FMC Fast Chat with Jason Feifer, Editor in Chief, Entrepreneur Magazine

Coming up next is FMC Fast Chat with the quick-talking editor-in-chief of Entrepreneur Magazine, Jason Pfeiffer. This episode is packed with quick tips, so get ready to take some notes.

FMC Fast Chat takes you inside the news so you can be in the know in 30 minutes. Hosted by Fair Media Council CEO and Executive Director Jaci Clement, Fast Chat features notables in news, media, and business.

And today we get to chat with Jason Pfeiffer, editor-in-chief of Entrepreneur Magazine and host of the popular podcast called Build for Tomorrow. So we want to talk to him about that as well. Jason is one of those guys who gets you excited for the future and likes change and likes to talk about change. So we're excited to have him with us at this point in history because right now, thanks to the pandemic, everything is about change. So Jason, first up, thank you so much for joining us today.

Thanks for having me.

I appreciate it. So why don't we kick off by getting right into it, which is, is it or is it not a good time to be an entrepreneur today?

I mean, I think that it's always a good time to— sorry, I hear possibly a little feedback. Sorry if anybody's hearing garbage that isn't just like me talking. I think it's— listen, I think that it's always a good time to be an entrepreneur in that there is never a perfect time. There's never an easy time. And being an entrepreneur is a very hard journey. Entrepreneurs like to say of themselves, just as people in the media like to say of themselves, that if you could do anything else, go do that because it's easier. This is a difficult journey. People bond over the difficulties of that journey. But I will say that historically speaking, people tend to go into entrepreneurship in larger waves when there is some moment of crisis. I mean, we have seen in the past year a 10-year high in new business applications. And the last time we saw something like that was the Great Recession of 2009, which shifted an entire generation into entrepreneurship. And I think people come to realize that the only person that they can rely on to really build and support themselves is going to be themselves. And they're watching people get laid off around them. They're watching well-played or well-carved career paths get completely demolished. And they say, you know what? My own journey is not going to be easy, but at least it'll be mine.

Right. Okay. All right. So let's tap into that though. I mean, to be an entrepreneur today versus say 2009.

Sure.

What skill sets do you need to be successful today?

Well, let's— I mean, I think that the more— I think the skill sets remain the same. What has changed significantly from— and I'll identify what they are— what has changed significantly from 2009 to now is resources and tools and platforms that are available. I mean, there are so many ways now to build a business as a solopreneur. You don't need to, you know, you have an infinite supply of companies that'll handle your fulfillment. You can outsource, you can find the outsourced CMO if you want. There's no end to the kinds of products and services that are being developed. And now as we move into the no-code movement, where people can build things without any technical expertise at all, I think that it's only going to become even easier to outsource all of the garbage stuff that took so long and were barriers to entry for people so that people can come in just with their idea and really focus on their special skillset and how to connect to their audience. So what do you need? I mean, look, most people who I talk to, even people who are wildly successful, started knowing absolutely nothing. I just spoke To— I mean, just to kind of put a fancy face to it, I just spoke to Ryan Reynolds because he was on the COVID of our March issue. And Ryan went from being an actor, which of course he still is, to owning a number of different companies and also starting a marketing agency called Maximum Effort, which has done extremely well. And he's very open about how little he knew about any of this when he went into it. And the line that he used that I love, which I think is something that all entrepreneurs need to embrace, or even aspiring entrepreneurs, is You can't, this is, these were Ryan Reynolds' words, you can't be good at something unless you're willing to be bad.

That's good.

Reid Hoffman, the co-founder of LinkedIn, likes to say that if you launched your product, if you weren't embarrassed by your first product launch, then you launched too late. The idea being that everyone has to just get something out there and then learn from it. There's no possible way to sit on the sidelines and incubate something until it's like a full-grown perfect thing and then put it out into the world. So what do you need? Most of all, you need adaptability, you need, a coolness in crisis. You need a willingness to learn, and then you need to be a constant learner because what you will learn from the— for the first 6 months of your journey is, is just the very beginning. And you're going to need to be a curious person of the world who's willing to evolve themselves and their leadership style and their idea along the way.

