Zeb Evans is the Founder and CEO of ClickUp, the all-in one app for tasks, docs, goals, and chat.
He’s had six near death experiences, and we talk about how those influenced him throughout life. We also talk about some of his early businesses, including one that had the FBI at his house when he was a kid, plus lessons from working at Disney.
We also get into the founding story of ClickUp, bootstrapping to $10m in ARR, hiring mistakes from scaling too fast, why Zeb likes hiring users, how ClickUp shipped generative AI features so fast, and its new chat product, which just launched earlier this week.
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Timestamps to jump in:
02:11 Zeb’s first near death experience
08:19 Childhood businesses that had the FBI at his house
18:23 Lessons from driving the monorail at Disney
25:19 Mistakes scaling from 100 to 800 employees in one year
31:04 Dropping out of college after being robbed at gunpoint
33:19 How building a CraigsList competitor led to ClickUp
35:32 Three waves of ClickUp’s product evolution
39:25 How the product slowly got worse over time
44:45 Hiring the guy who built Microsoft Teams to rebuild ClickUp
48:11 Zeb’s favorite interview question
49:59 Daily 5am standups in the first year
54:28 How ClickUp got its first customers
57:16 Bootstrapping to $10m in ARR with strong retention
58:13 Zeb’s best kept secret, user surveys (and how to run them)
1:02:42 The trend of software convergence
1:08:26 Reasons Zeb likes hiring users
1:12:19 Why VCs didn’t invest, and how it led to a better business
1:19:02 Raising from Craft, Georgian, and a16z
1:21:08 Peter Thiel: “I think you’re right”
1:24:35 How ClickUp was early to AI
1:28:03 Launching chat and video calls to hit ClickUp’s original vision
1:32:02 What Zeb’s excited and cautious about in AI
1:37:24 Why Zeb journals every day
Referenced:
Check out ClickUp
Try ClickUp’s new chat feature
Find Zeb on Twitter and LinkedIn
👉 Find on Apple, Spotify, and YouTube
Transcript
Find transcripts of all prior episodes here.
Turner Novak:
Zeb welcome to the show.
Zeb Evans:
Excited to be here. Thanks for having me, Turner.
Turner Novak:
So when I was looking up everything about you before you came on the show, you've had multiple near-death experiences. Can you talk about that?
Zeb Evans:
Yeah. I count six, and the severity of them are a bit different. I think I talked to somebody at inc who counted it as three, but in my head it's six.
The first real difficult one was when I was 10 years old. I was in a really bad accident and I was in the hospital for two months. And I couldn't eat anything for the first month or so. And, obviously, when I was 10 that was 20-plus years ago, 25 years ago, and there was no Netflix, there was no watching movies on demand. And I had to flip through a channel for watching TV.
And pretty much every commercial at that time was like McDonald's or something that reminded me of food. The TV shows themselves did also. So I couldn't watch TV because it was just reminding me of food. And that was on my mind every single day was eating.
Turner Novak:
How did you get nutrients at the time?
Zeb Evans:
Well, I was hooked up to everything in the book. They were pumping everything that was in my stomach out of my stomach. I had a ton of IVs and tube feeding things. It was all done via the hospital themselves.
My brain was going crazy. And I didn't like reading at the time. I was taught to read all the books that I felt didn't matter to me. It was all of these Shakespearean books and things like that, that you normally get in school.
There was a laptop in the hospital and somebody brought it to me and I started using it. And that was really the first time that I started using technology heavily. I grew up in North Carolina and so I don't think we had the same access to computers that everyone did. And maybe other locations in the US.
I was always obsessed with business, and selling things, and creating experiences for people. I mean, literally, since I was four or five years old I was doing that.
Turner Novak:
What was the first business that you ever did? First way you ever made money?
Zeb Evans:
So I found this company called the Oriental Trading Company. And they used to send out magazines. On my fifth birthday I asked for wholesale toys, basically. Not toys for myself I asked for ... I want to buy some wholesale toys on Oriental Trading Company. I did.
And went around the neighborhood selling those things door to door. And then got in trouble for being too annoying to neighbors. And so then I had a stand that I would just sell at. I mean, that was my thing. On the weekends I would sell toys. That was what I was obsessed with.
Turner Novak:
What toys were they?
Zeb Evans:
I remember we had Yin Yang necklaces. At the time that was popular. I had these watches that ended up not working that well. It's a novelty toy website, right, company and they're still around today in a different capacity. So it was a bunch of knickknack novelty toy style things that I thought were cool but honestly were hard to sell to people.
And I think I charged way too much retail price for them so I didn't really do that much sales. I actually don't recall really, outside of probably five times, actually selling something. Making a transaction in my first year or two of trying to sell things.
Turner Novak:
Okay. You went to the school of hard knocks. Very hard knocks.
Zeb Evans:
I got suspended actually in first grade for selling candy to students. So I would bring candy in my lunchbox. They would use their lunch money, that was supposed to be used for actual lunch, for candy. That was my first time I got suspended in school.
Turner Novak:
Oh, wow. I had a couple of times I got suspended. Not selling candy, it was usually ... It was computer-related stuff. It was always stupid things that you look back on and you're like why?
A, why did I do that? But B, also, why were we suspending kids? We should be encouraging kids to do the crazy computer stuff sometimes. As long as it's not harmful.
Zeb Evans:
I mean, that should be celebrated. Especially in America. We are the creative world where we have freedom to create, and freedom to think and build. My real struggle with school was that I feel like it was diminishing my creativity, to some extent, trying to put everyone in the same box at the same time learning the same things.
Turner Novak:
Did you make money from the school candy business? It sounds like maybe that was a little bit more successful.
Zeb Evans:
I did make money for sure. But I mean, I don't recall it ever being more than $100 total.
Turner Novak:
That's huge though. When you're middle school, high school, having 100 bucks, that's a lot.
Zeb Evans:
Yeah, I thought I was balling at the time. I was like I can go buy more candy, I can go buy more toys. Moving forward to when I was 10 and I was in the hospital, that was when I found these websites ... Like Alibaba I think had just come out at that time. Literally, I think I found them right as they were coming out. And I found eBay.
And so I married those two things together and I found ... I liked movies so I ... DVDs were huge at the time. That was the newer thing that was coming out. It was still a novelty back then, relatively novel. I started selling things like that. From buying them on Alibaba and then selling them on eBay.
And I created my first website. I used a WYSIWYG GoDaddy editor that they had back then. I just was obsessed with technology and with business and so I finally married those two. And honestly, I don't think that would've happened if I hadn't gotten ... Maybe it would've happened later in life, but I don't think I would've had the same experiences if I hadn't had that near-death experience.
Turner Novak:
So what was the eBay / Alibaba business that first really worked? Did you have any that you really cracked something and you made a significant amount of money for a kid?
Zeb Evans:
Two things. The DVDs, Disney DVDs. Disney DVDs was the thing. And now I'm talking about from 10 to 12 or 10 to 13 age. They had this thing called the Vault, the Disney Vault. Which was basically a marketing tactic to get you to join this Disney Club where you could get exclusive DVDs. But all that did was jack up the prices of DVDs, right? Classic supply and demand.
The demand was still there, the same. But the supply was exponentially lower, because they stopped selling the DVDs unless you're in this club. So I could sell a Snow White or Beauty and the Beast for $100 on eBay. And I could get them through Alibaba for about $10 bucks a pop.
Turner Novak:
Wow.
Zeb Evans:
The funny story I always tell is, I was downstairs and my dad calls me upstairs in the “you're in trouble” voice.
And so I come upstairs and there is two FBI-looking guys there. They look at me, and then they look at each other, and they just start smiling. They're just like "Oh my gosh." Classic. Because I was selling bootleg DVDs and I didn't know it really. Maybe I had an inclination at the time but I certainly wasn't aware, fully aware.
So yeah, they thought it was my dad because I was using my dad's name on the PayPal account and the eBay account. And so they came there. They just gave me a slap on the wrist. And it was a great learning lesson in life.
The second thing was Abercrombie cargo shorts. Abercrombie was the hot thing when I was growing up. And at school, it was the exclusive thing. But they were so damn expensive. I think they were $49, $50. Which in today's term that probably had to be $200 at the inflation and markup that happens in retail nowadays.
I could get those for about $15 landed from a factory through Alibaba. And I would sell those on eBay, and I would sell them to friends, and to people at school. That one actually did really, really well and I made good margins on that and pretty high volume.
Turner Novak:
The DVDs were bootleg, fake? Other people were cloning the DVDs then selling them, and then you were shipping them to the US?
Zeb Evans:
Yeah. They would from Malaysia. So they were postmarked from Malaysia. And the DVDs would come with the artwork, and the CDs, and the chapter inserts, and then that little white sticker across the top.
And so I would have to package them. And then put the artwork on the outside, put the DVD in, put the chapter insert in, put the seal across the top, and then shrink wrap them.
Turner Novak:
Oh, wow. Okay.
Zeb Evans:
It was really fun. It was so weird at the time but I actually enjoyed shrink wrap. It was creating the final product. It was like, this tangible thing that went from no value to turning it into a tangible hard good with actual value.
And yeah, obviously, in hindsight, packaging that together you would know for sure that they're bootleg. But again, I was 11 years old so I didn't ... I was more naive than I am today.
Turner Novak:
Okay. And then the cargo shorts were like ... They weren't actually Abercrombie but it was a similar style?
