How ClickUp Bootstrapped to $10m ARR and Scaled to 9-figures in Revenue with Zeb Evans

0:00 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 we were doing well 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 bootstrap to 10 million and eventually nine figures in Revenue we built flick up as an internal tool at first we talk what his first business selling products online is a kid and so I come upstairs and there is two like FBI looking guys there why he dropped

0:47 out of college a 17-year-old kid put a gun to my head how they got click Up's first customers 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 one star we would try to match up their name on LinkedIn and then go message them and that actually worked pretty well hiring mistakes scaling from 100 to 800 employees in a year we hired people that didn't care about the company and didn't care about the mission then they hired more people like that when they had to rebuild the product from scratch if we had any near-death experience in our company it was that period and that was when I was like holy we've got to fix this zeb's favorite interview

1:32 question I actually think it's pretty rare for a product manager to be an exceptional product person lessons from raising money in 2021 and what Peter teal told him he's like you know what I think you're right being early to generative Ai and click Up's new slack competitor that launched the day before this episode went live all of our other features now work flawlessly inside of chat before we jump in I publish weekly episodes exploring the world's greatest startup stories subscribe and check those show notes to never miss an episode let's talk to Zeb Zeb welcome to the show excited to be here thanks for having me Turner 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 yeah I count six and

2:21 the severity of them are are a bit different so you know the I I think I talked to somebody at Inu counted it as as three but in my head it's it's six and you know the F 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 for two months and I couldn't eat anything for the first month or so um and obviously when I was 10 that was you know 20 plus years ago 25 years ago and there was no Netflix there was no watching movies on demand and I had to flip through a channel for watching TV and pretty much every commercial at that time time was like McDonald's or something that reminded me of food and the the TV shows themselves did also uh so I I couldn't

3:08 watch TV because it was just like reminding me of food and that was on my mind every single day it was like eating how did you get nutrients at the time I I was hooked up to to everything in in the book and you know they were they were pumping everything that was in my stomach out of my stomach I had you know a ton of IVs and and Tube feeding things so it was it was all done you know via the hospital themselves I you know my brain was going crazy and I didn't like reading at the time I like you know I was taught to read all the books that I felt didn't matter to me it was all of these like Shakespearean you know books and things like that that you normally get in in school and you know there was a a laptop in the hospital and somebody brought it to me and I started

3:54 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 have the same access to to computers that everyone did and and 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 what was first business that you ever did first way you ever made money 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 on Oriental Trading Company I did

4:40 and went around the neighborhood selling those those things kind of door too and then you know got in trouble for going for being too annoying to neighbors and so then I had a stand that I would just sell as I mean that was like my thing you know on the weekends I would sell when I and that was that was what I was obsessed with what kind of toys were I remember we had yinyang necklaces you know at the time that was popular and I had these watches that ended up not working that well um 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 knick-knack no novelty toy style things that I thought were cool but honestly were hard to sell to people and I think I charged way too

5:27 much retail price for them so I didn't really do that much sales I 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 okay so you got you went to like the School of Hard Knocks like very hard knocks yeah I sold candy I got suspended actually in first grade for selling candy to students so I would bring candy in my lunch box and you know they would use their their lunch money that was supposed to used for actual lunch for candy and I got that was my first time I got suspended in school oh wow I had I had a couple times I got suspended not not selling candy it was usually it was like computer related stuff and it was always it was always stupid things that you look back on and you're like why a

6:15 why did I do that but B also why were we suspending kids like we should be encouraging kids to do the the crazy computer stuff sometimes as long as it's not harmful yeah yeah they should stuff I mean that should be celebrated and I think it especially in in America like we are we are the the creative world where we like have freedom to create and freedom to think and and build and I think that in school that was my real struggle with school was that I feel like it was like diminishing my creativity to some extent trying to put everyone in the same box at the same time learning the same things did you make money from the the school candy business it sounds like maybe that was a little bit more successful I I did make money for sure but I mean you know I I don't call it ever being more than like

7:00 $100 like total yeah that's huge though when you're in like middle school high school like having a 100 bucks like that's a lot yeah I thought I thought I thought it was balling at the time you know I was I can go buy more candy I can go buy more more toys and the you know flash being 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 like literally I think I found them like right as they were coming out out and I found eBay and so I kind of married those two things together and I I found I I liked movies so I you know DVDs were huge at at the time and I you know that was kind of like the newer the newer thing that was coming out in fact

