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How ClickUp survived the 2021 growth at all costs era and came out stronger ($300M ARR)

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How ClickUp survived the 2021 growth at all costs era and came out stronger ($300M ARR)

Zeb Evans, founder and CEO of ClickUp, launched the company after shutting down a prior social media automation business. Motivated by inefficiencies from using over 15 productivity tools, he built ClickUp as an internal solution to consolidate workflows into a single, flexible platform. The product stood out by allowing customizable task views, contrasting with rigid competitors. Initially bootstrapped, ClickUp grew organically through SEO and direct outreach to users dissatisfied with rival tools, ignoring conventional Silicon Valley advice to niche down or raise early venture capital. After facing VC rejections due to market competitiveness, Evans eventually partnered with Craft Ventures in 2020 during the COVID-19 pandemic, raising funds to scale paid acquisition and counter growing competition. He highlights lessons from investor David Sacks on operational scaling and stresses the importance of balancing intense focus with a fun company culture. Evans advocates for founder intuition, maintaining control, and adapting without compromising core values, as ClickUp evolved from a small internal tool to a widely used platform serving teams globally.

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We went from like a hundred to 800 employees in a year and you know a year after that I look around and I'm just like what the fuck how did we end up here where it felt like we lost our culture Hey everyone and welcome back to unicorn builders as always the shows brought you by frontlines media Silicon Valley's leading podcast production studio Our guest today is Zeb Evans founder and CEO of click up Zeb. How are you? Great happy to be here Brett. We're really excited to have you here. So I have to start off with a big question The question is the t-shirts the shirts where do they come from is there a specific brand? You know I kind of got unintentionally branded as this and if I don't wear a crazy shirt Then everybody is like what the fuck is wrong Zeb are you okay? Is the company going under? So I literally have to wear crazy shirts now and it's just a combination of brand people send me them to all the time But it's something that like I have to do now leading up to this I was looking for my closet and like shit All I have are black white and navy shirts like this is the best thing again was a black shirt So I'll have to find the brands and wear a cooler one next time my closet is Basically, click up sweatpants and crazy shirts So it's similar to like those stories a year, you know founders were like they all wear the same thing to me I am wearing the same thing because I'm not thinking about what I wear I just throw on click up sweatpants and a crazy shirt and I'm good to go That's awesome. Let's talk about click up now and let's talk about the early days the founding of the company You know what blue ocean were you seeing when you founded the company? Well, I think that it's important context that we actually built click up as an internal tool for ourselves So we were solving our own needs and I have had several near-death experiences and each time I Have moved more towards obsession with productivity and efficiency and how you get more done with the very limited time that we have And long story short my previous company was a small company of 25 person company Automating social media basically before you had that stuff existing everywhere and we were spread out amongst 15 different productivity tools. I've had a productivity tool for everything and I could not help but fuel the frustration in the pain of We were not making ourselves more productive I think we were in some ways doing the opposite were we gonna be more inefficient the more tools that we added to our stack So when I actually had a near-death experience and I realized hey, I don't want to Inflate people's egos on social media anymore. It doesn't give me energy And we shut that company down immediately and started over moved out to Palo Alto Started over and I Wanted to solve that problem with productivity software for ourselves So we built click up as just an internal tool that had Everything that we needed in one place and it's not a slack story where it took us years to figure out that We were gonna go build this as an internal tool. It was like three or four weeks where we realized like holy shit We're all obsessed with this and we're just gonna keep building and see what happens and solve our own problems At the time even let's just take project management software for example You had very rigid and Inflatable software software that you required you therefore to use multiple different project management tools You needed one for engineering, Gira needed one for boards Trello needed one for Estona list needed one for scheduling and you know for time tracking and That's where we started and the kind of unique differentiation that we had was flexibility in project management software When we began you could not create different views of tasks, you know That's standard today of like a list view and a board view you can create different ones and visualize them differently But you couldn't do that back then and that was kind of our first unique differentiator in the terms of product that gave us some early retention At what point did you decide to spin that out and build a standalone product? It was weeks we literally four weeks or so after we started building ours We were like okay, this is the product that we're gonna give to the world It's not just about our own productivity anymore like that has become our mission is just making people more productive And it was weeks it took us probably four months or so from that point to actually ship our first version of the product What are the early customer acquisition strategy look like? How are you getting those first customers? Growth hacking at the time this was going into Forms ourselves literally and trying to get people to try click up We built a tool that scraped G2 crowd and cap tear and all the review websites and when anybody wrote a negative review about a competitor We tried to match their LinkedIn and would go in and message them on LinkedIn and hey try our product and the meantime We also were big on SEO and that was a lot of learnings from my previous company I did all the SEO myself and that's what we did I click up also we started ranking heavily for we went in with the competitive route the alternate to the options of today and We were probably still are ranking top for Alternative to a sauna alternative to do it. It's alternative to all of the existing players that were there and in your mind Did you view this as a competitive market or did you not view it because you had lived with that