JAMES: Welcome to Happy Paths, where we unpack the human stories behind some of the most used, the most influential, and most famous software from the internet era. I'm James Evans. I'm the CEO of CommandBar and the host of Happy Paths. Project management is one of the largest categories in all of software. From side hustles to huge multinational corporations, teams of all sizes use project management tools to plan and execute their work. And the number of tools in the market for project management is as diverse as the people that use them: Jira, Monday.com, Asana, ClickUp, and many others. Each brings their own unique spin on how to break down work and track progress. But one tool, perhaps more than any other, has influenced how other project management tools work. And that's Trello. For this episode, I talked to Justin Gallagher, who worked on Trello for more than ten years, starting with its founding as a hackathon project and running through its meteoric growth and eventual acquisition by Atlassian. We talk about Trello's origin story, the opinionated way Trello encouraged people to break down their work, and the product's impact on future generations of project management tools. Like many people who find their way into product, Justin didn't start out in engineering. JUSTIN: I actually went to school, planning to major in geology. I was really into rock climbing and mountain biking and being outside and stuff, and so I started down that path. And that was cool but got a little chemistry-heavy for me. And I was like; I don't know if I'm still into this. And lucky for me, I went to a liberal arts school, and one of the requirements was that we take another science. And computer science was one of the ones, so that was the first time I'd ever taken a computer science class. And I thought it was really cool. I'd always been into computers and tinkering around with them and that kind of stuff. But I'd never done really any real programming or anything. So I thought it was cool, and I just kind of kept taking the next, the next. And ultimately, I switched my major. So I came out of school with a computer science major. This was in the early 2000s, just shortly after 9/11. It was a pretty hard time to get a job. So I sort of tried to find my way and figure out what I wanted to do and what was even available. Ultimately, I went into consulting, and I worked for a Big 4 consulting firm to start, which was, I don't know, it sort of just was an opportunity that landed in my lap, and I took it, not really something I had pre-planned. But it turned out to be a great way to start my career. But ultimately, I had always been interested in startups, and technology, and that sort of stuff, and I was having the itch to move over to something like that. But ultimately, I got really lucky and ended up at Fog Creek Software. That was sort of a funny story where I had decided to build an iPhone app because that was brand new. The iPhone or iOS SDK had just come out. And I thought maybe if I build an app, one, it seems cool and awesome, and I want to learn how to do that. But also, maybe then I could sort of convince these companies that I can build something and do something, and I'm not just some, like, big corporate consultant guy. So I decided to do that. And in the course of doing that, I had to learn a lot about how to do that. And I spent a bunch of time on Stack Overflow. JAMES: Fog Creek Software is an interesting character in the dot-com software scene. It was founded in 2000 by Joel Spolsky and Michael Pryor, originally as a consulting company. But then the small team of about 30 started churning out hit products. One of their early winners was a bug tracker called FogBugz that competed with Atlassian's Jira. Here's Joel Spolsky giving a brief introduction about it. [Playing Clip] JOEL: Hey, it's Joel. I want to tell you about FogBugz. It has five big features. You got a wiki for writing documentation. There is a project management system where you list all the things you're going to work on. And then FogBugz actually tells you when you're going to ship, and this is really cool. It calculates the probability that you'll ship on time. There's a bug tracker to keep on top of all the bugs you need... JAMES: It wasn't a company known for one huge thing but rather a collection of popular products. Like Trello, Stack Overflow also originated at Fog Creek. JUSTIN: I was asking a lot of questions, and over time, sort of started to learn a few things and started to answer some questions and contribute back to that community. And, at around that time, they were launching what they called their Careers Product, which was a way for companies to find programmers that met a certain skill set based on their activity on Stack Overflow. And so, Michael Pryor, who was one of the co-founders of Fog Creek and Stack Overflow, sort of spun out of Fog Creek as a joint venture with some other folks he was testing the Careers Product. And he saw that I was in New York, and he reached out to me for an engineering job. I knew I wasn't going to pass muster as an engineer there. My skills had atrophied to that point. But I told him kind of what I was interested in, and he asked about a product management role. And I said that sounded great. I'd never really heard the name of