We interviewed a LinkedIn top voice about LinkedIn | #5

October 21, 2025

Intro

In this interview, Melissa Rosenthal, Co-Founder of Outlever, shares how she’s redefining B2B marketing through authentic storytelling and thought leadership.She discusses her journey from leading creative teams at BuzzFeed and Cheddar to building a platform that helps brands own their voice and audience. Melissa offers sharp insights on the future of content, authenticity, and how companies can truly stand out in a crowded digital world.Subscribe for more interviews to come!Follow Melissa on LinkedIn @melissarosenthal

Transcription

Daniel: Okay, I treat my LinkedIn kind of like a personal CNBC. Like that's how I imagine it. Everyone says to do that, and that's just not the way that my mind works. It takes a lot of sparring with AI to actually get it right. There's no way we could have done it without AI. Matt: So the investor thing is interesting because I think to get attention and to make noise, you have to be slightly controversial. Daniel: I'm so glad you brought that up. Okay, well, trick question because I don't believe in that. If you're gonna advertise on one billboard, you shouldn't buy billboards at all. It's not the strategy. So it's like, I mean, just, it's just, you know, all of our business at Outloud ever comes through my LinkedIn and through, you know, you know, LinkedIn flew out to me like six months ago to do like a profile on my career. Matt: Welcome to the Connection Accepted pod. Today, I'm really excited to have Melissa Rosenthal. Melissa, thanks so much for being here. Melissa Rosenthal: Yeah, thank you so much for having me. I'm really looking forward to chatting. Matt: Awesome. So Melissa, you have a really impressive background and something that I do with every guest, though, that we bring onto the podcast is I look at the first LinkedIn post that they ever made. And for you, and maybe I'll just share my screen here so you can kind of throwback here. This, I believe, was the first post that you ever put out on LinkedIn eight years ago when you were still at Cheddar. Matt: And so you said, you know, you can't be successful without a strong mission and vision. Proud of the Cheddar core values hanging in our office and inspired every time I walk by them. So take that all in. And then I'd love to ask you, like, what has changed since you made this post? Daniel: So two things. One, I think LinkedIn might cut you off because I was posting when I was at BuzzFeed as well. So I think, I think maybe that the cutoff date is eight years, but when I look at my records, my first post was probably like 12 or 13 years ago. So yeah, so a long time I've been posting on there. I definitely saw value in it like immediately, like kind of there, there was a lot there that was really interesting to me and it's evolved in many ways. Matt: What, what would you like, should we shape the conversation on what's evolved in my, in my career or what's involved on LinkedIn? And I mean, like there's so much, so there's so much there. Daniel: So happy to take it. For the audience's benefit, why don't we start with your career and just give them like the high level overview of all the events that have led you to founding Outloud ever today. Matt: Sounds good. Yeah. Well, my early days, I was at a company called BuzzFeed. I ran their global creative department and I started out actually as an intern. So my, it was pretty interesting. My when I was in college, I wanted to go into the music industry and I was interning from kind of freshman year and I was interning at very cool magazines and record labels. Matt: And I knew I wanted to be a part of it. So I fought my way in, you know, I had to be really persistent, but I eventually got that internship at BuzzFeed and it was like the best decision I ever made. It taught me so much about virality, about content creation, and it set me on a path that eventually led me to founding Outloud. Daniel: So I applied for an internship and the rest is kind of history. The company really started to take off and it was a really amazing time for digital media. And I, you know, I think it was pretty, pretty cool to be at the forefront of that. Flash forward a few years after that, my boss at BuzzFeed, John started Cheddar and I joined him to do that. We kind of had this contrarian view at the time, which is a very wild contrarian view to like even say it's a contrarian view. But our contrarian view is that people would cut the cord with cable and that streaming services would be the primary way that people would watch their content. It was on demand viewing at a appointment, what we called appointment viewing rather than through a cable subscription. And that turned out to be very right. So we built Cheddar and we sold Cheddar in 2019. And then I was sold it to a cable company, ironically. And then I went to decide to, I was like, I, okay. I really like digital media. I don't know if that's the future for me. I see the decline in a lot of what's happening here. What it was 10 years ago isn't what it is today. Where do I want to be? You know, tech and was on the forefront of that. And I was like, I need to, I need to be working at a company that I like believe in. And I looked at the tools that I was using and I was like, okay, if any of these companies like are a good fit, like I would love to do that, because if I'm not a user, I'm not a believer. Daniel: That has treated me very well in my like my career, so I kind of wanted to stick with that. And ClickUp just happened. And it was perfect timing. It was Series A. The company had big aspirations to go up against Atlassian. My consumer and digital media background was like a really good marriage to Zed, the founder, and kind of what he believed in his brand and how to grow ClickUp, because it's such a, you know, your ICP is one to thousands. And it's every ICP kind of across the board. You know, every, any team can use it of any size across any industry. So it worked really well to align that to a more consumer-focused strategy than B2B. So I ended up at ClickUp, honestly, like life-changing for me. It's that was kind of like I learned so much so fast and saw the company, you know, hyper scale to four billion in valuation. And, you know, now they're looking to go public, which is super exciting. And then after that, I was like, all right, I think it's time to take all the things that I've learned over the course of my interesting career and build something that I believe is the future of go-to-market. And that's that's where you find me at Outliver. Matt: That's awesome. And man, so many thoughts just going through my head right now. Even looking back at your BuzzFeed experience, I read an article somewhere, you were 25 at the time when you were leading a team of 30-40 people in the creative department. That's super impressive. Daniel: I mean, I'm 26 right now and I can't imagine doing something like that. And it was cool that I feel like you were at the company at such an interesting time in digital media. And like you were saying, cable shifting over to streaming services, that was another trend that was happening. And so you kind of got to see all of that firsthand. And then of course at ClickUp, that company was the company continues to be a rocket ship. So I feel like you've you've had a set of really unique and really interesting experiences that now almost like uniquely positions you to launch this new venture with Outliver. But let's talk a little bit more about OutLiver now. Where did that idea sort of come from? And when