How ClickUp Built a B2B Social Machine with Chris Cunningham from ClickUp
55m 43s
The transcription features Dave from Exit Five discussing B2B social media strategy with Chris Cunningham, a founding member at ClickUp. Chris emphasizes that most companies mistakenly treat social media as an ad platform, while users want to laugh, learn, or feel something. He advocates for a rule of three: content must entertain, teach, or evoke emotion, and must have a strong hook and pacing. Chris recommends creating content primarily for two platforms (e.g., short-form video and LinkedIn) and using Instagram Trial Reels to test multiple versions of each video, as the best-performing version often surprises creators. He shares how ClickUp manages 35 accounts, including a separate comedy page that has more followers than the main brand, and uses AI to identify high-value followers like the CEO of McDonald’s. This approach has driven real sales, such as a large deal with VaynerMedia. Chris advises marketers to understand their ICP deeply through interviews, finding humor or educational angles unique to their audience, rather than just promoting products. He stresses that social media success requires patience and a commitment to creating content that resonates emotionally or practically, not just broadcasting ads. The conversation also touches on measuring impact through pipeline generation and using social as a signal for sales outreach.
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It turns your data into something you can use in the moment. Head to vector.co to learn more. That's V-E-C-T-O-R. co. And if they ask you how you heard about them, tell them exit five please. See ya. (upbeat music) Social media is not an afterthought for B2B companies anymore. It can't be, it's 2026. Your buyers are on their phones, they're scrolling Instagram, they're watching TikTok, they're on LinkedIn, which is more like a social media platform than ever before. But most B2B companies are still treating social like a place to post, say, blog links from the company page or post about the new webinar that you're doing. But there's another way. Chris Cunningham is a great example of this. He is one of the founding members at ClickUp. He's been there almost a decade and built their entire social operation from scratch. He told me something that I think every B2B marketer needs to hear. 99% of companies are just talking about their product on social. That's the wrong thing. When people plot their phone, they want to laugh, they want to feel something, they want to learn. That is exactly the opportunity. Chris walked me through exactly how they do this at ClickUp, how they run a weekly writers room and now shoot 12 to 15 videos every Thursday, how they A/B test every video, every version. There's multiple versions of the hook and the headline using Instagram trial reels before it hits the main feed, how they find unknown creators with, say, 4,000 followers and maybe one mini viral hit and reach out to them to try to turn them into full-time writers for ClickUp, how they manage 35 accounts across every platform and how this strategy has actually driven real pipeline and results. We talk about how to measure this, how to think about this and he gives a couple of great examples. Then the conversation shifted into AI and content creation and I asked Chris about where he thinks AI is going with creators and social media and content and he thinks that actually doubling down on real human creativity might be the biggest competitive advantage in B2B right now. This episode is jam-packed, it's all about B2B social media and join my conversation with Chris Cunningham. So Chris Cunningham, founding member of the marketing team, at ClickUp, you've been there forever now for 40 dog years and tech years or whatever. What has it been? Has it been a decade? Almost. I've been here for five or a decade, about four months, been a decade, two months, actually, two months now. In a world where most people I talk to myself included, I'm jumping around to a new company every two years. What's kept you at ClickUp for almost a decade? The founding team, man, these are my best friends. This wasn't the first company we started together. We've been through three different ventures together. We've had ups, we've had downs and I got to see this through. Like sure, I've had opportunities to leave, especially with things popping and doing well. But I love this crew, I love this team to see this through and who knows what happens being the future, but it's the team. Okay. And then how do you, you've played a bunch of different roles in the company as it's grown? Yeah. My view, and I'm not super close to ClickUp or what you're doing. So I'm not going to try to explain it for you, but back to the fuck it, it's my podcast. So like closely, I see you as like B2B. The reason I was drawn to have you on the pod is because, I think it might have been in a conversation with Tim from Atrefs, or just, I've been on your content for a while. And you talk about my favorite subject, which is B2B marketing and social media, and you seem to have a point of view on how it works, why it works. And so it's been, we've been like two ships passing in the night for a long time, but I want to have you on to talk about that. Am I true in kind of reading that, like you've carved out this interesting role in social and content in the company? I think I've made up my own role from being honest. So look, yeah, I'm beginning, I was our VP of sales, where I was the first sales rep, closed our first 10 million AR. And as we grew, I knew that wasn't my passion, and I was doing it because I was the only one of the original four who could talk on the phone and handle sales and I had sales experience. But I had always had a love for social media, for marketing. And I think that's one of the reasons why I've also stayed, because who else would let me try this crazy stuff? I've got actors torquing, you know, on videos, right? Like what other company can I go to, they let me do that? Now, maybe since I've proven it, yes, but like only a click up could I try and have this free reign. And so that's another reason why I'm still here. Okay, so we're going to talk about B2B social today. The goal is to leave you with some ideas, just waste the thing about things, get you on stock, give you some inspiration, that would be a successful episode here. So first, can you explain, you have this way of writing, and you've written it before, I can't perfectly articulate. So I'm going to ask you as a question, but how do you articulate the value of B2B social? And what's the mistake that most companies are making when it comes to thinking about social as part of the marketing strategy? The first mistake is so easy. It's that they're treating social media as a place to give more ads, right? And when people pull out their phone, they don't want an ad. They don't want to be sold to. They want to laugh and they want to feel something, right? They either want to learn, they want to add some value added to them or they want to laugh. That's really odd is, or feel some type of emotion, right? They have some people who might watch prank videos, some people who might watch videos to learn more about cloud and get better at that. And you have some who just want to make fun of the business world, right? And that's what I attack. So number one, the problem is just talking about your product. That's what 99% of people do, and it's the wrong thing. The second is they don't give anything enough time, right? Like they don't understand that it might take six months to see if something's working and marketing. And the problem is that's why CMOs are, you know, that's why they should be an exit five and things like that. They are the most let go or the most attacked in my opinion at a company because they don't get as much time to let something win. But for anything and marketing to win, you have to give it time and sometimes it's hard to prove. And that's the challenge we face every single day as marketers. Okay, so the big thing that's shifted in our personal lives is that the majority of the shopping, buying, consuming that we do is now not only through our phones, but through some form of entertainment, whether it's Instagram, YouTube, podcasts, TikTok, Netflix. I mean, I'm watching something on the couch the other day with my kids on Disney+ and there's like a Salesforce ad, you know, like CTV. Small to stuff is everywhere now. What I hear you say is like, we want to build a strat, we want to have an actual point of view on how to be successful on social media, not just treat it as another like distribution channel. Like, oh, we got a blog post, so post it about it on LinkedIn or like we won this award, so post it about it on LinkedIn. Can you explain the, like if we peel everything away, where did someone start? If I'm listening to this, you're gonna give us some good examples of stuff. But how do I peel this all the way back and figure out like, it's almost like you need an angle, like what's our angle for social going to be and do you pick an angle, do you pick the channel? Where do we start? You got it. First off, you got to follow the rule of three, right? So like what I do now is I will say no, I still get those requests. Okay, we have an event here, we need to post that. Well, I'm like, well, one percent of our audience is gonna care about that, right? So if it doesn't do one of the, one of the three, right? So it doesn't make them feel something. If it doesn't add value and doesn't teach, I'm not hitting post, right? And there's another rule that I have. So before we post, if it, I need to ask what the hook is, I need to ask why would someone even watch this? Like why would they care? And I need to follow the pacing, right? Is the pacing there? Like is it quick and is there a payoff? Is there a reason to watch the end? So these are the quick little rules I have. I make sure before even create a post. But now let's take a step back before you even do that. I think the thing is the big, the big thing that you will study is say, hey, be on me, present. And I do believe that. You should be posting on every platform, but I don't believe you should be creating for every platform. So for us, I click up, I'm creating for two platforms. And one is, you know, it can be TikTok or Instagram or else they're kind of the same to me, with short form. And a second is LinkedIn, right? So I'm creating for those two. And all I'm doing is I'm creating funny, I lean into business humor. So I'm creating funny business humor. and then I'll link to that I'm writing about the thought leadership. And that's the two things. That's it.