Zeb Evans:
I think that they were Abercrombie, honestly. They were from Sri Lanka, they were postmarked from Sri Lanka. Abercrombie's, at the time, factory was in Sri Lanka. And it would say made in Sri Lanka on them. And so they would come with the labels shipped separately. Still today you have to ship ... To import stuff you got to, basically, take the label off in many ways when you're importing apparel.
And so they would ship the label separately, and then they had this little sticker thing, or puncher thing that would punch the labels on each of the shorts. But yeah, they certainly were labeled as Abercrombie. I think that they came from the factory at Abercrombie. Probably somebody was selling excess inventory or something on the side.
Turner Novak:
Interesting. Wow. Talk about a side hustle, that one is. That's a scary one for ... I mean, the person in the factory that's shipping those out.
Zeb Evans:
The context though of 25 years ago is that things were just very different, right? You didn't really have the same oversight and insight into things that were going on. And certainly this was very new, right? The internet connecting people and being able to buy and sell things. It was a different time than it is today.
Turner Novak:
And speaking of apparel and clothing, you're wearing a very bright, and exciting, very vibrant shirt. This is a question from David George on your board at a16z. He said, "What's up with the shirts?"
Zeb Evans:
First of all, I've always loved wearing things that stood out, that were just different from other people, right? When everybody goes one way, I always zag the other way. And so I've just always been, I don't know, unique in some way.
I found some really ridiculous shirts like this one and I would wear them to the office. In 2017 and 2018 we would be in the office every single day, including weekends, and I would wear these. And when I would not wear a crazy shirt people would ask me like "Yo, what's up? What's wrong? Is the business not okay? Are you depressed right now?" So I basically pigeonholed myself into having to wear crazy shirts every single day.
A lot of the irony here is that I also don't think about what I wear each day. Going back to how Steve Jobs did it, and lots of people do it now. My closet is full of ridiculous shirts like this. And then I wear ClickUp sweatpants every day when it's not 105 degrees outside right now. That whenever I go to the office I wear the same thing every day, just a random colorful shirt and ClickUp sweatpants. So I didn't have to think about anything and I still got my brand across, so to speak. And so now it's just part of who I am.
Turner Novak:
Yeah, that makes sense. My wife always gives me a hard time of wearing ... I just have, basically, black t-shirts and just startup swag from portfolio companies and stuff. And then I got plain crew neck sweatshirts like this. You just have a rotation. It's like oh, this one's clean throw it on don't think about it. Similar with the sweatpants too. Sweatpants, jeans. The jeans if you're going out doing a lot of stuff that day.
So we hit on one of the near-death experiences. What was the next one?
Zeb Evans:
Flash forwarding so we're skipping a lot so I'll give a quick digest. I went to Virginia Tech. I feel like my whole life growing up I was, I wouldn't say meant to ... Meant to is not the right word. But almost expected to go to college by everyone, right? By society, by family, by friends. Everyone expects you to go to college. And I was just one of those kids that did not want to go to college.
I hated school. I thought school was so boring and I didn't feel like I learned anything. And my bigger insight that I always had growing up is the things that I'm learning I'm not going to use later in life and I'm going to forget them, by the way, I'm going to forget about a lot of this stuff.
Now there's exceptions to everything, right? Take that as the 80% case. The 80% of school for me was totally worthless and useless. I thought college would be the same way.
I became a DJ at the end of high school and I started a mobile DJ company. That was my most successful early, early company. The margins on that are actually insane. Margins on mobile DJing for sweet 16s, and birthday parties, and things like that.
Turner Novak:
What's the rough economics? Is it a little bit of spend upfront and then just pay for your time basically?
Zeb Evans:
Exactly. The cost is just the equipment. The equipment is actually not that expensive. I mean, it would be 100, $200 a speaker, you need a couple speakers. I used a computer, a laptop. And I would very much charge anywhere from $300 to $400, $500 an hour.
Now, it takes an hour or two to set up so all in there's a few more hours, of course, in getting the whole operation up and down. But yeah, for me, that was absolutely insane money. And so I saved a lot of money during that period.
When I went to college, I'll never forget, I had to take accounting for a year. And so I go into Accounting 101, or whatever it's called. And they're literally outlining how they're going to teach me how to be my own bookkeeper and accountant. And I'm just like this is absolutely ridiculous. They should be teaching you how to use QuickBooks, or they should be teaching you how to hire an accountant, right, not actually teaching you how to do all of the tactical things around accounting.
I never went to class after the first day. I was like, this is just totally useless. And I worked on businesses, I created an entertainment company there, and we built some music. I started managing a couple of rappers. And we had a lot of fun and made some money. I learned a lot. And I was managing their social media, which I'll tie back into later in this story.
But yeah, I was 20 years old and I had ... Also for about a year I went and worked. So I basically did a year of college. And I still got good grades, I would show up to the exams and stuff, and just study the night before.
I found this Disney program, the Disney College Program, and I applied to that. I always admired Disney for customer support. And it was somebody that I looked up to and the company that I looked up to for how they treated customers.
So I went there and I drove the monorail. I loved it. I lived and worked there. And it was intense. I mean, it taught you discipline. I don't know if it's the same thing nowadays. They probably got in a lot of trouble for how much they pushed people. But back then it was extremely intense.
And it taught me a ton of discipline and hard work. How to deal with customers that are so angry and frustrated, and being able to empathize with them and still put a smile on and not have it affect you in your day-to-day.
Turner Novak:
So this was one of the Disney theme parks?
Zeb Evans:
Yep, Disney World. It was in Orlando.
Turner Novak:
Okay. And you drove the monorail?
Zeb Evans:
I drove the monorail.
Turner Novak:
Wow. Okay. I mean, what did they teach you on customer support and being happy in customer service? It sounds pretty straightforward. What was the biggest takeaway there that people wouldn't expect?
Zeb Evans:
I think a couple of them were understanding why customers had such high expectations. Empathize with them. You go there and you see these people that are supposed to be in the happiest place in the world, they're at Disney World, why aren't they happy? Why are they complaining about every little thing?
But in reality, a lot of these families save up money for a very long time. They want their vacation to be perfect, right? And rightfully so, to some extent. And it's their first time going, their kids are there. And you don't really know what else is going on in their day, that was another thing. So looking at their expectations and the difference in reality is a lot of times how happy you are.
And so it was our job to really make that reality match their expectations. But when it didn't, understand that it's not you it's them. And it's not that it's their fault, and it's not that they're wrong. Just try to empathize with them, and try to understand, and help solve problems. That was probably the biggest insight.
The second thing was just smiling. Smiling a lot more when you're greeting customers and guests. When you are even problem-solving, smiling with them. If you smile too much, of course, they're going to call you an asshole. When you're smiling when they're really angry about something. And I've had that happen before too. But solving problems with optimism I think is a big takeaway I got from that.
Turner Novak:
Yeah, I guess I wouldn't have expected that but that makes sense. Because, we have kids, we've looked up how much it costs going to Disney World, Disneyland. At this point it's like $14, $15,000 if you are a family of four doing the full, couple day trip from out of town, you're flying in, you're staying at the hotels. That's 20% of the average annual income in the US. That's a lot of money for some families.
Zeb Evans:
A ton of money. It's again, one of those things that they probably save up for a very long period of time, they're looking forward to it for a year-plus planning it. That context really matters when you're dealing with that customer to understand why they're upset and why they're frustrated about little things, they just want it to be perfect.
I think that Disney is ... Honestly, they don't treat employees well at all. That's what I saw is they're a terrible company for employees. And so that was one of the big insights that I had also is I want to take what they've done from a guest experience perspective, put it in our company and still a lot of those values, but also treat employees. And that was, I saw how not to do it at Disney World for sure.
Turner Novak:
I've definitely heard similar stories from people where you had a bad boss or bad experience and you take the opposite approach in the future. You've seen all the ways that it goes wrong and you're like all right, I'm never going to do that again I'm going to do the opposite. So when you say you really then care and value about your employees at ClickUp, what does that look like?
Zeb Evans:
The biggest thing which sounds almost dumb saying it, but have managers that care, managers that give a shit. And I think that really, really, really matters. It is not table stakes. It is not standard for managers to truly care about their team and the company. And I think it's also equally as true, that it's very rare, to have managers that care about the team and care about the company in the same way that they need to be company first, right? You've got a lot of very empathetic managers that will love their team and become a family with their team.
But if you have that happen you've over-rotated in the wrong direction and they've become protective of their team rather than protective of the company and objective in evaluating their team and upleveling their teams. So you have to strike that balance. And I think, honestly, that's one of the biggest things to get right is having managers that care about the team and care about the company.
Turner Novak:
I've heard the analogy as, you don't treat them like a family, you treat it like a sports team. Where, it's like, you all work together. People are in it to win. I think the sports team one is an interesting one, where it makes more sense than the family.
Zeb Evans:
We say crew, because it just sounds good saying ClickUp crew. But it's very similar to that team analogy, where you have to rely on each person in order to make the boat, well first of all, not sink, and go in the right direction, especially if it's a sailing crew. And everybody plays their part.
And if somebody's not playing their part, give them opportunity to understand what's wrong, give them opportunity to grow. But if they're not the right person then they're not the right person. And you've got to be okay with moving on with people and iterating on your team. And I think that's really important.
It's also really hard to do for managers, right? It doesn't come naturally to want to let people go and make your team better but that's the natural evolution of startups, and of companies, and of teams. And if that doesn't happen I think it can risk becoming very complacent and becoming a bad place to work for the great people.
