How I Built My Small Business

Jason Feifer - Unlocking Opportunity with ENTREPRENEUR Editor-in-Chief

• Season 1 • Episode 47

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Jason is the Editor-in-Chief of Entrepreneur Magazine and is widely recognized as an authority on business and adapting to change. He's the author of the bestselling book Build for Tomorrow, host of the Help Wanted and Problem Solvers podcast and has been named a "Top Voice in Entrepreneurship" on LinkedIn.

With decades of experience in national media, Jason has held editor roles at Men's Health, Fast Company, Maxim and Boston Magazine and has written about business and technology for the Washington Post, Slate, New York Magazine and many more.

Connect with Jason Feifer:

Twitter: @heyfeifer
Instagram: @heyfeifer
Facebook: @heyfeifer
LinkedIn: linkedin.com/in/jasonfeifer
Website: jasonfeifer.com
Newsletter: jasonfeifer.com/newsletter

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Website: https://www.annemcginty.com/

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Jason Feifer:

I had absolutely no intention of ever being at Entrepreneur Magazine. I couldn't have even told you Entrepreneur Magazine existed in the world when I first started my career, and it turns out to have been the thing that completely shaped this next phase of my career. So just be open to where the opportunities are, rather than limiting yourself to where you think they are.

Anne McGinty:

Welcome to how I Built my Small Business. I'm Anne McGinty, your host, and today we have Jason Feifer on the show to share insights on embracing change and navigating rejection. Jason is the editor-in-chief of Entrepreneur Magazine and is widely recognized as an authority on business and adapting to change. He's the author of the bestselling book Build for Tomorrow, host of the Help Wanted and Problem Solvers podcast and has been named a top voice in entrepreneurship on LinkedIn. With decades of experience in national media, jason has held editor roles at Men's Health, fast Company, maxim and Boston Magazine and has written about business and technology for the Washington Post, slate, new York Magazine and many more. You can find links to connect with Jason in the show notes.

Anne McGinty:

Before we get started, if you enjoy the show, please hit the follow button on your favorite streaming platform and share it with a friend. I'm an indie creator. I produce these episodes on a budget of less than $20 an episode and I rely on word of mouth to grow and reach new listeners. Thanks for helping me spread the word. Let's get started. Thank you to our listeners for being here today. Jason, thank you so much for coming on the show.

Jason Feifer:

Thanks for having me.

Anne McGinty:

So, looking back and imagine your kids are the ones that are asking you these questions. What would you say are some of the most pivotal and key moments in your life or career that have really led to where you are today?

Jason Feifer:

Oh well, the framing of my kids asking me this question is different from how I usually think about it. Oftentimes, if an entrepreneur is asking me the question or somebody who's aspiring to build a great career for themselves, the first thing that I talk about is what happened at my first job, which was that I was a small town newspaper reporter at this tiny little paper called the Gardner News, north Central Massachusetts, covering nothing like nothing was happening, and I was really bitter after a while because I thought I had a lot of talent and I wanted to write for big places. I didn't even know what that meant. I just wanted bigger and I wasn't getting those opportunities. Nobody was calling me. I wasn't getting recognized in the work that I was doing.

Jason Feifer:

I was starting to feel resentful of my colleagues and eventually I realized something really important, which was number one let's be humble here If I was able to write for the New York Times right now, then that's where I would be, but instead I'm here. So why don't we learn from this moment? But then number two is you can't sit around and wait for people to come to you. They will not. You have to go to them. And I realized the most important thing that I could do right now was actually get myself in front of and start to work my way up to the level of the people who I wanted to impress, the people who I dreamed would call me. So I quit that job and I sat in my bedroom in a dumpy apartment next to a graveyard in a tiny town in Massachusetts, cost me $500 a month and I just started cold pitching. I started cold pitching editors. I got a lot of rejection, but after nine months I started to get into the Washington Post and into the Boston Globe and into the Associated Press. It taught me something that I still use today, which is that they'll never come to you. You always have to go to them, and the alternate route is probably better and faster than the traditional route. I could have sat in that newspaper and got a slightly larger newspaper job and a slightly larger newspaper job and a slightly larger newspaper job, and that was going to be too slow for me.