were you like, okay, this is, this is what I want to do after ClickUp. I want to help businesses become the number one news source in their industry. Kind of, it's like this productization of my brain over the past, you know, 15 years or so. And what it really is, is, you know, when I was at BuzzFeed and Cheddar, we were predominantly making money through advertising, through partnerships with B2B companies, especially at Cheddar. Daniel: And I was always thinking in the back, back, back of my mind, like, why can't these companies build their own authority through kind of the same motion that we're doing to build these media companies? Like, why would they not do that when they're spending millions of dollars with us a year to advertise? Why wouldn't they just invest that in building this themselves? And I think that was like a wild thought at the time because like media was such a, it was its own model, right? Like, you're building this authority, but really you're doing it at the end of the day, you're doing it to sell ads. Like, there's no ARR. It's not recurring. You're not building, you're building viewers, but you have to earn their attention every day. The model translates actually really nicely to a company that doesn't want to make advertising revenue from it, but wants to build relationships and trust with an audience. And I was always thinking about that. Obviously it wasn't the time to think about that because our, you know, the companies were doing really well. Advertising was going really well. But fast forward and then ClickUp, ClickUp, I had a really healthy marketing budget. And the problem I had was that it was really hard to have the amount of conversations that we needed to have to be able to reach our ICP 24/7 when they're not in the consideration phase, right? Like, you want to be top of mind. You want to have like a Geico billboard strategy. You want to be able to then funnel them down. Daniel: But like, if you're trying to reach everyone, it's really hard to do that. So without lever, it was like, what is the solution for the challenge that I was facing at ClickUp? And then the, the opportunity that I saw when I was in digital media. And that was, wait, why don't we productize this? Also with, you know, AI, there are things that we can do today and why we've been able to build OutLever that we would have never been able to do 10 years ago. So it's kind of that mix of like the thing that's been eating at you across your career and across your experience, the right place, right time, and then the ability to build this. And all of those things just kind of made sense. And it was like, let's go for it. Even if this funnels into something else, which now, like, I mean, we've been in market for a little over a year and we have like 40, like industry agnostic customers. And a lot of them are in enterprise. And like the things that we are learning on a daily basis, I mean, it's just like, it's gold to ship our, to. to be able to shape our product moving forward. That's a little bit about why I kind of started Outlever. And I don't know if I stated this, but basically what we do at Outlever is we create a hybrid newsroom approach. We build companies into standalone media organizations and build them a credible, basically, news motion that then also connects to their on-site motion. Daniel: So we're creating this kind of hybrid network approach to building them authority in their space. But it's also a lot of other things that it's really great for building relationships with prospects. It's really great for creating a ton of noise on LinkedIn using your ICP and your customers as basically as your own megaphone. And that's what we've built. Matt: That is fascinating. And I have a few questions, but let's start with just LinkedIn. You post a lot on LinkedIn and I'm assuming for your clients, you're probably helping them to produce content on LinkedIn as well. Was it always clear to you that this was going to be like the main platform we wanted to focus on? Or did you look at other platforms? Daniel: It is, and it isn't. Like, so the media companies that we're building them or the newsrooms that we're building them are not on LinkedIn. But LinkedIn is the predominant way that people, there's two ways that people are sharing the content and the distribution vehicle for the stuff that we're producing. One of those is LinkedIn and the other is direct, which is really what I believe in. It's like, where do people find content? They're not going to Xdomain.com. That's just like not a reality anymore. Even for those media organizations that are left, like, no one's doing that. Daniel: So how does content find the person? And that's through people in your like network sharing it to you, like seeing it on LinkedIn, right? And then the other piece is through Slack, through dark social, through email, through people you're connected to through WhatsApp. And those were the ways that we were like, okay, when we build a distribution vehicle for this motion that we're creating and this product, we have to incorporate LinkedIn. So how do we do that? Matt: So effectively, like LinkedIn, I mean, also like we made a post about dogfooding your own product. We dog food our own product. We have our own publication. But the entire, like, a lot of what, a lot of where our leads come in right now are predominantly both our motion and LinkedIn. So we're like, okay, well, we have to tap into the two things that are working for us, for our customers. And one of those is definitely, is definitely LinkedIn. 100%. That makes a lot of sense. And so what if I were to come to Outlever and say I'm like a brand and I want to turn my brand, I really want to amp up my presence on all these platforms and really create my own newsroom with Outlever. What's the process? Daniel: How do you guys go about it? Yeah. Yeah, tell us a little bit more. Matt: Yeah, so we've built a really amazing product and media listening algorithm. So we're listening to hundreds of millions of signals every day or every month, rather. And those signals are, they're everything. Matt: They're companies' websites, press releases, newsletters, product updates, changes they're making on their site, things they're saying on LinkedIn. Like it's this kind of like all-encompassing listening algorithm. So what we do is we align with our customers, hey, like, where do you see yourself headed? Like, what do you want to own? Do you want to be the agentic call center company? Like where can we like place you that can capture and be kind of like that net for everything that you want to own within that space and all the conversations happening in that space where it's a catch-all for the ICP that you want to attract. It's a catch-all for your current customers and any partners that you might be working with. And also like influencers in that space. So we align on that. We build out a brand new domain. It's a gorgeous news site. It's super legitimate. It's, it's, you know, it's, it's real news site. And then we go out the door and we do interviews with folks in that specific vertical or ICP set. And we talk to them about the things that are happening in that industry. We publish those articles on the news site. We've also published pieces of those in a new content format on our customer's site. And then there's an amazing distribution network that we have where we see a lot of people sharing out their articles because they're really proud of what we've written with them. And it's all on a megaphone on behalf of our customer. Matt: So we've created this like