← The Marketing Millennials
The Marketing Millennials
How To Win in B2B in 2026 with Chris Cunningham, Founding Member at ClickUp | Ep. 378
00:40:28
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- [00:01]
CallRail Narrator
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- [00:28]
Daniel Murray
Welcome to the Marketing Millennials, the no BS marketing podcast. I'm Daniel Murray and join me for unfiltered conversations with the brains behind marketing's coolest companies. The one request I tell our guests stories or it didn't happen. Get ready to turn the off.
- [00:54]
Podcast Host
What is up? We are back with another episode of the Market Millennials podcast. Today I have the Chris Cunningham, founding member, ClickUp. And you might see ClickUp everywhere. Chris is a part of that. He runs all the social. He does a lot of other things I don't know about at ClickUp because he's just a man of many talents. But the social is what ClickUp is like known for. They crushing it on all channels and we're going to dive in today. So, Chris, welcome to the pot.
- [01:20]
Chris Cunningham
Happy to be here, man. I've been watching it for a long time and friends with you for a while. So I think that the time has come for us to, to do this finally.
- [01:27]
Podcast Host
Let's just get into, like, first, let's get into the story of how you even got involved in ClickUp and how you got involved in social. And then we'll get into how. What's working, what's not.
- [01:39]
Chris Cunningham
Yeah. So they almost go hand in hand. Content's always been a big part of my life in the early days. And how I got a part of ClickUp is really just meeting Zeb in college.
- [01:47]
Podcast Host
So.
- [01:48]
Chris Cunningham
So Zeb, for those of you who don't know, CEO, founder, real genius of ClickUp, who is the builder, the architect, everything behind what we're doing. And me and him met in college and we were just bored. You know, we really didn't think that everything we were learning we were going to use and we wanted to do some of our own things. And so we ended up taking on our first venture, which was managing a rapper. And in doing that, we realized that social was gonna be a big part of us getting this rapper attention. So we did. We started really learning social media, learning how to grow, learning how to get attention, and that worked really well. It allowed us to get a song on the radio, allowed us to get a tour. So our little rapper, we were managing we were opening up for, for Wiz Khalifa, Mac Miller, even if it was like the first, smallest opening act, we were doing that and we were on the tour and that was awesome. That was cool. And then, you know, as I graduated before Zeb, I got into the, the working world. I was one of the youngest managers at a company called Cvent. And when doing so, Zeb continued learning what we we did from the rapper and created like an agency. And I would help him on the side while still at Cvent. And there's some things that I learned while being there, like, hey, corporations are really going to need to start getting big on social. Should I see this happening? So we started building like an agency to help companies with social. And that was our first project together. I left Cvent to go work with him because I believe in Zeb. I've always believed in him. And, you know, we grew the agency pretty big. And then one day Zeb has a near death experience, like Lily almost died. And he comes back from that. He's, look, I don't want to just be somebody who grows social. Like, I want us to be people who change the world. And that's when we had a bigger plan. So the first one was to create a new social media app. At the time, Snapchat was the biggest app of its time. It would erase all your memories in seven seconds. Everything you, your best memories were gone. Right? We thought that was a fatal flaw. So we created this app called Memory and it looked hot. We thought, we're gonna be the next Zuckerberg. From there, Snapchat, Bill, Snapchat memories. We lost all our money and we had to pivot. And that's what a lot of people know about ClickUp. We really had pivoted. Our first mission was something else. But we had built this tool internally because we hated working with other teams. And some people would be in Sana, some would be in Trello, some would be in Jira. And no one seemed to love their tool. And that's when we decided to go all in on ClickUp. So that's how I got in. And I've always been obsessed with content. And even at the earliest of ClickUp, I wasn't doing with so much content for us, right? I was doing everything else I could. I was our first sales rep, I was doing customer service, I was writing blogs, trying to run ads, just anything marketing I can do. And as we grew, that's when I got to create this perfect role for me, which is, you know, taking content, being ahead of the Content game and making sure we have a brand. People know about us, people talk about us.
- [04:17]
Podcast Host
I actually think I remember the social agency days because I used to live in San Diego and I used to see you guys marketing jobs and then you switched to this app and I was like, wait, weren't they a social media agency?
- [04:33]
Chris Cunningham
Yeah, we were, we were. We pivoted. So a lot of people know that we. It was a pivot.
- [04:38]
Podcast Host
Let's go into it. So you, you've generated some crazy numbers. You're in the B2B space where people say, social doesn't work. Social, you can't use TikTok, you can't use video, you can't have fun. Let's go behind the strategy of how you think about social and how brands should think about social, especially in the B2B space.