Okay, and I'm curious, from your perch at Entrepreneur, are you, are you seeing particular areas that entrepreneurs are gravitating toward? Are there any particular trends happening right now?

So I hear people who speak of trends, but obviously these are subsets of things. So I'll give you an example. There's been a lot of talk in the last couple of years among very smart people who I know, who talk about the growth opportunity in really boring and unsexy things. So you're coming out of a time where So many people made billions of dollars making people's lives incrementally more convenient, the Silicon Valley app economy.

Okay.

And that's not to say that that's going away, but I think that in reaction to that, I started to hear a number of conversations of people saying, you know, the real exciting opportunity here is actually in the stuff that nobody has tried to innovate in a very long time, stuff that's difficult and boring, stuff like, transportation and logistics and insurance. These are things where there's actually quite a lot of opportunity to get in there and to start thinking big, and where there's a lot of white space because the players are all very old and haven't innovated in a very long time. I mean, you think of SimpliSafe, for example, who came in with the shocking idea of home security devices that are remote so that you don't have to wire things through your walls. They came in, they weren't even trying compete against those companies. SimpliSafe originally started as an idea for renters in apartments, but there was such a desire among homeowners, who they weren't originally targeting, because homeowners otherwise were just dealing with this old incumbent industry that wanted to come in, punch holes in your wall, and run these wires. And people were like, this is garbage. So there's, I mean, that is not a sexy industry, home security, but it's where there turned out to be a gigantic opportunity. And so that's all around us. That's everywhere.

Okay. Where would you say education falls today?

I think it falls into that category of under-innovated, but also exceptionally difficult. And I think, you know, and you've seen, we've seen so many education startups rise and fall. And I think the reason for that is because unlike home security, where people don't feel People don't feel, I mean, I use the word safety. People don't feel safe by holding on to an older idea of wires in their home, right? People are very happy to walk away from the established idea of what home security looks like, as long as there's a better solution. People, a lot of people feel very attached to an older idea of education. They feel like, well, it's hard to, how are you gonna tell me that you've got a replacement for higher education? Maybe you do, but the rest of the world still values this degree. degree. And I'm not sure that I'm really willing to take a bet on that for myself or for my children or so on. And so I think because education has such a, has such a hold on us in terms of the old way of educating people has a cultural value that I don't think top to bottom is yet to be rethought. I think that it's become harder for education startups to really enter that space, unless we're talking about just like online learning and career supplementation and stuff like that. I do think that it's coming. And I think that the last year with the pandemic and the way that it shook people's understanding of higher education is going to get us towards there. And I do think that there ultimately will be massive, massive opportunity here, but you know, you're going up against an incumbency that's very hard to beat.

Okay.

Yeah.

And one of the other things we're seeing too, so we're in New York, you're in Colorado. So I don't know if you see things differently. If so, please let us know. Is You know, the thought process right now is maybe people will not be returning to work the way we used to work, that I can live anywhere now and do my job. Do you see that happening as some people are predicting, or do you think it's going to be more of a hybrid?

So I think it's going to be a hybrid. And I think that the history of innovation bears that out. So I'll tell you a quick anecdote that has absolutely nothing to do with what you just asked, but actually will inform it very well.

All right.

So this comes from— you'd mentioned that I have this podcast called Build for Tomorrow, which is a show about the things from history that shape us and how we can shape the future. So I love looking back at why people were afraid of innovation throughout time, because it tells us a lot about patterns of change and what we can learn for now. So one of my favorite pushbacks throughout time was in the early 1900s when the phonograph came out, this first recorded music technology, the first time that you could bring a record home, bring— not just a record, bring any form of music home and have it played to you, where you, you could hear music without a live musician. Right?

Mm-hmm.

