SPECIAL GUEST!! ClickUp's Co-Founder Chris Cunningham 💸 The $1,000 Content Hack Big Brands Miss | Ep. 532

Jay Schwedelson: We are back for Do This Not That, and I got a guy here who's got more energy than I do, which is weird because I drink way too much coffee, but he's a legend. He is a beast. He's one of the best dudes I know. So who's here?

We got Chris Cunningham. Now, you may know the company that he was one of the founding team members of, which is ClickUp. Chris doesn't know this, and this is not a commercial. This isn't a paid thing.

I use ClickUp. My business use ClickUp. It is awesome. It is this AI-driven project management productivity platform that honestly, if I didn't have it, I would be screwed.

And it's not just some, oh, some small little SaaS. There's always SaaS companies out there. They started this thing in 2017. It is valued at over $4 billion.

That's a B. This is ridiculous, and the reason Chris is here, other than being a great dude and crushing it, he's the secret sauce about how ClickUp broke through a pretty crowded category, and they used a lot of organic marketing tactics to actually grow this business, which is almost unheard of in the world of SaaS. So I can't wait to dig into all this with Chris 'cause he knows what's up. Welcome to the show, my man Chris Cunningham: Man, I'm ready to be here.

So glad we met at a, an event, what, in San Francisco a little while back, and now here we are. Jay Schwedelson: Here we are. Chris Cunningham: I didn't even know you used ClickUp, man. I, I gotta hook up your account, especially that, uh, that intro.

I gotta hook you Jay Schwedelson: right? Like, we'll make it, that's like an infomercial right there. Chris Cunningham: I feel bad I'm charging you Jay Schwedelson: Yeah. Thank you.

All right. So let's get into it though for a second here, because what I said is true. I watched how you guys took this thing organically, and I know that you were pulling the levers. How did you get it all going?

How did you break through organically? Chris Cunningham: You know, it took a little bit of, uh, of a little bit of a craziness and a little bit of belief from my board, 'cause imagine me going in and saying, "Hey, look, I got this idea. We're gonna get a lot of organic impressions. I'm gonna have two grown men, you know, twerking and dancing and, and being crazy on social."

When I pitched this to the board, they, they believe in me, but they weren't so sure at first. But I was like: Look, I always win for us because I watch B2C. That's been my playbook the whole time. It's not that complex.

I used to work in B2C. I ran content and influencer marketing for Celsius, for Fashion Nova, a lot of big campaigns in the agency prior to ClickUp. And so I told them, "Look, you saw what I do with influencers. I was ahead on B2B with influencers because that's what B2C did."

And so I saw some things happening in B2C. I saw people making these, like, TV shows and getting, like, more consistent with their content. And I saw this new app in China called ReelShort where people were, like, almost making mini TV shows. And so I took a bet that that's where the future's going, and I wanted them to take a bet with me that every company will have one in-house creator, at least one, that creates content for them consistently, because there's not...

With so much attention out there, everyone's on their phones now. So it started like this. Like, Jay, I, I basically was like, "Look, I know you, I know how ClickUp is. You're not gonna give me a ton of budget to try this.

I'll be scrappy. I'll prove it to you." So I was like, "Just give me - Let me just get one contractor, one creator." So I found Luke.

I'd been stalking Luke for a while. Luke is the guy in the blue shirt in our famous HR guys video with the kinda gray hair. Hilarious. He's kinda the Will Ferrell of our acting crew.

And I was like, "Let me just start making videos with him." And this is why I think most people fail in marketing, because the first month we did together and we had no, you know, not bad, but no big hits, 20K, 30K. But we were learning. We were taking data.

We were being very scrappy. And every Friday we were analyzing, "Okay, this is what worked, this is what didn't. Let's double down here." Second month, we had a maybe three or four videos hit a million.

Now the company's interested. They see a couple million impressions. They know what they pay for it. They know what I'm paying for this.

It's way less. "Okay, can we ramp it up?" The third month, that's when we really hit some... I think we hit 25 million impressions in a month, and that's when they were like, "Okay, how do you hit 100?"