it. And then what I'll do is my Instagram Reels, I put on trial Reels first. One of the biggest gifts I can give you, Dave, if someone does care about short forms, you need to be using Instagram trial Reels. Why? Because think about it. We'll say I have one video and I do three different edits that takes my editor, maybe an extra four minutes max. Right now have a different text on screen like this. It's where most people read. Now I have a different hook, a different thing to catch with the beginning and maybe have a different format. Right. And when I test those in trial Reels, I get I don't get punished. It doesn't go to my followers. One video will do better than the others. And sometimes they'll do significantly better. So much so that I have a video that would have only gotten 60K if I posted one. I thought was better. And it goes to like 10 or 20 million. It's a major difference. So even if you have a great idea that you love and this video is I love it. Press put it. It's like a standard operating procedure to have three variations of it. Every single time no matter what and you be shocked how many times you the one you think is the best is not the best. Yeah. No matter what, no matter what you should always be. Maybe it's like everything I'm marketing. Why wouldn't you maybe test if you can't and you can't today in social media. And does it is it does even matter even if I'm I've a like our ex-ifive company account. I don't know. We have like maybe a thousand followers. Is that enough? Should I still run trial Reels? Still worth the time. Still worth every single time. And it's so easy. I'll show you I'll send you my playable capture on how to do it. Your team can implement it in no time. Cool. Everyone thinks a click up has this big social media team. It's me some actors that are higher and they're just but they're not in you know and then it's a social media manager. That's it. And my social media manager just knows how to run the trial Reels really well. So the for every listen. So I like the reason for having Chris on was I think this is probably the the thing that I see the most is and I'm guilty of this time and time again where like don't really have a lane, but I'm kind of posting content of all different types and all different kinds. And I got it on YouTube and I got it on LinkedIn and everything's kind of doing okay. I think it's probably the fact that you honed in on like we're only going to be on these two channels. So so you know let's use TikTok and Instagram interchangeably and then LinkedIn. And you're not just like making random videos. You're making random videos that all serve this purpose of like it's in this category of funny business humor. And what I want to make sure you also know is that I'm posting on 35 accounts every day and that right. So it's not just click. I have click up on all the platforms right then I click up comedy. I've click up on the street. And so click up is more my product. That's where I'm helping people. That's where I'm making that's where I'm doing more like teaching. Click up or here's three tips to be more productive, etc. Yeah. And I have my click of comedy because the comedy I used to do both and I realized that some people want to watch the comedy. So I want to watch click up personal. So I've made these different pages. But yes. So I'm leaning into the business humor. But when I tell you the money creating for two platforms, I'm still posting across all of them. So when I make the one video for TikTok. Sure. But you must have gotten it. You probably didn't have all those pages out of the gate. I'm betting that you had your posting funny things that kind of popped off on the main click up channel. And you're like, oh, we could carve this out and do its own page. And I realized the audience was getting confused and was limiting how far I could grow. So funny enough, click up comedy. Click up has been around for years before click up comedy. Click up comedy is more followers than click up, right? Yeah. But that's just because people love comedy the most. It's a bigger ceiling. And it's also kind of like that could be anything that could be a comedian. Like, click up. It doesn't go to your head. That's that some type of software that someone's going to try to sell me. You know, it's like if you were exactly like if it was like Salesforce comedy, it kind of hits differently. So it is, but you know what it's funny because there's definitely some people who follow that page and don't know what we do, but that's fine because we're running AI to see who's following who and if I like, I found out that the CEO of McDonald's, the CEO of McDonald's follows click up comedy. Right? What do you think I did? Of course, I got my actress to make a video DM him from the page and set up a call because now now I've turned this into a sales motion. And mind you that for anyone out here is doubting and thinking, oh, there's no way you can leave. Did he respond to that message? He did not yet. He did not, but but I'll tell you who we have gotten from this. I'll tell you as Vayner Media are our fourth, one of our larger deals from last year. I think it's top top seven or something. They said they found this solely Gary and then teams saw our social media as a give them a shot. And that's how we got a chance to win and that's and we did win the business eventually. They're one of their definitely large customers now. So we do close big deals off this. Let's come back to this when we talk about measurement because that's the interesting play to run that basically treats social as a signal as opposed to like we're way you know, there's there's something interesting there. Let's show I remember that for our measurement piece. How much do you think like I feel like somebody's going to listen to this and they're like, yeah, well, that's easy for them. Like humor, like obviously marketing humor, but like I could never do that in in my space. They do tell me that all the time. And my answer back is you don't have to. I'm not telling you have to do humor, but I'm telling you have to do something different than just saying, hey, drink this water bottle or whatever brand you have. Like the more you're just saying, or hey, try out, click up today that they don't care about that. Right. So if you're not going to do that, then then it goes back to the other rules. Then can you teach them something? Right. So can you be can you be the news for your network? Can for your people? So it's a your an AI company can be the first to give a roundup every day for AI? Can you do a really good job of that? Or can you make them better at their job? For me, it's project managers, right? So if I can make them better at their job, that is something that's also valuable. But you can do comedy. What is what I also strike back? You can't do comedy. There is something funny and no matter what space you're in. If it's you put me, you today you dropped me in a new space guarantee I can make funny content for doctors guarantee I can make funny content for lawyers. You know why Dave? Because my formula is this. I really know my ICP. Well, we're doing right now. I do this two to three times a week with my ICP. I asked for a 15 minute Riverside. I record it and the first seven minutes. I'm selfish. Hey, what podcast you watch? What's funny to you? What's something ridiculously hilarious? It happened to you recently, right? I'm interviewing real people. How do you get those meetings? I live in just cold LinkedIn, cold LinkedIn. I'm hitting them up. But do you see someone who's a customer or just an ICP like this person looks like an ICP? It's a mix. So I have my customer team help me out and they'll say calls my customers. They give me about one or two of those a week and I do about one or two myself where I just see someone linked in. They don't have to be a customer. They can become a customer later. But it's see someone linked in is like a project manager, maybe even like a marketer or whatever. I'm like, hey, look, can I be selfish and just ask you for like a 10 minute Riverside? I'll give you clips afterwards. The first five minutes is for me. I'm going to ask you some questions. I just want to know I won't do anything with it. The other five is for you. I'll highlight your brand. I'll send you a video chopped up ready to go. So you actually record and give them something to use from that? I give them a gift every time. So I give them a gift for joining and give me that. But that's how I really know my ICP. That's how I have ideas. Go think about it. I would run out of ideas in a writer's room if I was just trying to write this all the time. Yeah. I'm asking real people is something funny and happened in the office last week or totally. Dude, I feel like I am the best at my job when I'm talking to the most amount of people. That's when I'm sharpest. And so either I'm on lots of calls. I'm hosting webinars because even