It was a radical idea. Throughout all of time, the only way that you could hear music was if a person was in front of you playing an instrument. And then suddenly there was a machine that could do it. It could record these people and then it could play it at any time. It was Mind-blowing! And many musicians at the time were deeply offended by this. John Philip Sousa, who every— you may not know his name, but you know his music. He wrote every famous march. Da da da da da da da da. Right, John Philip Sousa. So John Philip Sousa, he railed against recorded music. He refused to participate in it for decades, and he made all these really fascinating arguments against it. And one of them, my favorite, goes like this. So he says, if you bring a recorded music technology into your home, then people will no longer play music live, because why would you do that when you have the machine? So now that's the end of recorded— that's the end of performative music in your home. And that means that mothers will no longer sing to their children, because why would a mother sing to their child when they have a machine And because children grow up imitating their mothers and the mothers are no longer singing, instead they're using the machine, the children will grow up to imitate the machine. And therefore we will have a generation of machine babies. That was his argument. Now, what is—

He didn't overthink that at all.

No, he didn't overthink it, but that's what we do. That's what we do. I mean, if you watched The Social Dilemma with Tristan Harris on Netflix, you just saw that argument. It's the same argument that plays itself out. I see some kind of change and therefore I'm going to extrapolate the loss without putting any thought into what the possible gain is. That's how we operate. So that's, that's if you watch The Social Network, that's what you saw. And so here's, here's what's happening.

Mm-hmm.

People, they focus on loss, they don't understand gain, and they think that one change means extrapolated permanent change. So if you introduce something new, it will wholesale replace something old. That's a— that's a pattern throughout history. We're experiencing it now. We've experienced it before. But that's never true. It's never true. Instead, what happens is that we don't replace the old. We integrate with the old. Something new is introduced, and we find out where the new thing fits into our lives and where the old thing fits into our lives. So do I play— let's fast forward today with Susan's example. Do I play songs on Spotify for my children? I have a 5-year-old and a 2-year-old. Yes, I do. Do I also sing them a lullaby at night? Yes, I do. I do both.

That's great.

And so this is what— this, like, the premise of your question, which is something that people are asking a lot now, which is, well, now we've gone to remote work. We have this new technology. We've always had it, but now we've embraced it. And now are we only going to be remote? That is based on an assumption that when something new comes along, it wholesale replaces the old. And that's not how things work. So instead, I think that we're going to see a mixture. And there are going to be some companies that are fully remote. There are some going to be some companies that are fully back in. There are going to be some companies that are going to be a mix. And I think everyone's going to make a decision based on what's best for them. The great thing that we have now is more options that we're willing to collectively take seriously. And I think that's a good thing.

Tell me a little bit about— because this is an argument I've heard over the years— the difference between an entrepreneur and a small business person. How would you define the differences?

Well, so I think that the answer to that question is different now than it might've been 10, 20 years ago, because the definition of entrepreneur, culturally speaking, has changed. So if you went back 10, 20— I mean, Entrepreneur has been around, Entrepreneur Magazine, Entrepreneur Media has been around for, I think, 41 years, 41, 42. And I'd say that for the majority of that time, people probably intertwined the word entrepreneur and small business person. They thought of them, if you're an entrepreneur, it means that you're in business, you own your own business, and it's a sort of certain phase of your business. And now, I think, particularly within the last decade, I think that that has changed. And I think that the word entrepreneur now is a cultural identity. It is a badge of honor. And it means, and this is how I define it, it means someone who makes things happen for themselves. I don't think that you have to own your own business to do that. I mean, someone might call you something different. They might call you an intrapreneur if you're entrepreneurial, but you're inside a large company. But I think that the methods and the thinking still stands. And it's the reason why I love— I just looked over to just sort of like have a prop. It's the reason I love when somebody tells me that they picked up Entrepreneur Magazine and they're like a teacher. I get these emails all the time. And it's like, hi, I'm a 7th grade math teacher. And I was sitting at the auto body shop and I had nothing to do for 20 minutes. And I picked up this magazine thinking there would be nothing in it for me. And in fact, I read it cover to cover and I loved it. And the reason why that's happening is because I've made this magazine about thinking. There's so much thinking that happens in entrepreneurship. Entrepreneurship is about problem solving. And that's something that transfers way outside of any traditional small business or any other kind of business ownership. So to me, small business ownership, I mean, you could debate like, what exactly does it mean? How many employees and what's your revenue and blah, blah, blah. But we understand, generally speaking, what we're talking about when we say small business. Entrepreneur, I think, is just— it's just way broader. It applies to, I think, anybody who has a mindset of entrepreneurship.

