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

0:00Welcome to Do This Not That, the podcast for marketers. We share quick tips, things you can do right now, and then we add a little bit of chaos at the end of every episode. We also keep it short, like this intro. Let's check it out. we are back for do this not that and i got a guy 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 click up chris doesn't know this and this is not a commercial This isn't a pay thing.

0:39I 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.

1:23So I can't wait to dig into all this with Chris because he knows what's up. Welcome to the show, my man. Man, I'm ready to be here. So glad we met at an event in San Francisco a little while back. And now here we are. Here we are. I didn't even know you used ClickUp, man. I got to hook up your account, especially with that intro. I got to hook you up. That's like an infomercial right there. I feel bad I'm charging you. 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.

1:52How did you get it all going? How did you break through organically? You know, it took a little bit of a craziness and a little bit of belief from my board, because imagine me going in and saying, hey, look, I got this idea. We're going to get a lot of organic impressions. I'm going to have two grown men, you know, twerking and dancing and being crazy on social. When I pitched this to the board, they believe in me, but they weren't so sure at first. 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.

2:28And so I told them, look, you saw what I did with influencers. I was ahead on B2B with influencers because that's what B2C did. And so I saw some things happening at 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 Real Shorts where people were like almost making mini TV shows. And so I took a bet that that's where the future is 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 so much attention out there.

2:58Everyone's on their phones now. So it started like this. Like, Jay, I basically was like, look, I know how ClickUp is. You're not going to 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 kind of gray hair. Hilarious. He's kind of 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.

3:26because 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 will work. This will didn't. Let's double down here. Second month, we had 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.

3:55And that's when they were like, okay, how do you hit a hundred? 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 COO and ask for more budget. That's, that's always been my playbook. 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 small to mid-size marketer out there that's like, I want to do something.

4:27I do want to break through. How can the regular company that doesn't have Chris Cunningham there still break through? Because everyone just going out there and be like, okay, we have a webinar. We'll put two circles with people's heads and promote it. What can people do to kind of break out of their shell if they're not able to go as far as you did? Of course. And 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 six to 8 ,000 followers, 12 ,000 followers, 20 ,000 followers, but they're not getting paid a lot yet.

5:01And you can say, Hey, look, I've seen you had one video hit. You've had to look for someone who has a small following, but they've went viral a couple of times, right? Because it takes to get a big following. You got to go viral a lot. You got to 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 feel like I'm a master at finding them. I can name 10 more right now. Steven Kono. I can keep going. I keep finding these all the time. And that's one way. Or you can still copy my playbook.

5:28I don't hide it. I put it on LinkedIn and went pretty viral. You can go to backstage.com and you can hire an actor. You can find one for like, you know, pay their day rate. 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 and just ask them to shoot for you. Make as many videos as they can. You can pay someone else to shoot with an iPhone, another$200 for the day. And now you've got 8 to 10 videos for under$1 ,000, right? Now, this is a very scrappy version. If you want to get it consistent, now you've got to work something out with them and you've got to keep hiring them.

6:01But the key 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 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 quickly realized I wasn't as funny as I'm talented, 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.

6:31and 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 sass product it's great don't get me wrong okay super boring you know it's a boring sass 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 yeah and that's what took time to figure out too so once started getting the views sure we saw like we saw a mass influx and like uh and people trying to work at click i remember hr team was like dude i don't know if we can handle all this because now everyone wants to work here because they thought like what we were creating was real like it was really happening in the office every day like i want to be at this company but then you got to figure out downloads right otherwise my co would cut me off and would never give me more budget that's where i had to get scrappy again and luckily i i've got a couple ways of doing this one I put, you know, link in bio and I put unreleased content here.

7:27So there people can go and see more videos. They've become fans. They love our content. But when they go to this page, what it really is, there is unreleased content, but also there's a video from our actors, our main acting crew, just saying, Hey, look, we love doing this for you. We want to keep doing it. But the only way to keep our jobs is if you book a demo. Click was 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 do that. That's one why. And we get tons of site visits and traffic there.

7:52But 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 customers is VaynerMedia. And there's a guy there named Steele, and he built a product. I don't even know if he's fully released it yet, but he built a product that allows me to give him the data for my Instagram, for my TikTok, and for my LinkedIn. And we're seeing every single person who's engaging with their post, how much they're engaging with the post, how long they've been following us for.

8:20and it can't find all of them on Instagram and TikTok. Most on LinkedIn, 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, 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 as we're checking every single two weeks.

8:51We're seeing who the new followers are, who's the most engaged, who's commenting. And it automatically pulls what company they're at, what size it's at. And so if we see a signal, if 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. 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. 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.

9:20Yeah. They'll be important people. And then you won't take the time to realize that 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, 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. That's the biggest part people mess up on, right? I think they wait for a lead magnet or something like that, but you don't have to wait.

9:54You can just, there's literally, you can use Zapier. There's all kinds of automations. Like with LinkedIn, you can use Zapier and just say, hey, anytime a person over X amount of comments, put it in my sales funnel, add it straight to Salesforce. These things are, especially with AI, 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 brand new way to reach. can only make with so many dials and cold calls. This is fun. It's really working well. And our sales team enjoys it because it's a much more warm way to be intro'd.

10:22All right, now I want to switch gears because 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 curious about what your take is. So here you are. You are one of the founding team members, one of the leaders of a multi-billion valued SaaS company. and all the other software-related companies, whatever, tools that are out there, AI is going to be the end of the universe. And I love you're a very opinionated dude. So what does AI mean to SaaS products, companies, services like yours? Is it the end or the beginning or what the hell is going to happen?

