How to get 240k followers on LinkedIn: the Jason Feifer story
December 30, 2025
Intro
The LinkedIn algorithm doesn’t ignore your external links: it ignores lazy content. 240,000+ followers and 10 years as Editor-in-Chief. Jason Feifer is the EIC of Entrepreneur Magazine, but he didn't get there by just doing what he was told. After realizing that "Opportunity Set A" (doing your job) only leads to slow growth, Jason mastered "Opportunity Set B," the art of hunting down opportunities nobody asked you to do. In this conversation, Jason shares insider insights from his conversations with LinkedIn’s leadership (including Dan Roth) about how the algorithm actually works. He debunks the "link in comments" myth, explains why you need to be willing to be bad to get good, and breaks down his formula for content: the perfect mix of "Predictability and Surprise." We discuss how to escape the "Moat of Low Status," why he treats his LinkedIn profile like a media company, and his specific wish list for future platform features. If you want to build authority without waiting for permission or understand the mechanics of high-performing content, this episode is for you. Connect with Jason: https://www.linkedin.com/in/jasonfeifer/ Subscribe to Jason’s newsletter: https://www.jasonfeifer.com/newsletter/ Go to connectionaccepted.com and put in your email if you want to be in a future creator help hotline episode. For sponsorships or business inquiries reach out to connectionaccepted@gmail.com Join Matt & I as we build a $10M Podcast: Subscribe on YouTube Listen on Spotify: https://open.spotify.com/show/3oeHvC5O1oSqIw428DpTHXsi=wy5JJTUvQ96a01xoRqeHG Listen on Apple: https://podcasts.apple.com/us/podcast/connection-accepted/id1844434065 Our LinkedIn: https://www.linkedin.com/company/connection-accepted/
Transcription
Daniel: Jason Pfeiffer is a LinkedIn top voice with over 243,000 followers. He's also the editor in chief of Entrepreneur Magazine, which is one of the definitive voices in the space. In this episode, we dive into not just Jason's unique background, ascending to the ranks of editor in chief and building an audience of over 200,000. But we also talk about Jason's unique perspective having posted on LinkedIn for years on what the LinkedIn algorithm is actually optimizing for. No spoilers, but it's not virality. It's an episode that you won't want to miss. Let's get right into it. Welcome to Connection Accepted. Today, we've got Jason Pfeiffer on the pod. Matt: Jason, thanks for joining me. Daniel: Thanks for having me. Matt: Awesome. So Jason, just to kick things off for people who have no idea who you are, first time meeting you, can you just give a quick background on who you are, where you're from, and what you're currently working on? Daniel: Sure. So, hey, everybody. I am the editor-in-chief of Entrepreneur Magazine, and I have been so for the past 10 years, which is an insane thing to say. And so that is often the way that people know me, though, appropriate for our conversation today, when I meet people, frequently the first thing that they say is not, oh, my God, I loved the article you wrote in the magazine. Rather, what they say is, I love your posts on LinkedIn. LinkedIn just has a kind of scale and in-your-faceness that keeps people so top of mind, and that's why I find it so powerful. So I'm excited to talk about that. But what else do I do? I make a lot of media myself, a newsletter, podcasts, wrote a book. I travel and do a lot of corporate keynote speaking. I sit on a lot of advisory boards. I help a number of other businesses in various capacities. I oversee content, communications, strategy. And generally, my thing is that I love building and I love helping people build. I love entrepreneurs. And so I'm just out there trying to make life better for everybody. Matt: That's awesome. You are clearly a man of many talents, Jason. Let's focus on Entrepreneur Magazine first, though. Daniel: Sure. Matt: How did you find your way over to eventually being editor-in-chief over there? Let's start from the early days. Daniel: Yeah, so the really, well, I mean, how far do you want to go back? So Matt, you and I were talking just before we started recording that we both have roots in Worcester, Massachusetts. Worcester, Massachusetts is a kind of post-industrial city in the center of Mass. And I went to college there, and then I graduated, and my first job out of college was at a place called the Gardner News. Gardner News was, at the time, and this is like 2002, 6,000 circulation. I'm sure it's not even that anymore. A daily newspaper, I'm sure it's not that anymore, in North Central Massachusetts. And anyway, the reason that I tell you that was because I sat there as this tiny small-town newspaper reporter, and I just dreamed of big things. I dreamed of writing for giant publications. Daniel: I dreamed of being really relevant to a broad audience. And I had no idea how to get there, but I just expected that people would notice my talent. And I was waiting for the phone call, and the phone call never came. And after about a year, I was just getting really bitter at the Gardner News. And that is when I came upon the single most powerful realization of my career, and it really explains how I got to Entrepreneur Magazine, which is that I realized nobody is going to reach out to me. I have to get in front of people. I have to be the one to constantly hunt down opportunity myself. And I didn't have language for this back then, but I do now. So I will tell you that what I now think of this as is this. In front of you, Matt, and everybody listening right now, there are two sets of opportunities, opportunity set A, opportunity set B. Opportunity set A is everything that's asked of you. So if you have a job and you go to that job and your boss or whoever has expectations of you, there are measurements by which you are going to be measured up against. Then you have to do a good job and that's opportunity set A. But then there's also opportunity set B. And opportunity set B is everything that's available to you that nobody is asking you to do. And that could be you like listening to podcasts and you start a podcast. That could be you take a class in something. That could be you volunteer to join a different team. Whatever the case is, it's the thing that's available. Lots of things are available to you, but then nobody's asking you to do. And my argument is, and this is from lived experience, that opportunity set B, the thing that is available to you that nobody is asking you to do is always more powerful. Opportunity set A, do the thing that's asked of you. That's fine. That's good. If that's all you do, you will only be qualified to do the thing you're already doing. Opportunity set B is where growth happens. What did I do? I quit that job. I quit that job and I sat in my bedroom for nine months and I cold pitched editors because I realized nobody's going to hire me at the New York Times or the Washington