking about with philosophy. It comes down to the individual words.

My dad was an English teacher. My sister is an English grammar teacher. One of the weirdest things about listening to myself when I play these back is, I would write something correctly but I would say it incorrectly. I’m like, “I never knew I said that.” I would say that instead of who and different things. It drives me crazy. I can’t listen to myself because I’ll go through the grammar check of everything I do. You do a good job though of speaking. I see different styles. I’ve had so many Hall of Fame speakers on the show that it’s so fun to watch different people do their thing, but everybody’s got their style. How did you learn to be such an animated speaker?

It’s funny, it all comes back to the first observations I made with myself on camera. Speaking of that opportunity set B, when I was at Fast Company, I was there as a print magazine writer and editor. I then started the video department when I was there. I volunteered to be in the video department even though I had little on-camera experience, but I had this willingness to learn. I watched myself on the camera and I came to this realization.

They always say that the camera adds 10 pounds. The camera subtracts ten energy points. It’s so weird. If you talk normally like you would at a dinner table, you sound like you’re asleep. I kept amping myself up trying to compensate for that. Eventually, I discovered this thing that’s so valuable if you ever want to do something in public. The way that you conduct yourself in front of other people in a performative way, being on stage or something like that, is not natural. You have to get comfortable speaking and acting in a way that is not natural because you’re playing to an audience.

Once I realized that, I felt like I have to figure out who I am. What’s my character? What’s my voice? How do I present? The thing that comes most naturally to me is to be energetic and enthusiastic. I’m a high energy person, to begin with. I don’t talk like I’m talking to you now if I’m at the dinner table. That would be annoying, but it’s how I found what works for me. On mic, I slip into this character where I have a sense of what people want from me and what my role is in front of them.

TTL 757 | Change
Change: A lot of philosophy is oriented around what exactly this or that means, because if we can establish that, then we can extend the thought.


I started doing it and then I would watch people who are high-energy performers. The two that came to mind the most in the beginning for me were Mike Pesca, he’s an NPR guy. He hosts a couple of podcasts on Slate. Also, Jon Taffer, the host of Bar Rescue. Both of which are guys who I’ve been fortunate to get to know but at the time, I knew them from their personas. I was aware that they were doing high energy all the time, and it didn’t come off as insane. It came off as engaging.

I thought, “That gives me permission to turn it up way past what is a natural and normal way of speaking,” then I’ll watch myself. I’ll find that it feels engaging. Once you trust that, it feels like that scene in Indiana Jones and the Temple of Doom where Harrison Ford is walking across the invisible walkway. You put your foot out and you know that it’s going to feel crazy but you know that you’re going to land on solid ground. That’s what speaking in an unnatural but performative way feels like.

I did something similar to that when I was creating one of my speaker reels. I said, “I’m just going to do this.” I was watching some beforehand, I go, “I’m going to just be ridiculous.” It wasn’t even over the top coming across at all when I watched it later. It’s weird. Your voice though is different for men versus women. When women get to that louder voice, sometimes it gets shrill. It’s harder for women to do that than for men. You guys get deeper and more interesting as you get louder, where we start going like scratching a tap board. That’s the one thing I noticed with my voice, if I get louder and too excited, I start irritating myself listening to it.

I have so much to say about what you said. I did a segment on PIX11, which is a television station in New York. It was a five-minute TV segment. Afterward, even though I am talking like this and I’m already animated, I watched it and it was like, “I could have been more animated. I missed opportunities to emphasize things.” Whatever is holding you back, get rid of that. You’re totally right. This is an unfortunate fact of the world. Unfortunate doesn’t even do justice to the deep unfairness of it. Men have a lot more leeway in this kind of stuff. I would not say that my performative voice is deep but I do know that although I’ve gotten some insults about it in my podcast reviews, people largely leave me alone about it.

In the podcasting world, men keep accusing female podcasters of having vocal fry. They say, “I could have listened to this except for your vocal fry.” Scrap that out, except that you are sexist. That’s what we’re talking about. We’re not talking about vocal fry. We’re talking about your sexism. It’s an absolute problem but the important takeaway for anybody is that you don’t have to turn it up to eleven in order to be an engaging speaker. What you need to do and this is something you’re doing as well, is you have to be mindful about the way that you talk. You have to talk in an intentional way because what people respond to is control. Are they seeing someone who is in control? Are they seeing someone who is presenting something that they feel like they can devote their time to? The problem is if you just go up and speak in an uneasy or dull way, you don’t sound like you got two hands on the steering wheel. That’s what’s most important.

