Lessons From 30 million views on TikTok (ft. Chris Cunningham)

D-Ro and team, you have one, one job. You have to make me look more handsome than this guy. That's it.

Good luck, baby. Good luck. I came in sharp today.

He came in sharp. Anyway, Chris, what a pleasure, man. I've been ready for this. I'm glad to be on this stage, sharing the stage with you. Dude, we, we're gonna have a lot of fun. Let's dive in. The next 30 minutes, it's gonna be hard to kind of condense it in 30 minutes, but for folks listening here and then the folks who might watch later, I want to sort of set the stage and theme of what we're going to talk about. You are head of social marketing at ClickUp, which is becoming one of my favorite B2B SaaS brands. I was joking earlier with you, and it's not a joke, it's true. And you're becoming like the Duolingo in B2B.

We're trying to do it without dancing.

Without dancing, without the mascot. Maybe you could think of a mascot too, because you look like a guy who would like appreciate a mascot.

You know, a lot of people gave me that like, hey, let's just do a unicorn, let's have a mascot. And I was like, no, let's do it a different way.

You're doing it without the mascot, which is wild.

Yeah. I don't wanna copy. I wanna do it my way.

Yeah. So big fan of what you've been doing there.

Thank you.

And so we're gonna touch on a lot of content experiments today, a lot of growth experiments, especially in the B2B realm, obviously, where a lot of the audience here are. And we're gonna talk about lessons learned, things you tried, things that didn't work, and some of the mindset stuff too, which one of the things I love about you is that you're not just giving people both on LinkedIn or whatever you're more active on, Not just tactics. I think you give a little bit of a sort of a human insight and sort of your worldviews. You blend them in really well into the tactics piece. So yeah, it's gonna be a fun one.

I mean, look, I've tried everything and I feel like everyone's preaching every day. So I just want to be real. I want to talk about my failures, talk about what works. Yeah, I've had a lot of failures. We've had some success too.

Yeah, I'm excited.

I'm happy to dive in. I want to give it all away.

That's awesome. I was excited. Okay, so for anyone who just joined, I'm KP. This is Chris Cunningham. And I'm the host of the Build in Public podcast and hence the Build in Public with Chris Cunningham. He's a legend. He's the head of social marketing at ClickUp. And my first question to you is, what's your favorite Austin thing been so far? Is it your first time in Austin?

I've been to Austin a couple times.

Okay, what's your favorite thing? My favorite thing is the people.

I'm from a small town, like I'm from no mall, no movie theater type city in Martinsville, Virginia.

Virginia, oh yeah.

So we have a NASCAR speedway, that's it. So I kind of feel home in Austin. I feel like maybe I should look here long term. I did not realize the tech scene is so good. I mean, everyone I meet is, I'm local, I'm local, I'm local. So I need to really stop sleeping on Austin. We almost moved the company here. We last minute chose San Diego, and I'm not going to say I regret it. It's been a great decision. But seeing all the, like, amazing people I've met here, I don't know, man, there might be something here. So we might— maybe we'll open a satellite office here.

You should. And also keep coming back for more events, you know, or any of the conferences. This is my first time in Austin. Loving it.

Oh, you're loving it? The food was good, but watch out, man. I'm moving a little slow already because how good it is.

My favorite takeaway has been similar to you. Like, I think the vibe is different. There's a little bit of a chill attitude in Austin, which is really cool.

But they're still productive. They're getting things done, but they're not like stressing about it.

Yeah, it's not like super like—

I resonate with that.

Yeah, me too.

I like it. I want to hire more of that.

Yeah, me too. Okay, so let's talk about content marketing and especially TikTok, because you guys are crushing it on TikTok, right? And I can't say that about too many B2B brands, you know. Very few, I think, even think of TikTok seriously. My question for you is, I guess I start with like, why did you take TikTok seriously? And then I'm gonna get to other channels, but like that one.

It's a great question because, right, I mean, I had to talk to the board, you know, every, every so often. And I think they finally hit us like, hey, you guys have a lot of creativity. Like you did a lot of cool videos in the early days. Why haven't you hit on TikTok? You know, you've hit on Instagram, you've hit on YouTube, but why haven't you hit on TikTok? And I was like, honestly, I think the trend is that, you know, I'll take blame, but I think we haven't hired a creator. Yeah. I think that's why we haven't won. So I was like, allow me to do that. Yeah. It's not been so expensive. Allow me to hire a creator, someone who's done it before because I can only go around the office and tape with so many TikToks, right? And they need to work. Like, I'm gonna stop bothering our employees. They're not TikTokers. So I found a guy, well, to answer your question, the reason why I wanna take it serious is the younger generation will be in jobs. So people can say, oh, there's no CEOs, there's no C-suite. I now start to disagree. I'm actually doing a project to really dissect and do a giveaway to see and collect emails to see who's on there. Yeah, yeah. But I have tools in which I can pull and we've had 2 different C-suite level or two different very high-level companies come back to us and just say, hey, like, I know we ghosted you, but we saw your TikToks. We love it. So a lot of salespeople hitting me up showing me that people bring up the TikToks. And where else can you reach? Not on YouTube, not on Instagram. You can, but it's very tough. But you can make a new account tomorrow and you can reach a million people. Yeah. I mean, there's— that's way bigger than here, right?

And tell us about your traction. You guys like what, 20 million, 30 million?

I got 30 million impressions last month.

That's insane.

So now everyone is Very happy with the decision to go to TikTok. I mean, and again, it's not like I'm not focusing everywhere else, but I am putting a lot of focus on TikTok. Then I'm repurposing the content so I can take those TikToks. I put them on LinkedIn. Some of them have 200. They're not getting 1,000 likes, but they're getting 200 or 300, you know, views or likes. They're doing well on Instagram Reels. I just changed the edit because, you know, a lot of times TikTok, you got to change a little bit.

I've also seen some of them coming to YouTube Shorts too.

YouTube Shorts, I get about 20 to 30K a video. So I mean, I'm doing well there too. And again, I'm just creating for one platform.