Post, but they might read an email of mine. And maybe I can convince them to do one story with me, just one story. And if I can do one, then maybe I can do two. And if I could do two, I can do more and I can start to build a career. And that's exactly what I did. I started to write for these publications and that led to different jobs and eventually moving to New York and starting to work for magazines. And I just kept doing that. So at every magazine, even when I was working for national magazines, I would think, what else can I do? What else is available to me? For a while, it was just writing for other magazines. Then it was teaching writing and then it was making viral websites. And then it was doing some consulting. Daniel: And now at entrepreneur, you know, look, I'm an employee of entrepreneur magazine, but I have built a business for myself, multiple of them that bring in, frankly, far more revenue than entrepreneur magazine pays me. And it's all, nobody asked me to give a keynote talk. I decided I was going to give a keynote talk and then I hunted down people until they put me on a stage. Doing that over and over again is ultimately what got me to rise up in my career enough that somebody was willing to hand entrepreneur magazine, the editorial reins over to me and why I continue to grow in the way I do. Matt: Wow, that Jason, that you articulated that so well. And you know, the difference between, you know, opportunities A versus opportunity B, right? Going after the things that are available to you versus just the things that are being told to you. A couple of questions. First, though, why do you think it's so much more powerful for people to go after the things that are available to them, not just the things that people are asking them to do? Daniel: Well, I mean, very simply because there are more opportunities that are available to you than there are opportunities that people are asking you to do. I mean, look, when you work for somebody else, they have an incentive to keep you focused on the thing that is most convenient for them. So if you're working at a job, you know, your boss hopefully wants what's best for you in terms of rising and succeeding and all of that. But what is most convenient for the boss is for you to do a thing really well and then to keep doing it and to be reliable. Because if you're reliable and the thing that you're doing, then they don't have to worry about that and they can shift their worry to something else, which means that they don't really have an incentive to advance you. Now they will, hopefully. That's what good company culture is. But it's not going to happen at the speed in which you like and it's likely going to happen within the confines of what is convenient for the management of the company. So you need to be aware of that and you need to know that the greatest opportunities that are going to be handed to you are likely not going to be coming from a linear path inside of an organization. They're going to be coming from other things that you can do inside of that organization or outside to take the reins yourself. And I there was a moment in my career. This was, I'm not sure that I've ever actually shared this particular thing. I was, I worked at Men's Health. That was my first national magazine job. I moved to New York. I was 28. I worked for Men's Health. I was there for two or three years. And then I got an offer at another magazine. And the top two people, the editor-in-chief and his like side person at the time, they called me into the office. These are intimidating guys, you know, like I'm a junior guy. These are big deal people. Daniel: And they said to me, what are you doing? What are you doing? Why are you leaving? They're not going to be able, what are you going to go to that other magazine? What are they going to do for you? And they were kind of trying to badger me into staying. And I thought about it for a second because I was like, oh, I'm valued. They really want me to stay here. But you know what? No, what they wanted was to not replace me. That's what they wanted. They wanted to not have to go through the rigmarole of replacing me because it's a pain to replace somebody. And so it was easier for them if I stayed where I Matt: Much uncertainty and risk. I'm curious for you, because a lot of entrepreneurs probably also go through similar thought processes. It's a risky path, right? Compared to staying at a stable corporate job. How do you think about risk in general, in your career, in life? Daniel: It's a personal question, and it's not for everybody. I mean, look, when I'm saying to do these kinds of things, I also know that they are going to land differently with everybody. Everybody's got different financial situations. Everybody's got different responsibilities. Some people are single and can do whatever they want with themselves and their finances, and other people have families that are relying on them for an income. So in all cases, risk tolerance is going to be different. But I think also, in all cases, that we do a service for ourselves by not handing full control over to somebody else. So if you are in a job and you are thinking about doing something else, well, what can you do right now, if you can't walk away from that income, what can you do right now to start to build, to explore, to maybe figure out what else you're good at? Or, you know, I've got an idea for a product or a service. Can I test it out in a little bit of ways? Can I kind of figure out who my first customers would be? Can I get some feedback for them? What can I do that gives me more leverage without sacrificing the thing that I already have? I never, ever, ever push people to do things that they're not comfortable with. And frankly, you know, look, I run Entrepreneur Magazine. I don't think everyone should be an entrepreneur, not at all. Most people are not cut out for it. It is very, very hard. And if that's not your path, that's not your path. That's fine. You can be an intrapreneur. You can build other things for yourself. You can do whatever it is that you want. But I think that we ultimately have to recognize that if we give full control of our future to somebody else, and we are not doing anything to build upon our own ownable assets, our own future, then we put ourselves in a position of severe risk for disruption. Matt: Jason, I love the way that you described it. Entrepreneurship, it's not for everyone. Daniel: For you, was there a specific moment, or maybe it wasn't one moment, but maybe a series of moments even, or a period of your life where you realized this is the path that I want to go down? Like, I want to take a more entrepreneurial approach to my career. Matt: Yeah. I mean, you know, I've been doing it for a long time in many different ways, as I described to you. I mean, even when I was working at Men's Health, and they actually wouldn't allow their staff to freelance for other magazines. So you know what I did? I did it anyway. And