something like on a webinar, if I say something or a guest says something, you can tell right away in the chat that everybody kind of like that line landed. They felt it. And so it's like, oh, that's a little, that's a thing. It's like a bit. And so it's like, let's circle that. And like, man, when so and so said in the chat that AI is like, you know, smarter child back in when we all had AOL and semester, oh, everybody loved it. Let's make a meme out of that. That's where the ideas come from, right? There you go. Well, I feel like selfish when I first started learning about you. I was like, that's why he started eggs. If I have to because now he gets to talk to all the, he just talked to his, his ICP all the time, like how genius is that? Yeah. I'm a genius. I'm a super genius. Quick clip that. I'm a little jealous. I need to figure it out myself. No, it's, it is one of the things though that it's kind of cool because it's, I didn't want to go and build an agency or consulting business. I had done that for a little bit. And after having done this for a while, I was like, Oh, no, this, this can be the whole thing. And actually the, the reason I have like a hard day and as a CEO to run the businesses because I think the most value that I can provide to our businesses, talking to people, doing interviews, having an understanding of like what topics are relevant right now? And I, the meta lesson is like, that's actually a secret ingredient for marketing. And so if I was leading marketing at a, you know, company in the AI or cyber security or Fintech or HR, it would be put Chris puts you anywhere. And you could figure it out. It comes back to that deep understanding of the ICP. And that's what the fun job of marketing is. Okay, I'm just trying to sell. I'm trying to get these people to pay attention to this thing. How do I do that? Your bridge is going to be social short form. Okay. How do you connect that? How do you, how do you connect that to actual impact? Like how do you people laughing about work humor? How does that show up in the pipeline and revenue chart for click up? Yeah, absolutely, man. I mean, and trust me, that's a question I got very early on very quickly. And it took time to show like everything good. And the way this, it's not like I started this plan with these actors and it got tons of views, right? I started very scrappy at the beginning. I was the other actor and I hired one, one actor for like three K a month to start creating videos, right? Where did you find them? I had to just saw him as guy for a couple of years. He was at, uh, he was running TikTok for ad world. And his name is Luke and Luke had done an amazing job for them. Grew them to 300 K. And I kept telling him every day if something ever happened there, you let me know. And he called me and I'm like, hey, look, my company hasn't fully believed in hiring a creator full time yet. I promise you, if you dive in this with me, I'll get you, I'll get you a full time gig here. And so I did. Do you think that's kind of the secret? You what you interested, what you mentioned is kind of like the secret sauce. I see people like this all the time. Like, hey, who should I, anyway, know any good, anyone good to hire where I feel like the best people often it's like you were like ad world, like I don't, I don't follow ad world, but you do you and you so ad world must have come across your feet at some point. You're like, damn, whoever's doing these videos for ad world is good. Mental note of them. Then when it comes time to hire, you're going to reach out to that person. There's so many people that are good at what you're describing. I'm like spitting this back for our listeners. Like, yeah, this is the skill. It's you have to know, you have to be curious. You have to know what good content looks like. You have to have a list of like 10 accounts that you follow that you can reference as good examples. It's not like no one's going to give you a list of those things, right? Like never. And now we're talking because I designed my feed to be this way. My feed, I have found so many creators who are big now. I found them early. And you can go look and a lot of them have been in a click on video before they blew up because I find them. I've trained my feed to find like up and coming comedy business comedy. That's what I do. So yeah, I saw Luke state and I found a way to get in touch. I'm also relentless. I'll get in touch. Everyone knows it's a click. I'll get in touch with anybody. There's been a how big off. I'll get in touch with them. Do my network because I'm at every event. I'm speaking all the time, right? Like I'll
I networked like crazy. So if I want to get in touch with someone, there's always a way. So I found someone who knew Luke, they plugged me in and I stayed in touch. I said, look, if anything happens there, you tell me immediately. And one day I think they let him go. And the next day he was working for ClickUp. So I got him as a contractor and I was like, I promise you, you do well. I'll get you this full-time thing. And I did. And it took us three months to start getting any significant views. And then we got the views. But now to answer your question about pipeline, this is the biggest question. This is the one I get asked all the time. Does this work? Do you get pipeline? Yes. And if I'm being honest, tracking it is not the easiest thing in the world. I'm sure there's even more deals. But there's two ways, two early signals I saw. Number one, RHR team just said that every time there's a viral video, the amount of inbound applications we had was just out the roof, right? And insane with sales. My sales team tells me that they start now asking after they close the deal, how'd you first find that? So in a lot of times they will say social media is becoming far and far and far bigger than we ever imagined. We love your videos. We love your videos. We think it's hilarious. So the reason why I think I keep winning, Dave is people are probably too afraid to go do a strategy like this because I don't think I could attribute anything the first four to five months. It was very hard. And you don't think my COO Gourub who's a genius. You don't think Zeb who's an absolute genius was not on me about that to prove this. Like luckily I wasn't spending a lot. I was smart. The time was only spending like seven, eight, K a month. So what do they care? You know, that's fine. We could spend that. Take a little bit out of the ads, right? And and our cat payback was going down because we're using these actors in our ads. So we're using these familiar faces that you already see. So they were already happy about that. But then all of a sudden when one major deal, we had a major deal somewhere ever sees like from Australia or something. And I never forget Lightfoot. The rep was like, yeah, they said they found us from the videos. And they were like, okay, we're on to something. Then Vayner Media. The rep is called Lightfoot. Shout out to Lightfoot. Yeah. Jonathan Lightfoot is his name. He's great, great, incredible sales guy. I think he won so many awards at SKR this year. But he was just telling me that was one of those the first signal I saw. They're so excited. And now I get it all the time. The reps are pinging me all the time. Yeah. Hey, they love the HR guys. I mean, people ask them to bring them out. Sure. And there's different characters of people know. Well, now that you know, there's like a tipping point. It's like everybody's searching for attribution with social until you hit hit on something and then and then you know. And then a lot of the times the attribution, it's never directly to I think one of the challenges is and I've learned this through through our type of businesses. And we've done a lot of like, you know, influencer type sponsorship type of content. And it's almost like this trick where like you have to try to less you make it more like direct response marketing, the better it actually does. And so if it was an ad for click up, it might not be as good if it was a funny ad for click up. You know what I mean? Like it's just like every single time that's the heart. That's what makes this game so ridiculous because I think it's like everything good in life. Right. Everything good in life is on a little bit of risk and on a little bit of doing our CEO says it's the best. But like even when you're building products, if you're building what everyone else is building, you're probably not going to win, right? But you got to go or someone else is not playing. It's like you can you can sprinkle in like you can when you have something interesting from a click up product news announcement standpoint, you can make a great video about that. Now people already know who you are. And so you're going to it doesn't have to just be pure ha ha comedy silly silly like there's a lot of overlap. I think the other thing the reason I love this topic for B2B is because