How ClickUp Bootstrapped to $10M ARR and Scaled to 9-Figures in Revenue

I invited Zeb Evans on my podcast. He’s the CEO of ClickUp.

We had a wild conversation about his 6 near-death experiences, running a business that got FBI attention when he was a kid, and driving Disney monorails.

We also dove into ClickUp’s journey from bootstrap to $10M ARR, their lightning-fast AI rollout, and why he loves hiring users. We also got into their new chat product and how software’s all merging into one.

Video

Watch the full episode on my YouTube Channel here.

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Transcript

Zeb Evans: We never had early on crazy insane growth, but that growth was compounding. But to me, it didn’t feel like we were ever successful, and I didn’t really have anything to go on. We didn’t have investors. We were growing 30, 40% a month, and we had gotten to close to 10 million in ARR. But I didn’t even know that we were doing well.

Turner Novak: Welcome to the Peel. I’m your host, Turner Novak, founder of Man Capital. Keep listening for my conversation with Zeb Evans and how ClickUp bootstrapped to 10 million and eventually nine figures in revenue.

Zeb Evans: We built ClickUp as an internal tool.

Turner Novak: At first, we talk about his first business, selling products online as a kid.

Zeb Evans: And so I come upstairs, and there are two FBI-looking guys there.

Turner Novak: Why he dropped out of college.

Zeb Evans: A 17-year-old kid put a gun to my head.

Turner Novak: How they got ClickUp’s first customer.

Zeb Evans: We built this script that would scrape all of the review websites and anybody that would give any of our competitors three stars, two stars, or one star. We would try to match up their name on LinkedIn and go message them. And that actually worked pretty well.

Turner Novak: Hiring mistakes, scaling from 100 to 800 employees in a year.

Zeb Evans: We hired people that didn’t care about the company and didn’t care about the mission. And then they hired more people like that.

Turner Novak: That was when they had to rebuild the product from scratch.

Zeb Evans: If we had any near-death experience in our company, it was that period. And that was when I was like, holy shit, we’ve got to fix this.

Turner Novak: Zeb’s favorite interview question.

Zeb Evans: I actually think it’s pretty rare for a product manager to be an exceptional product person.

Turner Novak: Lessons from raising money in 2021 and what Peter Thiel told him.

Zeb Evans: Like, you know what, I think you’re right.

Turner Novak: Being early to generative AI and ClickUp’s new Slack competitor that launched the day before this episode went live.

Zeb Evans: All of our other features now work flawlessly inside of chat.

Turner Novak: Before we jump in, I publish weekly episodes exploring the world’s greatest startup stories. Subscribe and check the show notes to never miss an episode. Let’s talk to Zeb. 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 is a bit different. So, you know, I think I talked to somebody at Inc. who counted it as three, but in my head, it’s six. And, you know, 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 channels to watch TV. And pretty much every commercial at that time was like McDonald’s or something that reminded me of food. And the TV shows themselves did also. Uh, so I couldn’t watch TV because it was just like reminding me of food. And that was on my mind every single day; it was like eating.

Turner Novak: How did you get nutrients at the time?

Zeb Evans: I was hooked up to everything in the book. And, you know, they were pumping everything that was in my stomach out of my stomach. I had, you know, a ton of IVs and tube-feeding things. So it was all done, you know, via the hospital itself. 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. And 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 in maybe other locations in the US. But I was extremely, always obsessed with business and selling things and creating experiences for people. I mean, literally since I was like four or five years old, I was doing that.

Turner Novak: What was the first business that you ever did, the 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. So on my fifth birthday, I asked for wholesale toys. Basically, not toys for myself. I asked for, I want to buy some wholesale toys from Oriental Trading Company. I did and went around the neighborhood selling those things kind of 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 like my thing, you know, on the weekends I would sell, and that was, that was what I was obsessed with.

Turner Novak: What kind of toys were they?

Zeb Evans: I remember we had yin yang necklaces, you know, at the time that was popular. And I had these watches that ended up not working that well. There was a bunch of little. It’s a novelty toy website, right? Company. And they’re still around today in a different capacity. So it was a bunch of like 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, like year or two of trying to sell things.

Turner Novak: Okay, so you went to like the school of hard knocks. Like very hard knocks.

Zeb Evans: Yeah, I sold candy. I got suspended actually in first grade for selling candy to students. So I would bring candy in my lunchbox and, you know, they would use their lunch money that was supposed to be used for actual lunch for candy. And I got. That was my first time I got suspended in school.

Turner Novak: Oh, wow. I had a couple of times I got suspended, not for selling candy. It was usually computer-related stuff. And 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? Like, we should be encouraging kids to do that crazy computer stuff sometimes, as long as it’s not harmful.

Zeb Evans: Yeah, yeah. I mean, that should be celebrated. And I think especially in America, like, we are the creative world where we have the freedom to create, freedom to think, and build. And I think that in school, that was 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, you know, I don’t recall it ever being more than like $100, like, total. Yeah.

Turner Novak: That’s huge though. When you’re in middle school, high school, having 100 bucks, that’s a lot.