Okay, I do want to touch on the magazine, but before I do that, I don't want to forget this question, which is, who do you think are the best thinkers on entrepreneurship today? Who do you turn to?

Oh, like, just like individual people? Um, well, that's an interesting question. I mean, I quote Reid Hoffman quite a lot, uh, because he is really good at thinking through the, the tenets of entrepreneurship, but at the same time, he also has really catchy phrases which are really, really good to remember. repeat. If you're not embarrassed by your first product launch, you launched too late. Another one that I love, which he uses all the time, is entrepreneurship is jumping off the cliff and building the airplane on the way down. And so I really love his work. Personally, I've been fascinated to get to understand guys like Gary Vaynerchuk and Tim Ferriss, because they're so good at understanding how this audience thinks and what kind of encouragement and mindsets they're looking for. And so while they're kind of different kinds of thinkers, both of them, I've been fascinated to, you know, it's been fascinating to listen to that. And then, you know, I just, I like flipping through. I mean, I'm looking off to the side at what I've got. I mean, you know, this guy Greg McKeown, who wrote these 2 books, actually I have both of them literally sitting by, Essentialism and And Effortless. I find these to be really interesting because they are essentially simple ideas that are drilled down to so deeply that they offer these really tangible, actionable insights for entrepreneurs about simple things that people often forget, but that I think are really important to remember. Oh, and then I'll shout out one more, which is Which is Ben Horowitz from Andreessen Horowitz, who's written, you know, a couple books that are, you know, very interesting. I've talked to him and really enjoyed that.

Yeah, we actually did do a podcast with Gary Vee, which was great fun. Yeah, he's a great thinker and a serious hustler, even as a little kid. So let me ask you, thinking about that, when you were 5 years old, what did you think you'd be when you grew up?

Oh, I mean, at 5 years old, I don't know the answer to that. I can tell you that Once I gained more of a conception of what I, what was in the world, like what does a job really mean? I really wanted to be a writer. And I spent the bulk of my career, I, in high school, I was writing for local music magazines. In college, I took over the local, I mean, I took over the student magazine. Right after college, I got into community news. I was a local news reporter. I worked at 2 local newspapers. I went to Boston Magazine. So I was in regional magazines, then I went into national magazines, and I bounced around. And I have always thought of myself, really until very recently, as just a pure journalist. And to me, my hustle was, I'll get a job as an editor because that's where the jobs are, but then really I'm going to use it to be a writer, which is what I'm far more interested in. And then at Entrepreneur, I started— when I became editor-in-chief of Entrepreneur, people started treating me differently. And I don't mean like, oh, fancy pants. I mean like, they didn't understand— my audience, when I would go out to meet them, didn't understand me as a journalist. They understood me as a thinker and advocate for entrepreneurs. They had no idea that I had a journalism background. It wouldn't have occurred to them that I had a journalism background. And at first, that was disorienting, and I didn't really know what to do about it. People would have me on their podcasts, and they would talk to me as if I was something other than what I was. And I was very uncomfortable, and it took a long time for me to calibrate to that. But what I eventually realized was that there was actually a massive opportunity in understanding that, an opportunity for me, frankly, also an entrepreneur, an opportunity for entrepreneur, because I could go out and I could advocate and speak in this way, in a way in which, I mean, if we had talked 5 years ago, I couldn't have done this interview the way that I'm doing now. I wouldn't have had the confidence in saying, I am a speaker for this group of people. Instead, I would've proposed myself just simply as a journalist. Here's who I've interviewed. Interviewed and here's who I've— but no, I've embodied and ingested this. And I have found that the results are tremendous. I discovered that there was tremendous opportunity for myself, for Entrepreneur, in really leaning into that and understanding how to serve that role. But frankly, also, and this is what really excites me, is that there was a lot of opportunity to help people. Because, you know, whatever, being a journalist is fantastic. And I value that experience so much. But being someone who people turn to for answers, and who I feel really good about the answers that I have, because I've spent so much time getting to know the way that really smart people think, and also spending all this time studying the history of innovation and pairing these things together, I'm making— I feel like I— and not just feel, I see that I make an impact on people's lives. And the way that people reach out to me and the conversations that I have with folks. And that's, you know, I just have to say, that's That's been more exciting for me at this stage of my career than just being a pure journalist.