7:45 I think they there you know it was 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 on eBay and I created my first we it I used like a whsy wig GoDaddy editor that they had back then you know I just was obsessed with with technology and with business and so I finally married those two and honestly I don't think that would have happened if I I hadn't got 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 so what was the the eBay Alibaba business that kind of first really worked like did you have any that you know you really cracked something and you made you know significant amount of money for a kid two things the DVDs Disney DVDs Disney

8:32 DVDs was 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're 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 whoa but I you know the the the funny

9:18 story I always tell is is I was downstairs and my dad calls me upstairs in the voice where you know you're in trouble voice and so I come upstairs and there is two like FBI looking guys there and you know they look at me and then they look at each other and they just start like 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 um but I certainly like wasn't aware fully aware so yeah they they thought it was my dad because I was using my dad's name on the PayPal account and the e account and and so they came there and you know they just gave me a slap on the wrist and and it

10:05 was a great like kind of Learning lesson in life the second thing was abomi cargo shorts and that was like you know it was Abie 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 I think they were 4950 which in today's term that probably had to be like $200 you know the the inflation and markup that happens in retail nowadays but it was I I could get those for about $15 landed from a a factory through Al Alibaba and I would sell those on eBay and I would sell them to to friends and to people at school that one actually did did really really well and I made good margins on that and pretty high volume so it was the the

10:51 DVDs were bootleg fake like other people were cloning the DVDs then selling them and then you were kind of shipping them to the US yeah they they 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 oh wow okay it was really fun I don't know it was so weird at the time but like I actually enjoyed like shrink wrap it was creating the final product you know it was like this tangible thing that went from no value to turning into like a tangible hard good with actual

11:37 value and yeah obviously in hindsight you know packaging that together you would know for sure that like their bootleg but again I was like 11 years old you know so I didn't I was more naive than I am today okay and then the the cargo shorts were kind of like they weren't actually abomb but it was a similar style I think that they were ABI honestly they were from Sri Lanka they're postmarked from Sri Lanka AB comes at the time Factory was in Sri Lanka and it would say made in Sri Lanka on them and and so they would come with the labels shipped separately so you still today you have to kind of ship to import stuff you gotta like basically take the the label off in many many ways when you're importing apparel and so they would ship the labels separately and then they had this little sticker

12:23 thing or or puncher thing that would punch the labels on each of the shorts but yeah they certainly were labeled ABI I think that they came from the factory at ABI you know probably somebody was selling excess inventory or something on the side interesting wow talk of what 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 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 like oversight and insight into to 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 and speaking of apparel and clothing you're wearing a very bright and exciting very

13:10 vibrant shirt there's a question from David George on your board at a6z he said what's up with the shirts you know I first of all I've always loved wearing things that stood out that were just different from from other other people right when everybody goes one way I go I always zag the other the other way and so I've just always been I don't know unique in in in some way so I I you know found some really ridiculous shirts like like this one and I would wear them to the office uh you when we were going back in in 2019 and in 18 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

13:56 wrong is the business not okay you know are you are you depressed right now so I basically kind of pigeon hold myself into having to wear Crazy Shirts every single day but you know a lot of the like irony here is that I also don't think about what I what I wear each day kind of going back to you know how like Steve Jobs did and like lots of people don't don't now my closet is full of of ridiculous shirts like this and then I wear clickup sweatpants every day when it's when it's not you know 105 degrees out outside right now um but that whenever I go to the office I wear the same thing every every day just a random colorful shirt and click up sweatpants so I didn't have to think about anything and I still got like you know my my brand across so to speak and so now it's

14:41 it's kind of just part of who I am yeah that makes sense my my wife always gives me a hard time of wearing I just have basically black t-shirts and just like startup swag from like portfolio companies and stuff and and then I got you know plain plain kind of crew neck sweatshirts like this so but yeah you just have like a rotation it's like oh this one's clean throw it on don't think about it similar what the sweatpants Doo sweatpants jeans and the jeans if you're you're going out doing a lot of stuff that day so so we hit on one of the near-death experiences what was the next one so when I was 20 years old and and by the way this is Flash forwarding so we're we're skipping a lot so I'll give like a quick die is I went to Virginia Tech and you know my I feel like my