very interesting network effect of like using our customer's platform as a megaphone for what these people care about, but it also ties very closely back to what our customers care about. So it's a really nice kind of loop within that kind of space. Our team, we have journalists internally, but our product has really made them more efficient. Like we've productized journalism effectively. We've built a ton of tools internally that allow us to do this. It's a mix of, you know, task management, a CRM. We've rebuilt Fireflies to effectively learn and be trained off of interviews so that when journalists are on the call with subjects and sources, it makes them smarter. It understands what they're going to ask, how to discuss certain things. So we can make people really great interviewers. We can speed up the editing process. So it's really like, it is, when I talk about like my view of AI, it is kind of that perfect marriage between like utilizing AI. to do the things to make them faster. But the core piece of this is that these pieces are journalistic and the sources of the interview also have to be thrilled, because our customer's basically twofold. It's the people that we're speaking to on their behalf, and also our customer. So it has to kind of like, you couldn't do this with like AI slop, you know? So it really is like utilizing AI to make our journalists more efficient and more effective. Matt: And yeah, there's no way we could have done it without AI, this would not exist. This would be like a very unprofitable thousand-person company, but we're able to do it with the tech. Yeah, the AI slop comment, man, there's a lot we could go into there. Clearly, you know, there is more and more AI-generated content these days, especially on written platforms like LinkedIn. And I think there's people on both sides of the spectrum. Of course, there's going to be people that are saying things about how AI is ruining content and there's so much AI slop that's being churned out on a daily basis. But then there's also people that are on the completely other side of the spectrum, and they're like, we shouldn't use AI at all, or sorry, we should use AI, and these are like the people that are very on board with it. Now, I personally fall somewhere in the middle. I think it can be a very excellent enabler. And similar to what you guys are doing, it's helping the journalists. It's helping people to be smarter and to be more productive. But I want to dive into that a little bit more, actually, because I know you also posted a little bit about it on LinkedIn before. Tell me your thoughts around AI slop and as inevitably people are using AI more and more for their content, where do you think things are headed? Yeah. Matt: I mean, like, AI, it's getting smarter every day, right, but it still has tropes and it still has things that it goes back to that are just not human, a way of speaking and articulating. And it doesn't form its own perspectives. So our take on that is that, how do we get the human perspective out of the person and shape that using journalism and AI? So, like, there is a really interesting thing in which, like, there are really great people that we speak with and their initial, let's just call it, their initial like touchpoint for us or their initial signal is really not great. It's like they've written something using AI completely. And you're like, wait a second, like, this is a great person. Like, maybe it's like a CSO at a company, but it's completely AI generated. And we're like, well, they have a good thought. It's just not written correctly. Like, it's not, it's not bringing out their true, like, version of what this is. What we'll do is we'll speak to them. We'll have a 30-minute interview with them, and we'll spin that into a really great article. And now all of a sudden they're posting about that article for a week because it really, it really, like, showcases their actual views. They just couldn't articulate it themselves. And they used AI and leaned on it too heavy. So I think it's interesting. I think, like, but there's a little bit of that, like, dead internet thing going on where people are treating it like a brain, but it's just a database. Matt: And it's utilizing and being trained off of all the other now, you know, repetition of what's happening and what other people are posting that's also AI generated. And you see that, like, chain start to happen and it's not good. So, like, I'm definitely very fearful of that. Like, I think our motion is like the complete opposite. Like, I'm betting on people, I'm betting on human perspective. I'm betting on journalism mixed with that. I'm, you know, betting on a lot of things in that area. Daniel: But I see it happen all the time where, like, we're getting dangerously close to, like, it's just regurgitating old things and, like, AI content because there's nothing new that it's being trained off of that's human instead of AI. Matt: Yeah, that's a really interesting thought there. And yeah, as they train it on more and more, or as they almost like run out of human content to train it on, then what is it? Daniel: Yeah, that's the entire theory of dead internet. It's that you've run out of the models to be able to train it off of. So what are you training it off of? You're training it off of AI content. But if that AI content hasn't gotten to a place where it's, it's like, that content has evolved, then all of a sudden it takes a giant step backwards, which is like, where are we? Like, we don't really fully know where we are in that progression, like, ladder, but you can see it start to happen, which is kind of the, like, red alarm. Matt: Like no one's really, like, everyone's talking about it as a theory, but not something that's happening in practice. But I think it's already starting to happen in practice. Yeah, I'm curious when you say, and I know you had posted about this, like, the real challenge is humanizing AI written content. How, how do you go about humanizing a piece of content? Like, I've thought about this personally a lot because I, I post also on LinkedIn and trying to think about what makes a piece of content human versus, like, something an AI generated. Daniel: Yeah, I mean, it's definitely. But yeah, I'd love to hear. I mean, I think, like, first of all, you kind of just have to understand, I think you said the tells of, like, what AI is. Like, there's tells. Like, it's pretty clear, like, what it's adding that it's adding to everything else. I mean, my, my, like, let's just, I can take it back to, like, my own individual posting strategy, right? I come up with a headline or an idea or a framework of what I wanna write. I create a note, like an Evernote or a ClickUp task of. Like, okay, this is like the kind of what I want to go for. Like, maybe I'll write two sentences. And then later on, I'll try to like write in the rest as like the thought comes to me. And then I use AI to shape it into a post, but like an actually well thought out piece. But it takes a lot of sparring with AI to actually get it right and a lot of removing of things that I wouldn't say. Daniel: Because it still has to be my unique perspective. AI is just the thing that's like cleaning it up a little bit and maybe adding some meat to it. But it, it certainly takes a lot. Like it, it's not, it's not like one and done, throw it in there and it's perfect. Even if I have a pretty well, like, thought out framework of what I want to write about, it still takes a lot of massaging right now. Matt: Yeah. 100%. I, I can relate as well. For me, it's, I try to