You're being strategic. You're not just simply like spraying and praying too. You're like sort of thinking about, okay, what might work better on each channel and slightly making adjustments and then repurposing as much as you can. So, because I think that's one thing like, oh, it's a big investment, you know, a lot of brands think like, oh, it's a big investment, we need to have a whole team. You got like one guy.

I have one creator. I have a PA sometimes when he shoots, so he'll shoot like once a week in the office and I have a PA and that PA will just shoot with a phone. We don't use— I mean, we have cameras, but we don't even use that. It doesn't outperform. The best strategy I can give you all here, what's killing it for me is the ABCD. I just haven't thought of the name. Wait, wait, wait,

what is the framework?

Yeah, I'm gonna give you the framework. I call it the ABCD framework just because I haven't thought of a better name. But this is what I do for TikTok, and this is why I think I'm winning, is each week my team and I meet. So I have this guy who I paid to contract. He's the producer for Zach King, the biggest TikToker in the world. And he basically showed me the framework. Yeah. And the framework that they do is the ABCD framework. So we meet each week and we take all of our views. So you wanna test for like 3 weeks. We take all of our views, and if it's really good, we highlight it green. We put this in ClickUp. You can use Excel if you're in 1995, but whatever you want to use. So

we highlight— organic plug there.

Yeah. We highlight the top ones green. Someone does decent yellow and then bad red. And then we start talking in meetings. And so our greens are our A's. That means we struck gold. Like we hit something people like. So we want to recreate that. So every week I'm creating 5 to 7 A's is what I call them. Things that are proven. A framework that's gotten, you know, $100K plus.

Right.

Then I'll do about 3 to 6 B's a week, meaning it's a new concept. A B is just something that I've seen work elsewhere, and I want to try it my page, my formula, my way. A C is just ride the wave, do a trend. You all know that like we're so and so, of course we so you know like that trend was everywhere, right? It's a very easy one to get a lot of views when you see those trends. Jump on those trends, but do not be that company who only does trends. Yeah, we hate those kind of. It's just don't do that. And then D pretend there's no rules, like experiment with the unconventional and just try something completely random because short form content. That's what people want now. They don't want the same as everything else. They see everyone's copying everyone else. You have to find a way to bring something new, something that is just in your brain. There's no rules, something random and sporadic. That is what works on short form. So then a lot of times your Ds will become an A.

Yeah.

Right? So when something becomes an A, then you just keep running the As, and eventually the A will exhaust. Your audience will get tired of it. Yeah. And that's, that's what I was saying before.

But keep doing the Ds because you're like basically taking one—

One D a week. So I do one D a week, one C a week, 2 or 3 Bs, trying something that worked elsewhere in my way. And then A's I just keep, I double down, I triple down. So like one of them is, you know, teaching my son to be a project manager. So we have the guys teaching his son and they're just making fun of the jargon words, deliverables, things like that. People love it. They see it.

There was one with, if you guys, you know, go to TikTok, go to ClickUp account and check this out. There's one with teaching your kids, like the boy and the girl, like project management. And like, I think it's Luke teaching. It's like he has his kids. And going through like the deliverables and like KPIs and whatnot.

And they had like a family meeting, they had a Gantt chart for their family meeting and stuff like that. Like people love this stuff.

Yeah, people, because I think the other thing too is when we go to an event like this, everybody here is tuned in and expecting business talk. Yeah, right, because, you know, but when you go to a platform like TikTok or YouTube Shorts or Instagram to an extent, they're really looking for Or recess or rescue from their work life. Like, they were looking for some kind of entertainment combined with some educational aspect.

You nailed it. So I have a rule of 3. I think I won't post something on social that doesn't hit this rule of 3. It either needs to add value, right? So like add value to the conversation to your— first off, you got to know your ICP, know who you're speaking to, right? For me, it's project managers. Really everyone. I want everyone to use ClickUp, but project manager is kind of the niche I focus in. So you got to know who they are. So you got to either add value to them, you got to teach them something. Think about it like it's continuous learning. We don't have time to go back to college. None of us, we don't have time. We need to We go on LinkedIn, YouTube to kind of learn real quick. But then lastly, it's make them laugh. Yeah, let's be entertained. Yeah, so if you don't do one of those 3, I don't post it because otherwise it's just exhausting my audience and they don't care about, you know, some little event we have here and there. Like, I'm strict on what I can post on my social. If it doesn't do those 3, I'm not doing it. And

so I do get the third one though is I think underrated. It is. A lot of brands start over-indexing on 1 and 2 because that's what we typically tend to do, right? We're like, oh yeah, educate, educate. We got this brochure, we got this case study, we got But the last part, which is the laugh, the human side of it, show them something human, you know. Show

them something here, make them feel relatable.

There's a video of him, there's like our CEO tanning at 2 PM or something, and it was like, I don't know, and he shows up like a PA and brings a coffee or something.

Water, yeah.

And it made me crack up. Everything else is like more strategic and thoughtful and all that, but this was like purely laughs, right? And I thought you need the mix of both.

You have— well, to me, if you want a complete strategy, if you really want a real social strategy, like, if you're doing great, like, if you nail one, great. Like, if you're good at teaching someone something, great. Because if you teach them something, of course they're going to think of you when it's time to buy, right? Like, if I teach project managers a new framework, if I'm a thought leader to them, of course when it comes time to look at project management software, they're going to give me a shot. Yeah. You know, same with making them laugh. So that's why to me, the TikTok is really working. But you got to know what platform you're doing it on. So I choose a different lane. On LinkedIn, I do a little bit of everything. I think LinkedIn is becoming more human. People are really enjoying seeing the other side, not the robotic, like, I feel like this

is the year though, 2024. I feel like there is a— I'm sensing that this is the year where I think it's going to be even more profound and pronounced, where people are like taking it a bit more seriously and invest. I'm investing into LinkedIn this year.

Heavy, heavy.

And you are, you're all in it.

You're 4 times—

when I go to my feed, every 4th, 5th tile is you.

