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Dave Gerhardt
Hey, it's Dave.
Chris Cunningham
I want to give a quick shout
Sponsor Narrator
out to Knack for sponsoring today's episode. Knack is a purpose built email and landing page platform and they're also one of our longest running sponsors. When I create our newsletter each week, I spend a bunch of time more recently with Claude, my friend Claude as my editor. But once I'm done editing the newsletter, it's not as simple as just getting my copy from a Google Doc and hitting send. If you're a B2B marketer, you know that.
Dave Gerhardt
So what happens?
Sponsor Narrator
Someone has to take that output and turn it into an actual email that renders an Outlook, so follows brand guidelines and ships. You know this story. The last mile still feels slow and manual. NAC has made this a lot shorter. They just launched an NCP server that connects your AI assistant directly to their platform. So now you can describe the email you need in Claude or ChatGPT and drafted like normal, but it automatically starts building in Knack for you. You get an email that comes out following your brand rules automatically. No manual cleanup, no broken HTML and even better quality than anything your team built by hand. The marketing Ops team at OpenAI is actually running this workflow right now. They intake internal campaign requests from Slack, an AI agent structures it into a ticket nac, MCP generates the email and a marketer refines and ships. This is the future of marketing. You should go check it out@knack.com that's K N A K.com hey it's Dave.
Chris Cunningham
I want to give a quick shout
Sponsor Narrator
out to Vector for sponsoring today's episode. Vector is a contact level ads platform. You probably have anonymous buyers lurking in your funnel, people you can't identify or follow up with, people you can't target with any real precision. So you end up throwing ads at job titles and hoping the right person sees them.
Dave Gerhardt
Vector fixes that.
Sponsor Narrator
Instead of targeting job titles and crossing your fingers, Vector lets you build audiences from actual people. The ones on your site that are clicking your ads and checking out your competitors. They're launching an MCP server that lets you connect AI like Claude or ChatGPT directly to their platform. And it connects to your LinkedIn ads and site visitor data. So instead of clicking through dashboards, you just ask your AI a question and get an answer. Hey, which ad creatives are fatiguing? Which companies are engaging but not converting? What's actually driving Pipeline right now? It turns your data into something you can use in the moment.
Dave Gerhardt
Go and check them out. It's Vector Co that's V E C T O R CO Vector. You're listening to the Dave Gerhard show. 234-12-1234. 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. So 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 pull out 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. Enjoy my conversation with Chris Cunningham. So, Chris Cunningham, founding member of the marketing team at ClickUp, you've been there for forever now for, you know, 40 dog years in tech years or whatever. What has it been? Has, has it been a decade?
Chris Cunningham
Almost. It's been right shy of a decade, about four months. Been a decade. Two months, actually. Two months now. Can I just.
Dave Gerhardt
In a world where like 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?
Chris Cunningham
The founding team, man, these are my best friends. You know, I've been through. 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, you know, like, sure, I've had opportunities to leave, especially with things popping and doing well, but I love this crew, I love this team, and I. I got to see this through and, you know, who knows what happens to me in the future, but it's the team. Okay.
Dave Gerhardt
And then how do you. You've carved out. You've played a bunch of different roles in the company as. 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 act. Oh, fuck it. It's my podcast. 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 Ahrefs or. I've 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. You've carved out this interesting role in social and content in the company.
Chris Cunningham
I think I've made up my own role, if I'm being honest. So look, yeah, at the 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. 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. 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 twerking, 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 ClickUp could I try and have this free reign. And so that's another reason why I'm still here.
Dave Gerhardt
Okay, so we're going to talk about B2B social today. The goal is to leave you with some ideas, just ways to think about things, get you unstuck, give you some inspiration that 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?
Chris Cunningham
The first mistake is so easy. It's that they, 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 all it is. Or feel some type of emotion, right? You have some people who might watch prank videos, some people who might watch videos to learn more about Claude 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 in marketing. And the problem is that's why CMOs are, you know, that's why, that's why they should be an exit 5 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 in marketing to win, you have to give it time. And sometimes it's hard to prove. And that's the, that's the challenge we face every single day as marketers.
Dave Gerhardt
Okay? So the big thing that's shifted in our personal lives is that the, for us, the majority of the shopping, buying, consuming that we do is now not only through our phones, but through some form of entertainment, whether that's Instagram, YouTube, podcast, TikTok, Netflix. I mean, I'm watching something on the couch the other day with my kids on Disney plus and there's like a Salesforce ad you know, like cpv, all this 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 and not just treat it as another, like, distribution channel. Like, oh, we got a blog post, so post about it on LinkedIn. Or like, we won this award, so post about it on LinkedIn. Can you explain the. Like, if we peel everything away, where do. Where does someone start? If I'm listening to this, you're going to give us some good examples of stuff. But yeah, how do I peel this all the way back and figure out, like, what. 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 channels? Where do we start?
