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229: Embracing Change and Mastering Entrepreneurship: Insights from Editor-in-Chief of Entrepreneur Magazine with Jason Feifer

podcast April 23, 2024

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Jason Feifer is the editor in chief of Entrepreneur Magazine, a nonstop optimism machine, and a widely recognized authority on business and how people navigate change. He is the author of the best-selling book Build For Tomorrow, a startup advisor, and host of the podcast Help Wanted and Problem Solvers. LinkedIn name him a “Top Voice in Entrepreneurship”

Jason has also had decades-long career in national media, which included working as an editor at Men’s Health, Fast Company, Maxim, and Boston magazine, and writing about business and technology for the Washington Post, Slate, New York Magazine, and others. 



  • We always like to give our guests an opportunity to just share in their own words, a little bit about their journey, and how they got from wherever they were to where they are today. So, could you share that with us?
  • So, Build For Tomorrow, a book that focuses on startup advisory, and I just kind of want you to take a little time to share with our listeners, what the book is about? Who is the book targeted towards? And how do you believe the book has been helping others in their different careers and businesses?
  • Now the book focuses on four phases of this change. The first is the panic, then you have the adaptation and the new normal and then that phase where we’re never going back. So, could you just elaborate just a little bit, maybe give an example of each just to kind of cement that information across to our listeners.
  • What are three-character traits that you found has to really be intrinsic to organizations or persons who lead organizations to help them really be customer centric?
  • Now, could you share with our listeners, what’s the one online resource, tool, website or app that you absolutely can’t live without in your business?
  • Can you also share with us what’s the one thing that’s going on in your life right now that you’re really excited about? Either something you’re working on to develop yourself or your people.
  • Where can listeners find you online?
  • Now, before we wrap our episodes up, we always like to ask our guests, do you have a quote or a saying that during times of adversity or challenge, you will tend to revert to this quote if for any reason you get derailed or you get off track, the quote kind of helps to get you back on track. Do you have one of those?


Jason’s Journey

Me: We always like to give our guests an opportunity to just share in their own words, a little bit about their journey, and how they got from where they were to where they are today. So, could you share that with us?


Jason shared that in brief, he started in media, he was a community newspaper reporter fresh out of college. Eventually, he got into magazines, he moved to New York City to work for Men’s Health magazine, pretty different from Entrepreneur, and bounced around to a lot of different national magazines until he got to Entrepreneur. 

And at first, he really treated Entrepreneur like a media project. His job was to do what he had done everywhere else, which was to be an editor and to tell great stories and to think about the media brand. 

But over time, two things happen. Number one is that people because of the title, Editor in Chief of Entrepreneur Magazine, they started to treat him as an authority in entrepreneurship, which frankly, he was uncomfortable with for a while because his background was in media, until he came to realize that so much of business is not about the fundamentals of business, but it’s really about the fundamentals of human thinking, and logic and reinvention, and the kinds of things that he had put himself through in his own career. 

He thinks that we all have to recognize what our incredible skill is, and it’s going to be different for everybody. His belief is that every human being has the same fundamental skill, and that is pattern recognition. 

The difference among us is that some of us are better at recognizing different kinds of patterns, right. And so, his pattern is how people think and how people tell stories and how people understand the world. And he came to realize that by spending an immense amount of time with entrepreneurs, he was starting to absorb their way of thinking, starting to act like that, he’s starting to launch his own businesses, starting to advise startups, and that he could lean into telling their stories, processing their insights in a way that would be incredibly useful for other entrepreneurs. And that has led him to the career that he has now.


About Jason’s Book – Build For Tomorrow

Me: So, I was lucky enough to actually read your article in Entrepreneur Magazine. I think it was the February issue that I purchased when I was travelling, how failure can feel good, and it really intrigued me. So, I reached out to you on LinkedIn, and graciously, you accepted my request and here we are today having you on our podcast. So, amazing. So, in your bio, it was also mentioned that you recently published a book that would have been September of 2022. So, Build For Tomorrow, a book that focuses on startup advisory, and I just kind of want you to take a little time to share with our listeners, what the book is about? Who is the book targeted towards? And how do you believe the book has been helping others in their different careers and businesses?


Jason shared that Build For Tomorrow is a book for anybody who’s going through change, particularly going through any kind of career change though. 

He’s heard from a lot of readers that it applied well to personal changes as well. And the book is rooted in this philosophy that he’s developed, which is that when he meets the most successful leaders and entrepreneurs, he finds that they have all developed a unique personal relationship with change, they understand who they are in times of change, they understand how change can impact them in a positive way. And that unique relationship with change enables them to grow and build in ways that others can’t. 