And from there, they gave me a little more budget. I hired a second actor, and that's how this was really born. What was born was the best way everyone should do marketing. Do small tests, show some signal, then go back to your CEO and ask for more budget.

That's, that's always been my playbook. Jay Schwedelson: Okay, so now if I'm listening out there like, "All right, uh, I can't go to anybody and hire a- an actor in LA and, and do all this crazy stuff," is there a version of your playbook for that, you know, small to mid-size marketer out there that's like, "I wanna do something. I do wanna break through"? Like, how can the regular company that doesn't have Chris Cunningham there, uh, uh, still break through?

Because everyone just going out there and be like, "Okay, we have a webinar. We'll put two circles of people's heads and promote it." What can people do to kinda break out of their shell if they're not able to do, ever go as far as you did? Chris Cunningham: Of course.

And what, what I think you could do small is, one, you could try to find an up-and-coming creator. You can find, like, an influencer who maybe has 6 to 8,000 followers, 12,000 followers, 20,000 followers, but they're not getting paid a lot yet. And you can say, "Hey, look, I've seen you had one video hit. You've had a..."

Look for someone who has a small following, but they've went viral a couple times, right? 'Cause it takes - To get a big following, you gotta go viral a lot or you gotta be very consistent for a long time. But you'll find these creators that, that, that hit, they just figured out the algorithm, but no one knows them yet, and you need to jump on those. I, I feel like I'm a master at finding them.

I can name 10 more right now. Steven Kono. Uh, I, I can keep going. I keep finding these all the time.

And that's one way. Or you can still copy my playbook. I don't hide it. I put it on LinkedIn, it went pretty viral.

You can go to, uh, backstage.com and you can, you can hire an actor. You can find one for, like, you know, pay their day rate. There's a, there's a SAG rate.

It's not too crazy. And it's, like, you know, 400 bucks and you can pay them for the day, uh, and just ask them to shoot for you. Make as many videos as they can. Uh, you can, you can pay someone else to shoot with a iPhone, another two, 200 for the day, and now you've got eight to 10 videos for under $1,000, right?

Now, this is a very scrappy version. If you wanna get it consistent, now you gotta work something out with them, and you gotta keep, you know, hiring them. But the key is, is the day rate. That's the big difference that I realized with actors from influencers.

For influencers, I pay for a video. I pay for usage rights. For actors, I pay for the day, and then they go create, and what, what, what, what we create is what I own. So that was, like, the big arbitrage that I saw.

So I don't want anyone to be held back. And in the beginning, I was acting in a lot of the videos, right? I, I quickly realized I wasn't as funny as and, and talented, but it, I - but we still hit millions of views with me in the video. So I think, like, having someone who's ready, either finding one creator or trying to go online, go to LA, book, shoot the videos Jay Schwedelson: And, and when you're getting all this organic traffic, because you weren't selling, uh, you know, sneakers, you were selling, no offense, a relatively boring SaaS product.

It's great, don't get me wrong, okay? But it, you know, it's a boring SaaS product. How do you go, okay, you got this funny, uh, uh, video that's getting a couple million impressions to getting demos or downloads or trials? How do you make it, how do you make the math work?

Chris Cunningham: Yeah, and that's what took time to figure out too. So once it started getting the views, sure, we saw, like, we saw a mass influx and, like, uh, and, and people trying to work at ClickUp. I remember HR team was like, "Dude, I don't know if we can handle all this 'cause now everyone wants to work here." 'Cause they, they thought, like, what we were creating was real, like it was really happening in the office every day, and like, "I wanna be at, at this company."

But then you gotta fi- figure out downloads, right? Otherwise, my CEO would cut me off and would never give me more budget. That's where I had to get scrappy again. And luckily, I, uh, I've got a couple ways of doing this.

One, I put, you know, link in bio, and I put unreleased content here. So there, people can go and see more videos. They become fans. They love our content.

But when they go to this page, what it really is there is unreleased content, but also is a video from, from our, from our actors, our main acting crew, just saying, "Hey, look, we love doing this for you. We wanna keep doing it. But the only way we can keep our jobs is if you book a demo. ClickUp's really good at saving time.