- [05:00]
Chris Cunningham
The best way I can say that I think about it is almost how I've done everything in my life. Like when I look at school, you know, everyone told me, hey, get one job, move your way up. I've always felt like what everyone says is not always right. Right. And that might be arrogant. That might be like the wrong thing to say, but it's honestly always how I felt. I think sometimes when everyone is saying something, it's not right. It doesn't mean it's right. It doesn't mean it's wrong always. But I've always liked to go against the grain. And so when I really fully took over all the content and everything at ClickUp, I was like, I want. I always have everyone telling me what to do. Right. But I see what I believe, and I believe that a lot of things that they say we can't do in B2B are going to be big. The first example is influencer marketing. People don't remember this, but like five, six years ago, influencer marketing was not really a thing. And B2B, but it wasn't B2C. And my number one rule is if something works in B2C, it's probably going to work in B2B just a little bit later. And that's why I really went hard on influencers early on. And now we see how successful that's been and. And, you know, everyone does it and everyone saw it. And so now the next thing that I saw is that I believed that everyone was going to have a creator because the space is getting tighter. Like, you can't just, you can go still pay for super bowl commercials like we did, but it's not going to have a consistent impact. Right. It might have one big impact for you, and people talk about you and put you on a different stage. But if you want eyeballs every day, that's something new. And that's where you have to win in the creator economy. And so that's why I wanted to invest in the creator economy. And I went to our board and I asked him, hey, let me get one creator that just works for us all the time is creating videos. Okay, look, we're not going to hire them full time to start. We'll let you test. And this is what I challenge any good marketer. I'm sure, Daniel, you've interviewed tons of people who say this, but in marketing, you need to test with a low budget first. Look for some signal, and if you see it, then you go all in. You capitalize, right? And that's exactly what I did. I found this guy Luke, very talented, had already built a TikTok for, for one big company called Ad World. And I saw he knew how to do it in a B2B way. So I hired him and I, you know, chased him for a while, hired him, and at the beginning, just me and him working and we were making the videos ourselves. And from there we didn't have much success the first month. Then the second month we started having a few videos hit a million. And by the third, we had videos hitting 10, you know, 10, 15 million. And once we had millions of views, the board was like, hey, we'll do anything we can to keep doing this. And that's when I hired Luke full time and then hired a second actor full time. And this became a whole motion that we do.
- [07:14]
Podcast Host
So let's go over the motion. I mean, you saw creators were a thing and you needed a face for the brand, which I think B2B are still behind that. But yeah, creators internally are a great move. So what's the process of making a video with creators? What is like Monday, Tuesday, Wednesday, Thursday, Friday, look for you when coming up with ideation, video posting, re strategizing, I'll.
- [07:44]
Chris Cunningham
Give you the whole play. We run it like this on Monday. We've all come together and we look at everything we did last week. Okay, this is what worked, this is what didn't, and let's act on that. Tuesday, we all come. This is today, later today, I'm gonna go in about two hours, I'm gonna pitch all my ideas to the team and everyone comes together with some ideas and they say, okay, I saw this work or this worked for us previously. We all pitch about three to four ideas and at the end of that, we vote and we say, okay, these are the best ideas. These are what we're gonna shoot on Wednesday. We fine tune them. We perfect the scripts, perfect the hook, perfect. Who's gonna act as what role. And then Thursdays we shoot and we shoot from 8am to 6pm we get as many videos as we can. Sometimes five, sometimes four, but as many as we can. And then from there, now we have our videos for the week. Now we have everything. And then Friday is kind of our day to chill out, look at what we did, make sure we analyze and say what, what's going to post on what day and then plan out again. So you have really two planning days on Monday and Friday, planning and analyzing days. And then the action days are Tuesday, Wednesday, Thursday. That's what most people need to realize is if you really want to win and content. This isn't just a hey was wake up one day, write some scripts and shoot. It's not like that. You got to build a machine. You need an operation. And that's what we've really done well here.
- [08:54]
Podcast Host
And what is, what is the ideation look like? What is the criteria that people have to meet when ideation? I feel like there are some guardrails because you're, you're B2B brand, but also you trying to get some sort of message in the market. So what, what are those guardrails look like?