Jason Feifer:

The alternate route of thinking about the things that are available to me, that no one's asking me to do, the things that I can do technically speaking but are not part of the initial system that I'm in, that is actually the pathway to growth. So that's what I usually say. If my kids were asking me that right now, though, I think that probably the answer would just be trying a lot of things. My kids are nine and five. Especially my nine-year-old really struggles with trying new things. He knows what he likes and he's he's not really that open to the things that he doesn't yet know that he might like, and I am really grateful that my parents, when I was like that, really pushed me to explore, to do new things.

Jason Feifer:

I remember at one point they told me look, we do not care what it is that you pick, but you have to pick something like. You have to pick something Like. You have to go and learn something. It could be anything, but it has to be something, and what I picked was bass guitar, and bass guitar ended up getting me into bands, and it developed this love of music. I don't professionally play bass guitar, but I'm really glad that I did that and I'm glad that my parents pushed me to do it.

Anne McGinty:

You had mentioned, facing nine months of rejection.

Jason Feifer:

Yeah.

Anne McGinty:

How did you get through that?

Jason Feifer:

Well, it wasn't like. It was nine months of straight rejection and then suddenly everything turned right. It was nine months of mostly rejection and occasional successes, and the thing that kept me going was really that I felt like there was a puzzle here and it was solvable, and I just needed the patience to figure out how to solve it. And so I would be cold pitching editors, which, if you don't know what that means, I'm literally coming up with an idea that nobody has asked me to come up with tracking down an editor who I do not know and then sending them an email and hoping that they respond and most of the time they don't, but occasionally somebody does and maybe they tell me this idea isn't right for us, but please try again. At which point you better believe I'm going to come back to you with something next week. At which point you better believe I'm going to come back to you with something next week.

Jason Feifer:

Or a Washington Post editor once got on the phone with me and I hadn't written for the paper yet and she had me explain the story, and then she peppered me with questions, for I mean, it felt like it was 30 minutes, but maybe it was a lot less, but I was so nervous and at the end of it she said well, look, I'm not willing to say yes yet, but I'm also not willing to say no. So if you want to do more work and come back to me, then by all means. And then I was in. I mean, I just dug into this thing. I did so much reporting. I sent her a 3000 word outline for a story that would ultimately never be close to that length, and that was what ultimately had her say yes. And then, once I had her, I could write more for her, I could pitch her more ideas and refine it and just try to tear this thing open.

Jason Feifer:

And now I have access to all these incredibly successful people. Ronald Reynolds, who I interviewed once, told me this great thing, which he said that to be good at something, you have to be willing to be bad, which is to say that the thing that drives success isn't starting something and being good at it. That should be nobody's expectation. That's not true. Instead, the thing that separates successful people from not successful people is that the successful people are willing to tolerate being bad for long enough to get to good, and not everyone is willing to do that, and the reason I think I was able to do that was because I just I had an inherent confidence that I could figure this out, and what I needed were little crumbs to follow, and you just start from there In that time. So you must've pitched I don't know how many editors, but now you are an editor.

Anne McGinty:

So you have this very unique perspective of being the person At that time. So you must have pitched I don't know how many editors, who knows but now you are an editor. So, you have this very unique perspective of being the person pitching and now receiving the pitches. What have you learned in that process?

Jason Feifer:

Yes, I've learned. When I was pitching editors, I thought that I was up against the best of the best of the best, and now, on the other side of that, I realize that most competition is bad. It's true, most competition is bad. Most of the people that you are competing against in any competition in the world are not good at it. I mean, look, if you're in the NBA, then obviously everyone you're competing against is an amazing basketball player. But that's not the way that most things work. If you're sending an editor an email with an idea, you're up against a lot of noise, right? That editor has a lot of noise in front of them. The inbox is very full. People are constantly grabbing their attention. These days, the editor also has almost no resources compared to what it was like two decades ago.

Jason Feifer:

And, by the way, my answer here is not really just specifically about media. I'm kind of using media as an example, but I really do believe this largely applies all over the place. And yet who you're actually competing against is mostly not quality. It's mostly noise. In my case, it would be a lot of people who are lazy writers, who are bad on deadline, who haven't done a lot of work on their pitches. That's what I'm seeing. Most pitches that show up in my inbox from writers or from publicists, or for what are bad. They haven't put any work into understanding the person who they're reaching out to. And the reason I tell you that is because I think that people often overlook small competitive advantages that are actually true, great competitive advantages. Trust is a competitive advantage, hustle is a competitive advantage, responsiveness is a competitive advantage. Iustle is a competitive advantage. Responsiveness is a competitive advantage.