I hoped that they didn't notice. And sometimes I wrote under fake names. And then I also started teaching writing, which I hadn't done before. But I was like, you can't stop me from teaching writing. So I was always pushing myself out. Um, but, you know, it's funny. I kind of blanked on the question that you asked me because I went in there. What did you ask me? Daniel: Yeah. Was there a moment or a series of moments? Matt: Oh, yeah, there was a moment. Right. Was there a moment? So the moment was this. The moment was when I got to Entrepreneur Magazine. And at first, I thought of it as a media job. I mean, it is a media job. But I thought of it as a media job where I realized, okay, my first task here is to be good at this, is to assess what needs doing here. What does this brand need? How can I add value? How can I recognize what it's doing well and what it could be doing better? And then what kind of changes do we need to make in order to start to fulfill that? And after about a year of that, I started to say yes to interviews that I was getting requests for. People would want me on their podcast. They'd want me on their show or something. They'd want me on a stage. I wasn't really comfortable doing that at first because I wasn't an entrepreneur. I was a media guy. I just kind of stumbled into this. And so I started to say yes to those opportunities. And it was very interesting because people were treating me like an authority. They were treating me like a guy who knows a lot of secrets, of wisdom, of insights, of guidance for entrepreneurs. And I didn't feel that. And it was scary. But I also realized that there was a massive opportunity here right now. And that massive opportunity was to grow into the person that people think I am. And if I could do that, if I could understand what it is that they're looking to me for and how to fulfill that in a way that felt distinct and comfortable for me, then opportunities were endless. Right. Then I transformed myself. Then I don't just become a media guy. I become an asset. I become a kind of ownable platform. Daniel: And so I, you know, I had to think really long and hard about what, what am I and what does it mean to, to do that? And, um, and what uncomfortable places do I have to go into and how do I fill my head with a body of knowledge and work that I don't have right now? It took years to do this, to turn myself into the kind of person that is comfortable going on your show and having this kind of conversation and drawing upon these kinds of insights. I didn't have that stuff back then, but I realized again, the opportunity was there and I don't think that there's anything more powerful than recognizing that if you are willing to go through the gauntlet, that on the other side of it is tremendous growth. Ryan Reynolds once told me, and I get to name drop this kind of stuff because I get to talk to these kinds of people. Ryan Reynolds once told me, um, to be good at something, you must be willing to be bad. To be good at something, you must be willing to be bad, which is true. We are not good at new things at the beginning. The thing that separates successful people from unsuccessful people is not whether you're good at something at the start, but rather whether you are willing to tolerate being bad long enough to get to good. And that was honestly the thing that I discovered. And it took me a long, long time to get there. Matt: I love that. The thing you said around, you know, having to be okay with being bad at the beginning is actually what separates the people that, you know, in a year or two years, five years from now, you're like, wow, they're, they're so successful at their business or whatever other pursuit it is. And people only see that success when, you know, they've succeeded in most cases. But, uh, we, we tend to forget the fact that every expert, every professional athlete, every actor, every successful business person at one point started out as a beginner. There's another analogy that I think captures it really well, which is the, the moat of low status. It's like, you have to go through this period in the beginning where you might look stupid doing something. You might have people talking behind your back. Uh, but if you stick with it and you continue to improve every day, then eventually you'll, you'll come out of that moat of low status. And I don't know how long it takes. It's dependent on the person and what you're doing. But I think what you said there absolutely hits the nail on the head. Daniel: Yeah. And I don't actually think that a lot of people are going to be talking behind your back. I really don't because expectations are lower than you think that they are. We have high expectations for ourselves and we're measuring ourselves up against something that is unachievable to start. Ira Glass from This American Life has a really nice way of saying it, where he says that at the very beginning of doing something new, there is a large gap between your tastes and your abilities. You know what good looks like. Daniel: You have good taste, but you don't have the abilities to produce the things that you think are good. And that is the thing that ultimately dissuades many people from pursuing a new path because they just can't tolerate that dissatisfaction, that being unable to meet what they see as great. I mean, look, if people are watching this, they may see these these bass guitars behind me. I am not that good at the bass guitar. I like like that is a that is a misrepresentation of me that I've got those back there. They're back there because I played bass in high school and then I took a long break from it and I want to get back into it as a way to just relax and turn my brain off a little bit. And I realized that I will never pick these things up if they're in a case. They need to be on the wall right behind me so that I will grab them. But look, I picked those things up and I cannot come anywhere near producing the sound of music that I like to listen to. I love Green Day. Mike Dern is one of the greatest bassists. Like I can't play like him. He's really good. And so I play and I'm like, that doesn't sound like Mike. But you know what? That doesn't really matter because the point of this is to just grow and nobody expects me to be like Mike. And maybe one day I'll just become like me instead. I'll just sound like me. But the point is, people aren't comparing you against whatever you're comparing yourself to. People are taking you on face value. So grow, do not be self-conscious. Do not worry about what other people are seeing. And then one day you look, your B minus, the thing life and career where I really was just a writer or a magazine editor, you know, at Men's Health or at Fast Company or whatever. Writers who get published in magazines, they want people to read their stuff. And so I was just using social media, whether it was Twitter or LinkedIn or whatever, just purely as a means of posting links to my stories