Chris Cunningham
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. Like, hey, we have an event here, we need to post that. Well, I'm like, well, 1% of our audience going to 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 you 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 to, hey, be omnipresent. 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 at ClickUp, I'm creating for two platforms. And one is, you know, it can be TikTok or Instagram Reels. They're kind of the same to me, but short form. And the 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 on LinkedIn, I'm writing about thought leadership. And that's the two things. That's 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. Let's say I have one video, but I do three different edits. That takes my editor maybe an extra four minutes max. Right now I 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 you at 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 what I thought was better. And it goes to like 10 or 20 million. It's a major difference.
Dave Gerhardt
So even if you have a great idea that you love, and this video is, I love it. Press put. It's like a standard operating procedure to have three variations of it every single
Chris Cunningham
time, no matter what. And you'd be shocked how many times the one you think is the best is not the best.
Dave Gerhardt
Yeah.
Chris Cunningham
No matter what. No matter what. You should always. It's like everything in marketing. Why wouldn't you. A B test if you can and you can today.
Dave Gerhardt
And social media and does it. Does it even matter? Even if I'm. I have a, like our. Our Exit 5 company account. I know we have like maybe a thousand followers. Is that enough? Should I still run trial reels?
Chris Cunningham
Still worth the time? Still worth time. Every single time. And it's so easy. I'll show you. I'll show you. I'll send you my playbook after on how to do it. Your team can implement it in no time.
Dave Gerhardt
Cool.
Chris Cunningham
Everyone thinks that ClickUp has this big social media team. It's me, some actors that I hire 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.
Dave Gerhardt
So the. For everybody listening. So I think 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, we 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.
Chris Cunningham
And what I want to make sure you also know is that I'm posting on 35 accounts every day now. Right. So it's not just click. I have ClickUp on all the platforms. Right. Then I have ClickUp Comedy. I have ClickUp on the street. And so ClickUp is more of my product. That's where I'm helping people. That's where I'm making. That's where I'm doing more, like teaching ClickUp or here's three tips to be more productive, et cetera.
Dave Gerhardt
Yeah.
Chris Cunningham
And I have my ClickUp comedy because the comedy. I used to do both. And I realized that some people want to watch the comedy. Someone to watch ClickUp Personal. So I've made these different pages, but yes. So I'm leaning into the business humor. But when I tell you that I'm only creating for two platforms, still posting across all of them. So when I make the one video for TikTok.
Dave Gerhardt
Sure. But you must have gotten. You probably didn't have all those pages out of the gate. I'm betting that you had, like, you're posting funny things that kind of popped off on the main ClickUp channel. And you're like, oh, we could carve this out into its own page. Right.
Chris Cunningham
And I realized that the audience was getting confused and it was limiting how far I could grow. So funny enough. ClickUp Comedy. ClickUp has been around for years before Click Up Comedy. Click Up Comedy is more followers and ClickUp. Right? Yeah, but that's just because people love comedy the most. It's a bigger ceiling.
Dave Gerhardt
And it's also kind of like that could be anything that could be a comedian chant, like, click up. It doesn't go to your head. That's at 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.
Chris Cunningham
So that it is. But you know what? It's funny because there's. 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 who's doubting and thinking, oh, there's no way you can leave.
Dave Gerhardt
Did he respond to that message?
Chris Cunningham
He did not. Yet. He did not. But. But I'll tell you who we have gotten from this. I'll tell you as VaynerMedia, our fourth, one of our larger deals from last year I think is top, top seven or something. They said they found this solely Gary and then Team Saw saw our social media, like 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. They're definitely a large customer now. So we do close big deals off this.
Dave Gerhardt
Let's come back to this when we, when we talk about measurement because that's an interesting play to run that basically treats social as a signal as opposed to like we're. Wait, you know, there, there's something interesting there. Let's remember that for our art 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.
Chris Cunningham
They do tell me that all the time. And my answer back is, you don't have to. I'm not telling you 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. 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, for your people? So let's say you're an AI company. Can you 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 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 today, you drop 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, what we're doing right now. I do this two to three times a week with my ICP. I ask for a 15 minute riverside, I record it, and the first seven minutes I'm selfish. Hey, what podcasts do you watch? What's funny to you? What's something ridiculously hilarious that happened to you recently? Right? I'm interviewing real people.
Dave Gerhardt
How do you get those meetings?
Chris Cunningham
I literally am just cold linkedining, Cold linkedinning, hitting them up.
Dave Gerhardt
But do you see someone who's a customer or just an icp? Like this person looks like an icp.