problem and there was no one solving the problem Hyper competitive market where everyone told us do not go into this category. This is so stupid and you know It's difficult because if you even in very competitive categories, you know There's always room for improving and I think that you can consider yourself a last mover at any point you go into a category that has some competition So I don't necessarily like the last mover advantage because there's always another last mover But in our case it really was just we saw things very differently than however But he else built their software and so we went in and built our software and what we thought how work should be which is flexible and Customizable software that molds to the way that you work rather than you having to fit into somebody else's view of the world and was there a specific Market that you really locked in to say this is the market that we're gonna serve the hell out of that these big companies can't serve now Everyone always told us to you know they told us niche down as they go find a specific vertical But the whole point of us building flexible software was that we were not building it for one specific type of customer We did always focus on teams So I always said two or more people there's a variety of Individual productivity software that's actually really great and solves all those simple needs So that was the one thing that we said we're not building towards but outside of that it was teams of two or more people for productivity software And of course you naturally when you're a startup usually adopt smaller companies and smaller teams because as you know It's very difficult to get credibility to go into large organizations, especially when you know you're not funded and We weren't we were a bootstrap so we really kind of worked with what we had But that was very surprising to me that we did start getting into like legit companies and I'd say Months to a couple quarters after we launched you'd start getting interest from real companies That's such a weird go-to-market story because I feel like it defies everything that you hear at least in Silicon Valley about how Technology is supposed to be brought to market what other advice were you being given that you ignored man? I think I pretty much ignored it was always the same things when you go talk to a VC and we lived in Palo out up And so we're running into a lot of people that are in that world and that either advisors or VCs or founders themselves and First of all, it was very much always you need to pick a niche You shouldn't go into this competitive category you need to go in with some specific like route into there a vertical or something and then Also, the third thing was you need to raise fun and I was always very skeptical of I grew up in a very small town in North Carolina And I had always heard the stories of like Steve Jobs getting screwed over by his board And I was just very skeptical of venture capital. It was a foreign term to me at the time And so we really focused on doing as much as we could with the very limited resources that we have Which I think actually made us a significantly better company and forced us to really get to product market fit without using dollars as the way to do it It's something that I always call like natural product market fit rather than like artificial product market fit At what point did you decide to take on external funding? Well, my mind switched when we moved up to San Francisco and we got an office over on Howard Street near where LinkedIn was and I think still is And we started just getting inbound from VCs I mean, we always kind of had you know, I think everybody gets the emails inbound But we started literally getting people knocking on our doors and I started talking to some of them and still was like I don't know. I don't know. I don't really I just didn't really feel like a connection to the VCs that we were talking to and then there was a point in 2019 where it just became like a snowball of VCs and all of the big ones that you would know reaching out to us and I was like, I fuck it. I'm gonna go raised and I spent a week What I thought would be a week and I just staffed all of the meetings during that period like 40 of them and everybody told us great things You know, we've never seen a organic company bootstrap company like this. How much money are burning? I'm like, we're not we're profitable. No way and everybody's just telling us great feedback You know great great great and then I'm sitting there waiting for a term sheet and nothing comes and Nobody even tells us like why you know and more importantly, they don't tell you no They just keep you going and we actually end up getting two nose and one of them was from injuries and horror with there was a very thoughtful Like two-page long letter really that articulated why they didn't want to invest in us now and we did end up taking injuries and on later At our series C but outside of really that feedback there was no feedback us to like why VCs were not giving us a term sheet. Everyone says you're great. Yes. And that's what I learned. It's like if it's not a hard yes, it's a no with VCs. And there is a lot of nuance in how they work. You know, they work as swarms to some extent. When they hear that, you know, there is another player interested in giving term sheets, that's when they do. So we ended up actually not raising during that period. I was pissed off. All this was a fucking waste of time. These people were bullshitters. And we went back heads down and we built again for another six plus months. And then in really at the beginning of COVID, like March or April 2020, David's axe from Craft Vingers reached out and I connected with him. And immediately I was like, okay, this is the type of VC that I more resonate with. Somebody that's like a real person that has run a business before and that's like no bullshit. And you know, that is really that driven and like obsessed, like we are. So that was our impetus for raising our series A. Why were they saying no in that two-page letter? What was the reason? Basically highly competitive category. You've done great on organic marketing. But you need to figure out how to do that at scale. How do you build like a predictable revenue machine using dollars? And that was the nuts and bolts of it. And really I actually did take that feedback to heart. And we started doing performance acquisition very early on. And you always think you know what you're doing in performance acquisition until you don't know. It's like you get somebody else that knows what they're doing. And then you're like, oh, this person knows what they're doing. Great, now we're legit. Until you find the next person that says, you guys don't know what the fuck you're doing. And that happened to us a few times. Until we got to the point we're at today and running performance acquisition and you're spending hundreds of millions of dollars a year, is it's very