And I'm not great yet, but I think I'll get there. I'm learning the game. LinkedIn is tough. And on a brand account, I put so much focus in LinkedIn, I forgot about doing my own. Yeah, this year I'm No more. Yeah, I'm in.

So let's talk tactics beyond TikTok, right? Actually, let's go back to TikTok and the short-form video as a way to kind of create value and just like, you know, create content, I think is sometimes tricky because people wonder, people, some of you might be wondering, there's a time constraint. You got 30 seconds or maybe like 60 seconds. Broadly explain the framework you use to create a video. Like, what is it? What does it need to have? Is that a hook? Does it need to have like answer one question that they might be thinking? Like, how do you go about it?

People are overthinking the hook now because everyone has over talked about the hook. I mean, look, a hook is important, but it's more about just grabbing attention at the beginning. So maybe it's changing the text. Maybe it's a quick cut. You do need to grab attention. Yeah, they will. They will scroll fast, especially on TikTok. You have a few seconds to grab that attention, but a lot of times it's just doing something you haven't seen before. If you look at a lot of the videos that go viral, it's just somebody starting to walk or and you're kind of curious as to what's going on. So it's not always just hey, stop and watch this video. Right. There's some people have done a really good job, like the car, the car dealerships who like fall and jump up. There's that. But I think you can find your own way. But again, with TikTok or any short form, short form's here to stay. Even if they ban TikTok, look what happened in India. Those views just went to YouTube Shorts and Instagram Reels. So make sure you have some short form strategy, but don't just, you don't have to just do what I did with making them laugh. I like it, but I'm gonna create another page. Like ClickUp is gonna be for making them laugh, but I'm still gonna have a news page. I'm still probably gonna have an AI page. I'm creating all these different pages because I still want to teach people as well. I still have a page for ClickTips. Yeah, I want people to still learn ClickUp if they want, but I think they get confused. That's a big mistake a lot of people make on their socials is they'll sometimes show their products, sometimes try to make them laugh. I think you've got to kind of find your niche on each platform, stick to that, and you can create satellite pages.

You can do a couple other adjacent pages, right?

Yeah.

So on YouTube, I spent some time on your YouTube. There's like, first of all, you have a massive audience, like 75,000 or 73,000.

We're pretty good. I'll probably get more, but yeah.

A lot of them, of course you want more. Chris, but I feel like the balance on YouTube has been, especially the long-form video, has been pretty good in the sense that it's a lot of it is educational and it's like showing templates, it's showing like how-tos. I think it's pretty good, you know? And then the Shorts are showing a little bit of entertainment side of things.

You caught us. That's my thing. I think long-form, if you're coming to look at a long-form video, you're probably looking to learn. Also, YouTube is, it's evergreen, right? It's SEO. On my long-term videos, I'm thinking of what people search. What is a project manager? How do I get started in ClickUp? I'm doing those videos. But now the key is don't just be like everyone else. It's very easy to make a training video and a tutorial video with a talking head and they're boring. Well, we try— if you notice, there's somewhere we do a rap video where we're like training you ClickUp, rapping. So we have some fun with it. That was one of our best videos.

Really? Wow. I haven't seen that. But yeah, that's cool.

It's a good one. I'll show you after. Testing commercials. YouTube is great for testing commercials. I think it's a good place to try them out.

Wait, tell me more. What does that mean? Like, basically you do a sort of almost like a prototype of a commercial you want to air and just launch it on YouTube first?

Yeah, I'll give you an example. Before we did our Super Bowl commercial, it's a lot of spend, right? For us, it was the most we'd ever— probably still the most we ever spent on something. So we wanted to get a feel of what people liked and what they didn't before because we didn't want to have a flop on the Super Bowl. Yeah. So YouTube was a great place to test. We put out certain type of ads and we realized that we had tested this kind of old feel, like click up in the past. And people really liked that. It resonated. So we ended up doing our Super Bowl commercial showing like the Declaration of Independence and they lost it. And luckily someone had a ClickUp task, you know, like that play off. But we knew it worked because we already tested on YouTube. So we had success. So I think you can test, you know, long-form things, test your long-form commercials on YouTube. I test my short-form stuff on TikTok because I quickly see if someone likes it or not. And then I know whether it's worth creating for Instagram, YouTube Shorts, etc.

Right. We should also touch on the first sort of 0 to 1 phase of any channel and the challenges that come with it. Like the number one challenge I think is just like not seeing enough results and views.

It's a grind. I'm glad you asked it too because I mean, I, you know, at the beginning—

We should address that because I feel like there's a lot of people including me before I started my Twitter journey, I thought like, man, like 0 to 1 couldn't be that hard. I'm like, shit, that's hard. And then once you get that takeoff velocity, then gets easier and easier and easier and eventually the compounding interest favors you. And like we were talking about at the speaker dinner earlier that like there would be like a weekend where I would just go to bed and wake up, or like the next day I'm like 1,000 followers. It would take 8 months to get 1,000 followers. Crazy. You know, and now it's like on a day, right? But compound interest once you have a certain number of, you know, followers. So question to you then, like, um, zero to one, like how do you navigate that stage? What, what are some tips?

You know, it's funny enough because at ClickUp I was, I was not even like— marketing was always my thing, but I ended up in sales because the only guy who could talk, it was me and some developers and So I was like, okay, I'll be our first sales rep. I'll be, you know, customer service rep. But we were scrappy, so I was still doing marketing stuff. And so I started all our channels way back then.

Yeah.

And I remember shooting and just having no success. No success. And no one even cared. No one knew who ClickUp was.

Yeah.

Yeah. So it didn't really matter anyway until I started. I stopped listening to what everyone was telling me to do because I think as soon as anyone starts social here, everyone's going to tell you what to do. Yeah. Everyone has an idea, right? Our TikTok should do this. They don't know. No one knows unless they're a creator or someone who's tested. Yeah. So what I think you got to do, I highly recommend, is I think you find experts in the space. Like for TikTok, I worked on our TikTok for a year and I should probably walk off the stage admitting this, but I only got like 4,000 followers the first year. I was not good at it. I didn't understand TikTok. I had grown my own page to like 20, but I couldn't figure out how to get ClickUp to work.