Zeb Evans: Yeah, I thought, I thought, I thought I was balling at the time. You know, I was like, I can go buy more candy, I can go buy more toys. And then, you know, flash 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. Like, literally, I think I found them, like, right as they were coming out and I found eBay. So I kind of married those two things together and I found I liked movies. So I, you know, DVDs were huge at the time and that was kind of like the newer thing that was coming out. In fact, I think they were still kind of a novelty back then, relatively novel. But 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 like 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 have happened if I hadn’t gotten. Maybe it would have happened later in life, but I don’t think I would have had the same experiences if I hadn’t had that near-death experience.

Turner Novak: So what was the eBay slash Alibaba business that kind of first really worked? Like, did you have any that, you know, you really cracked something and made a significant amount of money for a kid?

Zeb Evans: Two things. The DVDs. Disney DVDs. Disney DVDs were the thing because for, and now I’m talking about from like 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 were in this club. So I could sell a, you know, Snow White or Beauty and the Beast for like $100 on eBay and I could get them through Alibaba for about 10 bucks a pop. But I, you know, the funny story I always tell is, I was downstairs and my dad calls me upstairs in the voice where, you know, you’re in trouble voice. And so I go upstairs and there are two like FBI-looking guys there. And you know, they look at me and then they look at each other and they just start smiling. They’re just like, oh my God, you know, classic. Because I was selling bootleg DVDs and you know, I didn’t, I didn’t know it really. Maybe, maybe I had like an inclination at the time, but I certainly like wasn’t 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 and, you know, they just gave me a slap on the wrist. And it was a great, like, kind of learning lesson in life. The second thing was Abercrombie cargo shorts. And that was like, you know, it was. Abercrombie was a hot thing when I was growing up. And at school it was like, you know, the exclusive thing. But they were so damn expensive. They were. I think they were $49.50, which in today’s terms, that probably had to be like $200, you know, with the inflation and markup that happens in retail nowadays. But it was. 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: So it was. The DVDs were bootleg, fake. Like, other people were cloning the DVDs, then selling them, and then you were kind of shipping them to the U.S.

Zeb Evans: Yeah, they would come from Malaysia, and 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. I don’t know, it was so weird at the time, but, like, I actually enjoyed, like, shrink-wrapping. It was creating the final product. You know, it was like this tangible thing that went from no value to turning it into, like, a tangible hard good with actual value. And yeah, obviously, in hindsight, you know, packaging that together, you would know for sure that, like, they’re bootleg. But again, I was like, 11 years old, you know, so I didn’t. I was more naive than I am today.

Turner Novak: Okay. And then the cargo shorts were kind of 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’re postmarked from Sri Lanka. Abercrombie’s factory at the time was in Sri Lanka, and it would say Made in Sri Lanka on them. And so they would come with the labels, shipped separately. So still today, you have to kind of ship to import stuff. You’ve got to basically take the label off in many, many ways when you’re importing apparel and would ship the labels 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. You know, 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 like a, that’s kind of a, that’s a scary one for, I mean, the person in the factory that’s shipping those out.

Zeb Evans: Yeah. And I think, you know, the context, though, of 25 years ago is 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. So it was, 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. There’s a question from David George on your board at a16Z. He said, what’s up with the shirts?

Zeb Evans: You know, I, 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 go, I always zag the other way. And so I’ve just always been, I don’t know, unique in some way. So I, you know, found some really ridiculous shirts like this one. And I would wear them to the office in 2018 and 2019. 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? No. Are you depressed right now?” So I basically kind of pigeonholed myself into having to wear crazy shirts every single day. But you know, a lot of the irony here is that I also don’t think about what I wear each day. Kind of going back to how Steve Jobs did it, and lots of people don’t. 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. But 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, like, you know, my brand across, so to speak. And so now it’s kind of just part of who I am.

Turner Novak: Yeah, that makes sense. My wife always gives me a hard time about wearing. I just have basically black T-shirts and just like startup swag from portfolio companies and stuff. And I got, you know, plain, plain kind of crew neck sweatshirts like this. So, but yeah, 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, and 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: So when I was 20 years old, and by the way, it was flash forwarding, so we’re skipping a lot. So I’ll give a quick digest: I went to Virginia Tech, and 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 like expected to go to college by, you know, by everyone. Right? By society, by family, by friends. Like everyone expects you to go to college. And I was just one of those kids that did not want to go to college. Like 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 that 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 are exceptions to everything, right? So like take, you know that, take that as like the 80% case. The 80% of school for me was totally worthless and useless. And you know, I thought college would be the same way. And I went to, and I had started a, I became a DJ at the end of high school, and I started a mobile DJ company that was like my most successful early, early company. The margins on that are actually insane margins on mobile DJing for like sweet sixteens and birthday parties and things like that.

Turner Novak: What’s the rough economics like? Is it like a little bit of spend up front and then just like, just pay for your time basically?