Great people want to work with other great people. Back in school when you had these group projects where one person is pulling all the weight, the other person is pulling the team down. You can't have that at teams. You've really got to have A players all around. That's easier said than done.
Turner Novak:
Have you learned from any mistakes related to that at ClickUp?
Zeb Evans:
Yeah, tons. We made these mistakes ourselves, honestly.
Turner Novak:
How did that go?
Zeb Evans:
Terrible. There was an opportunity I had a year and a half ago where I realized what had happened and really I ... For that scaling period when we were growing really fast ... We grew from 100 to 800 employees in a year. Everything that went wrong could go wrong during that period.
The biggest thing that went wrong was hiring the wrong managers and the wrong leaders. Hiring empire builders that were very much, I think, self-centered. And it's not like it's necessarily a bad thing. I think at a lot of companies, big companies, you have to be political in the work sense, and making yourself look good, and building your empire up to show how many people that you were able to manage. But it's a really bad thing for startups.
A lot of these lessons, you hear the anecdotes. “A players will hire B players and then the people below them will hire C players”. We got a lot of that where we just ended up with, I would say the biggest thing is just people that didn't care, people that really didn't give a shit about the company.
And our mission, more importantly, is one I truly care about. It's not one of those missions we just make up and put on our core values wall. It's like I genuinely am obsessed with saving people time, making people more productive. And if people aren't aligned with that mission, and really care about that, then this isn't the right place for them. Where we are focused on this mission, not other missions.
And if I had to distill it into one sentence, it would be we hired people that didn't care about the company and didn't care about the mission during that period. And then they hired more people like that.
Turner Novak:
And then really quick, just because I realized we haven't even touched on this yet, really high level, what is ClickUp? I know we'll get a little bit more into it, but what is the product?
Zeb Evans:
ClickUp is productivity platform that enables teams of all types and all sizes to work together in a single application to manage all of their work.
So what that means tactically is all of your project management software in one place. All of your resource management and time tracking and knowledge management in one place, and soon. All of your communication in one place.
And what that enables is extreme efficiencies from this toggle tax that happens between switching between products but also the inefficiencies and having to learn and onboard so many different products and data synchronization between those different products. So we drive efficiency through using a single platform that is very intentionally focused on saving you time.
Turner Novak:
Yeah, I have checked it out a little bit. I actually tried to switch over, switch everything from a different one that I use into ClickUp that I've not been happy with. And the export, I messed up, and they only let you export once a day, so I couldn't go back and re-export.
That's part of the reason I wanted to try it. I'm like, "All right, I'm going to give ClickUp a try because I'm having Zeb Evans on. I want to see if I can shift everything over and try using it." So I haven't got to fully onboard yet, but it's pretty interesting.
Zeb Evans:
Yeah, look, I'm happy to help you after this also. And we have very quick imports from pretty much every tool out there, where you can use an authorization through an API, and we can import things for you. So happy to set things up.
But that was actually one of the insights I had early on too, is we needed to be able to import your work very easily from the other players out there. And that was just honestly my intuition, my gut that I was like, how am I going to get myself to switch from, we were using 15 productivity tools at the time.
I mean I was obsessed with productivity, and still am. And so we used one tool for all of the best in class everything.
And one of the examples of that was we used Asana for lists. They only had lists at the time. And we used Trello for boards. They only had boards at the time.
First feature we built in ClickUp on one day one was allowing you to switch between a list and a board view so you didn't have to use two apps anymore. And we built an import from Asana and Trello and that was key, absolutely key to adoption, was making it really frictionless for people to import their work and get started from day zero, even if they've on day 1,000 in another tool.
Turner Novak:
So I guess before we get even deeper onto the ClickUp stuff, I'm curious then you had another near death experience that I know we were going to hit on. What was that?
Zeb Evans:
Yeah, so this was after I came back from Disney. I'd done my year at college, done almost a year at Disney and I was robbed at gunpoint in a home invasion and a 17-year-old kid put a gun to my head and my roommate was behind me and they put us in a closet.
And I had this experience where I felt... And by the way, I've never had the out-of-body near death experience that people talk about, but I had this more, I don't know, futuristic experience where I was looking at my future and really intimately focused on the things that I was doing then and prior to that.
And I was like, "This is not how I want my future to be and I don't not want to spend time in college anymore." I hated it and I thought I was wasting a ton of time in life. So it gave me that, literally in my head, I was like, "If I survive from this, I will drop out of college and I will go focus on building a business," which I knew in my heart was the thing that I was meant to do. I'm meant to build in this world, was to give jobs and create things and enable resources. And I fortunately made it through that. And that's exactly what I did.
I dropped out of school and I started my first SaaS tech company. It was social media automation. And back then, I was coding, I was in the weeds, I was hands-on, and I grew that business into 25 or so employees.
We ended up using those 15 different productivity tools while building that. And I wanted to move on to something bigger. I knew that we were not really changing the world, as cliche as that sounds. But it was more so in the sense of, are you having net positive impact on the world? That's what I was focused on. And I think increasing people's egos on social media was not net positive.
Turner Novak:
It could be helpful I guess, but it's probably not the most impactful thing you could be doing.
Zeb Evans:
And I was obsessed with saving time. And I was like, why not build this? But we focused first honestly on internally, how do we save ourselves time?
We were going to build a new Craigslist where you could pay in app and remove sketchiness from Craigslist. And I still don't know why that hasn't been done. I think I could argue maybe Facebook has started to do something like that. There's OfferUp, they still don't accept payments, they don't have reviews.
Turner Novak:
Wait, OfferUp doesn't accept payments? You still have to do it off platform?
Zeb Evans:
All of my knowledge is based on when we started ClickUp. So, it's six years ago, so maybe they do have a payments platform now. But at the time, you couldn't pay through the app, and you could not have a public transaction there and give reviews on that public transaction. Maybe they do now, but if they don't, I'm going to start this at some point, or somebody listening to this podcast could get started.
So we built ClickUp as an internal tool at first, and it was not a Slack story where it took us years to figure out we wanted to give it to the world. It was about a month where we built that thing to switch between list view and board view, which didn't exist at the time.
Now it's very common, it's table stakes. And that was the thing where I was like, "All right, let's go full and all in on this." And we totally forgot about the Craigslist thing and focused on ClickUp.
Turner Novak:
Why was it important to be able to switch back and forth? Because it, I guess, doesn't seem like that big of a deal. Why was it a really big deal?
Zeb Evans:
Well, you were still working on the same thing, right? You're putting your tasks in a board view in Trello because some people prefer boards or some projects are better set up using a board view. And then we had tasks in Asana here because we also wanted a list set up. We want to be able to look at a list. And then we also had bugs and other ticketing in Jira. So all the engineering stuff was in Jira.
And the insight that I had, which I didn't feel like was revolutionary, but it was that, "Hey, this was all the same data model behind the scenes and just it's a different visualization. Why not enable people to use the same data in a different way of viewing it?"
And that was the first thing that we invented, and that led to a lot of our early growth, was really just having that unique differentiation while it lasted, which was probably two years or so before everyone else started building it.
Turner Novak:
Really? Okay. So then what was the next... I know at this point, there's a lot that you kind of incorporate. What was then the next leg of the product besides just being able to switch between different views, what did you lean into next?
Zeb Evans:
The first version of the product, we really wanted to enable people to use one project management solution for everything, one project management product. And all that meant was adding extreme flexibility in how people work. Really, it was all about flexibility.
The second version in 2019 was about putting all of your work in one place. So that meant bringing in docs and whiteboards and forms and time tracking and resource management and scheduling, everything else outside of project management that is in some way connected to project management or work management. And that was where we really realized most of the original vision that I had of being able to put all of your work in one place, but naturally, we didn't launch most of those products with 100% feature parity with other solutions. We had to iterate. And I think iteration is the biggest key to building software, but you've got to do it quickly. Really quickly.
And we were on weekly release cycles. Ever since we started ClickUp every Friday, we launched. And we're not talking about CI/CD release cycles where we're constantly shipping code. We are shipping actual features, and new functionality, and great improvements every single Friday to our customers.
And that led to a lot of our product-led growth because I was, and still am, in the community monitoring and reading all of the feedback and listening to the community, building what they wanted us to build by voting on features and listening to their complaints and listening to their frustrations and also listening to the things that were going well. And that's ultimately what we did.
ClickUp 3.0 was later in 2021, 2022 really was kind of when we ended up building most of it in 2022, but we were working on it for over a year and a half or two years.
And 3.0 was solving a lot of those things that I talked about in feature parity, really getting to a point where the products themselves are actually usable and replaceable, could replace the other products that you're traditionally using. But also redoing a lot of performance stuff.
We scaled really quickly and through that process of shipping every week, we did not do things the right way, technically speaking, and we just built as fast as we could. So we really had to go back and re-platform, re-architecture, and rebuild a lot of the things to make it reliable and make it performant. And that was 3.0, and that ended up taking a lot longer than I thought it would be.
And I mean if we had any near death experience in our company, it was that period we were going down every day, wherever you were in the world. If you're logging on to ClickUp at your local time at 8:00 AM when it was peak traffic, ClickUp would be generally unreliable, and in many ways unusable for the first hour or so of your work day. And we would go down constantly.
I mean we were having huge major incidents every single day and there was no quick fix that we could do anymore. The long-term things were going through sharding and re-architecture, and that just took time.
And I asked our customers, I just tried to be pretty transparent and just tell them, "Hey, look, this is going to take some time. We've got this new thing coming. I promise to make things right." We did make things right. It took a lot longer than I thought it would, but during that period, we didn't really ship, we slowed down a lot.