Chris Cunningham
It's a mix. So I, 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 on LinkedIn. They don't have to be a customer. They could become a customer later. But it sees1 on LinkedIn is like either a project manager or 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 gonna ask you some questions. I just wanna 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.
Dave Gerhardt
Oh, so you actually record and give them something to use from that.
Chris Cunningham
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. Think about, I'm, I, 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 what's something funny that happened in the office last
Dave Gerhardt
week or totally, dude, I, I feel like I am the best at my job when I'm talking to the most amount of people. Like, 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 in a guest says something, you can tell right away in the chat that everybody kind of like, that line landed.
Chris Cunningham
They felt it.
Dave Gerhardt
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, you know, AI is like, you know, smarter child. Back in, when we all had AOL Instant Messenger.
Chris Cunningham
Oh, that.
Dave Gerhardt
Everybody loved that. Let's make a meme out of that. That's where the ideas come from. Right?
Chris Cunningham
There you go. Well, I felt like selfishly, when I first started learning about you, I was like, that's probably why he started Exit 5, because now he gets to talk to all the. He gets talked to his ICP all the time. Like, how genius is that?
Dave Gerhardt
Yeah, I'm a genius. I'm a super genius. Put clip that.
Chris Cunningham
I'm a little jealous. I need to figure it out myself.
Dave Gerhardt
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 a consulting business, and 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, I hired Dan 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 AI or cyber security or fintech or hr, it would be put. Chris, put 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 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 ClickUp?
Chris Cunningham
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 3k a month to start creating videos. Right.
Dave Gerhardt
Where did you find them?
Chris Cunningham
I've been stalking this guy for a couple years. He was at, he was running TikTok for Ad World and his name is Luke. And Luke had done an amazing job for them, grew them to 300k. 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 doesn't fully believe in hiring a creator full time yet. I promise you, if 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.
Dave Gerhardt
Do you think that's kind of the secret. What you interest. What you mentioned is kind of like the secret sauce. I see people like this all the time. Like, hey, who should I. Anybody know any good? Anyone good to hire? Where I feel like the best people often it's like you or 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 feed 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. It's so many people that are good at what you're describing. I'm like spitting this back for our listeners. Like, this is the skill. It's it. 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.
Chris Cunningham
And now we're talking. I designed my feed to be this way. Like my feed. I have found so many creators who are big now and I found them early and you can go look. And a lot of them have been in a click of 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 stayed in. I found a way to get in touch. I'm also relentless. I'll get in touch. Everyone knows it's a ClickUp. I'll get in touch with anybody, doesn't matter how big, 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, I, I network 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 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, our HR 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 then same with sales. My sales team tells me that they start now asking after they close the deal, how'd you first find us? And a lot of times they will say, social media, it's 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 Guarov, 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 at the time. I was only spending like 7,8k a month. So what do they care? You know, that's fine, we can spend that, take a little bit out of the ads, right? And, and our CAC 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 overseas, like from Australia, or something. And I'll never forget Lightfoot, the rep was like, yeah, they said they found us from the videos and they were like, okay, we're onto something then. Vaynermedia.
Dave Gerhardt
The rep is called Lightfoot. Shout out to Lightfoot.
Chris Cunningham
Yeah, Jonathan Lightfoot is his name. Great, great, incredible sales guy. I think he won so many awards at SKO this year. But he was just telling me that was one of those. The first signal I saw that got so excited. And now I get it all the time. The reps are pinging me all the time.
Dave Gerhardt
Yeah.
Chris Cunningham
Hey, they love the HR guys. I mean people ask them to bring them out and there's different characters that people know.
Dave Gerhardt
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, 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. The less you make it more like direct response marketing, the better it actually does. And so if it was an ad for ClickUp, it might not be as good if it was a funny ad for ClickUp. You know what I mean? Like it's just like every single time.
Chris Cunningham
That's the hard. 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 product, if you're building what everyone else is building, you're probably not going to win. Right? But you got to go where someone else is not playing.
Dave Gerhardt
You can, you can sprinkle in like you can when you have something interesting from a ClickUp 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 haha 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, you know, we are always searching for the thing that's going to do it this month, this quarter. But I had Devang VP from LinkedIn on a couple weeks ago and he said the average B2B buying cycle now is, you know, whatever, 211 days.
Chris Cunningham
Sure.
Dave Gerhardt
So our goal then is like, how do we get people to see as many of these fun, interesting, educational, whether it's new, what do you want to, whether you want to, you know, you said feel something, add value or teach.
Chris Cunningham
You got it.