start with the idea, and usually the idea for me comes from maybe a conversation I had with someone or something I read, something else I, someone else posted something I saw and I liked it. And then I try to put my own take on it. And then I try to use AI as kind of like a, not a thought partner, but someone to sort of bounce it off of and be like, hey, what do you think? Daniel: Yeah, like a sparring, yeah, like a sparring partner, exactly. Matt: Yeah. I think you put that perfectly. I'm gonna use that going forward, sparring partner. Because you're not totally dependent on it, but you're kind of still using it and pushing back and it takes, I think, a level of nuance and, of course, attention and not just taking the path of AI. And taste and like understanding of like what you're like, there's nothing more cringe-worthy to me when then, like, someone is making an announcement and it's just like you can tell. Matt: It's like, I saw someone do this like a few months ago and it was like, the cat's out of the bag! And it's like, would you really say that? Like, you're not really saying that. Like, you don't speak like that. Most people don't speak in like cliches and tropes. They speak in actual thought. So how do you distill it down to thought and not just tropes? Daniel: Yeah. Melissa, I'm also curious. I know you kind of have started talking a little bit about the process, but how do you come up with your ideas for your own LinkedIn account? And then when you do have an idea, what, what takes place from idea to post? Matt: Yeah, it's kind of what I mentioned. The way that I come up with ideas is really like, I'm talking to marketing leaders and executives across every single vertical, every single role, every week. So, and also I'm reading LinkedIn and I'm reading, like, I'm ingesting so much. I'm my own media listening algorithm too. Like, we all are. And some of these things like really resonate or they're things that are very close to my own experience. I feel like the best way that I can write and when my posts do the best and when it's more, the most authentic is when I can relate it back to a real lesson or something that I've experienced and make a statement about that and like things that I actually am passionate about and believe in. Like, I don't believe in writing for writing's sake. Daniel: So some things that I'm like, oh, this might be an interesting topic, but then I'm like, I don't really have any real world experience with it. And maybe I'll pose it as a question or a poll, but I can't really write a piece about it because it just doesn't make sense to me yet. So I park it. But you know, some of the ideas, like it's kind of this just like free flowing, like a mood board in my mind of things that are like, all right, like I'll write a headline here and then I come back to it and flesh it out. And then I rework it with AI and I try to queue things up. Like the best thing I can do in my LinkedIn capacity is queue things up for the next two weeks so that I have the free enough mind to not worry about having to post content every day. But so that the content just kind of builds in its own library. Matt: That's impressive. Queuing things up for the next two weeks. I was gonna, I was gonna also ask you if you follow any sort of framework or structure if you're, say, posting five days a week, do you try to get two of those to be thought leadership and then maybe one is like a case study? And, you know. I'd love to hear your thoughts on that. Daniel: Everyone says to do that and that's just not the way that my mind works. Like, I need to lean into, also I'm running a company, but like, this is a part of what I do, but it's like 99% not what I'm doing. So it has to be like really easy for me to do it and I don't want to stress out about it. Daniel: So following like a framework of like how, like I would never be able to do that right now, which is like, oh, I'll do three case studies a week and this and that. I try to strike a balance between things that are self-promotional and things that are just like my own thoughts and like authentic observations about the things that I care about and I'm passionate about. So I think it's like a balance between being like overly self-promotional and shouting from the rooftops the things you believe in and trying to do that in like a non, like just a very authentic way, I would say. So I do try to balance that, but in terms of like every Wednesday, I post to this. I can't do that right now, but, and my brain isn't really working that way. So I want to lean into what makes it easier for me. Matt: Yeah. Authenticity has been crushing it on LinkedIn lately. Although, although sometimes people are a little too much, you know. Daniel: Yeah. It takes a little too much of anything, I think is, is not good. Yeah. I mean, the other thing I'll say is like, I, I think I was talking to someone about this on another podcast, actually maybe Anthony Canada. And it was like, um, what like level of yourself, like how much of yourself do you share? And I, I was saying, okay, I treat my LinkedIn kind of like a personal CNBC. Like that's how I imagine it. And it's like, if I'm going to go on CNBC. Matt: Will I, would I speak about this thing? Like, am I comfortable enough talking about it? Is it, does it make sense in a forum for business? And if the answer is yes, like I will do that. A part of that can be a part of my story, sure. But I think there is definitely boundaries that I have in which like, I don't think things are appropriate to post on LinkedIn. This is not your close friend's network on Instagram. And like, I don't love when people use it that way. I think it's a little much. Like, this is still a business platform. But, you know, to each their own, but that is definitely like kind of the way that I think about it for myself. Daniel: 100%. Yeah, I was talking, I mean, I've talked with a number of founders recently, and I tell them like, hey, if you wouldn't want your investors seeing this, then don't post it, right? Matt: And, yeah. Well, there's about, there's also, that's actually an interesting point because there is, there's also a balance of like overthinking that because like what will actually get traction are things that like are a little bit controversial, 100%. Like you have to have some sort of take that like people are going to want to create a dialogue around. I also hadn't stated this earlier, but I think if you're not creating content that people want to have a dialogue around in any capacity, like from a content marketing strategy to your own LinkedIn strategy to what we're producing, don't create it. Daniel: Why would you create content that no, that people don't have a perspective on or that could be a little divisive? Like I think that's very important. So the investor thing is interesting because I think to get attention and to make noise, you have to be slightly controversial. Like with Buzzfeed, I learned this, like, this is 101 and how do you create social viral content? It's creating something that sparks dialogue. And some of those things are slightly divisive. So I don't know about the investor thing. I mean, luckily we don't have investors, we're self-funded, so I don't have to worry about that. But I certainly do think that way. Like, obviously I wouldn't do anything that would like completely turn our customers off. Like, I'm not going to say crazy things, but do I want to like be a little controversial sometimes? Yeah, absolutely. Matt: Yeah. No, I agree with you. I think like, and maybe there's more of this in B2C marketing