Zeb Evans: Exactly. So the spent, the cost is just the equipment. And you know, the equipment is actually not that expensive. I mean, it would be $100, $200 a speaker; you need a couple of speakers. I used a computer, a laptop, and I would very much, you know, charge anywhere from $300 to $400 or $500 an hour. Now it takes an hour or two to set up. So, you know, all in. There are 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. And when I went to college, I 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, not actually teaching you how to do all of the tactical things around accounting. So I never went to class after the first day; I was like, this is just totally useless. And I worked on businesses, I worked on my— I created an entertainment company there and, you know, 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 the 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. But I found this Disney program, Disney College program, and I applied to that and I was like, you know, I always admired Disney for customer support, and it was something that I looked up to and a company that I looked up to for how they treated customers. And so I went there and I drove the monorail and I actually loved it. I lived and worked there, and it was intense. I mean, it taught you discipline. If anybody’s been through that, I don’t know if it’s like the same thing nowadays; they probably got in a lot of trouble for how much they pushed people. But, you know, back then it was extremely intense and it taught me a ton of discipline and hard work and how to deal with customers that are so angry and frustrated and being able to empathize with them and still kind of put a smile on and not have it affect you in your day-to-day.

Turner Novak: So this was like 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. And so, I mean, what did they teach you on customer support and, like, you know, being happy in customer service? Like, it sounds pretty straightforward. Like, 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 and being empathetic with them. Because I think if you’re not taught that, you go there and you see, you know, these people that are supposed to be in the happiest place in the world, they’re at Disney World; why aren’t they happy? You know, why are they complaining about, like, 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. You know, they don’t get to go often, 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, like, 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 kind of 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. So I think 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. You know, 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, you know, 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. Yeah, I mean, because your point, I mean, we’ve looked up, because we have kids, we’ve looked up how much it costs going to Disney World, Disneyland. I think at this point it’s like 14, $15,000. If you kind of are a family of four doing the full couple of day trip from out of town, you’re flying in, you’re staying at the hotels. That’s like 20% of annual income in the US, like that is of median annual income. That’s a lot of money for some.

Zeb Evans: Families, a ton of money. And 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. So 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. And you know, I think that Disney is honestly, they don’t treat employees well at all. That’s what I saw; they’re a terrible company for employees. And so that was like one of the big insights that I had also is like, I want to take what they’ve done from a guest experience perspective, put it in our company, instill a lot of those values, but also treat employees right. 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 like a bad boss or bad experience and you’re, you know, you take the opposite approach in the future. You know, you’ve seen all the ways that it goes wrong. Like, all right, I’m never going to do that again. I’m gonna do the opposite. So when you say you really then care and value your employees at ClickUp, what does that look like?

Zeb Evans: First of all, the biggest thing, which sounds almost kind of dumb saying it, is to have managers that care, managers that give a shit. And I think that really, really, really matters. And 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 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 family with their team. But if you have that happen, you’ve over-rotated in the wrong direction and, you know, 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 like one of the biggest things to get right: having managers that care about the team and care about the company.

Turner Novak: I’ve heard the analogy is you don’t treat them like a family; you treat it like a sports team where it’s like you all work together, you know, people bring the skills to win, basically. And I think the sports team one is an interesting one where it kind of makes more sense than the family.

Zeb Evans: Yeah, we say crew because it just sounds good saying click up crew, but you know, 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 like a sailing crew, and you know, everybody plays their part, and if somebody’s not playing their part, give them the opportunity to understand what’s wrong, give them the 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, you know, iterating on your team. And I think that’s really important. It’s also really hard to do for managers. Right. It’s like 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. And you never want to have back in school when you had these group projects where, you know, one person is pulling all the weight, and the other person is pulling the team down. Like you can’t have that at teams. You’ve really got to have A players all around, and 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: Like how did that go?

Zeb Evans: Terrible. There was an opportunity I had like a year and a half ago where I realized what had happened, and really, for that scaling period when we were growing really fast, we grew from like 100 to 800 employees in a year. Everything that could go wrong did go wrong during that period. But the biggest thing that went wrong was hiring the wrong managers and the wrong leaders and 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 kind of have to be political in the work sense and, you know, make yourself look good and build your empire up to show, you know, how many people you were able to manage. But it’s a really bad thing for startups and those people. A lot of these lessons, you hear anecdotes from before, you know, like 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, you know, with. And 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, more importantly, about our mission, which I truly care about. It’s not one of those missions we just make up and, you know, 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, this isn’t the right place for them, where we are focused on this mission, not other, other missions. And I think that was like. 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 a 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 in 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 everything from a different one that I use into ClickUp that I have 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 was. I’m like I’m going to give ClickUp a try because I’m having Zeb on. I want to see if I can shift everything over and try using it. So I haven’t gotten 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, you know, 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: 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 gonna get myself to switch from. We were using 15 productivity tools at the time. I mean, I was obsessed with productivity, still am. And so we used like one tool for kind of like all of the best-in-class everything. And, you know, 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. The first thing we built, a feature we built in ClickUp, was one data model 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, you know, been on day 1,000 in another tool.