- [09:12]
Chris Cunningham
Yeah, look at the beginning, you know, they were like, hey, we need the brand in every video. And I kept saying, like, you can't do that. Right? Like, think of TV when you watch TV, it's like 85% TV, 15% commercials. Right? You can sneak it in every now and again, but if you're just doing that, you're just gonna be putting that bucket or people are gonna scroll. So some of the guardrails we have is obviously, I'm not gonna go too far and go too crazy. I don't want legal in my ear. I don't want to be having any trademark issues. I don't want to get sued. I don't want to have people hate our brand. So we're very careful in speaking about, you know, the topics like politics and things like that. We don't touch any of that. But we do. But we, other than that, we don't have too many guardrails. It's a lot of having fun. It's a lot of like, even when we have the scripts written when they're shooting sometimes some of our most like viral videos just came from what we call letting them play. So sometimes the actors are like, yo, we got this really cool idea. We're like, you know, go run with it. Go crush that. And we allow them to do it. I think that's been a big play.
- [10:04]
Podcast Host
Going into that too. I know we talked about this, but you. You also have, like, a writer's room type thing where you also bring. Bring in guests and new ideas and cool, different things. So what does that look like in the writer's room and how many times you bring in, let's say a comedian versus someone to just refresh the ideas? Because I think that's a problem with a lot of marketing teams as well. As you get into this box where you can't come up with ideas or you stuck with ideas or you can come up with new ideas, and you just need another pair of eyes to just come in and say, hey, let's just do this or this or this. So what does that look like?
- [10:46]
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- [11:25]
Chris Cunningham
So well said, man. And I think that's the biggest mistake of most marketing teams, right? Hey, we're the best. We're the best. We're the best. But no, it's. You need to have other people come in. You need a fresh set of eyes. You need a fresh perspective. So I would say of everybody, we do four writers rooms a month, right? I would say one to two of them. We bring in another writer. I might just bring in another employee at ClickUp who has a cool perspective or a cool idea. But I'll go out and I'll find, like, another comedian, another content creator, and I'll just pay them and say, come to this. Come to this with, like, three ideas, but also hear us out and help us punch up our ideas. And it's insanely valuable because sometimes you get stuck in a box. You've created the same type of content. You get kind of stuck on what you think is working, but then you bring in someone else who has a new idea, new perspectives, new life, different jobs, you know, from you. And they bring things that you never would have thought of and they really hit. So I would say about 50% of the time, 30 to 50% of the time, I'm bringing in someone else. I want some fresh ideas.
- [12:15]
Podcast Host
I know. So you, for example, let's go and down one road of like a series. So you had that, like the HR parody song series that you came up. I think like something that people miss with content, especially in B2B, is like serializing the content. And I give it. If one video works, come up with the next part of the series and next part of the series, next. Don't just come up with one idea and then just post that idea and it doesn't work. So how do you think about, like, serialization of content, making sure that people see that?
- [12:46]
Chris Cunningham
So the main way that I serialize content, the way I think about is I use the ABCD formula. And the ABCD formula works like this. When you do have something that works, you've struck gold. That's why you create content, right? So when you have that. That goal that you found, we call that an A. And what that means is that's like the first time we did the HR dancing, right? Like, first time we did that, we could have just been done with it, right? So we had a great video. Let's keep creating new. That's. That's a mistake. When you struck gold, you need to capitalize on gold. You need to recreate it. But don't do the same thing again. Find a new way to do it. So I'll give you an example. The first two is HR goes hard, right? Then I tried. Finance goes hard.
- [13:19]
Podcast Host
Then.
- [13:20]
Chris Cunningham
Then I tried, you know, sales goes hard. So I just made the same guys. They were HR guys or sales guys. I just kept bringing different departments. Cause that reached a different audience. So then we did it. So now we're doing the same proven formula, but with a different audience. Now the other thing we did is then we said, okay, what if we did different music genres? So sometimes it was the 90s for millennials, but, like, that's what we think about, right? But there's also the 70s and the 80s of music. So then we pulled music from different genres, and that did really well too. So that allowed me to really get the most juice out of the squeeze. And that's why I think most people mess up is they don't capitalize when they found that hit. But here's the other way you can mess up. If you're just creating A's and you just create that same piece of content, eventually you will Run out of juice, people will get the content will get exhausted. So you need is to look for B's. That's where you look for other things that are working for other people. And you find a way to do it your way. And then Cs are trends. Anytime there's a trend, jump on a trend. If you can and you can add value to the trend, you should do it. It's quick, easy views. Don't do only trends. That's how you fail. And then D. D is my favorite, favorite part about content, Daniel. And it's, it's experimenting with the unconventional. Try something new, do something knowing else has done. Go be unhinged. That's another thing people love, especially on TikTok and Reels. So what I do is I have a formula. So each week we're going to do around, you know, six to eight A's, because we know they work. It's our highest, highest hit probability. Right. We have a science behind this. So we hit A's, then we do B's. Maybe like 2 or 3 B's. Cause they still have a pretty good chance of hitting their maybe four because they're proven C's. We just do like once, whenever a trend comes up and then Ds, we try to do one brand new thing a week and that might get our lower views, but every now and again you'll strike gold with the D and it becomes an A. So your goal is to keep creating different content that becomes more A's. But while you're using the A's, being smart enough, notice when they've kind of exhausted and you need a new piece of content to sub in.