As you’re saying the difference of how it goes higher and lower, or the difference in the women’s voices and men’s, it made me think of The Practice. That show on television. Lara Flynn Boyle plays an attorney. The whole time she’s got this low, sexy thing, but when she gets pissed off in the trial, all of a sudden, it goes way off the top. You have to pay attention to that. I worked with Dr. Gilda Carle, I don’t know if you remember her work because she does so much stuff. She was on Sally Jessy Raphael, Howard Stern, and everybody else’s shows. She and I worked together. We do a company, podcasting on different things where we talk about how to be in the media and in certain things. It’s interesting to look at what people need to do to speak better to get their brand out there. You have a brand. You’re all about change. You inspire change. Is that what you consider your main focus? You do so many things.

Identifying what that core focus is a project that I spent years on. Yes, it came down to change. I can tell you how I got to it because it’s an important lesson for anybody who’s trying to figure out what it is that they stand for. When we think about personal brand, people often get hung up on the word personal. They think, “I have to put myself out there. That can be uncomfortable or embarrassing. I don’t know how much I want to be in public.” The thing is that that’s the wrong word to focus on. The word is brand because a brand is a simple, repeatable thing that has an identifiable way of fitting into somebody’s life. That’s what people want.

When people tune in to you and they tune into me, they don’t care about us and they shouldn’t. They don’t care about me. Who cares about me? Nobody outside of my family and there’s no reason for them to. Instead, what they care about is what am I delivering to them? What value do I have for them? To do a personal brand well is to identify what that is, what people see in you that is valuable to them, and then narrow yourself down so that you’re constantly delivering on that. I found that there was a confluence of things going on. One, the message that I was most interested in at Entrepreneur was about how entrepreneurs are utilizing change.

People kept asking me, “What are the qualities of a successful entrepreneur?” I found that the answer was that the entrepreneurs that I meet who are most successful are the ones who are good at changing. I started steering our coverage towards that. At the same time, Pessimists Archive, my podcast about change started to become a real thing. It developed a substantial audience. The story there is about understanding change throughout history. Why are people afraid of change? Why are they afraid of innovation? What does it take for them to overcome it? I realized that I could combine those insights and stand at the intersection of it and be the guy who talks about change. It felt exciting for me because it was something that I struggled with as a kid, which was feeling like I wanted everything to stay the same but it can’t. Realizing that this is like a perennial subject, everybody struggles with it. People are always looking for insights into it. I then started heavily going into it.

As I was watching some of your talks and what you deliver in your speaker reels and different things, it tied into what I do with curiosity. I created an assessment that determines the things that keep people from being curious. I was thinking, “I wonder what he does to assess what keeps people resisting change?” Do you quantify that? What do you do when you deal with groups when helping them with change?

It’s a matter of first shifting perspective and understanding what change is. I have this sense and this comes a lot out of studying history and why people have feared and resisted the things that we think of as commonplace. It includes multiple things that we’re using now like radio, telephone, recording audio, these are all things that people hated. In understanding what people were freaked out about, we can get a good understanding of how to think about change and our own reactions.

[bctt tweet=”A scary place to be is somewhere where you’re so comfortable that it’s too comfortable to leave.” username=””]

The first thing that I tell people is, “You come from the future.” What I mean is that everything that you are, the music that you listen to, the lifestyle that you lead, the ideas that you have, the way that you dress, the technology that you use, the jobs that you have. Everything about you was once new and therefore terrifying to the previous generation. People before you saw the things that made you up and they said, “These are bad. They’re taking us down a dark place. This is the end of our country. This is the end of our people.”

Everything that you hear people say now about things, they said them back then about the stuff that they’re not familiar with. If you look at yourself, you don’t think you’re bad. You don’t think that you’re made up of terrible things. You think you’re fine. In fact, you think that you’re so fine, that now that you see change coming along, you’re saying, “No, I can’t lose the things that I am. These are the good things.” If you can appreciate that you are the evidence that change is okay, that changed by itself, that new things are inherently not bad, then you can be open to understanding how there are opportunities going forward.