Oh, good for you. So tell me a little bit about what's happening at the magazine, because one of the, one of the big issues facing all media, you know, in recent history is the changing business model.

Yep.

So how, how are you able to pay the bills and keep going? And what do you look to toward the future? In terms of what your model will look like?

Yeah, it's a great question. So we, I mean, we're very fortunate in that we are speaking to an audience that a very wide range of advertisers wants to reach. And so, so we're actually really in growth mode all over the place. I mean, the print magazine is growing both in readership and in revenue. Online, we're seeing the same. So like, all of that stuff is really great. Like, if I was, if I was the editor-in-chief of I just don't know, like a general interest news magazine, I'd be a lot more worried because there's so many ways in which people can get that stuff. But Entrepreneur really does own a space that is very healthy. And so that's good. But of course, we're not going to rest upon that. Nobody should rest upon what used to work because eventually it's going to stop working.

Right.

And so what we're now doing is we're exploring and starting to roll out a lot of different products and services that we can use to help entrepreneurs directly. Well, a lot of the conversation that we have internally is about how for most of this company's history, we were really a broadcaster. We would create something and we would just sort of send it out into the world. And now we want to be a direct helper. We want to be in touch with people and helping them. And I think that that tracks with what the media industry at large is going to need to be thinking about, because to me, I'm obsessed with this question that I always ask of everything around me and everything that I do, which is, what is it for? What is it for? And the answer— because the answer will change. And so if you think about content, what is content for? Well, for most of media's history, frankly, what content was for, aside from obviously serving an audience, what content was for was for monetizing. You would either sell subscriptions to it or you would run ads against it. That's what it was for. Now, that is increasingly not the answer because you— which is a harder— you could have a harder time monetizing it. Right? People don't want to subscribe to as many things. And, you know, the Facebooks and Googles of the world are eating the majority of ad dollars. So there's like less and less to be spent against content. So what is content for? Well, I'll tell you what it's for. It's for relationships. That's what it's for. Because when you put out great content, and I despise the word content, but I don't have a better one. So I just want to say that.

Right. No, I'm with you on that. I understand.

Like, we need collectively to come up with a better word because I hate the word content. But anyway, because I don't have a better one, content, we put out great content and our readers or viewers or listeners or whatever, they get value from it and therefore they trust us. And when they trust us and they have that relationship, that lasting relationship, well, now you can figure out what products and services can you sell people, make their lives better, that they will buy because of the trust that they have Because of the relationship, because of the content. So that's, I think, how people need to start thinking, and that's where we're shifting towards.

Okay, we do have a question here on whether or not you think a niche publication, um, is a strength these days. So more of a specialized interest versus the, the broader mainstream media approach.

Yeah, I think, I think absolutely, um, because look, the, the broader that you have to go, the more you are playing against everybody else who's playing the same game. And you see that in digital publishing right now, that if Elon Musk says something crazy, which, you know, give him 5 minutes.

He will. Yeah, exactly.

Like, that story is— obviously, it's going to show up on Entrepreneur and all of our competitive— our whole competitive set, but it's also going to show up on Time, and it'll show up on Newsweek, and it'll show up in the Times, it'll show up in Marie Claire, it'll show up everywhere. And so what are you doing at that point? You're chasing the clicks. And there's— that's something to be said for that, because that's the business model, but you're not building a relationship off of that. And I think that that's a losing game in the end, because you're just— all you're doing is playing to an algorithm, but you're not building a relationship with an audience. And if you're not doing that, then what the hell are you really doing? But if you're a niche publisher, if you understand your specific audience really well, and you are the only or one of just a handful of people who are really serving that audience, I think you have a tremendous opportunity to continue to grow that relationship and then figure out other ways to serve that audience. And you just don't have the same kind of competition and you don't have to do the same, like run to the basement with the same garbage just to keep yourself afloat. You can really focus more on quality. And I think that's great.

