SaaS Interviews with CEOs, Startups, Founders
How Clickup Bootstrapped to $25m, Then Decided to Go All In and Raise $530m to Take on Giants
04 Nov 2022
Chapter 1: What is the main topic discussed in this episode?
Hey folks, hope your Q3 and Q4 is off to a good start. We just wrapped up Founder 500 in Austin, Texas. Hundreds of bootstrap founders showed up. It was an amazing time. I loved meeting so many of you.
This interview today is a recording from that session, which you're gonna love because now we have visuals, we have the founder teaching, and I made every single speaker include their revenue graphs and real artifacts in their presentations. Without further ado, let's jump in.
You are listening to Conversations with Nathan Latka, where I sit down and interview the top SaaS founders, like Eric Wan from Zoom. If you'd like to subscribe, go to getlatka.com.
We've published thousands of these interviews, and if you want to sort through them quickly by revenue or churn, CAC, valuation, or other metrics, the easiest way to do that is to go to getlatka.com and use our filtering tool. It's like a big Excel sheet for all these podcast interviews. Check it out right now at getlatka.com. Please help me in giving Chris a warm welcome to the stage.
Chris, come on up. All right, so ClickUp is a hell of a story. Now, most people know ClickUp today because they read you on TechCrunch. You guys have, like, raised tons of money. But we're going to go back to, like, the glory days, the fun days, the early days. So take us back to the VT Virginia Tech dorm room. And feel free to share any story you want there from the beginning days.
I've got some stories cleared, so if you're ready. So in the early days, Zeb and I were at college and we were always bored. We were always bored. I mean, these are gone. Oh, okay.
But these are all different. Nope. This one's behind and this one's what the audience is. Yeah. Yeah.
So yeah, we're in Virginia Tech. We had a blast. We were very bored in school and- Very bored. You see that this is a great mug shot. Had a little bit of fun in between. I don't know how this came on there, but that's for a speech I'm doing at Virginia Tech after this.
Did you give? Oh, really? This is kind of ironic. I'm looping it in. Your PR team put it in the sides. I thought it was fair game.
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Chapter 2: What inspired the founders to start ClickUp?
And within two hours, my parents are calling me like, oh, my God, Chris, did you win the lottery? And I'm like, what?
How big are we talking? What did you fake?
I'm talking this is the biggest lottery of its time, 640 million. At the time, this is 2011. This is the biggest lottery of its time. So everyone thinks I won the lottery. And I don't even tell my parents it's not true at the beginning because I want to ride this out. I want to see what can come of this.
And, again, this is really just to blow promotion up for our rapper, but it really turned on to me. I didn't realize it was going to get this big. But next thing I know, my following is going up. I do this big interview, and mind you, I'm a little tipsy. I'm 20 years old. And I get up there, and I'm like, hey, look, I'm not like all these other lottery winners.
If you're hungry at home, I'm sending that money to you. If you can't pay rent, guess what? It's coming to you. Because this money's not about me. I'm giving it back. And next thing you know, I am famous. Morgan Freeman's following me on Twitter. Ron Artest. I mean, people that I really looked up to are following me now. But then I realized this was getting out of hand.
So I'm growing a lot of followers. And from that, you know, long story short, I got a little bit of trouble, a lot of trouble with my parents. But nothing legal. I mean, this is a great marketing ad. Nothing legal. We got so much marketing. It's fair trouble. So it's fair trouble. And so from that is when we realized the importance of followers, which is what I want to get into.
I think a lot of people think they have to focus on just one company, but we really got into what we call fast followers. We learned how to grow following. Zeb was always about automation. Mind you, back when we were in the rapping days, the only way we could go on tour, we got this opportunity to open up for Wiz Khalifa, for Mac Miller. But we can't do that. We have school. We have classes.
Our parents would kill us. But Zeb is such a genius, the man builds a bot. so that we can automatically get these classes and pick before anyone else, and we get online classes. So we go on tour, we do this whole thing. But then Zeb was like, look, we need to create a business. This whole thing means something. People really care about social media following.
Give context. So what year was this?
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Chapter 3: How did ClickUp transition from college startup to a successful business?
I have to go work at Cvent. I'll help you on the side. Zeb calls me back in like six months and how much do you make it this whole like corporate job? And I'm like, you know, I'm making like 55 plus commission. It's cool. And he laughs at me. He's like, I just made that this month. I'm like, what?
So I understand like, well, let me get back on board and help you as we, you know, as this thing goes, because I want to, I want to get some of this money. Um, so things roll out and, um, you know, life is awesome. We keep moving. And from there, Cvent grows, I get my equity and I decided it's time to go back and work with Zeb full time. So we really grow fast followers.
You want to hear some cool numbers? We got to where we were making, I mean like 600 some K a month. Um, and this is, it was more than that. When I came down, he was making about 80 or so with no sales team, PLG as he always likes to start it. And we'll get to that too. The same way, man, we learned this in the early days. And this is like 22, 23. We're in Charlotte, North Carolina.
We're big fishes because we're making pretty big money. But then we also realized like Zeb had another near-death experience. You guys can research it, but he's had a lot. And they always shift. They always shift what he wants to do. And he looked at me, he's like, do we really want to be like these guys who boost social? So we started, again, building automation, which was cool.
Like a lot of the software you guys probably use now, Zeb had it early. Automatically posting, checking your stats. We were doing it before anyone else. And we were selling it to companies doing pretty well.
How many people were on the team when you were doing 600 grand a month?
Eight with four contractors.
It's a high revenue per employee.
We were doing pretty well. And Zeb obviously was saving some because he knew he had something bigger. And that's when he looked at me and he was like, let's go to Palo Alto, man. Let's do something better. Let's not just do this whole beefing people on social media. And that's when we went to our second venture, which I don't know if he's ever told you about. Have you heard about memory? Yes.
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Chapter 4: What strategies did ClickUp use to grow its user base?
So there, it was a tough time, to be honest. We all had to look at each other and think, what are we going to do?
What was the pre-revenue at this point?
Oh, we were making no money. Yeah, no money. No money. We were trying to get it to make money. We were spending our money.
How much would you say they spent up to that point? A couple hundred grand?
I would say three something, if I had to guess.
Three million? No, no, 300 grand. So just checking.
Yeah, not three million. No, we weren't balling like that. You know, crunchies are expensive. The crunchies were expensive. But here's the good news. At the time, what you guys might not realize is we moved to Palo Alto. We just hopped. I mean, Zeb flew. I hopped in a truck and I drive everything across. But we moved the office from Charlotte. Actually, no, he drove to his car.
We moved the office from Charlotte to Palo Alto. And we moved to Palo Alto because we're from small town Virginia in North Carolina. We kept hearing on the show, Silicon Valley, there was a place to be. So we thought it was going to be like Vegas for startups. Not the case, by the way. But we did a good job because we were trying to get office space.
Palantir at the time had bought up all the office space. Everything is like 90K a month, and we're not trying to do that. So what we realized is, and Zeb was very smart on this, he's like, let's get a house in a strategically good location and we'll all live there and we'll do this Silicon Valley thing. We'll do it the real way. And that's exactly what we did.
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