A lot of this is about mindset. It’s about being able to understand that there are opportunities coming. A big part of fearing change is it’s so much easier to see loss than gain. Loss happens first, gain comes second. You obsess over the loss, and you don’t anticipate what the gain is. I spend a lot of time trying to get people to fill those gaps in and see how it happened in the past. How they themselves have been participants in that change. That’s a great way to start getting over it.

You brought up so many great things. I studied Carol Dweck’s work with mindset for curiosity. What curiosity was about was getting out of status quo behaviors. That’s what you’re talking about as well. What we found in a lot of the research is that social learning is comfortable. You’ve seen the thought experiments where they ring a bell, and people stand up and sit down for no reason just to see if they’ll follow the other guy who’s doing it, and then they do. You go, “Why are we doing this? Everybody’s standing up and sitting down for no reason because everybody else did it.” That’s what’s killing companies.

You said, “Resistance is for losers.” I love that because if you want to win, you have to change. I agree. If you keep doing things the status quo way, you’re going to end up like the Blockbuster and the Kodak, and we know all the examples. You must read some great ideas and different things when you’re dealing with Entrepreneur Magazine and any other magazines with which you’ve been part of in the past. What inspires you the most about an article? I’ve had Marty Zwilling on the show. He’s written a million articles for Forbes about entrepreneurship. I’ve had many people on the show who are great writers. I’ve written for different areas in the past. I’m curious, if somebody wants to write for Entrepreneur, what do you look for? What makes it a good article?

If we’re talking specifically about Entrepreneur, we first have to divide up into Entrepreneur Print Magazine and They’re separate things and they’re looking for separate things. We should spend most of our time talking about because that’s where most of your audience would have access to. Entrepreneur Print Magazine is largely written by professional writers, journalists, and we’re doing a lot more narrative storytelling, a lot of reporting, and so on., we have a robust contributor network. It was rebranded as the Entrepreneur Leadership Network. It has a formal application process. You just google Entrepreneur Leadership Network and you can find the landing page there and then you can apply. We have editors who are reviewing people’s applications first, and then their individual submissions if they’re accepted.

What we’re looking for is useful advice that is drawn from experience. We want things that feel like they’re directly applicable, that they’re answering people’s existing questions. Think about the way that you get to an article at or anywhere else. You’re largely searching for a question. That is the primary driver of traffic, not just on but pretty much to every website is Google. That’s because it’s intent traffic. It’s people who are looking for a specific thing.

You want to be answering people’s questions. What are their existing questions? You want to go narrow. Some people will pitch us and they’ll be like, “I’d like to write a piece on four ways to market your business.” That is unbelievably broad that it’s going to be useless. You need to get down to the level where you’re answering specific questions for people. You’re able to deliver what are valuable and tangible, “I can read this and put it into my life insights.” That’s what people need. You need to draw from your own experience. We discourage people from writing about other people. We want you to draw from your own experience. You’re the expert. Tell us what you know, and then frame it in a way that other people are searching for.

When I used to write for Investopedia when it was Forbes-based, they always wanted you to have evergreen content. I would want to write about something cool and new, and they’d go, “No, this has to be evergreen.” Do you do that or do you do like what’s hot kind of thing?

We do a mix. Evergreen is the right move for an audience like this because people are going to be searching for this kind of thing for a long time to come. One of our perennial stories, this was produced in-house however many years ago. The headline is something like, “Need a Business Idea? Here are 55.” This is something that people have been reading for years. It’s because it’s simple. It hits a pain point, people want to start their own business but they don’t have an idea. They’re looking around and you can imagine how they found it. They found it by searching for great business ideas or something like that. You want to walk this fine line between being timely and evergreen. You don’t want to write something that could be written in 1980 or read in 2030. You want to be writing something that feels like it’s produced for now, that it’s responding to needs now, that it is written in a way that feels current, that the references are current but that has a long tail.

I remember when Steve Forbes was on the show, we talked about what Forbes went through when they had to switch from print to dot-com or digital. That was almost catastrophic for them if they hadn’t done it right. Were you in the business before or after that whole switch? You look like you’re not super old. I don’t know if you were around when that happened. Was this a time that you experienced when they were facing, “We have to take Entrepreneur digital,” or did you get in later?