11:04I'm super opinionated. I'm glad you're asking me this question. I'm also super positive. So maybe my answer is the positive, but I see both. Look, here's the first thing I'll say to you. I mean, when I graduated, the internet was hot. I think I graduated, what, in 2012 from college. Before that, like 2007 high school, internet was becoming a big thing. Everyone thought internet was going to 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 would never lie and say AI is going to be taking certain jobs, right?

11:35But I think the goal of AI is to take away the busy work, take away the work that I'm supposed to be doing. That is how I feel about it overall. I do think that companies are going to 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. They're looking for jobs now, right? There's not going to be all these jobs. What's going to happen when? And then the signal that came after that was positive from the stock market.

12:02So other companies are going to do this. We need to be ready for that. And AI does do a lot of 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 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 who go on the street and ask, they're still going to ask for someone to build their website, right?

12:29Like same with software, like 90%, maybe more, don't want to go build their software. they want to pay for it they don't want to deal with the back end 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 as the gen z's would say i think we're i think we're okay i think we're going to 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.

13:01So I think we'll be okay, but I think we should be studying AI. I think we should still be ready in case. You know, I totally agree with you because, you know, is when, when Excel came out, Microsoft Excel came out, they said CPAs were going to go away and there's more CPAs than ever, or, you know, Canva comes out, you're never going to need another graphic designer. And there's graphic designers on every corner of, in America. And, and, you know, to your point, I think everything's going to be ai adjacent so even in within click up are you guys bringing ai in in unique ways like how are you looking at it 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 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 decide to platform so at click up 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 j to think everyone knows what an agent is an agent is more than just a chat bot an agent instead of just talking you can actually do actions for you so for example i have an ai that checks my email now like i feel like things are changing used to have to watch my email make sure nothing urgent comes.

14:21I don't have to do that anymore. Like an agent would 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 really don't even look in my inbox feed the same. I let an agent bring it up to me and I respond that way. So 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.

14:47It'll run and do those tasks. So that's our big AI feature. 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 tasks. Dude, that is wild. I have to look at those features. I wasn't aware of that. Do you use AI in all aspects of your personal life? I mean, like I do. Like I asked AI, I asked Gemini everything. Do you do that? Is that how you do your personal life? Man, I would say I'm addicted to the combo of I mostly use Claude and then Gemini on my phone. Like you said, if I'm asking something, I'm asking Gemini.

15:18if I'm writing something or building something, or I use Claude, Claude and co-work. I do, but now I will say this, not in content. Never have I ever used AI to build a complete script end to end for me. I just don't think it's there yet. 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 going to change, not going to change, but as for now, that's what everyone asks. When you see these posts that are very 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.

15:47I don't think it's there. I've tried. It'd make my life a lot easier if it did, but it doesn't right now. And 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 I can just tell. And when everyone writes a post on LinkedIn, I can just tell. And I don't want to watch it. I don't want to read it. And I scroll right past it. And even And AI video content, I'm testing it. I have an AI meme page, but my actors and 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.

16:22And 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 of my life, or you can relate to the funny videos we do. You know, it's funny you say that. I saw Adam Masseri, the head of Instagram, released this thing last week that said, But 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 just, you know, just the humanity of it all.

16:53And I'm like, it's just wild. This lo-fi stuff is where it's at. I mean, everyone using AI for certain things like content would be the opposite of your playbook. 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. Like, well, I'm not going to do that because I don't, right. I don't, but, but look, I definitely still use AI for things. Like I, I might take his transcript and give it to AI and say, Hey, where's the coolest moments? What's a good hook for this?

17:21Is this hook good? But at the end of the day I'm still choosing to hook. I'm still choosing to text on screen, my team and I, we just, we just don't think AI is there yet. And again, when it's there, I'm happy to transition over, but I kind of like that. It's not, I like that we can be honest and, and, and, and, and, because I think 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.

17:47I want us to work with AI, not AI doing everything for us. 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 use it religiously. It's incredible. We're going to put Chris's Instagram, LinkedIn, in the show notes here. It's Chris Cunningham. Chris, what else did I forget? How else should people get involved in your world? Yeah, LinkedIn. I'm Chris at ClickUp.com and I'm at Cunningham on Instagram. Hit me up anywhere. I'm always willing to help on ClickUp.

18:17And 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. Amazing. Thanks, my guy. Can't wait to hang out in Miami. See you soon. Yeah, we're right here, man. Let's hang out. Sunny is beautiful. There it is. Let's do it. Wait, don't go anywhere. There's two really important things I want to tell you. First off, my book is out. Stupider people have done it. And I don't know how, but this book has made it to the USA Today bestseller list, one of the top books in the entire country.

18:49Now, all net author proceeds are going to the V Foundation for Cancer Research. And between this book and things that we're doing, we've now donated$130 ,000 in the fight against cancer. If you buy this book, if you buy the Kindle, the audio, on Amazon, on Barnes & Noble, anywhere. Money is going to fight cancer. We need your help. Please grab a copy of Stupider People Have Done It. The second thing is I want to work with you. I want to amplify your brand. I want my agency to help you get more customers, more subscribers, more whatever. I want to partner with you in so many different ways. All you got to do is go to jschwedelson.com, jschwedelson.com.

19:28And then there's a button in the upper right-hand corner that says partner. Fill out that form. Let's work together. Let's do stuff. And if this wasn't the worst podcast you've ever heard, it would be amazing if you follow the show, if you leave a comment, if you tell your friends about it. I appreciate you and go out there and crush it.