And he wanted to write a book that distilled the experiences and the wisdom of people who have successfully navigated change and help others with a roadmap for how to do it too. That is just simply the most important thing that any entrepreneur can do is to be adaptable, to recognize that the things that are changing around them are great opportunities, and then to understand how to systematically approach that and that’s the book that he wrote. And he’s had a really tremendous feedback from it, it’s really gratifying.


Navigating Change – Understanding the Four Phases

Me: Awesome! Now the book focuses on four phases of this change. The first is the panic, then you have the adaptation and the new normal and then that phase where we’re never going back. So, could you just elaborate just a little bit, maybe give an example of each just to kind of cement that information across to our listeners.


Jason shared that he found that everybody goes through change in the same four phases listed them out panic, adaptation, new normal, wouldn’t go back. Let’s focus on panic and wouldn’t go back. Panic, you know when you’re panicked, you know when you’re feeling that, you maybe are feeling that right now as he’s talking because something massive has changed in your work, because you feel like your industry is shifting underneath you. Who knows. And the reason why we panic is because decades of psychological research have confirmed what’s called loss aversion theory. Loss Aversion theory is the recognition that our human brains are programmed to protect against loss more than to seek gain

So, when something changes in our lives and or in our work, the first thing that we do is we identify the things that we’re comfortable and familiar with and then we start to think about how we’re going to lose them, we’re acquainting change with loss. And then we start to extrapolate it, well, because I’ve lost this thing, I’m going to lose that thing because I lost that thing, then I’m going to lose that other thing. Now, everything starts to feel like it’s disappearing, now, we are panicking. But you can’t do that forever, you can’t panic forever, it’s too exhausting. 

Eventually, you start to look around and say, well, what do I have to work with. We get to adaptation. We start to build a new normal, a new foundation, something comfortable and familiar, again, a new normal. And then we get to wouldn’t go back, that moment where we say I have something so new and valuable that I wouldn’t want to go back to a time before I had it. 

And he can give examples of that. But the pattern that he’s seeing is that people are often forced into or sometimes are proactively making changes that force them to reconsider the fundamentals of the work that they do. And what they discover is that the way in which they were working before or the thing that they were doing, or the way that they were delivering value to their clients or their customers, that that wasn’t the only way to do it. They thought that it was…..but it wasn’t. 

And in fact, it was a lesser version of a better way to do it that had never been explored because oftentimes people don’t feel incentivized to scrap something that’s working, or that sort of working, and take the risk of figuring out how to build something better.

But when change comes along, when you are disrupted, when you’re forced to react to the things that are shifting around you, you start to ask yourself some really fundamental questions about whether or not the things that you thought wouldn’t work maybe are worth trying. And some of those are going to become the best opportunities for you going forward.


Me: All right, so change. I remember over the years, even going to university and starting my working life and starting a business, I’ve always heard the phrase that change is constant. And I haven’t engaged in the book, I did download it on Audible, and I’ve started listening to it but I haven’t completed it as yet. But what your four phases reminded me of was that change is constant. So, regardless of a pandemic emerging across the world, or kids coming into the play or getting new employees, like change is constant, we’re constantly going through change in different aspects of our lives, so your phases definitely reminded me of that.


Jason stated that that’s something that you can operationalize. 

So, the idea that change is constant is a familiar one for many people. But he thinks often you hear that and you don’t know what to do with it. Okay, change is constant, so what? 

Here’s the starting point. What would happen if you made decisions today based on the knowledge that the thing that you’re working on now will have to change tomorrow? 

What decisions would you make when you know that? 

It starts to shift the way in which you work, you start to for example, do a thing that he calls change before you must where you start to make decisions that are hard today because they will benefit you when things change tomorrow. 

A story that he’d love to tell, he won’t tell it in full here, because it takes a while but divided in the book is of a brewer, a guy who started a Beer Brewery in Delaware named Sam, his company’s called Dogfish. And he had a runaway hit product in a beer called 60-minute IPA, people love this beer, it was on track to become 75% to 80% of all sales of his company, and he artificially limited supply. 

So, this thing was on track to become 75% to 80% of all sales at Dogfish, he capped that at 50% and that meant that people were furious at him, restaurants couldn’t get his beer stocked, bars couldn’t get his beer stock. And he says, “Sam, why would you do that? Why would you limit sales of your best-selling product?” And the answer that he gave me was because tastes change. And he knew that if he allowed this one beer to be a runaway hit so that everybody who ever went into a bar or a restaurant encountered just this beer of his, just this one 60-minute IPA. Well, then at some point IPAs, India Pale Ale, popular bitter style appeals is going to become less popular than it was at that one moment. 

And if people’s impressions of his company were shaped by one beer by an IPA, then he was going to be known as a hot IPA brand. And that’s fine until tastes change, they will change at which point he won’t be a hot IPA brand, he will be an old brand, he’ll be a dead brand. And so, he wanted to do something that was painful today for the benefit of tomorrow, anticipating that change will come. 