TTL 757 | Change
Change: Talk in a really intentional way because what people respond to is control.


I wasn’t there. I feel like for my own journalistic career is that I missed the golden days of money spending. I do not subscribe to the good old day’s mentality about anything, but it is certainly worth saying that there was a time where magazines were spending tons and tons of money. Those were probably nice days to be working in. I missed them. I came in at the tail end. I’ve only been at Entrepreneur for a few years. At that point, the digital build-out had happened, but we’re always evolving it. I’ve certainly been a part of a lot of rethinking.

I was at other brands and newspapers before that as they were grappling with, “What exactly are we supposed to do with our website?” I remember the days where you’d update the website once a week or once a day or whatever, and the dawning realization that you could publish endlessly. In fact, the more you published on the site, the more people would come to the site. They’re thinking about what it is that you’re publishing.

One of the greatest realizations that publishers had was that the audience that’s coming to the legacy products, the print product, and the audience that’s coming to the website are different audiences. They’re looking for different things, they’re spending different times, and their consumption habits are different. You have to be writing in a different way for them. Once you figure that out, it’s transformative. In ways, that have been good, but also in ways, that have been bad. The publishing industry is still figuring it out.

I see many different digital forms from major companies, even Forbes has different sites that use their brand name. Does Entrepreneur branch out into anything other than the main Do they offer anything for consultants and all the things that Forbes does and other magazines do? I’m curious about what you do in that respect.

We’ve done it differently. We don’t quite go into the channel route that Forbes does. We’ve launched a couple of other Entrepreneurs. There was a time where there was a Young Entrepreneur, that doesn’t exist anymore. There was a Women Entrepreneur that we did for a while. It still exists but we’re in the middle of figuring out what to do with it next. There’s Green Entrepreneur, which covers the cannabis space. We’ve explored a couple of others, and then there are also international editions. There’s Entrepreneur Europe and so forth.

There was an interesting experience that I had when I was at Fast Company which was a number of years ago. Fast Company had built out all of these microsites or subsites, whatever they would call them, and maybe they’ll sound familiar to people. They were all Co’s. There was Co.Design, Co.Create, Co.Exist, and there might have been a few others. Co.Design was covering the design world. Co.Exist was social good stuff. Co.Create was creativity. The advertising industry and so on. There was a tech one as well that I can’t remember. Anyway, the reason I’m telling you this is that it ended up creating this existential question for Fast Company, which was, “If we’ve created all of these subsites, what is What belongs on”

They’ve taken everything off the table and put it on another tables.

What is it anymore? Do readers know what it is? This was a real challenge. By the time I left Fast Company, they hadn’t resolved it. From the outside looking in now, I can see what the resolution was, which is that they got rid of them all. They closed them all and they folded them all back into because they eventually realized that they were cannibalizing their own audience, and also just creating some marketplace confusion.

You have to be careful with it as you create these other brands, especially when people are not necessarily consuming online content that’s brand-specific. People are often entering through search engines or they’re entering through social. They’re not thinking so much about the brand that they’re reading. You need to do the best job you can with whatever small amount of time that you have of somebody’s attention. Try to establish who you are and encourage them to come back. The more you spread yourself thin and confuse your brand, the less chance you’re going to have for that.

As you brought up some of the things you thought about changing and doing, you mentioned women entrepreneur. You had it and you’re thinking about doing it again, what’s the challenge with that? I’m curious.

There are a couple of challenges. One was similar to the co-brand challenge. When we had Women Entrepreneur, we were raised this question, “Here’s a great story about a woman entrepreneur, does it always have to go on Women Entrepreneur? Can’t it go on” If they’re all going to Women Entrepreneur then becomes just a site for dudes, and we definitely don’t want that. That’s a challenge by itself.

[bctt tweet=”A brand is a simple, repeatable thing that has an identifiable way of fitting into somebody’s life.” username=””]

How about a section? Women Entrepreneur as part of Entrepreneur, have you done it that way?

You can but that’s not how people search and consume. If you’re doing it online, people aren’t generally aware of or care about what section of the website they’re in. It has to have some purpose. That purpose has to be both for readers and as service for readers. Let’s be honest, there’s also a sponsorship purpose if you’re creating an environment that sponsors want to be a part of. Another thing that we did was when we started Women Entrepreneur, we created a product inside of it called, Ask an Expert.