and only B2B marketing is starting to see more of this, but in B2C, we see people doing all sorts of controversial stuff to get attention. And it works, right? Like it works. Daniel: Yeah. Agree on that. But in B2B, I think historically it's been kind of seen as more boring, you know, more logical. You're appealing to other businesses, so not as like emotional. But then the thing is, you are trying to reach people. So I think more and more people are realizing that. Matt: And there is a space, maybe not to the extent of some of the B2C marketing tactics we see out there today, but there is a, there is room for B2B marketers. Yeah, I mean, the reality, like this is a funny thing, but like when you think about, like, not that you can repeat this or that you'd want to repeat this or that it's good for you necessarily, but like the astronomer scandal. That's the best thing that could have ever happened to that company. Like I dare someone to tell me otherwise. It was the perfect layup for them to be able to say, okay, we're going to do something about this. It's easy enough to like, you know, the crisis comes, it's easy enough to be like, all right, we're going to fire the CEO. We're going to make a statement that we did it. Now we have hundreds and hundreds of millions of eyeballs on our company. We can do something funny, which they did with Gwyneth Paltrow. Whether you like it or you hate it, they did something. And now everyone, astronomers are a household name. So, you know, it's like, and, and I mean, companies like B2C companies do stunts all the time. Of course, it's not this level of a, of a, you know, an execution or what this is, but it's, if it's not detrimental to your business, it's good. Daniel: Attention is good. Brand awareness is good. 100%. And I'm so glad you brought that up because that's such a, that's such a great case study of like marketers today need to be opportunistic as well. Matt: And when events happen like that, yeah, it could be seen as a negative, but clearly someone at the company was smart enough to, to think, hey, we should take advantage. Yeah, yeah, brilliant. Brilliant. Like rather than not just say anything, the entire world had their eyes on this company. Like you got to do something with that. And they did. Daniel: And yeah, I mean, it's definitely impressive that they were able to pull that off in like a week. Yeah. That person deserves a raise. Matt: Yeah. Yeah. Also, I, I can't imagine what those meetings were like, but uh, yeah, for sure. I would have loved to be a fly on the wall there. Same. Daniel: Shifting gears a little bit though, I want to talk LinkedIn metrics. So how do you, for you or for your clients, how do you kind of measure success? Are you looking at impressions? Are you looking at like, did people actually engage in the dialogue? You know, are calls being booked, things like that? How do you think about success metrics on LinkedIn and more broadly? Matt: Yeah. I mean, for me, it's like, I know I can write a post that does well. Like I, I know kind of what that formula is and that doesn't necessarily get me in balance for leads for my own company, you know? So I don't think impressions are equivalent with metrics that I care about personally. You know, I, I think, can I hit the right people and can I say the right thing? And even if my post gets only a few thousand views or impressions, but I'm, you know, booking 10 demos out of that and. Daniel: And I totally get why some people may not like that approach. It challenges the traditional hiring norms, but honestly, if it gets us the right candidates who are excited about our process, then it's worth it. The goal isn't to just go viral for the sake of it but to make sure we're attracting people who resonate with our company's values and mission. And sure, there are some negative reactions, but at least it's sparking conversation and making people think about different methods, you know? What do you think about experimenting more with unconventional content like that, Matt? Matt: It was like a lot of the, I don't know, it's like a crowd on LinkedIn that I think, like, doesn't like that type of way of, I don't know, exactly. Um, but I ended up on like LinkedIn lunatics on Reddit and the post got like 500,000 views, but it was really bad. Like people were sending me like pretty nasty messages. And, um, you know, like, I would have taken like five, I don't like, who cares about that reach? Like that reach is like absolutely meaningless to me. It's all the wrong people. So 500,000 of the wrong people. Daniel: You know, it's like, great, sure, like people will see me in the feed, but like it's just not, that's not like valuable. That's fascinating. I think I may have seen that post as well. It didn't trigger me in the way that I think it triggered other people, but yeah, it's interesting. Virality is a double-edged sword for sure. And I feel like for most businesses that are posting primarily because they want to attract the right kind of customer to them, then virality is not really as necessarily as effective. I don't wanna say it's not effective because look at the astronomer thing, but that shouldn't be the priority. Matt: Yeah, for sure. I mean, I don't really know that many, like, I've never seen a B2B company that's really outside of like ClickUp, what we were doing and like what Chris is doing at ClickUp now, like that's optimizing for virality. Like no other B2B company is really doing that. Daniel: So, I mean, there's also, like, there's kind of this in between, right? There's like optimizing for pure virality, which is like the ClickUp model of like how they advertise. And they also have like, obviously ClickUp has a very well-oiled go-to-market function where they're creating all types of content. So I don't wanna just say they're optimizing for virality, but that is one of the plays. Then you have companies that I'm being very honest, they're creating like really bizarre, very like inner circle, inner monologue content that might sound good between like the two co-founders at the company, but it lacks the self-awareness that no one else cares. And I think like there's like a level of, like you have to have awareness about, like what you're putting out there because it, a lot of it just falls flat. Like content, like content isn't created equal. Like all content isn't created equal. And you kind of know that, but like, there's an like, just because you're creating a video doesn't mean it's a good video. So I think there's like an element and people are all, like talking about this term these days, but taste. Like there is an element of taste and like, why are you creating this and what is it doing? Like, you're creating like what, like a game show about something and hoping like people tune into it? Like, maybe, maybe, maybe. Daniel: But I mean, I really see it as like our approach at ClickUp was much more like how do we, and Outliver too a bit, is like how do we tap into like the, the water cooler content that people within the industries and verticals care about enough to reference us when they're speaking about it? Like, how do we trend jack? How do we think about the really, the things that like they are going to want to bring up within like their like meetings because they saw it and it was funny or it had an emotional impact on them in some way, right? That's how we thought about the frameworks of like what we created at ClickUp and also making noise for sure. Matt: But it was never like, so like, wow, did those guys just sit in a room and like all laugh and thought it