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Zeb Evans: Yeah, so when I was after. 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, 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 like 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 do 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, that literally in my head, I was like, if I survive this, I will drop out of college, and I will go focus on business. Which I knew in my heart was the thing that I was meant to do. I meant to build in this world was to give jobs, 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 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 with those 15 different productivity tools using that. And I wanted to move on to something bigger. I knew that we were not really changing the world, as cliché as that sounds, you know, but it was more so in the sense of like, are you having a 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: Yeah, and I was obsessed with saving time, and I was like, you know, why not, 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 can 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, like, a public transaction there and give reviews on that public transaction. Yeah, maybe they do now, but if they don’t, I’m going to start this at some point or somebody. Somebody listening to this podcast should 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. Let’s go full and all in on this. And we totally forgot about the Craigslist thing and focused on ClickUp.

Turner Novak: So why was it important to be able to switch back and forth? ‘Cause it, I guess, doesn’t seem like that big of a deal. Why? 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 wanted to be able to look at a list. And then we also had bugs and other ticketing in Jira. Right. So all the engineering stuff was in Jira. And, you know, the insight that I had, which I didn’t feel like was revolutionary, but it was just. It was that, hey, this is all the same data model behind the scenes. And just. It’s a different visualization. Like, 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 it was. That led to a lot of our early growth, was really just having that unique differentiation while it lasted, which was probably like two years or so before everyone else started building it, really.

Turner Novak: Okay, so then what was kind of the next? I know at this point there’s a lot that you kind of incorporate. What was then kind of like the next leg of the product, besides just being able to switch between different views? Like, 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 kind of 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 it wasn’t—we’re not talking about like CICD 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 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; 22 really was kind of when we ended up building most of it in 22. 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 I talked about in feature parity, really getting to a point where the products themselves are actually usable and replaceable. You can 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 replatform and re-architect and rebuild a lot of 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 on your—wherever you were in the world. If you’re logging on to ClickUp at your local time at 8 a.m. when it’s peak traffic, ClickUp would be generally unreliable and in many ways unusable for the first hour or so of your workday. 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, you know, 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, I guess, and how did you get out of it? Like, 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 were not, we didn’t have different databases for sharding, for having different data in 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: Oh, so you just, 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, we 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 here. It would create a lot of data problems, and it would make it appear there was data loss even when there wasn’t. And it would transpire with 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, you know, 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 in 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, you know, the synchronization was actually happening.

Turner Novak: So then how did you, how did you get out of it? Did I mean, it sounds like you probably just rebuilt the whole architecture. Like, is that how you got out of it or how’d you do it?

Zeb Evans: We largely rebuilt everything, and on the infrastructure side, you know, we went through sharding and micro-sharding and are now enabled to really scale databases by the horizontal approach. Right. 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. We couldn’t really. Everything else was cherries on top, things that we could patch but not totally fix. We had to go through sharding and really a re-platforming as a whole. And we also had to become operationally competent in managing these databases. And it’s, it’s, you know, 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 are a lot of variables, like permutations, in the way that things can happen and interact that you can’t always predict until you kind of start seeing things in production and finding the problems and fixing them. So yeah, that took us a good, you know, over a year, a year and a half or so to get through that. And I think the other, 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 you know, I didn’t really know why; I wasn’t, 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. You know, I would find memory leaks and things like that, but we couldn’t really pinpoint exact things. And I had, after we scaled to that, you know, 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 like a few people.

Turner Novak: Yeah, half, like 50-50 at least or something; who knows?

Zeb Evans: Yeah, just to make the point of like, hey, we probably need more front-end folks. Zero people raised their hand. Literally zero people raised their hand in this management meeting. And that was when I was like, holy shit, you know, like, we’ve got to fix this. And we did. And, you know, 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, it took us a while to fix things and to turn it around. And, you know, 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 at a competitor, come work on this product that’s kind of broken. Like, I’m assuming it was a better pitch than that. But, like, 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 that also feel, I think when you do the 0 to 1, the 0 to 1 people are different than like the 1 to X people. And Microsoft Teams, for example, was 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 could, and they felt like that they, you know, of course Microsoft benefits from like infinite distribution for free, but they didn’t know that they were going to be successful just through that. Like 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 were 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 like 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, come 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 you know, 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 like 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 that I was talking about at 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 know, you give them the pitch, 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 solving for. It’s going to be hard, you know, all that kind of stuff.

Zeb Evans: Yeah. And I think the hard piece is something that really, really matters is finding people that want to do hard shit. And the only way that I found that everyone will say that they want to, generally speaking, some people will actually be very transparent and say like, hey, no, I want to in life right now. And it’s not my thing. But most people will say, hey, yeah, of course I want to do hard, hard shit. But I find that that’s not always true. And hard is also very subjective. Right. It’s like it 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 always, and every manager 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 they answer with 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 who 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 that people who 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. And I always ask, like, hey, what was something positive? Was there anything positive that came out of that? And sometimes people will say like, 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: Yeah, just the ability to reflect on the things happening and learn from them. I mean, you gotta be a learning machine if you wanna be at a startup. I mean, things are always changing. You gotta be moving quick, too. One thing I thought was interesting that I’ve heard you mention before, going back to kind of the days of getting ClickUp started, you guys did 5 a.m. stand-up meetings every morning. Talk about doing hard stuff. Tell me about that. That just sounds very intense, but it sounds like it works.