Jason Feifer:

I think about this all the time now, literally. Last night at 8.30 pm I was on a group call with a trade association that is planning out an annual meeting and I'm the keynote speaker, and they had also asked if I could help them think through some of the things for the event and maybe bring in a couple other speakers. And I said, sure, no problem, I've already taken two calls with them. And at the end of the last call, one of the women on the call said you know, jason, I just want to tell you we have never had a speaker join these planning calls before and it has made it so much easier to plan this event.

Jason Feifer:

And I know that most people don't do this. Most people don't even give clients access to them. They have some intermediary. I think that's ridiculous. My competitive advantage is my ability to be easily reached and to engage and to be responsive, and that's why I will get business that other people won't. The way I think about it is I'm competing against a lot of noise, but I'm not competing against a lot of quality. It's true, that's not to say there aren't quality people out there. There are. There are amazing quality people out there, but there's a lot of noise and everyone should be mindful of that.

Anne McGinty:

I know what you're talking about because I also receive pitches every day and some of them are truly connecting and then others are just very cold. So I noticed on your LinkedIn page that you talk about a wouldn't go back moment. Can you talk to us a little bit about what that means to you and why it's so important for you to help people find this Sure?

Jason Feifer:

So the wouldn't go back moment comes from this framework that was central to the book I wrote called Build for Tomorrow an action plan for embracing change, adapting fast and future-proofing your career tomorrow. An action plan for embracing change, adapting fast and future-proofing your career, and the central idea there is that change happens in four phases. So the first phase is panic, then adaptation, then you find a new normal, some new comforts and familiarities, and then you get to wouldn't go back, that moment where you have something so new and valuable that you wouldn't want to go back to a time before you had it. My argument is that that process, it will happen to you, regardless of your station in life or your amount of experience. The question for you is how fast do you want to move through it? Do you want to stay in panic for a really long time? Or, if you know that wouldn't go back as available to you, do you want to start moving towards that faster and taking steps that push you into the adaptation and the new normal To bring that to life.

Jason Feifer:

Lena's Wigs was a wig shop in Baltimore, just a regular old storefront. You walk in, you shop for wigs and then COVID and she can't operate her storefront the way that she used to. Everything is locked down. She's trying to figure out what to do, and the only idea that she can come up with is not some revolutionary, crazy idea. It was something she was well aware of but had never taken seriously because she thought it would be bad for her business. And that was appointment only. You make an appointment and then you get personalized attention for wig shopping and she thought this is not a good idea. Nobody wants friction, Nobody wants to make an appointment and wait. You want the wig. You go to the wig store, you walk into the wig store. That's why it's there. But this is now the only way that she can do it, and so this is what she does, and two things happen that shock her. The first is that sales go up. The second is that customers are happier. So here we are.

Jason Feifer:

She used to operate the storefront, Now it's appointment only. There's more friction involved. It would seem to be more inconvenient for people and they're happier and they're spending more money. Why is that? Well, what she discovered was that you know who does not buy wigs? The answer is people who walk in off the street. They don't buy wigs, they browse wigs. They're kind of curious about wigs. They don't buy wigs. You know who buys wigs? People who are shopping for very personal reasons, usually health or religious reasons. They would far, far far prefer to do that shopping in a way in which they are not surrounded by a bunch of randos who have walked in off the street.

Jason Feifer:

And so here Lena had been operating this company the way that she thought she had to operate it. She was paying a person to greet the people who were coming in off the street and not buying wigs, at the expense of an experience that would be better for the people who actually do buy wigs. And once she discovered this, she realized oh my God, there's a whole different way to do this business. She told me this story during COVID and we stayed in touch. She now has leaned very heavily into her digital presence. She's doing digital fittings. She's able to sell to people far outside of Baltimore. Now she makes far more money than she did before. She has a much better operating business than she did before. That is a wouldn't go back moment. Lena would never, ever go back to the way that her company used to run, but she had to get shoved into this new idea. She wasn't ever going to do it herself. But change came to her. She panicked, she adapted, she found a new normal. She wouldn't go back.