They're really good at project management. They have AI in the project management. Check it out below, but here's also our funny videos." So we, we do that.

That's one way, and we g- we get tons of, of site visits and, and traffic there. But the real way we've turned this into pipeline is now I started working with my sales team, and I said, "Okay, look, there's tons of good people watching our content. We need to figure it out." So I met - One of our c- one of our customers is, is VaynerMedia, and, uh, there's a guy named, guy there named Steele, and he, he built a product.

I don't even know if he's fully released it yet. Uh, but he built a product that allows me to give him the data from my Instagram, from my TikTok, and from my LinkedIn, and we're seeing every single person who's engaging with our posts, how much they're engaging with the posts, how long they've been following us for. And it can't find all of them on Instagram and TikTok, most on LinkedIn, but it can find a decent amount of the percentage of their jobs, who they are. So I figured out that the COO of McDonald's was following our page on Instagram.

So what did I do? That's one of the biggest accounts we could ever get. So I took the actors, we made a custom video for them, ba, ba, ba, ba, ba, something funny with McDonald's, right? And we sent him that video.

And from there, then we have a demo set. Nothing's closed yet, but where else would I ever get an in with the COO of McDonald's? It was from our content. And so that's the pipeline that we've built now is we're checking every single two weeks.

We're seeing who the new followers are, who's the most engaged, who's commenting, and if there's... And it, it automatically pulls what company they're at, what size it's at. And so if we see a signal of someone's in a 500-person-plus company, we're making a custom video, and we're saying, "Hey, look, we did this for you. So glad you love our content.

Take a call." Like, I don't care who you use now. I don't care if you have six months. Just meet us, know us.

We're a good product. We ship fast, and we make content you like Jay Schwedelson: You know, it's funny you say that, and it's something I need to do a better job of, is you'll see, like, all these people liking posts or whatever, and they'll be important people, and then you won't, you won't take the time to realize that it's maybe the same important people that are interacting with your stuff and then reaching out to them and being intentional about that. And I think that just a...

Listen, you know better than I do, a handful of accounts can change the trajectory of your business if you're just intentional about looking under the hood a little bit about the people that actually are into what you're doing Chris Cunningham: That's, that's the biggest part people mess up on, right? I think, I - and, and they wait for a lead magnet or something like that, but you don't have to wait. Like you can just... There's literally, you can use Zapier.

There's all kind of automations, like with LinkedIn, you can use Zapier and just say, "Hey, anytime a person over X amount comments, put it in my sales funnel." You know? Add it, add it straight to Salesforce. These things are, especially with AI now, it's easier now than ever.

So I agree. I think you cannot miss out on that, especially if you're putting time and money into your content. And those who aren't, you should look into it because it's a, it's a brand new way to reach. You can only make but so many dials and cold calls.

This is fun. It's, it's really working well, and our sales team enjoys it 'cause it's a much more warm way to, to be introed Jay Schwedelson: All right, now I wanna switch gears because, uh, this is a golden opportunity for me to ask somebody in your seat about what the hell is going on in the world right now, and I'm just, I'm just curious about what your take is. So here you are, you are one of the founding team members, one of the leaders of a, of a, you know, multi-billion valued SaaS company, and, you know, all the other, uh, software related companies, whatever tools that are out there, AI is gonna be the end of the universe.

And, and you, you... I love - You're a very opinionated dude. So what is AI mean to SaaS products, companies, services like yours? Is it the end or the beginning, or what the hell's gonna happen?

Chris Cunningham: I'm super opinionated. I'm glad you're asking me this question. I, I'm also super positive, so maybe my answer is, is, is the positive and... But I, but I see both.

Look, here's the first thing I'll say to you. I mean, when I graduated, you know, the internet was, was hot. I think I graduated, what? In 2012 from college.

Before that, like 2007 in high school, internet was becoming a big thing. Everyone thought internet was gonna take all the jobs, right? But look at all the jobs we have now. All these jobs were created from the internet.

Now, I'm not saying AI is not going to take jobs. I'm not, I'm not... I would never lie and say... AI is going to be taking certain jobs, right?