And that was a good year of where I thought this was make or break. We are either going to get out of this and our customers are going to forgive us and they'll stick with us, or we're going to lose everything and not have customers that want to be with us anymore.
Turner Novak:
Wow. A lot to reflect on. I guess two questions related to that. How did it get to that point where you just kind of started slowing down? And then, how did you get out of it?
It seems like now, you kind of mentioned you're in a good spot now. But why did you guys slow down and then how did you start moving faster again?
Zeb Evans:
A lot of this slowdown happened over time. And a lot of times that it happened, we were able to do patches to fix those functional things. But ultimately, we got to a point where our database, we were a monolithic database and the database was just too big.
We scaled up vertically as large as we could and we were distributed in the synchronization sense. So we didn't have different databases for sharding for having different data and different databases. All of our databases were replicated in real time around the world, so it was still one database even though we had eight regions.
Turner Novak:
So anytime there was a change, you’d replicate the database in a different market?
Zeb Evans:
Yep, exactly. And that would lead to, if people are working in different regions, during peak times, it would lead to a ton of problems, because the queues get so large and somebody creates a task or edits something over here, and then over here that thing isn't technically available yet, even though it is over there, it would create a lot of data problems. And would it make it appear there was data loss even when there wasn't.
And it would transpire, and everyone getting super pissed off, rightfully so pissed off that they felt like they were doing things and creating tasks and updating things and those changes were not sticking.
And another big problem was that sometimes, you would create, and the thing would get created and your same... We had two databases in a region. Sometimes in one database, you're creating it, and the other database, you're reading from. So even you on the same device would create a task and it would immediately disappear. Even when you refresh, it would disappear and then it would come back when the queues were lower and the synchronization was actually happening.
Turner Novak:
So then how did you get out of it? I mean, it sounds like you probably just rebuilt the whole architecture? Is that how you got out of it? Or how'd you do it?
Zeb Evans:
We largely rebuilt everything.
On the infrastructure side, we went through sharding and microsharding and are now enabled to really scale databases by the horizontal approach, just adding more databases rather than scaling them up vertically.
And that's really important obviously for many reasons. And that was what enabled us to really get out of it. That single thing is the biggest piece for sure. Everything else was cherries on top, things that we could patch but not totally fix. We had to go through sharding and really a replatforming as a whole.
And we also had to become operationally competent in managing these databases. And it's harder than it sounds, even when you have very experienced people, because there's a lot of tooling that needs to be built, and there's a lot of infrastructure that needs to be fine-tuned. And there's a lot of variables and permutations in the way that things can happen and interact that you can't always predict until you start seeing things in production and finding the problems and fixing them.
So yeah, that took us a good over a year, a year and a half or so to get through that. And I think the flip side to that is our front end. So even if our database was fast, the APIs were fast, our front end was very slow, and I didn't really know why.
I'm still not the most experienced engineer in the world, and especially with very complex web applications, we didn't really have any reasons why. I would find memory leaks and things like that, but we couldn't really pinpoint exact things.
And after we scaled to 800 employees or so in that really troubling time, I had an engineering manager meeting. And when I started talking to managers and started talking to ICs more, I felt we didn't really know what we were doing on the front end, honestly. And we are a very complex front end web application.
And so I asked the room, I said, "Hey, raise your hand if you consider yourself more front end than back end." And I was expecting to get a few people.
Turner Novak:
Yeah. Half, like 50/50 at least, or something, who knows?
Zeb Evans:
Just to make the point of, "Hey, we probably need more front end folks.”
Zero people raise their hand. Literally zero people raised their hand in this management meeting. And that was when I was like, "Holy shit, we've got to fix this." And we did.
And we went, and I found the most complex web applications like Microsoft Teams, and hired the people that really built that zero to one.
And we again, took us a while to fix things and to turn it around. And we are still in the process of becoming very client first, meaning storing all or at least most of the data that we can on the client side and keeping that in sync locally rather than relying on a server for everything. But today, we are in a great place compared to where we were back then.
Turner Novak:
So what do you tell someone when they're at Microsoft Teams, they design the product. And you're like, "Hey, I'm kind of a competitor, come work on this product that's kind of broken." I'm assuming it was a better pitch than that, but what's the pitch then, if you're a founder in that spot convincing somebody to come over?
Zeb Evans:
First of all, I think you have to find the right people. I think when you do the zero to one thing, the zero to one people are different than the one to X people.
And Microsoft Teams, for example, is very different than Microsoft as a whole back then. It was really built as a startup by this guy, Brian, and it was a startup within a massive company. But these people were super excited about what they were building and they were going as fast as they can and they felt like that they had something there.
Of course, Microsoft benefits from infinite distribution for free, but they didn't know that they were going to be successful just through that. There's a plethora of Microsoft products that aren't successful even though they have that same level of distribution.
And the point I'm making is that there were a lot of people a couple of years ago when we're going through this that had already built Microsoft Teams and felt like the startup vibe was gone. It turned into that big corporation again.
So that was the first and foremost thing that I was looking for and that I was selling them on, is like, "Hey, this isn't a startup anymore. Come back to a startup, and by the way, your impact here will be 10x what it was at Microsoft because we already have this kind of zero to one thing, but we need to really go to X, and we're still a startup." And so it really was like, "Hey, use a lot of your learnings from building that and come here and help us scale this, and save us really. And your impact here will be felt forever."
And I think that the founders need to do a lot of selling when you're hiring people. But I also think that selling should generally be pretty real, pretty accurate, and you've got to sell on the points that are real and accurate.
I think too many people sell on things that are not accurate. And then you get there, it's like the expectations thing I was talking about a Disney World. If you have an employee that comes with different expectations and then gets there, they're not going to be that 10x employee that you thought they were going to be, because they're not happy.
So we were able to find several of those people from Microsoft Teams that really wanted to have more impact and wanted to go back to startup mode.
Turner Novak:
You be open, you be transparent, you give them the pitch, you make it really sexy, make it exciting, hit the urges that they might have or the needs that they're looking to fulfill. But then also be like, "Hey, this is..." Being honest about, "These are the things that may not work, things we're still solve for. It's going to be hard." All that kind of stuff.
Zeb Evans:
And I think the hard piece is something that it really, really matters. Finding people that want to do hard shit. Everyone will say that they want to, generally speaking. Some people will actually be very transparent and say like, "Hey, no, I want to coast in life right now. Not my thing."
And most people will say, "Hey, yeah, of course I want to do hard shit." But I find that that's not always true. And hard is also very subjective. It's like you can be hard at one thing at Microsoft that was extremely easy at a startup. Super subjective.
So one thing that I do is I ask people that are joining ClickUp that I interview is, "What's the hardest thing that you've ever done?" And usually they answer in the work context.
And then I ask, "Well, what's the hardest thing you've ever done or been through outside of work?" And if the answer was something that makes you feel empathetic towards them, it's probably something really hard. If you're like, "Wow, I feel for you. That was difficult." And if they don't have an answer then either they didn't go through something hard, which is not necessarily their fault.
But I don't think that people have gone through a relatively easy life are going to be great and enjoy going through a lot of really hard shit right now at a startup that's very intense and very stressful. And the other reason why they may not answer is they may not want to talk about it.
But I also have found the people that don't want to talk about it didn't really go through that hard thing with fortitude, with strength through adversity. I think that's really important is to... And I always ask, "Hey, what was something positive? Was there anything positive that came out of that?" And sometimes people will say, "What the hell? My father died. My son died. How could you ask that?" But a lot of other people will answer it with, "Yeah, it taught me a really great lesson of gratitude and how life is short, or everything happens for a reason. That's my big mentality." I think you can find those people still and those people at startups are really, really important.
Turner Novak:
Just the ability to reflect on the things happening and learn from it. I mean, you got to be a learning machine if you want to be at a startup. Things are always changing. You got to be moving quick too.
One thing I thought was interesting that I’ve seen you mention before, going back to the days of getting ClickUp started, you guys did 5am stand-up meetings every morning. Talk about doing hard stuff. Tell me about that. That just sounds like very intense. But sounds like it worked?
Zeb Evans:
It was extremely intense and it certainly didn't scale. That's one of those things that does not scale at all. But that first year, we did that, and we did it every single day.
And we actually did the classic Silicon Valley thing where you live and work in the same place. And I wasn't planning on doing it. I drove across the country with two of my employees from my previous company and we Googled Silicon Valley and Palo Alto shows up.
Turner Novak:
You Googled Silicon Valley and Palo Alto showed up. Wow. Okay.
Zeb Evans:
Swear to God. So we're like, "All right, let's go to Palo Alto, let's drive to Palo Alto." So we drive to Palo Alto, and I was expecting Reno with startup lights, just like startup, startup, startup, startup. And Palo Alto is the sleepiest place in the world.
Turner Novak:
Yeah, just like a little suburban, single family homes, ranch style.
Zeb Evans:
Right. And they actually have an ordinance there. You can't have signage, much signage at all. And so we couldn't even find any companies. We're like, "What the hell is this? We got bamboozled."
But we looked at offices there and they were so expensive. I mean the cheapest one we looked at was like $50,000 a month. We're like, "Yeah right, we can't afford this," but we found a house to live and work at. And so that made way more sense, and that's what we did. It was six or so of us living in that house.
And I set the stage as like, "Hey, this is probably going to be the hardest thing any of us have ever done, but it'll be worth it in the long run and you'll be rewarded over time." I was like, "Look, we got to be extremely healthy. It means eating healthy, it means exercising. We're going to do 5:00 AM stand-ups every day. There is no drinking, there is no going out. This is it. This is it for this year."