Right.

And so I had tried everything and finally I'd seen this guy. His name is Mark Somerville. He was Zach King's manager. I was like, let me talk to you about how to get this going. Yeah. So he gave me a strategy, but we still knew And I had to get the team, I had to get the COO and everyone to understand, like, hey, look, I will get X amount of views, but give me some time. Like, yeah, don't pressure me the first month and don't hit me. Give me a quarter, right? And they did. So the first month we didn't have much success at all, but then that second month we had 2 videos hit like 10 million views. Then I had their attention. And then, you know, the board is like, this is cool. Yeah, can we do more? Can you get 50 million, right? And so they gave me the goal of 20 million and I hit 30 million impressions. Now they're serious and they kept allowing me to unlock more budget. Now I can go get more creators. Now I Basically, I think it's all about proving the formula. So you need to have something like I have the ABCD formula. Yeah, I show them how I'm testing. I show them like, hey, I can't predict every week on social, but I can predict in a way because I know I'm gonna have a certain amount of A's. Yeah, I know I have— these are gonna hit, right? I know these might not. This is how I work, and I project each week.

Do you track all this on ClickUp?

I track everything on ClickUp. We have a— we have our own tools that allow me to pull up the signups and stuff, but I have a custom landing page. That landing page is how I You know how I like track who's coming from? It was coming from yeah. So it's still the board is behind it now. They're allowing me to now create more pages, and now they're hype, and now they're talking about it. But that wasn't the case in the beginning. At the beginning, they're like, "Hey, do we even?" Is they knew social wasn't the best deal.

Education man.

Yeah. Yeah. Luckily, David Sachs is he's one of our main.

Yeah.

Yeah. He was pretty in.

He's big. He's a big believer in content. He loves content.

So he was like getting Hollywood podcast.

Yeah.

And think about this: LinkedIn is now might look like TikTok. They have that new video. They're beta testing. So like, if that's the case, I'm way ahead. I make great business. Like, give me that.

Yeah.

And you know, I'll be ahead. So I do think short form is here to stay one way or another.

I think so. You know, I interviewed Gary Vee on my podcast, right?

I checked it out when I did my research on you.

It was a great, great interview. Thank you. It was in 2021, I think.

He was the same guy as always. Energy.

Energy. Insane energy. Same. Just like this. He's like, you know, so I was like, man, he has no off button. I love

him. Yeah.

What I love about Gary Vee was like, he's been preaching this. since I got to America, which is 2011, he's been preaching this exact thing, which is like invest in content in a way that you believe, like you actually— and for a decade, he's like so far ahead than anybody else. Isn't that crazy?

Well, I was just gonna say, back to your question about zero to one, like look at Gary. Gary's making these wine videos and no one cared for years. So I think you got it. The last thing I meant to say is you got to detach from the outcome and just start creating, but have a process, like still be checking, but you have to detach.

And I think in business it's harder In creator life or personal life, it's maybe slightly easier because you can justify like more reps. Sure. But obviously it's a reps game, and you can shortcut some of the journey by maybe talking to somebody who's taken more reps than you, like Zach King or, you know, his manager.

There you go.

But ultimately it's a reps game.

You're still going to take those reps yourself.

Exactly. It's like workouts. Um, what I loved was I asked Gary like, um, what's the YouTube strategy? Or what are you doing? And he's like, make 1,000 videos. And I was like, come on, he's like speaking in generic or like speaking in like, you know, I thought it was hypotheticals. And he said, no, no, no, look up the Vine Library TV. There's literally 1,000 videos that Gary Vee posted from like, I think 4 or 5 years in the first year. That's next level. And he was like, you just, and you gain a lot of intel by doing it, not by reading case studies or whatever, right? It's just, you just have to do it.

You gain a ton of knowledge. Another secret weapon I have that I do is once a week I set a call with my ICP. So I mean, it could be a project manager, it could be a, you know, CMO, but once a week I'll take a call with them. And on this call, I'm just asking, hey, what do you learn from? What podcasts are you listening to? What newsletter are you reading? What makes you laugh? You know, so I'm learning what makes them laugh. I'm learning what makes them, adds value to them. I'm learning how they learn. And then I can go create content and be a thought leader. So that is a very big secret weapon is anyone who's running your social or even in marketing, they should be talking to ICP. And then I use Riverside and not to plug, I actually like the tool and I'll record it.

Yeah, I love Riverside too.

We can do something on that. 10, 15 minutes. And then now, if they're cool with it, I have content. If they're not, I still learned a lot. Even I can just take the audio, but I learned a lot. Then I can create so much content from that. That gives me content, but also gives me more ideas. It also shows me where I should go learn because if that's the most thing I learned is I'm not a project manager. I never was. It's not my really skill. It's funny that I'm in project management, but now I'm learning so much about good project managers. I interview with them. I interviewed the one from Accenture of 20 years. Yeah. I interviewed the one from SpaceX. Yeah. You know, so I've got really good context into what project management really is. And now I can go back and share that with our world.

Yeah, so let's talk about brand for a second. You guys are building a brand, I love that. There's a bunch of— first of all, like, let's address the fact that when you guys came out into the market, you didn't come into a blue ocean as they say. It's like red AF market, right? Because you had so many big rivals and competitors including Jira and like Asana.

Advisors told us we were crazy. They were like, it doesn't make sense.

I thought it was crazy.

I did. I mean, I did too a little bit. I thought it was worth my time invested if we made a little dent.

And it reminds me of NVIDIA founders, you know, his note, he's like, if I knew how hard it was, I would probably not do it, you know. But my question to you is like, what are your reflections and lessons learned through the last 5, 6 years operating in this unbelievably competitive space? How do you stand out as a brand? How do you stand out as a competitor when there's like so many other options?