15:29 whole life growing up I was I wouldn't say meant to meant to is not the right word but almost like 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 the things that I'm learning I'm not going to use later in life and I'm going to forget them by the way I'm going to forget about a lot of this stuff now there's exceptions to everything right so like make take you know that take that as like the 80% case the 80% of school for me was was totally worthless and useless and you know I thought college would be the same way

16:15 and I went to and I had started a I 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 um the margins on that are actually in insane margins on mobile dejing for like sweet 16s and birthday parties and things like that what's the rough like economics is it like a little bit of spend up front and then just like just pay for your time basically exactly so the the spend the cost is just the equipment and you know the equipment is actually not that expensive I mean it would be1 $200 a speaker you need a couple speakers I used a computer a laptop and I would very much um you know charge anywhere from 300 to four $500 an

17:00 hour now it takes an hour or two to set up so you know all all in there's there's a few more hours of course and and getting the whole operation up and down but yeah for me that was absolutely insane money and so I I saved a a lot of of money during that period And I when I went to college I you know never forget I I have to take accounting for a year and so I go I go into accounting you know 101 or whatever it's called and they're 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 you know they should be teaching you how to use QuickBooks or they should be teaching you how to hire an accountant right not actually teaching you how to do all of the Tactical things around

17:46 accounting so I never went to class after the first day I was like this is just totally use useless and and I worked on businesses I worked on my uh I created an entertainment company company there and you know we we we built some some music we I started managing a couple of rappers and we had a lot of fun and you know made made some money I learned a lot and I was managing their social media which we'll we'll tie I'll tie back into later in 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 would I found this

18:32 Disney program Disney college program and I applied to that I was like you know I I always admired Disney for customer support and it was somebody 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 them Montreal and I actually I loved it I I lived and work 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 now nowadays they probably got in a lot of trouble for how how much they pushed people but you know back then it was it was extremely in 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

19:17 able to empathize with them and still kind of put a smile on and not have it affect you you on your in your dayto day so this was like one of the Disney theme parks yep Disney Disney World it was in Orlando okay and you drove the monil I drove the monre rail 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 I think a couple of them were understanding why customers had such high expectations being EMP empathize 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

20:03 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 and rightfully so to some extent you know they don't get to go off and it's their first time going their kid 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 you know their expectations and and the difference in reality is is a lot of times how happy you 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 it's not you it's it's them and it's not that it's their fault and it's not that they're wrong uh just try to empathize with them and try to understand and help solve problems so

20:48 I think that was 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 uh when you're smiling when they're they're really angry about something and I've had that happen before too but you know solving problems with optimism I think is is a big takeaway I got from that yeah I guess I wouldn't I wouldn't have expected that but that makes yeah I mean because your point I I mean we've looked up because we have kids we've looked up how much it cost going to Disney World Disneyland I think it's at this point it's like4 $15,000 if you kind of are a family of four doing the full couple day trip from out of town you're flying in you're

21:35 staying at the hotels that's like 20% of annual income in the US like that is a median annual income like that's a lot of money for some 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 like dealing with that customer to understand why they're upset and why they're frustrated about 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 at all that's what I saw is 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 our

22:21 company and still 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 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 I'm never goingon to do that again I'm gonna do the opposite So when you say you you really then care and value about your employees that click up what does that look like first of all the the biggest thing which sounds almost kind of dumb saying it but have managers that care managers that give a and I think that really really really matters and and it's 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

23:08 equally as as true that it's very rare to have managers that care about the team and care about the company in the same way that they need to be company first right you've got a lot of very empathetic managers that will love their team and become a family with their team but if you have that happen you've over rotated in the wrong direction and you know they've become protective of their team rather than protective of the company and objective in evaluating their team and upleveling their their their teams um so you have to strike that balance and I think honestly that's like one of the biggest things to get right is having managers that care about the team and care about the company I've heard the analogy is you you don't treat them like a family you treat it like a sports team where it's like you all work together you you know people bring the