- [15:06]
Podcast Host
Yeah. And I feel like a lot of the D, like not a lot, but like a portion, maybe 10% of the Ds become A's. And you know, they just, if you didn't do the Ds, they wouldn't have been A's at the beginning.
- [15:17]
Chris Cunningham
There you go. And then if you never. And if, if not, your A's will get like, people will get tired of your A's. Like I can only do this dancing HR guy. It's still working somehow, but eventually it'll slow down. But that's cool. Cause I have other things that work now. Yeah.
- [15:28]
Podcast Host
And it's also, I feel like some things that you said with what you were talking about is there's a lot of proven models just not on social and not in, in other industries, in other formats and other ways where you could do things that are funny but haven't been brought to your industry. So there's like, like, I think the. A lot of the A's are things like people have done funny skits about sure things in snl, but they haven't done it about hr. So let's like see if I could do an SNL type skit on it about hr. Like the bees. They are things that are working for that industry that has nothing to do with me or that greater. But if I just switch it into me, that's like kind of a lower lift because it's already on social. The A seem to be like things that have, like, worked on, like TV or like some other realm or even something just worked for you, you know, and then. But it has originality to it too, because I feel like a lot of them are not exactly. I would not say that you're copying any of these things. It's more. I know that funny improv type skits people like.
- [16:43]
Chris Cunningham
Yeah, they love it.
- [16:44]
Podcast Host
Like, let me just make some type of improv skit that will work for me in a different way, in an original way. And let's see if it works.
- [16:53]
Chris Cunningham
100%. 100%. That's the formula. And if anyone else follows it, it will work.
- [16:57]
Podcast Host
So A, B, C, D. So that you have this. You have this science broken down. What is, what have you figured out is the science of a good video? What is a breakdown of a good video? What in your perspective, what makes a great video on social.
- [17:15]
Chris Cunningham
Yeah, what makes a great video for me is. Well, number one, if it's relatable, if it's shareable, if it's contagious, right? So it's something I see and I automatically want to hit the share button and send it to someone that that means it's gonna be a good video. Two, if there's something really cool, you can comment. You, you might make a great video, but there's not much to say about it, right? And if that's the case, the need of it is that great a video, it might not go as viral as it could because there's no reason to really comment on it or engage with it. Number three is one that everyone says, but it's not as big as it used to be as a hook. So your hook and then your headline, like having a really good headline can actually really make the difference of a video because that's the first thing people see. Like it makes it. Is it worth my time or not? They see the headline like, pov, you know, you just started a new job or something. Like that you get the right headline that's relatable or funny enough to make them want to see the end that'll hit too. Fourth is pacing. You know, is there a part where it gets boring? Does it, does it keep your attention throughout? And then the last is, we call it like a button. Is there something that just makes it end so well that maybe you want to watch it again or you just feel pleasant afterwards? Right. Like, is there. Because sometimes you have a great hook and a great body, but you just don't end it well. Just it doesn't end how they want. And then that kind of messes up the video. So I think you need those five things to really be a successful video. And the biggest ones are making sure you, you have something in there that makes someone want to hit share, that makes them want to hit the group chat. Right. I think Mark and Millennials does a great job of that. You know, like, you see, you see that in WhatsApp groups or in slacks all the time. You guys have a cool post, they go share it. And same with ClickUp. Like, they're like, oh, this reminds me of, you know, Joe at work. Or that's why I make like a video making fun of the IT guy. A lot of people probably send it to their IT guy or the IT guy sends it to his IT friends. Hey, this is us. That's, that's what makes a great video to me in B2B.
- [18:52]
Podcast Host
Yeah, I think I, I, I said this actually I'm, I wrote a little bit post about this. But I think if you, the number one thing I think about with any social is, is like op optimize especially for like ins, like these social platforms. Instagram, for example, if you can get into the DMs or on in the stories or to Slack channel that metric. I always, I look at that, that share metric more than it. And if I get more, I try to beat the likes with the 100 shares. That's my like goal is like there you go. Then that's how, that's how I know this is hitting for an audience and I'm going to keep doing that idea is more people are sharing. The like thing is like just signal. It's not but share is someone had a deep reaction. And I think one thing social does really good and I think this is what you, you probably are looking at is you could tell video drop off really well now on platform. So if a hook's good and then they drop off, this might be something in the middle and the Hook's good and like it's trailing and then there's a deep drop of the end something bad. You could tell where in your video you are missing which is so useful crazy at this point.