and hoping that people would read them. That was it. And people didn't. Those posts never got any engagement on LinkedIn, and it drove me crazy. And it made me think, ah, LinkedIn is garbage. And it wasn't until many years later, as I told you, realized that if I could live up to the expectations people had of me, that there was probably an amazing opportunity available. I realized those people are on LinkedIn, and I started to look at what was happening on LinkedIn. And I realized that posts that drive people to a link perform poorly, not for the reason people realize, or not a rather, let me say that again, not for the reason people think, though, and we should unpack that because there's a misconception that LinkedIn depresses the reach of posts that have links in them, and that's not actually true. So let me dispel that for you in a second. But I realized that instead, what was really happening was that people were sharing insights. They were sharing their knowledge. They were sharing advice. And so I started to lean into that. Daniel: And that is when I saw my relationship with that audience transform, where now people were starting to engage with posts. And now they were starting to see me as an authority. And it took a long time to figure out how to actually do that well and start to really gain the kind of traction that I now have. But I knew I was on to something the very beginning of my journey at Entrepreneur when I started to shift away from using LinkedIn as a promotional tool and started to use it as an advice-giving tool. Matt: Jason, this is perfect. And I want to dig into the distinction between advice versus promotion. Before we do get into that, let's talk a little bit about what you were saying about links, though. There's this common misconception that having a link to an external website in your post depresses your reach. Right. Which is the reason why people always do link in comments. Okay. What are your thoughts on that? Daniel: It's a total misunderstanding. It's a total misunderstanding of what drives visibility on LinkedIn. So let's break it down. And now, look, this is not my own hypothesizing. This is what I have gotten from multiple senior-level conversations with people at LinkedIn. Because of my role as editor-in-chief of Entrepreneur Magazine, I get to meet lots of people at LinkedIn, and I have really good relationships. I know Dan Roth, the editor-in-chief. I know their head of comms. I know their CMO. I'm talking to these people, and I'm getting insights into how this stuff actually works. I've been on calls with their head of product, the people who are building the algorithm. So here is what they all tell me. They tell me that what LinkedIn's algorithm is looking for are the following things. It wants posts that are full of knowledge and advice. It wants posts where the knowledge and advice is being drawn from your professional experience, which is to say that if I go on to LinkedIn and I write a post about communications, well, the LinkedIn algorithm, LinkedIn itself, is looking at my background and my past post history and saying, Yeah, that guy's an expert in communications. Therefore, what he's writing here is more trustworthy. But if I start writing about biohacking, I don't know anything about biohacking, not at all. I am not a trusted authority on biohacking, and LinkedIn will recognize that and it will depress the reach of those posts because it won't be as trustworthy. So, okay, so we're looking for knowledge and advice from your base of authority. And then the next part is really critical to understanding this thing, which is meaningful comments. It is looking for meaningful engagement from the target audience for an individual post. So Dan Roth, the editor-in-chief of LinkedIn, told me that he thinks of every single user's post as having a total addressable market. And the goal of the LinkedIn algorithm is to try to help those people, like every person who's posting on LinkedIn, reach their total addressable market. Daniel: Now, people like me, you know, our total addressable market is intended to be much larger, right? I want to reach the masses. I want millions of people to see every post of mine. But that's a fringe use case. Most people on LinkedIn are just posting about their own industry, and they're just trying to drive economic opportunity inside of their own industry. So you might have somebody, for example, in hospital administration who's posting about hospital administration and is hoping to get noticed by, I don't know, let's just say an administrator at a larger hospital, right? Like that is what they're looking for. So they want to identify what is this post about, who's the authority that it is being drawn from, and then who is that total addressable market? And then once it reaches part of that market, so if I'm in hospital administration, I post something about hospital administration, it reaches other people in hospital administration. Are those people meaningfully engaging with the posts? Are they leaving thoughtful comments, which the algorithm is taking to mean that this is indeed a good match for that audience and it's driving meaningful conversation? So this is in contrast to when people do engagement groups, you know, which is just like a group of people who are all engaged on the same stuff and their engagements are all like, yes, totally. Awesome. A bunch of emojis. Like the LinkedIn algorithm is actually trying to spot that as fake engagement and then not count it towards amplification for the post. So they're looking for that meaningful comments. Now, okay, the reason to understand all of that is to now apply that to what happens when you write a post that contains a link. When most people write a post that contains a link, the post kind of goes like this. It's like, we just launched our new line of crackers and they are so delicious. Click here to learn more. That's often the kind of thing that people are using when they're posting links on LinkedIn, right? Is that it's the post itself is not really offering value. The post is trying to drive people to click the link where the value is. But now think about what happens here. So number one, there isn't much to comment on, so people are not going to comment. Also, there's less information for the algorithm to know who the actual audience for this post is. And then very importantly, if someone is going to take an action on that post, the action that they're going to take is likely to be clicking the link, which is fine, but clicking the link isn't coming back and commenting on the post. And therefore the LinkedIn algorithm has no idea if anybody actually cares about this post, so it's not going to amplify it. There's another kind of post, which is, you know, the knowledge and advice post, which is totally driving that kind of commenting and that kind of engagement, and that's going to create lift. Matt: So how can you actually post things where there's a link and get