Dave Gerhardt
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's working and then obviously you have your results and views and you can sort, you can go through engagement and, and kind of like pick out the little pockets of things that were working and go do, do more of it. How much did the volume of what you're creating? So you hire this guy, you know, spending 7,8k a month. It's, it's you and him, you're making videos. Were you making like one video a week? Are 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 did you really become a lead at the creation here? Because me, I got this dumb little Instagram page. I make for myself my fun, my own videos and I just like you running yourself. No, not for real. Just like Dave Gerhardt, like on Instagram, like of me doing like pull ups or something, right? And it's like I make one reel 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.
Chris Cunningham
I'll tell you this. I have something, I have the popular thing, but I also have something that's not. It is about reps, but there's also, there is a limit to it. So I'll tell you this, I'll take you through the whole thing real fast. We started with the first three months with just me and Luke, right? 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'd shoot for a week, we'd shoot one day and we'd have enough for like maybe one to two weeks and then we'd shoot again. I'd have to fly out, you know, staying in San Diego. A lot of the 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 that, 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 is very like this. And so this is the click up way. Okay, you hit 30. Now how do you get to 100? Right? I'm like, 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 the 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 a piece. It's me, my actors, a couple other worker employees, and sometimes I hire a 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 a writer's room, bring some ideas. Okay? Then on Tuesday. Oh, sorry. On Monday, we all pitch 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 won. If someone really feels good about something, they can bring up their idea again, but that's it. Tuesdays, we fine tune it. We fine tune the 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. And now we just keep going. So we keep running that every single week. But now that got us to 100 million impressions and then really to 200 million. But what Guarav 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 ClickUp content. 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 months. So my thing is there is a sweet spot and for videos like we're making, I think people like, like 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 second. And there are some people who say differently, like if it's a personal account, you might want to post eight and nine times. They get more reps and something hits. Right. You have more chances.
Dave Gerhardt
So do you have a target for how many, how many you're trying to publish in a week now based on this?
Chris Cunningham
Yeah. So for my ClickUp comedy account, it's 7. For my ClickUp brand account I usually go for 10. I still post twice a day on that one. I think it still works. Yeah. And then for man on the street, four or five. The ClickUp memes. Memes 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. One of the things that you can get attention from and they're smart to add to your social media strategy, but they don't drive signups in my opinion. Unless you really become their meme dealer.
Dave Gerhardt
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? Today's episode is brought to you by Compound Growth Marketing. They're a full funnel demand generation agency that I've actually personally hired twice. That's right. Before I was a thought leader, I was an actual marketer, an operator, a VP of marketing myself. And CGM was one of the best agencies that I've ever hired. They help high growth cybersecurity, DevOps and enterprise software companies show up earlier in the buying journey where potential customers are actually forming opinions about which products to use. CGM is great because they offer the combination of AI, SEO, modern paid advertising strategy and a dedicated go to market engineering team that you need today. So everything CGM does gets tracked, measured and improved over time. That means more pipeline for you and this works because they were started by a former VP of marketing who gets this space. They really understand B2B. So if you're in search of a new agency that can help you hit the number this quarter and you need help with things like AI, SEO and paid media, you should definitely go and check out Compound Growth marketing. I call them CGM Compound Growth Marketing. Go and check them out at compound growth marketing. Com and tell them that Dave and Exit 5 sent you. Yeah.
Chris Cunningham
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 one like it was just us, we had no camera person, just iPhone straight up.
Dave Gerhardt
Yeah.
Chris Cunningham
Now today, funny enough, we still shoot with an iPhone for the most part every now and again if we're doing a music video or something higher end, we will use a DLSR. But for the most part still iPhone. IPhone still wins. And I'll tell you something that really works well is when you make it look almost like it's Snapchat or something. Like so it just looks like something just started. Those do so well.
Dave Gerhardt
Yeah. And this is you, this is you guys doing this like in the office or something or where.
Chris Cunningham
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, we also have a studio that we rent, that we kind of share rent in Orange County. And so most people, most of the shoots are in Orange County. Every now and again we use a ClickUp office. It's very nice.
Dave Gerhardt
Aren't you in like Miami or something like that?
Chris Cunningham
I'm in Miami. I'm not every shoot anymore. I'm flying 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 wild. Zeb has flown out our nine or ten 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 feel of how ClickUp's 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 going to be shot. But the team is so pro that they show up and they shoot and they handle it.
Dave Gerhardt
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.
Chris Cunningham
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, clicker's getting pretty big, so I want to make sure I'm preparing myself. I'm in Florida and I like it here, but. Yeah, so I fly in and I still have. I'm still heavy, heavily influenced and, you know, up to the day. But they can run it once we have the scripts. And they're pros, but they're filming and
Dave Gerhardt
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 going to be in the rotation for Monday, or is there a longer time window?