was a good idea? Because that's a lot of what I think, like I see on LinkedIn is a lot of B2B companies putting out content that like no one else is going to find valuable. It's just like good to them. Daniel: Yeah. And taste is tough because it's like something that it's hard to teach. It's sort of acquired. Matt: Yeah. Yeah. I mean, I definitely like my, my thinking on that is like a lot of that, like, and why it feels like kind of innate to me is the BuzzFeed, like growth, right? Like I grew up with BuzzFeed. So my way of thinking about how people communicate and why they share and engage with content was kind of built on this framework of like different emotional... Daniel: That's interesting. I think a lot of the time with platforms, there's this initial push, right? They try to incentivize a certain type of content because they're trying to shift user behavior. But whether it naturally sticks, I guess, depends on how it resonates with the users as well. And if you think about it, there's always been this trial and error phase with every platform trying to find the balance between what they want to push and what users actually gravitate towards. Do you think LinkedIn is doing this more because they want to attract a different type of content creator, or is it more about diversifying the kind of engagement that happens on their platform? Matt: That's a great question. I feel like on some level, it's both. I mean, they're definitely trying to pull in creators who are comfortable with video, because that's where a lot of attention is, right? But at the same time, I think they recognize that they need to diversify the types of content on there to keep people engaged and spending more time on the platform. Daniel: That's definitely my personal like observation on like the, you know, I don't like to look at like anomalies unless it's like statistically significant. So it's the same way of like when people are like, well, look at how Harvey and Cursor grew. They grew to 100 million in revenue in like two weeks. And that's like, that's an anomaly. It's not a repeatable thing. And there's not a ton you can learn from it to any other company. It's not like that applicable. Same thing here. It's like if there's a viral video or viral startup video or liquid death post something and they're using that as like the statistical significance, it actually isn't that accurate. The answer, the short answer is no, I actually don't think video content performs as well as text-based content does. Like I post, mostly I just post like clips of podcasts that I'm on. And I find that that actually does really well. It's really like quick videos. I find that I drive a lot of people to the longer podcast through those clips. And it's just more content for me. Like it's mutually beneficial. It's good because I'm on this podcast, but then I get the clips and I get to share it out. Kind of just like works very well. No, I don't, I don't like, I'm not like a, I think video is the future of LinkedIn. I don't think it is. Matt: Yeah, that's really interesting. And of course, we'll, we'll definitely get you lots of clips for from this podcast. I want to really quickly also get your thoughts on commenting. Daniel: So on LinkedIn, comments are almost like mini posts. You can get thousands of comments from just commenting. How do you think about that? And when you're commenting from your account, what's going through your head? Are you like, I need to comment this amount? Matt: I'm so glad you brought that up. I don't have a full strategy, but what I do do is like when I'm in my feed looking at posts, if I find something that I have a unique perspective on where I can do a response, I'll do it. The other hack, which is, you're very right, they are mini posts. Some of my comments have more impressions than my actual posts. Like I posted, commented something on someone's the other day and it has a hundred thousand impressions on that on that comment. That's crazy. Daniel: It's crazy, but there's a way to tell when it's going to happen. When the post itself is going viral, I always comment on it because I know that I will at least get a pretty good amount of impressions. So even if I really don't want to comment on that post, I'll comment on it because I know the visibility is going to be super high. Matt: So yeah, I optimize my commenting for the things that I can actually uniquely add a perspective on and then anything that's going viral, I tap into because I like to hijack that for myself. Daniel: That is, that's huge. I'm going to definitely start doing that. Matt: Yeah, you should do it. Daniel: Yeah, why not? It's a shared hack. Matt: Yeah, that's awesome. Daniel: And I definitely, for some of the clients that I ghostwrite for as well, I tell them, Hey, LinkedIn isn't all about just posting. You have to engage. You have to talk to people, you know, it's a social media platform. It's not just... Matt: Yeah. Yeah. Yeah. It's, it's again, it's about dialogue. Like your people are adding dialogue to your comments. You should also contribute that back to the community. So I believe in like, almost like, yeah, it's a good thing to do that anyway. But yeah, I mean, I come across people all the time that have inbounded me from a comment that they saw too. And it's like, oh, I saw you. I think I saw you post this comment on this person's post. And I'm like, I don't know who that is. But like, I definitely did it, you know? I'm like, but it's not even like a stream of consciousness because I'm just doing it. And I know that I'm gonna reap the rewards of, of being able to do that. And, you know, obviously it compounds over time. Daniel: Cool. One more thing I wanted to talk to you about is billboards. And this is less focused on LinkedIn, but I, I know you love billboards. So if you could only, if you could only, I guess if you could, if you could only advertise on one billboard for the rest of your life, which one would you choose? And yeah, I guess what would you put on? Matt: OK, well, true question, because I don't believe in that. If you're going to advertise on one billboard, you shouldn't buy billboards at all. It's not the strategy. Matt: So it's like, I know you weren't expecting that, but that's what I will say. The only other thing I'll say is that airport billboards are insanely, insanely effective. Like airports, like by and far, like business travelers, you know, I guess it depends on who your ICP is, but valuable real estate. But yeah, you can't just buy one. It doesn't work. What would I put on it? Something like really controversial or something that would make people mad. Not like offensive, but controversial. If you're not going to make people mad with a billboard, then don't, don't put the billboard up. Like I, I don't know if I believe in this company. Like artisans billboards are perfect. Yeah. Like, yeah, talk about replacing people and get people really angry about it. Like that is a great strategy. Whether they hate it or they love it, they're going to talk about it and you win. Daniel: That's it. I love that. It's, it's thought provoking and it, it sparks conversations. Matt: Yeah, it sparks conversations. Again, like you're spending all this money to put like yourself on this, the largest like stage that people are going to have to like drop what they're doing to like look at this. If it's not, if it's not forcing you to take an action, whether it's making a post about it or commenting on it when you see it or referencing it or doing or going to the site to check it out, like then don't do it. Yeah. I