- [20:13]
Chris Cunningham
Yeah, that's what's so valuable. That's why too many people give up on a video. Like I made a video just the other day that we thought was really going to hit and it didn't. And I was like, you know what it looks like people dropped off here. We messed up on this. So rather than just giving up on the video, I'm going to go re edit it, I'm going to post it again because very few people saw it. Right. So never give up on a good concept when you think you can find the problem and fix it too.
- [20:32]
Podcast Host
And I love on Instagram now that you just could trial to non trialers so you're not. You're non. Your non followers don't even see your followers don't even see what you're doing. And then you can flop all you want to non it doesn't matter which is a great feature they have smartest.
- [20:48]
Chris Cunningham
Feature they've ever added. It's been huge for us. We won't post a video without trying dryer wheels first to know I know.
- [20:53]
Podcast Host
You you we talked about this before you got on. But what are some things you're testing now trying? What are things you're figuring out that are are working for you and going into 2026 and what are you you're thinking about?
- [21:07]
Chris Cunningham
There's a lot of new things I'm trying And you know one is these like creator led like new pages. So you basically get one create. I've seen lovable base 44 a lot of these pages doing it. Even cluly you get like one person and they're just creating a video daily. And the video is not really an ad, but kind of an ad. So you're basically like teaching something. So let's say it's like dev tips with Chris. And in these dev tips I'm giving out dev tips but usually in one of them the tip uses the product of which I'm pushing. And so it's just getting a new audience every time. And you're basically betting on like of the 30 videos they make three or four go viral. Right. But with that you still get a pretty big audience and from someone that's not your brand, not on the brand account, it has a higher way to reach. So I call those like creator led pages. Secondly EGC, I'm all in on EGC employee generated content. I have like 15 of my employees creating content now and 5 of which are doing really well. You know, 20k plus followers and the rest are coming, we're getting close to 10. I think it's just a great way to make content, especially on LinkedIn. That's where I care about the most because right now everyone wants to learn. No one has time to go back to school. So the best way to really learn is by being on LinkedIn. And let's say you're a sales solutions engineer, you're going to learn from another sales solutions engineer at a company you respect, right? So that's why Liam, one of our best sales solutions I have him creating content. What makes you so good? Why are you so great at your job? Just speak about it, just talk about it. People want to know and he does that and he's getting great engagement now and starting to grow and that's just one of the many examples. But I'm really, really high on egc. The next thing I'm high on is I'm thinking about the next level. I think that this creator led brand thing that I have is, is great and short form is great, but I think there's going to be some long form. I think there's going to be companies making short movies, short films. There's this new thing called real short where it's like minute long episodes of seasons. I think content is going to evolve and I think that brands need to be on the forefront of it by really treating themselves not as a full media company, but making sure they have some type of consistent media that they know they can bring in new eyeballs and keep attention. Whether it be education, funny like me or just teaching people something, just making them better at their job. If you can't do one of those three, you're probably not going to hold their attention when they finish their workday and they pull out their phone and you got to be there somehow.
- [23:23]
Podcast Host
I think the one good just going back to the first thing because I think people probably going to miss a lot of what that actually is. A lot of people only invest in their brand account. So like ClickUp investing ClickUp or ClickUp Investing. But you're saying you're investing in other pages that are adjacent or part of clickups like Media Hub that are doing tetra ClickUp maybe comedy for ClickUp and they're just generating views on the side but they all directionally part of the ClickUp universe. But it's not all going on the brand account because you can. Some things you can't post on your brand account. So you have other pages where you're, you're growing it on the side. Is that, is that what's going on? Is you creating multiple accounts on multiple platforms?
- [24:15]
Chris Cunningham
You nailed it. So what we're doing is I have ClickUp page, right? But I have ClickUp Comedy. I have ClickUp on the street, ClickUp Memes Tips with ClickUp. Right. I have all these different pages. But the way that you bring it together is the beauty of with Instagram is I can have these different pages, but I can still sometimes joint post it with ClickUp. Right? So I can say a joint post with ClickUp and ClickUp Comedy or a joint post with ClickUp and ClickUp Memes, but then you grow your own page. So the ironic thing is ClickUp Comedy might pass ClickUp's main page and followers. I think people love the comedy page so much and that's how I've been. It's proven to me that we were right to bet on comedy because this ClickUp comedy page has like 340,000 followers, whereas I think ClickUp has 400k. Right. So it, it might. And it's growing faster. It might surpass. But now I can still use ClickUp as that one anchor to still joint posts with ClickUp Comedy, joint post with ClickUp Memes. And so you can still go on our page and see a mix of all the different pages we have. But it's better to have the separate page and keep that separate audience because not everyone wants to follow ClickUp but they might want to follow Tips with ClickUp or Click on Memes, that's fine. But it's building a big ecosystem that all still goes back to one place, ClickUp and are still very well branded.