Originally, the idea was to fill it with amazing women who are in various capacities, investors, serial founders, etc. People who other women in business could contact and ask for advice from in an easy one-on-one video conferencing formats. It’s essentially a consulting service that you could buy 30 or 60 minutes of somebody’s time. It was great but we were looking at it and we’re also saying, “Why exactly is this only available to women?” There’s nothing gendered about this. Ask an Expert evolved out of Women Entrepreneur and it became a product that’s for everybody.

These are the challenges that you have when you start building these things out that are designed just for one audience. We do have a lot of dedicated coverage focused on women entrepreneurs. For example, our October issue is always our 100 Powerful Women list. That’s where we closed not long ago, and it’ll be out in October. Of course, we’ll be doing a lot of online coverage around that issue. Those things are great because the community of women in business is extremely strong and robust. Women in business love supporting and championing other women in business.

We want to be a place where that happens, and where we can encourage that, and also share the greatest ideas from everybody. I have found consistently that when you carve out an area on a website, sometimes you can create great things but a lot of times you just create confusion. Entrepreneur like everybody else has gone in different directions and then figured out what was good about it and what was not, and then came back to the main part and brought the lessons with them. We just go over and over again doing that.

I hear what you’re saying. It is a challenge and you have to look at your readership. The 100 Powerful Women is interesting. The reason I’m even focusing so much on women is I have to give a talk to women about the value of curiosity. I’m curious about your 100 Powerful Women. What makes them a potential for your list?

Here’s the thing about lists. Unless it’s the Inc. 500 or 5,000, or whatever it is, which is based on one number, it’s just a growth number. Otherwise, every list like the ones that we do, Fast Company has the Most Innovative Companies and the Most Creative People, there’s no way to quantify this. There are no numbers, there’s no algorithm, it’s not possible. Instead, what we do as editors is, we ask our network of writers and everybody internally to produce a bazillion ideas. Everyone who they’ve talked about or talked to, everyone who they’ve read about, everyone who they feel like is part of the conversation right now.

We generally think of it as about a twelve-month. Within the last year, who’s had a substantial impact? Who’s done something interesting? Who is someone who represents in some way where businesses are going and all the good things about it? We then get this long list and we whittle it down. What we ultimately want to create is a survey of greatness. It’s not like we found 100 people and that there was the 101st person who we’re not good enough. It doesn’t work that way.

Instead, what we’re trying to do is make a statement about, these people represent business now. In this case, the most interesting, innovative, influential, supportive and thoughtful women in business now. That’s the best that we can do. I know that people will read these lists and everybody always has thoughts on them. I’m sure a lot of people, their thought is, “Why am I not on the list?” They can’t appreciate that. The bottom line and I want to be upfront, is that there’s no possible way to quantify power. We do not have an algorithm. What we’re trying to do is we’re trying to make our best statement about the ideas and people who represent what matters now.

That’s such a great explanation because it’s tough. I was coming up with a list for my talk. I was looking for women leaders who embraced curiosity. It was fun to look and see some of the top names. There are a lot of CEOs of IBM and big companies who were female, who had done these amazing things to improve curiosity within the company. We all know Oprah and those types of people. If you look at what they say, what made them successful, all of them are listing either openness, asking questions, listening, curiosity or empathy. The things that tie into the same stuff. I’ll be curious to see your list to see what kinds of things are they working on.

As part of my work, I went to London for the Thinkers50 group. I was impressed by how many of those were smart women. A lot of them have been on my show who’ve had their work recognized for being ideas to watch in 2020. Everybody’s got these lists of where everybody stands. There’s so much that we can learn from all the content. You’ve worked for some of these major publications who share some of this great content. I’m curious if there’s a big difference in working for Entrepreneur as compared to working for maybe Men’s Health, Fast Company, Maxim, or any of these other magazines? Is it a similar experience or is it completely different if you work in one place versus another?

TTL 757 | Change
Change: When we think about personal brand, people often get hung up on the word “personal.” That’s the wrong word to focus on. The focus should be on the word “brand.”