23:55 skills to you know to win basically and I think I think the sports team one is an interesting one where it kind of makes more sense than the family yeah we say crew because it just sounds good saying click up crew but you know it's it's very similar to that that team analogy where you have to rely on each person in order to make the boat well first of all not 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 opportunity to understand what's what's wrong give them opportunity to grow but if they're not the right person then they're not the right person and you've got to be okay with with moving on with people and you know iterating on your team and I think that's really important it's also

24:40 really hard to do for managers right it's it's like it's not doesn't come naturally to want to you know let people go and make your team better but that's the Natural Evolution of of startups and of companies and of teams and if that doesn't happen I think it can 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 way the other person is pulling the team down like you can't have that at teams you've really got to have a a players all around and that's easier said than done have you learned from any mistakes related to that a click up yeah tons we we made these

25:25 mistakes ourselves honestly like how did that go terrible there was an opportunity I had like a year and a half ago where I I realized what had happened and really I for a good for that scaling period when we were growing really fast We Grew From like 100 to 800 employees in a year everything that went wrong could 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 and it's not like it's necessarily a bad thing I think a lot of companies big companies you kind of have to be political in the work sense and you know making yourself look good and building your Empire up to show you know how many

26:11 people that you were able to manage uh but it's a really bad thing for startups and those people I I a lot of these these lessons you hear anecdotes from before you know like a players will hire B players and then the people blow 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 about the company and in our mission more importantly of like 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 it's this isn't the right place for them where where we

26:56 are focused on this Mission not not other other missions and I think that was like and if I had to distill it into to 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 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 clickup is productivity platform that enables teams of all types and all sizes to work together and 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

27:43 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 in on Bo so many different products and data synchronization between those those different products so we drive efficiency through using a single platform that is very intentionally focused on saving you time yeah I have checked it out a little bit I actually tried to tried to switch over switch everything from a different one that I use into clickup that I've not been happy with and the export I messed up and they only let you export once a day okay so I couldn't go back and reexport

28:31 that's one of the reason I was I'm like all right I'm going to give a click up 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 got to fully onboard yet but it's pretty interesting yeah I'm look I'm happy to to help you after this also and and we have you know very quick imports from pretty much every every tool out out there where you can use an authorization through an API and and we can import import things for you so happy to happy to set things up but that was actually one of the insights I had early on on too is we needed to be able to import your work very easily from the other players out there and that was just honestly my intuition my gut that I was like how am I gonna get myself to switch from we were using we were using 15 productivity tools at the time I mean I was obsessed

29:16 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 a sa for lists they only had lists at the time and we used trell for boards they only had boards at the time we first thing we built 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 AA in 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 on day a th in another tool this episode is brought to you by work OS if you're building a B2B SAS app at some point your customers will start

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30:49 your first Enterprise customer you should consider using work OS integrate a minutes and start shipping Enterprise plans today check it out at work os.com that is work.com so I I guess before we get even deeper onto the clickup stuff I'm curious then you had another near-death experience that I know we were going to hit on what was that yeah so when I was and after this was after I came back from Disney i' 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

31:37 way I've never had the outof body near-death experience that like people talk about but I had this more I don't know futuristic experience where I was like looking at my future and and really intimately focused on the things that I was doing then and prior to that and I was like this is not how I want my future to be and I don't not want to spend time in college anymore I I hated it and I thought I was wasting a ton of time in life so it gave me that that literally in my had I was like if I survive from 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 meant to build in this world was to give jobs and create things and and enable resources and I

32:23 fortunately made it through that and that's exactly what I did I dropped out of school and I started a my first like s SAS tech company it was social media Automation and back then I was I was coding I was in the weeds I was Hands-On and I grew that business into 20 five 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 like cliche as that sounds you know but it was more so in the sense of like are you having net positive impact on the world that's what I was focused on and I think increasing people's egos on social media was not net could be it could be helpful I guess

33:10 but it's probably not like the most impactful thing you could be doing 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 from Craigslist and I still don't know why that hasn't been done I argue maybe Facebook has started to do something like that there's offer up they still don't accept payments they don't have reviews wait offer up doesn't accept payments you still have to do it off platform all of my knowledge is based on when we started click up so it's 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 a public transaction there and give reviews on that public transaction yeah maybe they

33:57 maybe they now but if they don't I'm going to start this at some point or somebody somebody listen to this podcast to get started so we built click up 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 it was about a month where we built that thing to switch between list View and board viiew 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 click up so why was it important to be able to switch back and forth because it I guess doesn't seem like that big of a deal why why was it a really big deal 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