- [25:19]
Podcast Host
And I think, I think this all stemmed from the early signal was okay when you first started. I'm going to get a bunch of creators. I'm going to use attention from their audience. Now we've grown our audience. Like can we be the internal exact creators where, where media pages are some of the creators. Not technic creators, but sub pages. And then employees are sub creators too because they're part of the click of universe. They're just different characters in the. In the universe.
- [25:55]
Chris Cunningham
Exactly. With and get. We're engaged with all of them. So on Instagram you can joint post. On LinkedIn you can like and repost, right? So we're just making sure we repost everyone's stuff. So ClickUp is the main base. We're helping grow these other big audiences as well, which is great. And then at the same time, sometimes I lean on other creators. So I might go like, I might say, hey Daniel, with Mark Millennials, can we do a joint post? Can we engage us together? I get other creators like Joe Fendi, Fried Chicken, Corporate bro. Right. We've worked with, with, you know, major creators like this and then we tap into their audience, we join post with them and then. And our audience also sees them. So it's kind of a. I'm glad that we can always be a win win and help new audiences find them too.
- [26:31]
Podcast Host
Yeah, I think that, I mean join posts are one of the best things that happen done on Instagram because I've done a couple of the marketing Millennials where like me and corporate humor did a joint post and we, we like 3x posts just because we did it. We just shared similar ideas, but we both collabed on the ideas and it just took off. So I think finding ways to collab with other audience relatively your size or if you want someone bigger, obviously pay to play with.
- [27:02]
Chris Cunningham
It's a good play. It's anytime you can do eyeballs, it's a good play. But you gotta have good content to make sure you still get the followers and the ROI on it. Yeah, that's.
- [27:09]
Podcast Host
I think let's dig into that a lot because I think some of people are doing this, the Instagram play, some of them are, oh, like trying to do the Instagram break, trying to do the TikTok play, trying to get, do all these plays. But I think the biggest problem is they, it comes down to not doing what the platform wants or not doing what actually works and is shareable, which we talked about before. And I think a lot of times people come to me and say, why is my LinkedIn not working or my Instagram not working? It always comes down to looking at their content and being like, would you share this content? Would you? So I think how do you teach people internally to start selling what you sold at ClickUp? I know that the testing the idea is one thing, but let's if you could tell, tell someone to start small today just to get their feet wet and doing this, what would you tell them?
- [28:05]
Chris Cunningham
This is exactly what I would tell them to do. I would tell them to go start looking at content they enjoy. So looking at content that they feels like, feels like matches their brand. Right? For us at ClickUp, we like to laugh. That's why I thought this would make sense. And we thought the business world was a Fun thing to make fun of, fun of that would still come back to us. So what? I would challenge any person out there who wants to create a content strategy, their company, but is having a hard time. I would say first look at the ethos of your brand and choose one of these three ways where you're gonna make people laugh. We're gonna teach them something, we're gonna add value. Right? So what is that? Is it creating a news station for your or like a news page for your space? Is it creating, you know, like a course or creating like a free, a free masterclass to be better at this job for your icp or is it making you, making your ICP laugh? Is it one of those three? Figure it out, then start testing. You can still test all three if you're not sure which one it's gonna be. But then you just gotta start testing. And the way you're gonna do that is the most low cost way you can is you're going to scroll through social media. You're gonna scroll for some time and you're gonna find a couple creators you really like. But they're not big yet. They've got 15,000 followers, 22,000 followers, 6,000 followers. But they've had at least one to two videos that have hit meaning like a 200k or a million. So they've learned the algorithm, they've had success, but they, they're not perfect at it yet. And you're gonna reach out to them and say, hey look, I know many companies are not reaching out to you for brand deals yet. I see something in you, I think you can do something great, let's work out a deal. I don't have so much budget for this. Cause I need to prove to the higher ups that this will work. Because it's exactly what I did. And you say, okay, let's work out. Maybe it's 1500amonth, maybe it's 2200amonth and you're gonna make 15, 20 videos for me. So we can at least post three, four days a week and get some traction and see some success. And you could do it with one or maybe two creators, have them both kind of, you know, battle it out, but get some and then start posting these videos and start looking for signals. So when something does bad, mark it as red. When somebody does decent market as yellow, maybe try it again with a new edit and change it up. And when something is green, you congrats, you found an a20k, 30k, 50k video. Now recreate those as Many times as you can. And then from there, once you have a video that hits a couple times, you find some consistency with it, you find a formula. Then you go to your board and say, hey, I got 10 million impressions for us last month. What is that worth to you? And they say, oh, 10 million impressions. You know, we pay X amount for that. Okay, why don't you give me that? I'm gonna get it worth organic. And then we can bring our CAC payback down with our ads. We can have more of a brand and I can get better and better at it, make this cheaper and cheaper. And that's what they'll do. So they'll say, okay, now let's give you 4K and see if this creator creates 40 videos. How will we do? That's what you do. You start small, you find a creator, you find a formula, then you find a creator at a pretty good cost. But you bet on them and say, but look, once we make it big, I will pay you more because you should. As they start adding more value and you try to lock that creator in full time. Because other people, if you don't see their value, others will. And trust me, many people have tried to steal and take my creators. That's why I have to properly incentivize them and take care of them.