that role, but just the description sounded amazing. And I got hired, and I started there as a product manager in June 2010. JAMES: Fog Creek was seen as a rather unconventional place to build software back then. Their mission statement didn't revolve around a particular product or a particular outcome they were trying to achieve in the world. Instead, their mission was to build the best place for developers to work. The thinking was that a software company that could attract the best developers would eventually have an advantage over every other software company. Concretely, this meant that software developers were treated really well at Fog Creek. This might sound incredibly obvious today when every company fiercely competes over engineers with huge comp packages and generous benefits. But Fog Creek was early in this trend. They gave programmers private offices, Aeron Chairs, and generous slices of equity. And this was happening in the early 2000s in New York City, not Silicon Valley. [Playing Clip] JOEL: The truth is, the only reason I started Fog Creek Software is because I kept trying to look for a great place to work in New York that treated software developers well, and I just couldn't find one to work at. So, in desperation, I finally made one. I mean, I would go to parties, and I'd meet somebody, and I'd be like, "Hey, what do you do?" "I'm a programmer." "Oh, me too." And they'd say, "Do you know any good companies to work for in New York?" And I'd say, "No." Everywhere I looked, I saw companies that were having trouble recruiting programmers and not treating programmers well. And they didn't put these two things together. They didn't realize that if they treated programmers well, it would be easy for them to recruit programmers. And so I decided that that was an opportunity that I had to fill. And I just needed a place to work that I liked. So I started Fog Creek. JAMES: They also didn't take venture capital and instead focused on sustainable growth rather than growth at all costs. JUSTIN: Fog Creek had a bunch of products that were selling and making money, profitable but not growing at a really high rate. And so, looking ahead, Joel and Michael sort of could see that there was a sort of an asymptote coming. Like, revenue and growth were going to plateau at some point in the future, and they were trying to get ahead of that. Stack Overflow had recently spun out, so that was kind of its own thing. And so we had this internal initiative called Creek Weeks, which was a way for people to take time away from their normal, you know, everyday job and come up with a creative idea, spend a week on it. And, you know, we kind of would talk about them as a company, and the hope was that one of those would turn into the next thing. And so myself and another guy, Bobby Grace, who was a designer at Trello for a long time and actually still is, we took a joint Creek Week, and we worked on this idea. It wasn't either of our ideas. The core of the idea came from Joel. But it was this idea of really that...I already talked about it, but the simplified Kanban workflow for anybody. And so we spent two weeks on it. We built a really simple prototype. It was sort of Trello, like, for anybody who's seen Trello. It had lists, and there were cards, and you could drag the cards. But it didn't save state. So, if you created cards or dragged them and then reload the page, they were gone. And it didn't have really many features beyond just the dragging and dropping and the visual hierarchy. But we showed it to people, and people thought it was kind of cool and saw the potential in it. JAMES: The origins of Trello reminded me a bit of the episode we did on Gmail. Paul Buchheit described a similar story about how the first version of Gmail was actually shipped in a single day. And just like how Gmail was built at a time when there were plenty of other email clients out there when Justin was hacking on this early version of Trello, Kanban was already established as a best practice in software development circles. And there were other tools that used it. JUSTIN: Basecamp was around for sure. Now the company is called Basecamp. At the time, it was called 37signals. There were a lot of enterprise kind of project management tools. Jira was a popular one, more for developers, but it was definitely something that was used at the time. And then there was a host of to-do lists and that kind of thing that were around. But they were more for the individual rather than sort of collaborative and for the team. It was definitely a known thing, and there were tools for doing it. But it wasn't something that had extended beyond software developers. Like, you weren't seeing marketing teams or design teams, or business teams using that kind of a workflow. And that was sort of part of the key insight to Trello at that time. JAMES: What started as a Hack Week project was now hurtling towards becoming a real product. After the break, Justin talks about when Trello was launched to the world. So, after Creek Week, Justin and some other developers at Fog Creek continued working on Trello. And soon, they would get a chance to show it off at one of the biggest startup competitions at the time: TechCrunch's Startup Battlefield. JUSTIN: So two developers, Daniel LeCheminant and Brett