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

So just be open to where the opportunities are , rather than limiting yourself to where you think they are .

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 .

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 .

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 .

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 .

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 .

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 .

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 .

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 . 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 .

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 . 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 . 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 . 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 .

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 .

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 . 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 .

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 .

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 .

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 . 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 . 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 .

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 . 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 . 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 .

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 . 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 . 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 .

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 .

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 .

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 .

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 . 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 .

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 .

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 .

That's a web address , so plug it into a browser , onethingbetteremail . Thanks so much again . Thank you , I'll see you later .

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 . 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 .

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 .