we know we are always searching for the thing that's going to do it this month, this quarter. But I had the Wang VP from LinkedIn on a couple of weeks ago and he said the average B2B buying cycle now is you know whatever 211 days. Sure. So our goal then is like how do we get people to see as many of these fun, interesting, educational, whether it's new, whether you want to you know you said feel something add value or teach. You got it. How do we get them to do that as much as possible over a couple hundred days and then the deals will come. And to your point, people are just going to raise their hand and say social media. I can say, Oh, it was this video on you know January 7th, but you feel like you know that social is working. And then obviously you have your results and views and you can sort you can go through engagements and kind of like pick out the little pockets of things that we're working and go do more of it. How much did the volume of what you're creating? So you hired this guy, you know, spending seven a K a month, it's it's you and him. You're making videos where you're making like one video a week or you making 30 and it's like scientific and you're testing all these different hooks and headlines. How did it? How did you? How do you really become a lead at the creation here? Because me, I got this dumb little Instagram page I make for myself, my fund, my own videos and I just like, you running yourself? No, not for real. Just like Dave Gerhard like on Instagram, like me doing like pull ups or something, right? And it's like I make one real a week and I get a couple hundred views. And I'm like, man, like the real thing in this game is you just need so many at bats. And I'm curious if that is true. I'll tell you this. I have the popular thing, but also if something's not, it is not reps, but there's also there's a limit to it. So I'll tell you this. I'll tell you you to do the whole thing real fast. We started with the first three months, which is me and Luke, right? And and we were not doing the whole testing. We were just doing like a video a day, maybe five to six a week, right? That was it. We would shoot, we shoot for a week, we shoot one day and we'd have enough for like maybe one to two weeks. And then we'd shoot again. I had to fly out, you know, staying in San Diego a lot of times. I live in Florida. But so then we started getting reps. And so then so we got to like 30 million impressions in a month. And I remember we had someone before me who told me they're like 20 was impossible. And I was like, no, I can hit it. And so we hit, we hit like 30. And then our COO was very like this. And so this is the click up way. Okay, you hit 30. Now how do you get to 100, right? I mean, I can get to 100, but I need another actor. Like I need one more actor. I need to make this even more serious. So that is when we brought in Adam. Adam is a second guy. You see the guy with no hair. They're like almost like the step brothers. You know, they're very funny. They played well together. So then we bring him in and then we start, you know, really creating more videos. And then we start testing. So now we have a whole formula, Dave. It looks like this on Mondays. We have a writer's room. And in the writers room, we come prepared with like three ideas of peace. It's me, my actors, a couple other workers employees. It's sometimes a higher writer to freshen things up and bring someone new in. I have Jimmy Kimmel's writer. A few other writers come in and they're actually not as expensive as you think they come in for writers room, brings my ideas. Okay. Then on Tuesday, oh, sorry, on Monday, we all pitched the ideas and then we vote. So we all pitch and we vote. No ego. We vote. It's done. Okay. Those are the ones that one if someone really feels good about something they can bring up their idea again. But that's it. Tuesdays. We find tuna. We find tuna scripts. Perfect. Them who's going to play what character order all the stuff Wednesday. We check in. Make sure it's good. Thursday. We shoot and we usually get about 12 to 15 videos. And then then Fridays is when I'm analyzing all the content. So I'm looking at the content we post the week before and it's just a flywheel. Now we just keep going. So we keep running that every single week. But now that got us to a hundred million impressions. And then really to 200 million. But what Guar have said was he's like, okay, now if you post twice a day, then you should get 300 million impressions, right? It actually didn't work that way. We learned that there is a limit. There is a point where it's too much. And people didn't want to see that much. Click up comment. They wanted like one video a day. That's what they wanted. They wanted to laugh one of our videos because our numbers actually went down as we did double. They went down noticeably. And we tried it for a couple of months. So my thing is there is a sweet spot. And for videos like we're making, I think people like like one, I think one a day is a nice number. So we keep it to one a day. Now every now and again, we'll still post a second. And there are some people who say definitely like if it's a personal account, you might want to post eight and nine times a day. Get more reps and something hits where you have more chances. So do you have a target for how many how many you're trying to publish in a week now based on this? Yeah. So for my click up comedy account, it's seven. For my click up brand account, I usually go for 10. I still post twice a day on that one. I think it still works. And then for man on the street, four, five, the click up memes means is like one or two a day. Memes you can go as more if you want. I just I don't think memes actually memes are one of those things that you can get attention from and they're smart to add your social media strategy, but they don't drive sign ups in my opinion. Unless you really become their meme dealer. Yeah, people probably don't visit the page a lot, right? A bunch of follow ups on this. So the process of recording, how did you like where are you now and where did it come from? Was it just like you guys recording remotely on your phones? Now you have real actors. Are they filming in person? People ask a bunch of questions about that. So give me the high level on like the writers room breaks. You said Thursday you film. What does that actually look like? Hey, it's me Dave. Our friends over at customer IO are sponsors of today's episode. They're a really cool company that helps marketers turn first party data into engaging customer experiences across email SMS and push and they built their platform for marketers who actually care about the craft because marketing is a craft that takes creativity, thought and taste right now. Everyone thinks they're magically a marketer because they have access to AI and the result is kind of painful. More robotic emails, more noise, more bleh. AI isn't magic. It's not going to fix bad strategy or write great copy for you magically, but the best teams also aren't ignoring it. They treat AI as infrastructure when it's built the right way it actually makes marketing feel more human, not less. And that's what customer IO is doing. Their AI handles repetitive work like setup, orchestration and tasks that should be automated so that you can focus on what actually matters. The craft of marketing, the strategy, the creativity. This is how good marketers are using AI right now, not to replace thinking but to support it. If this landed with you at all, this idea about the craft of marketing, I want you to go and check out customer IO. It's customer.io/exit5. Go and check them out customer.io/exit5. Hey, it's Dave. Look, I want to tell you about Drive 2026. This is our annual event we do for the exit5 community. It's a two day BDB marketing conference in Stowe, Vermont. We built it for marketers who want to get smarter and actually connect with their peers. This isn't a generic industry conference. It's a small, intentionally designed event where the programming, the venue and the schedule all work together to create the conditions for real conversations. Attendee spend two days getting into the tactical details of BDB marketing. What's working? What's not and how the best teams are thinking about the problems that actually matter. This is all about workshop sessions and discussions that are built around participation, not passive. Listening, I want you to come and be there if you're going to take the time to leave your family, leave the office, get outside of work, like actually be here, take notes, pay attention, and make it all worth it. And here's the thing though, the BDB marketing stuff, that's what's going to get you to justify the ROI on your ticket. That's why you're going to be able to tell your boss that you want to go to this. But the best moments at Drive don't happen on stage. They happen at breakfast on an afternoon hike over a drink.