Kiefer, came and joined us. And the four of us spent about nine months working on it from that point until we actually launched it to the world. And there were sort of two reasons for that timeframe; one was it just took a while to get to the point where we felt like it was finished enough to really put out to the world and get people excited about it. But also, we had at some point...I don't remember exactly when, but at some point, a few months into the journey there, we had applied to TechCrunch Disrupt, and we got accepted. And so there was a date. And that sort of put a line in the sand where it was like, all right, that's when we're launching. And part of the deal was you actually launch there. That's when you first are, you know, publicly available. And so that gave us a time to shoot for. And we did have users before then, but it was sort of in private beta. We had...I don't remember the exact number, a few hundred users. And so we would get feedback from them, and talk to them, and add features, and share them with them. But we didn't launch publicly until early September 2011. JAMES: It's funny to picture all these teams working feverishly, knowing they had to ship by a specific date. It kind of reminds me of the energy we felt at Y Combinator leading up to our demo day. Nowadays, startups launch constantly on Hacker News, on Product Hunt, or just announcing their new stuff on Twitter. But the forcing function of a deadline always helps to avoid the classic startup trap of toiling away on something before you know whether the world wants it in the first place. Here's a clip of Joel Spolsky at Startup Battlefield demoing Trello before a panel of judges. [Playing Clip] JOEL: Hi, thanks. Does anybody use Trello? I can't really see out there. Could you raise your hand if you use...make some noise. Nobody? All right, there's a few people using it. [laughs] Since we launched...first of all, if you don't know what Trello is, it's a list of lists. And that is kind of what it looks like. It's web-based. There is, of course, iPhone, Android apps, et cetera. It's real-time. So, when you make a change with any web browser, it instantly shows up everywhere else. JUSTIN: Looking back on it, we were very informal about it. And we'd used a lot of intuition more than any real kind of data or analysis on it. But, you know, we built that initial version in two weeks. And we showed people, and people thought it was sort of neat. I don't remember the exact timing. But it was a few more weeks after that we had, you know, the first version that actually had a database behind it and user accounts where you could start to save data. And from there, we just kind of iterated on it. We would meet as a team. We had this green couch in the office. And I remember for our first...I don't remember how many, but many team meetings, like, we would all just sit on the couch. The team was small enough that we all fit on the couch. We would just sort of talk about how it was going and what we were doing next. We got that initial set of users just from people we knew and people we'd worked with in the past and that sort of stuff. And we would talk to them frequently. I remember one of them was a small law firm in New York. And we actually went and visited them on-site and saw how they were using it. And so we were getting some early signals that this thing was actually useful for people. And that was giving us confidence that it was something that was, you know, had some chance of working. And that gave us confidence to continue to invest in it. The other thing to think about there, though, was kind of where we were starting and the advantages we had. So we were very lucky to start a new product within Fog Creek. Fog Creek had other products that were making money. So that gave us time to figure it out, and it also kind of sized the bet we were making. It wasn't going to move the needle for Fog Creek if we had a product that had a few users and made a few thousand dollars a month or something like that. Like, Fog Creek at the time was not a big company but a successful small business. And I don't know the exact revenue figures but millions of dollars in revenue a year. So to get to the next level, it had to be something that had a big impact. And so we were very lucky that Joel and Michael, the founders, saw that and gave us the time to spend on trying to build something that had that potential and something that would be that big. You know, from the early days, I remember one of the earliest things we did was we had some principles that we wrote out on our whiteboard to kind of guide us as we built the thing. And one of them was we wanted to get 100 million users, 1% of them would pay us $100 a year, and we'd build a $100 million business, which obviously, like, it's always funny when people say 1% are going to pay us because that sounds easier than it is. But just I think what's interesting there is the sort of order of magnitudes of those things and how we were thinking about it. So it sort of characterizes the thing you have to build, the broad appeal that it is required to have. You know, for example, we knew it couldn't just be for software developers. Most of Fog Creek's audience was software developers. So we knew we had to go beyond that because there weren't 100 