Chris Cunningham
Yeah, we're so far ahead now, if I'm being honest, Dave, like, I probably have 80 videos in the bank. Like, we cannot shoot for a while, and I'd be fine. But that's because we keep. We get more than we need to post.
Dave Gerhardt
So basically, that's the whole game. And anytime I've run into, like, a slowdown 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, then 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. My. The next idea is the exciting one. And so there's like, how do you. How do you not Forget about the 80? Like, well, 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 going to prioritize that one. Like, in the ship at the next week.
Chris Cunningham
You just took my next few lines.
Dave Gerhardt
So every time always happens, I feel we're like two.
Chris Cunningham
Well, some. There's also two that are timely, right? Like, maybe, like, you know, like, maybe like something phenomenal might happen. Like the. The. The Coldplay 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 giving you an example. If it's something big and timely, we'll put out immediately. But for something that's 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 have a bank and we know where they're at and we sit on Fridays. We typically go through like, okay, what's in the bank? We need to get back out.
Dave Gerhardt
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 bulk kind of analyze all this stuff? Are you going to each video and writing it down by hand? Tell me the, tell me that side of the process.
Chris Cunningham
Yeah, I actually, it's so funny. I've tried almost every tool you can name and I've, you know, Sprout Social, Dash Huts and I've. 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 and I don't mind shouting them out. Great. Vitaly 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.
Dave Gerhardt
So Vista Social will put that stuff on Instagram, TikTok all the places you needed to go.
Chris Cunningham
We post via Vista and it also tracks everything.
Dave Gerhardt
And is it a myth, fact or fiction that using a scheduler impacts reach?
Chris Cunningham
I, 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 will post manually. A lot. Even Thu Vista will still post manually. But there's times where a social media person's traveling and we schedule and it's been just fine. So I'm starting to lean. It's a myth. But if you'd 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.
Dave Gerhardt
So I do too. I believe in both sides of it. I think it's like anything in life. It's like sometimes you have to, you have to do it because it's not realistic to always be posting native.
Chris Cunningham
Yeah, I think you have to. And now I've seen no problems. I think, I think like a couple of years ago they did used to do it, but I think now there's pressure and they don't anymore.
Dave Gerhardt
Okay, and then what about like looking at success? There's probably, you know, top of the funnel. Stuff that. That you look at. You're. You're doing that manually or that's coming through the tool also.
Chris Cunningham
That's coming through the tool. So we analyze it. So Vista will give us weekly reports, and so we'll look at it. So every Friday, I come in and I'm like, okay, what platform we get? And it's funny, it's funny. It changes. Like, if you'd asked me six, seven months ago, I would say six, seven. I would say TikTok was our number one. Right? And then now it's shifted. Now Instagram has been our number one, but now Facebook. Do not sleep on Facebook reels. Make sure you're posting your podcast of Facebook reels. We are getting insane.
Dave Gerhardt
Oh, God. I can't. Chris. I can't. I'm not. No, I can't go. There's a tool.
Chris Cunningham
I'll show you how to do it.
Dave Gerhardt
Okay. If you could just press a button
Chris Cunningham
and Facebook reels is actually popping. It's been. 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 wasn't using Facebook, I had half the numbers.
Dave Gerhardt
So that is someone seeing your page in their feed. If they're just. If they're not using Instagram, but they're seeing the reels from the Facebook app.
Chris Cunningham
Yeah, Facebook reels. And you got to think that's a pretty good audience on Facebook. It's like that, you know, 38 to. To 60 that are on there. So they're usually decision makers.
Dave Gerhardt
38. This guy just put me in a box. I'm 38 on the number.
Chris Cunningham
I'm right behind you, bro. Don't. I'm coming up. Coming right. Look, I'm the one. I had to have hair surgery, okay?
Dave Gerhardt
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. Your approach is like, they can all be, you know, Instagram and TikTok can be used kind of interchangeably. Obviously, Facebook reels in that same bucket. But it's this first.
Chris Cunningham
And YouTube shorts.
Dave Gerhardt
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?
Chris Cunningham
Exactly.
Dave Gerhardt
Let's see, what else. 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 here's my question. Where would you start? I want to know where would you start?
Chris Cunningham
Hit me.
Dave Gerhardt
And then what about, ah, 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. Like, I don't want to do that.
Chris Cunningham
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, you're never gonna know what they like, you never gonna know what they want. You're never gonna know they 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 when they said they pull out their phone, they like to laugh. Maybe this is what I. Maybe Chris Cunningham was right. I do 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 who has 3,000, 4,000, 8,000 followers, but they have one video.
Dave Gerhardt
Yeah, they got that one pin, one pin reel with like 1.2 million. You're like, but they got, you know, 6,000 followers or something.