34:44 a board View and then we had tasks in Assa here in 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 jir 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 really okay so then what was kind of the

35:31 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 what what did you lean into next the 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 and 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 scheduling everything else outside of project management that is in some way connected to project management or Work

36:16 Work Management and that was where we really kind of realized most of the or original Vision that I had of being able to put all your work in one place but now naturally you know we didn't launch those most of those products with 100% Future parody 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

37:01 product L 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 and that's ultimately what we did click up 3.0 was later in 20 know 2122 really was was kind of when we we ended up building most of it in 22 but we we we were working on it for over a year and a half for two years and 3.0 was solving a lot of those things I talked about in feature parody really getting to a point where the products themselves are actually usable and replaceable you can replace the other

37:46 other products that you're traditionally using but also redoing a lot of performance stuff we we scaled really quickly and through that process of shipping every week we did not do things the right way technically speaking and we just built as fast as we could so we really had to go back and re-platform and re architecture and rebuild a lot of the things to make it reliable and make it performant and that was that was 3.0 and that ended up taking a lot longer than I thought it would me 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 click up at your local time at 8: a. when is traffic clickup would be generally unreliable and in many ways unusable for

38:33 the first hour or so of your work day and we would go down constantly I mean we were having huge in major incidents every single day and there was no quick fix that we could do anymore the the long-term things were going through sharding and 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 this was make a break we are either gonna gonna get out of this and our customers are going to forgive us and they'll stick with us or we're gonna lose everything and not

39:20 have customers that want to be with us anymore wow a lot to reflect on I guess two questions related to that how how did it get to that point where you you just kind of started slowing down I guess and how did you get out of it like it seems like now you 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 a lot of this slowdown happened over time and a lot of times that it happened we were able to do patches to make to fix those those functional things but ultimately we got to a point where our database we a monolithic database and the database was just too big we scaled up vertically as as large as we could and we were distributed in the

40:07 synchronization sense so we were not we didn't have different databases for for charting for having like different data and different databases all of our databases were replicated in real time around the world so it was still one database even though we had eight regions oh so you just anytime there was a change You' replicate the database in a different Market yep exactly and that would lead to if people are working in different regions there when during peak times we would lead to a ton of problems because you you get the cues 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

40:53 even when there wasn't and it would transpire in you know everyone getting super pissed off rightfully so pissed off that they're they they feel 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 in your same re we had we had two databases in a region sometimes in one database you're creating it 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 que when the those the cues were lower and you know the synchronization was actually happening so then how did you how did you get out of it did I me sounds like you probably

41:38 just rebuilt the whole architecture or like is that is that how you got out of it or how did you do it we we largely rebuilt everything and on the infrastructure side you know we went through sharting and micro sharting and are now enabled to really scale databases by the horizont Al approach right just adding more databases rather than scaling them them up vertically and you know that's really important obvious obviously for for many reasons and that was what enabled us to really get out of it that s that single thing is is the biggest the biggest piece for sure that we we couldn't really everything else was cherries on top things that you know we could patch but not totally fix we had to go through charting and and really a re-platforming as a whole and

42:25 we also had to became operationally con 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's a lot of variables and like and 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 didn't I I

43:11 wasn't you not I'm still not the most experienced engineer in the in the world and especially with like very complex web applications we didn't really have any reasons why you know I I I would find memory leaks and things like that but we couldn't really pinpoint exact things things and I had a after we scaled to that you know 800 employees or so in that really troubling time I had an engineering manager meeting and I when I started talking to managers and started talking to ic's more I felt we 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 backend and I was expecting to get like a few people yeah

43:57 half like 50/50 at least or something who knows yeah just to make the point of like hey we probably need more fun in folks zero people rais their hand literally zero people ra raised their hand in this management meeting and that was when I was like holy you know like we've got to fix this and and we did and you know we went and I fire I found the the most complex web applications like Microsoft teams and hired the people that really built that zero till one and we again took us a while to 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

44:43 to where we were back then so what do you tell someone when they're 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 assuming it was a better pitch than that but like what's the pitch then if you're in a Founder in that spot convincing somebody to come over first of all I think you have to find the right the right people that that also feel I think when when you do the zero to one the zero to one people are different than like the one toxx people and Microsoft teams for example was it's very different than Microsoft as a whole back then it was really built as a startup by this guy Bryan and it was a you know startup within a massive company but these people were super excited about what they were building and they were they