Zeb Evans: It was extremely intense, you know, 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 I was, you know, 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 showed up.

Turner Novak: You Googled Silicon Valley, and Palo Alto showed up. Wow. Okay.

Zeb Evans: Sort of. 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 like Reno with startup lights, you know, just like startup, startup, startup, startup. And Palo Alto is like the sleepiest place in the world.

Turner Novak: Yeah, just like a little suburban, little single-family homes, like ranch style.

Zeb Evans: Right. And they have, like, an ordinance there. You can’t have signage, like, much signage at all. And so we couldn’t even find any companies. You know, we’re like, what the hell is this? We got bamboozled. But we looked at offices there, and they were so expensive. I mean, it was like 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 in 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, you know, 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. And, you know, there were a few. I was like, look, we got to be extremely healthy. It means eating healthy; it means exercising. We are going to do 5 a.m. 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, you know, and we weren’t 100% perfect on it, but if I had to give a score, I’d give us like 95. And it was incredible. I’m very grateful to those people early on for actually doing that. I don’t think we would have been successful otherwise because the category would have. I mean, our category goes so fast as far as iterating and innovating, and it’s a lot of kind of like copycat in our category, you know, where it’s like, we build something and then our competitors build it, and then, you know, 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. I don’t think we would have 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, I just basically, they both wake up at like 6 a.m., so it’s just whenever they wake up, I wake up, no alarm. But they wake me up every morning super early. So I was going to ask you, as you were getting it, I was like, wow, super. Yeah. 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, in any competitive category, you have to do everything right. Like, 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’ve got to do product right; you’ve got to do engineering right; you’ve got to get talent right. All of those things have to be done right 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 like a decent product, but like some unique insight into go to market. In a non-competitive category, you can kind of 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, especially when you’re starting out and you’re not able to hire, you know, 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 mentioned before, like it was kind of pretty scrappy. Literally messaging people, trying the products. Like what worked kind of the first couple hundred people? I don’t know what you consider like the 0 to 1 stage, but how did you get people to start using it?

Zeb Evans: Initially, 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, or 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. Usually, they were the buyer; you know, usually it was the person that bought the product that was writing that review because they were pissed off. It wasn’t like the user. So it actually was a really good way of contacting the buyer, and they appreciated the hustle and the grind. And, you know, even though that was like six, seven years ago, there wasn’t a lot of it—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. Like it doesn’t work. But.

Zeb Evans: But that’s one of the things. Those are the types of things that we would do. And you know, we would do SEO, right? We would do a lot of content. And so we never had early on any spike, anything that was just like, oh, this was crazy, insane growth for these 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 30-40% a month in revenue, and we had gotten to close to 10 million in arrangements on our own bootstrapping. And we didn’t spend any money on marketing really, at least on like acquisition, 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. Like, did people just retain? Was it really sticky? Were they spending a lot of money? It sounds like the growth was consistent. Like, why do you think it worked early on? If you could go back reflecting on it.

Zeb Evans: It’s now; we definitely had the adoption. The adoption piece matters more than anything, like retention; our users 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, you know, 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: user metrics, like, 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. I was just honestly kind of winging it because we didn’t have, you know, all of the data tools that you have today to 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, like one of the biggest things we got right, and we still do a ton of today: surveys. We do short surveys; we do 60-second surveys asking people a couple of questions. And 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 made a lot of the paywall decisions. I would ask them, “Hey, you know, 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 on paywall and packaging, and, more importantly, on product. We do a ton of surveys today too, asking how people feel about a feature that we release. We look at the data for sure, but also the qualitative thing is the thing that matters to me more than anything: the details of why or why not somebody is using it and what else they want on top of that.

Turner Novak: So if I’m listening to this, this isn’t 2017 when you’re figuring it out. This is like 2014 today. How do you do a good survey today? Like, 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 processes just to make them 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. Like it was me writing the questions.

Turner Novak: Because this is like customer discovery; this is like customer feedback that you’re getting, so like very in the weeds. Like it’s good, good stuff from customers.

Zeb Evans: Yeah. And it’s using, you know, we used to use Typeform. We use ClickUp Forms now, and we have great reporting inside of Typeform. 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 are a lot of survey tools out there. I do think it’s important to use 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 just launched a new forms experience that gives you this single question. But honestly, I think it’s even better than what Typeform does, and it gives you that really high conversion on finishing the survey. Really, that’s the whole goal of the survey: to get people there and then fill it out. So I think using a survey platform that has high conversion and asks very simple questions—really simple questions—is crucial. We now do this with AI, where we take the questions that we have and create a prompt to make it simple. But it’s really important to ask questions—super, super simple questions—like dumb it down as much as you can, and 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. You know, 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, pretty simple. You can do. Do you reward people? Like, do you give any benefit or?