After dinner, right? Somebody's gonna be roasting marshmallows at this place. It's that type of event. We designed this for, for this connection. This is on purpose. Long breaks, unhurried meals, and opt-in activities where people spend time together outside this session room because look, we're all people. Where else in your life can you talk to someone else who understands your job as a B2B marketer? I go to my kids swim lessons. I can't sit there and talk to that next to me about B2B marketing, but you can through the Exit Five community. And that's what drive is all about. It's September 8th through 10th, 2026, at the lodge, it's Bruce Peak and Stovermont. Check it out, exitfive.com/drive to learn more about it. It's exitfive.com/drive, and I hope to see you there. - Yeah, so in the early days, just so you understand, like if you're just starting, all it was was me, my actor, we've had some ideas, we shot, and like maybe I would hold the camera for one, he'd hold another, and it was just us. We had no camera person, just iPhone straight up. Yeah, now today, funny enough, we still shoot with an iPhone. For the most part, every now and again, we're doing a music video or something higher end. We will use a DLSR. But for the most part, still iPhone still wins. And I'll tell you something really works well is when you make it look almost like it's Snapchat or something, so it just looks like something just started. Those do so well. - Oh, yeah. And this is you guys doing this in the office or something or where. So we shoot two different locations. So our office is in San Diego. Most of our actors are in LA or in Orange County. So we now have a studio that we rent, that we've kind of share rent in Orange County. And so most of the shoots are in Orange County. Every now and again, we'll use a click up office. It's very nice, aren't you in Miami or something like that? - I'm in Miami, I'm not at every shoot anymore. I got unflying tonight. So look, just to give you a wide range, we're doing a hackathon right now. So Zeb, our CEO is just hilarious. And while Zeb has flown out our nine or 10 best engineers are staying at his house and they're working all week. So I'm flying out there to get content of this, to get more like this YouTube, like behind the scenes field, how click ups becoming an AI company. So that's like one type of content. But I am not at every shoot anymore. I don't need to be this machine runs so well, I am helping write the ideas. I know what's gonna be shot, but the team is so pro, the day show up and they shoot and they handle it. - Got it. So we've scaled from Chris doing this to now, there's a team that you manage and run that's doing this. - I'm still at like every three shoots or so. I fly back every now and again, but taxes are pretty good in Florida. And you know, click is getting pretty big. So I want to make sure I'm preparing myself. - So I'm in Florida. - All right. - And I like it here. But yeah, so I fly in and I still have, I'm still heavily influenced on, you know, the ups of the day, but they can run it. They once made the scripts and they're pros. - But they're filming and they're shooting with like specific ideas in mind. You get all that footage back. When do you get it from filming on Thursday? Like when does that stuff is that gonna be in the rotation for Monday or is there a longer time window? - Yeah, we're so far ahead now. If I'm being on a day, like I probably have 80 videos in the bank. Like we cannot shoot for a while. That'd be fine, that's because we keep, we get more than we need to post. So basically like that's the whole game. And anytime I've run until like a slow down with like this podcast or content in general, it's almost like if I just stick to recording two episodes a week for me, it's two episodes a week that I can just always go. And then the worst feeling as a content creator is when you have nothing and you're like, but my issue would be sitting on the 80 because I'm very much like a next, the next idea is the exciting one. And so there's like how do you not forget about the 80? Like tell me if you, also tell me if you go and you shoot. And there's like one that's just like a banger. Tell me you're not gonna prioritize that when like I'm gonna ship it the next week. You just took my next few lines. So there were some of the always happens I feel like. We're like two, well, some there's also two there timely, right? Like maybe like, you know, like maybe like something phenomenal might happen like the the cold play concert, right? If you want to make a video happening on that, then we didn't do that. We chose not to down, but I'm just gonna example. If there's something big and timely, we'll put out immediately, but if there's something as a banger, we're prioritizing that. And then the others might just wait for two weeks. I'm like, oh, remember this one. So we, we had a bank and we know where they're at and we sit on Fridays and typically go through them. Okay, what's in the bank? We need to get back out. All right, so that's that answered that one question. The other thing is like, how do you host to all these channels? Are you manually doing that? Are there tools to do that? How do you both kind of analyze all this stuff? Are you going to each video and running it down by hand? Tell me the tell me that side of the process. Yeah, I actually so funny. I've tried almost every tool you can name. And I've, you know, sprout social dash shots and I've kind of never liked them all. Never had a good time. They were pretty expensive, right? I actually I use VISTA social now. I don't mind showing them out great. Vitali and the team and Reggie, they're incredible. VISTA social is probably one of the lower cost ones and has everything. So in there, we use ClickUp obviously to manage what's going on. So I can see and I can prioritize. And then from there everything goes to VISTA social. We'll put that stuff on Instagram, TikTok, all the places you needed to go. We post via VISTA and it also tracks everything. And is it a myth factor fiction that using a scheduler impacts reach? You know, look, I think it's a myth. There's sometimes I still like, I've been kind of one of those weird people who still the majority of times we still a lot. We'll post manually a lot. Even through VISTA, we'll still post manually. But there's times where our social media person's traveling and we schedule when it's been just fine. So I'm starting to lean into some myth. But if you asked me six months ago, I would say, I still post manually. But now I think it's getting better, especially they have native integrations in. So I do too. I believe in both sides of it. But I think it's like anything in life. It's like sometimes you have to do it because it's not realistic to always be posting native. Yeah. I think you have to. And now I've seen no problems. I think I think a couple of years ago they did. You still do it. There's pressure and they don't anymore. OK. And then what about looking at success? There's probably top of the funnel stuff that you look at. You're doing that manually or that's coming through the tool also. That's coming through the tool. So we analyze it. So VISTA will give us weekly reports. So we'll look at it. So every Friday I'll come in and I'm like, OK, what platform we get. And it's funny. It's funny. It changes. If you'd asked me six, seven months ago, I would say six, seven. I would say TikTok was our number one. And then now it's shift. And now Instagram has been our number one. But now Facebook. Do not sleep on Facebook Reels. Make sure you're posting your podcasts to Facebook Reels. We are getting insane. Oh God. I can't, Chris. I can't. I'm not. No. I can't go to school. I'll show you how to do it. OK. If you could just press the button. Facebook Reels is actually popping. If I showed you our numbers, you would change your mind. I think 100 million of our views came from Facebook. Last month, 100 million. So if I was a user Facebook, I'd have to numbers. So that is someone seeing your page and their feed. If they're not using Instagram, but they're seeing the Reels from the Facebook app. Facebook Reels. You don't think that's a pretty good audience on Facebook. It's like that, you know, 38 to 60 that are on there. So they're usually decision makers. 