engagement? The answer is that you have to do the hybrid of these two things. You have to write a post that contains knowledge and advice that feels like a fully complete post on its own. Like if it didn't have your call to action, if it didn't have your link, it was still a great post and people will still engage with it. And then at the end, you can create some kind of turn where there's a CTA and there's a link. This is what I do every day. There's always some kind of CTA at the bottom of my posts and it performs just fine because 90% of the thing that I have written is value. And only at the very end is there that 10% of CTA and the LinkedIn algorithm is not going to be digging me for that. Daniel: Jason, that was so well articulated. And I think this neatly leads me back to the discussion around value versus pure promotion. Right. And I'd love to get into that as well, because what I'm hearing is if your post still delivers a sufficient amount of value and the objective of that post is still to foster some sort of discussion with the audience that you're targeting so that people comment meaningful comments, then the link shouldn't tank the engagement or shouldn't tank the reach of that post. However, if the post is purely promotional and it's so obvious that, you know, you're just trying to get people to get click off to your landing page or click off to whatever promotion you're running and it's not fostering or incentivizing people to engage, then that is not going to get pushed out as much. Right. But I want to hear your thoughts on providing value versus promotion, because I think a lot of founders these days on LinkedIn, they're going there because, as you said, economic opportunity. They want to sell their product. They want to sell their service. They want to get more customers. So I see a lot and I run a ghost writing agency now, and I see a lot of founders that they want to just post every post being promotional. But it feels like in today's environment, and I'd love to hear your perspective here that you almost have to earn the right to promote. So being value first to me feels like the right approach there, but curious your thoughts. Matt: I completely agree. I mean, look, you have to start from the perspective of the audience. And to understand an audience, it's really helpful to just think of yourself and your own user behavior, because, you know, you are, in many ways, your consumer. And you are navigating the world as a consumer. And so if you watch your own consumer behavior, you can get to understand others' behavior as well. And I now ask you, do you follow anybody on any platform in which all they post is promotional stuff? I can't think of a single person that I do who does that. I do follow plenty of people who post promotional things, but the reason is because I have built some kind of parasocial relationship with them, where I follow them and I like their stuff. Daniel: I mean, let's just like, you can just continue to use like Mike Dirnt, the bassist from Green Day, for example. Like, you know, Mike, Mike posts mostly, like, you know, like videos from their concerts and some other kind of Green Day things. But then every once in a while, he's got something to sell. He just released a new signature bass, and it looks awesome. I think I'm going to buy it. But I'm down for that because what I'm really getting from him is I'm getting to feel closer to this band that I like, right? But if it was just promotional, I wouldn't follow him because that would be annoying. It's like I'm not there to shop Green Day. I'm there to experience Green Day. Matt: And the same is true for a smaller brand too. What you need to do is be relevant to your audience, and sales pitches are not relevant to your audience. So what I like to ask people when they're in this moment is, think about who your company serves and then the problem that your product or service solves for them. And now ask yourself, how can you solve that problem too through ideas and content? So, for example, if I am the founder of a kids snack brand, well, you know, look, a post about the kids snack brand every so often is totally fine, but the reason why people are going to follow me is because I'm going to be offering lots of guidance on healthy meals for kids or how to get kids to eat less picky food or whatever. And then I'm going to be sharing like parenting content where I'm going to say relatable things about how challenging it is to get our kids to eat well. And it's the stuff that's going to draw people to me and it's going to make them feel trusting of me. And then once they're trusting of me, then they're interested in what I have to offer. Like you have to play both roles at the same time with your audience. You have to be your audience, but you also have to be the person who's trying to solve your audience's problem. And the more in which they trust that the solution, the solution that you came up with, has come out of your own experience that's related to them, the more in which they're interested in it. So another thing to think about is, you know, I come from media, traditional media, but if you're posting on LinkedIn, you are functionally a small media outlet, right? Like you are now a small media outlet with a distribution channel, which is LinkedIn, and you're producing your own content, you know, at whatever cadence you're doing it at. And when you do that, you must follow the rule of what makes media successful. And I will tell you what that rule is, and it is this. You have to create the correct mix of predictability and surprise. So predictability and surprise. Predictability is to say that you are going to signal to your audience exactly what they're going to get from you. The reason that they're going to subscribe to you is because you're going to fulfill some kind of need for them. Daniel: So what is Mike Dirnt doing? He's fulfilling the need of I've liked Green Day since high school and I'm just going to keep following it. But like, I also follow people who just give good advice, right? I follow Robert Herjavec from Shark Tank because he offers good advice, and he's really smart on sales and operations, and I get smarter by listening to him. That's why I'm following. So you have to establish what your value is to somebody, and then you have to reliably, predictably deliver that so that they are always getting what they signed up for because they have to take the active role in signing up. But if you are too predictable, then you're boring, right? If you're too predictable, then why would I follow you if you're going to say stuff that I already know? Matt: So that's why you also have to be surprising. You have to be predictable in that you're going to deliver the right kind of value, but you have to be surprising in that I don't know the next thing you're going to say. You're going to say something that's going to make me think. You're going to say something that's going to challenge me a little