Anne McGinty:

That's amazing. Yeah, sometimes you just have to try something, at least be willing to. Yeah, when you had mentioned panic, I was wondering okay, so he's an editor, he's a speaker. There must be a moment in your life where you've just faced an incredibly challenging or heart rate increasing situation and I was wondering if you can tell us about one of those and how you handled getting out of the panic.

Jason Feifer:

Yeah, oh well, I mean, they still happen all the time, but I'll tell you the most recent one, because it's fresh on my mind, which is I have a pretty busy travel schedule where I will travel to industry conferences or corporate events and I keynote, usually, the opening of it. And I've been doing this for years. I'm very comfortable with it. I've done all sorts of audiences. That context is important to understand the thing that happened this summer, 2024, where I flew out to Las Vegas to speak at a conference for real estate appraisers out to Las Vegas to speak at a conference for real estate appraisers and they booked me for a 30 minute talk and I was standing at the side of the stage. I'm about to go on and this guy comes up to me and he says hey, I'll be your timekeeper because they didn't have a clock on the stage, which people usually do. But they didn't. So he said I'll just be in the front row and I'll just hold up a sign when there's 10 minutes left. And when there's five minutes left, I said sure, no problem, I've done this so many times. I know exactly where I am in the talk. I know how long it's going to take. I don't really need this. But sure, I get on stage and it's going great, it's full of energy, the audience is into it.

Jason Feifer:

I'm almost halfway through my first section. My talk has an intro and then the kind of multiple sections, depending on how long the talk. So I'm in the first section and the guy holds up a 10, and I see it and I don't understand it, because my first thought was maybe it means that I've been on stage for 10 minutes. But that's not even true, because I should have been on stage for like maybe 12 minutes, 13. Like, that's not the 10 minute mark. I don't know what that means. I'm just going to keep going. So I kind of wrap up the first section of the talk and I start to enter the second section of the talk and then he holds up a five, and now I don't know what's happening.

Jason Feifer:

Now I'm completely lost, right, and what I start to think is this is a 30 minute talk. He's telling me that it's five minutes is left. I can see he's got a timer. Have I been on stage for 25 minutes? Like, have I been rambling incoherently on stage for 20? Like, have I? Has something gone very wrong here, you know? And that was like unlikely but plausible, because I had a poor night's sleep the night before I had gotten up early, I had flown from New York to Las Vegas and then I'd gotten on stage in the afternoon, like it was a long day. It was a travel day. Maybe I am rambling incoherently here, like maybe something is very bad right now and the whole audience is just tolerating it. I couldn't figure it out.

Jason Feifer:

And as I'm trying to think through this, I'm also trying to continue my talk, but it's becoming harder and harder to do that now because I'm also trying to think about this and so I start stumbling on the talk. And now I have like a third thing to think about, which is that I'm stumbling on the talk and I don't know I got to get back. It became this spiral and I derailed. It's never happened to me before, but I just fully derailed and I couldn't get back into the talk. I couldn't find my place. The audience is now trying to help me saying the last things that I said. It was awful.

Jason Feifer:

Time is, at this point, very flexible. I don't know how long this was, but I was struggling to try to get back on track with the story that I've told a million times. And I realized at this point everyone's just hoping I get through this, which means that the story at this point that I'm telling is pointless. So instinct kicks in and I just I take my clicker that I had for my slides and I just toss it to the side and I just say, you know what, screw it. And everyone laughs and claps and the tension is broken.

Jason Feifer:

And then I kind of explain what I'm going through. I mean, I still can't figure out the timing issue. Like I don't know what's going on there and I don't want to like throw the timer under the bus Like I just don't know what's happening. So I just say this is really scary. I've seen this happen to other speakers, it's never happened to me before, and now it is, and it's really embarrassing.

Jason Feifer:

And like I'm the guy in charge here, I just sort of go, I'm like trying to explain what I'm going through and trying to turn it into like a lesson. And then I thank everybody for their patience and I get off stage and the first thing that happens is that the timekeeper runs up to me and explains what happened. And what happened was that his instructions were to keep me on track for a talk that went from 4.30 to5 because they needed to clear out of the room at 5. But the previous session had run long and then the sound guys had to do something and I didn't get on stage till like 4.43. And he didn't know what to do and so he just made an executive decision, which was to just time me to end at five, regardless of when I started, and nobody told me that. So that was the problem.