complex to do. And it's all about like data, the right data, and optimization, continuous optimization over and over and over again. Is that what you're spending for a year on paid ads, hundreds of millions? Yeah. Does that feel normal just to drop that line and to say that? [laughs] Or are you dumb? It doesn't. It does now, but it's one of those things where, you know, if you zoom out and take away any period of time, holy shit, how did it all change during that period? But when you're in the thick of it, everything just kind of like incrementally, you know, increases and goes bigger and bigger. And your goalpost always moves, right? That's like the good thing about founders and the bad thing about founders is that I think great founders is that you're really never satisfied. You know, I think it's important to separate happiness and satisfaction. That was a struggle for me. Like you can still enjoy the journey and celebrate the goalposts that you achieve and still move the goalpost at this name time. You mentioned great founders there. Who are some of the non-obvious great founders in your mind? Mine are probably the obvious one. It's Steve Jobs, it's Elon, Richard Branson, big one for me. I think that he is actually an example of somebody that's been able to move around from different industries, like very, very different industries and different verticals within those, but also doing in a way that has great brand appeal and impact. And generally treat employees like, well, employees love working for him and for his companies and customers love it too. And also, look, he did things right. He lives in his island, which I've been to, Neckar Island, it's an incredible place. It's like, that's like kind of more of my founder path would be more of the Richard Branson style. I see that in the sense of your, you come across as fun, right? The shirts are fun. I was watching some YouTube videos of you grinding up coffee and explaining that. Like you've taken a very fun approach. You're not very serious, which I'm sure has helped you stand out a lot. You got to have fun while you're doing it. Maybe anybody that knows me, I have two sides. I have the very serious side like this is intense. And this is urgent. And then I have the fun side. I think you have to be able to have both. And you need to be able to have, especially with your close teams, relationships where you can flex into both. Because if you just go into one mode that's very intense, kind of aggressive founder mode, and you don't have like a great relationship and like that fun to back it up, it becomes a bad environment. It's not fun, right? You can't have fun. But I think you need to balance both. You can't make it all fun. I don't think that those companies are successful. I don't think they're the ones that create the highest impact if that's your objective is fun. I think you can have the objective that's real business metrics and real business value. And also having fun along the way. And that's what we've tried to strike the balance out. This show is brought to you by Frontlines Media, podcast production studio that helps B2B founders launch, manage and grow their own podcast. Now, if you're a founder, you may be thinking, I don't have time to host a podcast. I've got a company to build. Well, that's exactly what we built our service to do. You show up and host and we handle literally everything else. Just set up a call to discuss launching your own podcast. Visit frontlines.io/podcast. Now back to today's episode. Going back to that timeline a little bit. So you raised in spring, summer, early summer of 2020, right in the thick of COVID, it sounds like. What revenue were you at at that point? Roughly. 10 million or so. Was that an easy decision? I feel like at that point, you own the 100% of the business. You could have done a lot with it. You have 100% control. Was that a hard decision? Even though David Sacks was amazing. Was that hard to go that route? I had already kind of started flipping the switch on being open to fundraising. But I wanted the right partner. And that was the real dependency for me as to whether or not I would say yes. And you just, your gut knows more than anything. And that's really what you have to run with. I think every time that I look back and I'm like, "Damn, I knew that. I shouldn't have done that." Or I should have done that. Your gut always has something to say. From all the context that you've built over time. And in this case, it was just a gut thing that I knew it was the right thing. And we were at the point where you're not giving it. Great to raise a little as money as possible to get you by until you have some element of scale and demand from the VCs. Because then you have the car. You have the leverage. And so at our point, we had the leverage. We had the cards. We didn't need to rate. And we also were able to negotiate terms that I was very happy with and able to regain control and definitely of the company and of the board. So for me, it did become a no-brainer, especially when you consider at the time our competitors were starting to be heavily funded. Monday was heavily, heavily funded. Notions started raising during that period. And you start looking at other products and you're like, "Wait a second." I thought we invented this thing. And now all the products are starting to feel similar. So it's just natural that software, especially highly competitive software, everybody kind of like emulates everybody in some ways. And we built the views like object model where you can create custom views and then sure enough that shows up in every other product. So I knew that I really had to in some ways defend ourselves and then also be able to go in office. And to do that at our scale, we really needed a Warch S to do it. What did you learn from David Sacks? In those somewhat early days of the company history, any learnings come to mind? Yeah, it is a great person that's seen a lot of context. And he hasn't just seen it from the outside. He's been in the weeds of it. And you know, he would come down to our very early office in San Diego, which is like, I thought it was great. But whenever we had any buddy that was like legit into the office, like, what the fuck is this? You guys get a better office. You know, I can see the office in the city. And anyway, he would come in there and you know, it was really just him on the boarder early on. And with just kind of strategize and look at things and some of the insights that he had, were things like, hey guys, you know, you've got several salespeople and they're all doing above 100% attainment. You need to hire more salespeople, right? And these things seem obvious in hindsight. But having somebody there that not only knows that, but also gets in the weeds and the details with you to uncover that was really, really valuable. And over time, I think that the value of VCs, you know, is somewhat diminished as you're running your company and you're doing