bit. You're going to say something that's going to excite me. I don't know what that's going to be. Now, you can get the balance wrong. You can be too predictable and boring. You can be too surprising and a turnoff, right? So if I'm following a children's food brand and I'm getting great recipes for my kids, and then suddenly they start posting about politics, it's a surprise, but it's a bad surprise. And now I'm out, right? So you need to have the right balance of predictability and surprise. And once you do that, you build trust with people. And once they trust you, they are far more likely to buy whatever you have. You have to think, like, content builds relationships. Relationships build trust. Trust is the thing that converts. So always be mindful of that. If you're just promoting, you haven't done anything to build that relationship and to build that trust, and there's no reason for it to convert. Daniel: Is there a proper ratio of predictability to surprise? Because for some creators, and most creators actually, they probably have certain formats or posts that they made in the past that they know the audience loves and expects. And then there's this element of, okay, maybe I should test out a new idea or maybe I'll test a new format. With LinkedIn, it's like maybe I will try a video today instead of an image with text. How do you think about that mix of predictability versus surprise? I mean, it's going to be different for every audience, and it's going to be different for every brand or person. So the best thing that you can do is just start to experiment and see what works and find the cadence. And then you'll also find these things that can become a mix where they're promotional, but they also feel like content. Matt: So, for example, I work with the founder of a boba tea brand. Daniel: And what she found is that it's like a make-your-own-boba-tea-at-home kind of mix thing. And what she found was that the thing that performs the best on social, this is like social videos, a short-form video on Instagram and TikTok, is really fast-paced, process-oriented videos of making a delicious-looking boba, right? So, like, imagine the process of opening all this stuff up and pouring it in and mixing and ending up with a delicious boba, but, you know, kind of cut really fast, so it's like boom, boom, boom, boom, boom, boom, boom, boom. And like seven seconds later or ten seconds later, you've got yourself a delicious-looking boba. People, for whatever reason, love that. They love watching it. I think because people like process, they like evolution, they want to see where it goes. It kind of has a natural story arc, and then in the end, it looks delicious. And people like delicious-looking food and drink. So that is both content because it is serving the audience and it's giving them something that they like, but it is also promotional because, of course, it's her boba and she wants people to buy her boba. So if you can find ways to take your product or service and turn it into engaging content, then you get to do both at the same time. And there are so many great examples of this. You know, like there's this guy who has millions of followers on TikTok now where basically he's like, I think he just like has a lawn mowing company or something. I don't know, but he shows up at these homes, these very kind of worn-down looking homes with yards that haven't been mowed in who knows how long. And he just shows up and he offers to do it for them. And they say, okay. And then there's this time-lapse-ish video of him just cleaning up every part of their front until it looks amazing. And you watch it because it's compelling. You're like, oh my God, what is he going to do? How's he going to clean all that up? But at the end of it, you say, I want this guy to do that for me. Like I got to hire this guy. So it's a way to turn the thing that you're doing into content. So you should always be mindful of that, but it's just, it's experimentation. If anybody tells you a specific formula for exactly what to do for your brand without having run tests on it, then they're just making things up. Matt: So well said, Jason. And I think this leads to another interesting topic, which is with your own content, you've been creating content on LinkedIn for a while now, and clearly whatever you've worked, whatever you've written, whatever you've tested, has given you learnings that have allowed you to grow to the size that you are. What's your current process today for posting on LinkedIn? From the moment you get the idea all the way to hitting posts on LinkedIn. Daniel: Sure. So look, it starts, okay, let me break down. There's, I post different kinds of content on LinkedIn and they follow different paths there. Daniel: So that was why I was like working that out in my head as you asked me that question. Why this works, like what about this commercial works and what principle of marketing can you take away? So that's one kind. The other thing that I do is a lot of branding and packaging breakdowns. So I'll do these kind of comparisons of like an old, the old RX bar and the new RX bar, not new now, but you know, or the old Ollipop and then the more modern design of Ollipop. And then again, I'm breaking down what has happened in this shift. Then outside of that is what I consider to be my kind of wildcard stuff because those two formats work really well, pretty reliably. And then I'm always looking for new. So I'll be experimenting with new formats. I try to do posts every so often that kind of promote my speaking, but I don't promote my speaking by saying, I'm a great speaker, hire me. Instead what I do is I write posts about things that I've learned as a speaker, right? Like, here's how to be a better speaker. Here's a thing that I do as a speaker. I'm trying to drive that business. And then also, you know, different ideas on change, which is the thing that I talk about a lot. So it is all in some way or another about recognizing new opportunities, being able to communicate them, and navigating change. So the flow for all of these is different. Let me start by telling you this. The most important thing that you can do, I think, as a quote-unquote content creator, however you want to embrace that label or not, is that you start capturing ideas in real life. So do not sit down at your computer and try to come up with the thing to write tomorrow or today. You're going to get stuck. It's going to feel impossible. Instead, do this. Throughout the normal course of your day, as you interact with the kinds of professionals that you are writing for or the customers that you're writing for, right, depending on who your target audience is on LinkedIn, what do people ask you? What do people ask you and what are your answers? Have you ever given somebody a piece of advice and they said, that's really helpful, thank you. Have you ever fixed a problem and then thought to yourself, that was a good job that I just did. Like anything that happens