And the payoff for the story is amazing, which is that Sam limited sales of his best-selling beer when people would order it, he would try to get them to buy or stock or serve other styles of beer that he made. And as a result, he shaped perception of his company Dogfish not as a hot IPA brand, but as an innovative brand. And you know what you can do with an innovative brand is you can sell it for $300 Million Dollars, which is exactly what he did. 

That’s not something you could have done if he had just thought about how to profit today, how to only succeed based on what was working today. That’s what it means to build the reality of constant change into the decisions that you make today, know that they will require change tomorrow. So, how can you anticipate that and be proactive about it.


Me: Brilliant. I love that story, Jason Awesome! Thank you so much for sharing. 


Essential Character Traits for a Leader

Me: Now, Jason, as Editor of Entrepreneur Magazine, I’m sure that you interface with a lot of CEOs and a lot of business leaders across different industries across the world. And so, I wanted based on your expert opinion and your exposure to persons of this nature, what do you believe are maybe three, it’s a kind of a generic question. But I like to hear from the subject matter experts, three let’s say character traits that you found has to really be intrinsic to organizations or persons who lead organizations to help them really be customer centric, because we’re all about navigating the customer experience. And the reality is, if you don’t have the right people doing the things that your customers want and creating value, you’re not going to have a successful business. And if your customers don’t feel like they’re getting value, and they choose to do business with your competition or not do business with you at all, over time you will not have a successful business. So, it’s twofold and you want that person who can navigate the personalities and navigate as you said, the change and the many different things that will come forth, what would you say are three-character traits that you think someone like that would need?


Jason shared that the first thing that comes to mind was a conversation that he had with this guy Matt, who at the time was the president of Reebok, Reebok the athletic wear company. And he told him (Jason) and this was the first time he’d heard this phrase then he started hearing it everywhere, which was customer obsession. 

He said, “We’re really obsessed, we’re completely customer obsessed at Reebok and we want to understand them, and we don’t want to understand their needs.” And he’s heard that from a lot of people, but he had never heard the next thing that he told me, which was this metaphor that he uses, he says, “Look, we are in a moment in business where quality is assumed.” 

Where if you let’s say, wanted to start a scissor company making scissors, you could not advertise yourself as the sharpest scissors. Because every scissors is the sharpest scissors right? It’s easy enough now to manufacture scissors that every scissors is the sharpest scissors. 

So, if you want to be successful selling scissors, you can’t lean on quality alone. Quality has to be table stakes, quality is what people take for granted, it’s what they expect. The next place that you need to go is who exactly are you serving? 

And how do you relate to them? 

How do you tell a story that makes them proud to use your scissors, that makes them feel like when they use their scissors, they’re exploring a version of themselves. 

That’s what it means to be customer obsessed is to understand the way in which your customers thinks to the degree to which you can tell your story in a way that relates directly to them. 

Now, he’s not telling you something that you don’t know based on serving customers, but that scissors metaphor really stuck with him because he thinks a lot of people, their starting point is, well, because I make the best….. But if you take that away from yourself, and you say, “Being the best at whatever is not enough, because quality by itself doesn’t sell, then what else am I doing here?” 

He has a friend and he’ll make this kind of point number two. Her name is Rochelle DeVos. And she is a Consumer Insights Research Specialist and is brilliant and understanding consumer psychology and has taught him a lot but the framework that she shared with him and again has really stuck with him the most is so much so that he actually has it on his desktop and he’s looking at it right now to read from Rochelle’s thing. 

So, she says, “Look, if you want to understand how to relate to customers, then you need to fill out the following sentence. “When (context) I want solution so that (benefit) from the perspective of the consumer.” So, give you an example that she uses from a compression sock company, a company that makes kind of tight socks for people who have foot pain. 

So, she says alright, when context I want solutions so that benefit. When context, when my feet hurt from standing all day, it’s the context in which there’s a need for a solution. I want a solution. I want to feel comfortable while still looking cute. 

Her example is a company that makes compression socks for women. So, that’s something that they are concerned about. 

So, that benefit, so that I can do my job, be present for my family, enjoy my life while not standing out because of my foot pain. 

What’s so important about understanding this when context I want solutions so that benefit is that most entrepreneurs get stuck at solution. 

They talk about the solution that they have, I’ve made compression socks, I’ve made compression socks for when your feet hurt. 

But the real conversion, the real connection to the audience comes at the benefit. It comes at being able to articulate the value that your customer is going to get from using your solution. 

Customers don’t care about solutions, nobody wakes up in the morning and they’re like, I want compression socks. What they think is I want to do my job and be present for my family and enjoy my life. That’s what they want. So, how do you understand the benefits that they want enough that you can have a conversation with them that is benefit oriented, because that is where you win. 