And I always said this year, I always said one year. That was exactly what we did. And we weren't 100% perfect on it, but if I had to give a score, I'd give us 95%. And it was incredible. And I'm very grateful to those people early on for actually doing that.
I don't think we would've been successful otherwise because, I mean, our category goes so fast as far as iterating and innovating, and it's a lot of kind of copycat in our category, where it's like we build something and then our competitors build it, and then it becomes table stakes. And then you kind of have to keep innovating.
And so my thing always and still is today, is just stay ahead. It's just keep innovating faster than competitors can. And that's the way to stay ahead in our category. And I don't think we would've done that if we weren't as intense that year, but that was definitely the thing that did not scale. After that year, I had to stop doing that, where we had to be more legit.
Turner Novak:
Yeah, I used to get up pretty early before I had kids. But with the second kid, they both now wake up at 6am so it's just, whenever they wake up, I wake up. I have no alarm, but they wake me up every morning super early.
So I was going to ask you, and you were getting into it, you’re in a super competitive space. How do you stay ahead? It sounds like just coming up with new ideas, moving quickly?
Zeb Evans:
I think one of my philosophies also is that like, any competitive category, you have to do everything right. You don't have to do it all right immediately. But everything meaning, you've got to do marketing right, you've got to do branding right, you got to do product right, you got to do engineering right, you got to get talent right.
All of those things have to be done really, really well. And you can get one right in a non-competitive category. Usually that's only going to be product. Maybe it's go-to-market if you've got a decent product, but some unique insight into go-to-market. In a non-competitive category, you can do one or a couple of those things.
But in a competitive category, you've got to do all of those things right. And that's really difficult for founders, and especially when you're starting out and you're not able to hire experienced people. You've really got to figure out all of those things as you go.
And that was something that we iterated on over time. But we certainly got product right, but we also had to get go-to-market right. We also had to get people using our product in some scalable way of adopting more users.
Turner Novak:
So how did you do that? Because I think I remember, you've mentioned before it was pretty scrappy, literally messaging people, "Try the products." What worked for getting the first couple customers, 100 people, I don't know what you consider as the zero-to-one stage, but how did you get people to start using it initially?
Zeb Evans:
We did a lot of growth hacking shit.
One of the things that we did was we built this script that would scrape all of the review websites like Capterra and G2 Crowd. And anybody that would give any of our competitors three stars, two stars, one star, we would get a notification of it, and we would try to match up their name on LinkedIn to go find them on LinkedIn and go message them.
And that actually worked pretty well. And usually they were the buyer. Usually it was the person that bought the product that was writing that review because they were pissed off. It was the actual user. So it actually was a really good way of contacting the buyer, and they appreciated the hustle and the grind. And even though that was like six, seven years ago, there wasn't a lot of, it didn't feel automated. I think nowadays that would feel like AI, so maybe that tactic doesn't work nowadays anymore.
Turner Novak:
I get like 50 AI emails a day. I'm just like, stop, unsubscribe, block the domain. It doesn't work, but…
Zeb Evans:
But that's one of the things, those are the type of things that we would do. And we would do SEO right, we'd do a lot of content.
And so we never had early on any spike, anything that was just like, this was crazy insane growth for those first couple of years. It was all very consistent. It was all consistent growth, but that growth was compounding. And that growth very much stayed on that trend of compounding, and going up in the curve that is the classic one that everybody wants to see.
But to me it didn't feel like we were ever successful those first few years. And I didn't really have anything to go on. We didn't have investors. We were bootstrapped until 2020. So for our first several years we were very much bootstrapped, and I didn't know that we were successful, so to speak.
But we were growing revenue 30-40% a month. And we had gotten to close to $10 million in ARR on our own, bootstrapping. And we didn't spend any money on marketing really, at least on traditional acquisition marketing. But I didn't even know that we were doing well, which maybe kind of brings us to investors also.
Turner Novak:
Yeah. So you were crushing it, but you didn't really know you were crushing it.
Just kind of thinking about maybe from that 0 to $10 million phase of the business, did people just retain? Was it really sticky? Were they spending a lot of money? It sounds like the growth was consistent. Why do you think it worked early on, if you could go back reflecting on it now?
Zeb Evans:
The adoption piece matters more than anything, the retention. And retention in the form of user metrics, are users actually using the product, and are they getting hooked? Is it something that they're going to stick with regardless of having a customer success person by their side teaching them how to onboard it, because we couldn't do that at the time.
So that was what we focused on more than anything, was user metrics. Let's just make sure that this thing is great and sticky. And we had a variety of paywalling options, but that piece was also key to getting right. And I was just honestly kind of winging it, because we didn't have all of the data tools that you have today, you can really run true, unbiased experiments with and learn from.
Turner Novak:
So how'd you do it?
Zeb Evans:
Trial and error, and surveys.
Surveys are, I would say one of the biggest things we got right, and we still do a ton of today, is surveys. And we do short surveys. We do 60-second surveys asking people a couple of questions. And people, users are generally very honest. I think people tend to think that users wouldn't be honest because it's not helping themselves to say, hey, I would or wouldn't pay for this feature, or how much this feature is worth to them. But what we found is they're shockingly honest in answering questions.
And that was how I did a lot of the paywall decisions. I would ask them, Hey, would you pay for this custom field permission feature? Would you pay for time tracking? If so, how much? If not, why not? And I would learn a lot from that. And that was really kind of how we iterated it on paywall and packaging, and more importantly, on product.
We do a ton of surveys today too, is asking how people feel about a feature that we release. And we look at the data for sure, but we also, the qualitative thing is the thing that matters to me more than anything is the details of why or why not somebody is using it, and what else do they want on top of that.
Turner Novak:
So if I'm listening to this, and this isn't 2017 when you're figuring it out, this like 2024 today, how do you do a good survey today? What would you tell someone if they're like, I want to try doing this too?
Zeb Evans:
Well, I think it's actually probably very much the same. I mean, we've changed a lot of our process just to make it more consistent, and more formalized, and more scalable. But it really is just winging it. And it's you writing the questions, the founder writing the questions. It was me writing the question.
Turner Novak:
Because this is like customer discovery, this is customer feedback that you're getting, so very in the weeds. It's good stuff from customers.
Zeb Evans:
Yeah, and we used to use Typeform. We use ClickUp forms now, and we have great reporting inside of... Typeform didn't really have good reporting, but we leverage all of our other reporting and dashboard capabilities in ClickUp now, so we can get really cool, granular insights and trends on the surveys that we run, but there's a lot of survey tools out there.
I do think it's important to use though a Typeform style. Typeform has really high conversion with their single kind of question focus, and that makes people, what we found, answer the surveys much better than giving them a long list of things. And we actually, we just launched a new forms experience that gives you this single question, but honestly I think even better than what Typeform does. And it gives us a really high conversion on finishing the survey.
Really that's the whole goal of the survey is get people there, and then fill it out. So I think doing that, using a survey platform that has high conversion, and asking very simple questions, really simple questions. We now do this with AI, where we take the questions that we have and we have a prompt to make it simple.
But it's really important to ask super, super simple questions. Dumb it down as much as you can, make sure everybody can understand the question that you're asking. Otherwise, you're not going to get great data.
And only ask a few questions. Make it 60 seconds, because then nobody gets survey fatigue. And if you send them a survey two weeks later, they're going to answer it also because they're like, oh, it's a ClickUp survey, it's only 60 seconds.
Turner Novak:
Yeah, that's true. You build the muscle of like, hey, it's pretty simple, fast. Do you reward people? Do you give any benefit, or no?
Zeb Evans:
No, but always the hook in the email or the in-app guide is telling them, "Hey, we need your help in making our product better." And that's what we focus on, is bringing the community along for the journey. You really have a vote and how the product turns out.
And so any active user, of course, is very open to doing that. They want to make the product better. And they have a lot of opinions themselves, and we encourage all of those opinions, and we learn from them, and we deliver on them.
Turner Novak:
It's so simple. I feel like people can forget, just a simple survey to your customer with ClickUp, sounds like ClickUp works pretty well for it.
Well, speaking of that, I know you can kind of use the product for a lot of different things. I just think about this fragmentation, all this different software and tools that's out there. If you go to the ClickUp website or if you use the product and you're in it, there's a lot of things you can do.
So I'm curious how you've thought about A, this whole consolidation of software that's happening. But then B, what are some of the interesting use cases, like most surprising types of customers that you're seeing on ClickUp?
Zeb Evans:
The word that I use is convergence. And we always, when I talked to investors early on and even when we were first raising, there was this theme of bundling versus unbundling, and consolidation versus best-of-breed tools. But our strategy was convergence. It wasn't just bundling a bunch of tools together and selling them to the customer.
Turner Novak:
That sounds kind of shitty, it's like we're going to just bundle on the fifth-best this, the sixth-best this, but together you'll buy it.
Zeb Evans:
So for us, it was always converging them. It was really putting them in the same product. One product that really replaces so many other products, and is so flexible that it can work the way you want to work, rather than an opinionated way of working.
But the other thing was we always took opinions too, that we were not building no-code software. And I think that it's really cool, I love no-code software, don't get me wrong. But it doesn't scale well with companies. You need some opinions to how you work.
And so we give the customer the ability to choose their own opinions, and then those opinions are enforced on the way that you work, rather than every single user has their own opinion about how they work. I don't think that's an efficient way of working, and we certainly have seen that in some productivity analysis.