that would be relevant for your audience, write it down. I do this in my notes app and my reminders app if it's two separate things depending on what I'm doing. But it's just in my phone. My reminders app is where I do this for my newsletter. So I have a newsletter called One Thing Better. Each week, one way to be more successful and satisfied and build a career or company that you love, you can get it, by the way, by going to onethingbetter.email, which is a web address. So plug that into a browser, onethingbetter.email. And I keep my ideas. I'll be talking to a friend or an entrepreneur and they'll ask me something, I'll give a piece of advice. We'll get into an interesting conversation. Daniel: And then I think, ah, that's a great newsletter right there, the thing that we were just talking about. So in that moment, do not wait, you will forget. In that moment, I pull out my phone, I open up the reminders app, I write a quick note to myself about what this is. And then the next time I have to sit down and write a newsletter, I open that reminders app, I look through, ah, that idea, I liked that idea. And then I write it. So similarly on LinkedIn, I am scrolling around Instagram, and I'm watching for great commercials that I have something to say on. And particularly great commercials that have performed well on Instagram, right? If you've ever flipped around the reels, you'll see, there are all these accounts that are just posting commercials. And some of those commercials do okay and some of them get millions of views. And for whatever crazy reason, our human brains love that kind of commercial. Just who knows why, but now I know that that commercial resonates with people. So now I take note of it. I grab the link to that reel and I throw it into my notes app. And I just keep a log of these things. And then the next time it's time to sit down and write a LinkedIn post, I open that up, I click the link, I was like, oh yeah, that Coca-Cola commercial, that's a good one. Let me see, do I have something to say about that? Yeah, okay, I do. And then I write it. So that's largely how I'm doing this kind of stuff. I'm capturing it in real time to give me a backlog of ideas so that when it's time to sit down and write, I actually write. Matt: This makes so much sense. And Jason, across almost all of the guests that we've spoken to, a lot of them have a very similar process where the inspiration doesn't come from just sitting at your desk and opening up a blank text box. It never does. Everyone's keeping track of ideas on their phone or in a notebook as they're going through their day, as they're having conversations with different people, different questions, thoughts come up and me personally as well, I've found that to be the easiest and most valuable source of information as well. Just going out there doing stuff, talking to customers, talking to partners, people like that. And being just a little bit more reflective on, okay, like take a step back, what did I learn from that experience or what did I learn from that conversation? What questions came up from it? And then turning that into a post, which more often than not will resonate more with the audience as well than if I were to just sit down and try to manufacture something out of thin air. Daniel: Right. So I also am dying to ask you this, Jason, because you mentioned you've spoken with Dan Roth and some of the other guys over at LinkedIn. As someone who's been on the platform for a while, is there anything that you would like to see them add or remove from the platform as is today? I know there's a lot of things changing. Matt: You know, they're trying to push video a little bit more, but curious in your experience, what do you wish that LinkedIn would add to the platform? Daniel: Yeah. I mean, I've had many conversations with them about this. So if anyone from the LinkedIn team is listening right now, this will not come as a surprise, but I'll tell you the things that I've told them. So number one, I think that their newsletter product needs to improve vastly. Like just, it just, it is just, it is such a missed opportunity. And it's not a good product right now, and it really could be. So I think that they need to improve that. And they know it. I mean, this is not a shocker. They're very well aware. And number two is this is very simple, but, just give the option for number one, hyperlinks. And then number two, bold and italics. Like just why, why have we not just added that? You know, you can go to typegrow.com or like other places where it'll do the formatting for you in those italics and bold in case anyone's ever seen that. It's like, it's actually like a totally different font that I don't, I couldn't really explain to you how it works, but you can, you could like take a post that you wrote, paste it into typegrow and then like kind of highlight in bold and italicize things and then copy and paste that into LinkedIn and then it'll show up. Like LinkedIn should just do that natively. Like I don't, I just don't know why that's not there. And then number three is you know, they are definitely trying to incentivize posting a video, but what I found for myself and what I've heard many other creators say is that video actually doesn't travel as well on LinkedIn as it should. So I don't generally feel all that rewarded when I post video, particularly vertical video. Like I actually, my advertisement posts do well, but that's in a, that's in a square format and it doesn't actually get ported into like the vertical video player that they have. And it works well inside of the post, but I don't think that they're doing the best job at actually driving video views and then any kind of value and engagement off of those video views. And then number four is you know, I mean, Dan has said to me that, that, you know, he's been at LinkedIn for however many years he's been there and like throughout that entire time, everyone keeps complaining that the algorithm is changing and that their reach is depressing. And and so he doesn't, you know, he doesn't seem to take those complaints all that seriously, but I will tell you that my reach is, is a fraction of, of what it was a year ago. I mean, the same kinds of posts just do not perform anywhere nearly as well as they do as they did in 2024. Something definitely changed with the algorithm. I mean, they're always changing the algorithm, you know, every day they're updating it and actually it's not even fair to say the algorithm because it's actually lots of different algorithms. Matt: And you know, they're trying to optimize for the best experience possible, but and, you know, Dan has told me that they really don't want things going viral on LinkedIn. They don't want people to turn it into like viral soup. They, they really want it to be focused on like value, but I'll tell you that I definitely am frustrated that it's become harder and harder to reach the masses and to grow my audience. Like my, my