38. This guy just put me in a box. I'm 38 on the number. I'm right behind you, but I've done. I'm coming up. I'm right. Look, I'm the one that had that hair surgery. OK. No, I think there's something to that about testing all the different, you know, being on all the different platforms. That's why I think your approach is like they can all be, you know, Instagram and TikTok can be used kind of interchangeably. Oh, obviously Facebook Reels and that same bucket. It's this first and YouTube shorts and YouTube shorts, but it's this approach of like the skit and the content first. Then we're going to cut it up for those specific mediums, you know, exactly. Let's see. What else did I have here about this, this process? Obviously, the team gets it now, but if you're someone listening to this and you wanted to go start this approach, where would you start? And then, ah, here's my question. Where would you start? I want to know where would you start? Hit me. And then what about Chris? I don't want to be. I don't want to be the guy on camera, though. And so like that's kind of a blocker for me. I kind of want to do that. Sure. The thing I tell everyone to do first, do what I said earlier, understand your ICP because you go create content. If you're creating the wrong, if you don't know your ICP or never going to what they like, you never know what they want, you never going to think it's funny, all that. So I think you do 20 or 30 of these calls, I said. And then you take some data and you say, okay, it looks like 15 of these people and they said they pull out their phone. They like to laugh. Maybe this is what I maybe Chris Cunningham was right now, do you need to make that content? Now you want to get started. Guess what? I'm not great on camera either. I still try at the beginning. I'm not an actor. I'm not like this funny. I mean, I'm funny, but I'm not like actor funny. So what I recommend is you go find a creator. I recommend you go get on social media and I recommend you start swiping. And eventually you're going to see a couple people that do not have many followers, but have had a hit. This is what I always look for. Someone has 3,000, 4,000, 8,000 followers, but they have one big. Yeah, they got that one pin, one pin real with like 1.2 million. You're like, but they got, you know, 6,000 followers or something. There you go. Gold. I'm excited because they're making $0. They want any brand. They're waiting for a brand to hit them up, but they got talent because I'll tell you this. If you can hit once or twice, usually look for more than one hit, maybe two or three. Also, think about that person. That person is most likely actually definitely this. This is not their full time job making videos on Instagram, but they probably want it to like it and they're good at it. And they work at a, you know, they're, they work in accounting and they want to look for a different job. Just to be able to, it doesn't even matter if like the click up thing is like, dude, this is a soft, some like billion dollar software company. Like, is it going to pay me a thousand bucks a month to like make them six videos? Like, that's a, that's a great deal, right? I couldn't tell you how many people I found first. I'm not like, have you seen the page corporate dudes? Corporate dudes I found when they had like three or four thousand followers. Now they're massive. I think ramp blew them out to some world. But this is great. This is, this is the takeaway. It's like, you didn't, Chris, it's not like you hired some agency to find the creators here. You're going through these and you're like, I'm just going to DM all these people and see who I can get. And that's why I create content myself because when they see me reaching out, they're like, okay, he's trying to create too. Like, I understand this guy, right? Like they see me trying. Yeah. And I'm cool. You know, I hit him up not like on some like, hi, like professional. I was like, yo, what up? Your videos are great. I like, like, I like this one was funny. This made me laugh. I think you have some talent. Right. I run marketing at a software company. Like, could you, you know, would you be interested in doing something together? Would you be interested? Look, I can't pay you a ton. I can get you more if you start getting, I can give you goals and I can, if you hit these goals, I can pay you more, right? Because I can go to my CEO. Does that creator have to be the face then forever? Like, is it, you know, could you have a bunch of different faces? There's, there's this whole thing like, you look at someone like Ross, Palmerance, like corporate bro, like he is the corporate bro, right? But then you could have corporate dudes where you have multiple, multiple people. Then you have click up and I would want it to be not relying on one person.
but to just kind of always be funny business content. Is that possible or is that a pipe dream? - It's very possible. Look, I have a new actor now then. Some of you know, he's a guy wrapping and doing some of the new stuff. He's become a big actor in the three. And I also have other actors that I pull. So I'm always finding a new talent. I'm always sometimes flying other talent out from New York. I'm finding new people in LA 'cause LA is where I get most of my talent. I believe you can have more. I think once you get the ethos and once you understand what you're doing, right? It's all about the scripting. So if you're scripting really well, what is your budget for this? How do you have LA studios this and that? Like yeah, studios probably 2K a month. There's other people running it. We just run it for one day a week. So studios 2K a month, you know, I have my actors that I pay full time. They're big, great. But nothing, you know, those are full time, click up employees. - I've hired them full time. Both of them. They have full time salaries, insurance, and they're investing equity right now. I'll tell you why, because they were about to get stolen. Everyone wanted to hire them. All my competitors hit them up. If I didn't, no shot. - So can they not make videos for other people? Is it like part of the deal of being a creator with you guys? - I stay pretty chill about it. Like if they're doing, as long as they can't go to a time. Well, they want to take a video. It's not a competitor here and there. I want them to, I want the actors to get extra money. I'm not one of those. You know, I could, I probably could, it's in the, in the two people that are full time, they were contract like doing side work for a while. - Yeah, they were doing side work. The other guy, Adam, was even, he was just like, he had a bunch of odd jobs. I think he was a stuntman before, before this most recently. - Okay. - So funny, funny things. - All right, so be curious. Find an angle that isn't just promoting your own stuff. Feel something as value, teach. Be curious, find these people yourself. You don't have to be in the videos, like hustle to find creators. I would love, if somebody's, listen, I would love to prove like the humor works, but also I feel like this thing for me, you said, feel something at value or teach. Like, doesn't have to be business humor. I think you could win by creating, like I liked your example of like a new show or some type of industry news related to your industry. And that's what's cool about us being in B2B. I know so many people from exit five that like, I love them people say B2B is boring, because actually the most interesting companies that I know are people that work at B2B companies. There's like, you know, defense contracting, cybersecurity, martec, manufacturing. This company makes the infrastructure that supports X, Y, and Z, and like, these are amazing examples. Like, there's gotta be, you can't tell me there's not a creative angle for social media for those companies. - You drop me in any one of those, I'll do it again. 