You've really got to enforce structure and the way people work and organize things, otherwise it becomes a very bloated product ,and it almost creates more problems than you're solving. So those were the two things that we really focused on.
And as far as the use cases, we always had a very big portion of our users using us for engineering, and product, and design. And that was one of the things that was actually very surprising to me because I didn't want to build all of the bells and whistles of an Atlassian suite, and I thought it would take a very long time to get to that 80-90% feature threshold that would be needed in order for people to use us for engineering and product. But that was the most surprising one, and that still is our top three today. If you group engineering, product, and design, it is number one.
And then second is marketing and general content creation, management, things like that. The secret kind of sauce we had was that number one and number two were able to work together now for the first time. So you had marketing teams working with the engineering, product, and design teams in the same tool. And when we saw that happen, that was where the magic retention happens for us, where they retain and their active usage goes up heavily.
The third thing for us is services, agencies. Ton of agencies use our software and companies that provide services to others. And that was one of the things that I also didn't really think about early on, but we built one of our killer features, was and is time tracking. We were the first tool in our category to add actual time tracking to the product before it was a separate tool.
And we built that, and they came. The services businesses immediately wanted to use us and adopt us, and today that's one of those things that we've stayed ahead on. And so we didn't just build time tracking, we built very complex time sheet reporting, and approvals, and a lot of the management with invoicing and quoting that goes along with that.
Turner Novak:
Interesting. I would not have expected that because when I was playing around with it, I was like, time tracking, what the... Like this is a mistake, why is this in here? That seems kind of weird. But I guess it makes sense.
Zeb Evans:
And it is a mistake to show time tracking to everyone. And that's something that you learn with experimentation is, try to show it to the people that we think are going to be services to businesses rather than showing it to everyone. Because we have so much complexity under the hood, what do we show to a user? That was something that we're still figuring out right now.
And to your point, it's very difficult if you have this wide variety of customer base, you don't really know what to show them. But again, it gets back to just asking them. And that was one of the key insights that we had.
And we just had an experiment finished that we changed asking them from essentially what department are you in and what type of business do you have to, which features do you want? And just asking which features do you want, in onboarding, before they even get to the product, increased the amount of times people invite somebody before they get to the product by 10%, just because they validated that we have what they're looking for.
And then after the product, there's all these downstream metrics that also increased. So that's what we focus now. And if you had to ask me how to run this, I would've said do it this way from the beginning because I'm a feature person, right? I'm like a product person, I focus on features. But most people kind of focus on solutions, and use cases, and things like that. But for us, the focus on features is the right approach, and that has helped us a lot with retention and onboarding.
Turner Novak:
Interesting. Yeah, because I just did the onboarding recently, and I remember that. It was specifically, what do you want to use this for? And I think I clicked product management, and I think I clicked CRM, and I think I clicked content planning or something like that. Which yeah, definitely I would not have gotten those same if I would've picked like, I'm a VC, or I'm a marketing person or whatever.
So then just in terms of some of these different product things that we've talking about, you actually really like hiring users. And, I mean of course everyone likes hiring their users, obviously they make good employees when you talk about commitment to the mission, all that kind of stuff. Have you found that that works pretty well?
Zeb Evans:
Yeah, that was one of the things that helped me scaled myself.
And so I'm product founder, and I still am in every detail. Every single thing that gets shipped to production, I review before it gets shipped to production. But what wasn't happening before, was I wasn't scaling myself to get to the point before production. Every single detail was being designed and created by me.
And so then naturally, go through the journey of hiring experienced product managers from the biggest companies in the world, the best product companies in the world. But I frankly didn't get along with a lot of them, and we didn't see the world the same, and certainly didn't see product the same way. And they generally, and there's exceptions to literally everything. Whenever I always talk hyperbole, I'm talking like 80%, right? And I'm talking about my experience mostly, but they were very process oriented, and not really, didn't have product intuition. I just wouldn't consider a lot of product managers like product people.
Turner Novak:
How does that happen? Everyone should be, right?
Zeb Evans:
Yeah, you would think. But I actually think it's pretty rare for a product manager to be an exceptional product person. And there are cases of it, and we certainly have a really great experienced product managers today that are great product people.
But generally speaking, I think the best way to hire product managers are hiring your users, because they're the ones that have felt the pain and the benefit of your product for years, usually. And they're the ones that are very obsessed with the product, they care so much. You're not going to be able to get that by hiring somebody from the outside unless they were already a user also.
So users for us are really great ways to hire product people, and it's been a... Our product would not work right, our product organization and process would not work right now without having a wide variety of users that are running product management for us. And I think that was a key way to scale myself as a product founder.
Turner Novak:
You hinted on this a little bit, but so what makes a good product person? Kind of a product manager and a product-minded person are two different things. What makes a good product person?
Zeb Evans:
It's the intuition. It's the piece of, Hey, I could run through this six-month process, and do all of the user research, and testing, and experimentation, and design phase and get to an outcome.
Or, I can basically do it myself in a week, and those are the product people that can just do it themselves in a week. And they won't get it right all the time, but they will get it right most of the time. They'll get it right 80% of the time.
And as long as you're iterating, meaning you're not spending another six months building something and risking six months of time building it, you spend another month building that, de-scope it to a month, build that, learn from it, get feedback from users, then I think it's the absolutely right way to build product.
I think it's the fastest way to build product, but that's not a way a lot of people want to work. It’s not. And that's totally fine. And I think that at a certain scale, maybe the way we're doing it might not work, but this is the funnest way for me to work. I think it's the fastest way for sure to work, and that's really what I'm focused on is speed of delivery.
Turner Novak:
It sounds like it's almost an intuition thing. You kind of know what the data is going to say, so just go with it. If you're right, I guess you're not... Like you said, maybe you're right 80% of the time.
So then I'm curious, you hinted on this a little bit. You went from 0 to $10 million in revenue. You didn't raise any money, but I know you did try at some point earlier on. Can you talk about that journey?
Zeb Evans:
So we were in San Francisco by this point. We were in Palo Alto for that first year, year and a half. And then we moved up to San Francisco because we realized, oh, this is where Silicon Valley is and startups are nowadays. So we moved up there.
And we would have investors literally knock on our door and come and try and talk to us. And I didn't want to raise at the time, and frankly, I don't think I really wanted to raise at all. I didn't really see that as the way to build the business. And I was very naive. I saw all of these stories from the outside of founders getting fired from their own companies, and I just kind of wanted to control my own destiny, and I really cared about product the most.
So I started talking to investors, and we would get kind of wined and dined, and I would show them some of our metrics, but I really just didn't want to spend a bunch of time with them. So I kind of just developed some relationships over time.
And then in the end of 2019, the attention from investors was just so heavy. It was like my inbox was just getting flooded from investors. And so I was like, okay, let me think about this, maybe we go run a process.
But also, the bigger thing was that our competitors were raising a ton of money. And they were outspending us on acquisition marketing, and it's somewhat of a land grab in this category. So I was thinking about it from that perspective also.
And so, we had moved to San Diego at that time, and I decided to go back up to San Francisco and run a process. And so I went up there for a week. I had, I don't know, 30 or 40 meetings with different firms. And everyone was super impressed with metrics, super impressed with the business and product, and they did their diligence in talking to customers, and I didn't hear one negative thing really.
And then the next week I'm like, well, it's crickets. What's going on? Nobody's messaging me. I'm like reaching out. Hey, what's up? What's going on? I feel like nobody was giving me a straight answer, and everybody was just kind of, I don't know, leading me on. And they weren't saying no though.
And then we got our first no from Andreessen Horowitz. And it was very thoughtful, and it was a page long of, Hey, look, here's where we're at basically, and we think that you've got more to validate before we believe that you can be a category winner. And I greatly appreciated that, respect them more than anything, and ultimately took them on later as our series C investor, they led that round.
But everyone else didn't respond, they didn't say no to us. And it was, I waited another week in San Francisco, and finally I was just like, fuck this. I'm going back, and I'm going to go back to work, and we're going to do this ourselves. And that's what I wrote in my journal. I was like, fuck the VCs, we're going to go do this ourselves.
I was really frustrated because it felt like I had spent so much time, and everybody was almost forcing me to come up and talk to them. But then nobody gave us a deal.
But more importantly, nobody told us why. There was no why behind why they wouldn't do it. And, except for Andreessen Horowitz, of course. And so we just went on ourselves for the next several months, until May of 2020.
And I actually think, again, everything happens for a reason, I think. I'm very glad we didn't raise at that time. We figured a lot more things out later that we probably would not have figured out. And I think, I don't think I would've hired a couple of the people and put them in powerful positions if we had raised funds back then.
Turner Novak:
So why is that? Because that, I mean, it sounds like existential different paths the business would've been on. Why would you have not made those decisions?
Zeb Evans:
I think because if you get, especially those top tier VCs early on, they have arguably a great playbook for you in many ways. But they also have a lot of very experienced people, that you get... The halo effect is real from those top tier firms when you're hiring people.
But I think that there is at least an argument in my mind of whether or not you really want those very experienced people, especially early on. I think in later stages they're more helpful. But in early stages, I don't think they are. And there's again, exceptions to everything. Some of them are, but generally speaking, I think that you don't want as much experience early on when you're building. You want iteration and learning, and growing, and hard work, and people just being on the same team and figuring things out.
And there was a couple of people that we hired that I put in very powerful positions that fundamentally changed our business, improved our business, and I think that if I had a VC there, they would've been like, "First of all, what are you doing? We shouldn't make this person in charge of all revenue immediately, they have zero experience."