million software developers in the world. And we knew that 99% of these people are going to use it for free. So we have to have a great free version that is really...we used to say the free version is our marketing budget. So that was really how we got people to love it, and use it, and share it with other people. And then we tried to get a small subset of them to transfer over to pay and build a big business on it. JAMES: Even though Trello was built by software developers and Fog Creek made other products for developers like FogBugz and Stack Overflow, Justin and the founding team of Trello had one ironic cardinal rule. JUSTIN: Trello is not for software developers, which is kind of funny, given that that was us. But the idea was Fog Creek had built other tools that were for software developers. We built project management for software developers, source code hosting, and code reviews, and all that kind of stuff. Majority of the audience for Fog Creek was software developers. Again, we wanted to build a big business, and we wanted to kind of go into a new space. And we knew that what would happen is when we announced this thing, the first people who are going to hear it are the existing audience that we have, which majority are software developers. They're going to use it. They're going to start to make requests that are relevant to them. And we knew software developers know about Kanban, so they're going to kind of ask for things like work-in-progress limits, and swimlanes, and all that sort of stuff. And from the beginning there, we said we have to ignore those requests because if we start down that route, it's going to really quickly turn this into a tool for software developers. And, again, there's not 100 million software developers in this world, so we're not going to be able to meet the goal that we set out for ourselves. And so we sort of ignored those requests largely. We didn't totally ignore them. There was a lot of trying to understand them and kind of get beneath those requests and understand how can we build something generally applicable that serves that need but not steer this in the direction of project management for software teams? JAMES: So Trello officially launched in September 2011 at Startup Battlefield, and while it caught on... JUSTIN: We were not the winner. A lot of the panelists, the judges that were judging us, said, "It's too simple. Why would anybody use this over existing tools like Excel? A lot of people were using Excel for project management. "Why would this be better? You know, and then there's other teams that are using more robust product management software that has a ton of features, and you don't have that many features yet." So, like, that was a lot of the feedback. And that was consistent with, you know, in the beginning, we would get people who would try it and they would say, "Oh, it doesn't do X. It doesn't do Y. You know, it doesn't have enough for me." Launching at Disrupt was great because we got a lot of publicity out of that. That was a pretty, you know, at least in the sort of startup tech world, that was a pretty well-watched event. I remember we went into it with, like, 400 users or something like that. I think it was within the first week we had, like, 50,000 people sign up. You know, most of them just signed up to kick the tires a little bit and play with it. And I think, you know, when we got to week two and three, we had, like, a couple of thousand users who were actually using the thing, but still, that was, like, five times what we started with. And from there, it was just kind of slow, steady growth. The insight that a lot of people got when they first tried it was just the visual nature of it. I think that was different than what most people were doing. And whether it was a spreadsheet or a more traditional project management app that was usually sort of more table-like, instead of having tasks and projects be rows in a spreadsheet, they were these cards that were more visual. The lists gave them a sort of horizontal dimension. And so you could really get stuff out of your head and onto the page in front of you and then kind of see it. And people used to say all the time, like, "Oh, it's such a relief. I had this project. I was feeling really overwhelmed. I broke it all down, put it on a board. And now I feel so much more in control because I can just see it in front of me. I know the status of everything, what I need to do next." And so that visual aspect of it was a real differentiator. And the people who got that were our core users from the beginning. And then, over time, as we sort of added functionality and continued to improve the product, that really, I think, was the differentiator and the thing that people fell in love with. JAMES: I remember my first experience with Trello was in my senior year of high school, so 2012. I think I was planning out my senior project, and a friend showed me this beautiful board they had made in Trello. It felt so modern and also personal and just very different from other apps I'd used. I still remember this image of a beach they had set as the background of their board. Everything just felt really clean. And I remember thinking; I want my project to be laid out like this. Fast forward a few years later, it kind of reminds me of the