follower growth slowed significantly in 2025 compared to 2024. And I'm really hopeful that next year they, they take some kind of corrective action. I've I've heard some some kind of insider knowledge that's not, not ready for public consumption yet. That isn't directly about that, but it's about some other things and book you, for example, for, you know, whatever, for a talk, for a consulting, for something. And I don't think that those features are as clear and easy to find and use as I think they'd like. And I think that they also know that, so they're, you know, they're certainly rolling out more. And I know that small business, small and medium-sized business is a big focus of theirs now, so I think that there will be more of those tools. But I'd like to see that because I would certainly like to see how LinkedIn could help me drive more speaking engagements or drive more consulting work or any of that kind of stuff. Daniel: Jason, you've given by far the most comprehensive answer to this question. And we've asked it to pretty much every single guest. There's so many different directions that I would love to take this, but first of all, completely agree with many of the things that you said around, you know, the newsletter functionality not being great. Why can't you have bold or italicized text? It seems like such a basic thing that you should have in the native editor. Hyperlinks, right? Right now, if you're going to link something, you've got to put the whole thing, and it's not great visually. And some other things that we've also heard from other folks is the inbox for messages is a little bit cluttered still to manage. Also, I think you kind of touched on creator monetization a little bit, but seeing a little bit more of a focus on incentivizing creators on LinkedIn. If you look at platforms like YouTube or Instagram, TikTok, I feel like they do a lot more in terms of incentivizing creators to create. And so I would love to see that. The groups functionality as well on LinkedIn, I feel personally isn't great either, and there's a huge missed opportunity there. But yeah, these are... Matt: Yeah, I agree with that. You know, I mean, I sympathize. In the time that I've known the people at LinkedIn, I've seen them go back and forth a little bit on the way in which they engage creators, right? Like there was a time where they had a whole creator concierge team and I had somebody at LinkedIn who I was like checking in with every quarter. And then that all, that all went away. Matt: And then Dan told me that they've actually reconsidered how they even use the word creator because most of their users don't think of themselves as creators. And, you know, I, I totally get that. And the thing is that about like a YouTube or a, or a TikTok, you know, those are creator driven platforms where the vast majority of people are consuming, not creating. And that works really well for those platforms because you can get these large creators that then drive all that engagement and keep people coming in. And, but LinkedIn is actually trying to, and I sympathize with this, but they're trying to do something different. They don't want it to be a creator driven platform because what they want is they want the average LinkedIn user to gain economic opportunity from being there. So what they really want to do is create a feed that feels welcoming and open for anybody to be posting about anything and to see some kind of value on that. And I, and I get that, right? So if I'm, if I, you know, if I'm my friend, Matt Edelman and my job is to help the CPG brands get onto store, get onto target shelves, like that, you know, and that's what I do every day. Then, you know, I get to post about what is happening on shelves at Target and it's reaching, you know, a kind of a niche audience, but exactly the audience that I need. And that's turning into business for me. That's a success. That's what LinkedIn sees that as a success. And that's hard to balance with the desire for, for someone like me to be reaching 5 million people on every post, right? Like you don't want the feeds to be full of me's. You want them to be really as, as relevant as possible. So if you are in CPG, you want them to be full of Matt's, you know? And, and so I, uh, I understand the tension there, obviously as a creator type myself, I want more reach and I want more tools for creators. And the sense I get is that they are trying to find that balance over there, that creators are definitely on their minds, even as they're trying to, you know, properly serve that much wider audience. And so we'll just, you know, we'll have to see where it goes, but this is the reason I'm, I love fostering those relationships so I can at least weigh in. Daniel: Yeah, it's, it's fascinating you bring up the idea of economic opportunity being almost like a North star objective for. And that's their language, by the way, that I'm not coming up with that. Dan, Dan uses the term economic opportunity. Fascinating. And it makes a lot of sense then why it does feel different. It feels very different compared to a YouTube or an Instagram or TikTok. Matt: But I can definitely empathize with that as well as they try to figure out how to navigate that tension between, you know, catering to the pure creator types that just want as much reach as possible versus your average LinkedIn user or maybe business leader who, when they come on the platform, when they post something, their real objective is not just let me get a hundred, 200,000 impressions, but how does this reach the buyer that I'm trying to actually reach or how does this actually lead to the business meeting that I'm trying to get booked? Right. It'll be so interesting to see how they navigate this in 2026. I'm personally very curious to see where this platform goes. I only actively started posting this past year. So, you know, the stuff you were talking about 2024 algorithm versus 2025 algorithm, I haven't experienced firsthand, but if there are any changes next year, it'll be very, very apparent to me as I'm also posting. Daniel: There will be. I mean, that's not insider knowledge. It's just that they're always tweaking it there. So I'm sure something will change next year and it'll be interesting to see what it is. Amazing. Well, Jason, final question. Is there anything that we haven't talked about that you'd like to share with the audience before we wrap up? Matt: No, I think this is really great. I really appreciate your time and interest. Um, you know, go follow me on LinkedIn. You can find me at Jason Pfeiffer on LinkedIn. And then again, I'll just, I'll just shout out that newsletter because that's where I share, especially the kind of stuff that we talked about in the first half of this conversation about growth and navigating change and all that. And that is my newsletter is called one thing better, and you can get that at one thing better dot email. Amazing. Thanks for coming on. Daniel: Hey, thanks for having me.