I learned a lot, and I would say, like, in those top three lessons, maybe top three lessons easy. Number one, I think is you got to take risk, right? Like, I mean, if we everything about ClickUp was a risk, and and I'll give you some examples of risk we took that I think is why we won early on. I remember that we had this big release we promised was going to come out, and Zeb and our our CTO Alex Cherkovsky unreal genius. He's like, Zeb is not ready, you know, and he's like, well, I promised everyone we got to release this thing. Like, we it's a big thing, you know. And he's like, we're going to have bugs. And Zeb sat for a second. I'll never forget. And he was like, let's just ship it anyway. Like, people know we're a new company. They know we're fighting giants. They see the mission. Let's just ship it. And that was kind of unheard of 7, 8 years ago. But we were like, let's just ship it with the bugs. And then I had the idea. I was like, hey, look, since I was running the customer service team, I was like, anyone who shows us a bug, I'll give them free ClickUp for 3 months. Wow. So we made our own free bounty hunter team. So now we're making it exciting. Like, hey, thanks for finding that bug. Here's 3 months free. If you find another one, let me know. We'll clean it up. And I would also get back in touch with them, say, hey, we fixed that bug, thank you. You know, we would jump on the bugs. And so that was like our new way. So we started shipping every single week, whereas Asana would ship like twice a year.

Yeah.

You know, and I think— I'm not gonna say they got— they just weren't moving as fast. So we started moving really fast. Secondly, I would say you got to be scrappy. So I'll give you another example of how ClickUp really popped off. We, uh, we were paying— we built this tool called AppGator because I had no sales leads and I'm trying to sell and no one knows ClickUp. So AppGator would allow me to pull Very bad reviews from our competition. So anytime someone said Asana was a two-star, Jira was a one-star, I'd see their name and their company. So I'd pop in on LinkedIn like, "Hey, I get why you hate Asana. We hate it too. That's why I built this this this tool. Click it. Let me show you. I'll give you a demo. I'll give it to you free for six months." And that was my sales strategy. So that was awesome. But in doing that, we started seeing a lot of one-star reviews for this company called Productive, and Productive was going out of business, and they were not building an export for their customers. So imagine having all your work in this tool and And this tool was going away in 1 month. So Yurkowski, the genius again, he's like, I think I can build—

They have a lot of customers. They

had a good amount of customers. I can't remember the exact number, but enough to where it changed the whole game for us. So they've been in the game for a while. They were just closing down. I don't know why. And so we built the export with 4 days to spare. So we popped into their Facebook groups, we popped out on Twitter. We're like, hey, if you thought you were going to lose your work, not today. ClickUp's here. We're heroes. Everyone's tweeting about us and we one-on-one, we're walking everyone through. It's automatic, but some people we would help. Yeah. Changed our whole company. We had so many more— I had to hire like, I think, 11 employees. Yeah. So this took us from like 15 employees to almost 30.

Wow.

Now all of a sudden it felt like we're a different company. We had more customers, other customers are telling other customers. It was awesome, man.

It reminds me of, you know, when Mint shut down abruptly like maybe a year ago. I think there was suddenly a vacuum. There's like 9 million customers, you know, that Mint had just

hanging out.

Yeah, hanging out. I think this is another instance of like being scrappy and being sort of in the moment and like spontaneous and nimble enough to like quickly do something about it, right? And like say, all right, here's an export feature for all of you guys who are already using this tool. We're similar and why don't we migrate, right? I think that's why I think it's sort of a less heard of strategy.

It's like luck comes when you're— I mean, we were all living in a house in Palo Alto, it was 4 of us, and we were obsessed with this mission. So we would, you know, we'd find something like— I think I was just seeing the reviews, I was like, hey, this is a pretty big deal. And then by us being in the same room, you know, our CTO's like, I can build this export. Next thing you know, we had way more customers and our ARR jumped up.

Yeah. What's— is that a third one? Is there another one?

Third one I'd say is hire well. Be very careful hiring early on. I think it's very easy. We talked about this yesterday. Very easy to hire, you know, like a high name from a high company. It doesn't mean they're gonna fit the way you work. It really doesn't. I think the best people we found are from the smaller companies we've purchased who move up. So I think in the early days, Find people who are really going to be in your mission, who will really dive in because it's tough, especially if you're jumping into space like we were. I mean, it was 4 of us fighting these giants, right? But there is always a way. So I think you got to believe, you got to obsess.

How big is the company now?

We are 964 employees.

So now you're one of the giants.

I think so. I mean, we're still not, we're not Jira, but we're coming.

Yeah, you're coming after.

For only 6 and a half years, you know, for where we're at, I feel beyond blessed and still kind of surreal.

Does it feel? Yeah, I was going to say, does it feel surreal?

When the growth was first happening, I mean, we got the We raised our first— we weren't even gonna raise because we, we had bootstrapped a little over $20 million ARR.

I read the article from, uh, venture capitalist David Sacks.

Yeah.

Like why they chose you guys, because he was talking about how he was impressed and surprised at how big you've grown just bootstrapping. And he was like, this is a company that doesn't need money, hence I'm going to give them money.

Exactly. We didn't need them. And I think we were turning these, these deals down because we had the horror stories of, you know, we've watched what happened to other CEOs and stuff. So our CEO is very careful. I don't want anyone to take my company. We work too hard on this. But David came in and said, look, I'm not, I'm not going to take too much. I'm not here to— you guys are killing it. You remind— he said we remind him of like PayPal in the early days.

Yeah.

So he's like, you do your thing, but you're going to need my money if you want to go fight Asana. He was right.

Yeah.

And so after we raised, I think like after 6 months, he calls us back. He's like, you want to raise again?

Yeah.

And we're like, I mean, if we can get a billion valuation, yeah, we'll raise. And we thought it was a joke. And he came back and said, I got it.

Yeah.

And so he did it again with him and I think Georgian. And yeah, then we did it again.

That was a big round, right?

That was $100 million.

Series B or Series B? Yeah.

Let me break one more time.