it well. If you're not doing it well, you know, that's where you'll hear about it. And I always want all of our investors to be very direct and very open with us and give it to us straight. And I think that we have a great relationship with our investors that are able to do that. But the point I'm making is like, well, I think what they're actually more helpful for is a lot of like the intangible things. Now, as you're running a company, all of a sudden you'll get hit with a brick sometime. Whether that's the form of like a bullshit lawsuit, but you know, like a patent troll or something. Like now we get patent trolled things like every week. And it's just like, it's funny. It's funny reading them. It's funny seeing them. But the first time you get those, you're like, oh my god, you know, what is this? Like, is there going to take our company down? And so a lot of those like intangible things that you would worry about as a founder. I think having people there by your side, their experience that are also practical in nature and are able to just like reframe your perspective help a lot. I've had on over 60 founders now of a billion dollar plus companies. And I would say that every one of them has an intense journey. But if I look at your journey, I have to imagine it's the most intense. So in less than a year and a half, you raised over a half billion dollars. Like, talk just about that time period. June, 2020 to October or fall 2021. Like how insane was that for you? It was nuts. I mean, it was just everything that could go wrong did go wrong during that period. And it also went right, right? It's important to balance both because we came out the other side. Much stronger. But when you raised that amount of money and you are also told it's growth at all fucking cost. And that means it's hiring at all costs. I mean, we went from like 100 to 800 employees in a year. And to do that, you naturally have to let your guard down and who you're hiring. And more importantly, or more problem that it depending on who you hire is that the people that you hire, the leaders that you you hire, end up really doing the majority of that. And you really can't be in the details on anything. You let everybody else run and assume that they know what they're doing. And that's what we did. We hired a lot of people from the outside that had the best backgrounds in the world on paper on LinkedIn. You know, the big companies were like, "Oh my God, they're at this company." That means that they were the ones that were successful at building that company and scaling that company. And you kind of get biased by that. And that happened to us. And you know, a year after that, I look around. And start talking to new employees and stuff and old employees. And I'm just like, "What the fuck? How did we end up here?" Where it felt like we lost our culture to some extent. Our culture was always very, it was a balance at some time. It was very intense and also very fine. And the intensity came in hard work. Everybody is working on weekends, you know, always. It's always that. We worked seven days a week and that was something we were up front about. And all of our hiring processes like, "We're going to work on weekends. It doesn't mean you have to work the whole weekend, but you will be working on weekends." Is that okay? Most people wasn't okay, but at least we aligned up front and found the people where it was. And that little anecdote extrapolated out just changes the course of your culture. And that in a nutshell is kind of what happened to us. Is we hired a ton of people and we kind of lost our culture because your culture, you know, it's not as easy as setting the milestones of what you want a culture to be and then like forming everybody to be that culture. I think it's actually like the opposite. It's forming which your culture is, especially at a small company. And it's hiring for that. It's being very transparent about people that you hire, two people that you hire, and making sure that they're aligned with your culture because people just don't change, right? People are who you are. And that's a good thing. But it's a bad thing when you mix a bunch of, you know, any equal kind of like outcomes, meaning there's people that want work life balance and there's people that don't want work life balance. So when you mix those two together, you lose culture, you know, you totally lose your culture. And that certainly happened to us during that period. What was it like going from the growth at all costs, growth at all costs that survived the profitable, because like that happened in between board meetings. That was like a 90 day period. It completely switched. What was that like, you know, reorganizing the entire company around this new idea of being profitable and it's no longer growth at all costs? Yeah. Everything changed really, really quickly. We got to get our house in order. But for us, it wasn't like this was foreign to me. You know, we ran our company as a profitable company for years when we started. We were a bootstrap and very efficient. So I knew what that felt like and I knew what that looked like. And really it was just about balancing the two. It's balancing the growth mentality with the efficient mentality. And if you can do both of those, that's the best way to build a company. So it sounds easy, but you know, we had to blow everything up. And I think it was the last chance I had to blow things out before we got too big to blow it up. But we fired a lot of those very experienced leaders that we had. And I put a lot of early people in charge, but also a lot of new leaders that we hired. They were great. They were exceptional. But they weren't the top of the ranks. You know, they were working for somebody else who was working for somebody else. And I just went and really just did my thing and talked to these people and found out who they were as humans and what they care about and their vision for how they want to build their own organization and their team. And it was really easy to sift out the people that like deserve to be the leaders based on merit. And basically said, Hey, go prove yourself. And then you know, we'll increase your ranks, increase your comp. And ultimately that's what we did. I thought it would take a year or years to turn this around. And it really took like three months to blow everything up and then put the right people in charge. And of course, you iteratively kind of keep fixing things and keep finding issues and problem solved. But it took about a quarter for everything to turn around. The point was like, Okay, I'm having fun at work again. I love the people that I'm working with and everybody else kind of felt the same. But it really is just about it's the people at a certain scale. I think when you're, you know, sub 50 people, it's really the founders that are 100% responsible for how you're running the business. And when you get to hundreds of people and thousands of people, it's very