But I think the goal of AI is to take aba- take away the busy work, take away the work we're not supposed to be doing. That is, that is how I feel about it overall. Uh, I do think that companies are gonna have to adjust. When you go into software, I don't think it's the death of all software, but it will be the death of some.

It will be, and it will create more entrepreneurs from that. We've already saw there's 4,000 engineers from Block that are looking for jobs now, right? There's not gonna be all these jobs. What's gonna happen when - And then the signal that came after that was positive from the stock market.

So other companies are going to do this. We need to be ready for that, and, and AI does do a lot of the, the work in coding. But with that being said, I think there's gonna be way more entrepreneurs built. I think it's gonna get more competitive.

I think now if a software is not adapting, they will die because if, if your prices are inflated, if you're not shipping, someone else can vibe code it. Now, on the flip side, vibe coding is not what everyone thinks. Like, at the end of the day, you can vibe code a website right now in two seconds, but most people, 90% of people you go on the street and ask, they're still going to ask for someone to build their website, right? Like, same with software.

Like 90%, maybe even more, don't want to go build their software. They want to pay for it. They don't wanna deal with the back end, the, the paying the credits and, and all that. Um, so but it will get tougher, and if you're not good, you will be in trouble.

That's my, that's my overall look. I don't think we're, I don't think we're cooked as the, as the Gen Zs would say. I think we're, I think we're okay. I think we're gonna be all right, but we will see a lot of changes.

There will maybe be robots cleaning up snow. Maybe there will be Waymos everywhere. These things will happen, uh, but someone still has to drive the AI. Someone still has to make the thoughts and the decisions.

So I think we'll be okay, but I think we should be studying AI. I think we should still be ready in case. Jay Schwedelson: You know, I, I totally agree with you because, you know, is when, when Excel came out, Microsoft Excel came out, they said CPAs were gonna go away, and there's more CPAs than ever. Or, you know, Canva comes out, you're never gonna need another graphic designer, and there's graphic designers on every corner of, in America.

And, and, you know, to your point, uh, I think everything's gonna be AI adjacent. So even in, within ClickUp, are you guys bringing AI in in unique ways? Like, how are you looking at it? Chris Cunningham: Oh, massively.

So check this out. Obviously, we, we jumped on it from the get-go, and I, I give a lot of credit to our CEO, Zeb. You know, a lot of people told him at the beginning, "Hey, don't get too much on - Don't build too many AI products. It's, it's just a bubble."

And he, he knew. Like, he knew what this was doing. He knew the change. So we went in and, you know, we were the first ones to really launch full-on super agent.

We call them super agents, but agents inside the platform. So at ClickUp, we have about 1,000, I think around 300 employees, somewhere around there. We've got about like 6,000 agents that we've built. So it's almost like we have a whole wave of new employees.

And for those who don't know what agents are, I know that it's very easy in our bubble, Jay, to think everyone does, but not everyone knows what an agent is. An agent is more than just a chatbot. An agent, instead of just talking, it can actually do actions for you. So for example, I have an AI that checks my email now.

Like I, I feel like things are changing. I used to have to watch my email and make sure nothing urgent comes through. I don't have to do that anymore. Like an agent will tell me if something comes in that's a check for me or if it's like urgent, I need to act now, and the rest I just don't even look at.

So I, I really don't even look at my inbox feed the same. I let an agent bring it up to me and, and I respond that way. Um, so ev-everyone at ClickUp has agents, and we've built an agent studio where you can just build it. So if you haven't done it, Jay, I'd love to show you.

You can just go in and say, "Hey, I need an agent that triages my email," or, "I need an agent that gives me new ideas for my podcast guest," and it'll do it automatically. It'll run and do those tasks. So that's, that's our, our big AI feature, and we're definitely leaning into it heavy, and we're even making time to like study AI because we want everyone at ClickUp to be ahead and be moving fast. Jay Schwedelson: Dude, that is wild.

Uh, I didn't... I have to look at those features. I wasn't aware of that in Claude. Do you use AI in all aspects of your personal life?

I mean, like, I do. Like, I, like, chat... I, I asked AI, I asked Gemini everything. Do you do that?