Jason Feifer:

But the next thing that happens is a ton of people rush up to me and they are happy. They are telling me that that was the most real thing that they have seen all day, and how encouraging it was to see someone in my position not be perfect, and that makes them feel better. And they were telling me about their own times where they have, like, frozen up. And I hear a lot of this and it makes me feel like better. The sponsor there was a sponsor who'd paid for me to come out there. The sponsor was happy, everyone was happy.

Jason Feifer:

And then I got stuck in this mode of thinking where I was like I went back to my room that night and I couldn't stop imagining other things that I could have done to have made that moment better. What could I have said? How could I have made it more memorable? And I came up with these ideas. I'm like, oh, if I had only thought to do that and I couldn't get it out of my head. I couldn't fall asleep.

Jason Feifer:

So, the 2 am, eastern Standard Time, which is where I live and where my friends are and I sent a voice memo to a friend of mine named Catherine Morgan Schaffler, who's a psychotherapist. I thought she would have something useful to tell me and I recapped everything that happened and I told her my new idea for how I could have done better. Then I was able to go to bed and when I woke up in the morning, I had a voice memo from her and I had this great advice, and so I'm just going to read it to you because it's so useful. These are her words. From now on, she says you're looking for a perfect version of this, but your perfect version is much less powerful than what ended up happening.

Jason Feifer:

Your version of perfect is a version where you don't trust the audience to figure out what everyone in that room knew and now gets to remember, which is that we all get scrambled and we all have a choice to make about how we recover, and the speed and efficiency with which we recover is not the thing that matters. What matters is that people see us trying, people see us making mistakes and people see us making reparative measures. The reparative measure is what matters, not whether the reparative measure is immediately efficient. So that was what Catherine said. In other words, don't measure yourself by how quickly or impressively you recover. Instead, measure yourself by your effort and your intentions, because that's what's controllable and that's what people will recognize. And that was an incredible lesson.

Anne McGinty:

Wow, and what an experience to face that level of vulnerability, especially unexpectedly like that in front of a crowd. Oh, my goodness, good for you, thanks, thanks. You said you were reflecting back on it and it didn't feel ideal, but really it was. Yeah, you were human, it was.

Jason Feifer:

You know, what my wife said to me when I told her the story when I got home was she was like you know, you went out there to deliver a memorable and important message to people and you didn't deliver the message that you intended to deliver, but you did deliver an important and memorable message and she was right. It's very true.

Anne McGinty:

That's totally right. So I want to shift a little bit now into a little bit more of your role as the editor of Entrepreneur Magazine. Can you talk to us a little bit about? Into a little bit more of your role as the editor of Entrepreneur Magazine. Can you talk to us a little?

Jason Feifer:

bit about what some of the most memorable interviews have been and why. Oh yeah, the way that my brain works is that I absorb lessons and anecdotes, and the things that matter most to me are the ones that I can repeat to others, and the things that become the most meaningful are usually some interaction or some insight that happened and almost in the moment. I know I will be repeating this for a very long time, or sometimes it happens afterwards. So here's like one example I went to 30 Rockefeller Plaza and went up to Jimmy Fallon's office and had a wonderful conversation with him for maybe like an hour and a half and he's great, really thoughtful, really fun, really enjoyed him. And at the end of the interview Jimmy says to me hey, if you are writing this story and you realize like I wish I had asked Jimmy this question, I didn't think to just reach out. It's totally fine. And I said to Jimmy I really appreciate that I am not going to do that because I've already taken up a lot of your time and you're a busy guy and I just I've got what I need, but that's really nice of you. And then I go home and I'm writing the story and wouldn't you know it. I realized, oh my God, if I could ask Jimmy this one thing, it would make this story so much better.

Jason Feifer:

And I never follow up on these because I don't want to be an imposition. I hate being an imposition and people are busy. But I just can't find another way to land this story without asking him this question. And so I say, well, he did say I could do it. So I reached out to his publicist. I said, hey, could I just get five more minutes with Jimmy? And he says let me see what I can do.