'Cause now under the formula, there's always something, right? It's just finding nuances. Like in any of those businesses, I guarantee you're some funny that all those people who are their ICP, they laugh at, right? But you just gotta be inside. You gotta really hang with these people to know. - Okay, what, how do you feel about AI in this world as a marketer, social media person, creator? - I think I don't have the perspective that everyone is so cool to say. Like I'd love to say, hey, run all your content with AI. I'm not that guy. I don't, we don't use AI for any scripts. We don't use real human actors, but I'm not gonna sit here and lie like I'm not paying attention to it. I definitely create AI videos. Like you've probably seen a LinkedIn, we've had a few AI videos go viral, right? I'm still playing in the game. So I found a guy named Jim Friend, who I work with, and he's created some AI videos for us, but I've done like half AI half human. So like for, I'll give you example, for Christmas, we interviewed Santa Claus, right? Santa Claus was AI. We had a real person interviewing him, and we made it feel like kind of like a diary of a CEO podcast. It was like dramatic and done it. So like we still play around with AI. I even have an AI meme page that I run. It's like, I forget that it's like, click up something. It's like a meme page is only AI. - Yeah, but why? What is it about? I can hear it in your voice. It's like, there's a specific philosophy to like why creating your own humor and writing your own scripts matters. Why? - It's easy for me. I don't think humans yet enjoy AI. Content more than content for other humans. I don't enjoy them. I see an AI video, I know it's AI scroll. A quick scroll is not real. And I think that's why I see a ship is happening right now in social media where if you even notice, people are just getting better views, picking up their phone and just recording now, because people are craving real. There's so much over-pollucions. - I saw like, Chimath had posted this on Twitter. He had crushed for it rightfully so, but like how Instagram just needs the right AI image model. And everyone's like, no, you're missing the whole point. The reason Instagram I think is having a surge is because, because everything is AI, I love the raw. It almost feels like the Instagram stuff that's working right now feels like fine type of stuff. It's like silly 10 second, like some guy. - Wow, real. - I'm watching this guy. You ever seen this guy? He eats like an onion on a plane or a lot. A lemon on a plate. - Of course. - This is real, because AI can't replicate it. And right now the scripts aren't good. I can tell when you say AI to write, just so you can, interestingly, hear you articulate that, because I'm super bullish on like AI as a technology to help me like run my workflow and do my life better for sure. But what you're talking about is the same reason why, I spent all my time working remotely, talking to people on screens. This does not feel, I can feel how I feel. Even like if you and me were hanging out in person right now, the vibe would be instantly like, we'd want to go hang out, get lunch after this, like type of thing, right? - And we will at some point. - But yeah. - Online is just like, "I'm gonna hang up this call and I'm gonna like, you know, continue on with my day." It's not the same as like when a couple weeks ago, we had a bunch of our neighbors and their kids over and just I left feeling like, man, there's something here where like literally how we are wired as what are these creatures as humans. We need to be around real people. So there must be something in our brains that goes off. I was like, "Eh, this is kind of like a fake thing. I'm not into that. I feel, I really believe that." This might be the best way I've articulated. I've heard it articulated is because I think, so I think people like, they want to be connected to real, they don't want to be sitting there watching a bunch of AI videos, right? They don't want, that's why, like I've seen some people make some AI YouTube series, they get some views and stuff, but then the day like most people want human connection, they do, they love it and they missed it during COVID and that's why events surged after COVID, right? Like, and that's why events are doing so well now 'cause people wanna be around people. - So during these, I keep, I put some notes in our Slack and I'm just like making bullets of interesting stuff as they come up and I just said, I can't wait until Dan hears this one. I apologize in my advance for all of our notes about our social media strategy. - Oh, yes, sorry about that. I'm happy to talk to the team and run and buy 'em. - No, this is where you come on the podcast. You don't have to talk to anybody. - Yeah. - Just talk to thousands of people through here. So I would love my, the call to action for this would be like, oh, the other timely reason for having you on. I also feel like everything we just talked about here for all of those reasons is why I would love, I love the idea of betting on this as a strategy as a company, right? So many of the people that listen to podcasts or our companies right now, we're struggling to find ways to stand out and we can only put so much AI in the value probably of our product, except the fact there's maybe two or three other products like you, but in the click up example, like click ups on paper similar to three or four other companies. But they do good marketing through social media and so they're gonna earn my, give me to know, like, and trust you and so yeah, that, that's why I bought a click up, I kinda like their content. Be that brand, right? Is that not the opportunity right now? That's the biggest, it's the biggest mode you can have because now we're in a world where people can build things even faster than ever, right? Like it's, you used to get standout solely by your product. So most people didn't care about marketing and B2B, but that's not the case anymore. People have a choice to make and they could also go try to build, you know, like, look, we've been dealing this for a while. We have hundreds of competitors, everyone's trying to make a project management. So we're not worried about vibe coders coming. There's so much security and so much of that. But we are not only do you compete with project management, this is what you compete with. This is what I'm on, like 100% Google docs, we compete with, we compete with everything, right? So it's a great, and now we're having to turn into an AI company ourselves. So there's a whole nother podcast on that on the shift of, you know, changing your entire business, you've been working on for 10 years to still stay alive. So there's, there's that, but, but no one can take away from us as we're top of mind, right? We've ran crazy billboard campaigns. I don't know if you saw, but I boy-cotted, you know, boy-cotted slack at their own conference, right? I had people saying cut the slack with billboards. We ran ads, we had billboards there, we had, you know, signs, we went in campaign, we got kicked out the conference, and that got tons of newsletter traffic and tons of leads. So you're like, there's always something to do, but you got to take some risk. And I just watch every company marking do the same thing their competitors do. They're watching their competitors or trying to do the same thing. They're not, but the last thing I'll tell you too, is that funny is because it's our ethos. Like we choose business comedy because we are funny, right? So choose somebody that's true to you. If you like music, make music for your content, right? Like the people who really win are actually doing things they care about. And you need to figure out what you care about, what you're, I see, I see, P cares about, and then find a way to join the two. - Yeah, give you just another, like this is not really a social media example, but it's kind of in the same vein. There was a company a couple of years ago. There's a guy called Ian, who runs Caspian Studios. There's a pot there, a pot. - I know Ian. - I did his podcast. - They created a show for a company that sold to HR. It was called like Murder in HR or something. - Mm-hmm. - And it had millions of downloads and was wildly successful, and it happened to be put on by a company that sold software in that space. And it's like, the reason it worked is because they hired actors. They wrote real script. It was real. And then the brand gets all the credit from that because it was murder in HR, right? So music, whatever your thing is, beatbox. Have you seen that guy, Ari? Like the guy walks around New York City and he makes beats. He's got this big like a keyboard. - Oh yeah, dude. - Like I was like, oh, I'm gonna get this guy one day, and then sure enough, I see like, his videos like presented by Oracle. I'm like, damn it. I can't, okay, he's out of my mind. - Right now. (laughing) - Then there's like, have you seen the guy who gets on a ladder and does interviews, right? Like, yeah, perfect example. Yes, or just like a one minute, that dude, a good example. Doesn't have to always be humor unique format. Like I was actually thinking, how can I get more out of this podcast? And I'm like, what if I did, this is a trying to stack my selfish interest.