Some of it is different and some of it is the same. First of all, a thing to know about magazines is that the majority of the people who work at a magazine, let’s say in editorial, aren’t necessarily of the world that is being covered. I worked at Men’s Health for a couple of years. I’m not a bodybuilder. My abs are nothing to speak of and yet I was there. For that matter, the Editor in Chief wasn’t of that world either. He had done a good job of writing or co-writing books that spoke to that and then getting himself on TV all the time. He had become a face of it but he wasn’t hitting the gym and bodybuilding or whatever. That’s an important thing to know. That is true regardless of where you are.

At Entrepreneur, there are a lot of editors who are interested and knowledgeable about business but are not necessarily business owners themselves. In that way, there’s something similar about it. What I like about Entrepreneur, which is different from other places, and this is one of the reasons why I ended up at Entrepreneur was that when I was at Fast Company, and then I was at Men’s Health, these are brands that had an established idea of what they were and what they wanted to be. My role was to show up and carry the ball. That’s fine in the earlier parts of my career where I’m learning.

I come into Men’s Health, I’m pretty young. I’m given a section to work on and my job is to learn how this magazine operates, and to learn from the people above me. There’s also little room at a magazine like that, at least at the time that I was there, to evolve it, to propose ideas that were radically different. Everything happened in the margins at that magazine. Eventually, I got comfortable enough with my skillsets and started to feel like I wanted what I eventually heard referred to as a molten environment. Michael Dubin, the founder of Dollar Shave Club had said that in a story that I had run about him where he likes molten environments.

I read that and I was like, “That’s exactly what I wanted too.” I wanted a place that I could come in and shape. I wanted a place that needed me more than I needed it. The moment that I happened to find Entrepreneur is when they reached out to me. It was a moment in which the magazine has been doing its thing for a while, and was in need of a refresh and everybody knew it. That was an exciting opportunity for me, to come in and rethink what was this magazine going to be. Who is it going to be for? I realized as I got deeper into it that the brand had been speaking to people in an old definition of the word entrepreneur.

Entrepreneur being a small business person, but we’re not in that world anymore. The word entrepreneur has now come to mean a mindset and identity. It’s a badge of honor. It’s something that people are attracted to whether or not they fit some traditional small business person mold. People who work inside giant companies like Dell or IBM can call themselves entrepreneurs rightfully so. To me, the definition I came away with was that an entrepreneur is someone who makes things happen for themselves.

This was something that I loved. I have found that to be the case going forward. Entrepreneur is a small company. It’s a family-owned company and it’s pretty nimble. It is open to ideas. We are constantly inventing or being entrepreneurial, which is something that I appreciate. In doing that and spending all my time with entrepreneurs in a more entrepreneurial environment, I certainly started to think of my own career and my own approach to things in a different way.

You bring up some important points because in companies, sometimes they call it intrapreneurs if they’re within the company and they have the entrepreneurial spirit. We were trying to get such great ideas for innovation and to have people more engaged. That’s what I’m trying to help people with developing curiosity. What you’re talking about is opening up the field for many people to think like that. Even though you work for Entrepreneur Magazine, you’d probably consider yourself as an entrepreneur.

Absolutely and I do have, for what it’s worth, my LLC where I’m producing things. I have a whole bunch of stuff on the side. I do think of myself as an entrepreneur. A big part of that is that I think about building strategically in a way that I didn’t before. When I was at these other magazines, I would do what most journalists do, which is going to create something, put it out in the world, and move on to something else. Now, I’m focused on strategically building and making sure that everything that I do is part of a cohesive whole.

You do a lot of things. You have three podcasts. You also wrote a novel with your wife which I thought the content was interesting. The name of the book is Mr. Nice Guy. Do you want to say what it is about?

Mr. Nice Guy is a romantic comedy. You’re not going to expect what I’m about to say next, it’s about two people who each week sleep together, and then critically review each other’s performance in a magazine. That was an idea that I had in my twenties and I tried to write it a number of times. I couldn’t figure it out, then wouldn’t you know it, I married a novelist. After my wife, Jen, sold her novel at the time, she was trying to figure out what to do next. I said, “Why don’t you write my book because I’m never going to write this thing.” We both think it’s a funny idea and she said, “Let’s do it together.” We spent years on it. It was about a three-year process.