Jason Feifer:

And then, like a week later, I got a call from Jimmy Fallon and Jimmy says to me when we start, he says you know, it's so funny. I always tell people if you ever have any follow up, just reach out. And nobody ever does. And you're the, you're the first person to do it. And I said, well, that's really funny, jimmy, because I I told you I wasn't going to do this and I didn't want to because I didn't want to be an imposition, like I didn't want to take more of your time, actually feel really bad that I've done this. And he said, no, are you kidding? You asking for more time tells me that you are a really thorough person and that you want to get things right, and that makes me more excited to talk to you.

Jason Feifer:

And that moment has crystallized in my mind because what it was a great representation of was how we make these assumptions about what is good and what is bad, and we are not always right about that. I hate asking people for favors because I don't want to put them out, but what I've learned when I have had to ask people for favors is that they really like it. It's a good bonding experience. Usually I've done something for them and I never asked for something in return and they are excited to do that and it creates more bonds. So we walk around with all these ideas about what we shouldn't be doing and what's bad and we really need to challenge those and that's why I really loved that moment with Jimmy. It never even made it into the story, but it was my favorite moment from that interview.

Anne McGinty:

Yeah, to just not make assumptions. I just want to ask you one final question, which is if you could go back and talk with yourself when you were in your early 20s, what life wisdom would you give yourself?

Jason Feifer:

I had these ideas about specific things that I wanted to do and the path that was going to be required to get there, and what I've learned is that the zigzag pathway, where it just seems to make no sense as it's happening, but when you zoom out it is logical. I did this and because of that I met this person and then went in this direction, and then doing that taught me this thing, which sent me over there. That is actually what the pathway looks like. It is somewhat uncontrollable. The most valuable thing that you can do is be open to opportunities that don't fit your original thesis of what opportunity is, but that might turn out to be the most valuable thing that you ever did. I had absolutely no intention of ever being at Entrepreneur Magazine. I couldn't have even told you Entrepreneur Magazine existed in the world when I first started my career, and it turns out to have been the thing that completely shaped this next phase of my career. So just be open to where the opportunities are, rather than limiting yourself to where you think they are.

Anne McGinty:

Well, Jason, thank you so much for coming on the show and sharing your time with me. I know you're busy, so I really appreciate it.

Jason Feifer:

Oh yeah, it was my pleasure. Thanks for having me. If anyone wants to catch my work anywhere, my newsletter is the best place to start. It's called One Thing Better Each week, one way to build a career or company you love and be more successful and satisfied doing it. You can find that by going to onethingbetteremail. That's a web address, so plug it into a browser, onethingbetteremail. Thanks so much again. Thank you, I'll see you later.

Anne McGinty:

Thanks so much again. Thank you, I'll see you later. Today's key takeaways Stay humble and keep learning. Every moment is a learning opportunity. Don't wait for success to come to you. Go after it and put yourself in front of the right people To move up. Position yourself at the level of those you want to impress. Expect rejection it's part of the process, but every no is a step toward a yes. As Jason says, rejection is like a puzzle. When you're rejected, look for a new way to slot in. Every rejection holds a lesson, and that's an opportunity to build resilience, adapt and improve. Think outside the traditional route. Sometimes the alternate path is faster and more rewarding.

Anne McGinty:

Growth happens when you explore what's available by pushing yourself to try new things. Often, getting your foot in the door with one key person is all it takes to get the ball rolling. From there you'll find clues to follow, but first you need to figure out how to open the initial door. As Jason mentioned, ryan Reynolds said To be good at something, you have to be willing to be bad. The difference between success and failure is the willingness to endure being bad long enough to get good.

Anne McGinty:

When pitching, know that most competition isn't great, but you're still up against a lot of noise. Do the work, understand who you're reaching out to and find small competitive advantages. I really want to emphasize this because I see it firsthand in my inbox. The majority of pitches I receive miss the mark. Trust hustle and responsiveness are competitive advantages. Advantages being responsive and easy to engage with will set you apart. Change can be scary, but the faster you adapt, the quicker you'll get to your new normal. It's okay to feel the panic. What matters is how you push through. You, me, all of us are human. Don't measure your worth by how quickly or impressively you recover from mistakes. Instead, focus on your effort and intentions and celebrate being human, which means embracing imperfection. And, lastly, challenge your assumptions. What you think is good or bad may not always be true. Be open to opportunities that don't fit your original expectations. Sometimes the best opportunities are the ones you didn't plan for. That's it for today. I release episodes once a week, so come back and check it out. Have a great day.

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