experience I had of seeing a really well-structured Notion page for the first time. Clearly, I wasn't the only one that felt this way. By 2014, Trello had 4.5 million users and had grown too big for Fog Creek, breaking out and becoming its own company with Justin leading product and design. Coming up, Justin talks about Trello's product-market fit and the impact that Trello made on the next generation of project management tools. We've talked in earlier episodes about finding product-market fit. Gaurav Vohra from Superhuman described the algorithmic approach they took to finding PMF, cross-sectioning users who loved the product to figure out what united them. I asked Justin whether they had performed this kind of analysis for Trello and if they'd found anything that tied together the users who loved Trello and kept returning to it project after project. JUSTIN: There was never anything about the users themselves. And we always look for this, and people always ask this. And I don't think it's a best practice for startups. I wouldn't advise [laughs] people to do this now. But we never sort of targeted. It's not like we were like, oh, marketers, companies of 25 to 50 people who are, you know, in this kind of role or something. We never did that. We sort of launched to everybody. But the kinds of projects that they were working on, I think, were the differentiator. And so, the projects were collaborative. We always said to ourselves Trello is not a to-do list. We weren't trying to build a to-do list, a personal to-do list. We thought that personal to-do lists and personal note-taking apps were great, but they weren't very sticky and weren't a good way to make a good business because people would just use them individually. And it was easy to switch from one to the other. So we wanted to be more than a to-do list. We wanted it to be collaborative. And we always sort of said that the visual representation of the board was both a strength and a limitation of the product intentionally. So it was a strength. I already talked about this. You could get it down. You can see it in front of you, especially when it's collaborative. You'd have this shared perspective. We used to use those words a lot. You'd have a shared perspective on the project. Everybody knows where everything stands, who's working on what, what's coming up next, all that kind of stuff. But also, because of that visual nature and just the size of your browser window, you couldn't have too much stuff. You couldn't have thousands and thousands of cards. And I think a lot of times people try to do that on projects. They have, like, every idea goes in the backlog, and they try to just keep it all in there. Often, you get to this point where you just have too much, and you declare bankruptcy, archive it all, and you start over again. We sort of said, like, we're not trying to do that. We're not trying to be the place where you can record everything. We want this to be visual. We want it to be the stuff that's important is, the stuff that you see. And so that sort of gives the sweet spot of collaborative projects, more than just a simple to-do list but not probably, you know, I don't know, building a skyscraper. It was somewhere in between that where it was sufficiently complicated but not hugely complicated. And that targeting and that keeping this tool very easy to use and lightweight really matched well. Like, there was a lot of people who had that level of project, and there wasn't a tool that met their needs until Trello came along. There was this pain point that we could solve, which was there was people who had projects that were sufficiently complicated that, you know, they couldn't keep it all in their head, or a simple to-do list wasn't going to do the job. But there was no tool that made it easy for them to keep track of that, especially collaboratively. And as I said, a lot of tools there were just really complicated or had ton of features. And it would just be too much work and too confusing to put these projects in there. And so it turned out, as we dug into that, that that's a lot of people who had that pain point, which was perfect, right? That's what you want. You want something that's really hard for people and is problematic for them. And there's a lot of people that fit that. And if you can build a tool that meets the need, then you can have a big audience, and you can build a great business on it. JAMES: Here's Michael Pryor giving an update on Trello at TechCrunch Disrupt in 2015. [Playing Clip] MICHAEL: Thanks for having us back. We were here four years ago. My co-founder, Joel Spolsky, was introducing Trello to you with our VP of Product, Justin Gallagher. We were a tiny team of five then, and a lot has happened since. We've grown to 50 people. We took an investment round from Index and Spark last year and spun out of our parent company, Fog Creek Software. And we've been adding a lot of users. So, just how many users? Well, we have 100,000 people a week. We have a million active users a month, and we just passed 8 million sign-ups. There's a lot of people using it. [applause] Thank you. JAMES: A few years later, in January 2017, Trello was acquired by one of their competitors, Atlassian. And Justin stayed on as Trello's Head of Product. JUSTIN: It's a very emotional