Is that how you do your personal life? Chris Cunningham: Man, J- I'm, I, I would say I'm addicted to the combo of... I'm, I, I mostly use Claude and then Gemini on my phone. Like you said, if I'm asking something, I'm asking Gemini.

If I'm writing something or building something or... I, I use Claude, Claude and Cowork. I do, but now, now I will say this, not in content. Like, never have I ever used AI to, like, build a complete script end to end for me.

I, I just don't think it's there yet. I, I think that me and my writers and my team, we still crush AI when it comes to making funny content. I'm not saying that's gonna change, not gonna change, but as for now, that's what everyone asks, like, oh, you can just... When, when you see these posts that are very, like, trying to get attention, like, oh, use AI to automate and build all your content for a whole month.

I don't believe in any of that. I don't think it's there. I've tried. If it w- it'd make my life a lot easier if it did, but, uh, it doesn't right now, and the, the, the texts aren't that good.

The ideas are too generic. They're too basic. I might use it to generate some ideas for creative, but I'm still going to build it out. I'm still going to write the script because whenever someone brings me a script that's all AI, I can just tell, and when everyone writes a post on LinkedIn, I can just tell, and I don't wanna watch it.

I don't wanna read it, and I scroll right past it. And even AI video content, I'm testing it. I have an AI meme page, but my, my actors in that content is still crushing everything else because I think people can feel there's no soul. That this AI that built something, it's never experienced anything, and that's why we can't relate to the content it makes, but you can relate to a human.

You can still relate to, like, the get readies with me or a day in my life, or you can relate to the funny videos we do Jay Schwedelson: You know, it's funny you say that. I was - I saw Adam Mosseri, the head of Instagram, release this thing last week that said, uh, uh, uh, "Imperfections are really the most viral thing right now. If your dog's barking, leave it in the video. If you trip over the ground or if there's a fire engine, leave the noise going on," and that's what's actually working for organic reach is, is just, you know, just the humanity of it all.

And I'm like, it's just, it's just wild. This lo-fi stuff is, is where it's at. I mean, everyone, like, using AI for certain things like content would be the opposite of your playbook Chris Cunningham: It's, it's, it's funny, it's pure the opposite. And so many people come to me and they're, they're, you know, they have me speak on stage and they're like, "Okay, let's talk about how you use AI for all of them."

I'm like, "Well, I'm not gonna do that 'cause I don't." Right? I don't. But, but look, I, I definitely still use AI for things.

Like I, I might take a transcript and give it to AI and say, "Hey, where's the, the coolest moments? What's a good hook for this? Is this hook good?" But at the end of the day, I'm still choosing the hook.

I'm still choosing the text on screen, my team and I. Uh, we just, we just don't think AI is there yet. And, and again, when it's there, I'm happy to, happy to transition over, but I kinda like that it's not. I like that we can be honest and, and, and, and, and...

'Cause I think the, the thing that gets views the most for about a couple months now was saying AI does it all, but I think now everyone's hip to that. They know it's BS. So they'd rather you say, "Hey, look, AI does this for me. I'm still doing this."

And I think that's the beauty of what we want it to be. I want us to work with AI, not, not AI doing everything for us. Jay Schwedelson: Totally agree. Well, listen, you're awesome, my guy.

I love everything about you, love what you're doing. First off, everyone go to ClickUp. If you don't know them, you should be using them. I, I use it religiously.

It's incredible. We're gonna put Chris's, uh, uh, Inst- Instagram, LinkedIn, in, in the, uh, show notes here. It's Chris Cunningham. Chris, what else did I forget?

How else should people get involved in your world? Chris Cunningham: Yeah, LinkedIn, I'm Chris@ClickUp.com, and I'm @Cunningham on Instagram. Hit me up anywhere.

I'm always willing to help on ClickUp, and if everyone needs, if everyone needs any help with building out content or getting started, I'm happy to help. I love to help people out. I just love seeing good content and not all this AI slop, so hit me up Jay Schwedelson: Amazing. All right, man.

Thanks, my guy. Can't wait to hang out in Miami. See you Chris Cunningham: Yeah, we're right here, man. Let's hang out.

Sunny is beautiful Jay Schwedelson: There it is.