Zeb Evans: No, no, but we 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: bringing the community along for the journey. Like you really have a vote in 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 because you kind of. I just think about this fragmentation, all this different software and tools that are out there. If you go to the ClickUp website or if you use the product and you’re in it, there are a lot of things you can do. So I’m curious how you’ve thought about A, kind of this whole consolidation of software that’s kind of happening. But then B, what are some of the interesting use cases, like the most surprising types of customers that you’re seeing on ClickUp?

Zeb Evans: The word that I use is convergence. And we, we always, when I talk to investors early on and even when we were first raising, there was this theme of like bundling versus unbundling and consolidation. No 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: Yeah, because that sounds kind of shitty. Like it’s like we’re going to just bundle on like, you know, 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. Like 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 it wasn’t. 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 on 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 having their own opinion about how they work. I don’t think that’s an efficient way of working. And we certainly have seen that. And in some productivity analyses, like you’ve really got to enforce structure in 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, 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 like the magic retention happens for us, where they just, they retain and their active usage goes up heavily. The third thing for us is services agencies; a 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, which 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. You know, 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 timesheet 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, I was like time tracking. What the… Why this? Like, this is a mistake. Like, why is this in here? That seems kind of odd. But I guess it makes sense. Yeah.

Zeb Evans: And it is a mistake to show time tracking to a lot of people. To everyone. And that’s something that you learn with experimentation: try to show it to the people that we think are going to be served, the 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, you know, 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, 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 are all these downstream metrics that also increased. So that’s what we focus on now. And if you had to ask me how to run this, I would have 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, like, solutions and, you know, 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. It was like, 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 wouldn’t. I would not have gotten those same if I had picked, like, I’m a VC or like, I’m a marketing person or whatever. So then, just in terms of like, some of these, like, different product things that we’ve talked 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 scaled myself. And so I’m a product founder, right? 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. Right. Like every. Every single detail was being designed and created by me. And so then naturally, you 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 are exceptions to literally everything. So 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. You know, I just wouldn’t consider a lot of product managers as product people.

Turner Novak: How does that happen? Like 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. We certainly have really great, experienced product managers today who are great product people. But generally speaking, I think the best way to hire product managers is by hiring your users because they’re the ones who have felt the pain and the benefit of your product for years, usually. And they’re the ones who 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, you know, our product would not work right; our product organization 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 at this a little bit, but so what makes a good product person? If 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, descoping 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, oh, 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, like you kind of know what the data is going to say, so just go with it. If, I mean, 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, you, you hinted at 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. So we were in Palo Alto, you know, for that first year, year and a half. And then we moved up to San Francisco because we realized, oh shit, 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 to talk to us. And, you know, 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, you know, founders getting fired from their own companies, and I just kind of wanted to control my own destiny. And I really cared about the 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 at the end of 2019, the attention from investors was just so heavy. It was like my inbox was just getting flooded with investors. And so I was like, okay, you know, let me think about this. Maybe we go run a process. But also the bigger thing was that our competitors were raising a shit ton of money, and they were outspending us on acquisition marketing. And, you know, it’s somewhat of a land grab in this category. So I was thinking about it from that perspective also. And so I decided to—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 the 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. Like, what’s, you know, what’s going on? Nobody’s messaging me. I’m like reaching out, like, hey, what’s up? You know, like, what’s going on? I feel like nobody was giving me a straight answer. And, you know, there was. Everybody was just kind of like, 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 know, you’ve got more to validate before we believe that you can be a category winner. And I greatly appreciated that. I 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 I waited another week in San Francisco and finally just like, fuck this, you know, 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, you know, because it felt like I had spent so much time and everybody was like, almost like, you know, forcing me to come up and talk to them. But then like, nobody gave us a deal. But more importantly, nobody told us why. There was no, like, why behind why they wouldn’t do it, 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 have 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, that sounds existential. Different paths the business would have been on. Like, 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, you know, 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 kind of like being on the same team and figuring things out. And there were 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 have been like, you know what? 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 have given me people that are more experienced, and I probably would have hired those people because, you know, like, why wouldn’t you? Right? If you can get somebody that’s done it before and somebody that’s very, like, 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 of months later in May 2020. What happened?

Zeb Evans: Yep. So probably six months or so later, we—well, first of all, it was the very beginning of COVID. Did you see a bump?

Turner Novak: Just curious, like, how did the business change at all when Covid hit?

Zeb Evans: We didn’t. Everyone thought we would. And everyone, you know, said that, you know, like, in fact, sometimes we would get asked, like, are we a Covid business? Really? What? What I see now, and like, looking back, it’s those communication tools that got the bump. It’s like 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, you know, the people that really needed, like, work management software, they were already using it. They weren’t. They weren’t doing it on sticky notes and doing it on pen and paper. You know, they were already using software. So I think there, I think you could argue, and we didn’t see it, but we did always see that consistent growth happen. I, I imagine a lot of that consistent growth happened 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, I buy that for sure. But yeah, we never, we never saw that bump during COVID, and we had Craft Ventures reach out to us. And David Sacks wanted to chat, and I massively respected and respect him today and chatted with him, and it was, you know, supposed to be just kind of a short, informal conversation that turned into a very in-depth conversation, and he gave us a term sheet later that day.