But secondly, they would've given me people that are more experienced, and I probably would've hired those people because, why wouldn't you? If you can get somebody that's done it before and somebody that's very competent and knowledgeable in what I want them to do here, why wouldn't you hire that person? But ultimately, we did a lot of things differently because we hired people that were less experienced.
Turner Novak:
That makes sense. And then you did end up raising money. I've kind of heard this. I mean, I know what happened, but then you did end up raising a little bit a couple months later in May, 2020. What happened?
Zeb Evans:
Yep. So probably six months or so later. Well, first of all, it was the very beginning of COVID.
Turner Novak:
Did you see a bump? Just curious. Did the business change at all when COVID hit?
Zeb Evans:
We didn't. Everyone thought we would, and everyone said that. Sometimes we would get asked, are we a COVID business? Really what I see now and looking back, it's those communication tools that got the bump.
It's the Zooms and the chat communication tools. Those were the ones that were needed by a lot of those businesses because still even at that time. The people that really needed work management software, they were already using it. They weren't doing it on sticky notes and doing it on pen and paper. They were already using that software.I think you could argue, and we didn't see it, but we did always see that consistent growth happen. I imagine a lot of that consistent growth happen, because people went from not using work software to using work software, and then that became a gradual kind of foot in the door into work management software. I buy that for sure. Yeah, we never saw that bump during COVID.
And around then, we had Craft Ventures reach out to us and David Sachs wanted to chat. And I massively respected and respect him today. And chatted with him and it was supposed to be just kind of a short, informal conversation, turned into a very in-depth conversation and he gave us a term sheet later that day.
Turner Novak:
Wow. Totally different, yeah, experience.
Zeb Evans:
Night and day different, and it was also a night and day different conversation. Talking with somebody that had really done it before and was very, I think founder-friendly and founder-focused was so different than most of the VCs that I had talked to before. He was just a no bullshit type of guy and I really admired that and appreciated that and it gave me a lot of trust in having them as a partner.
It was a no-brainer for me to say yes to that deal. The other investor we brought on was Georgian Partners who, they were a ClickUp user, and they were a real ClickUp user, meaning their whole company used ClickUp. A lot of VCs told us they did and they didn't actually use it, but they were a real ClickUp user. Those were the two best investors I really could have asked for our Series A.
Turner Novak:
Then I know David, you said z16Z did end up coming back into invest. Did that play a role, the fact that they were just like, I guess a little bit more upfront with you early on? It sounds like you really respected that.
Zeb Evans:
A thousand percent. We didn't even consider any of the VCs that jacked us around before that. It is like, I'm not going to hold a grudge forever, but at the same time, I don't want to work with partners that are those types of people. I want genuine people that are direct with us and I want to be direct with them and no bullshit. Andreessen was always like that, and they still are today and they're an absolutely incredible partner to us. And I'm very happy to have them and very glad that they came in later.
Turner Novak:
Yeah, and so I think you ended up raising a little bit more money a couple rounds after 2020, you raised, I think, a little over $300 million, $400 million. I'm looking at my notes. Anyways, top of the market. Economy was going well.
What was your thinking going into probably don't need the money, you talked a little bit about competitors, but you raised a big round. What was the thinking on that?
Zeb Evans:
I was skeptical of the markets, honestly. I got asked that question a lot at the time, "Why the hell are you raising $400 million?" My answer was always, "I'm skeptical of the markets. I don't think that this is going to last forever."
I had this conversation with Peter Thiel, and he was like, "I don't think you need to raise this amount of money. I think you can have less dilution." I told him, I was like, "Hey, I'm skeptical markets." He's like, "You know what? I think you're right. I don't blame you."
Sure enough, it was the absolute perfect time. I mean, it was October, 2021 when we closed that deal, and November/December was when the markets started falling.
Turner Novak:
What has it been like, I guess, working through all these different, I don't know, stages of the business, investor interest, economic environments, I don't know, any reflections on just, I mean, you've kind of been building in a bunch of different modes at this point. Any big takeaways?
Zeb Evans:
We went from one of the most efficient businesses that investors had seen before. Very profitable, very cash flow positive, to the other side of the spectrum, grow at all costs mentality. Those are two very different ways of building a business. I think it's better for them to work in harmony together.
I actually think that early on it is much better to have very scarce resources. The thing I was actually just telling our company too, I was like, "Less resources ironically make you more resourceful, with actually full of resources because you are also resourceful in the traditional sense." That is what we've rotated towards now is we create scarcity even when we don't necessarily need to create scarcity. Where we don't create scarcity is on acquisition marketing, where we know assuming that unit economics are good, obviously, and when unit economics are good, that is a great way and your retention is good, which is the only way your unit economics will be good anyway.
When unit economics are good, and when your retention is good, that is a great way to raise a lot of money and spend it wisely, is acquiring customers. I think that's the reason you should raise a lot of money, purely that, plain and simple.
Outside of that, I think you should build the business and a little bit of scarcity mode. When you feel like, and people tell you, "Hey, this is crazy, we need another person to do this or we need to buy this to do this," I think that's when you say yes, rather than just trying to grow in order to grow because that's the traditional thing to do or that's what looks right on paper.
I think that's what we've come to now is really building a very efficient business that also, is very scalable and is able to grow very efficiently and net positive and cashflow is really what we're very focused on.
Turner Novak:
Yeah, cashflow is always important to focus on.
Thinking about, it was probably about a year later ChatGPT launched the world kind of changed. I don't know how exaggerated of a statement that is, but generative AI was a thing that people are like, "Okay, we can use this in our products." Have you seen any use cases? I think you were one of the first to actually launch in production utilizing generative AI. Am I remembering that right?
Zeb Evans:
Yeah, for sure. Classic product iteration, moving fast, winging it. Yeah, so we were definitely the first in our category to launch a lot of these features. The obvious stuff is writing tools is very obvious. It's table stakes, it's everywhere. We got that out the door immediately.
What I focused more heavily on was mission focus. How do we enable people to be more productive? A lot of people have work about work constantly. They are writing updates. We built an AI project update builder and writer experience that is not BS. It actually will replace a lot of the reports that you write and the updates that you write on a day-to-day basis.
We built a standup replacement, so where it automatically writes your standup for the day and posts it somewhere. We built a ton of project management automation with AI being able to automatically assign tasks to people and automatically change statuses.
The hard thing that we, and of course, we did generative AI and RAG, so you can ask questions about any of your data inside of ClickUp. I guess I say, of course, but still a lot of our competitors, most of our competitors don't have that.
The really cool thing though was I acquired a company about three years ago for enterprise search, universal search, being able to connect all of your applications in one place and search them from one place. That is at the heart of our current revolution when it comes to what we're building for AI because we are connecting all of your other tools now outside of ClickUp. If you use email or if you use support ticketing like Zendesk, if you use Google Drive or Figma or GitHub, really any of those top tools we connect with, and it's not surface level.
Our infrastructure took those three years to build. More people will build this and Glean has built this already, but everybody else advertising this, it's very surface level. They're using APIs to connect things back and forth and searching as it's happening. Whereas, we index every single object and all of those other applications and put them into a universal data model database. You can perform RAG and AI and a lot of really cool functionality on top of all of your data.
I think that that will become a big moat for us, but also for those customers and being able to leverage AI for real things rather than just writing. That's what I'm focused on, is I think writing is one of those things that gets leapfrogged by your machine, and I think that's becoming more obvious now, but when I said that when we were first building, that wasn't as obvious. I was just kind of guessing.
I do think that writing is one of those things that it doesn't matter right now from a B2B perspective and trying to sell that to customers. There's no moat there. Really, the moat comes to the functionality, the experience. It has to be where you're working also, which we have a great benefit from, and the data, of course, the data is the real moat, it's the actual stuff in the database.
Those are the things that I think that really matter for creating long-term differentiation with AI. That kind of brings us to our next phase of ClickUp, which is the thing I really wanted to finish for the past several years is chat and video calling, communication. Communication is the actual number one used product inside of most companies. As far as active usage goes. It's really the only thing that everybody, regardless of your role has opened on your computer pretty much all day.
Turner Novak:
You guys have never had it?
Zeb Evans:
No, we had a very surface level functionality for chat, but it wasn't real chat replacement. It was like the 10% MVP that we wanted to build and we rebuilt it all from scratch and made it very, all of those lessons we learned from the past about having extremely great performance and front end first and storing all of the data locally. That's what we did. We built it in the best way possible and learned from a lot of our mistakes.
What we benefit from by putting it inside of our product is that convergence theme that I was talking about. All of our other features now work flawlessly with chat. Inside of chat, you can create a whiteboard and collaborate with people, you can create a doc and a knowledge base.
Obviously, you can create projects and tasks, but AI is a huge usage benefit that we're seeing with our chat product now. I mean, it's just used exponentially greater than it was before. Because before, you had to go think about using ai. Now, we do it a lot for you. If you ask a question in a channel, we answer that question for you with AI, if we're able to answer it, a bot comes in and says, "Hey, I have this answer. You didn't really need to ask this to this channel and annoy people and ask the same question that was asked 14 days ago at a different channel."
Turner Novak:
When you're sending it, it will intercept and give you a response before pushing to the channel?
Zeb Evans:
Right now, it does push to the channel because that we think the first iteration the right way to go because you still get the immediate sense of it, you get the transparency from somebody else seeing it. Also, people start to learn about AI answering things because AI comes in and answers it. You see the virality from the answers happening and interacting with that bot.