That three years happened to span a rather significant number of changes in my career. When we started, I was at Fast Company. I hadn’t established myself as a personality in any meaningful way. I was just an editor at Fast Company. It would have made more sense to have this novel come out but then, by the time it came out, I was Editor in Chief of Entrepreneur Magazine. Everyone’s interviewing me about entrepreneurship and then it’s like, “Why did you write this romantic comedy?” The answer was, “Because it was fun.” It taught me a lot. It made me think about writing in a different way. It was also a fun product to market. I was able to take something out to market and experience that. I feel like there were quite a lot of great opportunities that were built into this thing that might seem random.

You’re developing it into a television show.

[bctt tweet=”An entrepreneur is someone who makes things happen for themselves.” username=””]

We are not exactly developing into a television show. We sold the rights. The show was option to some serious production companies that run by accomplished people who have now attached a star and an executive producer. They were about to have a meeting with one of the big streamer networks and then COVID shut everything down. We’re waiting for word on that.

That’s awesome, though. Congratulations. That’s pretty tough to sell your idea like that. It’s a cute concept. I love that idea. I want to see how they stay married after that.

It was written by a married couple but the two people in the book are not married. Certainly, the state of their relationship is at stake over and over again.

That’s a great concept and everything you do is fascinating. It resonated a lot. I have my podcast, my writing, and my different things. I saw that you did a lot of the same kind of speaking and things that I did. I knew we’d have fun chatting. I was looking forward to having you on the show. I love that you’re trying to inspire people to change. I hope you tie curiosity into your message because to change, we all have to have that spark and try and build that. I enjoyed hearing about all the things that you’re working on. A lot of people know how to find you at Entrepreneur Magazine. Is there any place else you want them to follow you on social media, that type of thing?

Thanks a lot for having me. This was such a fun conversation. I’m active on LinkedIn and also Instagram. On Instagram. I’m @HeyFeifer. I respond to all DMs in case anyone wants to reach out. Speaking of change, why people resist change, and how to embrace change, that show that I talked about. Pessimists Archive. It’s a show about why pessimists of the past were wrong in how to be optimistic about the future.

I’ll give you a couple of teasers. Why was there a national complete moral panic in 1907 over teddy bears? Why have multiple leaders, including the King of England and the Governor of Mecca tried to ban coffee? Why were novels considered dangerous? These are the kinds of things that now we think of these things as wonderfully commonplace and a good part of our lives. Back then, they were new, scary, and terrifying. It’s worth understanding what was going on back then and how to overcome it. Once you do, you’ll start to see technology in a different light.

A lot of people may have caught that documentary The Social Dilemma on Netflix where Tristan Harris looks directly at the camera and said that “Nobody ever said that the bicycle was going to be the end of humanity.” That’s absolutely false. Lots and lots of people said the bicycle was the end of humanity. Tristan Harris doesn’t understand history. It’s important to understand history because you can’t appreciate change if you don’t study it. Again, it’s called Pessimists Archives.

You could tell being and or the Editor in Chief that you’re great at creating hooks to get people interested. Those are wonderful. Thank you so much, Jason, for being on the show. It’s so much fun.

Thanks so much for having me. This was great.

You’re welcome.

I’d like to thank Jason for being my guest. We get many great guests on the show. If you have missed any past episodes, you can go to to find them. We air on all the podcast stations and the AM/FM stations listed on the site. On the site, you could find out more about the Curiosity Code Index and the Perception Power Index. Both of them are available on the site where you can drop down the assessment’s menu to find them. Anything about cracking the Curiosity Code and the Power of Perception you can find on the website. I hope you check it out. I hope you’ve enjoyed this episode and I hope you join us for the next episode.

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About Jason Feifer

TTL 757 | ChangeWe are in a time of constant change, and many people’s instinct will be to resist. We prefer comfort over change. But here’s what I know: The most successful people in the world don’t see change as something to stop. They see it as an opportunity to embrace.

  • That’s why my mission is to help people make the most of change. I do that through:
  • Entrepreneur magazine, where I’m editor in chief
  • Keynote speaking, which I’d be happy to discuss for your next event
  • Pessimists Archive podcast, a show about how change happens, which goes back in time to see why people once opposed the things we love today
  • Problem Solvers podcast, a show about entrepreneurs who adapt and solve problems in their business
  • Hush Money podcast, a show that opens up conversation about taboo money topics
  • And more.See more, and get in touch:

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