have one other question as well before we get into our last segment, which is measurement. Matt: Do you guys track the ROI on the work that you're doing for your clients? If so, how do you do it? Because one of the things I think that marketers tend to struggle with is like with content, it can be a little bit tough sometimes to track the attribution. Daniel: Yeah, we, I mean, we do like ROI is also like in the eye of the beholder a little bit. Like ROI across every single company we work with, like, is sort of different and they don't all understand how they look at it and they all look at it very differently. So, we track very specific metrics and then we're like, make, make them out to be what you want to be. Like, in many instances, we are, like, companies are selling deals, right? So, there's like actual dollar for dollar like ROI. And if you sell it one deal, most of these companies, this pays for itself. But everything else, like, we are sharing impressions, of course. We're sharing engagement data on everything. We're sharing how many C-level executives within your ICP set we're speaking to, the quality of the content, how many shares, who's actually looking at these articles, what they're doing. Like, we're tracking like a lot. And I think it's like, there's so much data that we're continually refining, like how to, how to enable the data to tell the better story and actually make it really actionable for our customers. Like, that's the toughest thing. Like, it's not, it's not like tracking metrics. Daniel: Tracking metrics is easy, but it's outcomes and stories that enable them to do what they need to do to sell deals. Like, at the end of the day, that's, that's the best way that we can operate. So we're continually, like, evolving ourselves towards that, but we track, you know, a ton of different metrics, a ton of different things that ROI is, is different for different people. Some people just want us to show up in search. They don't care about selling deals as a result of this. Some people really care about that. So kind of just depends. It's really interesting. Like, I think in, when you're in your own world within a company, you live in that company's world. And now that I have customers in every single, effectively, like every single industry and across a lot of different ICP sets, everyone thinks about things so differently. And I, I didn't realize that. I think I, I expected, like, what we did and how we thought about things at ClickUp to be kind of uniform across like most companies and it's, it's very not. So I don't know. That was, it's just been a very interesting learning for me that, like, companies, even companies in similar spaces, just think about things, like, completely differently. And I think it's all like, it's definitely like, you know, founder, right? Like, it's founder influenced. Like, how does the founder view this? Like, I mean, that trickles down to probably every department within the organization, but just a very interesting insight. Yeah. Matt: No, that's really interesting. And it's cool that you do get almost a bird's eye view of how all these other companies are doing it. It's, it's the best thing you can ever do as a founder. Like that is, even if our product, like, you know, shape shifts in the next few years and we become something completely different, or it evolves, like, it's all because we're just internalizing everything that all these different customers are telling us. And we're like, we want to sell up your problems, right? So it's, yeah, it's a wealth of knowledge. It's a goldmine. Amazing. Cool. So now we're going to move into the last segment, which is good idea, bad idea. So Melissa, I'm going to give you rapid fire, a bunch of different ideas, and you're going to just be completely honest with me whether you think it's a horrible idea or the best idea you've ever heard. Sound good? Daniel: Are these, are these like, what kind of ideas are these? Matt: They're mostly related to LinkedIn. So yeah, let's do it. Our first one is vlogging on LinkedIn. Daniel: Depends. Depends how it's done. Vlogging does work. I think it's like, no one wants to see you at the grocery store. Like, no one wants to see you, like, at the gym. But if you're videoing yourself talking about something important and you're actually creating like a really great narrative and talk track, I think there's nothing wrong with that. I actually like it when people do that. It feels like very honest and authentic. Matt: And take it like you're in the room with them. But no, I don't want to see you like at the supermarket or at the gym. Daniel: Fair enough. The next one, posting five times a day on LinkedIn. Don't do that. Don't do that. I mean, like, first of all, I think LinkedIn, like, I don't know this for sure, but I think it definitely starts to ding you after you post like three times, for sure. There's something that happens. I don't know exactly what it does in the algorithm, but it definitely triggers something. But also, like, I don't know who, who that's good for. Like, why, why do you need to post five times? Also, like, optics are horrible on that. Like, are you, do you have nothing else to do but post on LinkedIn? So if you're doing, saying that you're doing anything else, I think people start to doubt that you're even doing that thing because all you do is post on LinkedIn. Matt: So don't do it. That's funny. Man, I wish Daniel, my co-host was on this call because over the summer. Not five, but there were days over the summer where I think he may have posted three or four times. And it was interesting looking at the data because the algorithm didn't seem to necessarily penalize him. He continued to get more impressions. But I think there may be a question around like post fatigue. Daniel: Post fatigue. Also, like, it's not, it's not, I'm not going to call it X. It's not Twitter, right? Like, it's just not. It's not meant for that. So I think like, yeah, don't do it. Matt: Valid. Cool. Daniel: Next one is a little bit less controversial, but LinkedIn reposts. Depends. I would say like, they're kind of not that valuable. Like, reposting feels a little like a cop-out unless you're adding your own thoughts to it. I think if it's something that's highly visible and you want to cite that person, it's okay. But I think you're not going to certainly get as much share of voice if you make an organic post and then just tag that person and tag their original thought. So anytime I'm going to repost something, if it's like, if it's important enough for me to repost it, I'm going to take that and I'm going to create an organic post around it. And then I'm going to tag the people that I'm quoting or referencing as their original thoughts. So I would, I would do kind of like anything to avoid a repost. I just don't, I've never seen traction with them. It's not like I, it's a bad thing necessarily. I just don't see like a ton of value there. Matt: Yeah. I've also tried reposts and also reposts with thoughts. And I've just always, the engagement for some reason. Has never been as good as if I just decided to write up a standalone. Daniel: To post yourself. Matt: Yeah, exactly. That's why I always optimize for doing that. Also, if it's important enough for me to want to repost it, I can figure out something to say about it. Daniel: Yeah, that makes a lot of sense. And I'm totally on board with you there. Cool. The, the next one is a little bit different. So connection requests. Matt: LinkedIn has a limit and it feels like this limit is kind of like a soft ceiling because I've