A question that maybe some of you might be thinking, what do you do with $100 million of money? Give me the fun answer, but also the strategic, like, because it's something that I think about sometimes. I'm like, it's not— we underestimate how hard it is to spend money wisely.

You know, maybe I'm not the best to ask because we did do a Super Bowl commercial shortly after. I don't know if that was the best investment. No, I—

I would do the same thing. I'd probably like get Matthew McConaughey and be like, ClickUp, ClickUp, ClickUp.

We tried to get Britney Spears, but she wouldn't come out of retirement. But

yeah,

so I think—

How do you resource allocate? You see what I'm saying, right?

Zeb is really, really good at this. We really found a way to get our money back, you know, quickly. Our CAC payback, we found a way to move it down like really low compared to even our competitors as well. So I think we're pretty smart with our spend. We definitely hired as well. But for us, we acquired, we've acquired like 4 or 5 companies. Really? But very strategic. So it's, I think doing these little microwork— I shouldn't say microwork, these are good companies. We find companies that are like 5 to 7 people, have an amazing product. they're doing great things, right? But we just, you know, it might be tough to make it long term. We sell them on the vision of ClickUp, we give them some cash, we give them some equity, and, you know, we bring them in and then they come in and they're coming into something bigger. So that has been probably the, I think, the best way of our spin, because now if ClickUp really is going to be one app to replace them all, we got a lot to build, right? So we can save time by, you know, buying one of these companies who already do a great job, have them integrate it. Takes 8 months to a year if we do well.

Right.

And that's kind of been our strategy. So At the beginning, I think we got a little excited and we raised again. I mean, we raised another, we raised $400 million after that Series C.

Oh, wow.

We raised $400 million Series C just before the markets kind of went down just to, you know, half. So I think, I think we're still figuring out. I think a lot of it is acquisition. I think, you know, finding ways to get customers, adding that on and then still supporting your customers.

Yeah.

And I think brand, brand, yes, but strategic. You don't need to just go do, in my opinion, you don't need to go do Super Bowl commercials. And hindsight, I'd rather get a bunch of creators and go viral and, you know, and kind of do like bottoms-up

sort of thing. Quick, another question is, what are some of the brands that you look up to or you admire and you're like, oh, they're doing great? Like you study them, like top of mind, I'm sure you have like 5 or 6, but like anything that comes to mind that are—

you know, I'm one of those who don't, I don't love to study the competition. I like to be competitive, but I'm like, just in general, I think Canva does a great job. Canva's product is It's so beautiful. So the way they can do their social is awesome. Like, I'm almost jealous sometimes. Like, let's make our docs— not jealous, because think about it.

I mean, but like, what makes them special?

Because with their products, like, I have advantages too. So you have to look at the advantage in your product. The advantage of Canva is it's beautiful. You can build something. You can show them how to build. It's actually aesthetically pleasing. Like, for me to show you a task going through an automation isn't— unless you're like me and love that stuff, it's not as aesthetically pleasing, right?

It's hard to make it sexy.

Canva looks— it's sexy when they do their ads, right? But I think we're getting there with our whiteboards and things like that. But yeah, that is an art. Like, that's something different. So I like, I like the way they've done it. Yeah, I am very,

uh— I think building a beloved brand is such an art, you know, because Canva does such a great job. Like, my wife's a school teacher. She's the farthest person from tech and startups. She's like, I don't give a shit about it.

But she loves Canva, I'm sure.

But she loves and swears by Canva.

It's great.

Because their, their whole— I think she told me about this initiative they had for like, I don't know, 3, 4 years early on, very intentionally. Canva for educators. They took it so seriously, and she said like they made it so that every teacher felt like an affiliation with them. She doesn't care about B2B or like our, my, our world, right? Yeah, but she was like, oh dude, they cared about us, the educators, because usually nobody wakes up and thinks like, you know what, let's, yeah, let's do something for educators.

They're not the enterprise a lot of times, right? Because they don't have a lot

of, uh,

um, they're teaching the students who become—

exactly. So, and so they built that great beloved sort of affinity within that sort of thing. And all of these people go on social media and say Canva is awesome, or they build something and they're like, oh, I'm

gonna look at it. And that's why I don't just, you know, I remember like a year and a half ago I got a lot of pressure to like make content just for enterprises. And I was like, look, we built this company on SMBs, you know, I get we're trying to go enterprise, I get we're getting bigger, right? But a lot of times you can't just put that focus. I think we've all realized as a company, so I'm glad because it's very easy when you start making more money, all the higher-ups will say the same thing like Yeah. We just need to make content for CEOs and the CEOs will hear about it. You make content for other marketers and stuff, they will still hear about it. I still make content for them.

Yeah. I feel like it's almost the obvious strategy. Like, I feel like you should do a little bit non-obvious thing to get, to get to win, right? Like it's—

You gotta stand out. Everyone's copying everyone. There's, I mean, look, there's so much content. Everyone's trying to win in content.

Yeah, yeah, yeah.

So you have to find a way to really, you gotta find your own flow and that takes time. And again, that takes testing and reiterating.

But let's talk AI.

Let's get

into it. I think it's top of mind for everyone. Fair to say there's like quite a few AI companies here. What's your take on it? Like, what's your— from both from a ClickUp point of view but also personally, one, what's your take on it? What are you bullish about with the power that AI is going to unleash? And I think from a company strategy, how are you guys looking at it?

So we released Brain. I think we have one— we have the first AI project manager.

Really?

So like, picture this, I'm not to plug too much, but where, where I think project management is going with AI is right now you could come in and say, okay, I wanna know what you worked on this week. And I could just say, okay, pull me KP's tasks for the past 24 hours or the past 7 days. Right. So you can do automatic standups, things like that. I think that is really helpful. I'm, I'm into the AI that's, that's helping, that's saving time.

Yeah.

As for content, we should probably talk about since it's social.

Yeah.