Chris Cunningham
There you go. Gold. When I see that, I get 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, if you can hit once or twice, usually look for more than one hit, maybe two or three.
Dave Gerhardt
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 wanted 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 Gonna pay me a thousand bucks a month to, like, make them six videos. Like, that's a. That's a great deal, right?
Chris Cunningham
You. I couldn't tell you how many people I found first. And now, like, look, 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 flew them out to Super Bowl.
Dave Gerhardt
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 got. You got to have your phone. You're going through these and you're like, I'm just going to DM all these people and see who I can get.
Chris Cunningham
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 was like, yo, what up? Your videos are great. I like. Like, I. Like, this was funny. This made me laugh. I think you have some talent, right?
Dave Gerhardt
I run marketing at a software company. Like, could you, you know, would you be interested in doing something together?
Chris Cunningham
Would you be interested. Look, I can't pay you a ton because your followers are low right now, but 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.
Dave Gerhardt
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 Pomerantz, 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 ClickUp. 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?
Chris Cunningham
It's very possible. Look, like, I have a new actor now. Vince. I don't know if, you know, he's a guy rapping and doing some of the new stuff. Like, he's become a big actor in the Three, and I also have other actors that I pull. So I'm always finding new talent. I'm always sometimes flying other talent out from New York. I'm finding new people in this, you know, in la, because 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 the.
Dave Gerhardt
What is your budget for this? How do you have LA studios, this and that? Like.
Chris Cunningham
Yeah, studios. Probably 2K a month where there's other people renting it. We just rent it for one day a week. So studios, 2K a month, you know, have my actors that I pay full time. They're paid great, but nothing, you know.
Dave Gerhardt
Wait, those are full time ClickUp employees.
Chris Cunningham
I've hired them full time. Both they have full time salaries, insurance, and they're vesting 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.
Dave Gerhardt
So can they not make videos for other people? Is it like part of the, the deal of being a creator with you guys?
Chris Cunningham
I stay pretty chill about it. Like if they're doing. As long as they can't go do a ton, but they want to take a video, it's not a competitor here and there. I want them to, I want my actors to get extra money. I'm not one of those, you know, I could, I probably could. It's. It's in the.
Dave Gerhardt
And the two people that are full time, they were contract, like doing side. Side work for a while.
Chris Cunningham
Yeah, they were doing side work. The other guy, Adam wasn't 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.
Dave Gerhardt
All right, so be, be curious. Find an angle that isn't just promoting your own stuff. Feel something, add 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 listening, I would love to prove like the humor works. But also I feel like this thing for me, you said feel something, add 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 5 that like, I love. Then 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 Martech Manufacturing. This company makes the infrastructure that supports X, Y, and Z. I'm like, these. These are amazing examples. Like, there's got to be. You can't tell me there's not a creative angle for social media for. For those companies.
Chris Cunningham
You drop me in any one of those, I'll do it again. That's because I don't know. Now that I know the formula, there's always something, right? It's just finding nuances. Like, in any of those business, I guarantee you something funny that all those people who are their icp, they laugh at, right? But you just got to be inside. You got to really hang with these
Dave Gerhardt
people to know, okay, what. How do you feel about AI in this world? As a marketer, social media person, creator?
Chris Cunningham
I think I don't have the perspective that everyone is so cool to say. Like, I 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, you know, we 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 on 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? And Santa Claus was AI. We had a real person interviewing him, and we made it feel like kind of like Diary of a CEO Podcast. It was like, dramatic and da, da, da. So, like, we. We. 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
Dave Gerhardt
a. 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.
Chris Cunningham
Why it's easy for me. I don't think humans yet enjoy AI content more than content from other humans. I don't enjoy. When I see an AI video, I know it's AI scroll. I quickly scroll. It's not real. And I think that's why I see a shift 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 polished.
Dave Gerhardt
I saw like Chamath had posted this on Twitter and was getting 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. Like, I love the raw. It almost feels like the Instagram stuff that's working right now feels like like divine type of stuff. It's like silly 10 second, like some guy raw, real. I'm watching this guy. You ever seen this guy?
Chris Cunningham
He eats.
Dave Gerhardt
He eats like a onion on a plane or a li. A lemon on a plane.
Chris Cunningham
Of course this is real. Because AI can't. It just can't replicate it.
Dave Gerhardt
And.
Chris Cunningham
And right now the scripts aren't good. You know, I can tell when someone uses AI to write, just like you can.
Dave Gerhardt
Interesting to 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?
Chris Cunningham
And we will at some point. But.