Turner Novak: Wow. Totally different. Yeah.

Zeb Evans: Experience 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, like founder-friendly and founder-focused was so different from most of the VCs that I had talked to before. And, you know, 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. And so, yeah, it was a no-brainer for me to say yes to that deal. And the other investor we brought on was Georgian Partners, who they are. 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. And so those were the two best investors I really could have asked for for our Series A.

Turner Novak: And then, I know, I know, David, you said a16z did end up coming back in to 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.

Zeb Evans: You really respected that 1000%. We didn’t even consider any of the other VCs that jacked us around before that. You know, it’s 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 of rounds after 2020. You raised, I think, a little over 300 million, 400 million. I’m looking at my notes; anyway, top of the market rate, the 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. And so I got asked that question a lot at the time. Why the hell are you raising $400 million? And my answer was always, I’m skeptical of the markets. I don’t think that this is going to last forever. I had that 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. And I told him, I was like, hey, I’m skeptical of the markets. And he’s like, you know what? I think you’re right. Like I don’t blame you. And sure enough, it was the absolute perfect time. I mean, it was October 2021 when we closed that deal. And you know, November and December were when the market started falling.

Turner Novak: So 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. Right. Grow-at-all-cost mentality. And those are two very different ways of building a business. I think it’s better for them to work in harmony together. But I actually think that early on, it is much better to have very scarce resources. And you know, the thing I was actually just telling our company too, I was like, fewer resources ironically make you more resourceful, like with actually full of resources because you are also resourceful in the traditional sense. And that is what we’ve rotated towards now. We create scarcity even when we don’t necessarily need to create, create scarcity. And 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 would be good anyway. A grad is a great way to raise a lot of money and spend it, spend it wisely, is acquiring customers. I think that’s the reason you should raise a lot of money. Purely that plain and simple. But outside of that, I think you should build the business in a little bit of scarcity, scarcity mode. And when you feel like, and people tell you, hey, like, you know, 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. And I think that’s what we’ve come to now: really building a very efficient business that also is very scalable and is able to grow very efficiently. And net positive in cash flow is really what we’re very focused on.

Turner Novak: Yeah, cash flow is always important to focus on. So thinking about it, it’s probably about a year later that ChatGPT launched; the world kind of changed. I don’t know, I don’t know how exaggerated of a statement that is, but generative AI was a thing that people were 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. We classic product iteration, moving fast, you know, winging it. Yeah. So we were definitely kind of the first in our category to launch a lot of these features. And the obvious stuff is writing; like writing tools is very obvious. It’s table stakes; it’s everywhere. And so we got that out the door immediately. But what I focused more heavily on was mission focus, like how do we enable people to be more productive? And a lot of people have work about work constantly. They are writing updates. So 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. And we built a standup replacement, so it automatically writes your standup for the day and posts it somewhere. We built a ton of project management automation with AI, like being able to automatically assign tasks to people and automatically change statuses. And 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. And 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. And that is at the heart of like 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. So you’re—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, and so that will… More people will build this, you know, and there’s like 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 like as it’s happening. Whereas we index every single object in all of those other applications and put them into like a universal data model database. And you can perform RAG and AI and a lot of really cool functionality on top of all of your data. And I think that that will become a big moat for us, but also for those customers in being able to leverage AI for real things rather than just writing. And that’s what I’m focused on; 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 kind of guessing. But 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. And so those are the things that I think really matter for creating long-term differentiation with AI. And that kind of brings us to our, you know, next phase of ClickUp, which is the thing I really wanted to finish for the past several years: 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 open on your computer pretty much all day.

Turner Novak: Yeah. And you guys have never had it?

Zeb Evans: No, we had a very surface-level functionality for chat, but it wasn’t a 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 well. 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. And so we built it in the best way possible and learned from a lot of our mistakes. What we benefit from by putting it inside 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 more than it was before. Because before, you had to 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 in this channel and annoy people by asking the same question that was asked 14 days ago in a different channel.

Turner Novak: So when you’re sending it, it’ll intercept and give you a response before pushing it to the channel.

Zeb Evans: Right now it does push to the channel because that is, 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. But also, people start to learn about AI answering things because AI comes in and answers it. So you see the virality from the answers happening and interacting with that. Bottom line, the other thing that we do is one-click task creation. We can, you can convert any message into a task, and it uses AI to do that. And so 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. So 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 of magically together. And this is like, honestly, what I really feel like is the first really great, like 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: So we’re launching on the 18th.