much about the leaders that you have in charge of those organizations. And they have to be aligned that you're spending money, what I always say is like spend the money as if it is your money. Like really think about that. If you had this amount of money, would you spend it here or would you spend it elsewhere? It's not monopoly money anymore during, you know, the hyper scaling phases of 2021. It felt like monopoly money to everybody. I think it even felt like that to DC is included. And you know, that was not something that a typical to be pushed to go spend a lot of money on things that you just wouldn't today. So it was very much about changing the core of the culture. And then it was changing about the strategy of the company. And it was, you know, you got to balance that because we also could have, these eventually we raised half a billion dollars in that year and a half. So it's not like we burned through all of that. We still had, you know, we're 100 or so million dollars when the market crashed. And so we're sitting there and you have some people telling you, you know, you need to blow everything up 10 times more than you're doing right now. And just like 5 or 80% of the company, I'm like, why? You know, you need to stop spending money on acquisition marketing. I'm like, why? What are we going to do? We just keep this money in the bank. We got this money for a reason. We just need to do it efficiently. And so, you know, over that course of like the next year or two, there was certainly some voices that are, you know, very much pushing you hard and saying, you're running this company into the ground, you know, you're an idiot. I heard that for sure, but you just have to go with your intuition and really be confident in what you're doing and be practical. Right. You can't have your heads in the cloud. You always have to check yourself on that. But I ran every permutation of what could happen. And we were very intentional about the dollars and very transparent with the company about what we had and where we were spending it. And you know, ultimately we got to the big milestone I was trying to get to is cashflow positive. And so January this year we achieved cashflow positivity. We didn't. We didn't necessarily stay there every month because we still have plenty of cash in the bank again. You know, it still spend it in an efficient way. But I think that was the big difference is being able to choose your own destiny. When you think back at that period, which phase did you enjoy more that, you know, massive rise in the summer of 2020 or kind of going back to your roots is what it sounds like and that pushed towards profitability. Like just from a enjoyable standpoint or a fun standpoint, which did you enjoy more? 100% going back to our roots. And you know, it's called founder mode nowadays, right? That's the thing that turned that gets thrown around. But there is something to that. And that was how we ran the company. I always ran it as founder mode early on. And I got out of that founder mode. It doesn't mean that we don't empower our leaders at all. But it does mean that I am sitting alongside these leaders as a team, as a partner, as a peer. And we dive into the details and I dive into the details in any area, very deep in details. And you know, if I smell something, then I will dive very, very deep in with the leaders. And the leaders are not trying to hide anything. Nobody has anything to hide. Our goal is always just build the best possible company that we can and give the best outcome for ourselves, for our employees and for our customers. And you know, that sounds obvious. But I think it's very hard and practiced to actually keep that at scale. And that's a much more enjoyable place for me because I know what's going on. And you also work well with leaders that are not trying to hide things. There's a lot of politics that happen in large organizations. And I had no idea about how much politics influence if you're working at a fang or a sales force or a company like that. And to some extent, like your success is based on your ability to be a politician if you're talking about very senior leadership at those companies. And that doesn't work in startups. And I'm not saying that never hire from those companies where that happens because you gotta play the game. And there's a lot of those leaders that can play the game. But also it's not something that they want to do. And it's not something that they are. And they want to go to a startup and create impact and really do the right thing. But it is definitely a cautionary tale. This show is brought to you by the Global Talent Co, a marketing leaders best friend in these times of budget cuts and efficient growth. We help marketing leaders find higher vet and manage amazing marketing talent for 50 to 70% less than their US and European counterparts. To book a free consultation, visit globaltalent.co. As you made that push back towards profitability, what were some of the lessons that have really stuck with you? Well, spending the dollars as if it's your own is a really big one that you just have to implant somehow inside of at least the leaders in your company so that they are really the stewards. You just can't check everything that's being spent. But as long as your leaders generally have that mindset, Ben, I really think that you can get there. The other thing is that data really does matter like more than anything. And predictable data really matters a lot. We always thought that we had data in a good place. And I'm sure I'll talk to you again in a year or two and tell you, oh, yeah, we thought we did today too when I'm talking to you. And we realized there's another level to this. And that's kind of the story of our data is we kept getting to another level. But when you're spending on go to market, especially performance acquisition, right? When you're acquiring customers for dollars, data is the only thing that really matters. You have to have the right data and the right objectives for that data. And that was something that we had really big learnings. Everybody has their own methodology for like LTV to CAC and retention and how much like never tension matters versus growth retention. I think every business is a bit different. We learn that our business is very different. Our business runs more like a consumer business that has we have hundreds of thousands of signups per week, hundreds of thousand organic signups plus hundreds of thousands of paid signups. We had to really, if you look at that from a sales perspective, right? You know, at least what 10 times a week you have people from the big 10 enterprises signing up. So from a sales perspective, you see somebody, oh, Google designed it. I'll face with designer. You jump right on top of it, right? You're like, oh, I need to go right after this. Lee, this is the biggest company. But really what matters is the intent of the people that are signing up and who they are as a decision