experience going through the acquisition process. In one sense, it's super exciting, and it's in part kind of why you create a startup, right? Like, oftentimes, there's some outcome you're trying to get to. But it's also like, oh my God, what's going to happen? Are they going to change this, or ruin this, or fire me, or whatever? So it was very emotional. But I was excited. We had some early meetings with the folks on the Atlassian team, and they seemed like really great people. And they seemed to really get what we were trying to do and really be excited about what we were trying to do. And so I went in with an open mind. And I knew it was just going to give me a new experience. I'd never worked for, you know, a publicly traded technology company of that size. It wasn't even that big. I think when we joined Atlassian, it was, like, 1,200 people or something, much smaller than now. But I sort of went in with an open mind. I said, hey, this is a new opportunity to learn new things. They've done great things. You know, they built Jira into an amazing business. They launched a bunch of other products. They have built this company into a huge, successful company. And, like, I think there's a lot to learn there. And I'm excited to go see what that's like and see what I can learn and also what I can contribute. So that's how I went into it. And I think a lot of that rang true. It was a great team, great people, great culture. I had a lot of respect for everybody. And I did feel like I was learning a lot. I just always felt like there was new challenges, new things to figure out. And so I stuck around, yeah. Usually, there's a vesting agreement. So there was a four-year vesting agreement. I ended up staying five years. So it wasn't like I was trying to just get to the end of that vesting. You know, part of it was, like, I had spent seven or eight years working on the product. Like, I just felt like it was such a part of what I did and what I cared about. I had worked and helped to hire almost everybody on the team. I think we had 106 people or something at the time of the acquisition. So I cared a lot about those people. And I wanted to ensure that they had a great experience as part of the new company as well. And, you know, it wasn't just me that stuck around. There was a lot of people who stayed three, four, or five-plus years. Many people are still there, even after I've left, you know, six, almost seven years. I think that's a credit to the culture we built at Trello to start and the group of people that we brought in who were really close-knit and really supportive of each other. I think that's a credit to the wider Atlassian culture that embraced that and really contributed to it and also took some things that we did and made that part of their culture as well. And just the opportunity, like, it was an exciting place to work, lots of fun things and good opportunities. JAMES: Trello obviously still exists and remains super popular. But since it was created, a ton of new tools have risen, each with their own primitives and quirks. I asked Justin what he sees of Trello in today's crop of project management tools. JUSTIN: I think since we built Trello, like, the bar on simplicity of experience, intuitiveness, ease of use, all that kind of stuff has been significantly lowered. Like, all the tools now are doing pretty well there. The idea of a board and that metaphor for kind of managing tasks is ubiquitous now, like, that's everywhere: Asana, Monday, Linear, Notion. Like, every tool has that now. And so I like to think that Trello contributed to that and popularizing that mechanic. And I think the visual thing is a little bit there, too. A lot of tools provide a more fun kind of visual way of doing things. We also had a very sort of almost consumery tone, which at the time was a little different for B2B products, but you see that more popularly now too. So I think all of those were a piece of it. But a lot of other tools did things in a different way than Trello, and I think maybe, in some cases, better. Some of these other tools scale to, you know, full-company usage and broader scale usage a little better than Trello. So there's different ways to do things. But I like to think that we kind of helped contribute to the consumerization of project management tools for business and just making them easier and more fun to use than the older kind of more boring, more confusing, complicated tools. If we tried to build Trello today, if, like, Trello didn't exist and we tried to build it today the way we built it then, it wouldn't work because of the way things have moved on both technologically and just the expectations of users and the sort of state of the world. So it's interesting, like, how the timing of everything makes a difference in the methodologies that work and the success of things. JAMES: That was Justin Gallagher, Founding Team Member of Trello. Thank you for listening to Happy Paths. For more information about the show, visit us at commandbar.com/happypaths, or you could send us a tweet @CommandBar. This podcast is executive produced by Maurice Cherry, with engineering and editing from Mandy Moore. Special thanks to Justin Gallagher and, of course, the entire team at CommandBar. I'm James Evans, and this is Happy Paths. See you next time.