noticed some people with premium can send more than others without it. But like, what are your thoughts on maxing out the number of connection requests that you send every week? Daniel: Yeah, do it. Do it. I mean, I, I don't do it. I don't know if I have time to do it. But anyone that comes into my network that I'm like, oh, this could be a good company for us to work with. Or this is a good person I want to be connected with. I will a hundred percent, like send a request to. I probably don't max out what I'm allowed to send, but I also accept like 98% of all inbound requests too. So I have a crazy amount of people that I'm connected to. Like it's 20,000, 30,000. I don't know, something ridiculous, which makes it like less effective when people are like, oh, we have a mutual connection because I probably don't personally know that person, even if they're connected to me. But I do, I'm a big fan of maxing out your connections. This isn't a closed network anymore. Like it's evolved past that. It's a, it's a platform for growth and it's a platform for distribution. Maxing out your request is definitely a good idea. Matt: Awesome. And then last one here, paying for LinkedIn premium just to see who viewed your profile. Is that a good or a bad idea? Daniel: I don't think that's a, it's a weird idea. I mean, paying for LinkedIn premium just to see who viewed your profile. Daniel: If they, if there, if there is enough of an impetus for them to do something, they're going to take an action. I don't think, like, I think people window shop a lot. Like I can see who viewed Outliver and I don't, I don't go after them. My goal is like, all right, well, if they viewed this and it's a good person, I'll connect with them on LinkedIn for sure. I'll like send them a note or a connection. But I don't like, I don't know if it's like, I don't know. I don't know. I think LinkedIn premium, do I pay for it or like, I might be because I'm like a creator. I have like a LinkedIn badge. They might give it to me for free. I mean, I think it's a good idea to have it. I think like if you can afford to pay for like any sort of like, you know, premium version of the product, like they definitely like prioritize you in some ways for sure. You have access, early access to things. You get more analytics, but I think there's a lot more to it than just paying for it to see who viewed your profile. I think there's like a lot of analytics. If you, if you want to ever do partnerships with brands, like you kind of need to have it. Same thing with um LinkedIn, like what you said, maxing out connection requests, you get a lot more of that. You're allowed to send more in mail. So there's a lot of benefits. I wouldn't do it for that one reason, but there's a ton of like upside. Matt: Yeah. A hundred percent. Totally agree with you. Daniel: We actually had a conversation with Peter Walker, who's the head of insights at Carta. He, he was saying that people seem to sometimes forget the fact that compared to other social media platforms, LinkedIn's actually done a very good job in terms of the fact that they have a massive base of subscription revenue that Instagram, TikTok, YouTube, I mean YouTube has subscription revenue now, but. What was, do you remember, did LinkedIn say that they just crossed a billion dollars in LinkedIn revenue? I think I read that like maybe a month ago. Matt: It was like astronomical, like what they've built with the subscription. Daniel: Yeah, I think it was a billion. Matt: Wow, yeah, that's incredible. I'll have to look that up after this, but I wouldn't be surprised if they did. They've done a really good job at that, and of course the fact that they've been able to be, I think, the only, I mean there's probably competitors, the only social media platform where it's like primarily people doing business and networking, very professional focused. They I think people forget that fact. I mean, it's like they evolved quite well in understanding that it was becoming a social platform and to feed into that because it wasn't like when I was, you know, when I made that cheddar post, like it really like wasn't like 99% of the people that post on there every day today didn't do that eight to 10 years ago. Matt: So I think for them to be able to have fed into the fact that they saw it evolving in that way was super smart. I mean like that, that was like a very, it wasn't a fast evolution. Yeah, I mean it's really, really, really smart. What they've done and the creator tools they've built and the experimentation, like not everything works for sure, but like they've experimented quite, quite a bit. Like I did, actually linked down, LinkedIn flew out to me like six months ago to do like a profile on my career. And yeah, like they have a whole like content team internally to tell people's stories of people that like, you know, are on LinkedIn and have great career stories. So they've definitely like, they have an entire editorial team and, and I mean, they're really like heavily invested in it, which is great. I mean, that's why it works so well. Daniel: Yeah, that's awesome. And we're actually trying to get Daniel Roth, the head of content, I think, at LinkedIn to come in the pot at some point, so stay tuned for that. But Melissa, I guess last question then, is there anything we haven't talked about today that you want the audience to know about LinkedIn or about Outlover? Matt: Yeah, I mean I would just say like, you know, my parting thought is that people are going to be what drive your business forward. Like it's, it's people, it's trust, it's personality, it's authenticity, it's having a clear voice and having taste. Matt: And I think like all of that starts with taking an action and I think you can be pretty deliberate and intentional every day on like what that action is. And for me, it definitely is like posting a thought, like using it as like a journal, like a business journal of what's happening within my own company. And when I think about the amount that I've gained from LinkedIn and content posting over the years, it's like, it's not really measurable. Like it's, it's in a good way. It's given me so many amazing opportunities. I've connected with so many great people, speaking engagements, like, um, I mean just, it's just, you know, all of our business at Outlover comes through my LinkedIn and through, you know, you know, podcasts like this that I then post on LinkedIn. So I would say like, it's wild to even think that like, this is a question at this point, but if you are in business or you like wanna stay in business and wanna stay employed and employable, doesn't matter who you are, you should be posting every day. I think like the one thing also that you can take away with from any company that you're at, and obviously we know how volatile the job market is now and will continue to be. Daniel: It's your personal brand and having a voice and a unique and clear perspective because that's why someone's gonna hire you when they're looking in a pool of a thousand candidates and you stand out because they understand exactly what you're going to bring to the table because you've been speaking about it and showing examples of it. So the best thing you can do is, is start posting every day, having a clear perspective, just do it. It might be painful at first. It becomes a muscle, but I think optimizing for that in your life is a really great stepping stone to wonderful things. Matt: Yeah, I can't recommend doing that like enough. Couldn't agree more. Awesome.

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