maker and who they're connected to. And so in our case, it was really more about looking at the users that are already active YouTube. They already love Bicca. We didn't need to sell them on this. Many times they've already swiped their credit card for themselves or for a few people, go build relationships with those people. And then that's deserved your foot in the door to go talk to larger organization at the Google's up in the world. So for us, it really was about learning that as a data discovery was big, but also from a sales perspective and reframing everybody's mindset on not jumping on that stuff. And you know, salespeople naturally are hustlers, right? And they want to do that. And I appreciate that. And I love that about salespeople. But you really have to explain to them why this is not the right thing to do. And even if you do that, I think a lot of people, they disregard that advice. So the point I'm getting to is that the systems ultimately ultimately matter in how you distribute we how you distribute your account are. And that for us helped a lot and just getting the profitability because you really got to focus on making the system efficient. And that necessarily includes individuals. Each individual kind of has to be working on the right things and focusing on that in order to make the whole system efficient. You mentioned system there. Who's the architect behind the system was that you was the model from the team. It was very much a combination of things. But I will say I got to give credit to our now CEO, Gorov. He was hired as the head of performance acquisition really for Gorov for acquiring customers. He was a consumer guy, which by the way, I think are the best people to hire for performance marketing because those that people that have figured out, don't be able to figure out performance marketing at scale is in the consumer side. It's extremely rare. You can't even name them on like a full hand if people had to figure it out on the B2B side. And that was one of the people that I, when I blowing everything up realized, okay, he really cares about doing the right thing for the company. He wants to upgrade impact. He's got a vision in his head, a portfolio vision. I'm going to let him run with us. And we parted ways with our CRO who's the big industry guy and everybody said, zap, you're crazy. All of our good salespeople are going to leave. All of our sales managers are going to leave. And I just said I got to go with my gut. I think this is the right thing. And none of our good people leave. We had zero. I ain't talking any of them today. They all really appreciate what he's brought to the table. And he took a beginner's mindset in running sales, effectively CRO also. And he took a data mindset to that, a consumer mindset, and then a practical mindset in merging both worlds and talking to the sellers and what they care about and what they think is working. And so we were able to really merge those together in a strategy and I'd have to give him the most credit for doing that. When I think back on all of these interviews I've had with unicorn founders, there's been a few in Israel, but everyone else has been in Silicon Valley besides Doug Winter and seismic. Let's talk about the decision to stay in San Diego. Or I guess you left San Francisco, went to San Diego. What stopped you from coming back to San Francisco eventually? I have to imagine that there was some pull from investors to build here. There was and there is, and especially with AI, but at the end of the day, we've always been very distributed. And we had to be early on. We couldn't really afford salaries early on. Our engineers had to be 50K a year for us to be able to hire them, which meant that we were naturally distributed. And that was in our DNA. So it was never that we were like 100% in person, but we were mostly in person when we were in San Francisco. And that was what I thought we would do, continuing, engineering, but keep the in person mentality for everything else. And when this was before we raised funds to it was 2019 in San Francisco and everything is getting more expensive. And it was just impossible for us to hire sales and services there. It was so expensive and everybody had big egos. They didn't want to work hard. It wasn't like our culture anymore. So we started looking at other places and we looked at Atlanta and we looked at Miami and like all the classic places you would look to. Somebody told me to go check out San Diego. I came out of San Diego and I was fell in love with it. I was like, this is the California that I was looking for when I was dreaming about what California was when I was a kid. So for me, it was very much like, okay, this is it. But what we did actually was we threw out job postings and all of those markets. And then we looked at the candidates. We basically like qualified candidates. You know, we looked at the qualified candidates in the amount that it would cost to hire them. We got more in San Diego than we did elsewhere. So we're super obvious for us like, okay, yeah, let's go do this. And it's still somewhat of an untapped area for software, particularly our form of software. But I absolutely love it here. It's not going to change. This is where I am and where we'll be headquartered. But we still have a big presence in San Francisco and I still go up there very frequently. I go up there and you know, it doesn't mean that San Francisco is a very special place in my heart. And we wouldn't be the same company. I don't think every damn start there. It's very hard to know some of the people we met there and hired were pivotal in shaping our company. So I think you can still balance both of them and still kind of capitalize on what San Francisco is great at our scale at least. But I think, you know, if I was a startup again, early stage, I would go back to San Francisco. I think that there's something to be said about the people there. And I wish personally that all the people there were in a different place, you know, like I don't like San Francisco on its surface, but it is what it is. And it's really about the people and all the people are there. Let's talk about AI. If you can't wrap up this interview without talking a little bit about AI and the future of software as a whole, how are you thinking about leveraging AI right now? Well, our strategy from the very beginning of software and the very beginning of our first MVP was converging software. Right. Instead of having these multiple applications, we saw that you can build software in a flexible way and that you could really replace all these separate categories and separate verticals of software categories in one. And that is still our core strategy today. How we build our technology when we add AI and natively within the platform means that we basically get 100% of contacts for AI. You get all of the data, you get all of the activity data. We also get all the engagement in one application. So AI can ambiently engage