Dave Gerhardt
Yeah, but what? Online, it's just like, all right, I'm going to hang up this call and I'm going to 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 whatever at these creatures, as humans, we. We need to be around real people. And so there must be something in our brains that goes off. I was like, this is kind of
Chris Cunningham
looks like a fake thing.
Dave Gerhardt
I'm not into that. I feel. I really believe that this might be
Chris Cunningham
the best way I've articulated. I've heard it articulated is because I think so I think people, like, they want. They want to be connected to real. They don't. They don't want. 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 and they get some views. But then the day, like most people want human connection. They do. They love. They love it. And they missed it during COVID And that's why events surged, you know, after Covid. Right. Like, and that's why events are doing so well now because people want to be around people.
Dave Gerhardt
I just. So during these, I keep, I put some notes in. In our slack and I'm just like making bullets of interesting stuff as they come up. And I, 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.
Chris Cunningham
Oh, yeah, sorry about that. I'm happy to talk to the team and, and run. Run it by them.
Dave Gerhardt
No, I mean, this is where you come on the podcast. You don't have to talk to anybody. You just talk to thousands of people through, through here. So I, 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 this podcast are at companies right now where like, we're struggling to find ways to stand out and we can't. We can only AI. We can only put so much AI in like the value prop of our product. Like, except the fact that there's maybe two or three other products like you. But in the ClickUp example, like clickups, you know, on paper, similar to three or four other companies.
Chris Cunningham
Sure.
Dave Gerhardt
But they do good marketing through social media. And so they're going to earn my get me to know like and trust you. And so, yeah, I don't know. That's why I bought ClickUp. I kind of like their content. Like, be that brand. Right. Is that not the opportunity right now?
Chris Cunningham
That's the biggest. It's the biggest moat you can have. Because now we're in a world where people can build things even faster than ever.
Dave Gerhardt
Right.
Chris Cunningham
Like, it's. You can stand out 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 doing this for a while. We have hundreds of competitors. Everyone's trying to make a project management. We're not worried about vibe coders coming. There's so much security and so much of that. But we are.
Dave Gerhardt
Not only do you Compete with project manager. This is what you compete with.
Chris Cunningham
This is what I'm on, like 100% Google Docs. You know, we compete with. We compete with everything, right? So it's a great. 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.
Dave Gerhardt
There's that.
Chris Cunningham
But. But what no one can take away from us is we're top of mind, right? We've ran crazy billboard campaigns. I don't know if you saw, but I boycotted, you know, boycotted slack at their own conference, right? I had people saying, cut the slack with billboards. We ran ads, we had built. We had billboards there. We had not, you know, signs. We went and campaigned. We got kicked out, kicked out of the conference. And that got tons of newsletter traffic and tons of leads. So you, like, there's always something to do, but you gotta take some risk. And I just watch every company in marketing do the same thing their competitors do. They're watching their competitors. They're 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? It's who we are. So choose something 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 your ICP cares about, and then find a way to join the two. Yeah.
Dave Gerhardt
I'll 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 years ago, there's a guy called Ian who runs Caspian Studios. There's a pot. They're a podcast.
Chris Cunningham
I know Ian. I did his podcast.
Dave Gerhardt
They created a show for a company that sold to hr. It was called, like, Murder in HR or something. 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. In hr, right? So music, whatever your thing is. Beatbox. Have you seen that guy Ari? Or like the guy who walks around New York City and he Makes beats. He's got this big, like, keyboard.
Chris Cunningham
Oh, yeah, dude.
Dave Gerhardt
Like, I was like, I'm gonna get this guy one day. And then sure enough, I see, like, you know, his videos, like, presented by Oracle. I'm like, damn it, I can't. Okay, he's out of my.
Chris Cunningham
Then there's like, have you seen the guy who gets on a ladder and does interviews? Right? Like, yes.
Dave Gerhardt
Perfect example. Yes. Or just like, a one minute. That's. Oh, dude. A good, 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, but I'm like, I should. I should create a series where I play golf or work out with yellows.
Chris Cunningham
That's a cool idea. That would. That would win. I would watch it.
Dave Gerhardt
It's just the same concept, but when the background is like, you know, we're on a putting green, talking about marketing, it just works, right?
Chris Cunningham
I. Look, I'm. Right now, if I'm. I probably shouldn't even share this. I'll share it anyway. I don't care. That's what I'm looking at right now. Like, what is my next. I'm actually moving to a role where I create more content for ClickUp. Right? That. That's what it. 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. Like, if you're. There's a page called Track Star where the guy walks up, he puts headphones on you.
Dave Gerhardt
Track Star is great. I watch everybody from Noah Khan to LeBron James. You put. Put songs on, you tell me you know who, and they're like, oh, who put this song on here?