45:28 were going as fast as they can and they they felt like that they had something there you know of course Microsoft benefits from like infinite distribution for for free but it you know 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 that same level of distribution and the point I'm making is that there were a lot of people you know a couple years ago and we're going through this that had already built Microsoft teams and felt like the startup Vibe was was gone it was 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 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

46:15 like zero to one thing but we need to 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 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 the the founders need to do a lot of selling and 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 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

47:00 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 from Microsoft teams that really wanted wanted to have more impact and wanted to go back to Startup mode you be open you be transparent you know you give them the pitch you make it really sexy make it exciting hit the hit the urges that they might have or the the needs that they're looking to fulfill but then also be like hey this is that like 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 all that kind of stuff yeah and I think the hard piece is is something that it really really matters is finding people that want to do hard and the only way that I found that to like everyone will say

47:46 that they want to gener generally speaking some people will actually be very transparent and say like hey no I you know want to coast in life right now and it's not my thing but most people will say hey yeah I'm of course I want to do hard hard but it's I find that that's not always true and and hard is also very subjective right it's like it's like you can be hard at one thing at Microsoft that was extremely easy at a startup super subjective so one thing that I do is I ask people that are joining clickup that I interview always and 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

48:33 something that makes you feel like empathetic towards them it's probably something really hard you know if you're like wow I feel I feel for you that was that was difficult um 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 that have gone through you know a relatively easy life are going to be great and enjoy going through a lot of really hard right now at a startup that's very intense and very stressful and the other thing reason why they may not ansers they may not want to talk about it but I also found that people that don't want to talk about it didn't really go through that hard thing with like fortitude with with strength through adversity I think that's really important is to and I always ask like hey what was something

49:19 positive was there anything positive that came out of that and sometimes people say like what the hell we got you know my my my father died my you know son died how could you ask that but a lot of other people will answer it with you know yeah taught me like 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 yeah just the ability to reflect on the things happening and and learn from it I mean you got to be a learning machine if you want to be a startup I mean things are always things are always changing you gotta be moving quick too one thing I thought was interesting that I've I've heard you mentioned before going back to kind of the the days of getting clickup started

50:05 you guys did 5 AM standup meetings every morning talk about doing hard stuff tell me about that that just sounds like very intense but sounds like it works it was extremely intense you know and it it certainly didn't scale that's one of those things that 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 did 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 palto showed up you Googled Silicon Valley and Palo Alto showed up wow okay I swear to

50:52 God so we're like all right let's go to palato let's drive to palato so we drive to palato and I was expecting like Reno with startup lights you know just like startup startup startup startup and palato is like the sleepiest place in the world yeah just like a little Suburban little like single family homes like ranch style right and they have like an i they have have an ordinance there you can't have signage like much signage at all and so I 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 and and work at and so that was that made way more sense and and that's what we did it was six or so of us

51:39 living in that house and you know I was I set the stage as like hey this is probably GNA be the hardest thing any of us have ever done um but it'll be worth it in the long run and you'll be rewarded over 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. standups every day there is no drinking there is no going out um this is it this this is this is it for this year and I always said this year I always said one one year that was that was exactly what we did you know and we weren't 100% perfect on it but i' if I had to give a score I'd give us like 95 and and it was it was incredible and I'm very grateful to those people early on for actually doing that I don't think

52:25 we would have been successful otherwise because the category would have I mean our category goes so fast as far as in iterating and innovating and it's a lot of kind of like copycat in our category you know where where it's like it's like we build something and then our competitors build it and and then you know it becomes table stakes and then you kind of have to keep in innovating and so my thing always and still is today is just stay ahead it's just keep innovating faster than competitors can and that's the way to stay ahead in our category and I don't think we would have done that if we weren't as intense that that year but that was definitely the thing that did not scale after that year I had to stop doing that where like we had to be more legit 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 6:00 a.m. so