And Rochelle suggests the way to do this is, is to be constantly in touch with and survey your consumer so that you understand how they think and how they talk and the language that they use. And he finds that perspective to be incredibly powerful. 

So, if we’re making a list here so that you know number one he thinks is to be customer obsessed to the point where you recognize the quality itself is not going to connect to your customer

Point number two is to be benefit oriented, to understand your consumer at a level that is deep enough that they will, that they can articulate the benefit of that consumer is seeking

And if he had to come up with a third one, qualities of leaders who are customer centric.

He’d say that there is a level of inefficiency that leaders are willing to tolerate, to learn from their customers. 

A conversation that always stuck with me is a woman who had started, he can’t remember the name of the company, but it was a paint company, she makes like, really cool paint colors, and it had been quite successful. And the company has grown, it’s actually been acquired, she’s still running it. 

She has a large team, she still is in her brand’s Instagram DM’S every day, corresponding with customers, if somebody DM’S that brand on Instagram, the CEO responds, and that is deeply inefficient. 

But it has helped her stay in touch with her consumer in a way that she feels she would lose if she retracted from that and she just focused on all the operations of the business. 

She wants to be in touch in a way that is inefficient. She has a tolerance for inefficiency, because that is the thing that is ultimately enabling her to understand her customers’ needs today and where those shifts are tomorrow.


Me: Wow, that’s amazing, a CEO that’s in the DM’S. That’s brilliant.


App, Website or Tool that Jason Absolutely Can’t Live Without in His Business

When asked about online resource that can’t live without in his business, Jason shared that these days, he has been absolutely loving Fathom. So, you can get at www.fathom.video and Fathom is a AI note taking tool. 

He has it in all of his calls and meetings now. And it just does a great job of contextually summarizing what was said, provides a transcript, it’s not a perfect transcript, but it’s close enough so that you can go back and find what somebody said, and then it’s very searchable. 

So, he found that to be an excellent way of passively collecting all the information that is being shared and discussed so that he has now a kind of catalogue of it and an easy way to go back and find it. He strongly suggests just having something like this running in the background of all your meetings now. So, again, it’s just www.fathom.video is the company’s website.


What Jason is Really Excited About Now!

When asked about something he’s excited about, Jason shared that he’s been working on a newsletter for the last year, it’s called One Thing Better. And the tagline that he has for it is, “One way each week. One way to be more successful and satisfied at work and build a career or company that you love.” 

And each week is him sharing a strategy. Usually it’s a story that articulates it, and then an exercise that people can use to think more adaptively, to be more open minded, to find opportunities in places you’re not looking, to just feel better about work. 

His wife refers to this newsletter as work therapy. And he’s been just incredibly gratified by the response that he’s getting to this newsletter, it pretty quickly grew to 50,000 subscribers. 

And he just gets these emails from people telling him that they print out his emails, and they keep them on their desk to read regularly, or they forward it to their friends who are struggling with something. 

And he’s so excited to have created something that can have that kind of personal connection. If you want to check it out, it’s www.onethingbetter.email, that’s the web address. And he just thinks there’s a lot of potential in exploring the newsletter space and in creating things that are both connecting with people on a business but personal level as well. That’s a space he really like to live in. So, he’s been excited to be building that and to see where it goes. 


Me: So, we’ll definitely have the link to the newsletter in the show notes of this episode. And I imagine once they subscribe, they can have access to previous newsletters that were published, correct?

Yes, as soon as you visit the website, you will see the back catalogue.


Where Can We Find Jason Online

Newsletter – www.onethingbetter.email 

LinkedIn – Jason Feifer


Quote or Saying that During Times of Adversity Jason Uses

When asked about a quote or saying that he tends to revert to, Jason shared that he’s not big on motivational quotes, he doesn’t get driven that way. But he’s had a lot of people say really impressive things to him that stick with him. 

One of them came from Malcolm Gladwell, who is a best-selling author and podcaster, and so on. And they were talking about work and so on and he had said this line to him which he loved, which was, “Self-conceptions are powerfully limiting.” 

The idea being that if you have too narrow vision of yourself, then you will limit all the opportunities that could come your way, that don’t fit that narrow definition of self. So, self-conceptions are powerfully limiting and that is something he thinks about a lot as he pursues things that takes him out of his earlier conceptions of himself.


Me: Thank you so much for sharing. All right, Jason, we will just want to extend our deepest gratitude to you for taking time out of your very busy schedule and hopping on this podcast with us today, talking about your best-selling book Build For Tomorrow, and the four phases that are connected to that book, also giving us three of the strong character traits that you believe will help leaders to really build an organization that will not just provide value for their customers, but also for their employees so it can be a win-win on both ends. And the insights, the knowledge, the experiences that you’ve shared with us today, the stories, they were just extremely insightful. And I just want to say thank you so much.


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