I'm like, I should create a series where I play golf or work out with. - Yo. - That's a cool idea. That would win. - I would watch it. - It's just the same concept, but when the background is like, we're on a putting green talking about marketing. It just works, right? - I look, I'm right now. If I'm, I probably should even share this about sharing it. I don't care. That's what I'm looking at right now. Like, what is my next, I'm actually moving into a role where I create more content for a clickup. Right, that's what I'm doing. I'm speaking on more stages. I want that thing. The reason why I can tell you 10 more ideas, there's a page called Trackstar where the guy walks up. He puts headphones on you. - Trackstar is great. I watch everybody from Noa Conte to LeBron James. He put songs on you, tell me, you know, who-- - Genius. - And they're like, oh, who put this song on here? - Genius. - Genius, right? So I'm looking, you mark my words, Dave. I'll come back to the next three to four months. I will have my format like that, and you'll see me making something. I don't know if it's going to be me. - Okay, let me, self-interesting. - Let me ask you a question though. For me, I live in Vermont. How can I make a show like that happen? Am I going to get on a plane? I'm going to go to New York and that's the closest city, and that's where I'm going to do it. Like, what would you do if you were Dave? - If I was Dave, I think you got it. Look, how many kids you have? - Two. - You have two kids. So you're pretty, yeah. I don't want to give advice, be away from the two kids too much, but I think you get a pops on the New York. Like, it's going to be hard to get people to come to Vermont. You still could, like, if you, like, I would come to Vermont. - Could I, but God, no. - Over time, maybe, but could it be, could it be once a month, you go there and you film a bunch of content over two days? And you have six lined up. You have six episodes lined up once a month, right? Now you're good. Now you chop those up. You got content for days. Then you start doing clipping. 'Cause, right? - This is your other people. - By the way, I don't want someone to, like, roll their eyes and be like, "Oh, look at Dave, being a bro. "Talking about he wants to do a golf podcast." Like, I would actually think that the secret game, though, is like, this conversation has become a commodity, like, you know, two people talking over Zoom, or Riverside, or whatever we're using, right? - Yep. The whole thing, it scales and changes the whole game if the background is in person, wherein person, like, I'm convinced that my podcast clips, like, they don't perform on LinkedIn because everyone's so burnt out and just banner blind to like, - They've already seen it. - Another dude with a microphone in front of his mouth, scroll. - But I'll tell you what, TPPN just got bought for 300 million. - I saw that. - 300 million, right? Like, so people are starving for the big guest, but they are starving for something new. 'Cause TPPN, they just did a different way. They made it feel like ESPN, right? They presented it a little different. So, like, there is something there. They got off course ideas there. You know, you could do top golf. - Okay, but can we, the TPPN thing though, I think people should study this, but they should also understand, like, the concept of a news show, a tech news show, has been done a million different ways. - Yes. - The secret sauce of that show, which is like, why I think content creators and marketers don't get enough credit, is, the chemistry between John and Jordi, their knowledge of the space, the little, the eagle screeching, calling their studio, the thunder dome, like, if you're gonna really go for it, and create a show, I think it has to be at that level to really stand out, versus, you know, they've just doing a bunch of interviews over remotely. - It's actually really well said. That is, because I've been, I actually have time on my counter to go study TPPN more and see what they did so well. - Yeah. - 'Cause I haven't watched a ton of it, but I mean, I'm just, that just verified to me that having an audience in B2B is valuable. Like, people like, they'd spend a lot of money for it. - It isn't to tie this whole thing back to the beginning. Like, the point is there is not social media, like, my first job out of school was, I worked at a PR agency, and I was like, essentially, the social media in turn for their clients, where I ghost wrote tweets and posted them. That era, that's over now. Social media is like, the core, can be the core marketing strategy of the business, if you're willing to put in the effort, and put 10 years in and take the time and effort that Chris has shared. So, this was awesome. We'll link to your LinkedIn. I know we were gonna show a bunch of examples, but maybe you could, I could just put, I'm gonna put a bunch of these in our newsletter. People can just flip through them directly. - I can give you some of the top ones. I appreciate that a lot. And we have fun making them, man. We have new characters. We're hiring, and on the side, we have side actors that come in. It's a full production now. - Cool. And if anything, I hope this is the conversation that's like, all right, cool. Here's an example of how this company in B2B is doing it. We're gonna take our version, propose it to our company, and make your version of it. And when you do, send a message to Chris, and I, on LinkedIn, won't give you some encouragement. Chris, good to see you. Hopefully, one time it'll happen in person. I'd love an excuse to get to Miami, or wherever you'll be in the future. - I'll make it one of your events or something, Dave. - Okay. - It's really good to connect with you. - And I do still feel the vibe from afar, and maybe we'll hang in some one. - Okay, good. - All right. Appreciate you. (upbeat music) - Hey, thanks for listening to this podcast. If you liked this episode, you know what? I'm not even gonna ask you to subscribe and leave a review because I don't really care about that. I have something better for you. So we've built the number one private community for B2B marketers at exit five, and you can go and check that out. Instead of leaving a rating or review, go check it out right now on our website exitfive.com. Our mission at exit five is to help you grow your career in B2B marketing, and there's no better place to do that than with us at exit five. There's nearly 5,000 members now in our community. People are in there posting every day asking questions about things like marketing, planning, ideas, inspiration, asking questions and getting feedback from your peers, building your own network of marketers who are doing the same thing you are so you can have a peer group. Or maybe just venting about your boss when you need to get in there and get something off your chest. It's 100% free to join for seven days so you can go and check it out, risk free, and then there's a small annual fee to pay if you wanna become a member for the year. Go check it out, learn more, exitfive.com, and I will see you over there in the community. (upbeat music)
Podcast Summary
Key Points:
B2B social media should not focus on product promotion; instead, it should aim to entertain, teach, or evoke emotion, as 99% of companies get this wrong.
Success requires giving strategies time (e.g., six months) and using testing tools like Instagram Trial Reels to optimize video hooks and formats.
Create content primarily for two platforms (e.g., short-form video and LinkedIn), but distribute across all channels, using humor or educational value tailored to the ICP.
Social media can drive real pipeline and sales, as seen with ClickUp, where funny content led to enterprise deals and CEO engagement.
Finding the right angle involves understanding the audience’s interests through direct interviews and focusing on what makes them laugh or learn.
Summary:
The transcription features Dave from Exit Five discussing B2B social media strategy with Chris Cunningham, a founding member at ClickUp. Chris emphasizes that most companies mistakenly treat social media as an ad platform, while users want to laugh, learn, or feel something. He advocates for a rule of three: content must entertain, teach, or evoke emotion, and must have a strong hook and pacing.
, short-form video and LinkedIn) and using Instagram Trial Reels to test multiple versions of each video, as the best-performing version often surprises creators. He shares how ClickUp manages 35 accounts, including a separate comedy page that has more followers than the main brand, and uses AI to identify high-value followers like the CEO of McDonald’s. This approach has driven real sales, such as a large deal with VaynerMedia.
Chris advises marketers to understand their ICP deeply through interviews, finding humor or educational angles unique to their audience, rather than just promoting products. He stresses that social media success requires patience and a commitment to creating content that resonates emotionally or practically, not just broadcasting ads. The conversation also touches on measuring impact through pipeline generation and using social as a signal for sales outreach.
FAQs
The biggest mistake is treating social media as a place to give more ads and talk about their product. When people pull out their phone, they want to laugh, learn, or feel something, not be sold to.
Before posting, ensure the content does one of three things: makes the audience feel something, adds value, or teaches them something. If it doesn't, don't hit post.
They use Instagram Trial Reels to test three different edits of a video, varying the hook, text on screen, and format. This provides feedback without affecting their main followers, and often the version they think is best isn't the top performer.
Yes, it's still worth the time. Trial Reels are easy to implement and can significantly improve performance, regardless of follower count.
ClickUp runs a separate 'ClickUp Comedy' page with business humor. They use AI to identify high-profile followers, like a CEO, and create personalized video DMs to set up sales calls. This approach has helped close major deals, including one with VaynerMedia.
You don't have to use humor; instead, teach your audience something or provide valuable news for your network. But if you know your ICP well, you can find humor in any space by interviewing them about what they find funny.
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