53:11 it's just whenever they wake up I wake up and no alarm but they wake me up every morning super early um so that I was gonna ask you as you were getting into that 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 I think one one of my philosophies also is that like you you any any competitive category you have to do everything right like you you don't have to do all right immediately but everything meaning you've got to do marketing right you've got to do branding right you got to do product right you got to do engineering right you got to get tal Talent right all of those things have to be done really really well and you can get one right in a non-competitive category usually that's only going to be product Maybe

53:56 it's go to market if you if you got like a decent product but like some 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 that's really difficult for for Founders and for especially when you're starting out and you're not able to hire you know experienced PE 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 so how did you do that because I think I I remember you've mentioned before like it was kind of pretty Scrappy literally messaging people try the products like

54:43 what works kind of the first couple people hundred people I don't know what you consider like the zero to one stage but how did you get people to start using it initially we did we did a lot of growth hacking one of one of the things that we did was we built this like script that would scrape all of the review websites like Capa and G2 crowd and anybody that would give any of our competitors three stars two stars one star we would get a notification of it and we would try to match up their name on LinkedIn to go find them on on LinkedIn and go message them and that actually worked pretty well and 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

55:29 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 didn't feel automated you I think nowadays that would feel like I AI so maybe that tactic doesn't work work nowadays anymore I get like 50 AI emails a day I'm just like stop unsubscribe block the domain like it doesn't work but but that's that's one of the things that those are the typee of things that we would do and you know we would do SEO right we would do a lot of content and so you you you we we never had early on any Spike anything that was just like oh this was crazy insane growth for those first couple of years it was all very consistent it was all consistent growth

56:15 but that growth was compounding and that growth very much stayed on that trend of of compounding and going up in in the curve that you know is the classic one that everybody wants to see but to me it didn't feel like we were ever successful those those F first first few years and I didn't really have anything to go on you know we didn't have investors we were we were bootstrapped until 2020 so you know for for our first several years we were we were very much bootstrap and I didn't know that we were successful so to speak we but we were we we were growing you know 30 40% a month on revenue and you know we we had gotten to close to 10 million in ARR on our own bootstrapping and we didn't spend any money on

57:02 marketing really at least on like acquisition traditional acquisition Mar marketing but I didn't even know that we were we were doing well which maybe kind of brings us to investors also yeah so you were crushing it but you didn't really know you were crushing it just kind of thinking about maybe from that Z to 10 million phase of of the business like did people just retain was it really sticky were they spending a lot of money was the it's on like the growth was consistent like why do you think it worked early on if you could go back reflecting on it now we we definitely had the adop the adoption piece matters more than anything like retention like our our users and retention in the form of like user metrics our users actually using the product and are they getting hooked is it something that they're

57:47 going to stick with regardless of having you know a customer a success person by their side teaching them how to onboard it because we couldn't do that at the time so that was what we focused on more than anything was like user user metrics like let's just make sure that this thing is great and and sticky and we you know had a a variety of like pay Walling options but that piece was also key to getting right and I was just honestly kind of winging it because we didn't have you know all of the data tools that you have today you can really run true unbiased experiments with and and learn from so how'd you do it trial and error and and surveys surveys are are I would say like one of the biggest things we got

58:32 right and we still do a ton of today is surveys and we do short surveys we do 60-second surveys asking people a couple of questions and people users are generally very honest I think people tend to think that like users wouldn't be honest because it's it it's not helping themselves to say hey I would or wouldn't pay for this feature or how much this feature is is worth to them but what we found is they're shockingly honest and in answering questions and that was how I did a lot of the pay wall decisions is 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 you I would learn a lot from that and that was that was really kind of how we iterated it on pay wall and

59:18 packaging and more importantly on product you know we do a ton of surveys today too is asking how people feel about a feature that we release and we look at the data for sure but we also the qualitative thing is the thing that matters to me more than anything is the details of like why or why not somebody is using it and what else do they want on top of that so if I'm listening to this this isn't 2017 when you're like 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 well I think it's it's actually probably very much the same I mean we we've changed a lot of our process just to make it more consistent and more formalized and more scalable but it really is just winging and it's it's you

1:00:04 writing the questions the founder writing the the questions like it was me writing the questions 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 yeah and it's using we used to use type form we use we use clickup forms now and we have great reporting inside of type forms didn't really have good reporting but we we leverage all of our other reporting dashboard capabilities and clickup now so we can like get really cool granular insights and Trends on on the surveys

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