The other thing that we do is one-click task creation, you can convert any message into a task and it uses AI to do that. It adds an AI summary, it adds a link and a reference back to the comment and it adds an AI title and it also, looks at all of the other contexts in your workspace to relate it together with that.
If you create a task about this podcast, for example, if I message about this podcast in a channel and create a task, it will pull in the doc that we have about information about the podcast. It'll pull in the meetings that we have about the podcast. It'll pull in any other tasks or chats that we have, and it puts it all kind magically together. This is, honestly, what I really feel like is the first really great 10x efficiency benefit from, at least in the work context, for AI, is what we built, and so I'm very, very excited to launch this.
Turner Novak:
When does it launch?
Zeb Evans:
We're launching on the 18th.
Turner Novak:
Oh, amazing, so this is next ... So people are listening to this while it's out there. We'll make sure to throw a link in the notes to the show. Just people when they're listening to this right now, they can scroll and open it up and check it out.
Zeb Evans:
That would be awesome. I'm very excited to get something in people’s hands.
I think its, again, the 10x productivity, what I look for with AI. And there's so much smoke and mirrors around AI right now, and there's a lot of bets people are taking with it that we don't know if we're going to pay off or not. In work management sense, there is really a lot of functional things that AI can do that it isn't doing right now. I'm very excited to make people more productive with it.
Turner Novak:
Interesting, so you said people are taking bets that might not pay off? That's a little concerning. What are some of those bets do you think that may not be paying off for people?
Zeb Evans:
I look at it more in the VC context honestly, is I think that VCs are taking a lot of bets that probably will not pay off and that get leapfrogged to some extent.
Also, the biggest thing that I worry about, what I think will happen is everybody argues how fast and how much more efficiency we'll get from developing and building product like coding with AI and designing. I don't know the answer to that, but I think everybody agrees that you'll get more efficient and be able to build software faster and faster over time. When that happens, it's very hard for me to see how startups exist in the same way that they do because you used to have differentiation from the time that you built, like that was remote was you had two or three years that you built something and you go launch it.
Now, if these huge enterprise companies can build that in weeks or months, that differentiation isn't really there anymore. How do you really create a startup that has a long standing startup that is able to sustain on its own without competitive interference? I don't know how that's going to happen, to be honest. I don't know how that will play out. But my theory is that it will play out in the sense of you have these super apps.
Unfortunately, this is what we've been building since day one, but you have these super apps that exist that build all functionality for a given customer base or category into one platform and you use one platform rather than a bunch of them. I think that it'll be difficult for startups and I don't know how things will change over time, but I certainly also believe that most of the models that exist in the future and all the ones that are most of the ones that are being invested in today won't really create a business out of because these things will become AWS services and Google services that you're paying.
There's no big margin that you have anymore on the compute cost versus the additive fee that you're adding for the model. Instead, you're just really paying mostly for compute cost with a little bit of margin on top of it. I think a lot of this stuff will be hosted on yourself, but also you'll be able to host them even in your web applications. What we're starting to look at right now. I certainly see a lot of the investment and a lot of the time going into this as just not really mattering as much in the future.
I also, in some sense, hope that I'm wrong in that there is a huge tech startup ecosystem where there is some differentiation there. I hope that startups will be able to benefit from a lot of the things that enterprises will benefit from and being able to build faster.
I hope that enterprises don't have a different arbitrage where they can build 100x faster and small startups can only build 10x faster because I think startups can always still move faster. I hope that they'll be able to go build that thing faster and iterate faster and innovate faster and still really build something fundamental on their own, but at the same time, I certainly see the future of more of super apps rather than individual products.
Turner Novak:
Interesting. Yeah, you could maybe argue on your speed. You could say there's all these efficiencies and speed gains that happen, but big corporations still have big corporation problems, so it actually enables the startups to move even faster than they already could. I could see that as being a case of this or a result.
I think too, just to your point of competitive positioning, I think for me what I look for a lot is serving a new customer. It's not a line extension of a coding thing, it's just part of ChatGPT, or it's just part of GitHub co-pilot. You’re serving a new customer that doesn't really have software tools yet. An incumbent just can't be like, "Oh, we're going to add a new feature," and it kind of kills a whole market map of startups.
I don't know, those are just different places that people usually don't talk about healthcare or something like that, or a plumber. The software is now useful for him because is we've unlocked new interfaces that he could use just while he's plumbing or while she's plumbing, so that's how I kind of think about it.
Zeb Evans:
Yeah, I generally agree with the asterisks that our software is built so flexible that we actually have a lot of plumbing businesses and health cares and hospital businesses using our software and they are able to build their own solution in it. I think that there are certainly those very functional things that we're not going to build the patient scheduling system and-
Turner Novak:
That's good. That's one of my AI investments is patient scheduling, so there we go.
Zeb Evans:
Then that's good. See, that's good, that's great. You're exactly right. I think for doing that, it's picking those things that you really need context for and opinions for and focus on that area. There are going to be a lot of those things to be clear. Yeah, I think those are good bets.
Turner Novak:
Yeah. Well, thank you. I was thinking while you were talking, I was like, "Man, maybe I should just put my entire fund in ClickUp," 'cause you're going to beat everything, but maybe not. Then maybe if I'm doing stuff that you think is still going to survive.
This has been an awesome conversation. I want to kind of close it out. You're probably one of the people that seems to be the most passionate about and consistent and adamant on the effects of journaling and having a routine. I've heard you kind of talk about it a little bit before, but I'm curious if you can just talk about journaling and why you do it and why it's beneficial?
Zeb Evans:
Yeah, and I've journaled now for 11 years, every single day. I never miss a day. It's the thing that really has kept me, I think, honest with myself.
But the key to journaling, well, first of all, I would say to get started, it doesn't matter what you're writing, just write what you did that day to start. That's what I did early on. I literally just wrote what I did that day. Over time it turns into your own kind of work of art where, for me, it's around lessons that I've learned. It's around feelings that I have. It's around things that I'm considering doing or not doing. The unique insight, the unique perspective and I think the unique value that I get and that you can get from journaling is going back and reading your journals. At the end of every year, I take a week and I read every, well, I used to read every single journal that I did, every single page from every single journal.
Now, I read the last five years, and I look at the summary that I have of all the big points from the other one. I keep add ... For the next year that's going to decay and time. I basically have notes from that one that gets added so I can still get that the next year that I'm doing it, but reread the last five years and you learn so much. You really just re-learn so much.
I think so much that you learn, you just forget about. And you go back to where you are thinking in that emotional state. I think you gain a new gratitude for the place that you're in right now too. Anybody that is focused on growth and personal development, five years later in life, they're going to be better than they were the five years before. At the same time, that five years later you may not even know it.
I'm guilty of that too, or I still am not ... Like there's so many problems I've got to solve. I'm focusing on these problems. The goalpost always moves. For the people that want to grow, your goalpost always moves. When you go journal, you look back and you're like, "Holy shit, I'm 100 x better than I was five years ago. Wow, I'm so grateful for this." It puts everything back into a different perspective.
That's my big routine. I do other routines. I got diagnosed with narcolepsy many years ago and I've tried to hack it as much as I can. It was simple things. Honestly, it was also sleeping less rather than sleeping more, which is so stupid when you say that.
Turner Novak:
That doesn't make any sense.
Zeb Evans:
With narcolepsy, anybody would know that has this, if you sleep 16 hours, you feel the exact same as if you sleep eight hours. You feel the same. You're always tired when you wake up, your brain doesn't really rest in the same way.
What I did was I started sleeping – and I don't do this anymore - I sleep six hours now, five and a half, six hours. But I used to sleep four hours, and that didn't scale. When I trained myself to do the four hours, I swear I didn't feel any different. I was still tired when I woke up, but I didn't feel any more tired than if I slept eight hours. I was still there. I was like, "Hey, why not just not sleep that much?"
Then over time, when I got in that exact routine of the exact time where I was sleeping every night, I actually did start to feel less tired when I was waking up and I still do today. Then I was eating less and not eating in the morning really. I do juice and usually protein smoothie now in the mornings and I didn't really eat lunch and I eat at the end of the day.
Food for me contributes to the narcoleptic feeling and making me a little bit more tired, especially red meat. I didn't eat red meat for many years and still rarely eat it. Those things really added up, along with journaling, to enabling me to not only do a lot of personal development but not lose the personal development, not go back on the personal development, which I think is really important. You want to go like this, in this direction rather than kind of go like this and then down and then this and then down. You really want to peak, plateau like that. I think too many people, they lose a lot of the things that they learn and I think journaling is a great way to not lose it.
Turner Novak:
Fascinating. Are there any AI tools for journaling or do you still do just writing it and reading it?
Zeb Evans:
I do pen and paper. Everybody thinks that I would do the AI tools and things like that. Well, to be clear, I do have all my journals scanned just so in case there's a fire or something like that, I'll still have them. When I read them and write, I do it on pen and paper. It's the thing I want to get away from, the only time I have to get away from technology, you know?
Turner Novak:
I got to try it. I've been intrigued, specifically, hearing you talk about it in the past. It was just so adamant. I think I'm going to start doing it and this is the inspiration for it. Well, this is a lot of fun. Thanks for coming on the show.
Zeb Evans:
Yeah, this was awesome, Turner. Thanks so much for having me.
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🎧🍌 How ClickUp Bootstrapped to $10m ARR + Scaled to 9-figures in Revenue with Zeb Evans