I don't think it's there. Like, I don't, I don't use AI to write my scripts. Everyone says it, but I don't think those scripts are great. They sound like everyone else. Yeah. You know, like, so I, I like, I love AI for ideas. I use it all the time for ideas. It gives me, A great starting point. Yeah. As for editing, it's not there yet either. Like, like try have try try having AI edit a video. Try having AI make like a hyper visual on LinkedIn for you. Type it in. Type it in on on GPT or Midjourney. It won't come out that great yet. But now in six months, that that could all change. So I'm I'm on the forefront. I am paying attention. Yeah. Right now, I still like the personal touch. Like, I don't want. I mean, I see that I can automate. I could do all my content with AI, but then I'll just look the same. So I think there's there's value into AI. It can definitely help me ideas and. outlines for scripts, but I'm not like, I'm not one of those guys that are bullish on, hey, let's AI everything, you know?

Yeah.

I think AI is gonna be great for project managers for saving steps. It will be great for content. I mean, Sora is gonna be amazing. I'm not discounting that. Sora will be great with—

Sora, the video, the opening eyes video? Yeah, yeah, yeah.

It keeps teasing us with it, but I think it'll probably be out next 2, 3 months. FTX has a strong one. You're not— that's something I'm probably confused by. FX Studio, I think it is, is coming out with another one. So there's another competitor trying to fight. So we should definitely all be aware and be paying attention to that. But I still think find your core, like have fun creating your own content. I really think if you overdo AI, I think, I mean, there's some cool things you can do and you should always, an easy play in social is to talk about AI. It always gets more views. Like I did it for ClickUp for a bit on our Twitter and it got us a lot of views, but eventually you're not reaching the right— I see. You still have to turn it back to your stuff. So you can talk about AI in your content. It will automatically get more views, but find a way to bring it back.

So switching gears to the ICP part, because I think there's a question that maybe some folks in the audience might be wondering. If you have more than one ICP, how do you cater content to them? Like you guys have multiple

ICPs. I want everyone here using ClickUp. So I want to speak to every ICP. It's not easy. If I'm being quite honest, I'm still figuring it out. The way I do it now is I'll pick a week. And I'll be like, this week, like the week, like 2 weeks before, I'll talk to like marketers, right? Yeah. So I'll change my ICP because I do ICP calls once a week. Yeah. I'll change my call and I'll talk to marketers and say, okay, I've got a lot of good intel what marketers are doing right now. I'm creating, you know, for the next week or 2 weeks, I'm creating for marketers. And then as I've got that social post built, I'm creating the next. Then maybe I'll target back project managers, then maybe I'll target back CEOs. So I kind of have to keep— because I'm the strategist behind my social, so I have to keep building and kind of switching gears. So I kind of have I'll test different ICPs and then I can say, okay, look, like I know the project manager still hit the most for me. Yeah, I get the most views. I've stapled in that community. I still have work to do better at C-suite, at marketers, at, you know, operations, developers. That's a different world. But that's why I think I'm testing these satellite pages. I think soon I can build a different page and more I see developers like and things like that.

Right. Okay, so words of wisdom. I guess we're coming to the end of our session here. So I'm curious about 3 bits of advice that you would give the younger version of you from like early days of ClickUp.

Yeah, it's definitely find a way to take risks. Like look at what you're doing and find the risk because, you know, how do you expect to stand out if you're just doing the same thing that the status quo, working the same hours? I think you have to find something, some differentiator, something you're really passionate about to really push and dive into. You have to dive into something, something that feels scary. I think it's the best. I mean, so ClickUp was built on so many risks. I can't tell you how many other risks if I had more time that we almost failed. You know, we failed building a social media app called Memory. And that's what really, I think, gave us the passion to really push on this one.

Lean towards risk, right? That's the first one.

Lean towards risk is number one. Don't listen to a lot of noise, especially since we're on social media. I think don't listen to a lot of noise. Don't pay too much attention to what your competitors are doing. Everyone's going to start sending you this, hey, like, You know, Sana did a great job on this post. That's great. That's great. It doesn't mean, but it doesn't mean you should really just do the same thing. It really doesn't. You need to find your flow. You need to find your own thing because people can feel it.

What is your unique gift to the world? I think is the big question, right? People are like, what, what, what the market slash people really want is what can you do that's special?

Yeah.

Not

like that's unique to you.

That's unique to you.

Yeah. Because we can all go create what our competitors are doing.

Yeah. Yeah.

We can do that, but they just won't feel it. Yeah. It feels different when you connect on social media with something you can tell someone put their heart and soul in or Or really is answering a problem. That's another thing I think. Don't sleep on these tools like Reddit and things like that to go find problems to to answer questions. A lot of times you want to teach people something. They're asking these questions on the internet, on YouTube, on TikTok. Really, you can type it on TikTok and see what they're asking in project management. So create content around that. Like have answers for them. My best performing content on LinkedIn is just a post that says PM versus PM versus PM because people got confused from project manager, product manager, program manager. Oh yeah. I found there's even more portfolio managers. And I made this post and it went, you know, 4,000 or 5,000 likes on LinkedIn from a brand account. So it's a lot of times answering a problem is the secret weapon. So find ways to answer problems and, you know, in your space. We talked about the hiring. I think lastly is you got to have a short-term memory. Like, just like have some fun. Like, really have some fun because literally no one told me to go make fun of work on our TikTok. Like, that was just something I said. Like, work is like kind of funny. People have to take it so serious. And I felt like when I pulled out my TikTok, I was looking for a break from where I usually would work for 90 minutes. But, you know, I want to see what's going on. So I want to be that break for them. They could laugh but still be kind of work-focused.

Right.