Turner Novak: Oh, amazing. So this is like next. So people are listening to this like while it’s, while it’s out there, we’ll make sure to throw a link in the notes to the show just so 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 hand. I think it is again the 10x productivity time saver. That’s what I look for with AI. And there’s so much kind of smoke and mirrors around AI right now, and there are a lot of bets people are taking with it that you don’t know if they’re going to pay off or not. But in a work management sense, there are really a lot of functional things that AI can do that it isn’t doing right now. And so 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 like 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. I also, you know, 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 products like coding with AI and designing, and I don’t know the answer to that. But I think everybody agrees that you will get more efficient and be able to build software faster and faster over time. So 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 your moat was, you know, 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. So how do you really create a startup that is a long-standing startup that is able to sustain on its own without competitive interference? And 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. And 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; you know, you’re not really, there’s no big margin that you have anymore on the compute cost versus like 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. And I think a lot of this stuff will be hosted on, on yourself, but also you’ll be able to host them in your, even in your web applications, what we’re starting to look at right now. So I certainly see a lot of the investment and a lot of the time going into this as kind of just not really mattering as much in the future. But I also, in some sense, hope that I’m wrong and that there is a huge, huge tech startup ecosystem where there is some differentiation there. And I hope that startups will be able to benefit from a lot of the things that enterprises will benefit from in being able to build faster. You know, I hope that enterprises don’t have a different arbitrage where they can build 100x faster and, you know, small startups can only build 10x faster because I think startups can always still move, move faster. And so I hope that they’ll be able to, you know, 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 like super apps rather than individual products.

Turner Novak: Interesting. Yeah, you could maybe argue on your speed; you could say there are all these efficiencies and speed gains that happen, but big, 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, you know, competitive positioning, I think for me, what I look for a lot is like serving a new customer. So it’s not like a line extension of, you know, coding thing, is it just like, you know, it’s just part of ChatGPT or it’s just part of GitHub Copilot. Are you like serving a new customer that doesn’t really have software tools yet? So 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. And I don’t know, those are just different places that people usually don’t talk about, like health care or something like that, or a plumber who’s, you know, the software is now useful for him because, you know, 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 like, our software is built so flexibly that we actually have a lot of plumbing businesses and health care and hospital businesses using our software, and they kind of are able to build their own solution in it. And so I think that there are certainly those very functional things that like, we’re not going to build. Like, you know, the patient scheduling system. And that’s good.

Turner Novak: That’s one of my AI investments: patient scheduling. So there we go then. That’s good.

Zeb Evans: See, that’s good. That’s great. And you’re exactly right. I think for doing that is like picking those things that you really need, like context for and opinions for, and focus on that area. And there are going to be a lot of those things, to be clear. So, 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 because you’re just gonna beat everything. But maybe, maybe not then. Maybe if I’m doing stuff that you think is still gonna 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. And 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. And that’s what I did early on. I literally just wrote what I did that day. And over time, it turns into, you know, 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 and 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. And so, 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 a summary that I have of all the big points from the other ones. So I keep that for the next year that’s going to decay in time. I basically have notes from that one that get added. So I can still get that the next year that I’m doing it. But rereading the last five years, you learn so much. You really just relearn so much, I think so much that you learn, you just forget about and you go back to where you are thinking and that emotional state. And 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 five years before. But at the same time, that five years later, you may not even know it. Like, I’m guilty of that too, right? You know, I still am not. Like, I’m like, there are so many problems I’ve got to solve. I’m focusing on these problems. And, you know, there’s. I don’t. The goalpost always moves for the people that want to grow; your goalpost always moves, right? So when you go journal, you look back and you’re like, holy shit. You know, I am like 100x better than I was five years ago.

Turner Novak: Wow.

Zeb Evans: I’m so grateful for this. And it puts everything back into a different perspective. And so 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, too. And it was simple things, honestly. It was also sleeping less rather than sleeping more, which is like so stupid when you say that.

Turner Novak: 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, right? You feel the same. You’re always tired when you wake up. Your brain doesn’t really rest in the same way. So what I did was I started sleeping. 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. But 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. So I was like, hey, why not just not sleep that much? And 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. And then I was eating less and not eating in the morning, really. I do juice and usually a protein smoothie now in the mornings. I didn’t really eat lunch. I eat at the end of the day. Food for me contributes to, like, the narcoleptic feeling of making me a little bit more tired, especially red meat. I didn’t eat red meat for many years and still rarely eat it. But those things really added up along with journaling to enable me to not only do a lot of personal development, but, like, not lose the personal development, you know, not go back on the personal development, which I think is really important. You want to, like, go like this in this direction rather than kind of go like this and then down and this and then down. You know, you really want to, like, peak plateau like that. But I think too many people kind of 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 just write it and read it?

Zeb Evans: I do pen and paper. I do. I like, everybody thinks that I would do, you know, the AI tools and things like that. And I… Well, to be clear, I do have all my journals scanned just in case there’s a fire or something like that. I will, you know, I’ll have them. But when I read them and write, I do it on pen and paper because it’s like the thing I want to get away from. The only time I have to get away from technology.

Turner Novak: You know, I got to try it. I’ve been intrigued specifically hearing you talk about it in the past. It was just like so adamant. So I think I’m going to start doing it and this is the inspiration for it. So, 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.

Turner Novak: And thank you for listening. Make sure to check out the show notes if you want to go deeper on some of the topics mentioned throughout the conversation. If you like this episode, it’d mean the world if you liked, subscribed, commented, followed, and shared it with a friend you can learn from. And if you don’t want to miss future episodes, subscribe to my newsletter in the show notes, and you’ll get links plus a transcript for every new episode emailed directly to your inbox. Thanks again for listening. See you at next episode.