- [30:55]
Podcast Host
I think what you also said, which is which, I think the part I was going to ask you about is how to sell it and how to sell the revenue side or what you're doing. I think one where you said impressions, we pay for a CPM of X amount on Facebook and Google. If we do that on, on social, how much is that worth to you? And then, oh, this is trickling down to this metric. To this metric. I think selling it like that because what people don't get on like Facebook and they are guaranteed impressions. But guaranteed impressions doesn't mean guaranteed eyeballs. It means guaranteed that it's going to show up in someone's feed and someone scrolls past it.
- [31:39]
Chris Cunningham
Exactly. Doesn't mean they cared about it.
- [31:42]
Podcast Host
So if you could create content that does that and then reverse engineer, what they care about is, okay, we get 10 million impressions. That's how much. This is how much it costs in social. Look, when we get 10 million impressions, CAC payback goes down. Cost to acquire a customer goes down. People know about ClickUp more. All these metrics start going in the right direction. That's how you sell it. I think that's perfect. I wanted to ask you too. How are you thinking about AI content using AI and social in 2026.
- [32:13]
Chris Cunningham
You know, I don't probably have the, the hottest take on here. I, I'm still in the camp of I love AI. I use AI all the time. I don't think you should fully automate your content with AI. Like, I'm, I'm not the believer in that. I don't think it writes the best content. I don't use it for my scripts. I might use it for ideas here and there. But, you know, everyone's saying, oh, AI is just going to make every video okay. I, I don't see it yet because I still think right now people want creators. They want like genuine human. If anything I've seen that requested more like, they still, they'd rather see a lot of AI videos don't perform right because people, they know it's AI and they want to keep scrolling. However, I do think there's a lot of good things you can do with AI. I've created an AI meme page. I think that's pretty good. I think you can still make some funny quick memes, images, videos without putting too much work into it and have some success with some thought. So I do believe in those. I do believe in still creating. Like I posted an AI video the other day for ClickUp. I still believe in like making AI videos, but I don't believe making it your whole strategy. And I don't believe handing over the keys to make AI do everything right. I write the scripts, I make the video. I'm not saying it'll never get there, but for now I just don't think that's the case. And I think if anything, people are screaming for more real. Like they'd almost rather you just walk out and talk on your phone than seeing some AI video or some highly produced video. Because right now they're just, they're not in office with people as much anymore. They're craving something real and hearing like real conversation. So when you look on TikTok, when you look at Instagram or more the Talking Head videos, it's more just someone being real and just sharing real thoughts that AI can never pull out together. Just thoughts straight from the brain. So that's a lot of beauty in it. So my advice to everyone is still make sure you use AI. Like streamline things where you can automate, where you can get ideas from AI, where you can build out plans and use it to track your data where you can. But I would not lean on it completely. I would not have it write all your captions exactly Maybe use it and start it that way, but I just don't think it's there yet. Yet. But make sure you're still playing with it. Make sure you're still using every day. Because you also don't want to be that person caught behind. If AI does start really working in content, you need to make sure you understand it.
- [34:16]
Podcast Host
Yeah, I think that's the best way to put it right now. Understand why it works, how it works, how to do it. But I do. I'm in the camp also is there's some human things that AI can't replicate and some like this humor that hasn't been told yet that human. Only humans could do the scripts that like, I feel AI doesn't have taste yet. I would say it's only if you, if you feed it taste, it might give you taste. Like, hey, here are all my videos. What is the common thing that's going on here? Maybe they come up with something that is trending.
- [34:53]
Chris Cunningham
There you go.
- [34:54]
Podcast Host
But you are. You're the input, not the. You're. You don't make yourself the output of the content. You're the input. And it's trying to analyze what you're doing, not what. Asking it. How to make a viral video.