you anywhere and you can engage AI. And that workflow application layer is extremely valuable right now. We are just scratching the surface on the value that's going to be delivered from AI in the work context and our mission for this is really killing work about work. Just maximizing human productivity. We are very focused on human productivity and it doesn't mean that we are not using agents. We are, we're using them to make humans more productive and that is the first wave of AI that I think everybody is missing. It's like, let's replace humans with agents and any area and you talked to anybody that says it is and it's I get my bullshit meters going off every time. You know, it is certainly adding tremendous value and engineering and support. But outside of that, I haven't to this day talked to anybody that is using an agent on a day to a basis until the past couple of weeks when we started really launching our agent platform, which is focused on this piece. I mean, there's so much bullshit work that you still have to do. Homework about work, writing updates, taking notes, checking on things, we're following up on things. I, when you get asked a question going and finding the previous context for it and these things are just very monotonous and in these are the things that AI is great at, but it needs both context and engagement. So I see the future of software. I mean, I think this is not as controversial as it was years ago when we started, but like all the software converges, especially all works off or all productivity software, it converges. And I think that AI converges with productivity software because the goal of productivity software is making people more productive. And the goal of AI, what is it? Why do you use AI to be more productive? So I think both of those worlds converge. And I do think that it will change things significantly. I think that a lot of companies will really have to rethink their strategy. And I think that it's going to be rocky for a lot of companies, especially point solutions, especially single kind of product, simple products that just become features on everybody else's platform when you can build significantly faster. I am obsessed with AI. I live, live sleep and breathe it. I'm deep into this into this with all of our teams because it's our mission productivity is our mission. And I think that people have not yet experienced the magic of an LLM with context and engagement. Everybody is like magic experience today is usually first time they use chat, GPT or writing something really quickly or getting the thoughtful answers about things on the spot, but there is a lot of work to be solved. We have a board that normally I would get tagged. I actually did get tagged and say, is up. You know, can you prepare this, this and this? And I just mentioned our brain agent and said, brain, can you try this? And to be honest with you, I wasn't expecting it to work nearly as good as it did. I didn't change a thing about it. I literally didn't change a thing. I just closed it and said, hey, this was written by AI, but it's better than what I would have done. And it would have taken me a weekend. It would have taken me two full days to produce this quality of work. And this technology is available today. People just aren't using it yet. So do you think of yourself as a productivity company or like what are you at its core? Productivity can be absolutely. And I think that there will be this like commoditization of productivity to some extent where you can have it given task and say, okay, what's it going to cost for a nonhuman to complete this task? And I think that nine times out of 10 you're going to choose AI to complete the task, but to be able to really do that You have to also measure the outcome of the task Like you got to be able to measure productivity productivity isn't just activity isn't just like clicking buttons and you know writing things It really is doing the task and then how much time that it take you i.e. cost and then what's the quality of the work? And we're just scratching the service on being able to measure productivity But that is our core goal to be able to measure it for humans and agents alike so that you can choose as a human Okay, I'm going to send this work to an agent because I would rather focus my energy on more creative work That only I can do and we are very much a productivity company in heart Final question for you when you reflect on this entire crazy journey What do you think spend your number one go to market lesson learn number one? Well, I think it's as simple as don't use all of a playbook from the outside go to markets one of those areas where everybody's got a playbook And there's so much methodology out there and I think a lot of those methodologies are actually really great really exceptional And I'm not saying we don't use them we do but we very much made it our own and we actually combined the best of some of the methodologies out there Every context is different every business is different many businesses are still Traditional sales like growth and now there's a wide variety of businesses that are product flood growth And like a hybrid of sales like grow and I think that area particularly you've really got to like do it yourself You've got to think from first principles and the key to that is like iterate be open to changing and too many people Even if you create your own strategy and rather than using a methodology from the outside It stays baked and you know it gets baked into your plan for the year for a variety of reasons you need to do that You don't want to change everything on sales people every month But that doesn't mean that you shouldn't iterate on it and especially change it the next year Like don't be afraid to blow things up the next year and change it significantly Especially if you know it's the right thing for the business And the business matters more than anything If you don't focus on business first there's no such thing as people first in my mind that's a fallacy If you're people first you're going to destroy the business in the name of protecting people Instead you need to be business first in the name of protecting people That's the only way to be able to do that And so when you blow things up at the end of the year for a new sales plan and raise everybody's target I think that you can get everybody on board if it is the right thing for the business Then those sales people end up actually becoming more productive And they hit their numbers better than ever even though it's a change for them Nobody likes change and I think you know and go to market that's particularly true It's like you kind of want to do things and you've got your machine You got your playbook especially as an IC you've learned it you want to keep going But you really have to continuously change things in this age Amazing Alright man we're gonna wrap here this has been awesome really appreciate the time Thanks a lot Brett you