Chris Cunningham
Yeah, Genius. Genius, right? So I'm looking you. 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 gonna be me.
Dave Gerhardt
Okay, let me selfish. Let me ask you a question, though. For me, I live in Vermont. How could I make a show like that happen? Am I gonna do. I gotta get on a plane. I'm gonna go to New York, and that's the closest city, and that's where I'm gonna do it. Like, what would you do if you were Dave?
Chris Cunningham
If I was Dave. I think you got it. You look how many kids you have.
Dave Gerhardt
2.
Chris Cunningham
You have two kids? So you're pretty. I don't, I don't want to give advice to be away from the two kids too much, but I think you, I think you gotta pop something in New York. Like, it's gonna be hard to get people to come to Vermont. You still could. Like, if you like, I would come to Vermont.
Dave Gerhardt
Could I.
Chris Cunningham
You gotta know I.
Dave Gerhardt
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
Chris Cunningham
have, 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.
Dave Gerhardt
Because.
Chris Cunningham
Right.
Dave Gerhardt
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, I would actually think that the secret game though is like this conversation has become a commodity. Like, you know, two people talking over, over zoom or Riverside or whatever we're using.
Chris Cunningham
Right?
Dave Gerhardt
Yeah, it, the whole thing, it scales
Chris Cunningham
and changes the whole game.
Dave Gerhardt
If the background is in person, we're in person. Like, I'm convinced that my podcast clips, like, they, they don't perform on LinkedIn because everyone's so burnt out and just banner blind to like another dude with a microphone in front of his mouth. Scroll.
Chris Cunningham
But I'll tell you what, TPBN just got bought for 300 million.
Dave Gerhardt
I saw that.
Chris Cunningham
300 million, right. Like, so people are starving for the big guest, but they are starving for something new. Because tpbn, 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. The golf course idea is there. You know, you could do topgolf.
Dave Gerhardt
Okay, but can we. The TBPN 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. 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 Thunderdome. Like, if you're going to really go for it and create a show, I think it has to be at that level to like really stand out versus, you know, Dave just doing a bunch of interviews over remotely.
Chris Cunningham
It's actually really well said. That is Johnny, because I've been, I was, I actually have time on my counter to go study TPB and more and see what they did so well. Yeah, because I haven't watched a ton of it. But I mean, I've just, that, that just verified to me that having an audience in B2B is valuable. Like, people, like, they just paid a lot of money for it.
Dave Gerhardt
It is. And 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 intern 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 that Chris has. Has shared. So this was awesome.
Chris Cunningham
Love it.
Dave Gerhardt
We'll link to your LinkedIn. I know we were gonna, we were gonna show a bunch of examples, but maybe you could. I could just put. I'm going to put a bunch of these in our, in our newsletter. People can, can just flip, flip through them directly.
Chris Cunningham
I can give you some of the top ones. I appreciate that a lot. And we have fun making a man. We have new characters we're hiring and on the side we have like, side actors that come in. It's a full production now and if
Dave Gerhardt
anything, I hope this is the conversation that's like, all right, cool. Here's an example of how this company and B2B is doing it. We're going to take our version, propose it to our company and make, make your version of it. And when you do, send a message to Chris and I on LinkedIn. We'll give you some, some encouraging. Chris, good to see you. Hopefully one time it'll happen in person. I'd love an excuse to get to Miami or whatever you'll be in the future.
Chris Cunningham
I'll make. Yeah, I'll make it to one of your events or something. Dave, it's really good to connect with you and I would. I do still feel the vibe from afar and maybe we all hang at some point. Okay, good. All right, Appreciate you.
Dave Gerhardt
Hey, thanks for listening to this podcast. If you like this episode. You know what? I'm not even going to ask you to subscribe and leave a review because Pine, 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 5. And you can go and check that out instead of leaving a rating or review. Go check it out right now on our website exit5.com our mission at Exit 5 is to help you grow your career in B2B marketing and there's no better place to do that than with us at exit 5. 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 want to become a member for the year. Go check it out. Learn more exit5.com and I will see you over there in the community.
Date: April 16, 2026 | Guest: Chris Cunningham, Founding Marketer at ClickUp
This episode is a tactical masterclass in modern B2B social media, featuring Chris Cunningham, a founding member of ClickUp’s marketing team. Host Dave Gerhardt dives deep with Chris into the processes, strategies, and creative risks that transformed ClickUp from a startup into a B2B social powerhouse—building a machine that generates real revenue and brand momentum through authentic, intelligent, and wildly creative social content.
For specific campaign examples or ClickUp’s top social posts, see the links in the newsletter/email accompanying this episode. Chris is open to DMs for advice, and both he and Dave encourage listeners to make this strategy their own and report back!