- [35:06]
Chris Cunningham
Exactly. That's a good way of saying it.
- [35:08]
Podcast Host
I want to ask you a question that I ask everybody in this podcast is what is a marketing hill you would die on?
- [35:16]
Chris Cunningham
A marketing hill that I would die on is that most companies die in marketing or fail in marketing because they get too, too caught up on, like, attribution. They get too caught up on seeing immediate results. You always lose to companies like us who don't do that in marketing because it takes time to see some of these results. And it's not to, like, make marketers lazy or anything. They should still be held accountable. They should still definitely be bringing in revenue. But those who are too afraid to try anything, those who are just going to follow the same playbook, those who will just do something that brings them immediate roi, like Facebook ads they'll only get. But so far, because I told you, it took me three or four months to really start even seeing great results from this plan. It took me maybe seven to nine months before we had a big deal close and say, hey, we found you because of your TikTok. Right? But it still happened. And there's still many more that it's happening that we probably don't even know about. But it took almost a year before we started becoming the brand that everyone's talking about. Oh, ClickUp is the gold standard for content. I only got there by breaking this so called rule of like we need X amount of leads and X amount of eyeballs from every piece of video you make. If luckily my CEO Guarav was cool and, and let me run with this, luckily our CEO Zeb understood and saw the vision because now they love that every conference we go to, oh, I love your brand. Oh, I love your marketing. You know, like that that is priceless and that, that puts you in a different category. That's a moat. That means people are always going to know about you. Right. But you will never get to the levels we have, the views that we get without being prepared to maybe not have ROI for a couple months. Exactly. And not be able to see it. That's the beauty of marketing and it's also the toughest part of marketing because I also still understand those people who are very numbers oriented. I do, I'm very numbers oriented myself. But you gotta take risk. Like everything in life, like every big founder, you know, you gotta take some risk and that's the risk of marketing you're gonna have to take. So the hill that I will die on is you can't just overly track attribution immediately. Last click all that. You gotta just take the risk, keep going, keep iterating and believe that it will come together. The, that's the only way you're going to get there.
- [37:12]
Podcast Host
And you said it, you said at the beginning, I, I think we just reiterated that you don't, you started off with a, a very small budget and the budget kept growing as you started proving results and that's why it's working. But you, you had this test budget to, to do an experiment and then show that. And I, I'm in agreement on that. I think even in the age of AI this is even more important, this brand stuff because the way you get talked about at AI is you get showed up in a lot of places because of your brand. And if you don't have a brand, paid social is not going to get you AI views because nobody cares about your brand on paid social. But if you are doing fun things, shareable things, seen as the best content, people are going to talk about you more and more and that's what the LLMs are going to see and you're going to get fed and people are going to, your brand is going to pop up more and more in the age of AI as well. So lastly, where could people find you? ClickUp, all that good stuff.
- [38:11]
Chris Cunningham
Yeah, yeah, ClickUp's Pretty easy to find. Just at ClickUp you can find any of the other pages. ClickUp Comedy. If you haven't seen any of our videos, I'm biased, but you should check it out. I think we're definitely doing something different and we're doing something fun. For me, I'm just at Cunningham, my last name as you see down here on Instagram and just Chris ClickUp on Twitter and LinkedIn. I'm another fair millennial, always creating content. Very easy to get in touch with chris@ClickUp.com if you have any questions, if I can ever help. I love helping this. I love supporting the community, I love marketing and I want to see everyone win. I know how tough it is to win. That's why I'm glad we have people like you, like me, who are just out handing out the secrets as much as we can. So the marketing world can be better in B2B.
- [38:50]
Podcast Host
Yeah. And I think that's that, that's the key of winning is, is adding something to someone's day or adding someone to some, someone's job or adding something that can make someone better. So I think go out today and with your brand, do something to make someone better their job. Smile. Do something that someone will do and that your, your marketing will work. If you do, if you think along.
- [39:13]
Chris Cunningham
That 100, if you're being unselfish and you're just wanting to go share and give, it will win every single time. And yeah, Daniel, we're both in Miami so we need to hang in person soon. I've been traveling so much, man. I know you just had a new kid, so my father will definitely hang soon.
- [39:25]
Podcast Host
Talk soon.
- [39:30]
Daniel Murray
Thanks so much for listening. Keep tuning in to hear more great insights from the coolest marketers from around the world. If you haven't already, make sure to subscribe and follow the Marketing Millennials podcast on Apple Podcasts, Spotify, YouTube or wherever you get your podcast. And if you like what you hear, I would greatly appreciate you giving us a five star rating. It helps bring more marketers into our community.