I think I nailed it. That's something I always thought was funny. I thought the workplace was funny. So it's something I built. So don't listen to everyone else. I had 100 ideas from everyone else, and I tried at least 45 of them. They didn't work, right? They really didn't work. And finally, when I started doing my own thing, and now— and people will leave you alone at the beginning of trying anything new with social or even in marketing. I think they're always gonna, you know, they're always gonna give you advice. And the last thing I'll say is treat it like the Gold Rush in San Francisco. My COO uses this analogy all the time, and I love it. Like, treat testing, marketing in general, or social media— like, what did they do back then? They were sifting for gold, right? Right. Sifting and trying everything. So that's what you do. You test everything in marketing. As soon as they found gold, they built a machine. Like, they built a machine to get all that gold they could. That's what you do. You test everything. So you find a good video on TikTok, you find a good campaign on marketing, redo that. You know, find a way to get the most out of that. But where most people mess up is they just get obsessed with that one gold path. Don't do that. Keep sifting. Build, build a team in place. We call it machines. We're very about building machines at ClickUp. When something works, we build a machine. We make sure it runs without the person there. From there, you have the person who's good at building machines. They move on to find and task for the next machine. Yeah. And then you have someone under them who can run that machine. That is like our— that's our North Star and why I think our growth team is doing so well. Acquisition CAC payback is going down. Social media is going up.

Yeah.

In a world where marketing is kind of tough right now, I think we're still winning. And that's, that's kind of our Our core strategy. It's the best gift I think I can give because it works for us.

Last question. This came from— this was a prompt from Andrew Davies, CMO of Paddle, my boss. I think you've met. What is something that folks who work at other companies, like including ClickUp employees, what can they do differently about building brands? Because not everybody has the chance to represent the brand account, right? But is there something that they can do tangibly to either build their personal brand or add value in the market segment on behalf of the brand they work for?

I love this.

First of all, should they— they should not sleep on this opportunity in my view, right? Step 1.

Huge hack. I think the brands like us, if you want to win, you should be investing in building internal influencers. So we have myself, we have Gaurav, we have Amrita. I'm working on having 12. I want to have 12 people in my company who have more than 10,000 followers on LinkedIn by the end of the year. That's a goal of mine. And I want them in every space because I think I think all of us should be giving back how we are here, whether it be through a podcast, whether it be through written text. Yeah. We're just talking about what we're working on because I think, you know, I want ClickUp to be looked at as a thought leader and I want someone who's new as a product manager to see a ClickUp product manager telling them how they do their job. Yeah. I want, you know, marketer, sales, same way. So I think do not sleep on internal influence, like invest it. We spend money of our own to grow these people. Yeah. You help them with writers, you have them— we have a tool at ClickUp I can give you where they can even just take a voice note and with ClickUp AI, we can turn it into like a LinkedIn post, a Twitter thread. So I have them just take a walk and take a voice note of what they're thinking, what they learned for the week, and I turn it into a post for them. I'm like, go post it. So there's all kinds of ways to do it, especially with AI now. You really have no excuses, but definitely invest. It's another app that, right, you can only post but so many times on your brand account, right? And some people are just never going to associate with a brand account. That's okay, you know, but I still like— I still follow Andrew, you know, I still learn from him. So there's people I look up to at a brand, and don't think it doesn't make me think of Paddle. It makes me want to stop by your booth, makes me want to meet with you, right, you know, because of that person. So I think it's invaluable to grow.

When I joined Paddle, I made a post saying like, I'm joining Paddle, here's why, here's the 4 reasons. And are there any customers of Paddle that I would love to, you know, I had like 18 calls booked. All of them were like, we just wanted to meet with you. And like, why did you join? So I think people are most curious. Yeah. It's personal.

It's you.

Make business personal. Because I feel like everyone's trying to make business too businessy and like too ROI and too outcome-centric, which we all agree that it's important, but it's got to be a human element there. You

gotta find a nice balance. Like, of course, of course.

All the questions I had earlier for you were genuinely my own questions about like, what would I do if I have $100 million? And like, how would you invest it? Because it's not as easy as blowing it on like a party, right?

Like, how you spend it determines everything else. Yeah, I mean, there's some people who are like on TV like, oh, spend it like you're drunk. Like, I think that's the worst advice. You better be strategic. Yeah, because especially now, look how things are. I mean, yeah, like 3 years ago, it's like we could raise all day long, you know, and Spin it how you want, but you got to really be strategic.

Yeah, I'm glad you brought up even Riverside. Um, half the time the questions I get about whatever, like, questions, like, it's almost things that I'm surprised about. They're like, what is the actual tool stack you use for the podcast? I'm like, I don't think of that as a valuable thing personally because I'm using it every day. But for someone who's just getting started,

they don't know how good it is.

Yeah, they don't know Riverside. They're thinking like just Zoom, and we live the Riverside life and we're like, oh, That could be valuable. So for an employee at either ClickUp or Paddle, anywhere, like what tools do you use in your day-to-day? Are you using Outreach or Gong? Why? Are you using— take anything, like are you using Riverside or Zoom? Why? That itself is content in my view, right? It doesn't have to be like that.

I'm going to do that tomorrow. Yeah, I have a good tool stack for social media. Everything is about that now too, because you want to see what people are using. You want to see how efficient they are because there's tons of tools, tons of options. But if you look up to someone and they have a good strategy, of course you're going to look and

Right.

That's the best kind of influencers. That's why you want people who really use your products. You don't want people who like fake use your product. They can feel it.

And also, yeah, exactly. You think people can sense it. People can sense the passion.

They can tell if you really use it when you put your tool stack. Like some people just do it for the views, but I can tell when someone explains how they use it. That's why for ClickUp, if I'm gonna have an influencer, I don't just pay them and say, do ClickUp. I will give them ClickUp with a trainer for free, have them come back to me and tell me how it helps their business. And if it does in a way that makes sense, then we can work together. But other than that, it doesn't work. I mean, you— we're immune. We hate when we see someone just like, yeah, like, I love this product. You can tell they've never used it. They're on the landing page, they're not even in the app, you know. It's like,

it's like the celebrity endorsements.

Yeah, it's so bad.

Anyway, we could have done this for— we could, we could go for another hour and a half, but I don't think— Thank you everyone for listening. Thanks everyone for being patient and listening. Appreciate it.

That was awesome, JP. I was excited.

Such a blast, man. Thank you so much. Thanks everyone.