You know, historically, one of the weaknesses with media in general is how little it understands its audience. And I actually did just see another survey just this past week reiterating that fact. And we see a lot of publications now that are moving toward newsletters as a way to be more personal. What kind of advice do you have for businesses in general about how do you get to know your audience? How do you get to understand them?

I mean, this is going to sound as simple and stupid as possible, but you talk to them. And you talk to them in really specific ways. You get to understand what it is that they need. You get to understand what you're failing at. I'll give you a perfect example, just a personal example. So for years, since 2016, the podcast that I ran was called Pessimist's Archive. Build for Tomorrow used to be called Pessimist's Archive. And that was because there was a popular Twitter handle called Pessimist's Archive, and I partnered with the guy who started it. And we built this thing out, and we had a really good audience, and it was a lot of fun. And then I hired a consultancy, called Penn Name. They'd built Tim Ferriss's podcast out. And I don't know if they built it from scratch, but they were a big part of its growth. And so they did this audience insights project where their audience insights person, this woman named Rochelle, spoke to a ton of my listeners. And in this very strategic way in which she was getting to understand what was What do they like? What do they not like? What was holding them back from being a bigger advocate of the show? And we learned a number of things. And a couple of those things were, one, the name was a barrier to entry. If people originally heard the name, they didn't like it. They thought it was a pessimistic show, which it isn't. And they wouldn't listen. Or if they finally got over that and they listened, they had a hard time getting their friends to listen for the same reason. And also, I learned that they were getting something out of the show that I didn't realize they were getting, which is that I thought of it originally as a history show and a kind of interesting exploration of history. They said that the reason that they listened was because it helped them feel more resilient about the future. That was a mind-blowing insight.

Mm-hmm.

And it helped me change the way that I talked to my audience. It helped me change the name of the show. It helped me then sell a book based on the show, which I just did to Penguin Random House. And it helped me calibrate how I'm writing those scripts and choosing the subjects of the episodes, all because I had somebody who spoke directly to my audience, had conversations with them, and not just anecdotal, and they really dug into not just what they liked, but what they didn't like. And so we need to be doing that constantly, constantly. And I don't think that we do it enough. We often think that if we put in media— I'm speaking of media now— if we put something out into the world and people respond to it, then that's That's conversation. That's not conversation. That's not what it looks like. You need to be having very active, engaged, deep conversations with your audience. It's the only way to go forward.

We actually have to wrap up. So I've got 2 quick questions for you. If the definition of entrepreneur has recently changed, what is the definition of success today? I think— and the other question, the other question is, you ready?

Yes.

What's the best part about being Jason Pfeiffer today? Oh boy.

So, so the first— to the first one, I know there's a very interesting conversation happening right now about how culturally we've made a mistake by trying to define success too narrowly. Where that— where you see that conversation happen a lot is in higher ed. There's been a lot— there's been a shift away from people going into the trades, for example, And instead going, you know, going into great student debt by going to college because they were told that the only pathway to success is through college. And meanwhile, you have all these fantastically paying trades jobs that are unfilled. And so I think that on a cultural level, and also as an individual level, we need to define success for ourselves. I think we really get into trouble when we think that there is one definition of success that we have to move towards. So I don't mean that as a punt, but I really mean that as, I think that that question is a good one, but can be dangerously answered. And so I want to put it back to the individual and say, you have to define success for yourself. And then what's the best part of being me? Boy, it's hard to answer that. I mean, look, I'm fortunate in a million different ways. So I could just list them all off, but I guess career-wise, what's the most fortunate part about being me, it's that people will talk to me. It's that I can get anybody on the phone, right? I mean, like, I just like name-dropped Ryan Reynolds a few minutes ago, which is so obnoxious, but I got to talk to Ryan Reynolds. I get to talk to anybody. And that's really cool. That's just, that's not something everybody gets.

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