Podcast Summary

Key Points:

  1. Zeb Evans founded ClickUp as an internal productivity tool after shutting down a previous social media automation company, driven by frustration with using multiple disjointed tools.
  2. The company bootstrapped initially, focusing on organic growth via SEO and direct outreach, and resisted early VC advice to niche down or raise funds.
  3. ClickUp’s differentiation was flexible, customizable project management software that adapted to users’ workflows, rather than forcing them into rigid systems.
  4. After initial VC rejections citing market competitiveness, ClickUp raised a Series A in 2020 with Craft Ventures, using funding to scale performance marketing and defend against competitors.
  5. Evans emphasizes balancing serious business focus with a fun culture, learning from investors like David Sacks on scaling operations while maintaining product vision and company control.

Summary:

Zeb Evans, founder and CEO of ClickUp, launched the company after shutting down a prior social media automation business. Motivated by inefficiencies from using over 15 productivity tools, he built ClickUp as an internal solution to consolidate workflows into a single, flexible platform. The product stood out by allowing customizable task views, contrasting with rigid competitors. Initially bootstrapped, ClickUp grew organically through SEO and direct outreach to users dissatisfied with rival tools, ignoring conventional Silicon Valley advice to niche down or raise early venture capital.

After facing VC rejections due to market competitiveness, Evans eventually partnered with Craft Ventures in 2020 during the COVID-19 pandemic, raising funds to scale paid acquisition and counter growing competition. He highlights lessons from investor David Sacks on operational scaling and stresses the importance of balancing intense focus with a fun company culture. Evans advocates for founder intuition, maintaining control, and adapting without compromising core values, as ClickUp evolved from a small internal tool to a widely used platform serving teams globally.

FAQs

ClickUp was originally built as an internal tool to solve the founder's own productivity frustrations, after realizing that using multiple separate tools was making his previous company inefficient.

Early customer acquisition involved growth hacking, including scraping review sites to find dissatisfied users of competitors and reaching out via LinkedIn, as well as focusing heavily on SEO and ranking for 'alternative to' keywords.

The founder was skeptical of venture capital due to stories of founders losing control, and the company focused on bootstrapping to achieve natural product-market fit without relying on external capital.

ClickUp targeted teams of two or more people, avoiding individual productivity software, and built flexible, customizable software rather than niching down into a specific vertical.

ClickUp raised its Series A in early 2020 after connecting with David Sacks from Craft Ventures, as the founder sought the right partner and needed capital to scale and compete with heavily funded rivals.

Investors cited the highly competitive market and questioned ClickUp's ability to scale predictable revenue through paid acquisition, which led the company to later invest heavily in performance marketing.

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